"As Told to" Sexual Histories: Alan

This is the first in a series of stories I'm writing based on the sexual histories of different men and women. These are true stories, based on what they have told me about their past. Alan first contacted me because he thought that my stories reminded him of his wife's infidelity. With his permission, I am retelling his story here. Although it's a fairly standard sexual history, there are a few unexpected twists and turns that are interesting. I've written it as if he were telling the story himself. If you are interested in having your story told, message me privately and we can discuss it. Just to let you know in advance, this story is not just about sex, so don't expect to be titillated from reading it. Everyone depicted in this story is eighteen years of age, or older.

I had my first girlfriend in high school after I turned eighteen, but we didn't get past mutual masturbation because she was very religious. But that didn't stop her from giving me hand jobs or from letting me finger her pussy, usually in the uncertain privacy of my car or her car. But that's as far as it went. I don't think I knew it then, but I really loved Alix, and if I had half a brain, I might have never broken up with her. But of course, I was an eighteen-year-old idiot who thought there were bigger and better things in store for me when I went off to college, so I ruthlessly broke her heart. I will never forgive myself for the thoughtless way in which I broke up with her.

Within two weeks of starting college, I had intercourse for the first time. Alison lived in my dorm, and she was considered the most attractive freshman there. There was a line of men who wanted to go out with her, but I got a lot of time with her because she seemed to like me. At first, I assumed that she considered me more as a platonic friend than boyfriend material. In fact, she told me all about the guys who had asked her out, as if I were firmly entrenched in the friend zone.

As an Asian American guy, I didn't think I had much of a chance with this blonde goddess. I was insecure about my looks, my race and, of course, the size of my cock. But Alison was so warm towards me from the minute we met, and seemed to be interested in everything I said. But at the same time, she was clearly looking at her options.

Option number one was a guy named Chip Wilson. Chip was a guy from a wealthy family who had gone to boarding school. Alison was unduly impressed by wealth and status, but aren't we all? I happened to be passing her room one evening just as Chip was leaving. I raised my eyebrows at her, and she motioned me into her room.

She was telling me all about the visit she had just had with Chip, and how she was mulling over his invitation to do something that weekend when I just leaned over and kissed her. I don't know exactly what I was thinking, but I think I didn't want to be the kind of guy who would stand for listening to a girl talking about another guy in that way. Surprisingly, she kissed me back, and, in a stunning turn of events, ended up giving me my first blowjob that night.

It happened so quickly. We were making out, first sitting on her bed, then rolling around. I hadn't even tried to get to second base when she started feeling for my erection, and then, the next thing I knew, she was undoing my jeans and taking my cock out. Considering how long it took me to get from kissing to feeling Alix's breasts, I was completely unprepared for how quickly Alison moved. Having your cock in a woman's mouth for the first time was a heavenly experience. That's the only way to describe it--it's like you died and went to heaven. Not having had a blowjob before, I came pretty quickly, and she swallowed it all. Especially since I hadn't expected it, the whole experience was mind-blowing to me.

Even more surprising, she asked me if I had a condom. You can imagine the disappointment I felt when I had to admit that I did not. But we ended up talking all night, and telling each other how attracted we were to each other, which is one of the nicest things at the beginning of a relationship, to hear about how someone likes you. Alison let me know that she had been frustrated by my failure to make a move earlier. I told her I had been crazy about her since the first day I saw her--I did not let on that I thought she was out of my league. She did clarify her condom question by saying that she was a virgin, and didn't feel like she was ready for sex, but that we could have anal sex. That also blew my mind, as anal sex had always seemed to me as several steps beyond regular vaginal intercourse.

Before she kicked me out of her room around two in the morning, she let me finger her and eat her out a little. My high school girlfriend had never let me do that, and I had no idea what I was doing, but Alison seemed excited by it anyway. As I left her room, she said, "I'm so glad you kissed me. No, 'glad' isn't the right word. I'm over the moon." I really think of this as my first sexual experience, and even though I didn't have a condom, it was perfect.

