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Warning: May contain graphic descriptions of sexual encounters.
Gloria
What a crappy launch to a sex life at the start of my junior year of high school. At a small party at which she was the only girl, Gloria, a senior, stripped down to her panties to go swimming in the backyard pool. Our high school eyes were bulging out of our skulls. Later, I came across still mostly naked Gloria and my best buddy snogging on the living room couch. I said “sorry” and started to leave. Somehow, the three of us ended up in an upstairs bedroom. I was going down on her while my friend was kissing her and playing with her lovely breasts.
Then, without asking or using protection (although I think she had made it clear that was what the trip upstairs was for), I started having sex with her. My first thought was “this feels so great, why isn’t everyone doing this all the time?” But after about 10 minutes, I got too vigorous, and fell out. She pushed me off, saying I was done, and grabbed my friend. After, we all got dressed. I drove her home, and tried to have sex again at my favorite makeout spot. But she defeated me with tears and an unbelievably sad story of a gang rape she had endured a month before. I am shocked at what a jerk I was at 16.
Wanda
Another senior a few weeks later at another party. I barely knew her, but we ended up making out in the dark, and then I walked her out to her car. It was very late now, about 4 in the morning, and no one was about. We had sex up against the side of her car but only for a few minutes. I didn’t finish. She got behind the wheel, put my penis in her mouth as a strange goodbye, and then drove off.
Monique
Another senior, she and I had been hooking up off and on for years by the time we decided to have sex. Or, I should be clear, she decided. But she was then a very sincere Catholic, very pro-life, and didn’t believe that she could trust birth control to avoid pregnancy. So she suggested we have anal sex. Having devoured my father’s pornography featuring anal sex for years, I was entirely up for it. On her parents’ double bed, it was incredible how hot the experience was. She came, then I did. We did the same a few weeks later, just a couple days before she left for Princeton. For years, this was my goto memory for masturbating. Years later (decades, really) when I told her that, she glowed with pride.
Oma
She was so beautiful, just 17 at the start of college, half Bangladeshi, half Nepalese, and we were into each other from the start. My first really serious committed relationship, I could not have asked for a better lover, friend, and companion. She was a virgin, yet had one of the strongest sex drives I’ve known.
Rachel
I had a crush on Rachel for years, going back to 8th grade. She was three years older than me, and a complete blonde goddess. Not only was she not in my league, I wasn’t even sure she was from my planet. I gradually got onto her romance radar (taking her to see the Police/REM show didn’t hurt). So we had a great date the night before my family went to Italy, a date that took us to the brink of sex. Arrived back from Italy, I hadn’t slept in 40 hours, but the whole time I had been thinking about Rachel. She begged me to come over, I asked to wait one day, she pointed out that she would only have the apartment to herself tonight…I came over. We hooked up, we started having sex, she mentioned that being on top was her favorite position, so we switched positions…and I lost my erection. This had never happened to me before. The jet lag? The beer we had sipped? Whatever. There is something about bad sex, and we never had it again.
Kathy
She was also at the same college. She was taller than me, and also very into penis sizes, which I knew long before I hooked up with her. I had some dumb idea that Oma couldn’t validate me because she was a virgin, whereas if the size queen enjoyed sex with me, I must be awesome. She knew I had a girlfriend, but she herself was hopelessly in love with a gay guy, so it seemed alright to hook up that summer. We hooked up a total of 3 times, and she wrote me a detailed erotic account of it, in the form of a confessional “dear diary” which turned me on so much that I kept it, which was what my snooping girlfriend found. She destroyed my computer as revenge.
Laurel
We were camp counselors together the summer of my junior year. We had mediocre sex in a bathtub.
Kristen
She was a friend of my college ex-girlfriend, and the ex-girlfriend of my former bandmate. So even though we were both broken up, this was a really bad idea. It was just one night, in her parents’ basement, where I was staying while in town to get a visa. She was surprisingly kinky, very much a sub. We swore each other to secrecy, but she broke under stern questioning. When the two exes found out — explosions.
Darleen
I doubt that was her real name. By now, I was post college, living in China, teaching economics and English. I met this Thai girl at a bar, we exchanged numbers, I called her, we had a date, came back to my group house, watched a terrible Mel Gibson movie involving an elephant (her choice), and had sex (my choice, probably). The sex as just meh, we got interrupted by my 50ish house mother (we were in the common room), and I’m pretty sure a blowjob from her is how I got herpes. For obvious reasons, this is the sex I most regret.
