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I never knew my Mom. She left my dad and me when I was 3 and I have only an image of her in my mind, but no recollection of who she was. When I was 7, my dad married a widow, 8 years older than him with twin daughters, Jordan and Alison, who are 7 years older than me. My step-mom treated me well, but clearly favored her daughters. Conflicts between either of them and me were usually settled in their favor, though with the age difference, there really weren’t very many. I also learned very quickly that her word was law in our house. I saw my dad always yielding to her as well. My step-sisters were very nice to me, baby sitting me until I was old enough to be left alone and never showed any resentment when asked to do that. They loved me and I them.
My whole life changed when Jordan became engaged. She was so excited when she came home early from her date, dragging her fiancé with her and excitedly showed off her engagement ring to the family. The wedding planning started immediately. My sister wanted the wedding to take place in two months, which left little time for my mom to get it all together.
A few days later the subject of the bride’s attendants came up. Alison, of course, was to be her maid of honor. She had asked a couple of her close friends to be bridesmaids. Then she shocked me by asking if I would also be a bridesmaid. I laughed, thinking she was joking, but soon realized she was dead serious. I refused, naturally, but my step-mother interrupted and told me in no uncertain terms that on the day of her wedding, the bride is the queen and I would do whatever she asked.
Jordan's reasoning was that she wanted her siblings up there with her and since David, her fiancé, was having his brothers and male cousins stand for him, she wanted her sister and brother up there with her. I appealed to my father, but unsurprisingly, he merely said it might do me good to ‘see how the other half lives’. My step-mom ruled the roost in our house, so I expected that appealing to my father would be in vain, but I had to try anything to avoid what I knew would be the most humiliating experience in my 15 years of life.
Jordan tried to calm me by saying I would only be wearing a dress for a few hours the day of the wedding. Her words did not have the desired effect at all nor were they accurate.
My ordeal actually started the following Saturday when mom woke me up at 7:00. Normally I would have slept till about 10:00, had breakfast and gone out with my friends, returning home in time for dinner. Those days were gone, as I would soon learn.
“Your girl lessons start today. Now get into the bathroom. After your shower I will dress you up and see what I have to work with. From now on, until the wedding next month, you are a girl.”
“No way! I am not gonna do it. I am not gonna be a bridesmaid. It is a stupid idea and I will not put on a dress for anyone!”
My stepmom was a big woman. Not fat, but tall and broad, even bigger than my dad and me. She grabbed my arm and in one motion was sitting on my bed with me lying across her lap. She pulled down my pajama bottoms and proceeded to spank me. I kicked my legs and screamed and was soon crying and begging her to stop.
“Now, are you going to do as I tell you or shall I continue spanking you?”
“I will do as you ask” I cried.
She took me into the bathroom and ordered me to strip.
“But mom, not in front of you.”
“You don’t have anything I haven’t seen before. We don’t have time for any of your silly games. Remove your pajamas now!”
I recognized the implied threat and as embarrassed as I had ever been, I removed my pajamas and quickly covered myself with my hands. She began rubbing some kind of cream on my body, covering everything below the neck. She made me stand there for 10 or 15 minutes until it started to burn. Then she turned on the shower and told me to wash up and meet her back in my bedroom. I didn’t have much hair yet, but was disturbed to see what there was of it wash down the drain, leaving my skin as smooth as a baby’s.
I wrapped a towel around my waist and went to meet her in the bedroom, nervous about what was to transpire. She rubbed some sort of cream all over my body, telling me it would soothe my skin. Then she handed me a pair of plain blue cotton panties and told me to put them on.
“Why can’t I wear my boxers?”
“Girls don’t wear boxers under their dresses. For all intents and purposes, you will be a girl at the wedding, so you need to learn how to dress and act like one. Think of it as being in a play. Any actor will tell you to be convincing in a part you have to become the character. Your character happens to be female. So while rehearsing, you will dress the part. You don’t want everyone laughing and pointing at you saying ‘that’s a boy in a dress’, do you?”
“No, I wouldn’t want that.”
“I didn’t think so. So we start turning you into a girl today. Now put on your panties.”
I turned my back to her and stepped into the panties. They came up only to my hips and felt incredibly soft. To my horror, I watched the bulge in my feminine undies grow. It did not go unnoticed by my Mom.
“It would appear that wearing girls’ clothing is not as unpleasant as you make out.”
“I..I can’t help it.”
“I know. Why don’t you go to the bathroom and take of care of that” she said softly.
Humiliated, that my mom would effectively tell me to jerk off seemed to make my erection get even harder. I went back to the bathroom, stroked myself and quickly erupted. I cleaned myself and wiped up the floor with a towel. Then I pulled up my panties and went back to the bedroom. Mom hugged me.
“I’m sorry Kevin. I know it is embarrassing, but it is important you obey me now. You do want to make Jordan happy, don’t you?”
Putting like that made it impossible for me not to agree with her. I truly loved my sisters and always thought I would do anything for them. I just never considered that I would be asked to do this.
Embarrassing me even further, mom then pulled my panties down, grabbed my balls and forced them inside me from where they had descended, and then tucked my penis back between my legs before pulling my panties up.
“That is much better.” she said. “Look in the mirror!”
