The Story of My First

by CWatson

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.

I don't recall if she went down on me; I do recall that I went down on her. I don't think I was able to make her cum that night; hell, it was several weeks before I could even find her clit eliably, and one of the other things I discovered over the course of our relationship is that I actually prefer using fingers anyhow. But whatever the case, it wasn't too long before she whispered—that same throaty murmur—"Let's get a condom on." So we did, and she positioned me between her legs. This, ironically, was the one part of the proceedings I was familiar with; this had been one of Caitlyn's and my favorite arrangements when we engaged in the cuddling and making-out activities that substituted for sex.

Of course, Caitlyn and I had never been naked. Nor had she grabbed my cock and positioned it at the mouth of her pussy so that I could slide into her.

"Can I just stay here for a little while," I asked her, and she said I could, so I closed my eyes and simply enjoyed the fact of being there, her body wrapped around me. I have owned "realistic" masturbation toys (boredom will drive a man to amusing things), so I had some understanding of what it should feel like. And I have masturbated using condoms (boredom will drive a man to truly amusing things), so I knew how I would be disappointed with the sensations. In this, I was not, well, disappointed. I couldn't feel a whole lot of anything down there that was different than whacking off. The rest of it, though ... It's one thing to lie on your back and jerk off into the cold air. It's another to be on your elbows above a real live woman, feeling her breathe against your chest, feeling her hands in your hair, finding her lips under yours when you bend down to kiss her. And ultimately, that—not blowjobs, not orgasms, not her moans and sighs—was what I valued most about being her lover.

When we curled up in bed again, this time it was a bit more natural because we had no clothes on, but still I found that I couldn't sleep all tangled up with her. Neither, she admitted, could she. So I let go of her breast and rolled onto my back. Having said that, this was still the beginning of a number of semi-sleepless nights: not just because we would stay up late fucking, but because I wake easily. Even having a memory-foam mattress didn't stop me from blinking awake whenever she moved or rolled over, and—though I never asked—it's entirely possible she had the same problem. Fortunately both of us are relatively motionless sleepers, and as the weeks passed I got used to it.

When we awoke, of course there was the opportunity to do things again, but I had to make another embarrassing confession: there is, simply put, something wrong with my cock. Since before my ill-fated night with that one love interest (in fact, I once asked her if she had heard anything about things like this), having an orgasm results in a burning sensation along my urethra for as much as ten hours. It's strong for a couple hours after ejaculation; afterwards, it recurs with further erections. (Yes, including morning wood. Yes, enough to wake me up.) I don't know why this is; the one doctor I asked had no idea, and since I had never been in a position where this was actually hampering my lifestyle, I just learned to live with it. But simply put, repeat performances can be painful.

Did that mean I didn't want to do it again? Heck no! I gritted my teeth and went for it.

There were a number of firsts that morning too. Again, I can't recall if she went down on me our first night, but she definitely did that morning. It was my first experience with morning sex; it was also my first experience with cowgirl. She liked it a lot, but she had a tendency to sit back on my hips, causing my cock to bend painfully when she had me fully inside her; it took a while before she figured out how to seat herself properly. For the first time I found an upside to my pain-condition (whatever it is): it adds to my stamina. And then, when we were done, I got one of her firsts: she had never had a man soap her or shampoo her hair.

I was amused, but concerned as well. Who the heck had she been dating?

Tina is the eldest of four children. Her parents married unexpectedly because she happened, with her sister coming along two years later. The second pair (a second sister, and then finally a brother) were ten years younger and had not yet hit high school. This kept Tina in touch with the younger cachet and probably contributed to some of her attitudes.

Despite a Catholic upbringing, her parents quite clearly did not hold to the fornication prohibitions, and Tina took after them ... though, originally, the plan was to do the exact opposite. She simply lost her inhibitions one night in college, and off she went. Since then she had taken five lovers in eight months. Today I know the average American has nine lovers over the course of their life, but at the time, her total sounded like a lot. I was a virgin (or, eventually, barely-not one), and despite all the research I could do, there was still a lot I didn't know.