The next day, we had our first "date." I met her at the library around eight o'clock and we went out for ice cream and walked around campus. We went back to her room because she had a single, whereas I had a roommate. As promised, after making out, she offered me her back door. She was deathly afraid of getting pregnant and wanted me to put on a condom. I didn't have a problem with that...

I think that Alison had regular anal intercourse with her high school boyfriend, and didn't seem at all fazed by my cock going up her ass. Of course, my cock is on the smallish side, and it probably went in easier than previous visitors to the site. To this day, she had a much more stimulated response than any other woman that I've had anal sex with. I'm not sure if she had an orgasm, but it was a very enthusiastic response that anyone walking outside her door would have heard.

After I came, we were lying down in her twin bed, and I really felt again like I had died and gone to heaven. I imagine that's how most guys feel after the first time they've had sex, especially if you've done it with someone you're very taken with. But that wasn't the end. I don't think Alison set out to blow my mind two days in a row, but she did.

Afterwards, I remember admiring her naked body and thinking that it was the most beautiful thing that I had ever seen. I was content to lie there forever, just gently fondling her breasts and touching her belly. I remember Alison was playing with my limp cock, kneading it with her fingers and thumb as if she were an expert.

"I've changed my mind," she said.

"Oh?" I said, not having any clue about what she meant.

"I want to have sex with you," she said. "I mean, real sex."

"Now?" I said as any dumb guy would say.

"Now," she said, and she spread her legs, as if I needed the visual aid to help me understand what she meant.

I put on another condom, climbed on top of her, and pushed my cock inside her. I don't remember the details of our first vaginal intercourse. You would think that would be imprinted on your mind, but probably with my first experiences with oral and anal sex having happened just before that, my brain was too fried to record the event properly. I do recall that we had sex in the missionary position the whole time. I'm pretty sure she didn't come, although I probably lasted for a respectable length of time, since I had already come a little earlier.

What I do remember is that after I came, and I was lying on top of her, she said, "I love you." That came as a bit of a shock to me, and I said, "I love you, too." I think that having sex was so momentous for her that she didn't feel like it was right unless she loved me. Of course, the other thing I wonder now is whether it actually was her first time, or whether she wanted me to think she was a virgin. At the time I didn't question it, but in retrospect, she went so quickly from not wanting to have intercourse to deciding to do it that it's hard to believe she had never had vaginal intercourse before.

Alison and I had a great sex life that freshman year. We had sex almost every day. We were two eighteen-year-olds with healthy sex drives and we explored our mutual desires in a variety of ways. There wasn't a position that we didn't try. At the time, I didn't even know these positions had names. I thought we had made up some of them.

We tried bondage. Alison liked to be tied up and blindfolded. She had rape fantasies she wanted to play out. We even had some public sex. She gave me blowjobs in the dorm stairwell. We had sex in the library restroom. For someone who was afraid of getting pregnant, she also had a weird thing about flirting with it. One time, before she went on the pill, she asked me to take off the condom and fuck her without a condom. I initially resisted, but gave in, and took off the condom. It felt great to be in her pussy without the condom.

The plan was for me to just do it for a bit and then put the condom back on, but then she insisted on me coming inside her. Of course, I didn't do that, and pulled out. She expressed disappointment, but was probably relieved, too. After the next time she wanted me to do it, I told her she had to go on the pill.

I remember many nights when we would have sex for hours, and I would come three or four times. I think my record was six or seven.

The sex was great, but we didn't work on other aspects of our relationship. We were only eighteen, so what did we know? We didn't fight, although she would get unreasonably jealous when I talked to other girls.

The first sign of trouble was spring break. I didn't have any plans but to return home for the week. Alison wanted to go down south for spring break with a bunch of her friends. I really couldn't afford that, and since it seemed like a nice thing for her to do with her friends, I didn't try to figure out how I might be able to go along.