Zhin
She was one of my students, already active in the business world for a major Chinese company. I waited until after the class was over and asked her out. The language barrier was huge—her English was atrocious, and my Chinese probably worse. But it turns out this was one of the great sexual connections of my life. She was really vanilla until she met me, but willing to try anything—spanking, outdoors, anal, getting tied up, sharing fantasies. We met up again in 1996 when she visited me in the US, back in China in 1999, 2000, and then in 2007, even though she was married with kids.
Zhin 2
It’s not a common name, but I had another student with the same name in the next class, and she also was sending me subtle hints. She was much more beautiful than Zhin 1, younger, but somehow, we didn’t click as well.
Penny
She was in my graduate business program, back in the States. She had been raised a strict Catholic, but was losing her faith. She had had sex only once, incompletely, before, in a moment shrouded in guilt. She was also messed up about sex generally because of sexual abuse from ages 5-7 at the hands of her grandfather. We dated for about 8 months. We went incredibly slow, by my standards, in waiting a few months before having sex. By her standards, we were rocketing down the highway. We ended up having sex on the 3rd story rooftop balcony of the place I lived at, in daytime, not noticing until we were done the 11 story office building three blocks away that overlooked our outdoor lust. She is one of those women that looked better and better after I broke up with her, not just in terms of looks but in terms of how I felt about her and the relationship.
Niu
Another Chinese woman, although this time we met in the States. Niu was among the most beautiful women I’d ever seen. We went out for about 7 months. The relationship had an interesting financial dynamic, since I was living on my stipend, and her family back in Taiwan was incredibly rich. At spring break, she wanted to go on vacation—I said, great, there’s a state park a few hours drive away. And she said—I was thinking about Barbados. She was also the first woman I’d ever been with who didn’t have any breasts at all. It didn’t stop her from being one of the sexiest women I’ve ever been with, but I could tell she was a little uptight about it.
Tia
She was another friend of my college ex-girlfriend. And we ended up living in the same town, and she came on to me after a night out years after we graduated. The sex was…blah. And it was clear that she wanted a relationship, but I didn’t.
Felicity
She had a crush on me in college, and it was so obvious that my then-girlfriend mocked her mercilessly behind her back about it. I was never attracted to her, but she was a good friend, and so we hung out. We met up again in NYC a few years post graduation. I ended up staying at her apartment and we had the worst sex of my life. Initially, I just couldn’t get turned on by her, and so we stopped. Then, later, in the middle of the night, sleeping on the floor next to her, I got aroused, woke her up, we started having what I thought was welcome sex, but then I asked her to get on top, and with an annoyed sigh, she said “look, I don’t mind having sex, but…” and I stopped right there. “You don’t mind?”
Elly
No one crushed my heart like Elly. We were housemates in a small group house. My buddies would visit, and always ask, “How can you stand living with that amazingly hot woman?” She had a steady boyfriend, but one night in her room, she said the immortal lines, “Have you ever wondered what it would feel like to kiss me?” She was already drunk, I think, on liquor, which she often mixed with Nyquil. We started having sex, and in the middle, she started saying “I’m just a dirty bitch, I’m nothing, a fucking whore.” It wasn’t a turn on. It seemed not erotic but psycho, possibly linked to her rejection of her stridently Christian family’s values.
Though the first time wasn’t great, we proceeded to have some of the best sex of my life over the next year, all of it behind the back of our other housemates and her boyfriend. She also liked sex without condoms—if I stopped to get one from my room, she often changed her mind about sex. I finally made an ultimatum—we have a real relationship, or this stops. She chose to stop.
I started dating someone — Ida— literally a week later. A few days later, Elly comes to my room, at about midnight, and she tells me that she thinks she made the wrong decision, but knows it’s too late. So then I’m cheating on the new girlfriend, one week into the relationship. And then when I break up with Ida a few weeks later, and Elly and I go public, it turns out another housemate had been obsessed with her. He was enraged that we were together. Drama, threats of violence, tears. Elly and I talk about finding a place together, but in the end, I move out alone, descend into a dark five month depression, and Elly stays in our beautiful group house.
Ida
Poor Ida. She was in my b-school, she was very exotic and Italian, and she came to a party at my house. We ended up in my bed. That’s how our relationship started. The sex was very good, although she was something of a conservative Catholic Italian in most cultural ways. But I was completely distracted for the whole four weeks by Elly.
Katrina
I had moved down South to start a new job. I met Katrina at a local theater group. She was the manager of a jewelry counter at the large department store downtown. We came from different worlds, but it was a nice, drama free relationship after the chaos of Elly. The second woman in a row that I’d dated who was divorced, which made me feel very adult, somehow. It lasted about 4 months, I think. But I was still messed up over Elly the whole time.
