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.
I was attracted to Holly from the start. I didn’t know what to do with the fact that she had a serious boyfriend, so I just ignored it. One day as we were leaving class, she asked me if I wanted to go for a run. We ran down the Westside Highway. She looked great in shorts and a tank top. When we had run about two miles, we stopped and walked for a while. I don’t know what it was about the moment, but we were just looking at each other, and then the next moment we were kissing. I don’t even remember who made the first move. It was spontaneous and almost magical. We ran back to her apartment very quickly, and when we got inside, she unceremoniously stripped off her clothes, and kissed me again. We maneuvered ourselves over to her bed. I told her I didn’t have a condom, and she just said, “Shh–it’s okay.” She was really wet, and I just slipped my cock into her, and we made love until it got dark.
Holly and I slept together two or three nights a week, and every other weekend, she would go up to Boston to see her boyfriend, or he would come down to New York to see her. On some weekends, they wouldn’t see each other. Their schedule was complicated by the fact that it was football season and there was a game every Saturday.
Our sex life was good, but conventional. She did a few things that were new to me. For example, she would often stop in the middle of intercourse to suck my cock. It helped to extend how long I could go without coming. Whenever she sensed I might be getting close to coming, she would stop and suck hard on my cock, and somehow that would have the effect of preventing me from coming for a while. It was also very sexy.
She also liked having me come on her face or body, although that might have been partly because she didn’t like swallowing cum. She said it wasn’t the taste, but the consistency she didn’t care for. The couple of times she let me come in her mouth, she spit it out. She was also one of the few women who liked being on top. We did have anal sex a couple of times, but she said she had never done that with anyone else. I assume that meant her boyfriend, as well.
We never talked about her boyfriend, during sex or otherwise. I didn’t really want to know about him, especially knowing that he was a football player. Unless he was the kicker, he was most likely much bigger than me. I did see him once when he was visiting, from afar. I was surprised that I didn’t feel much jealousy toward him.
After a couple of months, I thought there was an opportunity to ask her to make a choice, and I believed that she might have chosen me. But I decided I was content to leave things as they were. It was perfect for my noncommittal mindset. I was having great sex with a beautiful woman, but I didn’t have to worry about whether she was the right one for me.
In trying to decide whether Holly was right for me, I was put off by her bad taste in music as well as her lack of interest in reading. But mainly, I was bothered by the ease with which she cheated, and how she integrated two men into her life without thinking too much about it. I probably shouldn’t have judged her too harshly about that. I know now that love is complicated and a lot of times you just roll with what comes your way.
Things changed after our grades came out after first semester exams. Holly did spectacularly, and my grades were mediocre. My poor performance somehow changed her ideas about me, I think. It was like she was disappointed in me. Holly applied to transfer to Harvard, and was accepted, and broke it off with me. I think I half expected it, and it wasn’t the heartbreak I experienced when Alison broke up with me.
I had a friend who cruised undergraduate parties at different schools in the city, and he badgered me to go to several with him. He was spectacularly successful with women, and always met someone to sleep with at these parties. I wasn’t as lucky. Part of it was that I just couldn’t get into the idea of going out with someone who was still in college, even though they were only a year or two younger than me.
In other words, I was a complete dweeb. But one night, we went to a party at NYU, and I met a Chinese American woman with an amazing body. I couldn’t take my eyes off her, and she must have noticed because she came up to me and introduced herself. Amy was smart, and sweet, and she took me to her apartment and fucked me. She had a tiny room in an apartment she shared with two other women. After we used the two condoms I had, she told me to go to the pharmacy to get more. We fucked all night, and I didn’t leave until morning.
Amy was in the process of breaking up with her boyfriend, it turned out, and I thought that maybe I was just the one-time rebound guy. But we saw each other four or five times a week during the next two months as she extricated herself from her relationship. It felt weird to be “the other guy” for the second time. I know there were even a couple of times when Amy had sex with her boyfriend during that time. But I was willing to wait things out.