To my horror there was no male bulge. My groin looked like that of a girl. I felt like crying, but guys don’t cry and, after all, I was still a guy.
“You will have to learn to do that for yourself” was all she said.
She then had me lay on my back and applied some kind of cream, which I learned was in reality, an adhesive, to each side of my chest. Then she took what looked like blobs and held them down for about 5 minutes where she had applied the adhesive. I learned that they were breast forms and when I stood up I could feel the weight on my chest. A quick look in the mirror confirmed my suspicions. To me they looked huge, though mom told me they were only a B cup, appropriate for a girl of my age and size. Mom then applied some makeup near the seams, effectively hiding them and making the breasts appear as if they were really mine. She had me slip my arms through a blue bra that matched my panties and hooked it in the back. She adjusted the straps and allowed me to look in the mirror. From the neck down I appeared to be a girl.
She had me try on various outfits, which I recognized as having belonged to my sisters, before settling on a short green pleated skirt and yellow sweater with a cowl neck. She showed me how to put on pantyhose and gave me a pair of black sandals with a 2 inch heel.
“You will graduate to higher heels in the coming weeks since you will be wearing high heels at the wedding. For today, these will do.”
I followed her to her room. The heels were not too difficult to walk in and, being somewhat shorter than average, I actually enjoyed having the extra height. She sat me down at her vanity and began to apply makeup.
“You will learn to do this for yourself over the next few weeks. Otherwise you will risk exposure. Do you understand?”
I nodded. As she applied each bit she explained what she was doing and why. When she was finished she produced a brown wig which approximated my own hair color.
“Your hair is almost long enough to style, so you will not get a haircut. When it is a bit longer I will take you to my stylist.”
After fitting the wig onto my head, she secured it with bobby pins and styled it with a comb and brush. It was parted slightly off center and hung just above my shoulders.
Then she took me into her closet where she had a floor to ceiling mirror and stepped away so I could look at myself. I was shocked to see the cute girl staring back at me, one I would certainly be interested in getting to know, that is, if she were not me.
“Now let’s go introduce you to your father and sisters, and have some breakfast.”
“I can’t let them see me like this!”
“Of course they will see you" she laughed. "Remember, you will be a girl at the wedding.”
“They will laugh at me and tease me.”
“They won’t. They have promised not to laugh or tease you. They want to help you.”
With more than a little bit of trepidation, I followed her out of her bedroom and into the kitchen.
“Oh my lord!” cried Alison when I walked into the kitchen. “She is so sweet. Is that really you Kevin?”
I blushed, knowing she meant it as a compliment. I wasn't sure how I felt about looking "sweet" while dressed like a girl. Jordan and my dad just stared, like they couldn’t believe their eyes. Finally Jordan spoke.
“We can’t call her Kevin. She definitely does not look like a Kevin. We need to give her a girl’s name.”
“I know” Alison piped up. “We’ll call her Caroline, as in sweet Caroline! What do you think?”
Jordan liked it as did dad and mom. I didn’t really care. So, I became Caroline. Jordan and Alison both agreed they were going to enjoy having another sister.
“Well, it looks like I have another daughter” was all dad said, chuckling.
I felt like he was betraying me by accepting my feminization with such calm. We sat down to breakfast and mom handed out assignments for when we finished eating and cleaned up. Jordan would teach me how to put on makeup for the first two hours. Then Alison would work on walking, sitting, mannerisms, etc. Then mom was going to take me out for a drive and teach me how to enter and exit an automobile while wearing a skirt, and have me get accustomed to being seen in public as a girl.
"I know how to get into and out of a car!?" I said.
"You don't want to show off your panties, do you Caroline?" asked mom.
"No, I don't want anyone to know I'm wearing panties or any of this."
"You will be wearing a skirt or dress and panties so you will learn how to comport yourself while so dressed, or you will be the one who is embarrassed. Ok?"
"Yes ma'am" I answered softly, realizing that any further argument would be futile.
I barely touched my breakfast and when everyone was finished we got to work. By late afternoon I was beat. I spent the day putting on and taking off makeup, walking, standing, and sitting. I learned to smooth my skirt under me when sitting, to sit with my knees together or crossing my legs at the knees or ankles to keep from showing my underwear. All I wanted to do was to lie down, but mom was insistent we go for a drive.
Jordan and Alison wanted to ride along with us, but mom refused. She said that she wanted alone time with me. I would have preferred that my sisters accompany us. They were both very pretty and I hoped people would pay less attention to me. I sat in the front seat with mom and she kept telling me not to slouch. I was nervous every time a car pulled up next to ours, but if anyone guessed my true gender, I was not aware of it. We drove for about 1/2 hour to a park on the outskirts of town, one where it was unlikely we would see anyone we knew.
"Get out of the car, Caroline. We are going to take a walk."
"You said I didn't have to get out of the car."
"You did very well today. You are carrying yourself like a girl, you look like a girl, and I see no reason to postpone it. You have to appear in public sooner or later, so it might as well be now. Don't worry, I will be with you. Besides, there are not very many people around."
"No buts, out of the car Caroline, NOW!"
