Virgin
2010-04-10

[The following story is a true account. All names and locations, as well as revealing details, have been changed. ]

I was under an enormous amount of pressure to have sex as a teenager, and ninety-nine percent of it came from within. Not having come from a family who looked down on sex before marriage, or sex before adulthood (as long as it was safe, and in a perfect world, not rampantly promiscuous), I had no barriers other than my own self-esteem and social problems. I was not unattractive, not without the personality that would appeal to an ideal female counterpart; the only things I lacked were confidence and the ability to move on.

My habits of infatuation were indefatigable at best, and mostly aimed poorly. The girls I would find myself 'madly in love with' were the girls who didn't see me as their type--while all around me were honestly better options that my unyielding romantic heart refused to acknowledge. In retrospect, and only in retrospect, this was a tremendous problem. Never did anything work out between myself and on object of my smothering lambasting of love, even if I wound up dating these targets. I was too intense.

This, coupled with my fear--my actual fear--of penetrative sex, kept me a willing virgin all through my first three years of high school. Yes, willing; I have always been one of those quiet, obedient kids who listened to D. A. R. E officers and health teachers. I've never smoked, never drank, never done drugs, and most importantly, at age 17, never had intercourse.

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Impregnating a girl or transacting disease were waking nightmares every time the idea popped into my head.

Fortunately, the only girlfriend I ever came close with was my girlfriend in my first half of senior year, a blond named Lana. Lana professed to also be unready to lose her virginity, though my suspicions to the contrary have stacked over the following years of knowing her. But when pertaining to me, intercourse was the only thing we never did. Long, starving sessions of oral sex in my bed and backseat of my car, hours-long sessions of wearing nothing in the dark. At one point, in our sweatiest of these makeout sessions, my penis and her vulva seemed to operate without our consent. Almost painfully hard, darkening in redness, my penis ground lengthwise against her labia and clitoris, occasionally nudging at her vagina. She weakly, with very little conviction, told me that she didn't want to have sex, and my will power was in a battle of attrition against my reproductive instincts. We never did, but something about Lana's failing resolve tells me that if my will power hadn't won that battle, she would have consented perfectly.

Anyway, we didn't work out. Long story, not sexual.

The one percent of outside pressure came from my good friend Caleb, who'd been sexually active since he was twelve. At one point when he and his brother were over at my house for a movie, I came to the realization that my fears of intercourse were gone, and I needed to get laid. Caleb said, 'I can definitely make that happen for you, dude. There's this girl, Rachel Griggs, and seriously, if you walk up to her at a party and just gesture at a bedroom, she'll take you in there and fuck you.

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'

I'm seventeen during this conversation. This Rachel person, whom I've never met, suddenly becomes a magical fairy, a hostess into the world of adulthood. 'How can you make that happen?' I ask.

'Fuck, dude. Let me call her. She's probably at a party right now. '

He wound up not calling her, at my behest, and she never came up again. But there was a part of my brain, and my crotch, that desperately wanted to go dump my virginal wad into the nearest willing organic receptacle. That should have scared me, but it didn't.

. . .

Near the end of the school year, I met a girl in my class whom I'd never met before named Julie. Julie and I fell fast for each other, the kind of thing that you see happen in high school movies. This had occurred, though, no more than two weeks before we graduated.

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Long phonecalls lasted between us, long musings on the future. In my future was a big nothing: as an artist of sorts, with no financial backing, I had no plans of college. The world was as much of my oyster as brochures would have you believe. So, meeting this girl on the eve of such a big life change was portentous of a magical future with her, fraught with the perils and wonders of a long relationship that poets could write about.

And since this is being shared on a sex site, let me tell you about that whole realm of things.

Julie's body, out of all the bodies I'd experienced before and all the bodies I've experienced since, is one of my top three bodies that I've ever had the pleasure of seeing unclothed and touching. Parts of her were curvy, parts of her were lean, parts of her were delicately, decadently plump, and parts of her were lithe and ample. Her breasts, medium in popular hyper-male measurements, but large to my hand (sorry, I don't think I've ever taken the tedious time to catalog any girl's numeric measurements), were perfectly shaped and lovely, with two or three moles to characterize. Her nipples were small, sensitive, and her navel was a sheet of healthily toned flesh on which I could plant kisses and rub my cheek and chin with just as much pleasure as a hand on my cock. The taste of her vulva was perfect, and the thighs to either side of them were lush, strong, and squeezable. To top it off, though I have never put too much stock in a girl's ass (but have appreciated many), hers was just fun: not prominent, but not emaciated. It was small, but not disproportionate, and there was enough there to, if I had done her doggy-style, cushion my thrusts with an immaculate fit.

As I said, top 3 bodies.

Brief reveal: I think I may have masturbated in a somewhat harmful way growing up. With my index, middle, and ring finger, I would press upon the sensitive underside of my cock with a good deal of force, and as a result, I think I may have numbed that part of me a bit.