Eventually, they officially broke up. Things didn’t change between us, and I always wondered if it would have been better for us if I had just waited until she had completely broken things off before I started a relationship with Amy.
I always thought of Amy as being inexperienced, but that wasn’t really the case. She had slept with more people than I had. I had a total of four women on my list before I met Amy. She had slept with at least twice as many partners as I had, although I didn’t ever know for sure because she was so reluctant to talk about it.
We dated for a year, and then she moved into my apartment in my third year of law school after she had finished college, over her parents’ objections. We were married after I finished taking the bar exam.
Things went terribly wrong after we were married for one year. And that’s kind of an understatement.
I went out of town for a weekend to take some meaningless depositions, the kind of things law firms let junior associates do to get their feet wet. But I finished a day early, and flew back home on Saturday instead of Sunday. I didn’t call Amy because we didn’t have cell phones then, and I thought I would just surprise her.
I ended up being the one surprised when I opened the apartment door to see Amy being fucked violently by a strange man. She was draped over the arm of our sofa, and he was ramming her from behind. My first thought was that she was being raped. Amy saw me first, and her eyes went wide in shock. She didn’t say anything, but gestured to the man to stop. Instead, he just smirked and kept pounding her. He was looking me in the eye, maybe daring me to stop him, but I just stood there. Later, I wondered if I should have pulled him off of my wife, or punched him. I felt emasculated by my inaction, although I suppose the emasculation had already occurred.
Amy also didn’t seem to try to get away from him, either. Suddenly, she cried out, “Oh my god, yes, oh my fucking god!” The guy was then coming inside her, just slowly slamming his dick inside her for the final few times before pulling out. Then I saw how big his cock was. In my memory, it’s probably bigger than it actually was, but it was certainly much bigger than my cock. The whole scene was surreal. I also noticed that he wasn’t using a condom.
Then, as he stood there naked, with his dick just hanging there and without any kind of embarrassment or shame, he said to me: “You the husband?”
I nodded, and he said to Amy, “You fucking bitch, you said he wasn’t going to be here.”
Then he got dressed, and before he left, he said to me: “Sorry, man, no hard feelings, okay?”
I just stared at my naked wife in disbelief. I mean, we had only been married for a year. I didn’t think she was capable of anything like this. I had no way of processing what had happened. If I hadn’t seen it with my own eyes, I wouldn’t have believed it if Amy had confessed to me.
Amy went into the bedroom to get dressed. After a while, when she hadn’t come out, I went into the bedroom, and she was sitting on the bed.
“What’s going on?” I asked. “Who was that guy?”
“His name’s Paul,” she said. “I met him six months ago.”
Six months ago? And I thought we were still in the honeymoon phase of our marriage.
“So, are you in love with him?” was my next question.
“I don’t know,” she said.
“Are you leaving me?” I asked.
“No, of course not,” she said.
“Then what’s going on?” I aked.
“I don’t know,” she said. “I don’t want to talk about it.”
I said that we had to talk about it, that I needed to know what was going on. I think she knew she had no choice, and started to tell me what was happening. She had been introduced to Paul through someone at work when a group of colleagues were having a drink after work. When everyone else left, she and Paul were there alone at the bar. Paul suggested that they go somewhere, and she knew what he meant by that, and she thought it was outrageous that he would propose such a thing, but she went anyway.
They drove to a motel, where they had sex. Like most men, I wanted to hear details about the sex. It probably would have been better if I never heard what happened. But what they did didn’t sound like sex, it sounded more like she was brutalized by him. Her description of what they did left me shaken.
I am still surprised that she told me what he did to her. I wondered if she enjoyed torturing me with the details. He routinely fucked her up the ass and fisted her pussy. He would even fist her ass. They didn’t use a condom, and he didn’t clean himself after being in her ass and before putting his cock in her pussy. She would even suck his dick after it had been in her ass.
