Abby, Jeremy, and Katie

Karen Jensen

The idea for this story came from a conversation I had in chat room 15 or more years ago. It has been rattling around in my head for some time now. I was talking to a person who was supposedly the mother of 2 teenage sons who she forced to dress as girls as punishment, even taking them in public so dressed. It was an interesting conversation which sounded more like a story you might find on one of the TG story sites. While the idea came from this person I chatted with, the plot is my own idea. This story 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.

This story includes some forced cross-dressing and some sex. If this offends you, it is not the right story for you to read.

I want to thank Annabelle Brito for reviewing and making suggestions that I believe have greatly improved the story.

This story 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.

Jeremy:

My mother, along with her sister, owned a bridal wear shop. I would go there after school and do my homework in the back room. The store was open 6 days a week, so mom would have every other Saturday and every Sunday off. When she had to work on Saturday, she had a neighborhood girl babysit for me until I was 12, when she trusted me to be home by myself. My story starts when I was 17.

Abby and I were lying on my bed, kissing and caressing. We were both fully clothed. She had been my girlfriend for a several months. While we had engaged in mutual masturbation, and I had spent some time playing with and sucking on her beautiful breasts, we had gone no further. She made it plain to me that there would be no intercourse since she was saving herself. For what, she did not say, but that was ok with me. To be perfectly honest I was a virgin and a bit nervous about having sex. I was satisfied with what we did and felt extremely fortunate to have a girlfriend as beautiful as Abby.

She had been recruited to play basketball for St. Ann's, the high school we both attended and this was her first year there, though she was already a junior. She was a star player, destined for a college scholarship.  At 5’10”, she was 3” taller than me. The height difference never bothered either of us. We met and started dating during the summer when we were both attending summer school. We were assigned as lab partners in biology and became quite friendly. I asked her out after a few weeks and she accepted. We had been dating ever since.

I was running my hand up under her short skirt when she sat up suddenly. She pointed towards my closet and said "what's that?"

I looked over and groaned, thinking to myself this can't be happening. My closet door was slightly ajar and a dress was clearly on display.

"Is that a dress?"

Not waiting for an answer, she pushed me off of her, stood up, walked over to the closet, and slid the door open all the way, putting on full view, my several dresses, skirts, and blouses, hanging there neatly.

"Why do you have girl's clothing in your closet?  Are they yours? Do you like dressing as a girl?"

I felt my face turning red. I tried to speak but nothing came out.

"Answer me Jeremy!" Her tone of voice softened.
"I won't hold it against you, but I want to know."
"Yes, the clothes are mine but It's kind of a long story" I found my voice.

She walked back to the bed and sat down next to me. She kissed me on the cheek and put her hand on my knee.

"I have time. Tell me!"
"The clothes are mine. And no, I don’t really like wearing girls’ clothes."
"If you don’t enjoy it, why do you do it? Does some body force you to wear girl's clothes?"
"Yes, my mom."

I started to cry. Abby put her arm around my shoulder.

"It's ok. I just want to know what's going on with my boyfriend."

Abby:

I liked Jeremy, a lot. He was gentle and considerate, maybe a little bit effeminate as some of my girlfriends had implied, but it was cool with me. I was no virgin, nor was I a slut. I had dated my share of jocks and frankly, they did nothing for me. I had even had a few girl on girl encounters, and while I was attracted to pretty girls, it wasn’t enough. Jeremy was the first boy I dated who was more brains than brawn and I wasn’t sure how I was going to like it. He was gentle, kind, and very considerate. Not a macho bone in his body and I found I really liked that. I vowed to myself that when I agreed to date Jeremy, there would be no intercourse, until I could see where the relationship was going. Hence the story I told him about saving myself. He had no idea I wasn’t the virgin I pretended to be.

Now, to be perfectly honest, I suspected he wore panties. I had masturbated him, and while I never saw his underwear, I could feel it. Though they were cotton, they felt thinner and more delicate than your standard men’s briefs. Frankly, the elastic on top felt like that you find on girls panties. When we came to his house after school that day, I checked his drawers while he was in the bathroom and found a collection of panties that would be the envy of any girl. Then I looked in his closet and saw his skirts, dresses, etc. The idea that he might like dressing as a girl actually excited me, so I left his closet door ajar with a dress sticking out and positioned myself on his bed so I would be looking in that direction when he came in. I hugged him and pulled him down on top of me so he would not be looking towards the closet. I wanted him to think he left it open to see his reaction.

Jeremy:

“It started when I was 10, as punishment.”

”What did you do?”

“I stole some video games, or at least I tried to. I got caught and the police brought me home.”

“It wasn’t the first time I was in trouble, but it was the worst, since the police were involved.”

“So why did she dress you like a girl?

“She wanted to get me away from the gang of boys I was hanging with. Stealing the games was kind of an initiation, which I obviously failed.”

“And you clearly weren’t anxious for anyone to find out about wearing skirts.”

“No. She made me dress like a girl for two months, every day, all day, except on school days and even then I wore panties and a camisole. I was petrified someone would find out, but if anyone did they never said anything.”

“So why are you still dressing like a girl?

“While I was being punished, my grades shot up. I mean I couldn’t play with my friends so I studied more and completed all my homework on time. When the punishment was over my grades started falling, so I was back in skirts and panties.”

“So did you continue dressing like a girl every day?”

