Everyone Ive Ever Had Sex With

Everyone I’ve Ever Had Sex With: Male, 42, New York

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My bride. We were both virgins at our wedding; I was 22 and she was 23. We’d fooled around a bit before tying the knot, but full-on sex was reserved for that special night. It took a good couple of months for us to figure out what worked and what didn’t, and then we spent a relatively blissful two years making up for lost time. Sadly, the routine we settled into over the next decade didn’t include most of the activities that other folks take for granted. Sharon doesn’t like to go down on me. She doesn’t like when I go down on her. Forget anal and toys. I began blogging about my frustrations, and to my surprise, there were women reading my stuff.

Donna was a fan of my writing, recently divorced, and looking to assert herself sexually. She invited me out for drinks and seduced me thoroughly. We made out in dimly lit bars a couple of times, and I brought her to orgasm in the car after we celebrated my birthday at a raunchy dive in the Village. I visited her apartment a few times for rushed and awkward trysts over the next year, but we didn’t have enough in common to sustain a real spark. We are still friendly in ‘real life.’

Another divorced online correspondent, Raianne is 10 years my senior and very comfortable with her sexuality. We met soon after things got quiet with Donna, and we connected as friends and lovers. Raianne is the first woman who gave me oral to completion, the first with whom I had full intercourse (aside from Sharon). She lives thousands of miles away, but we still see one another every couple of years.

Rosie was separated from her husband and enjoying her newfound freedom by meeting guys online and hooking up with them whenever the opportunity arose. A friend – who had already slept with her – told me to drop her a note. I visited her apartment and we had what can only be described as terrible sex. She got off on telling me how I was committing adultery and how she wanted me to fuck her with my “married dick.” The strangeness didn’t keep me away, however. I went over there twice more, which was enough to figure out that I was reasonably skilled and considerate in bed, and she wasn’t.

This is where things get complicated, because Liz and I had been coworkers and friends for years – throughout the slow journey of discovery that played out in my first extramarital forays. I was head-over-heels in love with Liz for a long time, but she maintained firm boundaries. She was also married, and had also been with nobody else but her husband. Then she made out with a hot French guy while overseas on business and realized that her boundaries were a little more flexible. Upon her return, she initiated a physical relationship with me that lasted a few months. No sex, but plenty of everything-but. She was consumed with guilt, though, and her husband figured out that we were more than friends when he saw an errant text message. The romance ended abruptly, but we’re both still married to our respective spouses and still close friends.

Kate was my rebound from Liz, but she turned into much more. We went from coworkers to friends to lovers over a heady year, and then spent eight months in a deep and loving relationship. Kate and I were very in sync, intellectually and sexually, and she helped me (more than she knows, probably) gain confidence in myself. We knew at the outset that my being married was going to complicate things, but we agreed to go for it anyway. The relationship ended when my marriage became too much to ignore comfortably, but we stayed good friends for another few years.

Beth is another woman I met through my blog. She was also unhappily married and ‘acting out’ sexually. We began seeing each other around the time things slowed down with Kate. I’d had enough of being ‘in love’ at that point, so Beth and I agreed to keep things strictly sexual. Over the next two years, we’d hook up whenever our schedules permitted. The sex was always uninhibited, energetic, and exciting. Beth and I couldn’t avoid becoming close friends, either, but we were very careful not to call it love. Ultimately, Beth’s husband caught her in flagrante with another guy, and she cut ties with me as a result.

I’d been friends with Anne for 15 years — we met online back in college, when the Internet was brand-spanking-new. After a months-long e-mail flirtation, we met in person at a concert. Sparks didn’t fly, but we stayed friends even after I got married, as she dated a close friend of mine for several years. I’d never made a secret of my attraction to her, though, and as the years passed, we confided in one another more and more about our respective sexual adventures. Eventually, she decided having sex with me wouldn’t endanger our friendship, and we hooked up twice. The dynamic was very skewed; it was all about me having the privilege of touching her and did not involve any reciprocation. We’re still close friends, though, and I imagine we may have more-balanced sex sometime in the future.

Sleeping with Rachel was a mistake. At this point, I was in my late 30s and she was 21 — a lithe and sexy ingenue whose youth and willingness overwhelmed my better judgement. A mutual friend introduced us and we got together once in a popular hot-sheets motel. The sex was abysmal. My best efforts didn’t raise so much as a sigh of pleasure from her. She seemed checked-out, physically and emotionally. Dispirited, our ‘date’ ended with me masturbating while she assured me that she’d love to see me again. I found out later that she was on several powerful psychotropic medications when she met me. I still feel badly about the whole thing, but she’s married now and seems happy, so I guess it’s behind her.

I met Randy four years ago on Facebook, and we’ve been having incredible sex ever since. She’s my age, married with kids, and she’s been stepping out on her husband even longer than I’ve been stepping out on my wife. She’s very strong-willed and intense; we’ve had plenty of ups and downs over the years, but we love each other and our sexual chemistry shows no signs of abating. It took a long time for me to admit that I love her, and my insecurities and hangups still get in the way sometimes. That’s what leads us to Lisa.

Lisa’s another Facebook friend who flirted with me and expressed an interest in meeting up. How could I say no? Well, I could have, but I couldn’t see myself passing up an opportunity. She’s also married, but she enjoys a relatively ‘open’ relationship with her husband. Sex with Lisa is uninhibited and fun, and she’s very adamant that we don’t develop any messy attachment. As time goes on, however, I don’t see how we can avoid it.