All characters are a product of my imagination and any similarity to any person, real or fictional is purely coincidental.
I wish to thank Ananabelle Brito for reviewing an making meaningful suggestions, most of which I have adopted to make the story more readable.
As always, please write a review, either positive or negative. I welcome all comments and try to learn from them. Thank you.
KJ
Karen Jensen
“I never gave him a hand job or any other kind of job.”“Hush” said Amanda. “Now get dressed and be quiet while we hear about graduation.”
I grabbed my bra from Tracey and slipped it on. It was a relief having it to hold up my new breasts. I looked around for my clothes but did not see them. Rosa smiled at me as she handed me a pile of clothing. Too my horror they were ultra feminine and consisted of nude stockings, a white corset and a hot pink denim skirt that barely covered the tops of my stockings. Not wanting to risk further punishment I resigned myself to wear what she gave me. To complete my outfit she handed me a pair of pink pumps with 4 inch heels.
While I was dressing Jane related the story of graduation. I was near tears as I recalled the most humiliating day of my life. At least it was until today.
I was up early on graduation day. I was going to wear my only suit and tie. I was looking forward to graduating and the end of school. I came out of the shower and wrapped a towel around my waist. I walked into my room intending to put on my suit but was shocked to find feminine lingerie on my bed and a fancy dress hanging on my closet door. I knew it was Jane’s idea. I went to my dresser to get out a pair of boxers, a tee shirt, and socks, but found only silky panties, lacy bras, and nylons. I was angry. A quick look in my closet also revealed only feminine clothing. My suit was nowhere to be seen. There was no way that I would dress like a girl for my high school graduation.
Wearing only a towel around my waist I went storming into Jane’s room, not waiting to knock. She sat on her bed fully dressed with a big grin on her face and just stared at me.
“Where are my clothes?”
“What do you mean?’
“You know damn well what I mean. I want my underwear, socks, shoes, and the suit that I was planning on wearing today to graduation.”
“Oh that. They are probably at the charity shop by now. I believe mom was making a run yesterday and I made sure she had plenty of stuff to take.”
“You knew I was going to wear that today. What am I going to wear?”
She grabbed my hand and dragged me back to my room.
“It looks like you have more appropriate clothing. I suggest you dress and I will help with your makeup.”
“No. You can’t do this to me today. Please Jane. Not today.”
“You will have to take it up with mom. I don’t care if you go to graduation or not, but I think mom will want to see you walk.”
I ran into the kitchen where mom was fixing breakfast.
“What is it dear?”
“My clothes are gone. Jane got rid of them. I have nothing to wear. I won’t be going to graduation.”
“That is not an option.”
She stood up and grabbed my hand, leading me back to my room. She quickly looked through my drawers and in my closet.
“If you can’t take care of your clothes you will wear what is here. That is a very nice dress. It was the one your grandmother wore to her High school graduation in 1958. I think it will look very pretty on you. Now get dressed and have some breakfast! Now!”
“No, I am not going to graduation dressed as a girl where everyone can see me.”
“You should have thought of that when you allowed Jane into your closet, besides what’s wrong with being dressed like a girl? “You dress like one often enough.”
“Not voluntarily.”
“No more talking. I will not miss seeing both of my children walk for graduation. Get dressed now or you will be spanked.”
I was so accustomed to obeying the two women in the house, knowing she was serious and realizing I was going to walk one way or another I asked them to leave the room.
“If you need help, ask Jane.”
She was the last person I wanted to help me, but I knew I had no choice. I soon discovered that the underwear was also vintage. The panties were white trunk style and the matching bra was a bullet bra. I also realized I would be wearing stockings, and not pantyhose. Jane told me, pantyhose had not been invented in 1958. To hold up the stockings and give me a more girlish figure I would be wearing an open bottom girdle with 6 garters hanging down.
