This story includes cross dressing, feminization and sex between a male and female, including pegging.

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I had been dating Sherrie for a few months. It was summer vacation, so we had time to spend together. We had made out and she let me touch her but only over her clothes. I was 18, as she was and I was a virgin, almost desperate to lose my virginity — too desperate perhaps, as it turned out. I tried gently pushing Sherrie to go further and even to go all the way. She was sweet, but firm and wouldn’t let things go further, until that day.

“Tommy, I’m not sure I’m ready for what you want.”

“Sherrie, honey, I love you, and I’ll do anything if you let me make love to you, and show you how much I love you.”

“I don’t think you really mean that, Tommy.”

“But I really do, baby.”

“What if I tell you that I’ll let you make love to me and even spend the night, provided you spend the day with me exactly the way I want?”

It was about 9 in the morning on a Saturday, and Sherrie’s parents were out of town and wouldn’t be back until Monday. There was nothing to prevent us from doing whatever we wanted. I was so horny I could barely think. As it turned out, I should have thought more about it all and what Sherrie had in mind. I found out soon enough.

“Whatever you want, we’ll do it.”

“And whatever I want, you’ll do it?”

“Absolutely.”

“You swear? No changing your mind?”

“Baby, I’ll do anything for a chance to make love to you.”

“If you do, then you’ll get the big payoff tonight.”

“You’re worth it.”

“Then let’s get started.”

Sherrie took my hand and led me into the bathroom. I was puzzled by that, but was hardly going to question anything at that point. When we got in the bathroom, she shut the door, then turned and kissed me. I began to kiss her back and reached for her body, to touch and stroke her. She stopped kissing me, pulled away and slapped my hand.

“Not yet. The fun comes tonight, provided you trust me and do everything exactly as I say.”

“Sure thing, baby.”

“Take off your shirt.”

I pulled my shirt off. I knew she said the payoff was tonight, but I was hoping that if I was removing clothes that something more might happen before then. Sherrie sat me down on the toilet, then pulled out a razor and shaving cream. I was kind of a late bloomer and didn’t have a lot of facial hair. I kept a few wisps of what might eventually become a beard.

“I am shaving you — to my satisfaction. Sit tight.”

Sherrie got my face wet then put shaving cream on and shaved every last facial hair off me. I really didn’t care that much. After shaving me, she got a wash cloth and wiped the rest of the shaving cream off me. She had me lift my arms, which puzzled me somewhat, then she wet my underarms and put shaving cream there as well.

“Are you shaving my…?”

“Exactly.”

That seemed strange, but under the circumstances, I wasn’t going to argue with her. She proceeded to shave my underarms, then also shaved the pathetic amount of chest and back hair, which honestly was pretty sparse. She followed that by shaving the hair on my arms. She finished that, cleaned it all up, and had me stand.

“Drop your pants.”

“Are you -? Are we -?”

“Nothing intimate until tonight. I’m just getting you cleaned up.”

I took off my pants, along with my socks and shoes, and she sat me back down and shaved my legs. I was starting to feel a little antsy about it all, but I just tried thinking about tonight and the thought of being able to make love to her and touch her body all over, and to fuck her until she screamed with pleasure. I have a vivid imagination and I know my cock was hard in my jockey shorts.

She finished with that, then handed me some floral body wash and shampoo, and told me to shower and wash my hair. I kicked off my jockey shorts and my cock was about as hard as I’ve ever seen it. She shooed me into the shower and I washed as I was told. It felt kind of strange with no body hair, but it seemed like a pretty small price to pay.

I finished my shower and dried off with a towel. I wrapped the towel around my waist to hide the erection that I still had. Sherrie had taken my clothes out of the bathroom. I stood there for a minute, until she came back into the room. She sat me back down, then got a brush and blow drier and began to dry and style my hair. Along the way, she got scissors and trimmed some here and there.

My hair was not long, but neither was it especially short. Sherrie worked on it for a while, until she was satisfied, then began putting something on my face. At that point, I was kind of zoned out. I didn’t know what she was doing and didn’t really care. This was all just something to make her happy and let me get into her panties.

She had me close my eyes as she put something around them. When she had me open my mouth and put something on my lips, I finally sort of came to and realized that she was putting makeup and now lipstick on me. I xslot didn’t think I liked that, but I’d gone that far and was hoping this would all be over soon. She had me stand and look in the mirror.

