Jake

Every time I powder my balls, I think of Jake.

Well, that's not exactly true. Sometimes instead of baby powder for lubrication, I use Dove Men-Care moisturizing deodorant. Without something, especially right after my weekly shave, my scrotum tends to chafe against my inner thighs. Which is kind of OK, as it tingles, sometimes even makes me hard.

Which makes me think of Jake. Of his neatly trimmed jet black hair, alluring V-shaped face, smooth ivory skin, misty dark amber eyes, and pouty lips, always wearing that "what the fuck?" smile. Nice 5-foot 5-inch body. Compact and lean, but still soft. Appealing.

The thing is, when I first met Jake, he was Julie. One of 30 freshmen in my Intro to Music course, sort of music history and theory lite, all packed into one semester. I like teaching the course, welcoming nervous neophyte music majors to the U at 9 AM on their first day of classes. I like freshmen generally, especially in their first semester, before they learn the real power dynamic at play. How students can get a prof in trouble, even fired, just by going to the dean, making stuff up.

But back to Jake. Julie hung around after that first class, and shyly asked if I needed help with anything. There was a twinkle in her eye, like she knew something I didn't. Well, lots of people do. In addition to teaching classes and voice lessons, I'm assigned to conduct the worst choir in the music department, the one where anyone can just show up and sing. And then the chair evaluates me on how good they sound. Sweet. But, as registrations for the choir mean money for the department, and I'm low man on the faculty totem pole, it's my baby. It's also a hassle, so Julie's offer of help was welcome. There are always things to do, getting music folders ready, pulling parts from the library, penciling my expression directions into each one, sorting old music, erasing the marks the singers put in, and refiling it, the kind of tedious crap that is the worst part of my job.

As Julie walked to my office with me after class, she reminded me that we'd met previously, at a vocal festival I'd conducted in her hometown the year before when she was a senior in high school. Thus the twinkling eyes. Her quirky smile as she told me jogged my memory. I don't lie as a rule, so when I told her I actually did remember her it was the truth. She'd been assistant principal alto in the chorus, and I'd been struck by how she was so eager, bright-eyed and smiley, and had hung around me at the reception after the concert.

Anyway, she qualified for work-study assistance and we arranged five hours per week when she'd come to my studio and do projects for me. Julie was conscientious, competent, and friendly. Eager. Not flirty eager, just sincere, a nice young woman who wanted to be helpful, to please. She was really pretty, too, but that didn't matter.

I had no trouble finding things to keep her busy, and grew to appreciate her quirky, self-deprecating sense of humor, intelligence, and reliability. I liked her and looked forward to seeing her. And she obviously liked me. A lot, it seemed. Now, I know what you're thinking, dear reader. But the only way I'd survived for six years as an Assistant Prof, been promoted to Associate and got tenure just last year, was to maintain a very firm, proper barrier between me and my students, especially those of the female persuasion. So there was no hanky-panky going on between Julie and me.

By mid-semester I began to see the clouds forming. As I came to know Julie better, I sensed that something was troubling her. A lot. When I asked, she deflected, saying everything was OK. But the second, maybe third time I inquired, Julie split open like an overripe melon, and her anguish just gushed out. Once the water works began, I quickly closed my office door and grabbed my box of tissues. It was time to be the supportive, concerned faculty mentor I am. Julie's pain, frustration, self-doubt, tortured struggle, and angst just poured forth, and, when she leaned into me and put her arms around me, needing comfort, I held her. It felt nice to be supportive, to be there for her, and it really seemed to help.

Once she'd calmed a bit, when she could talk between sobs, she explained. I'd heard that some people feel they are born into the wrong body, with the wrong sexual equipment, but I hadn't really thought about it. Never having had such doubts myself, I had no idea how the conflict could be so debilitating, so horrible. But it clearly was for Julie, who told me right then and there that she wanted me to call her Jake. Call him Jake. Evidently the crisis in my office was the turning point, and she, he resolved to make the change and begin living as a man right then and there.

I told him that I would change the name in my grade book immediately, call him Jake, and do everything else I could to support him in the transition. When he hugged me harder, snuggling closer in gratitude, I eased him to the side so he wouldn't feel the erection that the proximity of a very attractive, vulnerable, sweet, likable person with a pussy and cute little boobs had invoked.