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That, and I'm circumcised, which apparently removes a fraction of sensation. Anyway, what that leads up to is a sad, sad fact: I rarely orgasm from blowjobs. They feel great, believe me, but it's never. . . it's never enough.

Julie, though, was incredible at oral sex. Her rich. full lips, her singer's tongue, and her awesomely low gag-reflex got me to come every time she put my cock in her mouth. She had a couple inhibitions as far as sex went, so she never went all out, such as fondling my balls or anything, but she could suck me dry in three minutes maximum. And she swallowed, which in women is something I see as incredibly sexy and empowering. Yay you if you're a girl and you swallow. Or if you're a guy and you swing that way, I guess.

And she was eager for it too. One time, one of our first trysts, we were on her bedroom floor.

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'Take it out,' she suggested.

'Are you. . . are you sure?' Since my record of pseudo-sexual encounters was still very short at this time, I thought that routine was everything. Therefore, I thought I always had to go down on a girl before she went down on me. 'I was thinking I'd eat you out first, and then--'

'Shut up,' she said. My god, the way she said that, pressing her face into mine and pushing me down flat from my sitting position, was one of my hottest moments as a sexual being. Julie pawed at my belt buckle, unzipped my shorts, and dove upon my cock with such love that it hurts to think about it.

I came in about forty seconds.

Julie and I never had sex, a factoid that is no doubt provoking your thought: well, when do we get to the good stuff? Hold your horses. It's coming (no pun intended). As I said, she harbored some minor inhibitions after a rough close call with a male friend of hers that was almost a little too forceful. Nothing happened, thank goodness, but she did get a bad taste in her mouth about sex from that point on. But once I gained her trust, she was a little more inclined to acquiesce.

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One afternoon, I asked her, minding my pressuring techniques and holding back, if she wanted to have sex.

'I. . . I don't think we should,' she said, toying with her hair.

'Are you sure? Because I think I'm ready for it, Julie. I'm ready for it with you and no one else. No pressure, of course, but if my first time was with you, that would just make my whole life. ' Sappy, I know, but that's how I was when I was seventeen.

She loved me as much as I loved her, I know that, but she rarely expressed it in words. Here I received her 'mirroring' expression, which said, 'Right back at ya. ' Aloud, she sighed and asked, 'Do you have a condom?'

Damn it all to fuck. Quick anecdote: since my entering high school, my mom had been on top of the whole if-you're-gonna-have-sex-you-do-it-safely thing. Every year, she brought home a package of condoms to give me, throwing out the unused expired packages from the previous year. It was embarrassing, but I thanked her for them every time.

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Always looking out for me. But this year's package? Gave them to Caleb the week before because he ran out, and I thought I wasn't going to need them any time soon.

'Fuck,' I said. 'No, I don't. '

There went the second close call.

Julie and I broke up near the end of that summer, and it wasn't the best breakup that I could have asked for. She granted me leave to have a non-intercourse 'severance pop,' in which we mouthed each other off one last time. In the future, she and I would date again and have sex, but that's for another chapter of my non-fiction. From here, let's get to your sought-after 'good stuff. '

. . .

I was in love with Julie, and I was in love with her hard. Losing her was like a spear through my heart, and my stomach; I lost fifteen pounds, and I wasn't overweight to begin with. I moved to a new town, wasting away in my new place, having only AOL instant messenger and a handful of old friends' screen names to keep me company.

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One friend I chatted with was a girl I'd met that summer while I was dating Julie, a girl named Chandra who used to come into the restaurant I worked at. She had dyed-black hair, cut pixie-style, her ears laden with studs and rings, her wrists looped with countless bracelets. Very much a punkish sort of girl.

Truth be told, I don't know if she was sixteen or seventeen; she was old enough to drive because she picked me up from the airport, but she was still in high school. I never bothered to find out. Chandra was from home, and lived on the outskirts of town. She brought me to her house from the airport to stay for the night before I started looking for a place to move back home to (I was missing the familiarity and affordability of my hometown, something my depressed, non-working ass could have used). Her mom made us dinner, got us a movie to watch in her room. I could tell that he had affections for me, and she was definitely not unattractive to me, but I was steeped in my loss of Julie, and could think of nothing but an errant, stupid hope that she and I could get back together. Thus, my encounters with Chandra had to have been the most pathetic.

Chandra had first approached me with advice of moving on from Julie over AIM, telling me that I was a good-enough-looking guy that I could get any girl I wanted. My ego was in no mood to hear such flattery, but I took it in stride. My dick forced me to flirt with her mildly via this text, through which I ascertained probable cause of her attraction to me.

She talked about sex occasionally. She wasn't a virgin, and had been very active with her most recent boyfriend.

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That hunger of prospects invaded me. Thus, while we lay on her bed watching a stupid horror movie, I felt no apprehension in moving in to kiss her. Her kiss was timid in return, but we eased onto one another.