Before I could react, Jane pulled the towel off of me leaving me in only my birthday suit. I then had to struggle into the girdle with her flashing a shit eating grin the whole time. I finally manage to get the girdle in place, wondering how women put up with them and sat on the bed to put on the stockings. I knew from my experience with pantyhose to roll them up my legs. I had a bit of trouble hooking up the garters and my sister graciously (NOT) helped hook the ones in the back. Then the panties came on over the stockings. I realized that going to the bathroom would be a bit of a chore. Next was a full white slip with lace at the top and along the hem. It fell just below my knees. I then stepped into two white crinolines with elastic waists. They fell just below the hem of the slip.
The dress was yellow with a very full skirt. It was sleeveless and came up to my neck. I needed help from Jane to zip it up in the back and I realized that I would be unable to remove the dress without help. The yellow pumps that matched the dress had 2 inch heels which, with my past experience in girls’ shoes were no problem for me to walk in. The whole time I was trying to figure a way out of going to graduation, but could come up with no ideas that wouldn’t result in pain for me.
I allowed Jane to fix my hair and makeup, deciding that if had to dress like a girl I should look as good as possible. She brushed my hair out and tied it into a high ponytail, tying it off with a yellow ribbon which matched the dress. When she finished, I did indeed look like a girl, and a rather pretty one at that. Of course, everyone at school would know the truth about me and I dreaded their reaction.
I was too upset to eat breakfast and as I sat on the backseat in the car I was still trying to figure a way out of walking. I had on the cap and gown which hid the dress, but with makeup on my face, my hair in a feminine hair style my bare legs and women’s shoes. It would not take a genius to realize I was in a dress. It was all I could do not to cry, but I had been warned not to ruin my makeup, at least not until after the ceremony.
When we got to school Jane grabbed my hand and led me to the auditorium where the ceremony would take place. She realized I might try to run and was not going to let me. In any case, I could not have gotten very far and had no idea where I would go dressed as I was. By that time I accepted my fate and was grateful I would probably never see most of these kids again.
We were back stage and lined up in alphabetical order meaning Jane was immediately in front of me. We marched into the auditorium and took our seats in first few rows. We listened to several boring speeches and then it was time for us to get our diplomas. They called us up in alphabetic order. I dreaded walking up there dressed as I was. I could imagine all the comments that would be coming my way. I heard the principal call Jane Taylor and knew I was next. I was not prepared to hear him call up Justine Taylor, which, predictably was accompanied by laughter from most of the students as well as some of the parents who knew me.
The principle did a double take when he looked at his list of names and then shrugged his shoulders. Clearly, someone had listed me in the feminine form of my name and the name Jane and her friends used. With head down I made my way onto the stage to receive my diploma. The principal had shaken each boy’s hand and kissed each girl on the cheek. My humiliation was increased when I put out my and to shake his and instead received the kiss reserved for the girls.
I was almost in tears when I descended from the stage. After the ceremony we returned to our homerooms to return our caps and gowns. That was when the other kids got the first look at my dress. Most of the boys broke out in laughter. There were a lot of remarks about my being a sissy and a pantywaist. One girl asked me if she could borrow a tampon. There were a couple of girls who complimented the dress and wanted to know where I bought it. A couple seemed interested in knowing if I were transitioning to female.
I could take no more. Crying, I ran out of the classroom as fast as I could in my heels, hearing their laughter behind me. I found my mother and grandparents waiting for me. Mother seemed uninterested in my emotional state but my grandmother pulled me into her arms and hugged me until I was able to calm down. She took out a hankie and wiped my eyes. Then she fixed my eye makeup which was a mess.
“I hate to say it, Justine, but you look much prettier in that dress than I ever did.”
That was not what I wanted to hear, but I said nothing. IT felt good to be next to my grandmother with her holding me close. We waited there until Jane showed up. She took my diploma from me and handed it, along with hers to our mother.
“No wonder he called you Justine” mother said “that is the name on your diploma.”
At that point I did not care and wanted only to go home and get out of the clothes I was wearing. That was not to be. Mother was taking us out to for lunch to celebrate. The only good thing about the day, I thought, was that it was over and I would not have to see any of the kids again.
It was when we got home that my new horror began. I had no boys clothing. Jane had succeeded in getting rid of all of them. Mother refused to replace my wardrobe and I had no money. All I had were some of Jane’s castoffs.
“And so he essentially became our housekeeper, that is, until he ran away” said Jane.
