tagTranssexuals & CrossdressersMy Summer with Kelly

My Summer with Kelly


This isn't your ordinary cross-dressing story. In this story, a girl passes herself off as a boy to gain entry into a school, then finds out that being a boy is harder than she thought.

Like all my stories, this one doesn't get to the sex right away. It starts off pretty slow and builds as it goes along.

As always, your feedback (good and bad) is welcome.

* * * * * *

This story is a compilation of events my own observations and from what Kelly and her friends told me happened (in the events where I wasn't present). If I'd known how this summer was going to turn out, I may have never agreed to let Kelly stay with me.

Kelly's physique and appearance made it easy to pass herself off as a boy, which she needed to do to be accepted into a college workshop that had been closed to girls to allow a few slots to be reserved for any boys to sign up. Kelly hated the sexist rule, but being a private school, there was little she could do about it other than try to get around the rules somehow. Out of desperation, she altered her appearance and filled out the application, pretending to be male.

Even though I had never met her before this summer, I had agreed to allow Kelly to stay at my place so she could attend the workshop. Her parents were family friends and I had a difficult time coming up with a reasonable excuse why she shouldn't stay. When Kelly showed up at my house, she was every bit the 18-year old girl I had expected. With a slender body and a natural charisma, I had to remind myself she was half my age.

I was shocked the next afternoon when she showed up at the house decked out like a boy. Instead of the tube top and mini-skirt, she was in a pair of baggy shorts and a T-shirt. If I hadn't already seen her dressed as a girl, I would have never guessed she was a girl. She'd gotten her blonde hair cut short and had dyed it to a darker color. With no make-up and no jewelry (aside from a wristwatch), she was very believable as a boy. She'd managed to flatten her already-smallish breasts down on her chest with a large Ace bandage and had a sock in her shorts to complete the look.

We had a big discussion about the dangers of her trying to pass herself off as a boy, but she wasn't changing her mind no matter what I said. Finally, I agreed to help her with her task, helping her change her mannerisms to be more believable as a boy.

Kelly went to the workshop where she immediately made friends with two of the guys in her classes. I guess she thought it was a good idea to hang out with the guys so she would appear more masculine. Whatever the reason, that decision was what would ultimately lead to her undoing.

The two guys she made friends with were Danny and Steve. Danny was a pretty plain kid, horny like all 18-year olds, but with limited ability to get himself laid. Steve, on the other hand, had all the charm Danny only wished he had. At the age of 19, he'd already slept with at least two of the girls in the workshop and he'd only been in town for two weeks.

Steve was one of these big guys with a natural charm that attracted women, but as Kelly would find out, when the girls weren't around, he was all guy, complete with bad manners and a long list of ways to objectify women, but even with this intimate knowledge, she still wasn't put off by him.

Kelly was happy with herself for doing such a good job of passing herself off for a boy. On about the fourth day of the workshop, Kelly played some basketball with Danny and Steve after their last class. Being a natural athlete and very competitive, Kelly accepted.

After the game, Kelly and the guys were hot and sweaty.

"Let's get a shower," Steve suggested.

Kelly followed the boys into the locker room, "I didn't bring anything to change into, so I'll just go on home," Kelly said, giving her an excuse not to strip in front of the boys. Besides, at eighteen years old, she'd only been with one boy before and she'd never seen him stand in front of her completely naked. The thought of seeing both her friends naked made her uncomfortable.

"I thought you were going to give me a ride home?" Danny asked.

"Damn, sorry," Kelly explained. "I'll just wait outside for you guys then."

"Bullshit, just sit on the bench and wait for us," Steve argued.

"I guess I could get caught up on tonight's homework," Kelly said, opening her book bag.

Steve and Danny started to undress in front of her. Kelly looked directly down at her open book, but couldn't help to glance at the two boys from time to time as they stripped out of their clothing.

Kelly felt her heart pounding in her chest. In the few days she'd known the boys, she'd grown fond of both of them, and under other circumstances, she would have dated either of them, especially Steve. Sure, he was crass at times, but he also had a charm that made her heart beat faster every time he was around her.

