I want to thank Annabelle Brito for reviewing and making suggestions that have greatly improved the story.
This story is a product of my own perverted imagination. It is complete fiction and any resemblance to persons living or dead is pure coincidence. I hope you enjoy it. Please leave your comments, good or bad. I try to learn from corrective criticism.
Enjoy!
*Note: This an extended version of the Fictionmania version, exclusive here.
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Darla
A young woman intends to show her strong willed mother that she can be just as dominant as her. She intends to make a young man into her submissive wife! This story is told in a unique dual point of view narrative.
Anna
I was raised in a household dominated by my mother, a true matriarch. There were just the three of us in the family, mother, my brother Avery, and me, Anna. My father died when I was an infant. Mother raised me from the beginning to be strong willed and independent. I took music, and dance lessons. My mother also enrolled me in speech and debate classes at my private school. She said it would serve me well by giving me confidence and increase my powers of persuasion. She also had me take martial arts lessons at an early age. The first self-defense discipline I took was Taekwondo. After excelling in that, I moved unto Jujitsu, and finally Karate. I hold a black belt in each, so I am well able to take care of myself. Mother wanted her little girl to be able to take on the world and be a success, just like her.
As I grew older I slowly realized that Mother was a strong believer in feminizing males and as a result, my brother spent more time in skirts growing up then he did in pants. My mother even had him in frilly panties growing up. Avery turned out to be a real sissy, which was my mother’s goal. He was not allowed martial arts or other self defense instruction so despite being two years older than me I was easily able to dominate him if I needed to or just felt like it. It also meant he was dependent on me to protect him from bullies at school and in the neighborhood. I took great pleasure knowing I had the physical skills that allowed me to physically dominate boys.
Avery was married was off once he reached the age of 18 to the oldest daughter of one of mother’s close friends who, like her, is also a believer in female domination and male feminization. It later hit me that Avery was bred and groomed from an early age to be a “Boy Wife” so he can be the mate of my mom’s friend, Margaret Harrington’s daughter, Angela. Growing up, Mrs. Harrington would meet my mother on occasion and ask how Avery was progressing. It all made sense now. Avery really had no say in it, one day he was summoned to the living room while in a white summer dress and was told that he would be wed to Ms. Harrington and also take her last name as her young sissy wife. Margaret Harrington was very wealthy and influential. He would be well taken care of. As a result, Avery became the perfect maid and housewife to his spouse.
I met my future wife while studying for my MBA at one of the more prestigious schools in the country. I was preparing to take over as CEO of our family corporation, which, though founded by my great grandfather was grown to its current size by my grandmother and mother. This was in spite of protests from some of the males in the family and criticisms by other males in the corporate world. Under my mother’s and grandmother’s direction corporate profits far exceeded those of others in our line of business. I intended to carry on that tradition. An understanding I had with mother, was that if I wanted to one day take over her corporation and keep it under our name, I would have to find and take a male as my spouse. One that she knows would be submissive and docile in the marriage and would not interfere with the day to day operations of the company.
“A man has no place at the head of our table,” she said to me after I agreed to our deal. “If you could not find one, I will find one for you.”
“That will not be necessary” was my response.
It was in my second year of study for my graduate degree that I found Louis, my future wife. I had become serious about looking for a prospective mate during my senior year in the university. I checked out about 8-10 boys over the next 2 years who I believed I could turn into sissies but all were unqualified to be my wife for one reason or another.
I decided one day to visit the Art Department of the university, figuring that perhaps I would a find more sensitive and emotional boys there. With luck, one day I noticed Louis sitting on a bench eating his lunch. I watched him every day for a week and he was always alone. I estimated his height at 5’7”. He was thin and had collar length black hair. Physically, he was the ideal candidate. Now the question was could I train him? There was only one way to find out. The following Monday I approached him.
Louis
It was my first year at university and the whole thing was overwhelming to me. I had no parents or siblings, in fact I had no family at all. I grew up in a series of foster homes and never really had any emotional connection with the adults or other children. The foster parents I had fed me, clothed me, and gave me a roof over my head, but they never gave me love. I was going to university only with financial aid and student loans. I was hoping to graduate with a degree in Graphic Design and hopefully find work to be able to pay off any loans and make some kind of living.
I was surprised when this beautiful girl asked if she could sit with me. By nature I am very introverted and a loner. I had always been too shy to even ask a girl out on a date. Having no real male role models, to show me the ropes around women and life, I was held back socially with people. It was even more surprising to me when she returned every day that week and seemed very interested in me. On Friday she asked me for a date. I was stunned, but somehow managed to accept. It would be the first date I ever had.
Anna
He clearly liked me and I guessed that his innate shyness kept him from asking me for a date. If that was the case then it was even better than I had hoped. I must have intimidated him and I intended to keep him that way.
Louis
She told me to wear my best suit and be ready the next night at 7:00. I only had one suit but had it pressed and shined my shoes. I wanted to make a good impression. I was ready at 6:30 and nervously paced around my apartment. By 7:15 she had not shown up and I feared I was being stood up.
Anna
I purposely kept him waiting hoping to increase his anxiety. At 7:30 I knocked on his door. When he saw me he had a look of relief on his face. I handed him a bouquet of roses. He took them and stood there in shock.
“Well, aren’t you going to thank me?” I asked.
That seemed to wake him up and he thanked me profusely and turned as red as the reddest rose in the bunch.
Louis
I breathed a sigh of relief when the doorbell rang and Anna stood there looking even more beautiful. She wore a short red dress with matching heels that made her several inches taller than me. I stood there stunned when she handed me the roses. I had never heard of a girl giving a boy flowers and it only served to increase my anxiety. Responding to her question I thanked her profusely and stood aside as I invited her into my one room apartment. Seeing her in that short dress caused me to have an erection which I was sure she noticed.
I was embarrassed by the small size of my apartment and the second hand furniture but she complemented me saying it was cute. We stood there for a moment in silence when she suggested I put the roses in water and we leave for the restaurant. She had an 8:00 reservation.
Anna
I noticed his erection. It was quite obvious and I inwardly smiled. The evening was starting out exactly how I wanted it to. We walked to my car and I held the door on the passenger side open for him, closing it when he was settled in his seat. I had modified the seat belt making it difficult to put on and remove without knowing the trick. That required me to lean over and buckle him in. I purposely brushed my breast against his arm and I swear I saw his erection jump a bit through his pants. I planned on turning him on but there would definitely be no sex tonight.
Louis
I was embarrassed when she held the car door for me and even more so when I couldn’t buckle the seat belt. She told me that the seat belt was tricky and she would have it fixed. I thought I would have a heart attack when her breast brushed against my arm as she buckled it and my erection which had just started to subside sprang up to full size. I could actually feel dampness in my boxers from some pre cum. I was afraid I would ejaculate right then without touching myself. Fortunately it had not leaked through to my pants so it was not noticeable. It did not escape my notice that she was treating me as if I were a girl on a date with her boyfriend, but it did excite me. I hoped the evening would go well. I think I was already in love with her.
Anna
When we arrived at the restaurant I used valet parking. Louis, of course, could not undo the seat belt and after handing the valet the keys, I leaned over Louis to free him from the belt, once again brushing my breast against his arm. I held out my hand to help him from the car and watched him blush as the valet watched the whole act. I wondered if he would say anything about my treating him as a girl.
Louis
Her actions made me feel like I was some kind of sissy but her words were kind and they settled me. The hostess led us to our table and held her chair while I waited for her to be seated and sat on my own. I was grateful that she didn’t try to hold my chair for me when we got to our table. When I looked at the menu I was shocked at the prices and knew I could not afford to eat there.
Anna
I knew the prices would shock him. I had done my research and knew he was in debt from student loans that barely allowed him to maintain his apartment.
“Don’t fret about the prices Louis. It is my treat” I told him.
I had the feeling he was going to protest, but he said nothing. He was clearly nervous being with me. That was good to a point, but I knew if I couldn’t calm him down it might be our last date. I was determined to keep him and turn him into my sissy. After all, he had the qualifications I deemed desirable.
Louis
Here I was with the most beautiful girl I had ever seen and I was so nervous I was tongue tied. I knew if I couldn’t snap out of it and carry on a conversation it would be our last date. I did not want that to happen.
Anna
I was patient with him and slowly I was able to bring him out of his shell. It turned out to be a pleasant evening. When we left the restaurant I once again held the door for him and buckled him into his seat belt in front of the valet. When he blushed he was so adorable that I wished I could take him home and put him in a dress that night, but I knew I had to take it slowly. Instead I gave him a peck on the cheek before closing the door and walking around to the driver’s side.
Louis
She was really sweet when she talked to me and gradually I was able to respond to her. I was once again embarrassed when she held the door to the car for me and buckled my seat belt while the valet stared at us. I did relax a bit when she gave me a kiss on the cheek though I could feel the heat on my face from my embarrassment.
When she took me home I invited her into my apartment for coffee and was happy when she accepted my invitation. When I set the cups down on the coffee table I noticed that she was sitting in the middle of my sofa forcing me to sit close to her. Before I could take a sip she had her arm around me and pulled me to her. She kissed me hard forcing her tongue into my mouth! I was unable to resist her, not that I wanted to but it caused my erection to grow.
Anna
I was pleased with his invitation for coffee. It meant my plan was working. Since the only seating he had was his sofa, I sat in the middle to force him to sit close to me. I figured if I sat at an end his innate shyness would cause him to sit at the opposite end. I had not intended to attack him the way I did, but the date was better than I expected and he was shyer than I anticipated. I was certain he liked me so I went for it. I was not surprised to see the bulge in his pants grow.
“That was nice” I said when we finally disengaged.
He nodded and moved his hands over his erection hiding it from me. I was feeling mischievous so I moved his hand away from his erection.
“Oh my Louis, did I do that?”
He stumbled over his word and didn’t really say anything.
“Well I think that since I’m responsible I should do something about it.”
I began to rub him through his pants. He reached over to stop me but I swatted his hand.
“Leave it to me Louis!” I ordered him and smiled when he leaned back.
It did not take him long before he was ejaculating into his underwear and leaving a large wet spot visible on his pants. A quick look at his faces showed me that he was horrified. I thought he might start crying and that would not have suited my plans.
“It is alright Louis. You are a guy. It is my fault and I don’t blame you. I’ll wait while you clean yourself up.”
I gave him a gentle kiss on his lips and took my coffee as he got up, grabbed a pair of pants and boxers and disappeared into his bathroom.
Louis
It was so embarrassing to ejaculate into my pants like that. Her touching me like that felt so good. I just couldn’t stop myself. I couldn’t look her in the eyes and hoped her taking responsibility was a good sign. She stood up when I came back into the room and told me she had much to do the next day. She kissed me on the cheek and was gone. I wasn’t sure if it would be the last time I would see her.
Anna
The date could not have gone better. Louis was on the defensive, embarrassed and ready for me to make the next move.
Louis
I didn’t sleep much that night. I tried to rationalize what had happened but my mind focused on the fact that I had cum in my underwear. I was certain I had blown any chance with Anna.
I sat nervously on “our” bench during lunch on Monday, praying that she would show up. I kept looking for her the whole hour I had between classes. She never showed.
By Thursday I accepted that it was not to be, so I was shocked when she appeared that noon and sat down and kissed me on the cheek as if nothing had happened. I immediately got an erection which was painfully obvious to her.
“Did I do that?” she asked me.
I nodded, too ashamed to speak.
Anna
He was so cute when he blushed. I pictured him wearing a dress with makeup and a feminine hairdo and felt myself getting wet. I was getting ahead of myself. I knew I had to work up to that and I had a plan in place. I leaned over and kissed him again.
For the next few weeks we met at lunch and got together 1 or 2 nights a week. I introduced him to oral sex. That is how he should give oral sex to me. I kept him on his back and then positioned my pussy over his mouth. Then I rode him to several orgasms. He remained passive and always did what I told him. I made all the decisions. His orgasms were limited to my masturbating him with my panties. After a few times he got hard when I touched his cock with my panties. To keep him from wanting intercourse I told him I was saving myself for marriage, though I was by no means a virgin.
Louis
I had never tasted a woman’s pussy before that first time with Anna, but I loved it. We did not have intercourse and I was almost grateful when she told me she was saving herself for marriage. It relieved a lot of the pressure off me since I really had no idea how to make love to a woman.
Anna
The big test was coming. There was a university costume party coming up where everyone was encouraged to come dressed as a character from a movie. I had my plan in place to feminize and sissify him. If that succeeded, I believed that he would be mine. We continued to meet for lunch as usual.
“Louis, do you have plans for the costume party?”
“Um..no. I don’t usually go to costume parties. I never know what to wear.”
“Will you go with me? I will select our costumes.”
His face lit up when I asked him and he immediately agreed.
“If you are available this evening I will come over about 7:00 and measure you so I get the right size costume for you. We can share a pizza if you like”
“That would be great”.
Louis
She kissed me gently on the lips and left me sitting there. My spirits had never been higher. I was in love with Anna. I couldn’t concentrate on my afternoon classes but tried to get some studying in before she came over.
She arrived just at 7:00 with a pizza and a tape measure. We enjoyed the pizza and then she ordered me to strip. I removed all my clothes down to my boxers. She motioned me to remove those as well. Though we had been naked together, I was nervous being naked in front of her while she was fully dressed.
She started measuring me all over writing everything down.
“Anna, do you have an idea for our costumes?” I asked her.
“Yes, as you may know the theme for the dance is movie characters. I thought we would go as Alfalfa and Darla from the Little Rascal comedies of the 1930s. What do you think of that?”
“I guess that is ok but I don’t know who they are.”
“I thought that might be the case so I brought you a picture of them.
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Darla and Alfalfa, shown above, were star characters in ‘The Little Rascals’, a series of comedy shorts made in the 1920s and 1930s.