They had sex regularly. They would see each other two or three times a week. She usually met him at a hotel or a motel. She went to his house once or twice. He had a long-term girlfriend that he lived with. They had had sex at our apartment a few times. They met during lunch time, or after work. She let him come inside her even though she wasn’t on the pill.
I hate to be overly dramatic, but I really felt at that point like I would never be happy again. I had thought that no one could hurt me as Alison had, but this was pain on a different level. When Alison broke up with me, I cried. This time, I didn’t cry because I was too numb. It was way too much for me to even process. In the end, I just tried not to think about it.
These revelations put me into a kind of shock. I could hardly believe what I was hearing. I couldn’t believe that my wife–or anybody–would engage in this kind of behavior. But it also provided an explanation for some things that I had been unhappy about. Our sex life had really dropped off after we were married, and I was unhappy about that. I thought that perhaps Amy suffered from having a low sex drive. Now I realized that Amy did like sex, but had been too busy to have the energy to have sex with two people. Or maybe she just didn’t enjoy sex with me.
But I was also optimistic that we could save our marriage, and that our sex life might actually improve. I thought that her misbehavior would put me into the driver’s seat as far as our sex life was concerned. I thought that she would be eager to make it up to me, and be grateful that I wasn’t going to leave her. But that turned out to be wrong. After my discovery of her affair, I wanted her even more, but she seemed to lose even more interest in having sex with me.
I gave her time, reasoning that she would need time to get over this confusing time, and to reorient herself. But three months later, as I was walking to have lunch with a friend, I saw Amy in a car with Paul. Later that day, she admitted that she was still meeting Paul for sex, once or twice a week. I think I was just starting to feel normal again, and this put me into another emotional tailspin.
I couldn’t figure out what was going on, and why. I blamed myself for Amy’s behavior. I thought about our sex life, and decided that I probably hadn’t been enough for her. Like most men, I jumped to the conclusion that Amy preferred men with huge cocks. I had seen Paul’s penis, and there was no comparison.
I really should have left her then, but I felt that losing my wife would be too humiliating. Fixing my marriage seemed like the more manly thing to do. So that’s what I tried to do. Amy said her relationship with Paul was over. I believed her this time. Her unexpected absences stopped. She stopped working late. We resumed our sex life, although she didn’t seem that excited about it, or want to have sex all that often. Given what had happened when I first met her, I couldn’t help but think that maybe I was being phased out.
But I still wanted her, sexually. If anything, I wanted her even more than I ever had. But there was a twist to my desire for her: Every time we had sex, I imagined her having sex with Paul. Well, I didn’t have to imagine it, because I had seen it. But I would think about it, and it would make me hard, and when I thought about it while fucking Amy, it would make the sex so intense, more intense than I had ever felt. I would tell Amy about it, but she wasn’t interested in participating in my fantasies about her.
I would think about how Paul fucked her so hard, like nothing I’d ever seen before. I would think about his huge cock going in and out of her pussy. And I would think about how hard she came, even with me standing there in front of her, yelling, “Oh my god, oh my fucking god!”
Then I noticed that Amy liked talking about different men from time to time. It was almost like she would get a crush on a guy at her office from time to time, and couldn’t stop talking about him. I realized that she had always done this, but I hadn’t seen it for what it was, her roving eye, an attraction to different men. And then I would fantasize about her fucking her latest crush.
Still, Amy had no interest in taking part in my cuckolding scenarios. I would ask her: “Do you want to have sex with Don? Do you think he has a big cock?” But she just didn’t want to play. After a while, I asked her, practically begged her, to pretend that she had already had sex with different men she knew, but she refused. She acted shocked that I would ask such a thing. At one point, I desperately wanted her to have sex with someone else, as long as she would talk to me about it afterwards. Of course, this was not something I could even discuss with her.
Amy instead acted as if her affair never happened. All she wanted to talk about was having a baby. I wasn’t ready for that, given what had happened, but she had no trouble with it.
