Jake

Why is doing something you know you shouldn't do so delectable? Something about it being forbidden, naughty, risqué? Probably. I don't know. Anyway, Jake was lying there under me, naked, flushed and aroused, his nice little pink nipples hard as pencil erasers on his nice little boobs. His sexy legs were wrapped around me, and his quim was holding me oh-so-tight. It was hot.

Jake kept writhing and moaning as I pumped him, and his vagina just seemed to be sucking on my cock as I pushed it in and out. It was as though some mystical vacuum inside him simply pulled the cum out of me. Just as I started to shoot, trembling and gasping, Jake opened his eyes, wrapped his arms around me, and watched my eyes try to stay with his as I shot and shot. I could feel how he used his vaginal muscles to squeeze my cock, over and over, draining every drop of cum out of me. Into his fecund, 19 year-old pussy. I'll never forget the look of satisfaction on his face at how he drained me, controlled me, made my cock do what he wanted, just like he did with the Hitachi. Talk about life's peak moments. I'm dripping now just thinking about it.

We did it four more times that weekend. When I woke up hard in the middle of the night, his cunt was still oozing with my cum, and I slipped it into him from behind. He sighed and stroked his clit so we came together. When I woke up in the morning, he was riding my morning wood and actually came before I did. We screwed once more after lunch, slowly, starting with him on top before switching to doggie. Just before he came, he took my hand and put it on his breast. He made such sweet sounds, and his vagina squeezed me so delectably when he came.

I was truly surprised at how much Jake got into it. We didn't talk about it, but I knew that it had changed our relationship, making love like a man and a woman. I was amazed and delighted that he accepted it. Even liked it. Really liked it. Our last time started out as just our goodbye kiss, but the flames rekindled, and after he'd dropped his pants and leaned over, he grabbed my cock from behind and put me in his pussy, not his ass. It went as hard and fast, and as wonderfully, as the other times.

Jake waited in the car while I went into the drug store and got the morning-after pill just before I dropped him off. It was the sweetest goodbye kiss ever, as we both knew we could hardly wait until tomorrow.

I could tell that something was wrong Monday morning when Jake came to my office to do some work. After the door closed, I took him in my arms and kissed him, thinking that we'd have our usual quick fuck, maybe in his vagina again, and then get down to business. When he resisted, didn't kiss me back, I asked what was wrong. Once again the overripe melon burst, and the anguish gushed out. He hadn't been able to sleep at all since we'd parted the day before, his inner conflict was so intense.

Jake just couldn't stand that he'd enjoyed making love as a woman, having me fuck him in his pussy. That he'd liked it so much he even initialed it, so that we kept doing it. And how, once he was by himself, he kept thinking about it, and it made him get aroused, wet, wanting it to happen again.

I was thrilled, as fucking Jake in his vagina was the best sex I'd ever had, and it was hard to imagine anything ever being better. I didn't even want to try to imagine anything better - one can't improve on perfection - and I hadn't been able to think of anything else since. I'd never felt more in love and knew somehow we would work this out.

I was much less thrilled when Jake told me what he'd decided. In a nutshell, because I made him feel like a woman, react like a woman, want to have sex as a woman, and at his core he knew he was a man, the only solution was for him to not be around me. To transfer to another school and never see me again. He'd already filled out the paperwork that morning.

I desperately tried to talk him out of it, to get him to wait, give it some time. I promised that I'd try to change whatever it was I did that made him feel that way, that I'd do anything, everything. Just please don't break things off. But Jake was adamant. He was stiff as a board when we kissed goodbye for that last time, steeling himself from feeling anything. From reacting to my tears, sobs and pitiful pleas.

Now, two years later, I still pine for him. Or her. With the help of Steven, my shrink, I've come to realize that I loved Jake as a girl, not a guy, and that we probably didn't ever have any chance for a future together. At first, gender didn't matter to either of us; we just fell in love as human beings, and for a while its power masked the inevitable conflict.

Imparlibidinous. That's the term Steven used to describe our relationship. Though it technically means that one person in a relationship wants sex more than the other, in our case it meant that I wanted, truly needed, a relationship much more that Jake did. I'd already had three serious loves, and they all had left me, so I was feeling desperate for something to work. Jake was just coming of age, finding himself, in his first truly serious relationship. When he saw that it was fatally flawed - that I really wanted him as a woman - though it was painful, he could leave. And did. He absolutely had to. Steven got me to understand that there was no hope of ever reconciling, that I needed to move on. Though it wasn't easy, I did.

Jake and I are Facebook friends, now that the pain and anger of the breakup has faded. Time heals, I guess. He's in a really solid relationship now, I've contributed to his mastectomy and metoidioplasty fund, and I'm truly happy for him. If it works out, I'll certainly go to his wedding.

I'm doing all right, too. Finally. The new job is OK. Of course, since it's not tenure track and is at a small, private school, it doesn't pay much, but it's good to have contact with students again after being summarily fired from the U after the shit hit the fan. My fault, mostly. I still don't understand why I stayed in bed for so many days, and just didn't show up to teach my classes and conduct that crappy chorus. At least my insurance paid for the sessions with Steven.

I'm seeing Mary again tonight, and I like her a lot. She's really helped me get things in perspective. Steven helped me to understand how I became too dependent, too clingy, too intense in my previous relationships, and I've been much more at ease with Mary. We had sex for the first time three weeks ago. It was terrific - she's really hot and loves how I take so much time eating her - and I have high hopes that things will keep going well. Of course, I'm being careful not to push, or get too intense.

Anyway, anticipating that things will go as I hope tonight, once I finished my shower, I shaved my scrotum and mons. Then powdered my balls. And thought of Jake.

But it was remembering the taste of Mary's pussy that got me hard.