“No. Sunday was what mom called my “Girl day”. And any other day she so designated.”

“Does anyone else know?”

“Other family members also know since I often have had to go to family functions in a dress.

“Even now?

“Yes. If the function falls on a “girl day”, I dress like a girl.”

“That must be hard.”

“It is. I get teased a lot by my cousins. The girls aren’t too bad now, but the boys will have nothing to do with me.”

Abby:

I knew I should have been appalled at his treatment and I guess a small part of me was, but mostly I was turned on. More turned on than I ever was. My panties were soaked and I was sure my skirt was also wet.

We sat there in silence as I processed all he had told me. I wanted desperately to see how he looked made up as a girl. I felt a bit guilty about what I was going to do, but I knew I kind of had him over a barrel, so to speak.

I went to his closet and pulled out a light blue dress with white polka dots. It was fairly short.  I pulled out a pair of blue sandals that went with the dress.  Then I opened his underwear drawer and pulled out a pair of panties, a bra, and pantyhose.

“Abby, what are you doing?”

“How do you pad your bra?”

“I..I have breast forms…in the bottom drawer.”

I opened the drawer and found them there. They were obviously of a high quality. With them was a tube of adhesive. I pulled out the forms and the adhesive. I handed everything to Jeremy.

“Jeremy, put these on. I want to see how you look as a girl!”

Jeremy:

We sat there in silence for I don’t know how long. I was afraid to look at Abby. Was she doing this to humiliate me? I wondered if it was over between us and if everyone would know why.  I was stunned when she went to my closet and then opened my underwear drawer containing my girlie underwear. I wondered how she knew what drawer to go to, however, before I could think to ask her. she handed me everything and told me to get dressed. I was afraid to say no, though the last thing I wanted was for her to see me dressed up.

“Do you do your own makeup?” she asked me.

“Yes” I whispered.

“Good! I want to see the whole package.”

She left my bedroom and closed the door behind her. I lay down on my bed and cried. I did not know what to do. If I dressed for her she might laugh at me and leave. If I didn’t dress she might leave anyway. And in either case, I did not know if my secret was safe with her.

I realized that she hadn’t laughed when I told her my secret. In fact, she seemed quite sympathetic, so I decided it would be best if I complied with her request. I quickly stripped and put on the clothes she laid out for me. The dress she picked out was one of my shorter ones and was a good 5 inches above my knees.  I took my makeup and went into the bathroom to apply it. I had become quite adept at it and in a short order I had transformed my face to that of a teenage girl. I freed my hair from the low ponytail I wore. I put it into a high ponytail and tied it off with a blue ribbon. I applied my makeup, added earrings, a necklace and a couple of bracelets. I took a deep breath and walked out to the kitchen where Abby was sitting sipping on a soda.

Abby:

I was not prepared for what I saw when he walked in. His head was down, as if he were afraid to look at me. If I didn’t know better I would have thought it was a pretty teenage girl standing before me. While I always thought he was somewhat feminine and maybe a bit girlish looking, I never expected him to be so beautiful. I was turned on earlier, but now my hormones went into overdrive. I wanted nothing more than to grab him, kiss him, and throw him down to make passionate love. I somehow managed to keep my emotions in check. I realized that this could be so much more than mere sex with this pretty girlie boy.

“Wow Jeremy! You are a pretty girl.”

“Thanks. I guess” he whispered so I could barely hear him. “May I change now?”

“Oh no! Come sit next to me

He did not move. Silent tears started falling.

“Do you have girl’s name you use?’

“K..k..Katie” he sobbed.

“Very nice! Look at me Katie!”

He looked up. I can’t describe the feeling I had, realizing how much power I had at that moment. Still, I liked Jeremy and felt a bit guilty for putting him in this position. I stood up and walked over to him. I put my arms around his waist and squeezed him. He hesitated for a moment and responded, putting his arms around my shoulders. It did not escape me that we had reversed the standard positions of hugging between a boy and girl.

“Don’t worry Katie, it will be our secret.” I whispered.

He burst out crying and I just held him till he was able to gain control. His mascara was a mess. I laughed at his raccoon face and told him to repair his makeup and come back. When he returned I had him sit near me. I wanted time to process this revelation and understand why I was so turned on by my pretty boyfriend.

It was getting late and I had to get home. I leaned over and kissed him on the cheek

“I’ll see you later for our date. Pick me up at 7:00?”

He nodded and I left.

Jeremy:

My emotions were all over the place. Abby had not laughed at me and seemed to be accepting me.  I  had to tell my mother and was not sure how she would react to Abby’s finding out. I knew she would not be happy and I would probably be in for additional punishment over and above whatever Abby might do. Resigning myself to that, I saw no point in changing my clothes and stayed dressed as Katie till my mother came home.

As I predicted, she was angry that Abby had found out. She told me I would be in skirts for the next 2 weeks and told me to pray that that would be the worst of it. There is no telling what would happen if Abby decided to reveal my secret.

I called Abby to tell her our date was off.

“Why Jeremy?”

“I am being punished for letting you find out about my dressing like a girl. I am only allowed girls’ clothes for the next 2 weeks, except for school.”

“Are you grounded also?”

“No, I guess mom figures that I won’t want to go anywhere while dressed like a girl. She is right about that.”

“That’s ok. I don’t mind being seen with Katie.”

“You can’t be serious.”