She made every measure to conceal her body from me as I took her clothes off: turned off the TV so the light wouldn't illuminate her features, covered as much as she could with sheets. From what I could see, from what I caressed and fondled and licked, she had nothing to be ashamed about. Pert, fairly large breasts, fit waist and wide hips, rounded thighs. . . everything that a guy could want. She even stopped me from going down on her because she was afraid of what I would think. Depressed, I had no motive to argue, and I lay on my back and let her suck my cock.

Still without the physical memory of sex, her blowjob was still a sensory load. I wound up having to jerk myself to orgasm into her mouth. She swallowed, even cleaned my cock and balls of the stray tendrils of come. With one of the few smiles I saw her punkish teenage face make, she told me how much she loved eating come, and how much she loved fingering it out of her and licking her finger.

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Apparently, she would have been okay having sex without a condom, so I kicked myself mildly this time, but I justified it by thinking of Julie.

The second time we hung out was at her friend Jenna's house. Chandra and I wound up under a blanket on one of Jenna's couches while a small get-together happened around us. Music playing, storytelling, long, loud conversations of these high schoolers. And here I was, a graduate, a depressed graduate with nothing to say. What they must have thought of me. . . Anyway, under the blanket, I teased Chandra's lips with my tongue. She returned the action. Let me tell you, next time you're kissing, try this: with lips just barely apart, take the tip of your tongue and run it along your partner's lips. Just the tip of the tongue, like you're prodding their lips, testing them. Move in lines, move in circles, let them do it to you. It's fucking awesome. Chandra and I discovered that on each other, and it got both of us hornier than fuck.

'I'm really wet,' she informed me.

I put her hand on my pocket before moving it to the lump of my jeans. 'I brought a condom,' I said. 'Should we go somewhere?'

Obviously, we should. The others would have freaked out if we'd started fucking with nothing but a blanket to stop them from seeing the action.

Chandra led me to Jenna's downstairs bathroom, left the light off. I tried to get her to suck my cock, but she was too eager. She pulled down her skirt and her panties. I felt her moistened clit and labia with my fingers, noting that she hadn't shaved probably since our first encounter. She pulled away and awkwardly positioned herself to sit on the floor.

'Come down here,' she whispered. 'Can you make sure the door's locked?'

I checked the knob; it didn't move. I then disrobed from my waist down, and with trembling fingers, put on my first condom. This feeling alone made the caterpillars in my gut metamorphose. Then finally I knelt down, felt her cold knees on either side of my hips, shifted my self down slowly, jerkily, so that my sheathed penis aimed so naturally at her vagina.

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I kissed her as I pushed forward, feeling her experienced vagina wrap around the head of my cock, so wet and bothered that the rest of me slid in. And my first thought, after all the masturbation, all the fantasies, all the porn, and all the real-life handjobs and blowjobs, was, Holy shit, I'm having sex!

Now, some of you male kids out there (because I know you're there reading this. . . this site isn't hard to get into, and I was on sites like these as far back as age 13) might read some of these stories and be like, 'You dudes are full of shit! I jerk off all the time, and I can never come more than once. Why should having sex with a girl change that? What's with all these stories ending with, "And then I was still somehow hard after I came, so we did it again?" That's just fantasy bullshit. '

Kids, no, it fucking isn't. It fucking isn't. You need to know that since discovering masturbation at age 11, there had been hardly a day in the seven intervening years that I had not had an orgasm. I was very familiar with the sensation, and as I noted before, part of my dick was a little numb. With Chandra, on this bathroom floor, I came within a minute, shooting into the condom, feeling the warmth of my own come filling the wrinkled gaps of the polypropylene on my dick. I lay there on top of her, breathing heavy, feeling her nipples through my shirt, kissing her neck. And my cock did not soften. For another couple minutes I lay there in her, licking her earlobes, kissing her more, thanking her, telling her it was awesome, and I still didn't lose my erection.

So I started pumping again.

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She later told me that she didn't believe me that I was a virgin because of this. Maybe she was a disbeliever too. But we started in missionary position, and then I had her get on top of me, then I got behind her, then back to missionary, then that one leg up and fucking her sideways thing you see in porn, then back to missionary once more before I came the second time.

It was, at the time, incredible. I pulled the condom off, flushed it down the toilet, and she licked my cock clean. 'Mm,' she hummed, 'it smells like sex in here. '

We got together for sex another two times after that, but couldn't go on much longer, either of us. That most recent boyfriend of hers was her equivalent to how Julie was to me. We rebounded on each other, delved into that need for sex, that need for attention when there wasn't the attention there from the people we loved. There we were, scrambling for each other on some bathroom floor while our first choices, our hearts' desires paraded over the earth in some other capacity, independent from us, leaving the temptations for their own good. Had Chandra and I only been so strong, maybe the ultimately regrettable collision of our bodies could have been avoided.

Maybe she hated it more than me. For me, it will always be a bittersweet moment, for it was my first time. And that is something that has to be really bad for you to totally regret. But for us, two teenagers who liked each other, who were consenting and ready, it was just your everyday normal fuckup.