I opened the door, and keeping my knees together as I was taught, I swung my legs out. I was so nervous I was shaking as I slowly stood up. Mom put her arm around me and told me to take a few deep breaths. It didn't help much, but mom took my hand and led me. I relaxed a little when the people passing us paid no notice of us, other than to nod or say hello. No one screamed
"It's a boy wearing a dress!"
There were a couple of guys who seemed to take an undue interest in me, but mom told me they were just admiring a pretty girl. I didn't know whether to be upset or relieved.
It was a new experience feeling the cool breeze blow up my skirt and I had to hold it down a couple of times so as not to display my panties. We walked around the park for about 20 minutes before returning to the car. By the time we got home I was mentally and physically exhausted. The fear of discovery had certainly taken its toll.
Once we were home, Mom had me slip on a bib apron which she tied into a big bow in the back. She said it would keep my clothes clean while I helped prepare dinner, something I was not accustomed to doing. Normally one of my sisters assisted her. Now that I was supposed to be a girl, it would also be one of my chores as well. All I could think was that I couldn't wait for the wedding to be over and I could be a boy again.
After dinner, I helped clean up and then watched a bit of television before exhaustion set in and I excused myself to go to bed. Mom walked me to my room to teach me how to remove my makeup and then handed me some white, silky baby doll pajamas to sleep in. I was too tired to protest and was grateful she left me alone to change into them. I struggled removing my bra before realizing I could slide the straps off my shoulders and spin the hooks around to the front. The baby doll panties felt really nice when I pulled them up and I found myself sporting an erection. I quickly put on the top and raced to the bathroom where I relieved myself.
She had not removed the breast forms and I realized I had a problem as soon as I slipped under the covers. I was accustomed to sleeping on my stomach and that was clearly not going to work. Eventually I fell asleep on my side. It was a very restless night as I could not help but think about all the things that could go wrong.
Sunday was much like Saturday without the public excursion, for which I was grateful. I spent more time practicing putting on makeup and taking it off; and more time walking and sitting. I tried on more of my sisters’ clothes so mom could get an idea of what styles looked good on me. It was another exhausting day. I was so tired I forgot to ask mom to remove my breasts before going to bed. I had school the next day and had no intention of going with my new breasts.
Mom woke me up and told me to shower, and that she would leave clothes for me. She didn’t normally pick out my clothes so I was a bit puzzled, but before I could ask her about it she was gone. I went looking for her still wearing the short nightie I had slept in and asked her to remove my breasts.
"No. You will keep them on."
"But I can't have them on for school."
"You are not going to school. You will be home schooled for the rest of the semester and continue to live as a girl"
"You can't mean that. I can't do that. I won't!"
"Look Caroline. It will be too confusing to be spending part time as a boy and part time as a girl. It will be much easier for you to carry out your impersonation if you live as a girl fulltime. Now go shower and I will leave clothes for you to wear."
"Please mom. I will be a bridesmaid, but don't make me live as a girl."
"The decision has been made. Now go get ready or do you need further incentive?"
Recognizing the implied threat of another spanking, I retreated to the bathroom and took care of my morning ablutions. When I was finished, I wrapped a towel around my waist as I usually did and headed back to my bedroom. Mom was in there laying out some clothes for me. She looked up when I came into the room.
"No, not like that!" she said. "A girl wraps her towel above her breasts, like so."
She then removed the towel leaving me in all my nakedness and rewrapped it so it covered my semi-permanently attached boobs.
"Caroline, I have hired a tutor for you. She will not only tutor you in your school work, but will help you to become more feminine and teach you how to dance as a girl. She does, however, insist on your wearing a school girl uniform, so I have gotten you 3 of these skirts and 5 blouses."
I looked at the skirt and it was red and pleated, and extremely short. The blouse was white and very sheer which meant my bra would be visible. There were also white knee high socks and red Mary Jane shoes to match the skirt, as well as white cotton panties and a white bra.
"Now get dressed and come to breakfast. Ms. Dunham will be here in about 45 minutes."
After breakfast I sat in the living room, dreading the arrival of my tutor. Mom had added a white bow to my hair. The skirt barely covered my panties. I remembered to keep my knees together and looked like a young girl sitting there. Mom told me to answer the door when the bell rang. My dad and sisters had already left for work and mom was waiting for the tutor before she too would leave.
I didn't have long to wait before I heard the door bell. With no small amount of fear I answered it and was shocked to see a young beautiful woman standing there. She had to be in her early twenties. She gave me a big smile.
"Are you Caroline?"
"Um..yes.. I am Caroline."
"I am Miss Dunham, your tutor."
She held out her hand to me. I took it and shook it."
"Please, come in." I said nervously.
I noticed she was carrying a gift wrapped package in her other hand. Just then my Mom walked in and introduced herself. She then excused herself, telling Miss Dunham she had to go to work and left the house, leaving me alone with this beautiful young woman, who was making me increasingly nervous by just staring at me and smiling.
She handed me the package and said "This is for you. Why don't you open it?"
I took the package and tore off the gift wrap. I opened the box to find a dozen pair of panties, all in different pastel shades. They were generously decorated with lace at the waist and leg openings. My jaw dropped.
“Why would she be giving me such a gift?” I wondered.