“Why not?”

“What if someone we know sees us?”

“I’ll introduce you as my best girlfriend. They will never know the difference.”

“I..I don’t think I can do it.”

“Listen to me Katie! You have, by your own admission been out in public with your mother. You can certainly go out with me. Now wear something pretty. I am taking out my best girlfriend tonight! I will be at your house at 7:00!””

Before I could respond she hung up. What a mess I had created by not shutting my closet door.

“So what will you do, Katie?” my mother asked me.

“I don’t know mommy. What do you think I should do?”

“I think you had better go out with her. It would not be wise to make her angry. There is no telling what she will do. She is probably very upset to find out her boyfriend likes to wear pretty clothes and is just as pretty as she is.”

“But I don’t like it!”

“Well, that is beside the point. I think you would be wise to go out with her. Now come along and I will help you get ready.”

 “Yes mommy.”

Mommy picked out a new dress she had just bought for me which I had yet to wear. It was a white sleeveless skater dress with a short flare satin skirt, a halter neck top, and white lace covering the bodice from the waist to the neck. It was very feminine and putting it on just added to the humiliation I always felt when dressed up like a girl.

I paired it with white panties and a white strapless bra. I also wore a white panty girdle to keep my package in check. I normally did not wear one, but an erection was a certainty being on a date with Abby and I had to hide it at all costs.  It was a warm evening so I decided to forego hose and wore white strappy sandals with 2 inch heels.  Mommy had glued on my breast forms so they would not come off in case we “played”. When I looked in the mirror I saw a pretty young woman. I idly wondered if mommy would insist on my girl time if I were an ugly girl.

 She made sure I had condoms in my purse as well as lipstick, and mascara. She also put a couple of tampons in. I didn’t understand why she did that and all it did was to add to my humiliation. I was ready to leave about 15 minutes before Abby came which allowed me time to think of all that could go wrong and increase my nervousness.

Abby:

I was very excited when I left Jeremy. I wasn’t sure why, but seeing him look so pretty and vulnerable in the dress really got me hot. I was so turned on when I got home that I went to my room and masturbated, having several orgasms before I could calm down.

When he called to cancel the date because he was being punished, I wanted to see him even more. Rather, I wanted to see Katie, and so I pushed him. I hung up before he could refuse me and now all I could do was hope she would be waiting to go out with me when I arrived at her door.

I decided to wear pants and a man tailored blouse. I also refrained from wearing any makeup. I was not trying to look like a guy (No way could I pass as one) rather I wanted to look bland compared to Katie. Having seen her wardrobe, I knew she would look ultra feminine. I was on edge the whole time until I got in the car to go pick her up.

I took a deep breath, said a short prayer, and rang the bell. When the door opened I was greeted by a vision in white. I reacted by grabbing her, hugging her and giving her a passionate kiss on the mouth. What I wanted to do was to make love to her, but I would save that for later. I had thought to shove a couple of extra pairs of panties into my purse, since I was hoping I would need them. Katie responded to my kiss and hugged me back and I knew I would need them.

Reluctantly we separated and I greeted his mother. She returned my greeting with a smile, but it was not a friendly one. I understood that she did not know what my motives were.

I grabbed Katie’s hand and led her to my car. I held the door open and was impressed at her skill in getting into the car in a short dress. Obviously she was well schooled in acting like a girl. Before closing the door I leaned over and kissed her. I wanted her so badly, but I still wasn’t sure how she felt. Hopefully all would become clear as the evening progressed

Katie:

I had never seen Abby without makeup and wearing such nondescript clothes. In my mind, however, she was still beautiful and she almost knocked me over when she grabbed me. Again she put her arms around my waist, pulling me towards her. I put up no resistance and instead wrapped my arms around her neck as we kissed. After greeting my mother, she led me to her car, holding the door open for me as I got in. This was not before my mother reminded me of my midnight curfew.

 “Abby, I feel a bit over dressed. If you had told me….”

“It’s ok Katie. Tonight you will be my princess. Just sit back and enjoy the ride.”

I blushed at her comment. Through all the years of my cross dressing, I had never been referred to as a princess, and was not sure I liked it. Still, I was with the girl I loved. I hoped and prayed the evening would not end in a disaster.

She took me to a nice restaurant about a half hour out of town. She thought that it would be less likely to meet anyone we knew. Even though she had a reservation, we were required to wait about 15 minutes. While sitting in the waiting area, a couple of guys sat down across from us and started flirting with us. This had happened to me once before when I was with my mother and she quickly discouraged them. To my horror, Abby flirted back with them and for a moment I thought she would accept their invitation to dine with them. She put her arm around me and told them we really weren’t interested in men. Needless to say, I breathed a big sigh of relief.

We had a lovely meal to which she insisted on treating me. It was still early when we left the restaurant.

“Where are we going now?” I asked as she headed back towards town.

She smiled at me and told me it was a surprise. I was feeling really good and leaned back, trusting her. While I was not happy about being out with her while wearing a dress, it was kind of nice to be pampered the way she was treating me.

We drove into town and she pulled up in front of a high rise, where she parked.

“Where are we?”

“My sister lives here. She is out of town tonight and I have the key.” She gave me a big smile and winked at me. I felt myself blush.

Abby:

Flirting with the guys in the restaurant was kind of mean on my part. I wanted to see how Katie would react. I never had any intention of exposing her to any unnecessary risk, but it was kind of fun to see how nervous she was. Does this make me somewhat of a sadist?