Jake spent even more time in my office after our talk, just hanging out. It was a haven for him, a place he could be himself, certain of support. I saw in his eyes that he was ever-so grateful, and truly liked me, maybe more. Though at 30 I was 12 years older, I felt a real bond, a friendship develop between us, and the feeling of being there for him, providing essential support, was very gratifying. I found myself looking forward to the times when he'd show up for work.

To tell the truth, I had some trouble changing my thinking, conceiving of Jake as a guy, as ever since that hug, the feel of a soft, warm, appealing body melding to mine, I'd had to struggle to keep my barrier up between us. I wasn't worried, though, as I'd always been able to maintain the wall between me and all my other students, some of whom were truly tempting and overtly friendly, if you catch my drift, and so I just ignored my attraction for Jake and kept plugging away.

Until the vocal festival. Every fall, select members from a bunch of area high school choruses come to us for a day of singing, making new friends, learning more about music, with a fun concert at night. As there were too many singers for one choir, I was assigned the other, the one that had the second-flight students. Our senior vocal prof did the cream chorus; I got the milk. No problem. That's how seniority works. Jake was my gofer, especially helpful, and I needed it, as the festival was a big deal, one of our department's major recruiting events for the entire year. It was essential that things ran smoothly, that the prospective students had a good time and liked me.

It all went well until lunch. As I dismissed the choristers - they were to eat at our student union, so they could see how wonderful it was, like everything else here, so when they thought about what college to attend they'd want to come our U - I told them that that they should follow Jake. That she would lead them to the cafeteria.

Crap! As soon as the word escaped my lips, I immediately corrected it, but from the look in his eyes, I knew damage had been done. His friend, confidant, mentor, his trusted ally had betrayed him. Though at least I hadn't dead-named him and called him Julie, I wanted to die on the spot, shrivel up and sink into a hole, but Jake soldiered on and led the students away.

Now, dear reader, though Jake had cut his hair shorter, dressed like a guy, and affected a male persona - including a raspy voice, as low as he could manage - I'd have bet that most of the high school kiddos suspected he might be a she, and probably didn't give a whit. I sure didn't. But I knew Jake did.

The explosion didn't come until that night, after all the high schoolers had left, everyone else had gone home, and Jake dropped off the last of the music folders in my office. I'd felt terrible all day about my blunder, and was so distracted that I had to really concentrate so I didn't screw up. I'd thought endlessly about how to apologize and decided that just being honest was best. I told Jake that it was a slip of the tongue, that I was so terribly sorry, that I just accidentally reverted to how I'd first known him.

He dropped the armful of folders and turned away. From the shaking of his shoulders and gasping sobs, I gathered that my approach might not have been best. I walked to him, put my hands on his trembling shoulders, and whispered, "Oh, Jake. I'm so very sorry. Please forgive me."

He spun quickly, swatting my hands away from him, and bolted for the door. I leapt after him, and slammed the door shut, tearing the knob from his hands. "Jake, we need to talk about this. I won't let you go until..."

He lunged into me, grabbed my cheeks, and his lips on mine ended my sentence. When his body melded to mine, rubbing against me hard, my vaunted wall of impersonal reserve was crushed between us and collapsed to rubble.

Monday morning, three weeks later, Jake followed me to my studio after class, as usual. Also as usual, once my office door closed, Jake was on his knees and had my cock in his mouth. I knew it was risky, but that was part of the thrill. Besides, in the ten minutes between classes almost no student ever came by, and we both just needed to do what we needed to do. I'd been hard and dripping the last five minutes of class knowing what was coming, so Jake didn't need much time to get me close.

Once he had me twitching and moaning, and plenty wet, he spun around, dropped his pants, leaned over my desk, pulled out his butt plug, and guided my cock into his anus. I wrapped my hand around his hip, between his legs, and frigged his clit as I pumped his ass.

We came hard and fast, and quickly rearranged our clothes just in case somebody actually did drop in. Jake plugged himself first thing. It went in easily, as his asshole was still gaping from my cock and lubed with my cum, and he, again as usual, wanted to keep my semen trapped inside him. It would make our afternoon session easier. He wouldn't have to get me slick with saliva so we could fuck again. The idea of it, his trapping my cum in him so he'd be ready for another deposit, always kept me on edge all day, and often gets me hard now.