I didn't know what to say. She looked at me for a few moments and finally said:
"One of my tasks is to teach you to be a girl. One thing you will have to learn is not to display your panties. That is one reason you are wearing such a short skirt. So we will be playing a game. You will pick out a pair and put them on without telling me what color they are. If at some point during the day I see them, I will call you on it and you will get a demerit. Then you will go put on a different pair. Each demerit will earn you a spanking. This will go on until you can get through a whole day without revealing your panties. Do you understand?"
"Yes I..I guess so.”
“There will also be demerits for any unfeminine behavior, gestures, mannerisms, etc. Do you understand that?”
I swallowed hard and merely nodded.
"Good, now take the box of panties to your room and put on a pair and we will start our lessons for the day."
Surprisingly she started off by reviewing what I was studying in school. We were sitting at the kitchen table going over my lessons. She asked me to get her a glass of water. When I came back I kind of flopped into the chair as I normally would and my skirt flipped up in the back. There I earned my first demerit. We spent the morning on my academic lessons and broke for lunch. She sat at the table while I made us sandwiches. Bending over to pick up a dropped spoon earned me my second demerit.
The afternoon was spent with her teaching me to be a girl. The last hour was spent with her teaching me to dance the girl’s part. As I said earlier, she was young and pretty, and dancing so close to her was causing a predictable reaction.
“Caroline, do you know how to tuck your package between your legs?”
“Uh huh” I replied with my face turning bright red.”
“Then I suggest you do that so we can continue.”
I went to the bathroom and did as she told me. Then we continued our dance lesson.
After the dance lesson she packed up her stuff and I went to the bathroom. Figuring we were done for the day, I did not bother to tuck. When I returned she told me it was time for my spanking. I had earned 10 demerits for the day. I looked at her closely and decided that there was no way she could force me to accept a spanking from her and refused to lay across her lap. It seemed like it was a small effort on her part to get me across her knees. I lay there with my cock against her thigh. As punishment for defying her she was going to double the number of strokes to 20. She lifted my skirt and spanked me with her hand on my pantied ass. By the fifth stroke I was crying. Each time she hit me I moved slightly and humiliatingly I found myself getting hard, despite the pain. By the 12th stroke I was as hard as I ever was and feared I would cum. She had to be aware of the effect she was having on me but there was no indication from her that she was. On the 19th stroke I started to orgasm and she just let me lay there until I came, soaking my panties. I started crying from the humiliation I felt.
She gently laid me on the floor until I could put myself together and stop my bawling. I felt like such a sissy and could not look her in the eye.
“Caroline! Look at me!”
I looked up at her expecting to see her laughing. She had a serious expression on her face.
“You are not the first boy who I have taught to be a girl, nor are you the first to orgasm during a spanking. You will hand wash all the panties you wore today, drip dry them, and have them ready for tomorrow. You may change out of your uniform. Your Mom left a dress in your room for you to wear. I will see you tomorrow.”
With that said she stood up and without looking back left the house.
She tutored me for the next 6 weeks. By the end of the first week I was successful in getting through the day without any demerits. I tucked and avoided having any more orgasms during the spankings.
The following Saturday we were to go shopping for Jordan’s wedding dress. I had hoped to skip that, but since we would also be looking at bridesmaid dresses my presence was required. Mom had me wear a short yellow dress with a rounded collar and cap sleeves which hung from my shoulders to about 3 inches above my knees. I had seen Alison wear it several times and thought she looked great in it. I felt quite humiliated to be wearing it now. The dress was practically transparent so I wore a full slip underneath. I wore yellow cotton panties and bra, and pantyhose. By this time, tucking my package had become second nature so I needed no reminder. White low heeled sandals completed my outfit. I did my own makeup and Mom complimented me on the job. Despite my embarrassment I felt a sense of pride at having accomplished that. Once again, however, I had to interrupt my dressing to take care of myself. I found dressing like a girl to be both embarrassing and exciting and wondered why it excited me so much.
We stopped at a store specializing in wedding and bridal attendant’s dresses and accessories. Heather and Lori, the other bridesmaids, met us there. Of course, they knew who I was and Mom had asked them not to tease me. They each gave me a hug and told me they were happy I would be a bridesmaid. Mom said that we would be able to get all we needed here. I prayed we wouldn’t meet anyone I knew.
Mom and the girls went looking through the wedding dresses, picking them out for Jordan’s approval. I was kind of bored and just started wandering through the store, not really paying attention to where I was going. The store was filled with dresses, petticoats, stockings, shoes, underwear, you name it, all intended for the bride to be and her bridesmaids.
“Excuse me miss. May I help you?”
I looked up to see a cute girl, about 3 or 4 years older than me.
“Er..no. I was just…m..my sister is getting married and is looking at wedding dresses.”
“Don’t you want to help her look?”
She stared at me with a questioning look in her eyes before suddenly straightening up with a big grin on her face.
“Come with me!”
She grabbed my hand and led me to a back room.
“You’re not a girl, are you?”
I felt my face turning red and my eyes started to tear.
“Oh, it’s ok. I won’t say anything.”
She handed me a tissue to dry my eyes.
“Have a seat and I’ll get you some water. By the way, I’m Ashley. My mom owns the store and I help her out on weekends and holidays. What’s your name?”
She hesitated for a minute like she wanted to say something else, but her face broke out in a big smile. She sat down next to me on the bench.
