Kevin

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
Erewon25
Erewon25
42 Followers

I laughed and waited for him to sit down then leaned forward, "In another couple of months I'll be mad if you don't."

He chuckled, took a sip of his coffee and looked at me intently. "So? Are you traumatized? I'll never forgive you if you are."

I told him that after he left I had talked all night with my sister, even getting into detail. She had listened patiently, she never once interrupted until I got it all out, then she asked the one question I could never have answered before the experience. "Is that what you want? A heterosexual man?"

I had always assumed it was. "It isn't. No. I'm sure of that."

"No?" Jim was confused. Then he smiled and laughed, "Hey, I did my best."

"But I'm liberated, Jim, honesty. Totally liberated. I know where I fit in. I need to find someone like me." Now, I laughed, Kevin laughed but Karen is just riddled with joy ... she's been giddy ever since she figured it out.

"So, what are you going to do? Troll the streets?"

"There's a club just off campus. I've been aware of it since I got here but I didn't want any part of it. Now I do, or I think I do. I'm going on Friday night ... to check it out."

He thought about this for a moment then said, "Ya, I'd go too. You've got a life to live; better get at it. I'll drive you ... and wait outside."

I hadn't told Jim that Steph had made the same offer. Why should I? It was a great excuse for them to spend some time together. It might work. Steph seemed a little fascinated by him, half believing he was a rogue, half believing he was a saint.

But she was clearly uncomfortable when she got into the backseat of his car on Friday night. He didn't seem too pleased either.

I was primed. A little nervous but not nearly as nervous as I thought I would be. I had been Karen in public many times before, but always anonymously. I never stopped; never spoke to anyone. Now Karen was showing up at a club dressed in a pearl grey skirt and pale blue blouse and sweater. I had no idea what to expect but I was excited and, with a get-away car idling on the street, even a little confident.

It was a darkish room but clean and orderly. There were maybe 30 people milling about, mostly (dressed like) women and all dressed far more flamboyantly than I was. It took seconds before I was sucked into a whirlwind of talk, laughter and hugs. And this before the dancing started.

I was there just ten minutes when she asked me, whispering in my ear, if we could get together later. I knew this might happen, or I think I hoped it would. And so did Jim and Steph who kept warning me in the car: make sure you feel comfortable with the girl before you commit to anything; make sure you don't feel threatened. And you can't go with her; she has to go back to your place.

We got back to my place at about 11:30. The ride was quiet. After I introduced 'Fattie', that was her name and, to an extent, her condition, we were all quiet. And nervous.

I thought they were going to walk us to the door or even come in to my apartment. They didn't. But when we got out, Jim did too and he leaned against the car and said to Fattie, "Karen is not very experienced. You will be good to her." It was a statement, not a question and there was a hint of malice in his words.

But Fattie didn't seem to notice. "Totally," was all she said.

It's three floor up to my apartment, she was on me before we reached the second.

I was lying on the bed, my penis limp and glistening with her saliva. There were strands of my cum in the hair and small blobs of the stuff on my belly. She was sitting cross-legged beside me running her finger up and down my rectum, sliding along on a sheen of grease.

"I don't think about it," she said. "I never have."

"How could you not?" I insisted. "We're different."

"We're all different. I'm me, that's all I know."

She swung her leg over me and pushed herself toward me, holding her slightly stiff penis so it could easily slide into my mouth. It was a little bigger than mine but far more energetic. It was the fourth time I've sucked her. She liked it sitting up with my face in her lap with her hands on the back of my head forcing it deep into my mouth, almost to my throat. But it didn't seem to be the sucking she wanted. I think it was the power. She never came. She thrust for awhile then pulled me away by the hair. She had put it in my bum twice but never sustained it for long, just a few thrusts as if she was proving she could do it.

The whole thing felt like random acts of weird; having me here, having me there. Maybe she was just using me, who knows? Killing time. It lasted an hour before she got tired of it. "I'll call a cab," I said when she clearly seemed bored.

"Thanks."

But I was giddy when the door closed behind her. Not because she was gone, because I knew for sure she is what I want. Not her specifically but a girl like myself, built like me. How could I have known that until I experienced her? And how could I have known that a man's smell and maleness kind of repulsed me until I sucked Jim?