Knowing I had the use of my sister’s apartment, I had decided that tonight was the night to consummate our relationship. The horniness I felt since I first saw her in that blue dress this afternoon had not abated despite the orgasms I gave myself. I wanted Katie, and I hoped she wanted me just as badly.

I know it is very cliché, but I poured us each a glass of sweet wine hoping to loosen her up. I was prepared to take no if she refused my advances. After a couple of sips and some small talk I took the glass from her hand and leaned over to kiss her gently on the lips. She caressed my face with her hand and I moved closer so our bodies were in contact. I penetrated her mouth with my tongue and she eagerly sucked on it. I took this as encouragement and moved my hand up under her dress, gently running it up her leg and caressing her inner thigh.

I rubbed the front of her groin and was mildly surprised I could not feel her cock. I realized she was wearing a panty girdle, so I grabbed the top of it, along with her panties and pulled them down to her knees. Her cock popped up and was instantly hard. I smiled at her and resumed kissing her sweet lips. I wanted to fuck her, but I had other ideas first.

I lifted her dress and gently stroked her once or twice. She twitched at my touch. I licked her balls and than her shaft. It was like a steel rod. Then I took her into my mouth. This was not my first time and I had had much bigger cocks, but in my mind hers was perfect. I easily swallowed her and she erupted in my mouth. I was surprised at how quickly she came and at the quantity. I guess she hadn’t masturbated in awhile. I swallowed most of it, holding a bit in my mouth. It was sweet as Katie was and I was determined to share it with her before allowing her to return the favor.

I quickly shed my clothes, crawled up her body and kissed her sweet lips. I forced my tongue in her mouth, feeding her some of her own semen. She tried to resist, but I was on top and had her pinned. Giving in, she swallowed it. We kissed awhile longer, sucking on each other’s tongue. I was incredibly horny and needed relief. Holding her arms down so she couldn’t move, I scooted up positioning my pussy over her mouth. Gently, I lowered myself and whispered to her that she should now please me.

She went to work flicking her tongue in and out of my vagina. She played with my clit. She clearly had not done it before, but following my directions she soon got into it and it didn’t take long for my first orgasm. I told her to continue and had several more before I came down. We snuggled for awhile and I started caressing her. She responded and before too long she was again erect. Not wanting to waste it, I quickly mounted her. I don’t think she was expecting that and tried to stop me to put on a condom. Since I was on the pill, and knew she was a virgin, I had no worries and soon experienced several orgasms before she finished.  I briefly thought of having her clean me out, but decided I had given her enough of a shock for one night. There would be more opportunities for her to learn.

Katie:

I hoped when she took me to her sister’s apartment it meant we were going to have sex. Her wink at me in the car confirmed it, at least in my mind. I never knew how good it could be. I had heard guys talk about getting blow jobs, but it was impossible to know what it was really like without actually having one. Now that I knew, I definitely would want more. I was not happy when she kissed me and forced my own cum into my mouth. It didn’t taste that bad, but I thought it was kind of gay. I really had no choice though, since Abby was holding me down and I couldn’t move her. I wondered if she really was stronger than me.

I didn’t think about it again until much later since she was soon sitting on my face and treating me to my first taste of oral sex. She tasted so sweet and I enjoyed pleasuring her. We snuggled for awhile after that and before too long she had me hard again. We fucked like a man and woman should. Well, actually, I was on the bottom in the female position, but still, my cock was in her pussy which was a first for me. I was no longer a virgin.

Afterward we lay together with our bodies intertwined for quite some time. All too soon it was time to get dressed so I could meet my curfew. I had to admit, although I had spent the evening in a dress, it was the best time I ever had in my life.

Abby:

It was very tempting for me to call Katie the next day and try to see her, but I held back. The previous evening had been filled with many “firsts” for her and I thought she might need time to process and decide if she was ok with them. If I didn’t hear from her over the weekend, I would see her at school on Monday. Actually, I would see Jeremy, which I realized was not quite the same thing. I was not sure how I would handle it. He had made it plain that he did not enjoy dressing like a girl. I could only hope the events of the previous night would change his mind, at least a little bit.

Katie:

I tossed and turned for much of the night. My date with Abby had gone far better than I could have hoped. I normally did not masturbate while wearing girls clothing, and that included the nighties mommy made me wear, but thinking about our date made me so horny that I could not resist the temptation.  Despite having cum twice with Abby, I had no problem finishing two more times during the night and still woke up in the morning with an erection.

Despite that, in the recesses of my mind I wondered if the evening would have been so good had I not been wearing a dress. Certainly Abby was a lot more amorous with my being in a dress then she ever had been with me in pants. I knew I had to talk to her about it, but was not sure I wanted to hear what she would have to say. I did not want to continue being Katie, but if giving Katie up meant losing Abby, I did not know I would react.

We never talked over the weekend and when we saw each other at school, neither one of us brought up the subject. She was obviously very happy with my being Katie, and since I was to be in skirts for the next 2 weeks, I saw no reason to talk about it then. We did manage to get together at my house after school a couple of times and with my being dressed as Katie, there was more mutual masturbation. With the possibility of mommy coming home at any time, we could not risk having intercourse.