In some ways, my relationship with Amy was just a replay of my relationship with Alison. Even though we were both Chinese American, my family wasn’t as well-educated or wealthy as Amy’s. Amy’s parents were from well-to-do families who had immigrated to the U.S. to escape the Communists. My family was Cantonese, and although we had come to the US several generations ago, we hadn’t gotten very far. It was kind of comical: my father’s family had a Chinese restaurant, and my mother’s family had a laundry somewhere in their past.
I suspected that Amy felt superior to me because of our backgrounds. Her family was wealthier, and all of her siblings were successful. Amy’s mother was a doctor and her father had a successful business. My father was a postal worker and my mother worked part time as a retail clerk. I was moderately successful, but my brother worked as a longshoreman, and my sister worked at the Costco.
I don’t know how the differences between us played a role in her cheating, but I feel that it must have been a factor. I would love to talk to Amy about it, but she hasn’t been open to talking about it, even now, years later.
It was sometime after this that I met Laurie. Laurie was a lawyer at another firm. I met her working on a case where her firm and my firm represented co-defendants in a securities and banking fraud case. My firm’s client had only minor exposure in the case, and we expected to be out of the case at some point, so the firm had no trouble sending a junior associate to meetings on the case.
Laurie was a senior associate, about six years older than me. She was married, and had a three-year-old son. Laurie was gorgeous, the kind of woman that men stare at. She made Alison seem like a plain Jane. She could have easily passed as a supermodel. She was 5 foot 8, with an unbelievable body, although I didn’t really appreciate her body at first. I was mesmerized by her beautiful face.
It was kind of love at first sight for both of us. After the meeting, when the other lawyers had left, we sat and talked in her office for an hour or so. The second meeting was held at the offices of another firm. After the meeting, the two of us stayed in the conference room and talked for what must have been two hours. At some point, someone came in and asked us to leave. I walked her back to her office as if I were a middle schooler walking a girl home from school.
After the third meeting, she asked me if I wanted to get a drink afterwards. If she hadn’t asked first, I was going to. I don’t know why I felt so at ease around her, but it just felt as if we were meant to be together. That first drink was the most romantic moment of my life. Of course, we just talked, but the sexual tension was palpable. Many times I almost reached out to touch her hand, but I didn’t. We talked for hours, and I was shocked when I looked at my watch and saw that it was almost ten o’clock. Being lawyers, we both had spouses that were used to us working late, but I still felt quite guilty as I drove home.
The next day, Laurie called me at the office. We hadn’t been talking very long when she suggested that we meet at a hotel. I couldn’t believe that she would just come out and say it. Of course, I said yes. She told me to get a room tomorrow at this hotel that was downtown, a pretty nice one, and to call her with the room number.
The next day, I went to the hotel at lunch time, got a room, and called Laurie with the information. I could barely work the rest of the afternoon because I kept thinking about being with her. We had agreed to meet at six, but I couldn’t wait any longer, and went to the hotel at 5:30. I had kind of hoped to find her there in the lobby waiting for me, but she wasn’t.
Going early turned out to be kind of a mistake. An hour later, Laurie still wasn’t there. If I had gotten there at the right time, she would only be half an hour late, I tried to tell myself, but having been there for an hour made me anxious and irritable. To make matters worse, I kept getting undressed and then putting my clothes back on.
When it was seven, and she was officially an hour late, I seriously considered leaving and gong home. I tried calling her office, but she wasn’t picking up her phone. But a few minutes after seven, there was a knock on the door, and she was at the door. All the annoyance that had built up inside me just melted away in an instant. She took my face in her hands and kissed me passionately.
She took my shirt off, and admired my body, which shocked me. I had been feeling bad about myself since Amy’s infidelity, and didn’t think of myself as being physically desirable. But I worked out regularly and was in good shape. I had just stopped thinking of myself that way.