A week before spring break, she told me that she and her friends were going to be staying in a house with a bunch of guys, including Chip Wilson, the guy who had been interested in her. I tried to seem nonchalant about it. I really wasn't insecure about my relationship with Alison, and wasn't too bothered by her being around other guys.

After spring break, Alison told me that Chip had come on to her, and made it clear he was still interested in her. I found the idea of her having sex with Chip to be arousing, and I remember thinking about it a couple of times when we had sex.

That summer, I visited Alison and her family at their beach house. The visit was a disaster. It was clear that her parents didn't approve of me. I was not only Asian American, but I came from a working class family. My dad worked at the post office, and my mom was a clerk at a department store. Her father was a partner at a large law firm, but in addition to that, they had a lot of family wealth. As much as Alison and I got along so well at school, in the context of her family, we seemed like an awkward match.

Shortly after that visit, Alison broke up with me. It was, up to that point, the most devastating thing that had happened to me. It didn't just break my heart, I think it broke me, and it took me a while to get over it.

My sophomore year was a bit of a blur. I couldn't bring myself to ask anyone out for a long time. My rebound girlfriend probably says a lot about me. I had a friend, Becky, who had lived next door to me freshman year. I knew she had been interested in me since freshman year. One night in January, we had gone out and had too much to drink and ended up in her bed together. The sex was unmemorable, or maybe it's more accurate to say it was memorable in how awful it was.

The thing about Becky was that she was as different from Alison as you can be. She was Jewish, overweight and depressed. She wasn't ugly, but on the unattractive side of being a plain Jane. But on top of that, she was kind of an awful person. I think I was feeling so bad about myself that I thought that was the best that I could do at that point. And I was horny. So rather than leaving our drunken encounter as a one-time mistake, I embarked on a relationship with Becky.

No one liked Becky. Even Alison was alarmed when I started going out with Becky. I remember having an awkward conversation with her in which she seemed to be telling me I should stay away from Becky. Alison, meanwhile, was dating some amazingly handsome blonde guy who seemed like a surfer dude. It really sucked, and it was terrible to have an ex-girlfriend not be jealous of your new girlfriend because everyone knew she was fat and awful. It really was the low point in my life.

Becky was more obsessed with Alison than I was. She was really into the fact that she was going out with Alison's old boyfriend, as if that conferred some kind of status on her. She would bring up Alison during sex. She would ask me if Alison was as good as she was in bed. As insecure as Becky was about her appearance, she seemed to think that she was a rock star in bed, which she was not.

Becky also liked sex very rough, which I thought was surprising for someone who had been a virgin before we had sex. She liked to have her nipples pinched hard, and even wanted me to pull her hair and choke her during sex. I actually got into abusing her, and started fucking her up the ass because she seemed to think that it was especially nasty. But she also got into that as well, and she used to say while we had anal sex, "I bet Alison never let you fuck her up the ass, did she?"

But soon, I couldn't even get hard for Becky, which was something I had never experienced before. She would have to suck me to get me hard, and then, during intercourse, I would sometimes lose my erection. Something about the way she made love--the things she would say or the sounds she would make would just turn me off. I hate to admit it, but the only thing that could turn me on about having sex with her was when she wanted me to abuse her. I worried that I had a sadistic streak, but after Becky, those feelings have never surfaced again.

On top of that, Becky and I would argue all the time about the stupidest things. She was a tiring person to be around. I think she might have been narcissistic or suffered from some personality disorder. And she was very possessive, and insisted on doing everything with me. There was another female friend, Jessica, that I had gone to high school with, that I would sometimes have dinner or lunch with, and Becky hated her for some reason. Jessica was not interested in me as a potential boyfriend, and was about as non-threatening as a person could be, but Becky put her on the persona non grata list, and told me she didn't want me to see her, or she would be very angry.

I didn't take Becky's threats seriously because they were absurd. I had been friends with Jessica since I was ten years old, and she had a boyfriend, and I didn't see any problem with being friends with her. One night, I had dinner with Jessica, and then went to a movie with her. It wasn't that I was trying to be secretive, but I didn't tell Becky about it in advance.