Abby:

I was hoping we would continue as we had on our date. I knew that if we were to go out over the next couple of weeks, it would be Katie I was with. I didn’t know if she would continue to date me as a girl. I hoped I could make her see how much fun we could have together as 2 girls.

We ate lunch together at school that week and talked in between classes, but the subject of our last date never came up. I think we were both too nervous to talk about it. Also, we had not made plans for the coming weekend, which was unusual for us. we did get together during the week and I made sure she was completely satisfied with our play. Finally, on Thursday, I asked her if she would go to a movie with me on Saturday evening. She seemed happy to accept my invitation.

Katie:

Going out as a girl was still very stressful for me. I wanted to be with Abby, but was kind of hoping we could stay in. My mom was going to be home as were her parents. She convinced me that at a movie there would be minimal chance of my being exposed, and reluctantly I agreed to go with her.

Since pants of any kind were forbidden when I was under petticoat discipline, I wore a short denim skirt and a pink sweater. As it was a warm night I skipped wearing nylons and wore sandals with 1 inch heels. My hair was brushed out and hung free at my shoulders. I knew I looked like a girl, but was still scared about being exposed.

When Abby picked me up she also was wearing a skirt and makeup. She was not attempting to make me appear the more feminine. For that I was grateful. She wrapped her arms around my waist and kissed me, none too gently. Her tongue immediately invaded my mouth and I sucked on it ravenously. I was happy I had remembered to tuck my penis back between my legs or the line of my skirt would have been ruined. With my mother there, we broke off the kiss all too soon for my taste.

“That is just at taste of what I have planned for later” she whispered to me.

Taking my hand she led me to her car and again, held the door for me while I sat and swung my legs inside. She leaned over and gave me a peck on the lips before closing the door. While I can’t say I did not enjoy the way she treated me, it did bother me a bit that we were reversing roles. I really wanted to be a man for her, not her girlfriend.

Abby:

I sensed that she was uncomfortable with my taking the lead role, but I felt the need to condition her to that. If our relationship was to continue, she needed to accept that I was in charge. I did want it to be fun for her, but the revelation I had about my own need for dominance was going to take precedence.

I selected an out of the way theater that showed foreign films, and as I expected, the theater was not terribly crowded. We managed to find an empty row near the back of the theater and took seats at one end, near the wall. That way we would not be in anybody’s view. I wasn’t planning on watching the movie very much. In fact, when we walked out of the theater I would have been hard pressed to describe the movie.

Katie:

I was grateful the theater was not crowded and no one there knew us. Abby picked an empty row and directed me to the other end near the wall. No sooner had the theater gone dark when she was all over me. Her arm went around my shoulder and we kissed. I put my tongue in her mouth and she sucked on it. I felt her other hand creep up my thigh and under my skirt. I was instantly hard. Nervously I looked around but could see no one paying us any attention. She pulled my panties down so she could grab my penis and started stroking me. Then she dropped to her knees and stuck her head under my skirt. She took my rock hard penis into her mouth. I felt her other hand caressing my ass and suddenly I felt her finger at my anus. She slowly slid it inside and I gasped. It was not something I was expecting, but it did feel good. I glanced around nervously, but no one seemed to be paying us any attention. She slowly moved her finger in and out of my anus. That with her sucking put me over the top rather quickly and I erupted into her mouth. When I had finished cumming she slid back onto her seat and leaned over to kiss me. With her tongue, she pushed the semen into my mouth and held her mouth over mine until I swallowed it.

“Did you enjoy that?” she whispered.

“Mmmm” I groaned, unable to speak.

We sat there for awhile and I ran my hand under her skirt only to discover she wasn’t wearing panties. She was already very wet and I stuck my finger in her pussy. She gasped and I moved my finger in and out, gradually quickening the pace. She came quickly but she held my hand there. She obviously wanted more. She came several more times before she allowed me to move my hand away. She kissed me deeply and resumed stroking me. I surprised myself by becoming erect again so soon after my orgasm.

She kept stroking me and once again I came. When she pulled her hand out from under my skirt it was full of my semen. She licked some off her hand and then offered it to me. She kept her hand near my mouth until I licked it clean. Her learning of my cross dressing seemed to cause her to become very dominant towards me, and I, in turn, very submissive towards her.  She took my hand and led me to the ladies’ room.

I cleaned myself up but my panties were soaked. Abby gave me a panty liner and feeling completely humiliated I put it in my panties. We then went back to the movie, though we really didn’t see much of it as we spent the time kissing and exploring each other.

Abby:

The evening went the way I hoped it would. Katie was very submissive and I was incredibly turned on by her response to me. I didn’t mean to embarrass her with the panty liner, but it seemed to be a good solution given that she wasn’t carrying an extra pair of panties with her.

I now had one more weekend to convince her to continue being my girlfriend. I could not envision a future for Jeremy and me together, but if he agreed to be Katie, the whole picture would change.

Katie:

I breathed a sigh of relief when Abby dropped me off at home. I had gotten through another date with her without anyone recognizing me or realizing I was not the girl I appeared to be. One more week and I can go back to being Jeremy and be a boy on our dates. I can hardly wait.

Abby:

I was quite happy with how our relationship was progressing. One more date with Katie, and more sex with her. I was hoping to have her associate sex with being feminized. I was determined there would be no sex with Jeremy when he was allowed to return to wearing pants. We were going out on Saturday night. I told her to wear a pretty dress but would not tell her where we were going.