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“So what do you think Louis?” she asked me.
I thought Anna would look pretty as Darla
“I like the idea”.
Anna
He was so enthusiastic after I showed him the picture that I knew he was picturing me as Darla. He would be in for a rude awakening.
We had our usual lunch meetings and a couple of nights together before the dance. I didn’t plan on getting to the dance before 9:00 when it would be in full swing, but I needed time to prepare him. I told him I would be at his apartment at 4:00. I figured it would take 2-2 1/2 hours and then we had a dinner reservation. Of course, he knew nothing of that.
I showed up at his apartment in costume, wearing a brown suit with a white shirt and black bow tie. I had slicked my hair down, parting it in the middle and forming a cowlick like Alfalfa had. I carried his dress in a closed garment bag and the rest of his costume in a small backpack. When he opened the door for me his mouth dropped open. He stood there staring at me.
“Do you like?” I asked him as I turned around.
“But..but.. I thought I was going to be Alfalfa?”
“You never conveyed that to me though, did you?”
“No, but I just assumed. I mean Alfalfa is male and I’m male.”
“Not tonight you are! Tonight you are female” I replied with a smile.
Louis
I was stunned when I opened the door and saw her dressed as Alfalfa. There was no way I wanted to dress up as a girl. No way! But it was clear that it was what Anna planned.
“No..no I can’t be a girl.”
“Are you saying you won’t be Darla tonight?”
“I can’t be a girl. It would be too humiliating.”
“So you think that being a girl is humiliating? Why? Because somehow it makes you weak?!What kind of sexist remark is that? I thought you were above that!”
“No, I didn’t mean it that way. It’s…”
“It sure sounded like you did. Well let me tell you something, I enjoy being a girl and there is nothing humiliating about it!”
I had opened a can of worms and wasn’t sure how to get out of it except by agreeing to wear a dress and I did not think I could do that. I did not respond to her statement and for a few moments there was an uncomfortable silence.
“So Louis, are you going back on your promise to wear the costume I picked out, meaning you are not going to the dance with me?”
I hated that she was making it so personal. I shook my head.
“Ok” she said “have a nice life and don’t call me!”
She turned to walk away.
“Wait! That’s it? You’re breaking up with me because I won’t wear a dress?”
“If I can’t count on you to keep your word with me than what kind of relationship is it? I thought when you agreed to go to the dance with me in a costume I chose that you would do just that. Obviously I was wrong. Good bye Louis”.
“Can we talk about it? Please” I begged.
“There is nothing to talk about. Either you wear the costume and come with me or you don’t. What is it going to be?”
I stood there trying to decide. The thought of never seeing Anna again was very painful. But the feeling of humiliation I would suffer was also painful.
“Look, if you are concerned about dressing like a girl I can practically guarantee you that there will be other guys there also in drag. It is a costume party after all. No one will judge you.”
I was certain I would regret saying yes, but even more sure that I would regret letting Anna get away. I knew that meeting her was the best thing that ever happened to me. She turned to walk away.
“Please wait! Ok, I will do it” I said very softly.
Anna
I smiled when he agreed and knew I had him. By the time this weekend was over he would be well on his way to becoming my feminized boyfriend.
I walked passed him, hung his dress on a door and put down the suitcase.
“Ok Louis. Let’s get to work. Strip!”
He hesitated for a moment but then removed his clothes, down to his boxers. I motioned with my hand to remove those also. He had already been naked in front of me so it shouldn’t be such a big deal.
He hesitated for a moment but then removed his underpants and stood there covering his genitals. I couldn’t help but smile. I took out a bottle of depilatory from my suitcase and taking his hand I led him into the bathroom. I spread the depilatory all over his body below his neck
Louis
I was embarrassed standing in front of Anna naked. She didn’t react at all to my nudity but instead remained quiet while she spread the pink lotion on me. Predictably I got an erection. I complained about it burning me after a few minutes but she told me that was what depilatories do and I was to stand there until she told me otherwise. The burning caused my erection to subside. Finally she allowed me to step into the shower and told me to wash off the cream with a wash rag. I was not happy to see my body hair go down the drain. When I stepped out of the shower she patted me dry with a towel explaining that I couldn’t very well wear a dress with hairy legs. I was not happy about wearing a dress to begin with, but accepted it to stay with Anna. I knew the hair would grow back before the spring. I wasn’t planning on wearing shorts before then. She rubbed some kind of oil on my body telling me it would reduce any irritation that could occur from the depilatory.
Anna
He took having his body hair removed rather well. I could hardly wait to see him completely dressed, but I knew it would take time and was prepared to embarrass him a bit further if necessary.
When he came out of the bathroom I grabbed the towel and pulled it off him. He let out a girlish squeak and immediately covered his genitals with his hands. I smiled to myself as I handed him a pair of white satin bloomers that were ultra feminine with elastic around the legs and lace below the elastic.
“Why can’t I just wear my boxers?”
“Girls don’t wear boxers and tonight you are a girl. Are you going to fight with me over every aspect of the costume? If you are, then let’s quit now!”
“No, I will wear the panties and whatever else you tell me” he said very contritely.
He took them and looked at them for a moment. Then he looked at me, pleading with his eyes, but when I did not react he slowly stepped into them and pulled them up to his waist. As I hoped the smoothness of the satin caused his erection sprung to up immediately and though I couldn’t believe he would get any redder than he already was, he did.
“Well, it looks like someone likes his or should I say her new underwear” I said.
“I..it’s not that…”.
“It’s ok. They are very sexy and I am sure they feel very good on your cock but we will have to take care of it.“ I replied pointing to the bulge in his panties.
I knew he was expecting me to jerk him off, but I wanted him horny. I grabbed a piece of ice from the freezer and a towel. I pulled his panties down and put the ice against his cock. Once again he let out a girlish screech and tried to jump away but his erection subsided before he could avoid me. I manipulated his balls back up into the cavity from which they descended, pulled his deflated cock back between his legs and taped it there leaving the head exposed so he would be able to urinate.
“That should prevent future erections until we remove the tape. Now you know why I had you remove the hair from your groin.”
“But what if I have to use the bathroom.”
“Then you will sit like a girl” I smiled. “After all, tonight you are a girl!”
Next I gave him a short white chemise. He put it on without further comment.
As I planned, it barely covered the lace of his panties. Despite having no makeup on he was already looking quite girlish. I knew that by the time I was finished with him he would look like an overgrown 6 year old girl.
Then I took the dress out of the garment bag and held it for him to step into. It was a white dress with orange flowers, short sleeves with elastic on them and a high elastic waist. It was a nice party dress for a young girl in the 1930s which I had made especially for him. By this time he was resigned to dressing up and though he winced when he saw it, he stepped into it without protest. It had tiny orange buttons put on the back which I had to do up. I had the dress designed that way to prevent him from removing it without my help. He was effectively trapped in it, unless he was willing to rip it off and destroy our relationship. I felt strongly he was not ready to do that.
On his feet I put white lacy ankle socks and white shoes with a cross strap, a one inch heel, and a flower on top. Even without my fixing his hair and make-up he looked adorable.
His hair had grown out (at my suggestion) since I first observed him but was a little shorter than I would have liked. Still, I was able to style it to approximate the hairdo that Darla had. The final touch was a white ribbon on top.
Though 6 year old girls did not wear makeup, I applied some in order to feminize and soften his boyish face. I put on a light foundation, some pink blush (though he probably didn’t need it). I curled his eyelashes and put on a tiny bit of mascara, and some pink lip gloss. You could not see the makeup unless you looked really closely at him. He really did look like a little girl and sort of resembled Darla. He was clearly uncomfortable being dressed like that so I decided it was time to reward him, and I sat him on my lap to reinforce our role reversal while giving him a long passionate kiss. Of course then I had to reapply his lip gloss.
Finally I allowed him to look in a mirror. I could see how shocked he was at how much he looked like a girl. I had him practice walking with a smaller stride, brushing his skirt under him as he sat down, and sitting with his legs crossed at the knee or with his knees together. After about 20 minutes he seemed to have the hang of it but I knew I would have to watch him.
Then I took his hand and led him out the door. Standing in the hallway of his apartment building I could sense he was about panic. I put my arm around his shoulder.
“You look like an adult female in a child’s dress. That is the effect we want. Hold your head up and walk confidently and no one will guess your real gender.”
Darla
It was quite embarrassing for me to stand in front of her naked while she was fully clothed. It was even more embarrassing to put on the panties which were so sissy and to get an erection. I think I would have been happy to die on the spot. I wondered how she knew how to tuck my balls up inside me. It was not painful but it did feel strange.
Sitting on her lap added to my embarrassment. She was reinforcing the idea that for tonight I was a little girl, and while I enjoyed the kiss, it caused me great discomfort as I tried unsuccessfully to achieve an erection.
I was stunned when I looked at myself in the mirror after she finished with my makeup. I really looked like a young lady masquerading as a little girl, but what disturbed me more than anything else was the length of the dress. Any movement at all caused my slip and the lace on my panties to be displayed. I really wanted to back out but I had agreed to dress as a girl and I was intent on cooperating as humiliating as it was for me. I was in love with Anna and was determined to do what I had to not to lose her.
It was a greater shock to be standing outside my apartment in the short child’s dress as the reality of being out in public hit me. Only her hug and words of encouragement prevented me from going back into my apartment. When we got on the elevator two girls from the university who lived above me were already there. They had recently moved into the building and I think I was the first neighbor to greet them. I knew them as Rachel and Cindy and prayed that they would not recognize me. They were in costume also and nodded at us, but showed no sign of recognition. I breathed a big sigh of relief. I had spoken to them several times but if they didn’t recognize me I was more confident that no one else would.
Anna had parked a couple of blocks away and it was nerve wracking to walk those blocks on a busy street. People did stare at us, but aside from a couple of complements on our costumes, no one seemed to realize or they just didn’t care that I was a guy.
Anna held the car door open for me as she had been doing. She told me to sit and then, with my knees together, swing my legs into the car so as not to display my underwear to whoever might be watching. She reached over me to buckle my seat belt and her lips brushed mine causing me to smile.
It didn’t take long for me to realize we were not driving toward the university where the dance was being held.
“Anna, why aren’t we headed towards the dance?”
“We have dinner reservations first and I am starving.”
I was going to protest but realized he futility of it. She was clearly in charge tonight and I would have to go along for the ride, wherever it took me.
We pulled up to a fancy restaurant with valet parking. Any confidence I had about passing as a female went out the window as I considered sitting in a restaurant where people could study me if they felt something was off.
“Can’t we just grab burgers at a drive thru?” I asked knowing what her answer would be.
“No, I’m taking my best girl out for a good dinner.”
“I’m not really a girl, you know.”
“Tonight you are my girl, Darla.”
When she stopped the car a valet came to open the door. I forgot what Anna had told me about exiting a car and realized when I saw him grin at me that I had displayed my slip and panties to him. My face turned a deep red and I was happy to escape his stare when Anna took my hand and led me inside the restaurant.
“Hello Miss Worthington-Smythe.”
The hostess clearly knew Anna and gave her a warm hug which was returned with equal enthusiasm.
“Hi Veronica, this is my boyfriend, Louis, but for tonight he is Darla.”
At that moment I wanted the earth to swallow me up. To my surprise Veronica gave me a big hug.
“It’s nice to meet you Louis, or should I call you Darla tonight?”
Her voice was a bit loud and I heard someone say “it’s a boy?”
I couldn’t understand why Anna was doing this to me.
“Your mother is already here at your usual table. Please follow me!” said Veronica.
“Her mother?” I thought. “This can’t be good.”
Still holding my hand, Anna led me through the restaurant. We got a lot of stares from people sitting at their tables. No one else in the restaurant that I saw was in costume and I felt very conspicuous. I could not tell if they realized I was a guy which only made me more nervous.
We were led to a table where there was a beautiful older women already sitting Clearly Anna got her beauty from her mother.
“Louis, this is my mother. Mom this is Louis, though tonight he is Darla.”
I softly said hello her. The waiter came up and held my chair for me to sit and then held Anna’s.
Mrs. Worthington-Smythe already had a drink and the waiter asked us what we wanted.
“I’ll have a Heineken’s” said Anna “and a Shirley Temple for my girlfriend. She is not old enough to drink alcohol.”
Anna
I wasn’t sure that I wanted to have Louis meet my mother that night, but she insisted. After thinking it over I decided it might not be a bad thing to get her opinion. I knew it would embarrass Louis when I ordered him a Shirley Temple. While that was part of the reason for doing it, it was also to show my mother that I was in total control. I also wanted to see how Louis would handle it, since if our relationship was to progress he would have to deal with even more humiliating situations. That, after all, was the fate of a sissy in a female led marriage.
Darla
The waiter raised his eyebrows at me but said nothing and walked away. Mrs. Worthington-Smythe laughed at her comment. I wondered if he had heard Anna introduce me as Louis. The look he gave me made me think he did. It was one more reason to be embarrassed.
Anna’s mother was nice to me though she did question me on how it felt to wear girls’ clothing and if I liked it. (It felt weird and no, not especially). While waiting for dinner to be served Mrs. Worthington-Smythe took my hand and leaned over to whisper in my ear while placing her hand on my shoulder.
“You are a very brave young man to go out in public dressed like a little girl. You must be very comfortable with your masculinity”.
I smiled at her and nodded, though at that moment I was anything but comfortable.
Anna limited herself to the one beer but Mrs. Worthington-Smythe ordered more drinks and I was encouraged to drink several Shirley Temple’s. By the time dinner was finished I had to use the restroom. This was another embarrassing adventure as Mrs. Worthington-Smythe led me by the hand to the ladies’ room like a little girl. She walked me all the way to the stall door before reminding me to sit and wipe myself when I finished and also to repair my lip gloss before I left the ladies’ room.