I heard Amanda and Rosa laughing at Jane’s telling of my humiliating experience at graduation. Only Tracy showed any sympathy or was it a look of pity. I couldn’t be sure. Both Amanda and Rosa hugged my sister and promised to see her again. It would be a lot sooner than I expected or wanted. Jane handed me a small pink purse. Amanda paid for our purchases, with a friends and family discount, and we left the store with my packages in hand and walked through the mall. I looked like a prostitute, which subjected me to more stares, snide comments, and further embarrassment.
I soon found that wearing 4 inch stilettos made it impossible for me to not keep up with Amanda and Rosa, and my pleas for them to wait fell on deaf ears. I walked as fast as I could but by the time I exited the mall they were nowhere to be seen. I walked to the spot that Rosa had parked in but got there just in time to see her pull out. I could not find Amanda. I checked my purse. I found lipstick and a compact. There was just enough money for me to take the bus, but that meant transferring and I knew it would take at least 2 hours to get home. I felt like crying.
Seeing no other choice I made my way to the bus stop at the mall. My feet were already hurting and I knew I would have a bit of a walk once I got off the bus. The bus stop was not crowded. There was a teenage boy who just stared at me. Eventually he made his way over to me. He appeared to be about 16 or 17, about the same age as Rosa.
“How much?” he asked me.
“I beg your pardon.” I responded in the most feminine voice I could manage.
“How much to let me fuck you?”
I turned away choosing not to dignify his question with an answer. He grabbed my shoulder turning me to face him and almost knocked me over.
“How much will it cost for a blow job?”
“Leave me alone, I don’t do that!”
”Yeah right!” he said sarcastically.
“You are obviously a whore, so tell me how much.”
Before I could reply the bus pulled up. I heaved a sigh of relief and got on. I walked to the back and took a seat by the window. It would be at least a 45 minute ride and then I would have to change buses. I was not happy.
I looked up as the same boy sat down next to me and smiled at me. The bus was empty except for the two of us. As the bus pulled out he put his hand on my knee. I looked down to remove it and realized my skirt was so short that my stocking tops and garters showed. He moved his hand up my leg and I put my hand on top of his to stop him. He grabbed my hand and placed it on his groin. He was already hard.
“Take it out!”
I was too nervous to respond and merely shook my head.
“Take it out or I will fuck you right here and now.”
I looked towards the bus driver. If he heard us he was ignoring us.
“He won’t help you bitch. This is your last chance. Take it out!”
He had a strong grip on my thigh and was squeezing it. I tried to stand up but he kept the pressure on.
“Take it out or I will hurt you” he said very quietly.
I believed him. I turned towards him and slowly pulled his zipper down. With tears in my eyes I reached into his boxers and pulled out his cock. It looked massive compared to my own.
“On your knees, open your mouth, and get to work!”
I slowly slipped down onto my knees and reluctantly started stroking his member a couple of times. I was trying to avoid sucking him off, but he grew impatient and pushed my head into his groin.
“Open your mouth slut!”
I obeyed him and allowed his thick warm cock into my mouth. I decided my best bet would be to bring him off quickly. While stroking him I licked the head and then ran my tongue along his shaft. I tried to mimic what Tracy had done to me. It was my only previous experience.
“That’s it bitch. Now lick my balls!”
I did as I was told.
“Now take it into your mouth!”
I took his cock into my mouth and little by little he began jamming it down my throat. He pulled out a little when I started to choke, but rammed it in again. Holding my cheeks with each hand he fucked my face and I was helpless to stop him. I heard his heavy breathing and felt him tense. I tried to pull away but he held my face tightly between his hands. I would soon feel and taste his hot cum spurting into my mouth and down my throat. He ejaculated two or three more times before growing flaccid and withdrawing. By now I was crying from the humiliation I was feeling.
He put his cock away and zipped up his pants.