Dear reader, to be honest, I'd rather have been fucking his pussy. Jake did let me eat it, which I loved as it is truly luscious. Beautifully formed pink labia, delectable sweet, pungent taste, tight tempting hole, and his clit was really big, almost a tiny penis, even before the surgery he planned to have to augment it. He would come SO hard and so many times when I'd suck it into my mouth and flick the tip with my tongue. I had to make sure no one was around when I did that, though, as he couldn't help but make too much noise.

Even though I'd told him I wanted to, Jake wouldn't let me fuck his vagina. It would make him feel too much like a woman, which he didn't want. That was fine with me. Everything he wanted was fine with me, as, on the night of the festival, when he melted into my arms, so vulnerable, hurt, but so warm, soft, and sexy, I'd just totally fallen in love with him.

I certainly didn't try to, and did my best to undo it once I realized it had happened. But, something about holding him, soothing the hurt I'd caused, being a healing salve on the anguish from his whole life of being made to feel odd, different, even sinful and despised, just made my heart move. Irrevocably. And, dear reader, you know that love finds its own way. Plays by its own rules.

And the excellent blowjob Jake gave me that night sealed the deal.

After our ferocious sex the night of the festival, when he'd sucked more cum out of me than I believed was possible, and I reciprocated by finger fucking him like an animal, our sex life progressed. We started with mutual hand jobs and oral. As he wasn't on the pill, and didn't want to make love as a woman, coitus was out. Also at first, until he began using the series of ever-larger butt plugs, his anus wasn't stretched out enough to accommodate my girth, so we just used our hands and mouths on each other.

By the second week after the festival, however, we had established our routine of the after-class fast fuck to take the edge off the white-hot passion that we seemed to kindle in each other. But it wasn't until a week after that, when I'd figured out a way to sneak him into my apartment without being seen, that we became truly intimate.

That Saturday we had the whole day to ourselves. After a quickie to bleed off the excess tension, we were lying in bed, fondling, kissing and licking each other everywhere, and he sucked my balls into his mouth. He always seemed fascinated with the male sexual apparatus, probably wishing he had his own. Having my testicles eaten felt weird, but nice, and he seemed to get off on it. After he'd made me hard and taken care of it, I dozed, only to awake to the feel of my electric razor on my mons. Jake was shaving me. As he did, he explained that, though he liked taking every part of my sex into his mouth, the hairs tickled and got caught in his throat. So he would shave me, every Saturday. After which he'd use baby powder to dust my scrotum.

That day was the first time I really sucked his clit dick instead of just licking or frigging it. I stopped after his first orgasm, slid up his body, and laughingly told him he just had to keep it down. He promised he would try, really hard, and wanted to practice. Right then. He did better, but still I hoped my neighbors were out. Those early Saturdays together were truly wonderful, the rosy bloom of fresh love keeping all concerns at bay.

Even so, I was relieved when the spring semester started, because Jake wasn't in any of my classes anymore. My having an affair with a student, any student, was bad, but one over which I had grade authority would make the administration take special notice. As in firing my ass if they found out.

Our first Saturday after the holiday vacation was memorable. I gave Jake his Christmas present, a big Hitachi massager, and, after our usual fast fuck to relieve tension, we tried it out. It was amazing how effective it was. He came and came, big jolting, leg shaking, full-body trembling orgasms, and he was so out of control that he accidentally bit my hand when I covered his mouth to keep the neighbors from hearing. Watching him come was so exciting that I got hard again, and we took a nap in each other's arms after making love again.

I awoke to see that mischievous, what-the-fuck smile on his lips. And feeling the Hitachi on my cock. It was as flaccid as a wet noodle, but Jake just held the thing on the spot on the underside where the head meets the shaft. Yeah, that spot. He knew about it because of how I'd twitch and jerk when he licked it. Anyway, I was skeptical about the massager doing anything. But, wow, somehow the vibrations just seemed to jostle the nerves in my penis all the way down into my balls, and in just a few seconds Jake began giggling as he watched my penis start to grow.