Kelly glanced up to see the crotches of both naked boys right in front of her. She tried to act like she wasn't looking, but she couldn't help it. Based on the few dicks she'd seen in her short sex life, Danny appeared to have an average-sized cock, just right for his frame. If Danny's cock was an average size, then Steve's was disproportionately large. It was not only large compared to Danny's but larger proportionately on his body. Looking at it dangling there, she guessed that if she had wrapped both hands around it in its flaccid state, she might not cover it all with both hands. Kelly wondered if this piece of anatomy contributed to Steve's popularity with the women. If it got any bigger than that when it hardened, she didn't think she could take it all, or at least she'd have to take it with a great deal of discomfort.

The boys entered the shower stall, which didn't have any dividers or curtains. Instead, four shower heads jutted out of the plain wall. As the boys faced away from Kelly to turn on the water, she couldn't help but look down at each boy's buns. She enjoyed what she saw.

Then, as the boys turned around to face her again, she made sure she had her face in her book.

"Dude, do you ever get any pussy with that?" Steve asked Danny with a grin.

"There's nothing wrong with my dick," Danny argued. "You're just a freak of nature."

"I'm no freak," Steve gripped the head of his cock in his hand and gave it a few pumps. "I'm a work of art."

"Be careful," Danny warned. "Or all the blood will run from you head to your dick and make you pass out."

"Hey, fag, it's my dick. I can wash it any way I want."

"Kelly," Danny called out, "Will you look at that thing? Isn't it hideous?"

"I'll take your word for it," Kelly responded.

"Afraid you're going to see something you like?" Steve joked.

"In your dreams, faggot." Kelly retorted.

"Sure, you say that, but I bet you'd love to suck it," Steve said, still stroking it.

Kelly thought about that for a second and realized Steve's words were true. She'd never been turned on by vulgar nudity like this, but in this sense, where the boys didn't know she was actually a girl, she felt powerful and in control. She felt the familiar tingling between her thighs as her pussy moistened.

After the shower, Kelly waited for the boys to get dressed. Driving them home, she couldn't get the images out of her head. Seeing Danny and Steve naked as she had, with Steve stroking that big cock of his in such a carefree way clouded her thoughts. Kelly gripped the steering wheel tightly with both hands, afraid that if she loosened her grip at all, she'd reach over and grab that big cock of Steve's and bend herself over to be taken from behind by Danny.

Somehow, she manage to control herself throughout the drive and managed to get them to Steve's place. After she'd dropped them both off, Kelly headed straight for my house. I was in the living room when she got home.

"You look like you have something on your mind," She really looked flustered.

"I had a really strange day," she said in her soft, feminine voice.

"Uh, aren't you supposed to stay in character when you're dressed like that?" I asked. Remaining in character was one of the rules she'd created for herself.

"Damn it!" she exclaimed, sounding like a boy again.

"It's your rule, not mine," I reminded her.

"Fine, fine, I'll change."

I thought she'd head off to her room. Instead, she unbuttoned her shorts and kicked them off, revealing the boy's briefs beneath, complete with the artificial package bulging in the middle. Next, she peeled of the T-shirt to reveal the bandage that was flattening her breasts down onto her chest.

"Is this better?" She asked, hands on hips.

"Not really," I grimaced. "Now, you just look creepy, like a guy with a chest injury or something."

"I really need to talk to you!" She protested, sliding the underwear down and off to reveal a pair of panties underneath that clung to her body. As her boy underwear hit the ground, the rolled up sock fell out and onto the floor.

"I'm not sure if that's better or worse," I said, looking at her dressed in powder blue panties and a bandage covering her small breasts.

"Well, we're practically family," Kelly protested. I had good intentions, but with her standing there with those panties clinging to her petite form wasn't helping me concentrate on her problem.

"Fine, I can see you're upset. Next time, just get undressed in your room before you start ranting, okay? Now, what's the problem?"

"Being a boy is harder than I thought," she complained.

"I tried to warn you. Boys are vulgar and disgusting. You either have to let that stuff pass right on by you or you're never going to last," I explained, thinking I already knew what the problem was.

"It's not that," she began pacing the room. I could tell she was having difficulties putting her thoughts into words. When she stormed out of the room, I thought the conversation was over, but she returned, carrying a small tank top in her hands. She slipped the tank top on, then unraveled the bandage from underneath it. "I was in the locker room with my friends today, and they were taking a shower."