He dropped a five dollar bill on the seat and moved up to take a seat away from me. When he finally got off the bus I managed to pull myself together and realized I had missed my stop. I took a look in the mirror of my compact and I saw my lipstick had been ruined. I also realized that I had cum on my skirt and corset. To make matters even worse, I didn’t have enough money to take the bus back to my stop and transfer, so I would have to walk back. It was a good mile away and my 4 inch heels were not made for walking. I fixed my lipstick and using a tissue, did the best I could to remove his cum from my clothes. Then I began the long torturous walk back to catch my bus.
By the time I got home it was very late and Amanda was pissed. I was too ashamed to tell her of my forced cock sucking by the teenage boy so I just told her I missed my bus. She took me over her lap and with my ass being sore from the earlier spankings I was crying after the first stroke. When she finished she told me to repair my makeup and get dinner on the table. I would only set 2 places, for her and Rosa. I was consigned to eating by myself in the kitchen. In some ways it was a relief not to have to suffer the humiliation they would rain on me. But, it was also a further indication of how my role in the house had been diminished.
I washed the dishes and cleaned the kitchen. I then reported to Amanda.
“Justine, we will no longer be living as husband and wife. You have proved to be inadequate as a husband. You will now be our housekeeper. As such, you will no longer share the marital bed with me. I have donated all your male clothing to charity. You will have no need of it. The clothing we bought for you today and the clothes that Rosa donated to you are in the guest room which will now be yours. Is that clear?”
It felt like déjà vu. Fighting back more tears I could only nod, being unable to speak. I wondered how it all came to this. She then sent me off to bed where I cried myself to sleep that night.
Now that I was their housekeeper, Amanda bought me several plain black and gray dresses, like hotel maids wear, for doing my household chores. Of course I wore frilly white pinafore style aprons over my dresses.
The next evening, Amanda handed me a box and told me it would be my evening uniform. I was not shocked to find it was a black French maid’s dress. It had an attached white petticoat and came with black fish net stockings, a black garter belt and black pumps with 4 inch heels. She gave me a white bra and matching silk bikini panties to wear underneath.
I did my chores for the day. Then I made a salad, and put dinner in the oven. For dessert Amanda requested ice cream so I did not have to bake, which was fortunate since my previous attempts had all been thrown out. While dinner was cooking I took a hot bath and dressed in the scandalously short maid’s dress that Amanda had given me. This would become my daily routine
One other issue I had was with Rosa’s boyfriend. When he would come to pick her up for a date he leered at me and when no one was looking, would pinch my ass or grope my breast. He knew, or at least I thought he knew who I really was, but it did not deter him from harassing me. Rosa encouraged him to paw me and laughed at my discomfort. He would often spend the night and I was expected to wash and iron his clothing so they would be fresh and clean for him the next morning.
About two weeks after my shopping spree Amanda informed me that Jane would be coming for dinner. It was not an event to which I looked forward. With Rosa having a date that night, I had the table set for two. I did my meal preparation in advance so I would be free to be at their beck and call. I did not want to give either of them a reason to punish me.
At the appointed time Jane arrived with Tracy in tow. He was dressed as I was, in a black French Maid’s dress with 4 inch black stilettos. Jane told me that he would assist me. I surprised myself when I realized I was happy to see him. Perhaps he would take some of the focus from me and reduce the probability of my getting punished.
As it turned out, Both Amanda and Jane pretty much ignored us other than to order us to get them something. They were very much into each other. After dinner, they took their coffee, dessert, and brandy into the living room. That allowed Tracy and me to eat in the kitchen and clean up.
When we finished our kitchen chores we went to the living room to report to our mistresses. I had not expected to find them locked in each other’s arms, kissing and feeling each other up. They were both topless and apparently had not heard us come in. When they noticed us, they showed no embarrassment at being caught, but did disengage and turned to us.
Later in the evening, Amanda announced that Jane and Tracy would be spending the night with us. I was ordered to fetch two baby doll nightgowns and bring them to her. When I returned to the living room, Tracy was standing there completely naked, save for his high heels, and was clearly embarrassed having to appear that way in front of Amanda. The two women sat on the sofa in front of him holding hands.
I was ordered to undress by Amanda and had no thought of disobeying her. I had been naked in front of Jane enough in the past to not consider any embarrassment it might cause me. In a short time I also was naked and standing in front of the two women in only my high heels. We were ordered to hold hands and come forward toward them.