When I got back Anna told her mom that we had to get going.
“It was nice meeting you Darla or should I say Louis…sorry. You just look so adorable in that pretty dress.”
“Umm..thank you ma’am,” I said.
“Oh and Anna remember to be respectful with your date, you know how to properly treat a lady,” Mrs. Worthington-Smythe giggled.
This was an awkward moment for me as Anna’s mom implied I was the fairer sex!
“Mom, you know I do,” Anna answered.
Suddenly I felt her hand squeeze my butt! I instinctively yelped at Anna’s grope, that it was hard to hide because Mrs. Worthington-Smythe must have noticed by the look of her sly smile!
I felt some relief when we finally left the restaurant, though I noticed the valet staring at me as I sat down in the car. This time I remembered not to display my panties. I wondered what ordeal awaited me at the dance.
The dance was in full swing when we got there and had to park a ways from the venue. The evening was cool and there was a breeze which caused my dress to lift and I found myself constantly pushing it down as we walked. I was a bit cold in the thin dress and was felt ambivalent when we finally entered the dance hall. It was warm there but I felt incredibly vulnerable.
Anna took my hand and led me to the dance floor. They were playing a fast number and we danced with minimum contact. Everyone was in costume and I saw several guys in skirts, though none of them were close to passable. I wondered if there were any that I could not detect who passed as girls. The band finally played a slow song and Anna immediately took the male role leading me around the dance floor. She took the opportunity to play with my ass and that along with the close contact we had was causing me some discomfort in my groin. Being in her arms, however, was the best I felt the whole night despite being treated as a girl and called Darla.
After a few more dances she led me off the floor and got me some punch. I was very thirsty by that time and finished the cup quickly. She got me another and asked if I had to use the ladies’ room. I declined, not wanting to go through that again. She gave me a quick kiss and told me to wait for her while she used it.
She had barely disappeared when a big man approached me. He was dressed in a 19th century suit and greeted me with a Southern accent.
“Howdy there little girl, mah name is Rhett Butler. And you are?”
He took off his hat and bowed to me.
“Darla, sir” I replied in a soft voice, hoping it would fool him.
“Nice to meet you Darla, I’ve been looking for Scarlett, but can’t seem to find her. Have you seen her?”
I shook my head indicating I hadn’t and hoped he would move on.
“Well, I guess she isn’t here then. May I have this dance?”
Without waiting for a replay he took my hand and led me to the dance floor. He put his right arm around my waist and pulled me close to him so our bodies were in close contact. I could feel his erection against my stomach and it frightened me. I tried to tell him I was waiting for my boyfriend, but he just pulled me tighter.
“Your boyfriend should know not to leave a pretty little thing like you alone.”
We danced several dances and I was sure his erection was growing. The idea that I was turning on a man was very unsettling and more than a little bit frightening. It became more frightening when his hand moved from my waist to my ass and he fondled it through my dress. It felt like he was lifting my dress. I tried to tell him to stop, but he ignored my pleas.
I wondered where Anna had disappeared to and for a brief moment I thought she had abandoned me there. All of a sudden she appeared and tapped him on the shoulder to cut in. I was afraid there would be a confrontation and she would get hurt.
“Thank you for taking care of my girlfriend” she said and smiled at him.
“The pleasure was mine” Rhett replied.
He released me to Anna and removing his hat he bowed and thanked me for the dance. Then he was gone. It was only then that I realized I was shaking.
Anna
Rhett is a friend of mine. He is bisexual and is especially attracted to feminine boys. He was happy to do me the favor of dancing and flirting with Louis. I learned later that he was disappointed that I had already claimed Louis. He would have liked a go at him. I observed the whole act where Louis could not see me and was very pleased at how girlish he acted.
“I’ve had enough” he said. “May we go home?”
The night was still young, but I had other plans for Darla and acceded to her request.
Darla
I was grateful that the evening would soon be over and I could get out of these little girl clothes. I loved being with Anna since that first time at lunch, but it had been a very stressful evening. I vowed to myself I would never dress up as a girl again. Oh how wrong I was.
I was not really paying attention to where she was driving and was a bit surprised to see her pull into an underground garage.
“Where are we?”
“This is where I live. You were such a good girl tonight that you deserve to be rewarded.”
She pulled into a parking spot and leaned over to kiss me. Then she got out of the car and walked around to the passenger side. After unbuckling my seat belt she held her hand out to help me from the car. We were the only ones in the garage so I played along.
“Why thank you, kind sir” I said. “That deserves its own reward.“
I put my arms around her neck and kissed her, plunging my tongue into her mouth. We played dueling tongues for a few moments when she pulled away.
“Let’s continue this upstairs” she said as she took my hand and led me to the elevator.
She punched in a code and we rode to the top floor. I was shocked when the door opened to the penthouse apartment which occupied the whole floor. It had a circular view of the whole city. I had no idea how much money she had but clearly she was very wealthy to afford this apartment.
“Would you like a drink? Something other than a Shirley Temple?” she laughed.
I nodded. She went to a wet bar and poured me a glass of white wine which I gratefully accepted. I needed something after the strenuous evening. She excused herself and said she would only be a couple of minutes.
True to her word she reappeared shortly. She had shed her Alfalfa outfit and reappeared in a diaphanous green nightgown and matching negligee. She was more beautiful than ever. She took my wine glass from me and extended her hand to help me stand.
“Come my sweet girl! It is time for your reward.”
It bothered me that she kept calling me a girl, but I said nothing, not wanting to destroy the mood. I thought that maybe she was going to go back on her promise to herself to wait for marriage. Of course, that made me more nervous. She led me to the master bedroom and what a bedroom it was. It had a round canopied king size bed, a vanity loaded with all kinds of makeup and perfume, a sitting area with a leather sofa, two leather arm chairs, and a glass top coffee table. It also had a gas fireplace which was already lit. Her walk in closet was bigger than my apartment and it was full of clothes. I was stunned when I saw it.
“Do you like?”
I merely nodded, too shocked to speak.
She removed her negligee, throwing it on the floor. Then she sat me down on the bed and kneeled in front of me. She removed my shoes and socks and pulled my panties down to my knees. The she pushed me onto my back and lay on top of me. She kissed me, her tongue invading my mouth. We hugged each other for several minutes, trading kisses. The tension of the evening left me.
She stood up and lifting my dress and slip she took hold of the tape holding my penis back between my legs.
“This may hurt a bit but you will be grateful we removed your pubic hair.”
She ripped the tape off and my cock sprung up to a full erection. She smiled at me and kissed it. Then she sucked me. It felt like she was drawing my semen out of my cock and it did not take me long to achieve my orgasm. It was the best orgasm I had ever had. She leaned over and kissed me passionately. In doing so she deposited my semen into my mouth. She ensured I got it all in my mouth by the way she pushed the salty thick goo with her tongue all inside my mouth and down my throat. I had no choice but to swallow my own seed. Then, she lifted herself up and positioned her pussy over my mouth.
“Eat me!” she commanded as she lowered her pussy into my mouth muffling my sounds.
The taste of her feminine sweat, warm wet secretions and her pubic hair was overwhelming for a guy like me. My mouth was not prepared for it. But giving her an orgasm made it all worthwhile.
I lost track of how many orgasms she had but by the time she rolled off me, my tongue and jaw were aching. By this time I was hard again so she used her hand to bring me off. Using her fingers she scooped up the semen from my stomach and chest and fed it to me. I did not particularly enjoy the taste but not wanting to break the mood I swallowed it in silence. She rolled me on my side facing away from her and wrapped her arms around me, spooning me. We fell asleep like that.
Anna
I had planned for him to be here without any clothes. It was my intent to keep him in skirts the whole weekend. Brunch at my mother’s the next day would just be the start.
Darla
When I awoke the sun was streaming into through the window. I smiled as I thought about our lovemaking last night and turned to reach for Anna. She was not there, but the flavor of her musky vagina was still very much in my mouth. Realizing I had to take a piss, I threw off the covers and immediately noticed that I had slept in my dress and slip. I was embarrassed to still be wearing girls’ clothes.
The urgency to pee was great so I moved quickly to the bathroom. Just as I got there Anna came out wrapped in a warm robe, her hair wrapped in a towel. She gave me a big smile and a peck on the cheek. I rushed passed her to the toilet and without thinking about it I picked up my skirts and sat on the toilet. I was in such a rush that I had not closed the door.
“Don’t forget to wipe yourself Darla”.
I blushed again at her words. I realized I had done a lot of that since yesterday, but I took her advice and wiped myself.
“There is a toothbrush for you on the counter and then I will help you remove your dress so you can bathe. We are invited to my mother’s house for brunch. She was really impressed with you last night.”
I thanked her and proceeded to brush my teeth. While she was unbuttoning my dress the realization hit me that I had no clothes at her apartment. I had gotten into my costume at my place and we had not gone back there.
“What am I going to wear? I don’t have any clothes here.”
“Don’t worry about it. I don’t doubt that I can find something that will fit you.”
I was worried. Surely she didn’t have any boys’ clothes. I hoped she had clothes that an ex boyfriend had left or that she could find a pair of jeans and a shirt that would fit and wouldn’t be too girly.
“I’ve drawn you a bath. I will lay out clothes for you.”
The bath had bubbles that smelled very flowery. If I had thought about it I might have considered the possibility that she was trying to feminize me, but instead I figuratively shrugged my shoulders and got into the bath. I had not taken a both in many years and it felt good to just sit there and enjoy the warmth and the sweet smell.
Anna
Of course I had clothes for him. He would not fit into mine so I bought him his own dress, shoes, and underwear. He really had no choice.
Darla
Her bath gel and shampoo had the same aroma as the bubbles and I could smell it on me when I got out of the tub. I wrapped the towel around my waist and nervously walked into the bedroom. Anna was wearing a white blouse with black Capri pants and even without makeup looked beautiful. She put her arms around my waist and gave me a long passionate kiss. While doing so she removed the towel leaving me naked and with an erection.
“We don’t have time for that” she said.
She grabbed some cream from her night table and masturbated me right there, catching my semen in the discarded towel.
“Much better” she said.
She handed me a three pack of panties and told me to put one of them on.
“ Before you say anything I have no boys’ underwear so you will have to wear some panties.”
The panties were yellow, pink, and lime green, all trimmed with lace.
“Don’t you have any that are a bit less feminine?”
“I‘m not giving you panties I have worn previously. These are all I have that haven’t been opened. Now pick out a pair and put them on!”
She seemed to be getting a bit angry with me, so rather than argue I picked out the green pair and slipped them on. I could feel the beginning of an erection. They were satin like the ones I had worn the previous evening and felt incredible against my skin. She disappeared from the room and returned with an ice cube. By the time she returned I had a full blown erection. Like the night before she put it on my cock and my erection shriveled. She took out a roll of tape, pulled my panties down to my knees and once again put it on my cock which caused it to shrivel. She then forced my balls up into my body and taped my penis back between my legs as she had done the night before. She held out a bra that matched my panties and ordered me to put my arms through the straps. I reasoned that she had no boys’ clothes in the house so I would have to wear girls’ clothes. I hoped she could make me look enough like a girl so no one would question it. Once we got back to my apartment I could change and go to her mother’s for brunch as a boy.
I turned around so she was able to hook it behind my back. Then she slipped some pads into the bra to give me the appearance of breasts.
“Turn around Darla!”
I wanted to protest her calling me Darla, but realized the futility of it when I was dressed as I was. I meekly turned around and she smiled.
“Very nice!” she smiled.
She handed me a yellow dress with a short flare and ordered me to put it on.
“Wait! What! Don’t you have pants I can wear?”
Anna
“I’m getting tired of your complaining Darla! If you like you can go home naked or in your cum stained dress from last night. It is your choice.”
I was purposely being harsh with her. It was important that she start obeying me without question. She needed to know, I’m the one wearing the pants in this relationship figuratively speaking of course.
Darla
I took the dress from her and slipped it on. It was sleeveless with a high neck and a short flared skirt. It had a thin cloth belt that tied around my waist in the front.
The only positive aspect of the dress was that it was longer than the one I had worn last night. At least I would not be displaying my panties. She handed me a pair of nude pantyhose and instructed me how to put them on. Somehow I manage to get them on without running them.
“I think you will be able to get into theses shoes. They may be a bit small, but they have an open toe. Otherwise you will have to wear the little girl shoes you wore last night.”
I wasn’t sure which would be worse. The shoes she gave me were white and had at least a 3 inch heel. I was able to slip them on and buckle them.
Anna
Of course the shoes fit. I bought them ½ size too small but they were sandals so I knew he could squeeze into them. I was thrilled with the way he looked in the dress. When I got finished with his makeup he would be a knockout.
Louis
She helped me to her vanity and proceeded to apply makeup. Unlike last night, she applied full make up since I was supposed to be a grown woman, not a little girl. Then she brushed out my hair and tied it in a high ponytail. She clipped on a pair of large hoop earrings and pronounced me ready.
“Alright Darla, stand up and let’s see how you walk in those heels.”
“Why are you still calling me Darla?”
“You sure don’t look like a Louis dressed like that, do you? Besides, wouldn’t you rather be taken for a girl rather than a boy in a dress?”
“Your mom knows I’m a boy.”
“Her maid doesn’t know that. I like you like this. Don’t you want to please me?”
I nodded, accepting my fate but hating myself for my fear of standing up to her. I tried to walk in the heels but almost fell on my face. Fortunately Anna was there to catch me. She showed me how to walk and had me practice while she did her own makeup. I followed her suggestion and while not terribly graceful, I managed to walk in them. With a bit of practice I developed a rhythm, which to my dismay included swinging my hips. I soon understood why women liked to remove their heels. I was walking in them for a short time and wanted to take them off.
“You seem to have the hang of it. Just remember to take small steps.” Anna said with a smile.