Kelly slipped both hands inside her shirt to massage her breasts, which, until now, had been trapped beneath the bandage all day. "It feels good to get that off," she confessed.

"Okay," I said. "You were explaining?"

"Oh," she pulled her hands out from her shirt, allowing her hardened nipples to press against the thin material.

"The guys took a shower?" I asked.

"Yeah, Steve and Danny both took a shower and I was, well, I was there in the room while they did it, and I saw EVERYTHING!" Kelly sounded embarrassed.

"And these are the two boys you like, right?" I didn't understand.

"Yeah, that's what makes it so bad," she said, hardly making eye contact with me.

"I'll never understand women," I said, "If it was a guy, then that's the one he would want to see naked. I don't understand why that's so horrible. They still don't know you're a girl, right?"

"No, they don't."

"Then, what's so bad?"

"I just felt," she made a long pause, as if to gather her thoughts. "I just felt like I was losing control. I had to drive them home and all the way to Steve's house, with him sitting next to me, I felt like acting on my feelings, you know? I felt like I should just grab him or tell him how I felt or something."

"I think I know what you mean," I didn't like this conversation at all. I didn't feel comfortable with her standing there in a pair of panties and a tank top, either, but I'd seen most of her body before when I was helping her dress herself up as a boy for the first time. I'll have to explain that one later...

"What would you do in this situation?" She asked.

"Well, the situation is already pretty strange and far beyond any of my life's experiences. I don't know what I'd do. You don't want to act on your feelings. That won't work, especially if you're trying to maintain your place in that workshop, which means keeping your identity as a girl a secret."

"Then what should I do about how I feel?" she sounded even more frustrated.

"Emotionally or physically? I don't really know what you mean."


"Well, if you really were a guy, then I can tell you what I'd do."

"Tell me."

"Okay, don't get upset with me when I tell you this, but if you were a guy, I'd tell you to go masturbate and fantasize about one of the guys, or the other one, or both, or whatever and just really get it out of your system."

Kelly just stared at me, unblinking. "Is that what you do?" She asked.

"What do you mean?" Now, I really felt like a pervert. This girl was half my age and asking me for relationship advice and I was giving her advice about whacking off. "Uh, I think maybe I've said too much. Sorry if I offended you." I stood and headed to the kitchen.

"No, wait," she said. "You didn't offend me. It's just that, well... Can I make a confession?"

"I guess so..." I was hesitant to hear what she might say.

"I've never done that," her voice was almost a whisper. "I wouldn't know where to begin."

"Um, okay, I think that's enough of this conversation. I've said too much already."

"No, wait!" She pleaded. "A few more things and I'll leave you alone."

I just looked at her and waited for her to continue.

"How do you recommend I do it?" she asked.

"You're serious?" I asked. From the look on her face, I could tell she was. "Don't you have a girlfriend you can ask about it? Or I could get you a movie. No, wait, I've seen those kinds of movies and they're no good." As much as I was trying to resist it, I was getting aroused from talking to her about it. "Maybe we should sit down and talk about it." I sat myself down on the couch. Kelly sat on the opposite end. "Okay, um, there are lots of ways you can do it. If you've never done it, I'd recommend just rubbing your clit until you bring yourself to an orgasm."

"Rub it how?" she asked timidly.

"Well, just kind of spread your legs and rub your fingertips around on whatever feels good. I'm sure you won't have any problems finding the perfect spot."

"Here on the couch?" She asked.

"No!" I said quickly, trying not to sound like I was scolding her. Even if she was bold enough to masturbate in front of me, I didn't feel comfortable with the idea. "In your room. You can go in there, close the door, and light a few candles or something. Or if it can wait, do it when I'm not here. I'll go to my room and turn the TV up or something, so you can pretend I'm not even here."

"Wait, let me make sure I know how to do this," she said, pushing a hand into the waistband of her panties.

"Whoa!" I exclaimed, then placed a throw pillow over her crotch. "I don't mean to be prude, but maybe that's something I shouldn't see."

Kelly probed around inside her panties for a minute until she found what she was looking for. "Okay, I think I have it now," she grinned, then got up and walked out of the room.

