Kevin

Editor's note: this story contains scenes of incest or incest content.

*****

Jim

He was in my Psych classes, as he had been last year and maybe the year before. Hard to remember; there were about 300 of us at any given time. He seemed like an odd guy lost in the crowd. He appeared effeminate, girlie; he dressed sort of like k.d. lang with shoes; his hair was all wrong. He was always alone. From my few brief glimpses of him (I tended to look around in class when bored) he seemed the kind of guy who must have been badly bullied in high school. I had little doubt he was having a difficult time here, too. From a distance I felt a little sorry for him.

Up close I was more intrigue. I was at a coffee shop nursing a mug when he sat down at a table next to me. "You're from my Psych 408 class, right?" I kicked at a chair at my table. "Here, join me."

He looked at me, somewhat startled. "Are you sure?"

Sure? I laughed, "Ya, I'm sure. Have a seat."

As he put his mug on the table and his backpack on the floor beside the chair opposite, he introduced himself as Kevin. I told him I was Jim. We talked for about an hour, generally about our courses and a brief outline of our plans after we graduate in a few months. I liked him. I had no doubt the guy was gay but I had nothing against gays, in fact I'd always gone out of my way to be friendly to anyone who could be bullied — I loathe bullying. It is the worst form of cowardice.

I met him again at the coffee shop two days later — he had mentioned he went there after Psych class so I just showed up. We easily picked up our conversation from where we left off last time. We were comfortable with each other and in a few subsequent meetings we were growing into friends. He was easy to be around and he interested me. There was something about him that was slightly other-worldly, to me at least. I had never talked with anyone quite like him before. He seemed like the embodiment of two polar opposites, at once friendly and remote; frivolous and serious; smart and naive ... and even masculine and feminine. But there was something about him that I found particularly appealing. I think it was his innocent enthusiasm.

It was after our seventh or eight session together that in response to my complaint that I hadn't had a non-restaurant meal all term ... I wasn't fishing, he invited me to his place for dinner. I didn't hesitate. He gave me his address, which was downtown not far from the campus, and I was knocking on his door that night at 6 holding a case of beer.

Which I damn near dropped.

When he opened the door he looked terrified ... as anyone might. He was dressed in a white blouse and a pleated plaid skirt and he just stood there, frozen. I felt a weird jolt run through my chest but I recovered fast enough and walked inside trying hard to pull myself together. I put the beer on the kitchen counter, quickly tore one from the carton then turned to face him.

He was standing tense and ashen with his back to the closed door. "This is who I am, Jim. I couldn't go on pretending otherwise."

I looked at him cooly and forced myself to casually sip from my beer. "And who is 'this'?"

"Karen, the person I've always been; Kevin was just a guy I was taught to be." He smiled wanly. "It never took."

"So you're a girl?" It was a shock, sure, but not really all that much of a shock: I knew the guy was different.

"Ya," he smiled sheepishly. "Sort of ... sort of a girl in training."

I turned back to the case. "Do you want a beer?"

"No thanks. I don't drink."

I walked over to a comfortable-looking chair — the place was really nicely furnished for a student. I sat down. "So, I'm supposed to think of you as a woman?"

"As a man when I'm dressed as a man ... but it's not me ... and I didn't want to continue to lie to you ... that's why I asked you back here so you could see who I really am."

She stood rigidly, staring down at me, clearly still terrified.

"So Karen in a skirt, Kevin in jeans? Got it."

She waited, I think she expected more of a reaction from me. Finally, she said, "You're going to stay?"

"I knew from the beginning you're a bit different ..." I shrugged, "not this different, but different."

"You thought I was gay?" I noticed she was loosening up a little, she was a little less tense as if the initial horror was passing and now she merely had to cope.

"You aren't?" I just assumed he was.

"Not as Karen, no."

"Ah," I laughed, stupidly, "right."

We talked, or she did, while I drank five of the dozen beers I'd brought and ate a very good meal. At the door on the way out well past midnight I leaned down and kissed her on the cheek. "You're a tough kid, Karen. I wouldn't have had the jam to handle any of this, certainly not this well."