Then she gave me a peck on the cheek. Seeing her smile at me gave me a thrill that I felt in my whole body. I vowed to myself at that point that I would do whatever she requested to keep her smiling at me, even if it meant dressing like a girl for her on occasion. Had I seen the future I might have reconsidered that vow.
She gave me a white cardigan and a small white purse to carry and we left her apartment. I can’t explain how nervous I was going out in day light dressed like a girl. I prayed no one would ‘read’ me. At least she would be taking me home and I could change into male clothes.
Anna
I could see how nervous he was as we rode in the elevator. I grabbed his hand and smiled at him.
“Relax Darla! No one will be able to tell you’re a guy unless you give them a reason.”
The test was coming up. I knew he was assuming I would take him home to change before heading out to my mother’s, but that was not my plan. If he refused to go as is, that would end our relationship. It was not what I wanted, but if he were not willing to bend to my will I was not going to waste time on him. I would find another guy to train as a sissy.
Darla
We got in the car and Anna got on the highway. It took me a moment to realize that we were headed away from my apartment.
“Wait Anna! I want to change my clothes.”
“No time for that. Besides, the invitation was for Darla, not Louis” she grinned at me when she said that.
“No I can’t do this. It’s too humiliating.”
“There’s that word again. Do you still think it is humiliating to b a girl?”
“No..no of course not. But it is for a guy to be dressed like a girl.”
“Don’t worry! Mother has already seen you in a dress and I will be there with you.”
“Please Anna, take me home?”
“Alright, but if I do I will leave you there. It will be over between us. Do not try to contact me. If you can’t honor my mother’s graceful invitation than I’m not so sure you are right for me. She would not have invited you if she weren’t taken by you.”
“But I’m not a girl. I shouldn’t be wearing a dress! This is kind of going too far”
“There is nothing wrong with your wearing a dress any more than there is with my wearing pants. I do not want a stereotypical relationship, but if that is what you want, then it is better that we find out now. I will turn around at the next exit and take you home. I have had fun with you Louis, and I really like you, but if it is not meant to be….”
She left her thought unfinished, but I knew what she was saying. I asked myself if I could meet her mother dressed as I was. “What would her reaction be?” I wondered.
Anna
I really didn’t want to end it with Louis. I really thought at that time that I could feminize him completely but if I couldn’t get him to my mother’s house in skirts, then I didn’t see any choice. I was sure he loved me but I had to find out if he loved me enough to do this. I expected protests this morning from him. Now was the true test. I really hoped he would pass it.
Darla
I was stunned. I really didn’t think she would end it between us. That was definitely not what I wanted.
“You said the invitation from your mother was for Darla?”
“Yes. She was very clear that I was to bring Darla, not Louis.”
I took the compact out of my purse and looked at myself. I could see only vestiges of Louis. If I had a sister this is what she might look like. I sat there for a few moments trying to decide if I could go through with it. I felt the car slow down as she braked to exit the freeway and presumably turn around. I made a quick decision that I hoped I wouldn’t regret.
“Ok Anna. I will go with you to your mother’s as I am now.”
I was rewarded with a huge smile from her as she reached over with one hand and gently squeezed my thigh.
Anna
We passed the first hurdle. Of course, Louis could always back out once he learned how he was expected to live his life, but that was a problem for later. I could only take it one step at a time.
Darla
I was shocked when we arrived at his mother’s house. Calling it a house did not do it justice. It was a massive estate which I learned later covered 15 acres. The house alone was 3 stories with 12 bedrooms and 15 bathrooms. I expected that she was wealthy based on Anna’s condominium, but this exceeded any expectations I might have had.
The female security guard opened the gate as soon as she saw Anna’s car. I could not see the house from the gate but as we drove it appeared from the distance. According to Anna, it was ½ mile drive from the gate to the house. It was not a house, it was a mansion.
She pulled into a garage that must have held at least 10 cars, and it was almost full. She led me to an elevator that took us up to the next floor which was just inside the front doors are. She took me to a powder room where she fixed both her makeup and mine and stood there while I sat and relieved myself. It was embarrassing enough having to wear a dress, but to urinate sitting in front of her caused my cheeks to get redder than they already were from the blush.
As we entered the living room Mrs. Worthington-Smythe got up and gave me big hug. She took my hand and led me to a seat on the sofa next to her. She held onto my hands while we sat there. Anna sat in a chair opposite us. I felt very vulnerable without her at my side. There was one other woman there. She was introduced as Angela, Anna’s sister-in-law. I wondered where her brother was and prayed he wouldn’t show up and see me dressed like this.
Angela was about Anna’s age, a few years older than me. She was about my height with blue eyes and long read hair. She had a beautiful figure and was dressed in black pants and a white see-thru blouse under which she wore a white camisole. She was a very pretty girl, but, in my estimation, could not compare to Anna. She did give me a warm smile when we were introduced.
A cute girl dressed as a French maid brought me a glass of white wine. There was something off about her, but I couldn’t figure out what it was. My attention to her was interrupted by questions that Angela threw at me which were very direct and blunt. Some of them were:
• “What do you fantasize about?”
• “At what age did you start to masturbate?”
• “How often do you self-pleasure yourself?”
• “Honey, are you still pure?....you know a virgin?”
• “Have you ever had boyfriend or been with a boy in any sexual way?”
• “Do you believe that females are the stronger sex”
• “What do you think of a female led marriage?”
• “Should husbands be spanked when they commit naughty acts?”
I assumed that Angela thought I was a girlfriend of Anna’s and breathed a small sigh of relief. The questions were quite embarrassing. I really wasn’t sure how to answer most of them, but I tried to answer as I thought a girl would. I could not understand why she would ask me those questions when we had just met and vowed to myself to ask Anna later about them. I was grateful when we went into the dining room for lunch. It was served by the same uniformed maid.
It was late afternoon when Angela left and it was just Anna, her mother, and me. I was surprised when Angela took the maid with her. I would learn much later that the maid was actually Anna’s brother and Angela’s husband. As we were getting ready to leave Mrs. Worthington-Smythe once again hugged me and kissed each of my cheeks.
“Come back again, soon Darla”.
I was grateful to finally leave. As Anna opened the car door for me but before I got in she took me in her arms and hugged me. She gave me a passionate kiss. It was very reassuring to me but caused a great deal of discomfort in my groin.
As we headed back to town Anna told me that her mother was impressed with me. I remembered to ask her about the questions but she merely told me it was curiosity on Angela’s part and not to take them too seriously.
Anna
The day could not have gone any better. I was not ready to let him resume his male persona. I intended him to spend the night and the next day as Darla, reinforcing his feminization. He already was my sissy boyfriend and ultimately would be my sissy husband. I just wanted to move along the process.
Darla
When it became clear we were headed back to her condo I spoke up.
“Anna, can you take me home now?”
“I thought you would stay with me tonight. Wouldn’t you like a repeat performance of last night?”
“Well, of course I would, but I don’t have any clothes at your house. I thought we could stop at my place and I could get some, you know, boys clothes.”
“That won’t be necessary, DARLA. I like you dressed the way you are. Don’t you like being my girlfriend?”
“Well, I love being with you, but I am a guy you know.”
“For tonight you will be my girl, ok?”
Not wanting to spoil her mood, I reluctantly replied in the affirmative, realizing I would not be shedding girls clothing before the next morning.
Anna
This was too easy. I was sure that there would be a rebellion at some point but for now I was going to impress on him how much fun it would be for him to stay in skirts and dresses.
When we got back to my condo I undressed her down to her bra and panties. I freed her cock which immediately sprang to attention. I worked her over with my tongue. As I expected she didn’t last long before flooding my mouth with her semen. Once again I kissed her and fed her. her own semen. I hadn’t cum yet so I positioned myself over her mouth and had her eat me, giving me several orgasms, before collapsing on top of her. We kissed and I could taste the combination of both our juices and they were good. I realized that I was already thinking of him as a girl and that made me very happy.
We were both hungry, but we showered first where I had her lick me to two more orgasms before getting out of the shower. She was hard at that point so I gave her a hand job, catching her semen in my hand and feeding it to her. She seemed to be accepting that she would consume her own semen after any sex with me. Finally she was flaccid. I had to smile when I took out a pair of satin panties and handed them to her. Her cock immediately jumped to attention.
Darla
I didn’t particularly like the taste of my own cum, but Anna had been insistent and once again I yielded to her and consumed what she fed to me. I don’t think I realized at the time how subservient I had become to her. Whatever she wanted from me, I gave her until it was too late for me to become assertive.
It was terribly embarrassing for me to get hard when she handed me the panties. This was the third time it happened and I wondered what she really thought about my getting turned on by panties. It was a pink thong and unable to look her in the eyes I took it and slipped it on, tucking my cock back between my legs. When I looked up she was smiling. She then handed me a padded bra and watched while I struggled to get into it. Once I had it on she had me slip on a white mini dress that was several inches above my knees. It was linen with a square neck and elbow length sleeves. Assuming it was Anna’s, I thought that it must be quite sexy on her.
She dressed in a pair of white pants and a red blouse. We both wore white sandals, though hers were flat and mine had 2 inch heels, not terribly high but ultra feminine.
“I’m starving” she said “how about we order in pizza?”
I agreed immediately and she got on the phone to order it. While we waited she opened up a bottle of wine and we each enjoyed a glass while awaiting the pizza. She gave me $20 when the bell rang and told me to answer the door and pay the delivery guy. She clearly wanted to give me maximum public exposure while in my feminized state. I knew that arguing with her was not to my benefit, so reasoning that I would almost certainly not know the delivery guy and would be back in my normal boys’ clothes the next day, I took the money without protest.
Anna
I couldn’t stop staring at her during dinner. Even without makeup she looked like a girl. My plan was proceeding as I hoped and perhaps a bit faster than I expected. This next week would be critical. I had some surprises planned for her and it would be interesting to see her reaction to them.
Darla
Dinner was nice and we spent the evening watching some romantic comedy chick flick, though we spent more time kissing than watching. I dressed in a very feminine pink nightgown with matching panties. We were both exhausted but she did get on top of me and had me please her with my tongue. I was horny but she was too tired to bring me off and we fell asleep with her spooning me from behind.
Anna
I was not too tired to bring him off but it was a lesson for him. Because he brought me off was no reason for him to think I would return the favor. That was part of a female led relationship. And it was important to me that he learned that now.
Darla
Once again, I had an erection when she handed me a pair of panties the next morning. After taping my penis back between my legs, she had me put on the same dress I had worn the previous evening. She thought I looked very sexy in it. I had mixed emotions about that. Certainly I would rather be sexy for her in men’s clothes, but I did enjoy that she seemed to be unable to keep her hands off me. She dressed more gender neutral in trousers and shirt but did wear low heels.
Anna
I believe that pants are a symbol of power; skirts are more a symbol of passivity, especially short skirts. Her public appearances in skirts this weekend were not at an end. When I told her we were going out for a Sunday brunch I had to keep myself from laughing at the expression on her face. She was not happy about it. I briefly asked myself if I were pushing her too far too fast, but dismissed the thought.
Darla
I felt I had to put a stop to this. I could not understand why she wanted me dressed like a girl and wanted to take me out in public.
“Anna, I am not going out to brunch wearing a dress. I am a man, after all. Take me home so I can change my clothes. Then we can go out to brunch!”
She just stood there staring at me. I could not read her expression and it made me nervous. The longer the silence prevailed the more nervous I got.
“Well, I mean, um, w..wouldn’t you, I mean, why ..”.
“Stop!” she ordered me.
I shut up.
Ignoring my protest, she handed me a white purse that matched my shoes and grabbed her own bag. Then she took my hand and led me out the door. Not only had I succumbed to her demand, but even worse, I had tried to stand up for myself and failed. I clearly was not much of a man in her eyes or for that matter in my own eyes. I was close to tears as I thought about it, but somehow managed to hold them back. Meekly I followed her to the car and waited for her to open the door.
Anna
I expected his outburst and was content to see how far he would take it. When I finally raised my hand and ordered him to stop I knew I had won and he was mine. I was certain there would be no further protests.
Darla
Though I was very self conscious about my appearance, nothing happened at brunch or the walk we took downtown, browsing various stores. It was late afternoon when we returned to Anna’s condo. We both had schoolwork to do so she told me she would take me home. I kicked myself mentally for not picking up some men’s clothing while we were downtown. By this time the stores would be closed. I had no choice but to go home dressed as a girl.
Anna
From my perspective the weekend had worked out exactly as I had hoped. Though he didn’t know it, his days of wearing male clothing were numbered.
Darla
I was extremely nervous when she parked a block away from the building in which I lived. I prayed none of my neighbors would recognize me. When we walked into the building, Cindy and Rachel were waiting by the elevator. I thought I might have a heart attack.
“I loved the costumes you wore on Friday” Rachel said.
Anna thanked her and returned the compliment.
“Oh, I love your dress” Cindy told me. “Where did you get it?”
“I..I don’t remember” I said, knowing it was a lame response.
“Is that you, Louis?” she asked me and started to giggle.
I nodded, unable to speak. My worst nightmare had come true.
“Why are you dressed like a girl?”
“Because I told him to” Anna declared.
“Are you his mistress? Is he a sissy?”
“No. I am Anna, his girlfriend.”
“I’m Cindy, and this is Rachel.”
“Nice to meet you” said Anna.
“Likewise” both girls responded at once.
I stood there and said nothing. Fortunately the elevator arrived at that moment and we rode up in silence. As we reached my floor I couldn’t wait to get out of that elevator.
“Why don’t you come up to our place for a glass of wine?” asked Rachel suddenly.
That was the last thing I wanted to do but before I could respond, Anna accepted and grabbing my hand pulled me back into the elevator. The door closed before I could protest and my agony was to be prolonged.
