The Story of My First

by

Caution: This True Sex Story contains strong sexual content, including Ma/Fa, Consensual, True Story, First, Safe Sex, Oral Sex, .

Desc: True Sex Story: This one's a little different in that it's not technically fiction. Names have been changed to protect the innocent, but by and large it is a rumination on how I misplaced something very important. It was my virginity. I put it in a girl's pussy and never saw it again. Read on for details.

I would like to tell you that it was an occasion to make angels swoon. That it was love, true love, and that she and I are still together; that the glories of romantic idealism swept the field and took the victory. I would like to tell you that it was perfect.

But this is real life, not a story.


I met my first lover through a dating site. On the surface of it, things were pretty normal: We e-mailed back and forth for a while, and then had phone calls. Then we met in person, and things began to go from there. On the surface of it, things were pretty normal.

Except for how they weren't.

First off, she contacted me. This is wildly unusual, because I am a bespectacled nerd; in fact, to my knowledge, only one girl ever has been attracted to me instead of me being attracted to her. Secondly, I wasn't sure I found her physically attractive. Third, I picked up things from her profile that made me leery, indications of personality traits I might not agree with. These would prove meaningful in the long run, but I decided to take a chance, especially because of the next thing: there were fair indicators on her profile that she was open-minded about sex—a major turn-on to a 27-year-old virgin like myself.

And lastly, things moved quickly. Most people on dating sites are fairly careful; the Internet is still a new technology, whether we like it or not, and people are wary of being bilked, tricked, misled, finagled and otherwise presented with foul play. I don't blame them. The first time I met an Internet acquaintence in person I was sixteen, and even at that young age I was aware of how easy it is to mislead people over the net. I was right, too; my friend was not the long-haired, confident teenager I'd envisioned, he was my parents' age, and on crutches from his cerebral palsy. Now, he proved just as cool in person as he was online, if not cooler—he even befriended my parents—but the point to be borne in mind is that Internet appearances are deceiving.

And all this applies to dating sites as well. As such, your average woman will often e-mail back and forth for quite a while before suggesting, or being open to suggestion of, more direct contact. So, it was a bit of a surprise to me when this new contact of mine offered me her phone number on the very second e-mail. For the Internet, this is about as forward as sleeping with someone on the second date.

Of course, she did that too. But we're getting ahead of ourselves.


We met on Saturday night, at a coffee shop local to us. She was quite late, which—in the interests of fairness—I must admit I found to be a turn-off. I believe this was a one-time thing, though, as for the rest of our time together she was largely punctual. We had spoken over the phone the previous evening and the conversation had flowed freely; this same pattern continued in person. I was pleased to note that my concerns about being unattracted to her had proven unfounded. (She is Asian, and—despite being about as Americanized as they come—I have found the "Asian girl" fetish especially compelling.) We were together that night until close to 3 AM.

I have been engaged, a fact which has been documented in some detail, and there are some things Christina (not her name; in fact, all the names in this document have been changed) has in common with ex-fiancée, whom we shall call "Caitlyn." Both of them are Christian and are active at their churches as musicians; both of them share the same frames: slim, small-breasted but with a wonderful derriere (it was Caitlyn and another long-time crush, "Meredith," who first made me partial to the pear-shape body plan). But in other ways, Caitlyn and Tina were as different as it is possible to get. Caitlyn was short enough to tuck under my chin, pale-haired, light enough for a nerd like me to pick up in my arms, and physically quite shy, not just due to her religious beliefs but because she actually has an anxiety disorder concerning physical touch. (Sometimes the poor love would have panic attacks while we were making out.) Tina was tall enough to reach my nose, had the dark Asian hair and a vivacious personality. She was open-minded, energetic and not in the least shy. Caitlyn did not let me kiss her for three months. Tina I kissed within 3 hours of meeting her.