With my towel wrapped around my waist, I looked very much like a flat-chested girl. My hair was now in a short feminine cut, and if I’d seen a girl who looked like I did, I’d have lusted after her. Now I was her, though that wasn’t what I had in any way intended. She led me out of the bathroom into her room and handed me a pair of panties.

“Okay, Tommi, put these on, and tuck your dick back between your legs.”

I wanted to get into her panties, but not by wearing them myself. I kind of stood there shocked for a moment. Sherrie looked rather impatient and gestured for me to do what she’d asked. When I hesitated, she spoke.

“You said you’d do whatever I asked in exchange for me letting you fuck me tonight.”

“I didn’t realize you were going to — “

“You said you’d do anything I asked.”

“Do I have to do this?”

“No, but then I don’t have to let you fuck me either.”

I could feel that I was trembling, as I bit my lip, then dropped the towel and stepped into the panties. I pulled them up and tucked my prick back between my legs, which wasn’t easy, since it was really hard. I wasn’t sure why having her do this was turning me on. Did I really like it even if I didn’t want to admit it? I got the panties on and got as comfortable as I could.

Sherrie had a pair of breast forms that she put something on the back of. She had me hold them tight to my chest while she got some other clothes. I realized that she was gluing the breast forms to me and got concerned. She had me step into a cute skirt as the glue dried on the breast forms. She then handed me a bra and helped me put it on, hooking it in back, since I wasn’t sure how.

She gave me a cute pink top to put on, which I did. She then took me to a mirror and the two of us looked almost like sisters — doubly so, since we were close to the same size. She sat me down and put bright red polish on my fingernails and toenails, and had me sit quietly while it dried. I was kind of humiliated by all this, but figured that after all, she was the only one who would see me like this.

She got me a pair of flats that were open in back, so they weren’t too uncomfortable, but they showed off my toenail polish pretty clearly. I was kind of hoping that now that she’d dressed me up, she’d let me change back to looking like a boy. I suppose if I’d been thinking clearly, I’d have realized that the fact that she’d glued on the breast forms, meant this wasn’t going to be over quickly. I don’t have a big Adam’s apple, but what I had she covered with a choker.

“Well, girlfriend, you and I are going to have some fun.”

“Girlfriend?”

“For now, you’re my girl, but if you do what I ask, then tonight you get to do boy things.”

“This wasn’t what I thought you had in mind.”

“C’est dommage.”

“What’s that?”

“That’s too bad. I think it’s time for us to go to the mall.”

“Okay, but I need to change.”

Tommi, baby, you’re already changed. You just need a purse.”

“You want me to go to the mall like this?”

“That was the idea, yeah.”

“I feel… weird.”

“But you look cute. Just don’t let some guy steal you away from me.”

“Oh God, no. I don’t want some guy to — “

Sherrie walked over and gave me a big kiss. I melted into the kiss and kissed her back. As far as I was concerned, we could stand there kissing forever. She had some very different ideas though. She pulled away from me, walked over to her closet and pulled out a purse and handed it to me. I took it from her, though it gave me funny feelings to think of carrying a purse.

She grabbed my wallet, phone, and keys out of my pants and put them into the purse. Sherrie took my arm and began walking me to the front door. I stopped at the door, and I know I had to have looked pained. I certainly felt pained. I was frankly scared as shit to go out in public dressed like a girl. We both knew so many people, it was hardly conceivable that we wouldn’t see someone who knew me.

“Do we really need to do this?”

“Do you really want to fuck me tonight?”

“I do.”

“Then we need to do this.”

We walked to her car and she opened the door for me. I felt strange, but sat down, not paying much attention to how I sat. I looked up and saw a guy across the street, looking at me with the biggest grin on his face. I realized that he had seen up my skirt and probably got a glimpse of my panties. I could feel my face turning red as I quickly put my knees together, and swung them into the car.

“Well, Tommi, nothing like giving the neighbors a little show.”

“It never occurred to me — “

“You need to be more lady-like or you’ll attract a lot of unwanted attention. Unless, of course you want the attention.”

“No, I don’t. I swear.”

Sherrie drove us to the mall, teasing me along the way. I tried xslot Giriş to take it all in good humor, mostly thinking about the payoff that she’d promised in exchange for this humiliation. She parked at the mall and I almost locked my knees together as I swung my legs out of the car. It felt awkward as hell, but I really didn’t want anyone else seeing my panties.