Anna
Meeting the two women and having them recognize him was not fortuitous. It was meticulously planned by me. They knew full well what I planned for Louis. I thought it would be a great opportunity to further subjugate him and reinforce his place as my submissive girlfriend. The idea that these women who he passed in the hall frequently knew about him would only cause him more embarrassment.
Rachel and Cindy were both in their late 20s and owned a business for crossdressers. They provide a feminization service. Mother had given them seed money to start their business and they were always willing to help us. When I told them of my plans they both got excited and were happy to help me.
Darla
We were shown into their apartment and offered seats on the sofa in their living room.
“Would you like wine or something stronger?” asked Rachel looking at me.
“White wine please” I responded not being much of a drinker.
“Scotch, if you have it” said Anna.
“Ah, a girl after my own heart.” Rachel responded.
In a few minutes I sat there with my white wine while the other girls each had a glass of scotch. Did I say ‘other girls’? I meant the girls.
“So Louis..” Cindy started to say.
“When he is dressed like this I call him Darla.” Anna interrupted.
“Excuse me dear” said Cindy as she patted my knee. “How long have you been dressing like a girl Darla?
I tried to speak but no words would come out.
“Only since the dance on Friday night.” Anna responded for me.
“So why is he still dressed like a girl? And that isn’t the costume he wore to the dance” said Cindy.
“When she put on the panties I gave her on Friday, she got an instant erection. I assumed she liked wearing girls’ clothing so I kept her in them all weekend.”
“Wow! That is so cool” said Rachel. So you do like wearing girls’ clothing?”
“Nnnn,,,no, not really” I found my voice. I took a sip to calm my nerves.
“She is just too embarrassed to admit it. Each time she got dressed she got an erection when I showed her the panties she was to wear” said Anna.
I almost spit out my drink! If I could have died right then and it would have suited me just fine.
“Soooo, in that case you wouldn’t mind showing us your panties Darla?”
I shook my head no. There was no way I was going to show them my panties.
“I’ll show you mine if you show me yours” Cindy responded.
“I’ll show you mine also” said Rachel.
“How fun” said Anna. “Let’s all show our panties.”
Anna stood up and dropped her trousers showing her black lace bikinis. Then Cindy dropped her pants and proudly showed off her red lace g-string, followed by Rachel who lifted her skirt to display a light green thong.
“Like the view?” asked Rachel.
“Ok, now your turn” said Cindy with a sly smile.
I felt trapped and could see no way out of it so I lifted my dress, displaying the white panties I was wearing. They were far more lacy and feminine then any of the girls had on. Cindy and Rachel both oohed and aahed when they saw them.
“Give us a little twirl girl,” said Cindy.
I did as suggested, which produced wolf whistles from the girls.
“Oh yes, very nice,” smiled Cindy.
“Where is your cock?” asked Rachel. “Why isn’t there a bulge?”
“Oh, I taped it back between her legs. The bulge would be unsightly in her dress.” Anna replied for me. “Don’t you agree?”
“Of course! May we see?” asked Rachel.
“Darla, show them!” said Anna.
I looked at her and begged her with my eyes not to make me do that. She stared at me, silently ordering me to drop my panties. I didn’t think I could be more humiliated than I already was. I slowly removed my panties showing how my cock was taped back between my legs.
“Remove the tape!” ordered Anna.
Reasoning that I could not feel any more humiliated than I already felt I took off the tape and immediately realized how wrong I was. My cock sprung to attention in front of the three women.
“Oh my!” Rachel remarked “is that as big as she gets?”.
Her comment caused me even more embarrassment. I had never thought of myself as being small, but Rachel seemed to know what she was talking about. For a few moments, though it seemed like hours, the three women just stared at me as I stood there with my dress lifted and my cock as hard as it ever was. I tried to will it to go down, but nothing I could think of could force it into its flaccid state. Finally I excused myself to use the toilet just so I could get away from their stares.
I sat on the toilet willing myself to get soft so I could pee but it just would not happen. I thought of masturbating, but before I could do it I heard Anna calling me, asking if I were alright. Accepting that I was already as humiliated as I could be in front of these two women, I replied that I was, pulled up my panties, dropped my dress and holding my purse in front of the bulge I exited the bathroom.
Anna
Meeting Rachel and Cindy was going along exactly as I had planned. The meeting with them in their apartment was one more emasculating event for Louis, one that I welcomed. While he was in the bathroom I arranged for them to humiliate him even more. I hoped he would see being alone with me as a safe, though a feminine haven for him.
Darla
I had to hold my purse over the bulge caused by my cock while we made our way downstairs to my apartment. I was grateful when we finally were behind closed doors. I thought Anna would say something about what had transpired in the girls’ apartment, but all she did was give me a big kiss and tell me she would see me at school the next day.
It was a relief to finally shed the girls’ clothing I had been wearing for two days. I breathed a sigh of relief as I slipped on my boxers and tee shirt, my normal sleeping attire. I had felt so confined when I was dressed like a girl, especially from the bra and tucking my boy bits. I was disturbed how I reacted to putting on panties. Thinking about them gave me an erection and despite my attempts to will it to go away, I finally gave in and jerked off to an orgasm. That was enough to put me out for the night.
The next morning, I was eating a bowl of cereal in my tee shirt and boxer shorts when I heard a knock on the door. When I opened it, Cindy and Rachel barged in, each giving me peck on the cheek as they walked past me.
“Good morning Darla” they said in unison
“My name is Louis” I responded.
“Of course it is” said Rachel. “Here!”
She handed me a package in a brown paper bag.
“What is this?’
“Open it!”
Reluctantly I pulled the contents from the bag. It was a package of pastel colored nylon panties, bikini style.
“Why are you giving me these?”
“Because we want you to wear them” replied Cindy. “They are brand new and designer brand.”
“No!” I replied.
Rachel took out her phone and snapped a couple of pictures of me holding the panties. To my chagrin I had a boner which was clearly visible. She showed me the pictures she had just taken and others she had taken the previous day in their apartment. She showed me images of me in my dress holding my skirt up exposing my panties and also a few images without my panties.
“You wouldn’t want these shown around campus now, would you?”
“Wait! How did you get those?”
“You clearly had a little too much to drink that you don’t remember Cindy snapping a few with her phone?”
“Now, I’ll ask again. Do you want these shown around campus?”
I looked down at the floor and said “No”
“I didn’t think so. We expect you to be wearing them each day until we decide otherwise. We will be checking.”
I started to protest but she just pointed to her phone. I nodded, knowing my choices were limited and this was the best of a bad lot. They once again gave me a peck on my cheek and left me. With my appetite gone, I tossed my breakfast in the garbage and exchanged my boxers for a pair of the bikini panties they gave me. My boner had not left me so I jerked off. Fearing an erection at an inopportune time I tucked before pulling the panties up. Despite having seen it the whole weekend, the flat front was still very disconcerting to me.
Anna
I knew what Rachel and Cindy were going to do. It was I who gave them the package of panties. My original idea was to give them to him myself, but the idea of his being embarrassed by these two girls was too tempting. Also, I did not want to be the one blackmailing him. I needed to be his savior so he would become dependent on me. When I told them my plan they embraced it whole heartedly. We agreed that should he tell me about them I would act as if it were a surprise to me. What I was not planning on was falling in love with him. That would cause me to change direction, but only slightly.
Rachel and Cindy were lesbian man hating girls who loved to humiliate straight guys. They were both employed by my mother. While we weren’t close friends I had known them for quite some time and they were eager to help me feminize Louis when I asked them. They took a month to month rental on the apartment (which I paid for) and the plan was for them to leave after they had accomplished what I tasked them to do.
Louis
When I saw Rachel and Cindy that day they did not ask me to prove I was wearing the panties. I did not see Anna at lunch that day and called her when I got home. She was surprised at what the girls had done to me but advised me that it was in my best interests to comply. The next two days were the same. I saw the girls but they did not ask me to prove I was wearing the panties they had given me. When I talked to Anna that night, she surmised that they might not be checking and suggested that I could wear my boxers if I were brave enough. So on Thursday I wore my boxers. That was a big mistake because on that day Rachel cornered me and dragged me into the lady’s room where she ordered me to drop my pants and show her my panties. I had to confess that I was not wearing panties. She ordered me to come to their apartment at 7:00 that night.
“You have a choice to make Darla” Cindy told me when I entered their apartment.
“We can show the pictures we took around campus or you can help us out tomorrow night. We are having a party and you can serve drinks and munchies to our guests.”
That didn’t sound too bad but I knew there was a catch. So I asked the question.
She had an evil grin on her face when she answered.
“Rachel, show Darla what she will be wearing!” she laughed.
My heart sank when Rachel brought out the French maid dress they wanted me to wear.
I stared at it, knowing I would have to wear it in front of their guests.
“So what will it be Darla?”
“I’ll wear the dress for you” I responded softly.
“Good! Now strip!”
“What? Why?’
“So we can be sure it fits. Oh, and I do hope your wearing panties now” Rachel added “or there will be additional punishment.
I slowly removed my clothes, grateful I had thought to put on the panties before going to their apartment.
After I removed my pants she stared at the bulge in my panties. To my horror it grew. She giggled. Then she handed me a bra and told me to put it on. Without the breast forms it was empty.
You will need your breast forms for tomorrow night” she said.
I nodded. Then she handed me the dress and I slipped it on. Unfortunately for me it was a perfect fit. She gave me the package and told me I was to wear everything in it tomorrow and I was to show up at their apartment fully dressed at 3:00 to set up for the party.
I wanted to protest having to wear the maid’s dress while I went from my apartment to theirs, but was afraid of their reaction. So I merely nodded and started to take the dress off.
“What are you doing?” Cindy asked me.
“Changing back into my clothes so I can go home.”
“You can go as you are dressed” she replied.
“But, I can’t.”
“You don’t have a choice. Now go, we have things we need to do. Oh, and before you dress tomorrow be sure to shave your body. We don’t want our maid to have unsightly hair.”
Both girls laughed and then Rachel grabbed my arm and ushered me out of the apartment. Fortunately no one was around. I quickly tied my pony tail up high on my head to give me a more feminine appearance but had little hope I would be taken for a girl. I decided to take the stairs figuring that there was less chance of being seen. I managed to reach my floor without encountering anyone, but as I exited the stairwell I all but bumped into two guys. They both towered over me and were blocking my way.
“What have we here?” one of them said.
“A little fairy” the other one replied.
They were both laughing. I tried to go around them but they continued to block my path.
“Let us see your panties!” the first one said.
Before I could respond he grabbed my skirt and lifted it up displaying my lacy panties. I still had an erection which was clearly visible.
“She really gets off on this” the other boy replied.
“Please let me go?” I begged.
“Too bad I’m not gay or I would fuck her right here and now” one said.
The other guy nodded his agreement and they stood aside, letting me flee to my apartment. The encounter took its toll on me and when I was finally inside I broke down and cried. This was getting to be too much but I had no idea how to get out of it.
I had to call Anna and tell her I could not see her the next night, but as I was about to call her, she called me using a video chat. I considered not answering, being dressed as I was, but we hadn’t spoken since she said goodbye to me on Sunday. She would know I was home and I was afraid of angering her. I answered her call carefully positioning the camera so she would only see my head. Unfortunately, I had forgotten about the high ponytail and she picked up on it immediately. She suspected I was wearing feminine clothes and demanded to see how I was dressed. After exhausting all my excuses for not showing her, I positioned the phone on a book shelf and stepped back so she could see me in my entirety.
“Darla, where did you get that dress? You look darling in it.”
“It was not my idea. Cindy and Rachel made me wear it.
I then told Anna the whole story and that I would have to serve as a maid at their party the next night, so I wouldn’t be able to see her.
“It’s just as well. I have family business to tend to this weekend so I wouldn’t be able to see you anyway. I will see you at lunch on Monday. “Now you be a good girl Darla!” she laughed and blew me a kiss.
I was afraid to look in the bag the girls had given me but knew I needed to know the bad news. And it was bad. There were white thong panties, a black strapless bra, white knee high stockings and black pumps with about 5” heels. I tried to figure some way out of my predicament but nothing came to mind that wouldn’t result in further humiliation. I got very little sleep that night.
After school I barely had time to shower, shave and dress before meeting Rachel and Cindy at 3:00. I realized that wearing the thong was going to put my bare ass on display if I were not careful. Wearing the 5” heels was not going to help. It was disconcerting to me how feminine I looked even without makeup, especially with my hair up in a high pony tail. Still, I supposed it was better than being recognized as a guy
Rachel applied makeup when I got there while Cindy gave me a manicure and pedicure shaping my nails and applying bright red nail polish. The makeup was garish and actually made me look less feminine and more androgynous. The party guests would not know whether I was a male or female.
Then they put me to work cleaning the bathroom, the kitchen, and the living room. When I finished those chores I set out trays of food that had been delivered while I was cleaning the apartment. By 7:00 I was exhausted but still had the whole evening in front of me
As each of the guests arrived I opened the door, for them, dropped them a curtsy, and introduced myself as Darla, the maid for the evening. It soon became apparent to me that the party was an LGBTQ mixer. The guests were both men and women. Some of the men were quite femme and a few of the women were very butch. Carrying around trays of food was somewhat hazardous. I nearly dropped the tray several times when I felt my ass being pinched by both men and women. Wearing the thong meant that they were pinching flesh. One time I felt something sharp on my butt, like a needle or pin had been pressed against it. I turned to see a woman smiling at me.
“I’m sorry” she said “I think I got you with one of my nails.”
I looked at her nails and they didn’t look that sharp. I said nothing and soon forgot about them as I was pinched many more times. I finally did drop the tray towards the end of the party but fortunately it was almost empty. Rachel told me I would be punished for that. When I was finally able to check myself in the mirror after all the guests had left my ass had several black and blue blotches and looked like it had bled a little where I had been stabbed by that woman’s nail.