I was sure now. I wanted a girl who was built like me. But she would have to love me, I knew that, too. And I wanted her to have a nice body, one that she liked and took care of.

Jim

We hated to leave, but we had to. Karen could take care of herself. We hoped.

Stephanie's car was in the parking lot around the corner. I drove over to it and parked next to the grey Audi, as directed. Before she got out she turned and asked if I'd like to go back to her place for a coffee or a drink.

When I declined I noticed a slight grimace so I quickly explained that I was going hiking first thing in the morning, then, I don't know why, I asked her if she wanted to come along, I was planning on using up much of the day, about five hours.

It surprised me when she quickly accepted and in a few minutes we had worked out the logistic and I was driving home wondering what I had gotten myself in for.

The three hours in the car with her earlier that night weren't as bad as I thought they would be. We talked about Kevin for much of the time, and then Karen. She knew him all too well: had done her research; had developed her theories; had identified her hopes. No kid in Kevin's fix could hope for a better sister. She was about five years older than him (and therefore me); was a lawyer working crazy hours; was frazzled and she totally loved her brother and even more, her sister.

I remained pretty much an enigma to her. I told her I was going into the advertising business in September, with my father who owned an agency (I had worked there for the past three summer). And I told her that first I was going on a bike tour of Europe. I may have added that I was an only child.

Next day, we were sitting on a rock in a patch of sunlight nibbling trail mix when she look over at me. "You don't much like me, do you?"

I had been walking behind her whenever I could, admiring her spectacular ass so this question was so totally out of context it confused me for a moment. Then I looked at her cooly. "In fact, I love you ... for what you've done for Karen. She told me you're fabulous and she's right. But we're obviously very different people, aren't we?" I didn't wait for her answer. "For instance, my type would pull off this trail and bushwhack up to the top of this hill, not caring if I got lost or how dirty and cut-up I got. I have a feeling your type would not only stay on the trail but time yourself to make sure you completed the trip efficiently. Am I wrong?"

She looked away. Her shoulders seem to sag. She was completely still before her melancholy began. "Karen doesn't need me any more. She hasn't needed me for pretty much the past year. She's been my life. She's what I've been working for. I wanted her to have the operations, the counselling, all the help she could get ... everything she needed. But she didn't need any of it. She did it all herself." Her shoulders trembled a bit. I thought she might be sobbing. "She's ended up fully in control of herself and I've ended up with nothing."

I've never liked whining. "Bullshit! You were there for her every step of the way. She would never be where she is now without your help. She knows it. Whatever you've done for her she couldn't have got by without it. You should be proud of yourself."

She seemed to be almost sloughing in defeat now. She hadn't heard me. "I hated him. He embarrassed me, shamed me. I thought he was a freak. He thought he was a girl? Ya? Well, I thought I was a fucking super model. Get a grip. But he wouldn't. He'd wear my underwear, pin my clothes to fit him, ask me how he looked, how should he walk, talk, how does he apply make-up. I loathed him; totally ignored him; ran from him. I had my own life to lead. Then our parents died. I was 19 he was 14. We were alone in a big house. Overnight he became my problem. I had to deal with him, there was no one else."

She glanced over at me to see if I was listening. I was. She looked away again. "It was horrible. I didn't understand any of it. I just wanted to live my life, go out and party, get wired, get fucked, get away from everything. But I couldn't. I had no choice. I had to deal with him. So I did, I said fuck it! You want to be a girl? Fine. I bought him pretty little panties and bras, tank tops and all the rest and I told him how cute he looked. But I read, too, I studied. It took a year but I started to understand, to come around, to realize this wasn't some emotional trip he was on but a medical condition and when it finally all sunk in I hated myself for the shit I had been, for all I had done to him, for all my feelings. Everything changed. I think it was the guilt. I put my head down and, you're right, I walked a straight path and timed myself to make sure I did it efficiently. I became the provider, the therapist and in a few months, the mother. He became like my child. I was fiercely protective. I lost all perspective and I haven't got it back."

I was trying to take all this in when I realized she had stopped. "So what are you going to do about it?"