“Well, girl, you’re doing a little better, though you had your knees spread wide in the car.”

“I did?”

“Do that sitting down in public and you’ll be giving the boys quite a show.”

“Shit. This is harder than I realized.”

“You’ll get the hang of being a girl.”

“I don’t want to get the hang of being a girl.”

“You will if you want my pussy.”

“You’re not going to do this again, are you?”

“We’ll see.”

“Oh shit.”

“Let’s just enjoy the mall, girlfriend.”

“Do you really have to call me that?”

“Do you really want people to know you’re a boy in drag?”

“Hell, no.”

“Then you’re my girlfriend.”

Sherrie took my arm and we went onto the mall. It was near lunch time, so we headed to the food court. I’d normally just get a burger and fries, but Sherrie took me to a Chinese place in the food court. I ended up getting broccoli beef with fried rice, while she got Kung Pao chicken. It was good, but I really wanted to dig into a burger.

“A burger isn’t lady-like, and neither is the way you have your knees spread as you’re sitting.”

I snapped my knees shut, which made Sherrie chuckle. I looked around the food court and saw a couple of guys looking over my way and grinning. This was going to take some getting used to — not that I really wanted to get used to it. I tried to make sure to keep my knees tight together as I ate, which was surprisingly hard. As we were finishing, a guy came over to our table.

“Hey, Sherrie, how have you been?”

“Pretty good Rob, and you?”

“Not bad. So who’s your pretty lady friend here?”

“This is my friend Tommi. Tommi, this is Kyle.”

“I’m pleased to meet you, Tommi. And I’d certainly like to spend some time with you, and get to know you better.”

“Nice… to meet you, Rob. I’m really kind of tied up, and I’m seeing someone currently.”

“That’s a real shame, Tommi. Let me know if you’d like to trade up.”

Rob gave me his phone number and chatted with us for a while before he moved on. Sherrie seemed to find that all quite entertaining.

“Rob seemed quite taken with you.”

“Doesn’t matter, I like girls, not boys.”

“Rob is very much a man, not a boy.”

“Man — boy — doesn’t matter.”

“What about a threesome, you, me, and Rob?”

“Fuck, no. That wasn’t the deal.”

“The deal was that you do what I want and you get my pussy. I didn’t say anything about whether anyone else would be involved.”

“If that’s the deal, then take me back and let me change, and you and Rob can do whatever you want.”

“Chill, girl. I was pulling your chain.”

I was almost shaking, mostly in fear that she might actually try something like that, a little in anger that she would suggest that, and perhaps a little bit of a turn-on at the thought. The latter really scared me. Sherrie put her arm around me and kissed me on the cheek. I really wanted her to kiss me on the lips, but I guess she didn’t want to be seen smooching with what appeared to be a girl.

She took my arm and we left the food court, and I began to settle down, at least until I realized that I needed to pee. I knew there was no way I could go in the men’s restroom the way I was dressed, and this mall didn’t have any unisex restrooms. I was scared to go in the women’s restroom, even though the idea gave me a bit of a thrill. If someone realized I was a boy, I’d be in real trouble.

“I need to use the restroom.”

“You should do that then.”

“But what if someone finds out?”

“Were you planning on taking it out and waving it about in the restroom?”

“No, but — “

“Girls go to the restroom together all the time. We go in together, you go in a stall, pull up your skirt, pull down your panties, sit on the toilet and pee.”

“I’m kind of turned on by the idea, but — “

“You don’t touch anyone but yourself, and try not to stare, then wash your hands when you’re done.”

She walked me to the nearest restrooms, then held the door as I went in, following me in. There were three women in the restroom. One was in a stall, and the other two were at the sinks, chatting and touching up their makeup. Sherrie discreetly steered me into a stall, away from the other occupied stall. I latched the stall door, trembling as I did, then almost pulled out my dick to stand and pee, before I remembered her directions.

My cock was semi-erect as I finished, but I tucked it back between my legs as best I could, and readjusted my clothes — well the clothes that Sherrie made me wear — certainly not my clothes, or even my choice of clothes. Sherrie was touching up her makeup as I came xslot Güncel Giriş out. She made me wash my hands and we left. No one seemed the wiser.

“Most girls, after they pee, take some toilet tissue and wipe their pussy.”