“OK, do you want to tell me why you’re here and why you are dressed up as a girl? You are very pretty, by the way.”
I felt myself blush and thanked her.
“My sister wants me to be a bridesmaid, and mom insisted that I learn to be a girl.”
“Do you like it?”
“No! But I don’t really have any choice.”
“Well, I will keep your secret and I won’t tease you.”
She gave me a hug which felt really good. Then I heard my mom calling “Caroline! Where are you?”
“I better go out to her. Thank you for the water and ... you know.”
She gave me a peck on the cheek and I went out to find my mom and the girls.
“There you are Caroline. Jordan has picked out a pattern for her bridesmaid dresses and you need to be measured. Go into the dressing room and strip down to panties and bra.”
I was horrified at the prospect but before I could say anything Ashley grabbed my hand.
“Come with me Caroline, I will take your measurements.”
She led me to a dressing room and had me remove my dress and slip. Then I stood on a pedestal and she took various measurements.
“So, Caroline, I don’t want to embarrass you but why is there no male bulge in your panties?”
I found myself blushing again, but decided to answer her truthfully since she was so nice.
“May I see?”
Before I could answer, she had pulled down my pantyhose and panties and my cock popped out. To my chagrin I had an instant erection.
“Oh dear” she said smiling “we’ll have to take care of that.”
She caressed me with her hand which made me even harder and then surprised me by taking my cock in her mouth. I had heard guys talk about getting blow jobs in the locker room, but never could I imagine what it truly felt like. Feeling my hard cock in her warm mouth was like no other sensation I ever felt and before long I was moaning in ecstasy. In a short time I was spouting forth and she seemed to be swallowing it all. When she had drained me dry she looked up at me and smiled. She kissed me on the lips and forced her tongue into my mouth, giving me a portion of my own cum. Then she held the kiss until I swallowed it.
“That was nice” she said. “I hope you enjoyed it as much as I did. I think you better get dressed now.”
She watched closely as I put my balls back up into my body, pulled my now flaccid cock back between my legs and pulled up my panties and pantyhose. She helped me into my slip and dress and before opening the door, pulled me to her, wrapped her arms around me and gave me another passionate kiss. I was in kind of a daze when I walked out to mom waiting for me.
“What took so long Caroline? Did you cooperate with this nice young lady?”
“She was very cooperative” said Ashley. “We got to talking and the time just slipped away. I got to know her a bit better and must tell you that you have a lovely daughter.”
Mom nodded to her and smiled, then took my hand, leading me out to the car.
“Jordan picked out her wedding dress, Alison’s maid of honor dress and the bridesmaids’ dresses. The girls went off with Lori and Heather and you and I are going to hit the mall. You need more clothes to carry you through to the wedding.”
“I can’t go to the mall like this. My friends will be there. Please mom, don’t make me do this.”
“We are going to the Westfield Mall. It is on the other side of town and I doubt you will see anyone you know.”
I knew it would be a losing fight so I sat there quietly while mom drove us there, dreading the whole experience. Our first stop was a store catering to teenage girls. There I tried on all kinds of dresses, skirts, and tops. The dresses and skirts were all short befitting what girls my age wore. I could not believe how much we bought. We had to carry the packages out to the car before resuming our shopping.
The next stop was the lingerie section of a department store. There she bought me a dozen pairs of panties of various types and materials, some with matching bras. She also bought me some slips for those dresses and skirts that required them, a dozen pairs of pantyhose of different colors and several frilly nightgowns.
Our last stop was a shoe store where I walked out with 6 pairs of shoes, also of different styles and heel heights. The problem I had there was the suspicion that the man helping us was continually peeking up my dress while he was putting the shoes on my feet. I prayed he didn’t detect my true gender.
I continued practicing being a girl under the tutelage of Miss Dunham. My girlish mannerisms were becoming second nature and I wondered how I could ever return to being a boy. I learned to walk in higher heels since I would be wearing 4 inch heels for the wedding. I was also taught to talk in a more feminine voice without sounding like I was faking it. I could feel what remained of my masculinity slipping away. There were excursions out in public to increase my confidence that I could pass. It was very disconcerting to realize that boys staring at me were checking me out. Fortunately I was always with Ms. Dunham, my mom or one of my sisters, so I didn't have to deal with them alone.
Two weeks later our dresses were ready and we would be going for the final fittings and any necessary last minute alterations. I wore a white sundress with red flowers and took extra care with my makeup, hoping Ashley would be there. Heather and Lori were waiting for us when we arrived at the bridal shop and we all walked in together. This time, we stood around while Jordan tried on her wedding dress. She really was going to be a beautiful bride. There were a few alterations needed and when she went into the dressing room to take off her dress, Ashley grabbed my hand and told me to come with her. I needed no further urging.
She took me into a dressing room. As soon as the door was closed she grabbed me around the waist and pulled me to her. She planted a big kiss on my lips and stuck her tongue in my mouth, I put my arms around her neck and we held that position, each of us exploring the other's mouth in turn. Finally she pushed me away.
"You look really pretty today!" she said to me.
I blushed and thanked her. Then I told her she too was beautiful.
"Let's get you out of those clothes and into your bridesmaid dress!"