Amanda took out a spray bottle and sprayed it around my penis, dissolving the adhesive and allowing it to drop for the first time since it had been imprisoned two weeks earlier. I could not remember having gone that long without an orgasm. Jane was doing the same for Tracy. I was so horny that my cock immediately sprang to attention. Tracy followed suit and we both stood there in front of our mistresses at full mast.
“We have decided to reward both of you for the service you provided us tonight and allow you to orgasm.” Amanda stated. “As the guest, Tracy will have his orgasm first. Justine, you will bring Tracy to orgasm.”
I can’t say I was terribly surprised, though it was not what I particularly wanted to do. I reached over and took his cock in my hand. I realized that he was quite a bit bigger than me, which added to my humiliation. I stroked him a couple of times before Jane interrupted me.
“No, Justine. Not with your hand, with your mouth. And there better not be any semen on the floor or you will be punished.”
I started to protest, but stopped when she put her hand up. She merely pointed at the floor. I got down on my knees and leaned over. I licked the tip and he moaned. Deciding to get it over with as fast as I could I put my mouth over the head of his cock. Slowly I took him into my mouth. I did not believe I could take the whole thing in, but he held my head and rammed his cock deep into my throat, causing me to gag. He withdrew but repeated the action. This went on for several minutes before he tensed up and released his semen into my mouth. With his cock buried in my throat I had no choice but to swallow his load. By the time he grew flaccid and withdrew I was in tears, bawling like a baby. Somehow this was far more humiliating than my experience with the boy on the bus. I had sucked another man’s cock in front of my wife and sister. It was an experience I could never live down.
“How cute you looked with a cock in your mouth” said Jane. “Maybe I should have let you continue what you were doing with Bruce at the party.”
“You really are cock slut, princess” commented Amanda.
“I think she enjoyed it.”
I looked up at Amanda shaking my head but stopped. She was pointing at my tiny penis which was hard as a rock. I wanted to tell her it was only because I was so horny, but before I could say anything she stopped me.
“It is your turn now Justine. Reverse positions!”
I stood up and watched Tracy as he got down on his knees in front of me. I was so horny that I came almost as soon as he took the first lick and he had to hurry to take me in his mouth so as not to spill a drop. When he stood up we were ordered to kiss. Tracy turned to me and put his arms around my waist, pulling me to him. At first he kissed me gently on my lips but then put his tongue in my mouth, forcing me to taste myself. I was very passive but seeing how feminine and pretty he looked I found myself getting turned on again and returned his passion. We kissed like that for what seemed like an hour, though it was quite a bit less when we broke apart.
Amanda and Jane both applauded and I found myself blushing with embarrassment. I realized I was erect and a quick glance at Tracy told me he was in the same state.
“Come forward girls” said Amanda pointing to a spot about 2 feet in front of her.
We obeyed and curtsied though we had no skirts to grab onto. Amanda handed us each a baby doll night gown and ordered us to put them on. Mine was lavender and Tracy’s was pink. Other than the color they were identical.
“It’s time to go to bed. You will both sleep in Justine’s bed” said Amanda. “Hold Tracy’s hand and take her to your room.”
“Have fun girls!” said Jane.
Amanda and Jane both laughed as we curtsied and scurried to my bedroom with our erections bouncing free since we were not given any panties.
The stress of the day, combined with the work I had to do exhausted me and I wasted no time in lying down on the bed turning my back away from Tracy. I felt him lie down next to me. The bed was too narrow for us to sleep without having any contact. I had never slept with another man and was not happy about the idea but I had to make the best of it.
I was awakened by loud moans coming from Amanda’s bedroom. Clearly they were having sex, something I would have loved to have had with Amanda. Then I felt Tracy’s hand caressing my ass. The last thing that I wanted to happen occurred. I got an erection. He reached his hand around and started to stroke me.
I was responding to a sexual advance made by another male, albeit a very feminine male. He pulled his hand from my ass and I felt something cold in my anus. His finger went in and I realized he was lubing me up and I had a good idea why he was doing it.
“Please don’t!” I begged.