The sight of Laurie’s naked body was a bigger shock. As beautiful as she was with her clothes on, I could not have imagined how perfect her body was. She had perfectly sized breasts that were firm and nicely shaped. Her belly was completely flat, even though she claimed that she didn’t have time for the gym. What I had never realized before because I had always seen her in skirts and dresses was that she had a flawless ass–soft, but exquisitely shaped, like a Roman statue. She could have easily been a swimsuit model.
We had wild, primal sex that day. We only had a couple of hours, but it felt like we did everything. But let me start from the beginning. When she touched me, her bare hands on my bare skin, it was shocking. I had never felt that way with anyone before. Her touch was magical–it seemed to awaken all of my senses. When she touched my cock, I almost jumped from the way it felt.
When I looked at my cock in her hand, it didn’t even seem familiar. I almost came as soon as she put it into her mouth. I had to pull away from her because I didn’t want to come so quickly.
“Don’t pull away,” she said.
I told her I was afraid of coming too soon.
“There’s no such thing,” she said. “Come, if you want to, it won’t be the only time you come today.”
She put my cock back in her mouth, and she made me come. I hadn’t had sex for a few days, and there was a lot of cum, and she swallowed it all. I was a bit chagrined about coming so quickly, but something about the way Laurie acted made me get over it pretty quickly. As I went down to her pussy to return the favor, she took hold of my head to stop me. She told me that she had been having incontinence issues since she gave birth, and that her husband said that she smelled bad.
I told her it was okay, and I started working on her labia, licking all around her pussy. There was a faint odor of urine, but after a while, it was gone. I put my tongue into her pussy, and I could tell it was already wet with her juices. Then I started on her clit, and she grabbed me by the back of my head to keep it there. Whenever she got excited, she pressed my face into her.
Although I had just come, hearing Laurie’s arousal had me hard again. It didn’t take long before she climaxed. It felt so satisfying to hear a woman come so hard. I don’t know if I’d ever heard Amy come like that.
“It’s been a long time since anyone’s done that,” Laurie said. I realized that it had been a while since I had eaten someone’s pussy. Amy didn’t care for oral sex, at least not with me, and I think the last time I had regularly administered oral sex was years ago, with Alison.
Laurie noticed that I was hard, and pulled me on top of her. I reached for a condom that I had placed on the nightstand, and she told me I didn’t need to put one on. Entering her pussy for the first time was something I will never forget. She was so wet and velvety, and she shuddered as I pushed myself in. She wrapped her legs around me, and urged me on, pulling on my hips as I started to rhythmically push in and out of her.
I don’t think I’d ever seen a woman so into sex as Laurie was. It was clear she found it to be very pleasurable. I’m not sure Amy ever saw sex as pure pleasure. After a few minutes, Laurie stopped me, and pulled her legs up against her chest. She was the most flexible woman I had ever seen. I didn’t even know a person’s legs could so easily go up against their chest like that.
“Fuck me hard,” she said, as we started again. “Yeah, just like that.”
I had just started to slam myself into her when she suddenly came. Her orgasm seemed to go on and on, and then she was making strange noises. I couldn’t tell at first what was happening, but then I realized she was sobbing. I stopped, and held her until she stopped crying.
“I’m sorry,” she said, wiping her tears. “Sometimes when I come, it makes me cry. I think it’s the release of emotions.”
“Are you alright?” I asked.
“Yes, I’m fine,” she said. “Don’t worry, you made me very happy.”
After a little while, I was hard again, and Laurie asked me if I wanted to fuck her up the ass. She produced some lubricant, and I was excited to find that Laurie like Alison, was completely into anal sex.
When we finished, Amy called room service for a bottle of champagne. I didn’t have much money then, and thinking about having to pay for the room and champagne caused me a lot of anxiety. We made love for a fourth time that evening before she had to rush off to be with her family.
We started seeing each other regularly. There was no way I could afford to pay for a hotel room even once a week. Fortunately, Laurie had a key to her sister’s apartment nearby, and we met there often. But Laurie was used to nice things, and often wanted to go to a nice hotel. She and her husband had a lot of money, and she had no trouble paying for it.