I also found out that Tina had once weighed quite a bit more than she had. During college she went vegan, partially as a way to control her food intake and eventually because she liked it; she also went on a weight-loss regimen and slimmed down to the size and shape I saw her as. A part of me still has trouble reconciling this; humans don't believe what they haven't seen with their own eyes, and I never saw her at her "chubby" weight, only a driver's-license portrait. But no woman is quite as maligned in our society as an overweight one.

This, sadly, extends to me too. In my case, I do have a semi-valid excuse: I'm a scrawny nerd made of fence posts. Attempting a physical relationship with a woman who is above a certain weight limit is simply infeasible. But, I'm shamed to admit, if I had met her at her old weight, I might not have given her a second glance.

And I know for a fact that Tina is extremely impulsive. This came up more than once in our conversations, and when I questioned its wisdom, she made it clear that she would not abandon it: it was too near and dear to her heart, too fundamental to her personality. I understood the impulse; there are traits I'm similarly protective of as well. But the trait itself made me wary. I'm methodical and cautious in my dealings; Tina, by her own admission, just goes with whatever seems best at the moment. It's a lack of long-term thinking, and I found it troubling.

Now, that's what I know. But what do I not know? Frankly, I have absolutely no idea what I don't know. There are a lot of facts concerning Tina and her personality that I am not privy to. After the break-up, I analyzed events exhaustively with those friends of mine who were patient (and/or foolish) enough to listen to me, and the problem I kept bumping up against was that there was much I simply didn't know. And, at the break-up itself, things moved fast—too fast for me to take notes.

But as I peered into the past in the aftermath, a pattern suggested itself to me, and I present it to you now.

I think that Tina was used to having mostly-physical relationships; by her own admission, Other Man was her first long-term relationship since becoming sexually active. I think she was mostly drawn to men who were interested in only one thing, which (I hope) made it a refreshing change to be with me; I did my darndest to be supportive of her lifestyle, her comfort, her emotional well-being. (I don't believe in doing things half-assed.) And I think she rolled this way because she, too, was mostly interested in only one thing.

Now, it wasn't just that she has quite a sex drive, though she does; her collection of toys is impressive, she loves anal, and (by her own reports) masturbates frequently when single. In my opinion, it's also that she was drunk on the power.

Think about it. A girl with a strong sex drive, which makes her every man's wet dream ... but overweight. And Asian overweight, to boot, which is about as awkward as you can get in America. Beaten down, unattractive in everyone's eyes, no self-esteem ... I know what that feels like. I've been the same.

And then she loses weight and suddenly, she's sexy as all hell. It's a known fact that men can get drunk on their own egos when they finally start getting laid; it happened a lot to a friend of mine, and even happened a bit to me. I think the same happened to Tina. I think she liked to maximize the sexual content of her relationships because it made her feel attractive. I think her favorite way to quiet her insecurities—which of course take the form of an overweight, unsexy Asian girl—was to fill its mouth with cock.

Again, all of this is just theory. I need to disclaim this not just because it's entirely possible Tina might stumble upon this story—and I hurt her enough during the break-up as it is—but because it's the truth: this is just a theory. I don't know the truth, and can't know it because I don't have the full body of fact. I only have a few scraps. But this is what fits those scraps.

Tina and I dated for a little less than two months, from the weekend before Thanksgiving to the weekend after New Year's. It was a pretty busy time: at my job, my boss had retired and her replacement had just come in, while Tina was battling finals and trying to make sure her credits transferred correctly so she could graduate. Also, the holidays happened, and since both of us are church musicians, there was a fair amount of running-around on that score as well. Despite this, we saw each other about three times a week. And basically every time we met, we had sex.

I learned a lot in the bedroom over those six weeks. I learned to find Tina's clit reliably, and how to bring her to orgasm. Once I figured this out, I did my best to make sure she came at least once every time we did it, but amongst the things I didn't learn was how to figure out if she was actually cumming or just faking it. (Not that a cock is a fine sensing tool anyhow.) Faking seems more likely than the alternative, which is that she was orgasmic enough to cum basically every time, even from penetration during missionary. But I don't see why she would've faked it in the first place. She claimed my cock (which curves downward instead of the normal direction) was perfect for her in that way. And, since I don't know any other facts or truths about the situation, we'll leave it at that.