I left the room, too. I headed for my bedroom, closing the door and locking it behind me. I grabbed a clean towel off the closet shelf and a bottle of skin lotion. Draping the towel across the bed, I filled my hand with lotion, and pulled my shorts and underwear down to my ankles, allowing my cock to spring free.

I was twice Kelly's age, but seeing her in those little panties and tight tank top shirt with her nipples poking through had really gotten me aroused. If that hadn't been enough, she'd sat right there beside me and slipped her hand into her panties to find her little clit.

Thinking of that petite girl masturbating herself for the first time only two rooms away was more stimulating than I would have imagined. If things were just a little different, then I would have jumped all over her. As I stroked my stiff cock, I imagined what it would have been like if there were no consequences. I would have just told her to take those panties off and to spread her little pussy out so I could point out her clit for her. Then I'd have rubbed that little nub until I made her cum. And, if that didn't work, I would have buried my face in that little 18-year-old pussy and munched on it until she came all over my face.

After that, I would have said, "Why don't you return the favor. Put my cock in your mouth and show me what you'd do to this cock if it belonged to one of your two friends from school."

That did it. The image of her kneeling before me and taking my cock into her mouth was enough to put me over the top. My hips jutted forward as my cock convulsed and shot my cum out onto the towel on the bed. I milked the cum out of my cock, happy to have expended the energy that had built up in my groin since Kelly had gotten home.

I cleaned myself up and went to bed. When I got up the next morning, I ran into Kelly in the kitchen. She was dressed in a pair of skimpy shorts and another tank top. This one showed off her flat, little belly.

"How are you this morning?" I asked. "Feeling any better?"

"Much better," she grinned, looking a little embarrassed. "Thanks for your help last night."

Part 2 Everything seemed to be working out okay with Kelly. She didn't ask me for any more advice for the next week and I noticed she was spending more time in her bedroom with the door closed and soft music playing. Sometimes, I heard her listening to Leonard Cohen music, which seemed a little strange to me, but I suppose everyone has their own tastes.

About the middle of the second week, she told me she was invited to a party at one of the kids' houses. It was a costume party. She'd heard her two friends, Danny and Steve were going to be there. Kelly told them she wasn't going to make it. I asked her why she would do that. She told me she had a plan. She was going to go in a costume dressed as a girl so she could be in their presence as a girl, but without them being able to recognize her. I didn't think it was a good idea. The risk for getting caught was too high and it didn't make sense if she couldn't show them who she was. Still, it was her choice and she'd made up her mind. Besides, it wasn't my place to stop her.

The night of the party, Kelly asked me if she could model her costume for me before she went to the party. I said, "Sure, why not?" After all, I thought, how bad could it be? Well, I've gradually learned not to under-estimate Kelly's ability to shock me.

"Are you ready?" Kelly called from her bedroom.

"Yeah. Come on in," I answered.

When Kelly strutted into the room, once again, I didn't recognize her. She'd onece again transformed herself from the initial petite girl I'd met, then she'd altered her appearance to pass herself off as a boy, but now, standing in her costume, she had become nothing less than an attractive vixen.

"Where on earth did you get a costume that?" I asked. Her breasts were covered (barely) with a red latex top. The rounded edges of her smallish breasts peeked out from each side while her nipples strained against the latex material.

"Why? You don't like it?" She asked in return.

"No, it's great. It's just that it fits you perfectly." I explained.

"I tried on at least a dozen costumes before this one. I'm glad they had it in my size."

"Me, too," I said, thinking aloud.

The latex top was matched by the short shorts, capped with a white leather belt. Knee-length latex boots with laces from the toe to the knee covered the bottom half of her legs. The heels must have been at least three inches long. They also made her look taller. Red latex gloves covered her arms up to her elbows.

Finally, her face was covered with a red, latex half-mask that hid her flesh from her nose to her forehead. It was a shame to have to cover her pretty face up with the mask, but without it, the costume was not disguise. Her hair was disguised with a platinum blonde wig that ended at the base of her neck. In back, she wore a short red cape that ended at her waist.

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byKarlMartinK© 1 comments/ 54186 views/ 6 favorites

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