Although the relationship had started off as something purely physical, I came to appreciate her as I got to know her. She thought her husband might be a bit autistic. He had an explosive temper, and he scared her. Their child was difficult, which made the marriage harder.
I initially hadn’t planned on telling her about Amy’s cheating. I thought it would make me seem like a loser. But I told her, and she was very sympathetic, and she said it helped assuage some guilt she had about Amy. But when she found out Amy had been having sex with another man, she thought we should use condoms. I was happy to agree because I had also learned that although I was the first man she had slept with since she had been married, Laurie had slept with dozens of men in the past.
In many ways, I feel like Laurie saved my life. She made me feel wanted and masculine, and much less like a loser. The good thing about being with an experienced lover is that you feel like you’ve accomplished something by pleasing them. Of course, the reality is that Laurie just knew how to enjoy sex, and what she needed to do to have an orgasm.
One night, after I had been seeing Laurie for about six months, I came home to find Amy upset and in tears. I had just had sex Laurie, and I jumped to the conclusion that Amy had figured out that I was sleeping with someone else.
“What’s wrong?” I asked.
“My life is completely screwed up,” Amy said through her tears.
“Why?” I asked, putting my arm around her tentatively, not knowing if she was going to strike out at me.
“I’m pregnant!” she sobbed.
We had stopped using birth control because Amy wanted to have a baby. I was still unsure about it, but my affair with Laurie made me feel like I didn’t have the moral authority to deny her. Still, I wasn’t sure how successful we would be when I was having sex with Laurie two or three times a week.
“Isn’t that good news?” I asked. In reality, I was somewhat panicked by the news because I was starting to fall in love with Laurie, and I think Laurie felt the same way about me.
Amy put her head down and started to cry harder.
“What’s wrong?” I asked her. “Are you sure you’re pregnant?”
“Yes, I’m sure,” she said. “But I don’t know whose baby it is!”
It turned out that she had been sleeping with her supervisor at work, Sam. Just as with Paul, they had been having unprotected intercourse.
I told her things were going to be fine. I don’t know why I said that. This was a sign from the universe, my opportunity to escape from Amy, once and for all, but I didn’t see it that way. First of all, there was at least a fifty-fifty chance the baby was mine. Second, it felt like the right thing to do. I told her I would stay with her, whether the baby was mine or not. I don’t know why, but it felt like the gallant thing to do. I knew she didn’t deserve it, but it made me feel better to be the bigger person about it.
I told her we could get a DNA test at some point, and that it would put her mind at ease. I told her that knowing one way or another would make her feel better. I asked her if she wanted to leave me for Sam if the baby was Sam’s. She said Sam was married with three kids, and that he would never leave his wife, that she was nothing but a cheap Asian slut to him.
“But you didn’t answer my question,” I said. “Do you want to be with Sam, if you could?”
“No,” she said. “I don’t even like him that much.”
“It’ll be perfect,” I said. “We’ll have a baby, but Sam will have to pay for it!”
That made her laugh. We talked honestly for the first time since I had discovered her and Paul. She apologized for the first time. It felt surprisingly good to hear it. She said she loved me, and that she was just a screwed up person.
When I told Laurie what had happened, she became very angry. She told me that I should have told her that Amy and I were trying to get pregnant. She said she loved me, and that she had been hoping that we could be together. She didn’t tell me that I should leave Amy, although she said that Amy didn’t deserve me. We had never had a fight before, and it was very painful. We didn’t break up then, but our relationship didn’t last much longer after that.
Amy had a DNA test mid-pregnancy, and it turned out the baby was mine. Amy seemed very happy and relieved by the news. I wonder what I would have done if it was Sam’s. Would I have kept my word, or would I have left her for Laurie? Either way, I would have ended up raising someone else’s child.
So is everything okay now? I don’t know. I think Amy is kind of a screwed up person, like she says. Our sex life is still not satisfying for me, but I know I still want her, and that’s something. And I love our daughter more than anything in the world, and that’s something, too.