I slipped my sundress over my head and she indicated I should remove my shoes as well. Then she removed the dress from a garment bag hanging on a hook and lifted it over my head. I put my arms through the sleeves and she turned me around so she could zip it and tie the sash into a big bow. The dress was lavender and had an empire waist with a square collar, showing some cleavage. The sleeves were puffy and there was a built in white petticoat. She had me sit and helped me put on the shoes which were sandals with 4" heels and dyed to match the dress. Then she told me to stand and made a few adjustments before leading me to a mirror. The dress was beautiful. The lace hem of the petticoat showed beneath the dress.
"It's a perfect fit!" she declared and suggested I go out and show my mom how it looked.
Alison, Heather, and Lori were already waiting for me, also in their bridesmaid dresses. Mom oohed and aahed and insisted that the four of us pose for a picture. She positioned us the way she wanted, took out her cell phone and snapped a few pictures. Finally, we were told to change into our street clothes. Ashley took my hand and led me back to the dressing room. She helped me remove the dress and while I was taking off the sandals, she hung it the garment bag.
Then she shocked me by removing her dress. With both of us in our bras and panties she grabbed me and hugged me. We exchanged saliva for awhile and she led me over to the sofa. Her hand wandered to my groin and she grabbed the top of my pantyhose and panties, pulling it down to my knees and freeing my cock, which was already quite hard. I ran my hand down to her crotch and was shocked to find a bulge that didn’t belong. My first reaction was to pull my hand back. I looked in her eyes and she looked very sad. I was so turned on, however, that it didn’t really matter to me, so I pulled her panties down and began to stroke her. We kissed while stroking each other. Then she pushed me onto my back and turned herself so her cock was over my mouth. She took my cock in her mouth and pushed her erection against my lips. Reluctantly I opened my mouth and not too gently, she shoved it in. We were both very turned on. She came very quickly and as soon as her cum hit my tongue I ejaculated. We swallowed each other’s seed. It would be much later before I reflected on what we did, that I had in fact sucked cock. We cuddled for awhile and kissed a bit more. It was a very pleasant interlude.
The wedding weekend seemed to come very quickly. The wedding was to be in a hotel and the whole family would be staying there for the weekend. There was a rehearsal dinner on Friday night; the wedding would be on Saturday night, and a farewell brunch for out of town guests on Sunday morning. This would be the truest test of my ability to pass as a girl.
At the rehearsal dinner were just the two immediate families and the bridesmaids and groomsmen. Presumably everyone there knew of my true gender so I thought I could relax. I wore a simple sleeveless dress that stopped just above my knees and sandals with two inch heels. My hair was in a high pony tail with tendrils hanging on either side of my face. It was still disturbing to me how easy it was for me to be made to look like a girl.
Jared, David’s cousin, who would escort me in the recessional sat next to me at dinner and seemed very interested in me. I wondered if he was gay or had not been told who I was. It was pleasant talking with him and any nervousness I had disappeared. He gave no indication that he knew I was a boy and I wondered if that would cause any problems if he found out. But the evening ended with no embarrassment for which I was thankful.
The next day all females in the wedding party, including yours truly, were treated to a spa day; including hair styling, manicures and pedicures. With my hair not quite reaching my shoulders, Becky, the stylist, trimmed it and had it framing my face with bangs. My hair had a natural wave to it. On a girl it would have been quite pretty. Seeing it on me gave me a sick feeling. I thought that I would have to shave my head to look like a boy again.
My finger nails were given acrylic extensions and painted lavender to match the bridesmaid dress I would be wearing. My toenails were painted the same color.
Mom and Dad had taken a two bedroom suite in the hotel. They stayed in one bedroom and I slept in the other. Jordan was in the bridal suite and Alison was staying with Jonathan, her long time boyfriend and high school sweetheart. When we returned from the spa, I was grateful dad was not there. Mom had me put on a shower cap to keep my hair dry and insisted I take a bath. She put some bubbles in it. For a moment I thought she would insist on bathing me, but merely warned me not to get my face or hair wet.
“Caroline, I will lay out your clothes. Will you need any help dressing?
“No mom. I can dress myself.”
“Good, I will get dressed and then go help Jordan. I’ll see you before the ceremony.”
She gave me a hug and kissed me on the cheek. Then she left me to fend for myself in the bathroom. I smelled like flowers when I got out of the tub. I quickly dried myself and went back into my bedroom. As promised, my underwear was laid out on the bed, my dress hung on the closet door and my shoes were on the floor under my dress. On the bed was a lavender set consisting of bra, panties and a garter belt. All were ultra feminine covered with lace. She had also left me two pairs of stockings. I had not seen any of it before. I focused on the evening being my last one as a girl and proceeded to get dressed.
I had been dressing like a girl enough so that none of the clothes presented a problem except for the zipper on the dress. I called out to my mom.
“She is not here Caroline. It is just the two of us. Do you need help?”
It was my dad. I had tried to spend as little time with him as I could during my masquerade. I hated his seeing me dressed like a girl, but knowing I had no other choice, I went out to the living room where he was sitting.
“Daddy, please zip me up.”
I had been addressing him like that, since the whole masquerade started. I guess it was because Jordan and Alison addressed him that way. He zipped me up. While I was tying the sash into a bow, he started to say something, but stopped. I looked at him with a question in my eyes.