“But I want to and your mistress ordered me to fuck you.”
“No!” you don’t have to do it. “We can tell her that you did.”
He ignored my protests. With his weight on me I had no leverage and could only lie there as he worked a second finger into my anus and then a third. That was not to be enough, and soon he withdrew his fingers. I felt his cock at my entrance and made one last plea for him to stop. He ignored me and slowly pushed his way in. I took a deep breath as he relentlessly penetrated me until I could feel his balls banging against my ass.
He pulled me up so I was on all fours and told me to stay like that. I tried to scream but he jammed a pillow into my mouth and all that came out were muffled grunts. Holding firmly onto my hips he slowly withdrew and then rammed his cock all the way in. I started crying from the pain of it. I could feel him drawing pleasure from being inside me as I could hear his heavy breathing and moans of pleasure. He slowly worked up a smooth rhythm and as my pain subsided, it was replaced with pleasure and I was growing harder
Despite having no friction on my cock I felt my orgasm building. I gradually lost myself in the feeling of being fucked. It would only be later as we lay together, bodies entwined, that I would feel the deep humiliation, as the realization hit me that I had been fucked like a girl and, not only enjoyed it, but had an incredible orgasm from it.
When I awoke the next morning my anus was very sore. Tracy noticed my discomfort and put some cream in it which would ease the pain and told me I would get accustomed to it. I was not sure that is what I wanted, but said nothing.
We were told to take a shower together by our mistresses. Tracy took my hand and put it on his cock, which immediately became erect. It took only a few strokes before he ejaculate all over me in the shower. After he returned the favor we hurriedly dressed in our maid’s dresses from the night before and went to the kitchen to prepare breakfast for our mistresses.
Jane and Tracy left after breakfast. Amanda reapplied the adhesive locking up my penis. I was ordered to change into my daytime uniform and proceed with my daytime chores.
Amanda and Jane started to meet regularly. It soon became obvious their relationship was more than platonic. I wasn’t surprised that Jane was interested in Amanda. I had suspected her of having lesbian relationships with some of her girlfriends in high school. I was not however, aware of Amanda’s interest in other women. The next few weekends were spent with Jane and Tracy, either at our house or at Jane’s. In both cases I slept with Tracy and was required to service him both orally and anally. I hated to admit it but he was right, I did grow accustomed to it. While I certainly enjoyed the orgasms, I felt very humiliated and embarrassed at my enjoyment in being fucked by another male. I had truly become Tracy’s fuck buddy, if not his paramour.
During the week I continued to perform as Amanda’s maid. I was required to curtsy to both her and Rosa when entering and leaving a room and when verbally responding to their commands. It was even more humiliating when Rosa’s boyfriend was there, which was quite often. My discomfort was increased by the way he leered at me and he had no qualms about slapping or pinching my ass. Rosa would laugh when he did that and it even drew smiles from Amanda.
After one weekend, Amanda called me into her room and ordered me to strip. I assumed she was about to lock me up prior to changing into my working uniform. I was surprised to see a set of male clothing on the bed.
“Justine, it is decision time for you now.”
“What do you mean?”
“Jane and I have decided to cohabitate. You may choose to stay and be our sissy maid, subject to our whims as you have been or you may leave. Should you decide to leave, I have a set of men’s clothing you can wear and I will remove your breasts. Also, I know you have no money so I will give you a substantial sum to allow you to rent an apartment and support yourself for a time while you look for a job. This is a one time offer and you have one hour to decide. Should you decide to stay and change your mind in the future, there will be no money and no men’s clothing for you to wear when you leave. Do you understand?”
I stood there in shock. It was the last thing I expected. Part of me wanted to take her up on the offer to leave. But I was afraid. I had held only menial jobs and was not qualified to do much other than to be a maid. While there was constant humiliation and frequent punishments from Amanda, Rosa, and her boyfriend, and I could expect more from Jane, there was security and in a perverse way a certain amount of comfort. I also found that I looked forward to being with Tracy. Maybe it was that being with him was the only way for me to have sexual release, but I had learned to take pleasure in it. In the end it was an easy decision for me.
Very enjoyable
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