It was weird how just vibrations seemed to have the same effect as friction, how it just seemed to pull the cum out of my balls, up my cock and make it disgorge. It didn't really shoot - not much velocity or distance - but Jake really got into how he could make my cock get hard, twitch, and ooze semen to his command.

Vibrating my penis till it ejaculated became one of Jake's favorite things. He'd just watch me react - twitch, groan, and jerk - as he made my cock grow, then stroke my cheek when my semen poured out, but other than that, he wouldn't touch me at all. Of course I'd often get hard from just the look in his eyes when he thought about doing it, so he'd get me off some other way and then, after giving me a few minutes to recover, he'd take his wand and perform his magic trick.

We celebrated his 19th birthday the third Saturday in February. Though the passion was still running hot, things had plateaued a bit, and some frustrations - due to our inability to be ourselves in public, and the inevitable conflicts borne of 12 years age difference - were beginning to surface. Anyway, to keep things developing, to take the next step, I gave Jake his presents. Some penises.

The outfit was a traditional strap-on with heavy straps and three sizes of cock. The starter model was black, the middle-sized blue, and the big fella was red. In preparation, I'd been working my way through my gamut of butt plugs, and felt that I'd probably be able to take the largest, which was almost as big as mine. However, having never been screwed before, I was leery. Anyway, Jake loved them all and was hot to try them out. I wasn't sure I'd like getting fucked, but we'd talked about it, and I knew Jake wanted it. Badly. So I went along, wanting to please him. He wanted to start with the biggest, of course, but I insisted on the blue beauty for our maiden voyage.

It was plenty big, dear reader, let me assure you. Especially when Jake truly got into it. God, did he ream me! He loved it so much that he wanted to screw me again just an hour later, but I was so sore that I demurred. Well, actually, I bargained.

I don't know if I'd actually planned what happened, but it worked out just as if I had. Jake really liked how I moaned and winced as he pumped me, how my eyes lost focus when he drove it in, and he pestered me relentlessly all day to do it again. Well, to tell the truth - which, as I said before I usually do - I'd kind of liked it. Several of my past girlfriends had mounted up and ridden me like wanton cowgirls, and it was pretty obvious just who was fucking whom. So being actually fucked wasn't so different. Well, it was, of course, but it felt OK and made Jake happy.

However, what I really wanted to do was to fuck Jake in his pussy. To feel that plump, tight vagina encasing my dick, making it shoot, empty into him. What the hell, I thought. He had the equipment. Why not let me use it? He'd never liked the idea before, but I talked him into it. Since I was letting him fuck me how he wanted, why not reciprocate? We loved each other and wanted to make the other happy, didn't we?

After he used that red monster on me - OMG, was that an experience! - it was my turn. Of course, he wasn't on the pill, so we had to use a condom. He had wanted to watch my face as he fucked me, and I wanted to see his, so we did it like missionaries. It was wonderful, completely fabulous, and I made Jake come by thumbing his clit as I pumped his pussy. I truly loved it. And, though he didn't admit it, I knew he liked it, too. The condom kind of diminished it, made it less exciting and stimulating, but still, it was the best sex I'd had with Jake.

Now, I admit that I probably should have stopped what happened next, but it was really late that same night. He was able to stay over, had told his roommate that he was going home for the weekend, and we'd both drunk a hell of a lot and smoked quite a bit. As we were kissing sloppily, happily, lazily fondling each other's favorite parts, one thing led to another. I'd just finished sucking his clit, and he'd come really hard, thrashing, laughing out loud, really drunk. It was so nice.

As he settled down, I stayed between his thighs, nibbling, and gazing at his pussy. God, what a beauty! He'd been very aroused, and the scent and taste of his sex drove me wild. Made me do it, suck him off again.

After he quit shaking, Jake sighed, closed his eyes, pulled me up next to him, and just lay on his back, rubbing his thumb across the slit of my erection, spreading the pre-cum all over. Getting me really hot. Next thing I knew I was on top of him, and he spread his legs wide and pulled his knees up. He was totally wet and slick from coming, and, though I don't remember aiming, next thing I knew my cock was buried in his pussy. He opened his eyes and kissed me, and that did it.