She stood up and stuffed the little bag of trail mix into her backpack. "Try bushwhacking."

We did. We left the trail at that spot and headed into nowhere with only a distant hilltop as a beacon. We got there two hours later, dripping with sweat, scratched and at a point near exhaustion.

We were lying in a small meadow with our shoes and socks off. I was fighting off sleep. I said it because I felt it. I looked over at her. She was on her back three feet away with a long slender arm covering her eyes. "If we had sex, that would make you a cougar. Have you ever wanted to be a cougar?"

She hadn't moved when I spoke but when I finished she removed her arm and glanced over at me. "I'm a bit of a mess right now."

I looked at her cooly, challengingly. "Think of it as bushwhacking."

She was still for about three seconds then she rolled over and crawled towards me. She put her lips on mine and kissed softly. "I'm soaking and it isn't just from the sweat."

"I walked the last mile up here with a hard-on."

She quickly sat up and grabbed at my shirt; I worked on my pants then pushed her down and as she wrestled out of her shirt I pulled off her shorts. She sat up to deal with her sports bra. It was fused to her skin; she seemed to be almost pealing it off when her breasts popped free and I pushed her down again and pulled off her underwear.

God, she was ready. As ready as I was. She was lying with her legs bent and opened, her arms reaching up to me. I was on her in an instant, my eager erection wanting to bury itself deep inside her. I was touching her wet opening when we heard the shout. It stopped me. Cold. But she continued pulling me in. I pushed away, resisting, listening as she persisted, bucking up against me, trying for penetration. "There are people out there," I protested, looking around.

"Who gives a fuck." She was pulling at my arms now with all her strength.

When more voices floated over the hill I quickly rolled away and reached for my clothes. She sat up looking at me, clearly pissed off. "Come on." I threw some of her clothes at her; got up clutching mine and hurried the few paces to the bushes. She didn't move. She sat there looking to where the voices had come and considered her options. Then she slowly put her clothes on. She was fully dressed except for her shoes when the small group summited the hill.

I felt like an absolute dweeb there in the bushes clutching my clothes. Her look of utter distain didn't help, nor did the eventual realization that my inspired bushwhacking nearly paralleled the well-trod tail to the summit.

As we descended I had clearly lost the high ground. She led, I followed, the silence was lethal. About a quarter of the way down she stopped, turned back to me and said, with ill-disguised scorn, "Look, Chingascook, is there any way you can find a clearing along here. I don't know about you but I finish what I start."

She didn't cover up when it was over. She lounged against a bolder. I could see my semen on her rich black bush. It made a fabulous snapshot, a moment in time that I hoped I'd always retain: The Beauty and The Rock. God, she is utterly fabulous.

She is tall and sinewy, a graceful lean torso softened by wonderfully full breasts, slim, rounded hips, long, elegant arms, legs and neck, and a strikingly refined, chiseled beauty in a thoroughly regal face. Stunning. But she is human now where only yesterday I found her a remote cut-out. And she is disarmingly lewd. She didn't care what she said now; she didn't care that I was looking at her gaping pussy.

Her classically beautiful arm languidly dangled from a knee, the long stretch of inner white thigh slightly blemished by the small reddish bruise where I had sucked. "I hate being a lawyer, I've always hated it." This came out of nowhere. "I hate working all the time. I hate not having fun. I hate not sharing. I hate doing nothing creative. I hate my loneliness." She had been looking away, now she looked at me. "I hate walking trails and timing myself to make sure I get it done on time. I hate it all. And I hate that I had to ask you to come back to my place. And I hated it when you said no."

I took the jab without reacting.

"I made up my mind about a month ago — it was probably earlier, when you took over as the centre of Karen's influence, I made up my mind to pack it in, it was only a question of when. It'll be on Monday. It'll take a couple of months to tidy things up but then I'm never going to wear a blue fucking suit again, no more black shoes, no more fucking briefcases. And I'm never going to work past 5, never on a weekend and I'm going to get regularly and royally fucked and if you're not going to do it, I'll find someone who will."

She was deadly serious. There wasn't a hint of doubt in her eyes.