She beamed up at me, she's about 5'7" to my 6'1" — the evening had gone remarkably well for her. "Yes you would because you'd have no other choice."

"See you tomorrow."

For the rest of the term we met regularly at the coffee shop where Kevin talked in his code, a kind of on-going double-entendre where I was expected to interpret Kevin's words as Karen's. It was hard at first, but it got easier.

His plans after graduation were pretty clear. He had spent the past three summers working for a top-line IT company which had offered him a full-time job in June. He had accepted with the proviso that he be allowed to sign on as Karen, not Kevin. Not a problem.

To get ready for his new career and life, he was starting into his transition from Kevin to Karen. Mentally, he was already there. Now he was working on his appearance. His hair was already suspiciously long and getting longer; his voice was already feminine-esque but he was trying to take it up an octave; he had been taking oestrogen shots for the past five years so he was getting breasts which he kept bound under his bulky shirts during the day. He felt he was ready. Every morning he fought off the temptation to say 'screw it' and show up to class in a skirt. But he didn't, not because of any fears for himself but because he thought it would be unfair to his classmates, too in your face. He would wait for the first day after graduation which he thought of as "the bitter end."

During the early stages of our friendship it had never occurred to me but as I thought about him over Christmas I grew to understand how difficult it must be for him to think and talk as Kevin when Karen wanted so badly to come out. So when we met after the Christmas break I asked him a question I had increasingly wondered about. "Why haven't I had a chance to meet and talk with Karen more often?"

He couldn't hide his excitement. "Do you want to?"

"Ya, ask me over some times."

He did, twice that week. Both times we talked long into the night. I was fascinated and astonished by how much he had to endure to sort out his identity; all the uncertainty and trials he had to go through in his on-going metamorphosis from man to woman. But he was anxious to talk about it all, openly and honestly. None of my questions surprised him; he had thought them through hundreds of times before. He knew who she was becoming even if the world didn't.

It was on my third visit to her apartment that I asked her about the one big subject we hadn't yet touched, not directly at least, only as innuendo: sex. This got a weird reaction from her: blushing and stammering and avoidance. So I changed the subject. But I thought a lot about it later.

On my fourth visit I was more insistent. Didn't she have to deal with his/her sexuality? Wasn't that a huge factor in her emerging identity, her future?

She was clearly uncomfortable and again tried hard to avoid my questions but this time I wouldn't let her. Yes, obviously, she had to deal with it, but she had no experience and she didn't want to get involved in 'the life' to find out. She hoped that once she graduated and got settled in her new career, with her new identity, she would meet new people, probably through the internet. For now she would just wait. Anyway, she had no opportunities to take Karen into a bedroom but that was OK. Was she curious? Of course she was curious. Did she masturbate? A deep red blush gave the answer before she nodded. So, sexually, she reacted normally? Yes. Did she feel sexual arousal now?

"Now?" She turned white; looked like she wanted to run.

I had thought long and hard about it then concluded I could do it. I told Kevin at school the next day that I would be over to her place at 6 on Saturday night. "Dress up, OK? Give me your best shot." I turned away before he had a chance to object.

I knew I was playing with fire; I knew he/she could easily get burned. But I really liked the guy and he seemed to desperately need someone to hold his hand through this part of his transition, if only as a sounding board. But I also knew I had to be careful — the few psych courses I'd taken could only help me fuck with his head. What made the difference in my decision was that he had convinced me that our relationship was an enormous help to him; our talks had been the first time he had ever been honest about herself with anyone other than his sister. And I knew my motives were honest, even altruistic. As I've said, I really liked the guy.

I found out on Saturday night something that hadn't yet occurred to me: Karen is kind of cute — in a transvestite-y kind of way; the clothes and all the make-up kind of went too far but there was no mistaking Karen for Kevin.

She was scared stiff when she opened the door. To put her at ease and, really, I couldn't resist it, I gave her a little peck on the lips as I walked in and told her she looked terrific. She did. She must have spent an hour preparing her face which now was unmistakably feminine. She wore a pretty blouse through which I could barely see the outlines of a yellow bra and a red skirt that fit her perfectly. I noticed she has nice legs that appeared hairless.