“Shit. Did anyone -?”

“I don’t think anyone but me noticed that you didn’t.”

“I’m glad.”

“Just keep that in mind for next time.”

“Next time? How long am I going to have to do this?”

“That depends on how bad you want my pussy.”

“You’ll let me make love to you and spend the night?”

“That’s what I promised — provided you’re a good girl.”

“I’m not thrilled about being any kind of girl.”

“That’s part of the price, Tommi, baby.”

“Part of the price?”

Sherrie smiled, leaned forward and kissed me on the lips. I kissed her back very eagerly, but she pulled away all too soon for my taste. She smiled as she wagged her finger at me.

“No lesbian make-out sessions in the middle of the mall.”

“But I’m not really — “

Sherrie pouted a bit as she looked at me. “I thought you were my girlfriend.”

I bit my lip and looked around. A couple of people seemed to have noticed us, though the bulk of the people seemed to have ignored us altogether. We stood there for a few seconds, before Sherrie took my arm and walked us to one clothing store. It was a small place with exclusively women’s clothes, oriented around stylish young women.

She took me from rack to rack, looking at all manner of things, including tops, skirts, dresses, and even bathing suits. At one point, she pulled out a sexy dress that was short and appeared form fitting. It was from the clearance rack and apparently marked down. She held it up against me, though I didn’t think anything of it. Then she took the dress and me and headed toward the dressing rooms.

“You would look so cute in this, Tommi. Please try it on for me.”

“I don’t think — “

“Don’t think. Just try it on and model it for me.”

She handed me the dress and gently pushed me toward the dressing rooms. I was scared as shit. I was going to have to go in a dressing room, take off my skirt and top, then put on this sexy dress. After that, I had to come out so Sherrie could see me in it. I was shaking as I went in and closed the curtain. I was a bundle of nerves as I took off my top and skirt, then struggled a bit to get into the dress.

I managed to get into it and straighten it out so it didn’t look too bad, then realized I could not zip it up all the way. I stuck my head out and told Sherrie I could not zip it up. She waved me out, then had me turn around and zipped it up. She adjusted it on me, then stepped back to look at me. She smiled, then gave a sexy little wiggle as she looked at me.

“You look so cute in that. Here, look in the mirror.”

She turned me toward the mirror and I saw myself. I’d never have recognized myself as the boy that I thought I was. I looked like one sexy, hot-to-trot young woman. I swear to God, I was lusting after myself as I looked in the mirror. Sherrie came up behind me and ran her hand down over my ass. I could feel her breath on the back of my neck.

“You look so hot. You need that dress.”

“But, I don’t — “

“I’ll buy it for you, baby. We’re going out tonight, and you’re wearing that dress.”

“Oh, fuck.”

“That comes after, provided you’re a good girl.”

“How long -?”

“As long as I say. And I’m enjoying having a sexy girlfriend to spend time with.”

She unzipped the dress, since I could not manage that. As she did, her hand strayed down over my ass again. She caressed my ass for a few seconds, before gently swatting my ass and telling me to get changed. I was shaking again as I went in the dressing room, took off the dress and put my skirt and top back on again.

As I finished dressing, I turned around and realized I hadn’t gotten the curtain closed all the way. There was a guy standing there, looking at me through the gap in the curtain, with a huge grin on his face. I could feel my face heating up as I know I turned very red. About that time, I heard some angry mumbled words and saw his face drop, as a woman took his arm dragging him away, giving him hell as they went.

I waited until they were out of sight before I came out. Sherrie was looking at some other clothing items, but took me up to the cashier and paid for the dress she’d just had me wear. They carefully folded and bagged the dress for us and we left that store. I was really hoping that was the end of trying on clothes, at least of me trying on clothes.

We mostly did window shopping for a while, though Sherrie tried on some clothes, and had me try on some more clothes. I had to hit the restroom once more before we were done. We ran into some more people that Sherrie knew, some of whom knew me, but they never recognized me the way I looked. I was really nervous the first time we met someone I knew however.

Carl and I had been in several classes together, and when I saw him, my blood ran cold. I wanted to head in the other direction as fast as I could, but Sherrie had a firm hold on my arm. I just knew that Carl would recognize me and realize I was a guy in drag. Instead, he walked up to Sherrie and I looked me over and smiled, then asked Sherrie who her cute friend was.