After we were done with the coffee shop, Tina tried to draft me into doing some karaoke at a place downtown, but (to my relief) they only offered it on Sunday nights. Instead we ended up back at my place, trading funny YouTube movies. Once we ran out of those, we were left staring at each other, smiling, and from there it was obvious. It was the first time I had kissed anyone since breaking up with Caitlyn almost exactly three years ago. (She and I ended things the Monday after Thanksgiving; Tina and I had our first date the Saturday before it.)

After things had begun to speed up a little, we stopped to talk. Specifically, Tina wanted to know what I was thinking about how far we might go. I had told her already that I was a virgin, and she admitted to being intrigued by this. Having said that, she had a bit of a complication to admit to: she was still involved, non-exclusively, with another man, whom for simplicity's sake we will refer to as Other Man. It had been his suggestion that they date around, but so far as we could tell, he had meant it as reverse psychology: he'd date another girl, Tina would get antsy, come back to him, blablablah. Instead the opposite happened. Needless to say, he was a little perturbed when she officially broke things off.

I was also somewhat haunted by the ghost of bad decisions in the past, which I confessed to Tina at some point in the relationship, maybe even that very night: once, when seventeen, I had had the chance to make romantic overtures with a girl I had been lovelorn over for well over a year. But I made a botch of it by attempting to open sexual relations instead of romantic ones. My intended lover resisted, protested ... relented, saying words to the effect of, "Let's get this over with." It was my first (and for a very long time, only) sexual encounter. We did everything leading up to intercourse, but we didn't go the whole way because I had no idea where to put it and she (for obvious reasons) wasn't going to lend a hand. At the time I was ecstatic; today it shames me to look back on how oblivious I was, and how easily my eagerness led me to inflict hurt and pain. And this is part of why I didn't protest one bit when Caitlyn announced she was waiting until marriage: I knew what could happen if I didn't listen.

Long story short, we agreed not to get into anything that evening, and to merely sleep in the same bed together. That may sound surprising, especially in light of my protracted virginity, but at the time I didn't feel a great deal of pressure to push. Tina and I had already gone farther in one night than Caitlyn and I had in basically our whole relationship—not just in sleeping in the same bed, but in that Tina allowed me to put my hand on her breast—and we had known each other for only a few hours. I felt confident that things would work out.

So we curled up in my bed, with clothes on. It was the first time I had ever slept in a bed with a woman ... Or, at least, it would've been, except that I couldn't sleep, not lying on my side like that. Neither could she. (The clothes probably didn't help; I sleep naked.) At about 2:30, she got a phone call from Other Man, which was a slap to her conscience; At 3 AM we were still awake, and she made the decision to go home and prep for church. And that was our first date.

Nonetheless, we made arrangements to meet again the next evening, this time for a proper dinner date. I don't remember if we went anywhere after getting home from the restaurant; all I remember is that we ended up back at my place, making out again. We were on my bed, and things were getting pretty heavy.

"What do you want?" I asked her.

"I want you," she said.

In a story, the tone of her voice—husky, breathless, needy—sets the hero's heart racing. In a story, the hero feels adrenaline jolt through his veins at those words—and probably through his cock as well. In a story, the hero says something appropriately charming and manly here, and sets the scene for the erotic ravish-fest that's about to take place.

What I said was, "Okay."

We took off our clothes—she spared me the trouble of bra-strap tangles by taking it off herself—and we began the process of getting to know each other. If this were a story, I'd have been delighted, enraptured, smitten; she would have been perfect in my eyes. But, alas, she wasn't. I remember being a little disappointed with her breasts, which were small even for an Asian. On the flipside, I remember being delighted to discover she shaved her pubic hair; I've always liked that look. Likewise, she had a large pubic mound, one that actually rose in altitude above her navel, and I liked that too.

I didn't say anything about my little nitpicky preferences. Even I'm not that stupid. Besides, "When you're in bed with an ugly woman," a clever man once said, "the best thing to do is close your eyes and get on with it." And Tina is by no means ugly. She's lovely. She just ... isn't my type.

.... There is more of this story ...

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Story tagged with:
Ma/Fa / Consensual / True Story / First / Safe Sex / Oral Sex /