I turned back to her as I walked by. She hadn't moved. I didn't know why. I thought maybe I hadn't been effusive enough so I slowly looked her up and down again and told her again how wonderful she looked. But that didn't do it, either, she still stood stiff and frightened and I thought, expectant, so I took the few steps between us and took her in my arms. That's what she wanted, I could feel her sag against me the moment we touched, then hold on to me desperately, pressing her face into my shoulder. I squeezed her to me and kissed her hair. "You look fantastic, Karen; you feel fantastic."

Her moan was clear; I could feel her erection press against my leg. "Do you mean it?" she whispered.

I pushed back and looked at her. She was still ashen, a bundle of nerves. I kissed her on the forehead, lingering. "I think you're really pretty." I tried to let her go but she held on tight and pulled me in. This is what she wanted: a warm welcoming body pressed hard against her's. I gave in to her, rubbing her back.

We stood there for a few minutes just holding on, then I whispered, "Are you all right?"

She didn't say anything for a long time then she said, "Do you really think I'm pretty?"

"Ya, you're pretty Karen, you're really pretty. Thanks for dressing up."

I could feel that she didn't want me to let go so I didn't but I did move her back a few paces so I could press her against the door. I could feel her breathing hard against my neck. I had thought about this, as in what would I do if ...? I had no idea. But it came natural to me now, I didn't have to force it. "Do you want me to touch you?"

I knew she did. Right from the start, or almost, I knew that in getting to know each other we were both exploring our emotions. I thought at first I was dealing with a shy gay guy. Then I met Karen but, strangely, nothing much changed between us because I was still dealing with the same person whom I liked and respected and I thought needed me. I don't know why, but I was strangely willing.

"Could you do that?" Her voice was a whisper into my shirt.

"Not with Kevin, no, but with Karen? Ya, sure I could." I waited a moment for my words to sink in then I asked, "How do you feel? Do you want to be touched?"

She answered immediately. "Yes."

There was a desperation to the single word that made me hesitate. I pulled back to study her. Her face was a riddle of doubt — I wasn't sure if she was doubting herself or me so I leaned in and kissed her on the cheek. "Do you want my hands on you?"

She hung her head as if feeling shame. When she said 'yes' again it was almost inaudible.

I put my hand on her chin and made her look up. "You have to look at me, Karen, you have to convince me that's what you want, that it would be the right thing for me to do."

She gently took the fingers of my left hand and brought then down between us and pressed them against the erection beneath her skirt. "I'm afraid I'll repulse you but I don't want you to have any doubt it's what I want."

I turned away and still holding her hand, walked her to the couch. We sat down our hips touching. We were both nervous, probably for different reasons. "I want to do this, OK, because I really like you, I think you're an unbelievably brave woman and in an odd kind of way I think I'm a little in love with you ... for who you are, for your courage. But if this is the wrong thing to do I'll never forgive you. Got it? Are you sure you want to do this?"

She didn't hesitate. She took my hand and got to her feet and walked me down the short hall into her bedroom.

If there was any doubt he was a she it vanished when I entered that room. Far more than her clothes, her room spoke to who she was. Pinks, frills, stuffed animals, I only got a quick impression before I landed beside her on the bed and she snuggled into me.

We were nearing the point of no return. Now I just let it happen.

And so did she. When I brought my hand up to cover her breast she let out a loud moan, pressed her crotch firmly against my knee and started to ride me furiously, her hands pulling at my hair. This must have been building up in her for years. She wasn't going to last so I pulled away and pushed her from me but before she could take this as rejection I started undoing her blouse. Quickly, she helped then she pushed while I pulled at her skirt and she rose up her bum as I pulled it off and followed it with her panty hose. I now sat back and looked at her.

I could feel her staring up at me. I had tried to think it through, if it ever got to this. What was her greatest vulnerability? What was her greatest fear? It had to be her prick, the extra appendage, the physical baggage. I leaned down and pressed my face against her yellow panties, a little wet with precum, and I bit gently into her penis which was tiny, not even three inches long, but it worked, obviously. It was as stiff as my own.