"Karen's prick has done a lot better job at fucking up my life than it has her's. That's stopping now. I love her, love her to bits, will do anything I can for her, but I know what Job One should be now and if I don't get at it I'll stay the same fucking dimwit I've become and I just can't stand the thought."

"You got fabulous tits," I said to add a little levity.

She looked at me cooly. "Thanks."

"And a great ass."

"So I've been told."

"But it's your clavicle that's keeping my dink hard. I'd love to see it wearing pearls."

"I want to go on that bike trip with you."

"Oh, don't be such a priss."

I shut up and kept driving. I was learning not to argue with her.

She had just taken off her shirt to peel off her bra. Her shirt was back on when she started pushing down her shorts. "You know for a cool guy you can be really really prissy."

Her shorts were on the floor; she was stripping off her panties.

I tried not to look over. "Who said I was cool?"

She laughed. "Oh, you're cool, alright." She dropped her panties and put her shorts back on.

I didn't think of myself as cool. Detached, maybe, but not cool, at least not in the way I thought she was meaning it.

Now free from the sweaty underwear she had been complaining about she settled back and re-clipped her seat belt. I could tell she was thinking. "How many guys would have done what you did for her?"

"What?" I wasn't sure (or want to admit to) what she was referring to.

"Sleeping with her; letting her experiment with you. Now that's cool. That's unbelievably cool."

"Who told you that?" I asked stupidly.

"She did, but she didn't have to. When she came down the hall with that towel wrapped around her, glowing, even a fool could see that she had just gotten well,and truly laid ... I know the look, be,I eve me." She laughed at the memory. "God, she was just glowing ... and I was shocked, speechless! You were a guy, a normal-looking, well, a good looking guy. What were you doing fucking my sister? You didn't look like a smarmy perv but you must have been."

"Thanks."

She was quiet for a moment and I soon understood why. She must have been debating whether or not to open up. She did.

"I'm pretty cool, too." She told me.

She knew Kevin was different early on, how early she couldn't remember. Maybe 8, something like that. He'd dress up in his mother's clothes, sometimes he painted his nails; he was effeminate — different. And he was always studying his mother, then her, too. But she ignored him, avoided him.

Everything changed for her when their father died ... with his new girlfriend, in a small plane crash in the Mohave desert. Four days after the funeral their mother slit her wrists in her bath tub. The note said she hated her life and couldn't stand to live another minute of it.

Stephanie was 18, Kevin 13. They were barely speaking to each other. Now they had to. She skipped over the next few years just saying they were 'rough.' But they grew together. Kevin was an innocent: good natured, hard working, uncomplaining and open. He was also bullied unmercifully at school and confused and frustrated everywhere else.

They had their first real conversation near the end of their first year together. He was a girl, he knew it, he just didn't look like a girl, wasn't built like a girl. How could this be? Stephanie looked into it. Transgender. It was possible. He certainly was different. She continued to research it; they continued to talk.

He was looking at her all the time, studying her. He wasn't subtle about it, nor lewd, just curious, wondering if that was what he would have looked like if he had just one different chromosome.

Through their conversations and her research, she slowly started to understand and, because he was such a sweet, eager to please guy, to empathize.

It started when he was about 16. He had often showed up in her bedroom just at the time she was getting ready for bed. She'd shoo him away at first but then she'd let him see a little of her while she undressed to get into her pyjamas. He was curious, she knew that and soon realized she was doing little more than teasing him. So she let him see her, study her as she took her time putting on her pj's.

Was this the right thing to do? She didn't know. And she had no idea if she was doing more harm than good when she let him touch her breasts, to feel them, their shape, their weight, their softness. But it felt right. His exploring hands weren't groping, his fingers, she imagined, were like those of a blind man trying to understand.

And the other wasn't much different. He had been looking at her crotch every chance he got. Eventually, she stood still for him, standing stationery like a statue so he could study their differences, could see how he might have been if only ...

Should she have let him touch her? She didn't think she had a choice. A simple touch turned to an exploration, his fingers tracing her edges, his tips gently probing her folds. She hadn't had a man in years. Is that why she let him? No, it was his curiosity. She let him lick her, tongue her, bite her on the lips. He was discovering how he should have been. When it was over, it was enough. He never did it again.

Erewon25
Erewon25
42 Followers