When everyone had left I was informed that I would stay the night and clean up in the morning. I suggested that I could just as easily sleep in my own apartment but was overruled. Their sofa opened up into a bed and I was given a blue chemise to wear without panties.
The girls came in the next morning and ordered me back into the clothes I had worn the night before. When I was dressed they told me to clean the apartment and they would inspect it when I was finished. Fortunately they were satisfied with my effort. Neither of them said anything to me about my punishment for dropping the tray and I prayed they would forget about it. It was not to be.
They escorted me back to my apartment. Before they left Rachel pulled out a package from a bag she was carrying and handed it to me. It contained several bras that appeared to match the panties they had given me earlier in the week.
“From now on you will wear a matching bra with your panties. No more boxers for you. Now where do you keep your boxers?” Rachel asked.
I tried to argue but Cindy put her hand up to stop me.
“One more word of protest and you will be wearing nylons and heels as well” she told me.
I turned, led them to my bedroom, and pointed to my underwear drawer. Rachel opened it and took out all my boxers and tee shirts and put them in the bag that had been holding my new bras.
“You won’t be needing tee shirts with a bra” she said. “Now where is your dirty laundry?”
I pulled out the laundry bag I kept in my closet.
“Dump it on the floor!”
“Now pick up your dirty underwear and put it in this bag!” she ordered after I had dumped it.
“Remember the video and the one I took last night” Cindy reminded me “and what will happen should we catch you without a bra and panties!”
She left the rest unsaid and then left me to consider my fate. It was all I could do to not break down and cry. I desperately wanted to talk to Anna, but she was unreachable this weekend. I was exhausted from the work they made me do, walking in the heels, and the stress of it all. I stripped out of my dress and underwear and took a nice hot shower. I was going to sleep but when I opened my underwear drawer I remembered that I had no boxers or tee shirts, which was my normal sleeping attire. I grabbed the first pair of panties and slipped them on. Once again I got an erection. I tried to ignore it but it wouldn’t go away. Finally I jerked off and was asleep in no time. I slept well that night and when I got dressed I threw on a pair of sweat pants and sweatshirt. I needed food so I went to a convenience store to get some bread, milk, and eggs. As I was entering my building Rachel and Cindy were coming out. I held the door for them and stood aside, but they came up to me and hugged me.
“You’re not wearing a bra!” Cindy declared.
“That’s too bad” said Rachel with an evil grin on her face.
“I’m sorry” I replied. “I was so hungry that I just threw on some clothes to get food.
“No excuses, Darla” she replied. “You could have thrown on a bra as well. Come with us!”
They each took a hand and led me to the elevator. We rode up to their floor and walked into their apartment.
“Remove your sweatshirt and lie down on the sofa!” Rachel ordered.
Cindy disappeared into the bedroom and returned with a box and small tube of what I would learn, to my chagrin, was an adhesive. She squeezed some of the adhesive onto my chest in circles around each of my male boobs. Then she removed a pair of realistic looking breasts from the box and placed them on my chest. She took each of my hands and placed them on the breasts and told me to hold them. I was not happy as I realized what they were doing, but was too afraid to protest.
After several minutes I was told to release them and stand up. They remained attached to my chest. I could feel the weight of them when I stood up and it was not comfortable. Looking down it appeared that I had breasts, big breasts. I would learn later that they required a C cup bra. I tried to pull them off but they were stuck on and it hurt when I pulled on them.
“They will not come off Darla, not without a solvent.” Rachel explained.
“Ok Darla, you can put on your shirt and go now. It is up to you whether or not you wear a bra.” Cindy added.
“Please, don’t leave me like this!” I begged.
“Good bye Darla!” they said in unison laughing as I exited their apartment.
Anna
Call me a bitch if you must but it was all going according to plan. The woman who stabbed Darla at the party had actually injected her with powerful female hormones in a time release capsule that would pump her full of the hormones for a year. That would cause irreversible damage to her ability to perform as a man. It would also cause her to develop nice breasts and a more feminine body. I had the girls apply the breasts to him since it would take a few months for the hormones to have any effect. They were a very high quality and quite expensive, but perfect for my plan. Admittedly there was a risk that he would blame me for feminizing him in the first place, but it was a risk I had to take. So far everything was working as planned.
Louis
I tried to pull them off but that wouldn’t work. I tried alcohol but that also failed to remove them. I had no other ideas. Was I really stuck with them? In any case I had to relieve the pressure and with great reluctance put on a bra. The relief was instant. I realized I would have to wear a bra to support my new additions until I was able to figure a way to remove them.
Sometime late afternoon there was a knock on my door. I was going to ignore it thinking it was my tormentors, but heard Anna calling for me to open the door. I wasn’t sure I could even face her but she was really my only friend. I opened the door and she came up to me. She took one look at my chest and hugged me. It felt good to be in her arms again.
“So why are you padding your bra, in fact why are you wearing a bra, not that I mind, but I thought you didn’t want to look like a girl?”
“It was those two bitches” I said. “They attached these breast forms with glue and I can’t remove them. I don’t know what I am going to do.”
“Oh sweetie, I am so sorry. I feel like this is my fault.”
“It is those two bitches who are at fault” I said dissuading her from taking the blame. “What am I going to do now? I can’t bear to face anyone at school.”
“Let’s sit and think about it. There has to be some way around this” she said.
She sat on my sofa and pulled me onto her lap. I know she should have been on my lap but at the moment I wasn’t feeling very masculine so I didn’t protest. Also, as always, it felt good to be that close to her. She pulled my head back against her shoulder and told me to lay there and relax.
Anna
I was happy that he absolved me from blame. That was the big risk with my plan though I thought I could talk him out of it if it came to that. Now I had to let him think I was attempting to come up with a solution. In fact I knew exactly what I was going to suggest.
Louis
I don’t know how long we sat on the sofa with me on her lap. All I knew was that the sun had gone down and it was dark outside.
“Louis, I’m hungry. Do you have any food in the house or shall I call for takeout?”
“There are eggs, bread, and milk. I think that is all.”
I was shocked when she easily lifted me off her lap and sat me next to her. I had not realized how strong she was. She certainly didn’t have bulging muscles.
“Sit there Louis and I will cook the eggs and toast the bread. Do you have coffee?”
I waved my hand toward the pantry with the coffee and sat there while she cooked us the food. I really did not have an appetite but I ate anyway. We sat there finishing our coffee and once again I started crying. Anna stared at me but did not move.
“Ok, this is not getting us anywhere” she stated. “Let’s brainstorm and see if we can come up with a solution.
I could think of nothing as had been the case the whole afternoon.
“What if you pretend you‘re transitioning and go to school as a female?”
“No! I couldn’t do that.”
We sat there for awhile without talking.
“I guess I will have to drop out of school but I don’t know what I will live on. I will lose my scholarship if I drop out.”
“You could get a job and go back next fall. I am sure we will be able to remove those breasts by then. They will probably fall off on their own.”
“Get a job? With these?” I said grabbing my faux breasts.
“You could get a job as a girl.”
“NO I’m not going to live as a girl. I am a guy, you know.” I replied and again started crying.
Anna
I expected his reaction. Now it was time for some tough love.
“There is no way you can hide those breasts. So your choice is either to live as a girl or subject yourself to the derision you will receive as a guy with breasts. I can’t make that decision for you.”
I grabbed my jacket and put it on.
“Are you leaving?”
“Yes, I have some studying to do. I will talk to you tomorrow. I hope you will have made a decision by then.”
I gave him a peck on the cheek and left.
Louis
I barely slept that night. I had no idea what to do and the idea of living and working as a girl was not what I wanted. I finally decided to go up to the girls’ apartment and reason with them, beg if I must to have them remove the faux breasts. I rang the bell and knocked on the door but there was no answer. I gave up and went back to my apartment. I tried to contact Anna but she was not answering her phone. I could not think of any satisfactory solution which only caused more tears. I went up to the girls’ apartment several times that day but no one answered the door. It was late afternoon when I ran into the superintendent. He could not hold back his laughter when he saw the protrusions on my chest. He told me that the girls had moved out and left no forwarding address. Now I was royally screwed.
Anna
I purposely did not answer his calls. Of course I knew the girls had left. That, after all, was the plan. I wanted him to be even more desperate than he already was. It was early evening before I went to his apartment.
“So Darla, have you thought of another solution?”
“No” he whispered so softly I could barely hear him.”
“Well then, you have a choice. Live as a girl or tolerate the teasing. Make a decision! I will not tolerate your moping around. You easily pass as a girl, a very pretty one I might add, and can do this. You can live with me rent free.”
Louis - Darla
Reluctantly I nodded my head.
“I will drop out for the semester and hope they let me continue whenever theses breasts come off. In the meantime I will live as a girl.”
“First you need to bathe. You smell like you haven’t bathed in days. While you’re at it, remove all your body hair!”
I nodded and followed her instructions. When I came out of the shower there were female clothes I hadn’t seen before laid out on my bed. Before I could question her she told me that she brought them with her in case I agreed to go along with her plan.
She sat on a chair in my bedroom watching me done the girlie clothes. As I put on the panties little Louis, or should I say little Darla once again betrayed me. Anna told me to ‘take care of it’ and I was forced to masturbate in front of her. Feeling as low as I did I was unable to protest and at the time it hadn’t occurred to me that I was just following her orders.
When I was done ‘taking care of it’ as she put it, I tucked and put on the matching bra that Cindy and Rachel had left me. Then I put on the clothes that Anna had brought which consisted of nude pantyhose, a short A-line denim skirt, a white peasant blouse, and blue wedge sandals with 3 inch heels. She helped me with my hair and makeup, added clip on earrings, a necklace with a small gold heart, and a bracelet and pronounced me ready to go.
“Where to?” I asked.
“Tell your landlord you are giving him your 30 days notice.”
“What about my clothes?”
“Leave all your male clothing here and just take the panties and bras the girls left you and any other female clothes you may have here. We will go back to my apartment. You won’t need anything else. Tomorrow we will get you a new wardrobe.”
I was too rattled to put up any argument. I left the apartment with Anna, not realizing I would not wear pants again. The next morning I dressed in the same clothes I had worn when we left my apartment.
“First we will go to the diner and get some breakfast”.
She held up her hand to forestall any argument on my part. At the diner the waiter took me for girl and flirted with both of us. It made me a bit uncomfortable but also buoyed my confidence that I could indeed pass as a girl. After breakfast, she drove me to the university and pulled into the parking lot.
“Why are we here?” I asked her.
“Go see the dean and tell him you’re dropping out!”
“I can’t go to see him dressed like this.”
The look she gave me was enough to force me out of the car. I heard the lock click and knew I had to follow through or I would be left there. I pulled myself together and told myself I could do this. Remembering all I knew about acting as a girl I slowly walked to the dean’s office and prayed that he would see me.
The dean looked shocked when I walked into his office for which I could not blame him. I told him that I was confused about my gender and needed time to think about it. I said that I wanted to drop out for a time while I considered my options and that I planned on living as a girl to see if that was what I really wanted.
He was very kind about it but told me he could not guarantee my scholarship when I was ready to return. I left him even more depressed to return to Anna who was waiting in the car. I was not paying attention to how I got in and Anna giggled.
“What’s so funny?”
“I believe you flashed your panties to those guys over there” she said.
I looked over and sure enough there were three guys staring right at me with smiles on their faces. I could feel myself blushing and hoped they didn’t see more than my panties.
We headed to a mall where we spent more money than I had on all sorts of girls’ clothing. Anna loaned me the money for our purchases which meant I was in her debt. We bought dresses, skirts, tops, lingerie, and shoes. Anna convinced me to pierce my ears noting that many guys had pierced ears and the holes would fill in over time if I decided I didn’t like it when I returned to being a guy. We had to make several trips to the car to put all the packages away. Our last stop was for cosmetics where I had a professional makeover and spent another small fortune. It also meant, I thought, that she loved me or why would she have done that. We went to her condo and put all my clothes in her spare bedroom.
Anna
For the next couple of weeks, except for my going to class, we pretty much stayed home. I gave Darla a list of chores for her to do each day, training her to be my wife. Of course, she did not realize that that was the goal. She was handling the chores well, though she was still unhappy at having to live as a girl. For a couple of weeks she complained about the length of her skirts and dresses, but as I told her, it turned me on. Every so often she would ask me if she could get a pair of trousers even if they were women’s. I asked her if she liked turning me on. When she said she did, she dropped the subject of wearing pants.
Darla
My wearing short skirts turned Anna on, but we still had not had intercourse. She would masturbate me or occasionally give me a blow job, but always fed me my own semen. I began to wonder if I were sick accepting her domination. At the time I could see no other option. I was totally dependent on Anna and of course, I was madly in love with her.
I was living with her for about 6 months when my breasts started itching and were very sore. With the breast forms on I could do nothing about it and it was driving me insane. Then one morning I noticed that one of them was loose. I was able to pry it off. I was ecstatic thinking I could return to living as a man. I started rubbing the breast and stopped. Something was clearly wrong. It was quite a bit bigger than it had been before the two bitches put the breast forms on me. I then went to work on the second form and found that with a little bit of pain I could pry that one off as well. It too was bigger. My breasts were like those of a teenage girl going through puberty and I burst out in tears. Only Anna’s promise to take me to a doctor kept me from totally losing out.
Anna
With the breast forms off I wanted to show her how delightful it felt to have someone play with her breasts. I incorporated kissing, sucking, and playing with her breasts into our love making.
Something else was happening to me. My plans had been to turn her into my sissy slave husband, but I found that it was becoming distasteful to me. I was actually in love with Darla, and while I still wanted her feminine and subservient, I did not want her to be a slave. I wanted her to be my passive partner under her own free will. I could not undo her feminization that was taking place, nor, to be perfectly honest, did I want to, but I did not have to nor was I going to humiliate her any longer.
