Men I’ve had sex with

This is the full list of the men I’ve had sex with. Originally I wrote this as a series of posts, but then realized I should create a static page which I can add to as I go. Since I’m hardly done this list…

For anyone that I’ve written more than one post about, I have linked to my “Lovers Page” for simplicity, or their tag.

  1. Age 13. My first. The 17-year-old who lived up the street, who introduced me to motorcycles, Def Leppard, and Led Zeppelin. We dated for 3 months.
  2. The one I wish was my first. He was my boyfriend in grade 7, for 6 months!  Drove our mothers crazy at the thought. We got back together at age 14. I was his first and we had a lot of fun exploring sex together for 4 months.
  3. A hot guy from my neighborhood. We had sex in his grandparents house while they were away for the winter. The only thing available to sneak out of their liquor cabinet was Mint Schnapps. I still think of him every time I see a bottle. Years later he ended up playing a popular stuffed mascot on a children’s tv show. My friends mocked me incessantly that I’d slept with [the character].
  4. The rebellious alternative guy who introduced me to the Smiths and the Cure. We dated for a few months. He’s now married to another woman from my high school and he hasn’t aged well. We are Facebook friends.
  5. Age 15. The rock star. I was his first, at age 17. We dated for 18 months and he broke crushed my heart. He’s still married to the woman he cheated on me with and broke up with me for. He continued to sleep with me for months after we broke up. He’s a rock star. Literally. I have some stories to share about him.
  6. Age 16. A very muscular dude I picked up whilst on a beach vacation with a cousin and a friend.  My friend is a redhead, my cousin dark haired, and I am blonde. We terrorized that beach that weekend. I have no idea what that guy’s last name is, but I do have pictures of him.
  7. Another alternative guy from my high school who was a classic bad boy. Treated me, and a few of my friends, like shit.  We are also Facebook friends and he’s handsome but no sign of the bad dude he used to be.
  8. Age 17. My second real high school romance. Two years, one year too many. We were in love, but he wasn’t right for me. I tried to break it off several times but he didn’t want to hear it.  When he finally did, we were both working on a stage play together and he read my journal which included me sleeping with another man and he told the. entire. crew. over the headsets.
  9. The much older man who I first met in a foreign country at age 14. He completely captivated me and we had a totally non-physical, but heady, time together.  I still have all the letters he wrote me. He came to my city to visit and I stayed in his hotel and fucked him and also realized things were different.  And yeah, my ex-boyfriend (#8) read all about it.
  10. A fling during a foreign beach vacation. He picked me up by the pool, we had an awesome time together, and I informed my Mom I was staying another week to live with him. He introduced me to anal sex (I didn’t do it again for many years). With him, I had my first threesome – on the beach, no less.

Thus ends the high school list. I sped up a bit in university.