“Kevin, please sit down.”
I was stunned. It was the first time I heard my real name since my feminization had started. I sat down on the sofa. Dad pulled up a chair and sat opposite me.
“Kevin, I am really sorry about all this. I probably should have stopped it before it started but I really didn’t think your mom was serious about your masquerading as a girl. Once it started I was powerless to stop it. You know your mother. When she makes up her mind about something she becomes an irresistible force. I am truly sorry.”
It was the last thing I expected him to say and I can’t say I was not touched by his apology. I also realized he spoke the truth. There was no way he could have prevented any of it. I smiled at him and told him that I understood.
“May I have a hug?” He asked me.
We both stood up and he put his arms around my waist and pulled me to him. I put mine around his neck and he hugged me tightly. He hadn’t hugged me like that in years. It did not escape me that it was the way he hugged my sisters and it felt good. I was overcome with emotion and fought back tears, not wanting to ruin my makeup. Finally he let me go and he had a big smile on his face. I smiled back at him.
“You do make a pretty girl” he said causing me to blush. “Do you want to watch the ballgame till it’s time to go downstairs.”
I nodded and for the first time in a long time we did some male bonding, despite the fact that I was wearing a pretty lavender bridesmaid dress with the assorted lingerie.
Finally it was time to go. I put on my shoes (they were lavender sandals dyed to match the dress with 4 inch heels). He took my arm in his and escorted me down to the anteroom where Jordan and the rest of the attendants were waiting.
The wedding ceremony went off flawlessly and Jordan was a beautiful bride. Seeing the way Jordan and David looked at each other, there could be no doubt they were very much in love. With all my heart I wished them the best and looked forward to someday being an uncle.
Mom had made it clear to me that I would stand out if I were a wallflower and so was required to accept invitations to dance. After all, she said, how would it look for one of the bridesmaids to be sitting alone and not enjoying the party?
I didn’t have to worry about finding dance partners since Jared stayed close to me the whole evening and danced most of the dances with me. He was actually quite nice and under other circumstances I might have liked to get to know him. Others I danced with were not so nice and my bottom was pinched more than once. I thought that if that is what girls had to deal with, I was happy I was not one of them.
I did have one dance with my dad. It might have been very awkward, but after our conversation in the hotel room, I just relaxed and let him lead me around the floor.
The worst moment occurred on a trip to the ladies' room. I had scouted out a family rest room with a single stall and locking door. It was around the corner from the other restrooms and out of sight from the hall where the party was. It gave me some privacy for which I was grateful.
But as I opened the door to leave the restroom there were two girls standing there blocking my way. They were enormous. Though they were about my height, they each must have weighed close to twice my 140 pounds.
I tried to go around them, but one of them pushed me in the chest and I fell backwards into the restroom. They walked in and closed and locked the door. I scrambled to my feet, but I was frightened.
“Where do you think you’re going sissy boy?”
“Wh..what do you mean?”
“We know you are a fairy who likes dressing up like a girlie girl.”
I tried to bluff my way out of it.
“You don’t know what you are talking about!”
I tried to go around them, but one of them grabbed me and pushed me back. I barely managed to keep my balance.
“Wh..what do you want?
“For starters, lift up your dress and show us what you’re wearing underneath.”
I hesitated. That was about the last thing I wanted to do.
“Now sissy boy! Or we will do it for you!”
I could feel the tears coming and I couldn’t hold them back. I slowly lifted my dress, revealing my lace trimmed lavender panties and garter belt.
“Where is his cock? Are you sure she is a boy?”
“Pull down your panties, sissy boy!”
“Please, let me go. I won’t say anything.”
“Do as I tell you or I will pull them down myself.”
I slowly pulled my panties down with one hand while holding up my dress with the other. My penis, which I had tucked when I put my panties on now dropped along with my balls.
The girls laughed at me.
“Not very big is he?”
“Maybe that’s why he thinks he’s a girl.”
They both laughed at that. By now I was openly crying.
“Now play with yourself, sissy boy!”
I started stroking myself. They laughed at me and made crude comments. They teased me about my supposedly small penis. Despite the humiliation I felt my cock got hard. They told me to cum. I didn’t want to under those circumstances but I feared them and soon I spurted my semen onto the floor. When I looked up I saw they had their cell phones out and were taking pictures.
“That will teach you to steal my boyfriend”.
“What do you mean, your boyfriend?”
“Jared, you sissy bitch. We will see how much he loves you when he finds out what’s between your legs.”
They continued laughing as they walked out of the restroom. I pulled up my panties and sat down in the stall and cried. I heard banging on the door and Jared’s voice calling me.
“Caroline, are you alright? You’ve been in there a long time.”
“Yes, just a minute.”
I was still crying. I quickly got some paper towels and wiped my semen from the floor. I opened the door and he rushed in. He saw that I was crying and before I could say anything he put his arms around me and hugged me.
“Jared, you have to stop those girls. They will ruin you.”
“What do you mean?”
I knew I had to come clean to him and tell him the truth about me. He didn’t deserve to be scandalized by those bitches.
“Jared, I’m not what I seem to be. I’m really a boy. I’m Jordan’s brother.”