The next day, somehow Becky found out about my evening with Jessica, and came over, all bent out of shape. I was in my room with my friend Matt, and Becky let me have it right in front of him.

"I told you I didn't want you to see Jessica!" she roared at me.

I don't remember everything she said in her speech, but she ended up telling me that "we were done." I don't think I said a word. As she left, I got up to go after her, and my friend grabbed me, and kept me from going.

"Yo, dude," he said. "You just got a gift from heaven."

He gave me a high five. Like other friends, Matt had been encouraging me to break up with her. And that really was the end. I'm not sure I ever saw her again. I heard she never married. Alison also never married. She became a very successful investment banker on Wall Street, but didn't find the right guy, I suppose. A mutual friend told me once that Alison told her she regretted breaking up with me, but I don't know if she really felt that way.

I spent my entire junior year without a girlfriend. I was almost celibate, except for two one-nighters I had. It was a stark contrast to my freshman year with Alison. I didn't know if I would ever have that again.

At the beginning of my senior year, I developed a crush on a woman in one of my classes, Charlotte Lambert, but I couldn't even figure out how to talk to her. It wasn't that she was beautiful in a standard way, but there was something about her that was dazzling. She was smart, clever and kind. I spent most of the year just pining after her. It was as if I had reverted to being back in middle school.

I also met Nina Lee, an Asian American woman. She seemed very interested in me, and we started spending a lot of time together. We would play tennis, and have meals together. After a couple of months, she made it clear that she wanted to be more than friends, but I kept her at bay because of my crush on Charlotte.

Things continued this way for a long time. I kept planning to talk to Charlotte, but wouldn't. I also wanted to resolve things with Nina, one way or another, but didn't. As much as I wanted to have sex with Nina, who seemed very willing, I didn't because I didn't think it was right for me to start a relationship with her when I was in love with someone else. I really thought that I was passionately in love with Charlotte, a person I didn't even know. Someone should have told me that having an adolescent crush is not the same as being in love.

Of course, I didn't tell Nina about my crush on Charlotte, and she was generally content with spending time with me. She seemed pretty confident that I would eventually come around. In fact, Nina was considered quite attractive, and my friends thought I was crazy for not pursuing her.

One night during spring semester, things finally came to a head. Nina told me she didn't want to wait for me any longer. She said she didn't understand what was going on with me. Other men were interested in her, why wasn't I? I couldn't really answer that. I asked her for a week.

I finally got my courage up and talked to Charlotte. We went out for coffee. She turned out to be a complete disappointment. We had little in common and my image of her had been shattered. At least I felt that my path was obvious now.

But it was too late. Even though a week hadn't passed, Nina had already started going out with another guy. So I spent the last two years of college without a girlfriend. After a spectacular start, my sex life had completely fizzled out by age twenty-two. Along with breaking up with Alix, losing Nina is one of my biggest regrets. I was too foolish to see what a wonderful opportunity was right in front of me.

After I left college, I vowed to change the way I engaged with women. I realized that I was way too passive, and that I had to be more proactive. I also wanted to stop being attracted to women based on how they looked. I also decided, after having let Nina slip through my grasp that I had to stop being a self-loathing Asian American, and be open to dating Asian women. I think that my reluctance about going out with Nina had a lot to do with the fact that she was Asian, and I was, for whatever reason, fixated on Charlotte because she was white.

I realized that Alison's parents' rejection of me had to do, in part, with the fact that I wasn't white. Even Becky would say from time to time that she wished I were Jewish. It seemed to me that the easiest way to take my race out of the equation was to date Asian women.

But of course, the next woman I went out with was a fellow first-year law student named Holly. She was blonde and athletic and fun to be around. The only problem was that she had a serious boyfriend. Holly had gone to Boston College, and her boyfriend, who was a football player, had stayed on as a graduate assistant for the football team while he tried to figure out what he wanted to do.