  1. The leader of my “frosh week” group who was lovely and smart. I have no idea why we broke it off after 2 months together.
  2. A foreign speaking guy who picked me up at a nightclub on the dance floor. His accent was super hot. We lasted 2 months but I didn’t ever write down his last name.
  3. A guy I met in high school who was dubbed “nordic man” by me and my friends because he was gigantically tall and blond.  We had an on-again off-again relationship for several months.  I saw him recently at a sports game and he has not aged well.
  4. The creatively named #14 on this blog. The first man I met who I could see myself living with. A few years older, had his shit together, smart, funny guy. I met his parents, we went on a trip together, and it was great. Until we ended up not having sex because he had issues, and became just friends. It fizzled. A couple of months later we ran into each other at a bar and he picked me up and we had the hottest sex ever. Now he’s an attorney and lives pretty close to me. We reconnected over coffee two years ago. I think he’s still single, but imagine he’s still fucked up about sex. Update: We’ve had some fun times together, and have stayed friends. Click on the link above to see the posts that he’s featured in.
  5. A football (American football) player. He had the biggest biceps on the entire team. Prematurely balding. I really liked him but it was only an off-and-on thing…for a couple of years.
  6. A very close family friend. Some would say he was like my brother. But I’d always had a crush on him and one night we were out partying at a bar and the tequila body shots started and, well, we finished it. It lasted a few months but we were in different cities and our families didn’t know, and he met the woman who would be his ex-wife.
  7. A football player. Yes, you will notice a pattern. He was in his final year and I in my first, when we met. We slept together a few times, usually after chinese food dinners or hanging out at bars.  After one notable night, the next day he introduced me to his fiance. I was mortified…I had no idea. I do think I slept with him again, however.
  8. Another football player. I think we fucked in my student council office one night after being at the bar together. He was the quarterback. My roommates ran round saying “Ann sacked the quarterback” for days afterwards.
  9. A military dude, who had the quickest recovery period of any lover I’ve ever had. He was amazing. We were together a few months and I have to read my diary from that time to remember why we broke it off.
  10. Another football player and a bouncer at a bar. We were friends and I’d liked him for a while. Once we stayed at the campus pub after it shut down, played strip pool, and ended up having sex on the pool table and in the kitchen at the bar.
  11. A professional football player. I quite liked him and I thought he liked me too. Until he disappeared for two weeks with no contact and I found out afterwards he also used cocaine a lot. Ironically he now works for my company, but a long distance away.
  12. The first dude named Mike I forgot when I created this list.
  13. The second dude named Mike I forgot when I created this list. Don’t judge. Yes, there were two. Mikes. I forgot.
  14. The manager of the campus theater. I guess he was kind of my professor for my practical theatre classes. He was older, and had a goatee, and wasn’t big or strong. But he really liked me and cooked me dinners (I still remember the pad thai he made for me once), and I was bored. He loved to eat pussy and it was my first experience with someone who would go down on me forever. We spent a summer together and I’m ashamed to say I broke up with him when the football players and actors came back in September.
  15. Oh, this guy. He was a contractor at the campus pub that was being renovated over the summer. We argued like crazy. He lived about an hour’s north of campus and after one particularly stressful night he asked me if I wanted to go to his place in the country to relax. Why the heck not. The sex was a one-time thing, but he still sent me a huge bouquet of flowers to my student council office and I had to lie to all my friends about who it was that sent them.
  16. A football player and bouncer. He was a friend first, and he knew about all the others. We fucked in the campus pub bathroom to “Closer” by Nine Inch Nails and it still makes me think of him. I don’t recall why we broke up, but I think we decided we’d be better friends than fuck buddies.
  17. A football player. A fucking gorgeous football player. We fucked just once, after a particularly raucous night of drinking, in my campus office, and I got rug burn on my knees. ‘Nuff said.
  18. I wish I knew who he was, but I have no clue whatsoever. Perhaps after this post goes up and I ruminate on it, it will come to me. Apparently I slept with him more than once, so this is a little embarrassing (yes, I indicate when it’s a one-time-only thing).
  19. One of the few that got away. I went to high school with him but he was a year older and hung out in a different crowd. Met him at a close friends wedding over Christmas break, and we were both single. He was 6’7″ and completely proportioned and we had astounding sex that night. I ripped his shirt off his body and we spent time the next morning picking all the buttons off the floor. He was in a different city for school but for months we emailed (on dial-up!) and talked on the phone and visited each other when we could. The sex with him was some of the best I’d ever had at the time. He ended up going off to the wilderness to fight fires and now he’s a helicopter pilot, married with children, and I resist looking at his Facebook page because he’s still so goddamned gorgeous.
  20. The actor. He and I worked on several shows together and there was fierce chemistry between us. I first kissed him in a taxicab after a party and realized the next day he didn’t remember. He smoked a lot of pot. We were off and on for two years, never exclusive. We would fuck for hours to “Blood Sugar Sex Magic” by the Red Hot Chili Peppers and that album still turns me on today. He introduced me to sex whilst high, all kinds of sex toys, and my second (and third) threesomes with #32.
  21. A stagehand. One night only, after a party (probably because #30 wasn’t available) and the fucker stole my favorite umbrella which was teal and by Totes. I wish the sex was more memorable than the loss of my umbrella, but such is life.
  22. An actor. Friend of #30. We had a threesome together twice and it was amazing. I will write about it separately. He thought however it meant that I’d sleep with him solo, and when I didn’t he was upset.
  23. Gorgeous tourist from Boston who I picked up in a bar. Accent that made me literally drop my panties. He told me he ran a funeral home which I’m sure was just a joke but I didn’t care. I really wished I would have seen him again. I can’t remember the sex but I can remember how crazy hot he was.
  24. A friend from school who I’d known for a couple of years. We moved back to our city and the friendship turned to sex. The sex was terrible, otherwise he may have been a good relationship candidate. He was the last man I slept with before my husband. We stayed friends for a while – my husband hated him – and ironically when I moved into my current house, he had just moved away from the building across the street. He’s still single and likely as intellectually crusty as I remember.

Then I met my (now) ex-husband, and it was all over after that.

  1. 1998. My husband. I had been on a series of bad dates and had pretty much given up on meeting anyone, when mutual friends introduced us. Our first phone conversation lasted 3 hours…our intellectual connection was undeniable. He was handsome, too. Put together, good job, good manners. We kissed on our first date, and on our third he took me dancing and we went back to his house and had sex for a couple of days off and on. He introduced me to fisting.

Look out, world. Turns out, my strong sex drive didn’t end when I was 25.