“I’ve known you were a boy the whole time. Mrs. Kline, David’s mom, asked me to watch out for you. At first it was just a favor to her, but after talking with you last night I realized how sweet you are and it was more than a favor, it has been a pleasure for me.”
“But, I don’t understand. Why have you been so nice to me? Are you gay?”
“No, I don’t think so, but when I look at you I see a very nice, very pretty girl who seemed like she could use a friend. I liked you Caroline, from the moment we met last night. And I think you like me too.”
“I don’t know what to say.”
“Don’t say anything. Clean yourself up and fix your makeup.”
“They took pictures. The will ruin you.”
“I will handle those bitches. And we will continue to enjoy the party. How does that sound?”
“It sounds good to me.”
He kissed me gently on the lips, smiled at me and left me to fix myself up.
The kiss gave me goose bumps and confused me. I had never been interested in guys, but I wanted Jared to kiss me again. I tried to shake it off and clean myself up. It took me about 15 minutes to repair my makeup and Jared was waiting for me when I left the restroom. He showed me 2 SIM cards which he had confiscated from their cameras. He broke them in half and deposited them in a trash can. Then he took my hand and led me back to the party. The girls were giving me the evil eye when we walked back into the room and instinctively I moved closer to Jared.
We danced together for the last few songs. During the slow songs we danced closely and I enjoyed his holding me like that. I almost forgot I was a boy during those songs. With his holding me so tightly I could feel his erection against me. It excited me and confused me knowing I was turning him on like that.
When the party finally broke up he took me to an alcove where we could be alone. We hugged closely and I could feel that he was real hard. This time when he kissed me it was full of passion and I returned his kisses with an equal amount of passion. His hand caressed my hips and then my ass. My cock was straining to get out of its panty prison, but with it bent back between my legs it became very uncomfortable. Still, I was not ready for him to stop. We exchanged phone numbers and email addresses and gave each other a last kiss before saying good night.
For brunch and the ride home I wore a simple sundress with spaghetti straps. Underneath I wore a bra and panties and my shoes were flat sandals. I looked forward to going home and getting out of the feminine clothing I had been wearing for the last couple of months.
Mom, dad, and I sat with Alison and Jonathan for breakfast. Jared came over and asked if he could sit with us. I was pleased and he sat down next to me. Throughout dinner he would grab my hand under the table and squeeze it or pat my thigh. I didn’t analyze it and just enjoyed his attention. With breakfast over we were going to head home. He grabbed my hand and led me away from the family. I could feel their eyes on us.
“I really want to see you again Caroline. I intend to call you very soon.”
Then he leaned over and kissed me. It was a soft, gentle kiss on the lips and lingered for several moments. He smiled at me as he said good bye. I watched him walk away wondering what I was going to do.
I walked back to my family. Dad had completed checking out and we were ready to leave. Alison hugged me and whispered in my ear.
“It looks like you made a conquest, little sister. And it would appear he is a keeper.”
She smiled as she said it. She was not teasing me. It was a warm loving look she gave me. I was surprised when Jonathan also hugged me. Normally we just shook hands. They had ridden to the wedding together and took off, telling us they would see us at home.
During the ride home I thought about all that had happened to me during my time as a girl. I had received my first blow job and it was awesome. I had also given a blow job and surprisingly enough I didn’t hate it. Actually, to be perfectly honest, I enjoyed it. I wondered if I were really gay.
Then there was Jared. I did not know what I would do about him. I had never wanted to dress like a girl nor was I interested in guys, yet here I was contemplating being a girl with him. It was so confusing. I kept asking myself if I really wanted to go back to pants. The thought of going to school as a girl and having all the kids tease me, or worse, strengthened my resolve to give up being a girl. I had been happy before all this had happened and I would be again. I would have to blow off Jared if he did call me.
When we finally got home my ordeal was over, or so I thought. I still had a closet loaded with dresses, skirts and tops, girls’ shoes, drawers filled with panties, bras, nylons, and of course the bridesmaid dress. I wondered what mom was going to do with all those clothes.
Mom asked me if I wouldn’t stay dressed as a girl until bed time. Then she would remove my breast forms and I could sleep in my boxers and a t shirt as I usually did before all this. It was a request, not an order. I had grown closer to her since that first day in a dress and I thought a few more hours were not going to make any difference so I agreed. Dad and I decided to watch a ballgame together until dinner.
Alison called us and told us she would be late, and to have dinner without her. Mom did not feel like cooking so we ordered in Chinese food, our favorite. Just as we finished dinner Alison and Jonathan came home. Alison was obviously excited about something.
“Mom, dad, look!” she screamed as she held out her hand.
On her ring finger was a diamond engagement ring.
“Jonathan asked me to marry him and I accepted. We want to get married in the fall.”
I closed my eyes and sighed, thinking “I guess I won’t be sleeping in boxers tonight.”
As I crawled into bed that night, I was wearing a short white sleeveless cotton gown with lace around the armholes, at the hem, and adorning the buttons on the bodice. I also wore white cotton panties. Any thoughts I had of giving up being of being a girl dissolved. I admitted to myself, for the first time that I really liked sleeping like this. The last thing I remembered as I drifted off to sleep was “I hope Jared calls me tomorrow.”