Nea
She was a Swedish goddess behind thick glasses. At a summer program on business finance, she was one of the only women, and everyone was nuts about her body, the tight skirts she wore to class, that accent. We danced wildly at a party, then ended up at my place, I think. She wasn’t interested in a relationship, and I took it with unexpected immaturity.
Barbara
She was an actress. She was terribly artistic (shocking), prone to sweeping emotional highs and lows despite anti-depressants. She also thought she was ugly, which was hard to accept. She really wanted to live together and then get married, and she was the first woman whose biological clock was ticking audibly during our relationship. I just had, as usual, too many doubts, so her certainty scared me to death. When I broke up with her for the second and final time, she asked me to come with her to see her therapist, so she could get closure. That was weird.
Marcy
The first woman I slept with that I met online. She posted something about being a recent Ivy League grad who was buxom. And boy, was she buxom, like a miniature Rubens woman. Our third date was out to a wedding in Colorado, and we had sex like weasels on meth for two days in the hotel.
Beatrice
Beatrice was sexy and vivacious with a down home Southern charm. We met at a professional conference, and at the time she had both a girlfriend and a boyfriend back home. We hooked up anyway, and in the middle, she suddenly passed out. It was very strange, just as I was pulling down her panties, lying facedown on the hotel bed. We stayed in touch, she broke up with both lovers, we started dating, but it was always iffy on her end. For once I knew for sure that I was into a girl, and she did a fairly good imitation of me, all uncertainty and shifting preferences. She came to spend Christmas with me, brought a framed picture of herself as a gift, made my whole family fall in love with her, then on New Year’s eve morning, just tells me that she isn’t sure but maybe we should just be friends. Still the worst NYE of my life.
Olivia
She had been one of our interns the year before, and when she came back to my office, asking for advice on graduate schools, was it coincidental that she was wearing the shortest shorts I had ever seen? Turns out, no. Livy was stunningly beautiful, with a runner’s body. I invited her to watch my apartment while I was away for a few weeks, which gave her a place to stay in town. There was “accidentally” two days of overlap at the start of her stay. I played it cool—the first night, I made no moves. The second night, she got to drinking, and we had some just okay sex, but just seeing her gorgeous body naked was an incredible thrill.
Isabel
She was another intern at the office, and I once again waited until the program was over to date her. And what a career driven wench she was. It was like Reese Witherspoon’s character in Election. I was her first serious relationship, I think. She was never that into sex, at least with me. She started business school 4 hours away, and we met up for months, spent the holidays together. But I was never that into it, and so when I met Bridgit…
Bridgit
A very religious girl who hid it until we were already involved, Bridgit was on many levels quite compatible with me. We had similar interests, both very verbal, and she had a marvelous sex drive. Which made her feel quite guilty, in a Christian way. Some of the best sex we had was in a tent surrounded by other tents in a campsite in South Dakota, driving cross country. also this one time in the shower, soap as lube. I was also her first serious relationship, the only prior one being a messy affair with a married colleague that had messed her up for almost two years before our first date.
Karla
She was another former intern, and this time we cut it kind of close, two days after she left the office. She was dating a drug dealer at the time, and she used me to break up with him.
Teresa
A colleague at my old job, we hooked up my final night in town. She was a very sexual person, very open about her many assignations. It felt like I was fucking a slightly older female version of myself at certain points. There was no danger of emotional commitment.
Francine
My first experience with paid sex. It was right after 9-11, and that feeling of “we could all die any day” was probably part of what got me to do it. Also, I wanted to see if a pro could make me come faster, as I was tired of taking a long time to ejaculate during intercourse. It was almost scientific research. She was a very cute Korean girl, and Francine was certainly not her real name. The sex wasn’t that good, and I ended up having to finish myself with my hand, as I got self-conscious of how long it was taking even more with a girl who was only there for money.
Kandice
I dated her my senior year in high school. But we never had sex, although we came fumblingly close. Then, we met up a decade later at a party, just hit it off. We went out for about 8 months.
Terry
We met online, at Match.com. She was a year older, very polished and professional. So we are having sex on our third date, at my apartment, and we start talking about orgasms. She eventually confesses that she has never, in fact, had an orgasm with anyone and that she can only orgasm one way—with extremely strong water jets directly on her clit. I said “I would love to see that.” And she was incredibly turned on by the idea of showing someone her orgasm. So we got into my tub. I didn’t have the nozzle that she favored, but by placing her legs on either side of my downspout, she was able to get just the right pressure. It was impossibly hot to watch, to hold her as she writhed. It only lasted two weeks, I think.