Katie:

We were together after school at my house that week. Of course, I still had to change as soon as I got home. I should explain that my mom would come home at random times to check that I was wearing my girlie clothes. Punishment would be extended if I were not. So I always changed when I got home from school when being punished. Abby enjoyed watching me transform myself into Katie. Though I was greatly embarrassed doing it in front of her it really seemed to excite her.

Abby:

That week was great, at least from my standpoint. Watching Jeremy transform into Katie was a real turn on for me and I made sure to reward her for her efforts. We managed to spend every afternoon together that week. I didn’t know if I was in love or lust, but at that point it really didn’t matter to me. It would in the future.

Jeremy:

As I was getting dressed for our Saturday date, I hoped this would be the last time I would be a girl for Abby. I desperately wanted to be a man, though I wasn’t all that certain it was what she wanted. Still, since it would be our last date with my dressing like a girl, I decided to do what she asked and make myself as pretty as I could. I chose a short purple dress.  It had short sleeves and a straight skirt. With it I wore nude pantyhose and black shoes with 3 inch heels which would bring me up to her height. My hair hung loose on my shoulders. I had to admit to myself that I did make a pretty girl, but got no satisfaction from it. It only made it harder to exercise my masculinity.

Abby:

Katie never ceased to surprise me with her beauty and femininity. It was very hard to think of her as a boy. Still, I was not going to let her outshine me tonight so I wore a white lace dress with an A-line skirt and short sleeves.

I paired it with white opaque hose and white sandals with 3 inch pumps. I was hoping that tonight would convince her that her being a girl was not so terrible.

Katie:

Abby was a vision when she picked me up that night. With my mother at her store taking inventory, I was hoping we would have some time to fool around. Actually, I was hoping we would stay in, but after some heavy kissing, which required both of us to fix our makeup, Abby insisted we get moving. She would not tell me where we were headed, which made me a bit nervous.

We parked in a residential neighborhood with which I was not familiar. She took my hand and led me to a private residence. There was music and singing and I heard voices. I was nervous and scared.

“Katie, I would not put you in a position where you would be exposed and humiliated. Do you trust me?”

“Yes, I do.”

“Then come with me and don’t worry.

She rang the bell and when no one answered, she opened the door, which was unlocked, and we went in. There were many kids there. At first I thought it was just a regular teen party, but then I noticed something strange. I saw boys dancing with boys, girls dancing with girls, boys dressed like girls and girls dressed like boys.

“What is this place?” I whispered to Abby.

“It is an LGBT party. Before you protest, I know you’re not gay and don’t consider yourself to be transgendered, but give it a chance. I know most of the kids here, they are really nice, and if they do discover your gender, they will not judge. Ok?”

I nodded. I was starting to feel a bit of anger, but her words calmed me down.

“Come, let’s get a drink and I will introduce you to my friends.”

She handed me a cup of fruit punch and took one for herself. Before we could take a step we heard someone scream out her name. A pretty girl came up and hugged her, almost causing her to spill her drink. Abby hugged her back and then stepped away.

“Katie, this is Lisa. Lisa, this is my girlfriend, Katie.”

Lisa gave me a warm hug. She had a beautiful, friendly smile and I liked her immediately. Then she turned o Abby.

“Abby, I really need to talk to you. Katie, do you mind if I steal her for a few minutes?”

I shrugged my shoulders, but could feel myself getting nervous at being left alone with a bunch of strangers. Lisa grabbed Abby’s hand and started pulling her away. Abby looked back at me and mouthed “I’m sorry”.

I found a corner to stand in and sipped my drink while looking around. While many of the “girls” were obviously boys and vice versa, I couldn’t help but wonder how many were there whose true gender was not obvious. I finished my punch and was going to get another cup when a girl said hello to me. She was dressed in boys’ clothes with a boy’s haircut, but was clearly a girl. She was also at least 5 or 6 inches shorter than me in my heels.

“Hi, I’m Trish” she smiled at me.

“I’m Katie, nice to meet you.”

“And you as well. I don’t ever remember seeing you before.”

“That’s because I haven’t been here before.” I laughed. “I came with Abby.”

“Cool. So are you her girlfriend?”

“Yes, I guess so.”

“Would you like to dance?”

“Sure, why not.”

She led me out to the middle of the room where other kids were dancing and put her right arm around my waist to lead. Since she thought I was a girl, I saw no reason to dispute it and laid my left hand on her shoulder.

“So Katie, when did you realize you were lesbian?”

“Trish, to be perfectly honest with you I am not a lesbian. I’m actually a guy.”

I’m not sure why I told her that, but it seemed, at the time, the right thing to say.

“No way! You’re too beautiful.”

“Nevertheless, it’s true. If you don’t want to dance with me, I will understand.”

I started to back away, but she pulled me back.

“It’s ok. I like you even if I wouldn’t bed you.” She laughed.

We finished the dance and she thanked me. Then she went on her way to find a real girl.

Abby had been gone a long time and I started to worry. I was about to go look for her when I was stopped by a guy. He was at least 6 inches taller than me, even in my 3” heels.

“Hi, I’m Brad. And you are?”

“Katie.”

“Would you like some punch?”

He held out a cup to me.

“Yes, thank you.”