It was a surreal moment: me with my mouth on her little boner, stiff behind the nylon. I wasn't exactly sure what I was feeling, but there was some love for her, I had no doubt of that. What was she feeling? She told me in a moment when her hands went into my hair, deep, pulling, pushing. I settled down with my head on her belly looking at the little guy throbbing in his panties as I caressed the inside of her legs.

Oddly, it didn't feel weird at all, I thought it would but it didn't. It felt kind of beautiful in its own way. Her penis was straining at the nylon, the dark spot growing wider. I could feel her twitching, her impatience. When I rose up and pulled at her panties she pushed at them and when they were gone and I lay back with my head on her belly looking at her tiny hooded member, red and ready.

I didn't ask I just did it. I slid down and eased her little prick between my lips then I pulled at her bum encouraging her to go in deep and I sucked hard for the few moments until she started to squirm, to cry out, to pull hard at my hair, to thrust insistently until, with a long mournful moan, she emptied herself into my mouth.

The moment she finished she struggled to get up, stuttering apologizes but I rolled her onto her side and took her again, she was still stiff. She whimpered this time, lay perfectly still for a minute then began to gently thrust at me. It took longer this time and the cumming wasn't anywhere near as noisy or as much.

I didn't know if she wanted to do it or not, but as she recovered I sat up and took off all my clothes making a point to show her my erection. But before she could react I asked her if I could see her. She didn't hesitate, there was not a trace of fear on her face when she nodded and she sat up. I undid her bra strap. They were cute, not very well developed but definitely there. I bent down and kissed and licked both of her stiff nipples then kissed her lightly on the lips and asked, "Do you want to suck me?"

She moved quickly, making sure I was comfortable then she took her time, holding me, licking me, biting me and sucking me as she must have practised with someone in her dreams for years.

I stopped her before I came. A flicker of annoyance crinkled her face; she was as close as I was. "Do you want to do it?" I asked. She looked at me blankly, I could see she was confused, so I added, "the way you're going to be doing it?"

"Oh, God," she said when she caught my meaning and quickly sat up.

I looked at her night stand. "Do you have any jelly or anything?'

She was off the bed in a flash and back in seconds with a tube of something. I watched her slather the stuff on her little penis then I got up on my hands and knees. She wasted no time. I felt the cool grease against my anus then her fingers rubbing it around and then her thighs were up against me and her penis was at my opening. She was very gentle. She eased herself into me very carefully but when she broke through she lost it. She grabbed onto my waist and thrust hard about a half dozen times crying wildly before I felt her hot splash in me and felt her sag onto my back fully spent.

She lay on my back for a few minutes, holding on to me, then she rolled off and lay beside me. "Oh, God," she said, smiling at me, a pretty smile, a sweet smile then she moved down and took me in her mouth again.

Her passion felt honest, sincere and loving.

Karen was in the shower. I was in the living room sipping from a can of beer when the knock tapped on the door. I answered it. A tall, thin, elegant woman wore a wonderfully beaming smile that faded to a look of utter bewilderment.

"Who are you?" as if seeing a ghost.

"A friend," I responded, and stepped back to allow her to enter. I knew who she was. I had seen her graduation portrait in Karen's bedroom. Her sister Stephanie is a stunner.

She was wary when she walked in, looking around. "Where's ..."

Just then Karen strolled down the hall wrapped in a thick white towel, her hair dripping water on her bare shoulders. "Hi, Steph. This is Jim, the friend from school I've told you so much about."

Kevin

The last 24 hours have been the most intense of my life, intense and revealing and joyful and even liberating. We all probably look ahead at some time and wonder where it's going and how we can influence the direction, with friends, education, with a whole lot of things. But I hadn't because, while I was coming to terms with who I am and, I guess, what I am, that wasn't giving me a lot of confidence to start shaping who I want to become. I had expected to start that on the day of graduation but, no, I started that last night. I jumped into the deep end ... no I was pushed, I was gloriously pushed by the nicest guy in the entire world.

I met the nicest guy in the entire world after classes at the coffee shop. I was already seated with two mugs of coffees when he came in.

"Jesus," he smiled, whispering, "I almost bent down and kissed you."