Darla
While I couldn’t get hard enough to even attempt intercourse, assuming that Anna would allow it, I was able to get somewhat erect and I did just that from Anna’s manipulations of my breasts. The first time she sucked on my nipples I thought I was going to cum right then. I never imagined how good it could feel to have such sensitive breasts.
Anna
I noticed over the next couple of weeks her inability to get very hard when she did get an erection. It was what I was aiming for. It was now time to introduce her to a new way of achieving an orgasm. I introduced her to ass play. She shrieked softy the first time I put a finger in her, but she started gyrating on the bed and soon had a soft erection. Similarly, she moaned and moved about when I sucked or caressed her nipples. She was responding like a girl in bed.
Darla
I became increasingly despondent over my apparent inability to get a real erection and the increased sensitivity in my breasts. I was certain they were getting bigger. I was surprised at how sensitive my ass was and how good it felt when Anna played with it. It made me forget for a little while my inability to respond the way a man should.
A few days later we went to a gynecologist Anna knew. Dr. Natalie Monroe was a medical doctor specializing in women’s health..
“Be a good girl okay? Darla,” said Anna as the nurse led me to the medical room. I waited for a few minutes before a lady in her mid 40’s entered the room.
“Louis is it?” she said looking over my medical chart. “I understand you are having some personal health problems?”
“Yes.”
“Say no more, we are going to get to the bottom of this. Please take everything off including underwear and have this gown on when I come back.”
She left giving me the privacy to change. I removed my clothes and put on the thin gown.
“Please lay on the bed Louis, and try to relax,” she said.
She adjusted the bed causing me to lay flat and then pulling up my legs on these metal stirrups that held them up in the air. She then pulled the stirrup leg holders apart in a way where my legs were now in a wide V.
“I’m going administer a pelvic exam now, it is important that you stay still,” she said while putting on some latex gloves.
She felt my testicles with her gloved hand and then stroked my penis a bit.
“Hmmm..looks like the testes and the penis are below average size,” she said. “By the looks of the head of the penis, it looks like you have had little or no sexual intercourse. This is good as it helps narrow the cause of your problem.”
“Ahh..” I moaned.
“I’m now going to have to perform a rectal exam. To test out if your penis has any function other than urination. You may experience some discomfort” she smiled.
She got up and adjusted her glasses and began coating her index finger and middle finger with a lubricant.
Anna
“So what did the doctor do, Darla?” I asked on the way back home.
“She examined me, took blood and urine samples. She said she would get back to me when she had the results.”
Darla
What I didn’t tell Anna was that along with a very embarrassing rectal exam, Dr. Monroe had me produce a semen sample. She was pressed for time, so in order to get a pure sample she inserted her gloved finger deep inside my butt so she could stimulate my prostate gland. It was equally embarrassing for me having orgasm right in front of her. I wanted the earth to swallow me right there.
Anna
The doctor I took Darla to had lost her license for having sex with one of her patients. She was in mother’s employ and would do whatever mother and I asked her to do, that being that Darla was not to regain her masculinity.
Darla
I waited nervously for a week until the doctor called. She requested that I come in to see her to discuss the results of the tests. There we learned I had an excess of female hormones in my body. There was nothing she could do about that other than help me adjust to it.
Anna
I hated doing this to Louis. By now I realized I really did love him, but the only way I could be with him was by making him my submissive, feminine wife who I would love and cherish and take care of forever. The hormones would destroy her ability to have intercourse, at least in the normal way. I knew she would be depressed so I chose this time to propose to her. I had little doubt she would accept the proposal.
I chose the beach as the place to propose to her. While walking along the beach shore with Darla in her yellow dress and sexy white sandals. She looked very pretty. We walked holding hands when I stopped her and told her to get on one knee. She was perplexed, but did as she was told.
“Louis Smith, get on one knee now,” I ordered in a soft but firm tone. “We have only known each other for several months, but in that time I have come to love you.”
I then took out the diamond box and opened it. Her eyes opened wide.
“Will you marry me?”
“Umm…yes…yes!”
With that I slid the diamond ring into his finger sealing the deal.
Darla
I was in heaven when she asked me to marry her. She told me to hold my hand out and without thinking I did and watched her slide a ring onto my finger. It was beautiful and quite feminine.
I tried to argue with her that I should be giving her a ring, but she countered that since she had money and I didn’t, she was giving me one. She conceded that when I had money she would accept a ring from me. I was too afraid to protest about how feminine the ring was, but decided that as long as I was living as a girl I would wear it.
Anna
It went exactly how I planned. We called my mother (who knew in advance I was going to ask her to marry me) and told her the good news.
“Did you get on one knee?” was the only question mother asked me.
“Hell no,” I said.
“That’s my girl.”
She invited us for dinner that night.
Darla
Anna chose my outfit for me which consisted of white satin panties, a matching bra, nude nylon stockings, a garter belt, a red dress with white flowers, and a pair of pumps that matched the dress with 3 inch heels The dress was several inches above my knees, as were most of the dresses and skirts I bought, and I knew I would have to be careful not to flash my panties. It would be impossible for me not to display my stocking tops and garter straps.
Her mother greeted me warmly and hugged me tightly.
“I’m so glad you came Darla!” she gushed. “Now let me look at your ring!”
She gushed over that as well. Then putting her arm around my shoulder and led me to the living room ignoring Anna who was standing there in the entry hall. I glanced back at her and saw a big smile on her face. Clearly she was enjoying my discomfort.
Anna
Of course this had all been planned. Mother liked Darla from the first night she met her and was hoping that she would become my wife. Really, between my mother and me Darla had little chance.
Darla
“Will you call me mama now? Please, it would make me so happy.”
“Yes, of course, Mrs. Worth… I mean mama.”
She gave another hug and kissed me on my cheek. She sat me down on the loveseat and plopped down next to me. Then she took my hands and held them on her lap.
“So, have you decided on a date for the wedding?” mama asked me.
“Anna wants it to be as soon as possible so we were thinking about the middle of next month.”
“That is soon. We can have it here if that is acceptable to you and I know a great caterer.”
“That would be great, but we kind of wanted a small wedding. I don’t really have anyone to invite. I hope you don’t mind.”
“Of course not. But we do need to see if my wedding dress will fit you. It was originally my grandmother’s. My mother wore it and I wore it. You and I are about the same size so if there are any alterations needed, we can get them done.”
“But wouldn’t you want Anna to wear it?
“Of course I would, but she has refused and frankly it would be too small on her and it is a bit frou-frou. Have you seen Anna wearing anything like that?”
“No, I guess I haven’t. Even though I have to dress like a girl for awhile, I really am a guy. I don’t think I will be wearing a dress for the wedding.”
“No, of course not. How silly of me. But will you at least agree to try it on? For me? It would make me so happy to see one of you wearing it even if it is just for a little while.”
She had tears in her eyes when she said that and I could feel the tears welling up in my eyes. She was being so loving and kind to me that I didn’t have the heart to say no. I nodded, afraid to speak lest I might cry. She gave me a big hug and held me for at least a minute.
“Oh Darla, you are making me so happy. Suppose you come back tomorrow and try the dress on. How does that sound?”
I nodded again. I wondered what I was getting myself into but I did not have the heart to say no.
Having grown up in a series of foster homes I had never felt the love and affection I was receiving from her. It was a different and amazing feeling. I wanted to cry thinking about all I had missed as a child. I briefly wondered if she would be giving me the same love and affection if I weren’t posing as a girl. I quickly dismissed the thought. I did not want to think that way.
Dinner was lovely, served by the same maid who I had met the first time I was at the house. We had coffee and dessert in the living room where Angela joined us. She too gushed over my ring and hugged me tightly. She told me how happy she was that I was marrying Anna. I still did not know if she was aware that I was a man, well maybe not really a man but certainly male.
It was late when we finally left. Before opening the door of the car for me Anna asked me if I had enjoyed the evening. As she turned towards me the emotion that had been bottled up the whole evening came to the surface and tears began to flow. She wrapped me in her arms and hugged me tightly.
“What’s wrong Darla?”
I shook my head to indicate nothing as I was too emotional to speak. Finally, I got myself under control, though the tears still leaked from my eyes.
“Aside from what I get from you, I have never felt the kind of love I received from your mother and even Angela.”
Anna
Darla’s reaction proved that the evening had gone as planned. The next step would be the wedding dress. That was my mother’s bailiwick and she would be the one to convince Darla that she would be wearing the wedding dress while I opted for a tuxedo, cut for a woman of course.
I acted surprised when Darla asked me if I would take her to my mother’s the next afternoon. I told her I would pick up her up a few hours later.
Darla
I was very nervous about trying on the wedding dress and asked myself why I had agreed to it. It was bad enough dressing like girl every day but there was no way I wanted to wear a wedding dress, not even just to try it on. I had committed to do so against my better judgment so I was not going to back out now and hurt the only person who ever acted like a mother towards me.
I wore a simple black miniskirt and a white tank top. Anna dropped me off at 1:30 and told me she would pick me up at about 4:30 after her meeting with her faculty advisor was over.
I rang the doorbell and it was answered almost immediately by mama. She gave me a big hug and I could feel the warmth generating from her. It made me almost glad that I had agreed to try on the dress. What I hadn’t realized was I would be trying on more than just the dress. She wanted me to wear everything she wore as a bride.
She took my hand and led me upstairs to her bedroom. I saw a garment bag hanging on a hook on the door to her closet, presumably containing the dress.
She asked me to remove my clothes. I was embarrassed about stripping in front of her but I slipped off my shoes and turned my back to her as I removed my skirt and top.
“Everything sweetheart, there is special underwear that a bride wears and you will experience that thrill, even if it is only in this room today.”
I hesitated, not wanting to be naked in front of her. Seeing that, she handed me a pair of panties and told me to put them on and then we could proceed. She turned her back to me so as not to see me naked. I removed my bra and the panties I was wearing, and stepped into a pair of white silk bikini panties with lace on the waist and legs and a pink bow at the waist. They were beautiful and I was erect before I even pulled them. I had gotten used to tucking myself before putting on panties but even though I was not very hard there was no way for me to tuck now.
“May I turn around now sweetheart?” she asked me.
“Not yet, mama. I need to use the bathroom.”
I ran off to her bathroom and jerked off, being careful not to get any of my semen on the panties. When I was soft again I was able to tuck. I returned to the bedroom and saw her grinning at me. I wondered if she knew what I had done and it made me blush, but she said nothing. She was holding a white corset which I learned was made of silk with metal stays. It hooked in the front and laced in the back and mama laced it as tight as it would go, ignoring my protests that it was too tight.
“Sometimes a girl has to suffer a bit to look pretty for her lover” was all she said when I protested.
She told me to take shallow breaths and after a few minutes I was breathing easier. She gave me white nylon stockings which I slipped on and attached them to the garters. Despite having just cum a few minutes earlier the feel of the nylons and the tugging of the garters against my legs was causing me to get excited again and the panties were not tight enough to hold back my erection. I could not have been more embarrassed, but mama took it in stride. She went to her dresser and pulled out a white panty girdle.
“Here, put this on under your panties and tuck. That should hold you” she told me.
“Umm.. can I use the restroom?”
“Sure darling,” she said with a smile. “Oh and darling it’s okay to feel the way you are feeling right now.”
What I felt was total humiliation, as I went to the bathroom, jerked off again, and followed her instructions. When I returned to the bedroom I looked like any girl down there.
I watched as mama opened the garment bag and took out the dress. She held it up and asked me what I thought of it.
“Oh mama, it is beautiful! You must have been a beautiful bride”.
She smiled at me but did not respond.
“First the petticoats” she said.
There were two of them laying on the bed. She held the first for me to step into, pulled it up to my waist, and tied it in the back. The she repeated the process with the second one.
“Now for the shoes.”
They were white sandals with 3 inch heels and multiple straps covered with rhinestones. I sat on the bed, being careful not to wrinkle my petticoats while mama knelt on the floor in front of me. She slipped each sandal onto my feet and buckled the straps for me.
“Alright! Now are you ready for the piece de resistance” she said as she held the dress.
I nodded, unable to speak. I did not understand the emotions flooding through me. I had been turned on by wearing the bridal underwear and now I could feel myself unsuccessfully struggling to get hard again at the prospect of wearing the dress. I was a guy after all, and yet, at that moment, there was nothing I wanted more than to wear that dress.
She unzipped it and held it up so I could put it on over my head. I slipped my arms into the sleeves and mama lowered the dress onto me. She turned me around and zipped it up. Even with the corset reducing my waist the dress was a tight fit. The realization that mama had worn this dress for her wedding, and before that her mother and grandmother, brought tears to my eyes. That mama thought so much of me that she would allow me to wear it was too much for me to process at that moment.
I looked at mama and saw that she too was crying.
“Mama, what’s wrong?”
She smiled through her tears.
“Nothing sweetheart, nothing at all. It is just that you are far more beautiful than I would have ever imagined. Come look at yourself in the mirror.”
I realized that I had been so caught up in the emotions of wearing the dress I had neglected to see how I looked in it. To say I was stunned was an understatement. I moved my arms just to be sure I was looking at an image of myself. I turned to mama.
“This can’t be. I’m a man. I can’t look like this” I protested.
“And yet the mirror doesn’t lie, does it?”
She hugged me tightly and I responded in kind.
“Darla, sweetheart, it is ok for you to say no, but would you reconsider wearing this for your wedding?”
Caught up in the emotions I was feeling and seeing how mama was acting, I could not say no. I agreed to wear her wedding dress for the wedding. Later I would wonder how and why I had agreed to it, but it would be too late. I would be a bride at my wedding with Anna.