It tasted a bit different then the first cup, but was not unpleasant. We talked for awhile and without asking me, he took my hand to lead me out to dance. I quickly gobbled down the rest of my drink and followed him. It was a slow dance and when he put his arm around my waist I automatically took the girl’s position. He seemed like a nice guy and we chatted amicably while we danced. I started feeling a bit lightheaded and when he pulled me closer, I leaned into him as I was afraid of losing my balance. As he pulled me closer his hand slid down my back and grabbed my ass and caressed it. It felt good so I allowed him to continue. Suddenly I could feel a lump against my tummy, and it was growing. It took a few moments for me to realize it was his erection. I tried to push away from him, but he was too strong.

I hadn’t noticed that we had danced towards a door. I realized he was trying to take me to another room. I tried pounding on his chest with my fists but he just laughed at my pathetic attempt to break free.

“I’m a boy!” I screamed at him in desperation.

“So am I!” he laughed. “And I am bisexual, so this should be fun for both of us.”

He opened the door and started to drag me through into the other room. I tried to resist but he was much too strong.

I was screaming “No!” but he was ignoring my plea.

“Brad! Leave her alone, you bastard!”

Abby:

I hadn’t meant to leave Katie alone for as long as I did. Lisa was in crisis, having just broken up with her girlfriend. She was like a sister to me and needed to talk and cry with me. I didn’t think I could leave her. I heard a commotion and thought I heard Katie’s voice. That’s when I ran into rec room and saw Brad trying to pull her into a bedroom. I would allow that only over my dead body.

Katie:

It was Abby. Brad was distracted enough to loosen his grip and I pulled my arm free and ran to Abby. I was never happier to see anyone in my life. Abby’s yelling had attracted kids from the other rooms. Apparently Brad had a reputation and was asked to leave the party. He was somewhat inebriated, and it seems that he spiked the punch both he and I were drinking in hopes of getting me into bed.

Abby took me to into the bathroom and hugged me. I broke down in her arms. When I pulled myself together she took a cloth and washed my face. Then she repaired my makeup for me.

“Come on Katie. Let’s get out of here.”

I smiled at her and nodded. I was still shaken up and grateful nothing had happened. She apologized for being away from me for so long. Apparently Lisa had some kind of crisis and Abby was comforting her.

It was still early and neither of us wanted to go home. We decided to get some ice cream and went to a soda shop in the same neighborhood. She saw some kids she knew from her old school and we soon found ourselves sitting with a bunch of kids, boys and girls, who knew Abby. They seemed to accept me as the girl I appeared to be and fortunately, no one tried to hit on me. My emotions were still fragile and I don’t know how I would have reacted. They seemed like nice kids but I was still grateful to get away undetected.

When we got back to my house my mom was still not home. She had left a message on the answering machine that she would be very late. We grabbed a couple of sodas and sat on the sofa in the living room.

Abby:

I was about to make the biggest mistake of my life. I believed that I could love only Katie. I told her that I didn’t think I could be with Jeremy. I liked him well enough as a good friend, but he did not turn me on. I asked her if she could continue to be Katie for me even when her punishment was over.

She looked at me and I could see tears forming in her eyes. It didn’t take but a moment for me to realize I had hurt her. I knew in an instant what her answer would be and regretted immediately. I could not take it back. It was what I truly felt at the time.

Katie:

I felt like I had been stabbed in the heart. Tears welled up in my eyes and I made no effort to hide them. Abby had effectively ended our relationship and I was totally unprepared. She stood up and said she was sorry and left quickly. I sat there crying for a long time, before finally going to my room and to bed. Tomorrow was the last day of my punishment, something I had been looking forward to, but it somehow did not seem very important.

Abby:

It broke my heart to see her crying because of something I did. I tried to analyze how I could have handled it differently, but it came down to Katie turning me on and Jeremy not exciting me. Despite the pain it was causing both of us, I tried to convince myself it was all for the best. I cried all the way home.

EPILOG: 6 Years Later

Abby:

Jeremy and I saw each other at school after our breakup, but never talked. We just nodded at each other when passing in the hall. He graduated that spring and we didn’t see each other afterwards. I had another year to go and our girls’ basketball team made it to the state semifinals, the best they had ever done. I got a basketball scholarship and went off to college. I got my degree in finance and then my MBA. I landed a great job in our home town and moved in with Ashley, my sister.

I had dated quite a bit, both men and women, but could not find anyone I thought I would be happy with. I even managed to feminize a few boys, but they did not excite me the way Katie had and eventually those relationships ended. I was now focused on getting my career off to a good start and had no thoughts of dating anyone, at least for awhile.

Jeremy:

I never saw Abby after I graduated, which was just as well. It pained me every time I passed her in hall at school. I went away to college, but my heart wasn’t in it. I was alone and without friends and I dropped out after my first semester. I tried to find a job but was unsuccessful. All the decent jobs required more education than I had.

 I had always been good with numbers, so mom suggested that I take bookkeeping classes at night and work in her store during the day. That seemed like a good idea until she told me I would have to work as Katie. She said that girls don’t want to see men when they are trying on wedding dresses. When I refused, she told me I would have to leave unless I could find another job and contribute to the house. Having spent several months of job hunting, I came to the conclusion that I had no real choice and Katie was coming back in our lives. I worked the cash register in the store, since I obviously could not help with dress fittings. Then I would change my clothes and go to school as Jeremy. At least I was free to be me when I was not working. There were no more girl days imposed on me at home.