Bella
We met at a party through mutual friends. Bella was younger, a short buxom blonde with a pixie haircut. It bothered her that I wasn’t more blown away by her shapely huge breasts. She was the only woman I dated who called them “the girls” relatively unironically. We argued one night when watching the presidential debates, I thought she was too hard on Bush. She dumped me a week later, saying it was “no fun.”
Tammy
I met her at Match.com personals. She swore in her ad she could beat anyone at chess, and damned if that wasn’t true. I thought I was good—Tammy was a goddamn master. We went out for two years, and the sexual highlight could have been our invention of sex chess—you have to be the other person’s slave for a certain number of minutes depending on the value of the piece you capture. Queening took on a whole new meaning.
Deb
She was Tammy’s friend, and I noticed her while we were going out. Then, a few months after we broke up, at a friend’s party, she was angry at the video game console, and just kept shouting “fuck me! Fuck me!” as her avatar died. Prophetic words. It was as the party was winding down, until it was just me, the host and Deb. Deb invited me to stay, and I realized I was being invited to a threesome when the skeevy host brought out condoms and lube. She started going down on him, I entered her from behind after going down on her, then we tried a DP. Unfortunately, skeevy could not get hard enough to do his job in front, while I was hard at work in back. There was a moment when I had complete confirmation of my heterosexuality, oddly enough, as my legs by necessity brushed against his. The contrast between her silken thighs and his hairy ones was so clear, and so conclusive. The threesome itself was so arousing that I came quickly during traditional sex while wearing a condom, somewhat of a rarity for me. Then she demanded that we both jack off onto her tits. As I left around 4 am, they were still at it. I remember feeling empty, something had been crossed off a bucket list that I wasn’t aware of having.
Na
I met her at a party, and surprised her with my Chinese. We dated for about six weeks, and the whole time, she wouldn’t let me come to her house. She said she lived way out with a really conservative aunt, and couldn’t have men over, or even stay out too late. And when I went out with her co-workers, they treated me very strangely, really unfriendly. Couldn’t figure it out. Months after we broke up, I found out she had been living with her husband and 5-year-old child.
Lacey
Lacey was a middle school teacher, much younger, and a bit shy. I had doubts at the start, and they haunted me throughout our short time. I really agonized that I shouldn’t be with her if I wasn’t sure, a more intense feeling that I was already familiar with from other relationships. When I broke up with her one Sunday morning in bed (classy), she said, “you’re a good egg, but a little scrambled.”
Marie 2
We met professionally. She invited me to her place for dinner, to talk about “business” but it was clear to both of us where this was going. She was just coming out of a divorce, his stuff was still in her townhouse. I had never been with a really obese woman before, although plump had never bothered me. I don’t think her weight was why the sex was really lame, but it was undeniably bad. Never saw her again.
Nita
A little Indian-American girl I met at my kickball league game. She had a thick Boston accent, oddly enough. We bonded over mutual depression stories. She was very sexual, and I loved when she rode me. Can’t remember why we broke up, just that it was bumpy and without clear boundaries. She called me at 2 am while she was going through a terrible panic attack a few weeks after I started seeing Tanya, and I went over there and held her, and didn’t try to have sex with her, which I felt was a personal triumph.
Tanya
The last woman I slept with who was older than me, she was just on the edge of matronly, and not in a MILFy way. But she was sharp as a whip, witty, and fun, and we had one of the great first dates of my life. I got her almost naked in the courtyard of her very posh apartment building. It was mostly downhill from there.
Olga
My second, and I believe final, experience with paid sex. It was at a brothel in Amsterdam, and I was so captivated by the legality of it that I forgot that the reason it hadn’t been that good in the states had had nothing to do with illegality. It was embarrassing to be in the position of selecting from three women who came into my room in their lingerie. I chose the one who looked most like my college girlfriend. I’m sure she would be flattered by the homage. And again, paid sex ended up with observed masturbation, this time with undisguised boredom on a laconic Turkish face.
Marie
The last of the interns, and by now, the age gap was getting pretty huge (she was 21 and I was 38). It began at an office party that featured dancing, and we had one of those immediate kismetic dance interactions, her moves and my moves just fit. Luckily, the party was the last day of intern period, and we saw each other the next night, and had really bad sex. I honestly couldn’t stay awake after the very long date (bar, dinner, movie, bar, bar) and it felt like a warning—this girl has too much energy, you’re an old man.
Marlise
The woman who finally got me to settle down. It’s been 4 years, which is a record for me. The sex was great from the very start. She was trapped in a marriage without physical contact, let alone sex, and so it was like having sex with a prison escapee. There are things wrong with our relationship, as with any relationship, but sex is not one of them.