Time seemed to speed up as we looked forward to our wedding and was now only a week away. What was disturbing was seeing the buildup of my trousseau. I had not seen so much ultra feminine lingerie, skirts, dresses, sweaters, and blouses. I could see that my intention of being Anna’s husband was being ignored and my ability to do anything about it rapidly fading away.
Anna
I can’t say that I didn’t feel a bit guilty over what I was doing to Darla, but I felt strongly that she would adapt and be happy. I had seen a similar situation with my brother Avery and mother told me that my father was transformed in much the same way as Darla. Both of them however were/are sissy slaves. I had no intention of making Darla my slave.
Darla
The last few days before the wedding were hectic, but mama did her best to shield me from all the chaos. She brought in a beautician on the morning of the wedding to do my hair and makeup. Mama helped me dress and was going to walk me down the aisle. It was a shock to me to find out that Avery, the maid who had waited on us the whenever I was at the house was, in fact, Anna’s feminized brother and Angela’s wife. Avery was my matron of honor. Angela, who like Anna, wore a tuxedo, was Anna’s Best Woman.
“You look very nervous honey,” said Mama.
“A little. I just thought I would never find love or get married….especially not like this,” I said.
“It’s ok darling, I was also nervous on my wedding day. I think that most brides are”.
She caressed my face with her soft hand while her eyes locked with mine.
"You look so nervous and vulnerable dear, but absolutely beautiful in that dress, I can see why my Anna chose you to be her wife," she smiled.
I relaxed a bit with Mama's words. She looked at me and lightly bit her lip.
Mama moved closer and with both hands firmly holding my head she leaned in and kissed me fully on my lips!
"Mmmmpphhhh!"
My eyes widened with sheer shock as Mama's mouth pressed against my mouth.
One of her hands moved downward feeling my waist until she reached my derrière! Gripping tightly my butt while her other hand pressed against my chest, feeling it out.
Her mouth opened mine feeding her tongue into me, I could only stand there as I was being fully groped and french kissed by my soon to be Mother in Law!
"Mmmmm..mmm…" she moaned into my mouth.
As I attempted to break away, she moved her hands back to prevent me from escaping her.
Holding my head tight, her tongue invaded my mouth! Exploring every crevice and mixing our fluids. Mother was not content until she was practically down my throat!
"Mmm…you will make a fine young wife for my lovely daughter, Darla," she said after finally letting me go, looking me down smiling in approval.
"I'll see you at the ceremony darling" she said while fixing herself up looking at the mirror acting as if nothing just happened.
"A pity we can't share you," she winked as she walked out the door.
Anna
I was looking in the mirror making the final touches to my hair when mother walked in the room.
"Mama, how is Darla doing?"
"Oh, she was a little nervous…naturally, but I got her under control," she said with a sly smile.
Darla
The wedding was to be held outside in Mama’s large garden estate. The wedding ceremony was not exactly that…well it was not what I thought it would be. She had a Priestess preside over the ceremony. I didn’t know what faith this was, but I followed what Anna and her family asked of me. I was determined that my wedding to Anna was going to be the best thing that ever happened to me and I was not going to let the fact that I was to be the bride deter me from making it a very happy day. When I walked down the aisle on mama’s arm I did so with my head held high. I knew I was a pretty bride and that I looked every inch a woman. My package was tucked back between my legs and would not surface until the wedding night in our room. Mama gave me small quick glances as we walked. She seemed very happy and had tears in her eyes as we walked down the aisle. I realized I wasn’t just marrying Anna, but I was also getting the mother I never had. It was all I could do not to cry.
Anna
Darla looked absolutely exquisite. She was the most feminine thing I had seen with her flower headband, veil and lace gloves. Soon she would take the oath to be my lawfully wedded wife.
Darla
I was in a trance during the ceremony and it was only later that I realized my vows included obeying my wife or was it my husband? It was not a big wedding and to my surprise all the wedding guests were female, or at least presented as females. There was a small line of the lady guests who wanted to dance with the bride, i.e. me. Fortunately I did manage several dances with Anna and feeling her strong arms around me made me feel safe and secure.
Anna
She felt so fragile and delicate in my arms. Darla was the total embodiment of femininity, I felt so lucky to have her as my wife now.
Darla
I was grateful when the party was over. The chauffer drove us to the hotel where we would be spending our wedding night. On the way there Anna held me tightly, French kissing me as we made our way to the hotel. The honeymoon would have to wait until the school year ended for Anna. I was not prepared for what Anna planned for our first night as man and wife, or is it woman and wife. I am so confused.
The bellhop showed us to our room. We had 2 small suitcases since we were staying only one night. He opened the door and stepped aside so we could go into the room. I was surprised when Anna easily lifted me into her arms and carried me over the threshold. She gave me a long passionate kiss in front of the bellhop before setting me down and giving him a generous tip.
After the bellhop left Anna wrapped her arms around me and once again gave me long kiss. I felt like I could stay like that forever. All thoughts of my being the man were out of my head. I felt truly happy, probably for the first time in my life. I accepted that I could be happy being a girl for my new spouse. When the kiss broke, with her arms still around me I felt her slowly take the zipper of my dress down and let it fall to the floor. Then she lifted me up out of the dress and set me aside.
“Mother will have my head if we tear her dress” Anna said with a laugh.
Then she untied each petticoat in turn and let them all to the floor. Taking my hand she helped me keep my balance as I stepped out of them. She took a step back and just stared at me. I felt very self conscious.
“You are so beautiful!” she said. “I am so lucky to have you.”
I blushed.
“No” I said. “I am the lucky one. I love you so much. I will be a good wife for you.”
Anna
Her comment brought tears to my eyes. She seemed really happy. I wanted nothing more than for her to be happy. It almost made me regret my feminizing her, almost. I knew that no matter how much I loved her I needed her to be her, not him. I stepped back from her and dropped my arms to my side.
“Your turn” she said.
Darla
I unbuttoned her jacket, slipped it off her and tossed it on the floor. Then I got down on my knees and removed her heels, one at a time. I unbuttoned her pants and pulled them down. I lifted each leg in turn so she could step out of them. She stood in front of me in her panties, bra, cami, nylons, and shoes. I thought I had never seen such a beautiful woman.
Then I lowered her panties and removed them. I looked up at her and smiled. She returned the smile. I leaned in and licked her pussy. I heard her gasp. She put her hands behind my head and pulled me towards her. My mouth was positioned at her feminine opening and I licked her again and again. She held me there while I continued to lick her, pushing my tongue inside her and sucking on her clit. My reward came when she came and let out a primal scream. She had several orgasms before she stopped me.
When she recovered she lifted me to my feet, took me in her arms and kissed me, tasting her own juices. Then she lifted me again and gently deposited me on the bed. She took each of my shoes off, one at a time, and slid my panties down. She tossed them onto the floor and with a smile crawled up between my legs. I wish I could say I was hard, but while I was excited and ready to make love to her, I was not. Undeterred she gently stroked me. I could feel myself trying to get hard, but unable to achieve a full erection. She then took me into her mouth and slowly sucked me. It did not take me long before I was spewing my semen, such as it was, into her mouth. I was totally drained, or so I thought. She made her way up my body and kissed me. As she had been doing whenever we made love she fed me my own semen. It was still warm and moderately thick coating the inside of my mouth. It was not my favorite aspect of our sex life but it pleased Anna and I was happy to accept it from her.
Then she positioned her pussy over my face.
“Make me cum again Darla!”
I needed no further encouragement. Her pussy was already leaking and dripping all over my face as I pulled her down to me. I went to work with my tongue. I loved hearing her moan and when she finally came her scream filled me with joy. I lost track of the number of orgasms she had before she finally rolled over next to me and pulled me to her. She licked her juices from my face and we kissed and hugged for several minutes. Then she rolled out of bed.
“Don’t go away!” she said with a smile.
She pulled something from her small suitcase and went into the bathroom. She was gone for a short time. I heard a small moan come from the bathroom. When she came out she was wearing a short nightgown with a big bulge around her groin. I got scared and I pulled my legs under me and backed up to the head of the bed.
“It’s ok sweetie” she said.
She sat on the edge of the bed next to me and took my hand.
“Do you trust me?” she asked.
I nodded in the affirmative.
Anna
I was not all that surprised at her reaction when she saw it. She knew I would take her virginity, she just didn’t expect it this way. Before strapping it on I used the dildo on myself to get it naturally lubed a bit, as my mother told me before giving it to me, that it was important that the sissy wife accept my natural fluids inside her during the consummation. This was tradition. While I had no intention of hurting her, I knew that the initial entry would cause her some pain. I had tried to train her with my fingers, but they could not duplicate the girth of the dildo. I felt confident that after the initial discomfort, she would enjoy being a girl in bed. I had no doubt of my alpha position in our relationship, but establishing her as the penetrated rather than the penetrator would cement that relationship.
“Wh..what do you want me to do?” she asked me nervously.
“Lie on the bed with your legs spread. Most important is that you relax. It will hurt less that way.”
She nodded. Trembling, she positioned herself as I instructed. I removed my nightgown revealing the big black faux cock I had strapped around me with big black balls dangling from it. I positioned myself on my knees between her legs. I lifted her legs and placed them over my shoulders, which caused her anus to open up for me.
Taking a tube of lubrication I had left on the night table, I put a generous amount on two fingers and inserted them slowly into her hole. I moved them around to coat the inside of her asshole which caused her to moan and her tiny penis to twitch. She was clearly enjoying this part. I continued playing with her ass for her pleasure and hoped it would relax her.
Finally I withdrew my fingers and applied a generous amount of the lubrication to my cock. She still looked a bit frightened but seemed to have relaxed a bit. I positioned the head of my cock at her entrance and teased her with it. Her soft moans indicated to me she was enjoying that. My cock was well lubricated so I slowly entered her. I got the head in and when she screamed I stopped and left it there. The look in her eyes was one of fear. It was almost enough to make me abandon my plan to fuck her, almost.
“Breathe sweetie! Take deep breaths!”
She took several breaths and she seemed to be relaxing. I pushed in a couple of inches, reminding her to breathe. I think if she told me to stop at that point I would have, but she said nothing though the expression on her face was a grimace.
“Are you ok?” I asked her.
She nodded.
“Should I continue?”
“Yes, but go slowly.”
I’m not sure she realized it but her cock was twitching. I smiled to myself and pushed in a bit more.
“Stroke yourself while I enter you!”
She nodded and followed my instructions. I smiled at her and pushed onward. Suddenly she gasped, but continued to play with herself. I don’t know if she realized it but I was almost all the way in. One final push would put me there.
Darla
I was surprised to see her dildo when she lifted the nightgown, but as I thought about it, it sort of made sense. She had assured me we would consummate the marriage but I could not get hard enough to penetrate her. I was so naïve that I did not know what she meant. I now found out. I trusted that Anna would not hurt me.
I tried to relax as she told me to and when she was rubbing her cock around my asshole it did feel good. I fooled myself into thinking that was all she was going to do, but then she entered me. It didn’t hurt all that much but the fear caused me to cry out and she stopped.
I obeyed her order to play with myself and she pushed it in further. I managed not to scream, though it was a bit painful. She stopped several times to allow the pain to subside and for me to catch my breath. I was surprised when I felt her balls banging against my ass. I realized she was all the way in. I felt very full and I was as erect as I could get. Despite having already cum once I felt I could cum again. That was very rare for me.
Anna
Once I was all the way inside her I looked at her face. She smiled up at me and was furiously stroking herself. Keeping my cock inside her I leaned over and kissed her with passion.
“Are you ready for a good fucking?” I asked her.
She smiled and nodded and I withdrew from her slowly, leaving only the head of my cock inside. Then I began to fuck her slowly. At first she grimaced a bit but after a few strokes she would raise her ass to meet me as I pushed forward. Her breathing became more rapid and seeing her finding pleasure in what we were doing caused me to approach my own climax. She continued stroking herself and when she let loose I also came. It was one of the best orgasms I had experienced. With both of us being spent I leaned over and lay on top of her with my cock still firmly in her ass.
Darla
I could not believe anything could feel so good. Momentarily I felt embarrassed that I had been fucked like a girl and enjoyed but I put it out of my mind. After all it was with the person I cared most about and would do anything for. I had to live as a girl to be with her, I would do that and be happy.
Epilogue
Years later......
Luisa
I was raised in a household dominated by my mama, Anna. There were just the four of us, me, my adoptive sister Annette and my mommy, Darla. Today would be an interesting day indeed. Both of my mothers wanted to meet my new boyfriend Kevin. I showed him around the house, told him how my moms met while in college and how I was conceived through IVF with a sperm donor. What I didn’t tell him was that mommy Darla was the sperm donor.
“Nice to meet you Kevin,” said Annette eyeing him. “They are waiting for you inside the living room.”
Annette was a beautiful girl of African descent. We were the same age. She was adopted so I could have a sister that would share with me the teachings of my mama as her mother did with her.
The meeting was inside our large living room adored with a large painting of my Grandmother above the fireplace.
We took our seat facing mama and mommy. Mommy Darla as always, allowed Mama Anna to speak first.
“So tell me Kevin, “What do you think of a female led marriage?”
END
Wonderful! Thank you! Xxx
ReplyDeleteLuv this story! Well written, kept me on the edge of my seat. Thank-you!
ReplyDeleteThank you, Gina. I greatly value all comments. I'm happy you enjoyed the story.
DeleteWell what can one say,Karen a lovely story told in a charming manner but the underhand manipulation by Anna and her family ,very bad girls on poor Louis Morally it is wrong to behave and act so but the tale is well told and narrated in a duo style very becoming truly a most accomplished writer and i suppose all's well that end's well.
ReplyDeleteWhile I find the fantasy of Louis's experience exciting, I do not condone real life without consent of all parties. I firmly believe that anything is acceptable between CONSENTING adults.
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