Abby:

Ashley was getting married and I was to be her maid of honor. It was an exciting time for our family. My mother drove us to the bridal shop to look for dresses along with her two best friends who were to be her bridesmaids. I immediately recognized the store as the one Jeremy’s mother owned and my heart skipped a beat as we went into the shop. I looked around not knowing whether or not I wanted to see him, but he was nowhere in sight.

We spent several hours trying on dresses. Finally Ashley picked the one she wanted and picked our maid of honor and bridesmaid dresses. We were all happy that they weren’t hideous and we would be able to use them for other occasions. They were marked by the seamstress for alterations. We were told they would be ready in two weeks, in plenty of time for the wedding.

As we were about to leave I glanced around the shop again and my heart literally stopped. Katie was working the register. She didn’t see me and might not have recognized me if she had. I had cut my hair short (which I hated) and was now wearing glasses. I wanted to say hello and hoped I wasn’t making a big mistake. I went to the register and waited for her to finish with the one customer who was there. I had an opportunity to look at her closely and realized she was more beautiful then I remembered. She had a professional manicure, her hair was done in such a way as to make it virtually impossible to comb in a masculine style, and her eyebrows had been shaped with high arches. When I looked at her face, however, I was taken aback. She smiled at the customer she was working with, but her eyes showed great sadness. My heart was breaking for her.

When she finished with the customer I stepped up to the register. She looked up at me and took a deep breath. It was clear that she recognized me.

Katie:

As a bookkeeper I generally worked in the back. When the shop got busy, as it did that afternoon, I would come up front and work the register, freeing the other women to help the customers. The last person I expected to see was Abby and it was a shock. All the old emotions flowed through me and for a moment I thought I would pass out.

Abby:

The old feelings I had for her returned. More than wanting, I needed to talk her, but not here and not then.

Katie:

“Abby?”

“Yes, it’s me.

I was speechless at that point. I had no idea what to say to her. Fortunately, she was not so tongue tied.

“Katie, can we meet some place when you get off work. I really want to talk to you, in private.”

“I..I..I’m not sure that is a good idea.”

As I said it I regretted it. A part of me wanted to talk to her, but another part was sure it would only result in more pain that I thought I had put behind me a long time ago.

“Please, Katie. I beg of you. ”

I hesitated and stared at her for several seconds. In my eyes she was prettier than ever and I could feel a lump in my throat.

“I..I get off at 6:30. Why don’t you meet me outside the shop then?”

“Great!” She gave me the smile that had captivated me those years ago.

The rest of the day went very slowly but 6:00 did come around and the store closed. I totaled up the receipts, prepared the night deposit, made the needed entries in the books and I was ready to leave. It was 6:30 exactly when I walked out of the store. Abby was waiting for me.

Abby:

She looked beautiful walking out of the store. But I felt the pain I saw in her eyes. She was clearly unhappy. Somehow I managed to refrain from throwing myself on her and wrapping her in my arms. We walked a couple of blocks to a hotel and went into the bar. We found a quiet table in a corner where we could chat. We each ordered a glass of wine and after it was delivered and the waitress left, she leaned back in her chair and looked at me expectantly. Suddenly I was very nervous. I had rehearsed what I was going to say and now had forgotten it all. I knew I had to speak from the heart. I had hurt her very badly 6 years ago and if I got hurt tonight, it would was what I deserved.

“Katie, why are you working at the store? And as a girl? I thought you wanted give that up.

“I did. But I had no choice.”

“I don’t understand.”

“After getting my bookkeeping certificate I was working 6 days a week at the store. Mom insisted that I work as Katie. There was nothing else going on in my life so it didn’t seem to matter. At first I would change my clothes when I got home, but after awhile there seemed no point to it. Mom got me a manicure and pedicure and with my nails like this, I looked ridiculous dressed as a guy. Then she had the salon shape my brows and give me this hairdo. I had no will to resist her. The truth is, I haven’t worn male clothes in over 2 years. My mother seem happy and I have come to the realization that what she wanted all along was for me to be her daughter. And that is what I am to her now.”

I was stunned. How could a mother make her child feel so unhappy?  I wanted to fix it, but I didn’t know if I could. I was about to try.

“Katie, I made a big mistake 6 years ago. The biggest mistake I ever made, and probably will ever make. I loved you. But I could not accept in my mind that you and Jeremy were one and the same. I loved Jeremy too and didn’t realize that. I have to apologize for hurting you. I will never forgive myself for that. I also need to tell you with all my heart I am still, to this day, very much in love with you. I don’t think I ever stopped loving you. If you will have me, I want to be your wife.”

I sat back and with my hand shaking, picked up my glass and took a sip. I could not look at her face. She sat there for what seemed like forever, but was probably no more than a few seconds.

Katie:

Her words stunned me. That was probably the last thing I expected to hear from her. The truth was I hadn’t really thought about Abby very much in several years. All I knew was that I was extremely unhappy.  And now I knew why. Tears were rolling down my cheeks. I made no effort to wipe them away.

I looked up at Abby and saw the tears in her eyes. I had never seen her cry before. I wanted to pinch myself to be sure I wasn’t dreaming.

“I love you too, Abby. I never stopped loving you. Of course I will have you and I shall be your wife.”

She walked around the table, tears still flowing. She kneeled next to me, wrapped her arms around me and we hugged.