I learned that I prefer using my hand to bring a woman to orgasm than going down on her. As it turns out, I'm not as fond of the taste of pussy as I thought I'd be, and my lips and tongue are harder to coordinate. Plus I get to kiss her or suck her nipples if my head is up north, or watch her face. I get to be more involved with the event, if you will, and I prefer that.

I learned that I prefer the style of sex known generally as "making love." This was the majority of our interaction. We only fucked a couple times and our one quickie left a sour taste in our mouths, because it was, well, rushed. There were a couple of reasons for that, too: one was that we had met for lunch before I left for work, and it was about to be our first-ever meeting where we didn't have sex. This caused me some insecurity, like I'd failed to perform. The second was the (pleasant, for me) discovery that her pussy is less stimulating than my hand. This stands to reason; not only do I know my own cock better than anyone else on earth, but I have control of my hand and can manipulate myself (or a toy) at will. Doing that with a pussy is a little harder, even if you're on top. The downside is that if you want to blow and go—which I did, under these circumstances—it's kind of not an option. I plowed at her singlemindedly for quite a while, and neither of us liked it, so we eschewed quickies from then on.

I learned to check expiration dates from condoms. The ones we used our first nights together had expired several years ago. (Like I said: unattractive nerd.) Nothing resulted, except me rushing out to buy a more recent box. We also shopped around a little bit to find something thinner, as I felt my extant ones were too clumsy.

I learned how a woman puts in a tampon. Tina was surprised when I wasn't scared off by her period. I bet most guys are ... but I'm not most guys. Since I'd been in long-term relationships before, it wasn't the first time I'd had a menstruating girlfriend. But it was the first time I'd been aware of it while it happened. So I learned how a woman puts in a tampon, because that's something every man should learn eventually, and I wasn't squicked out by blood during sex either. (Though I was wearing a condom, which might have changed things. It was her idea; she claimed she was unsafe whilst bleeding. I'm pretty sure that's not true, but after the expired-condoms thing I decided to let it go.)

I learned that a lot of things look a lot easier in porn than they are in real life. Doggy-style, for instance. We only did it a few times, and the third time she got too enthusiastic and yanked herself off me right in the middle of things. I would've been happy to just keep going, but she evidently felt ashamed and we changed positions. (Ultimately, I think I liked reverse cowgirl better when it came to fucking; I could see her pussy lips and my cock between them, which was incredibly hot.) Spooning was a challenge as well. It took us several tries to figure out how to get me into position. I hadn't realized, and she didn't work it out until later either, that I needed to be under her ass and come up. But we kept working at it.

I learned that her favorite position seemed to be cowgirl. While I don't know what was going through her mind, it was my habit to go for her clit once she climbed on board, so (if I may say so myself) part of the appeal was probably that she was almost guaranteed to cum. More often than not we'd switch positions after she did. But, again, I don't know her actual reasoning. A definite upside was that she was able to suck my nipples there, which (I found out) I really enjoy, but most of the time she was preoccupied.

I learned that my favorite positions were missionary and spooning. Yes, I am a guy. Hear me out. It's all about the focus. When we were in missionary, I got to be the star; everything was about me. Even when she was moaning, cumming, bucking under me, it was all for me, which is pretty good for the ego and not so bad for the sex act either. Conversely, when we were spooning, the opposite was true: everything was for her. I got to hold her, a major change from missionary where they were totally occupied holding me up; I could grab a boob in one hand and her clit in the other, wrap her up in my arms and focus solely on making her moan. The reason they're tied for first is because one or the other was more appropriate, depending on who wanted to be in the spotlight that day. Both of them let us focus on one person to the exclusion of the other. That may sound selfish, but it wasn't. I mean, that's why I like spooning: it put me in the position of being in complete and total service to her pleasure. I wanted her to melt with pleasure. (As to why spooning beats cowgirl for that criteria, it's because there's less physical contact. If I can touch a girl with my whole body versus only with my cock, I'm definitely choosing the whole-body option.)

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