  1. Faraway Lover. The night we met is described in this post. He changed my life and I will never regret meeting him.
  2. Another Faraway Lover. I haven’t written about him, but he came into my life exactly when I needed him…when my heart was breaking over #36. We were away at a work event and he knew my job was changing which meant he’d likely not see me again. He knew he had to act if he wanted to tell me how he felt. And act he did.
  3. August 2013. My first date off online dating which was still one of the best. Great chemistry, lots in common, went back to his place for sex, he made me squirt…so the usual 🙂 – but he ended up being “too busy with work” for a second date. We did reconnect months later and he said a nice-on-the-surface-but-upon-reflection-really-dickish thing to me, which was pretty funny.
  4. Ariel. Still one of the best kissers on this entire list, and could fuck like a maniac.
  5. One who I really regret. Met on a dating site, hadn’t seen his face, agreed to meet up with the sole purpose of having sex. He was drunk and very strange but I fucked him anyway. He never looked at my face, just stared at my pussy the entire time. He left a baseball hat here and I suppose I should just toss it. I’m sure he doesn’t remember our night and I wish I didn’t either.
  6. One who evaporated after our first date which ended in a little bit of sex, but mostly him having hydraulics issues. I guess he was embarrassed. He had the nerve at dinner to suggest I wasn’t over my ex, when he spent hours complaining about how much of a bitch his ex was.
  7. John / The Personal Trainer
  8. Weird Super Tall Guy
  9. The Sweater
  10. The Out-of-Towner
  11. The 26-Year-old
  12. Mr Spontaneity
  13. Nice first date, nice follow-up date with decent sex…but this dude was obsessed with cleanliness. Like hop out of bed 5 seconds after finishing to “clean up”. He thought I wanted more than just sex, which I did, and he wasn’t ready for anything more. We are in the same industry in similar fields and we know some of the same people. I had coffee with him a few months ago but we haven’t spoken since.
  14. A young, hot, chef. I still remember the image of him in his low-slung jeans and big belt with no shirt on, standing in my kitchen. He had a full sleeve tattoo of his favorite fruits and vegetables. We had a fun first date where he came to my house afterwards, fucked me twice, then disappeared. He keeps coming back every couple of months to send me a cock shot and ask for a tit pic…would be funny to post his texts. He continued to sext me every once in a while and I always said no, until I said yes. It was not the greatest experience and I never heard from him again.
  15. One of the nicest, sweetest, most sincere guys on this list. An Italian dude with an epic cock who had no rhythm whatsoever, so it was completely wasted on him. We had no chemistry and the sex was terrible…but if I thought we could just be friends, I would. He actually just texted me a couple of days ago to say hi. [Update: almost two years later, he still texts me every once in a while]
  16. The Cook
  17. November 2013. Jason. He’s still around and introduced me to some new things.
  18. A guy in a city a few hours drive away, who was very kinky and would have gladly set me up with any combination of people for me. He came to my city twice… the first time we had fantastic sex on my couch and in my bedroom and he slept over, the second time was just as fantastic. I got a tattoo the next day…which is a total non-sequitur but for some reason I remember that. He’s a high school guidance counselor of all things. He texts me every once in a while but I haven’t seen him in months.
  19. I should write about this dude. He was a total exhibitionist, worked in my city but lived a 90 minute drive away. The first date I drove to his city the night before a work event. We had a great dinner, fun in the spa at his gym, which included him fucking me in the change room with a massive mirror. He had a thing for mirrors. The second time I went to see him our sons, same age with the same name, played outside together and he took me into his locked office and I rode him on his desk chair. He was interested in going to a swingers club with me but things just faded due to our general lack of availability. He’s come back.
  20. One of the biggest players in this list. A guidance counselor for at-risk youth, of all things. Pursued me with the most romantic language ever, was all sweetness and light. I foolishly agreed to meet him at my place where he fucked me from behind in my kitchen. Afterwards we talked for another hour and then the next day he deleted our BBM chat history and I never heard from him again. [Update: Until I went back online months ago and he tried to convince me he was sorry]
  21. The plumber. No, not something from a porn movie. Best dressed of all the men on this list, great mental and physical connection, lovely first lunch date. Second date we ended up having sex and it was terrific, but it turned out to be all he was looking for. He had the best line probably in my dating ever – I told him I thought he only wanted sex, and if I wasn’t worth taking out for a drink beforehand, I wasn’t going to fuck him. His response? “I liked it when we had a drink first at your place”. Wish I was kidding. That was the end of him.
  22. Naked Ironing Man
  23. The guy who broke up with me for not committing
  24. A really nice, crazy fit, 49-year-old who I met at the same time at #56. We had some great dates, he brought me flowers twice, serenaded me on his guitar, and was all an all-around terrific guy. He was great with his hands but sadly, didn’t have the same skill with anything else. I wanted to like him a lot but just wasn’t feeling it…and we just faded away.
  25. P / Shenanigans
  26. My Giant
  27. The third of three colleagues I slept with. Crazy hot dude.
  28. Sochi
  29. Jake. I was horny and sad at my state in dating. We met online and met that night for a drink, then I took him back to my place. He was a big, aggressive dude, and the sex was okay, but then I went away on vacation and was completely blase about him and just disappeared. Two years later we’ve had our second date and not sure what will happen next.
  30. A 23-year-old who told me he would be “my best lover ever”. Far from it. Yes, he was stupid young and I regretted it the moment he walked in my door. ‘Nuff said.
  31. The fuck-and-leave from my failed film festival week
  32. The oldest guy I’ve ever slept with
  33. A young, energetic dude who was funny and interesting. We had a hilarious first date where we regaled each other with dating and sex stories. We had sex…he was so keen and eager to please but his moves weren’t great and his main asset, was, um… very minimal. I felt nothing physically. Then I felt bad. We went out again for a second time as friends because he provided an interesting insight into the male mind. But he couldn’t understand that I didn’t want to sleep with him again, so I stopped responding to his texts.
  34. May 2014. Johnny Id. He has his own page; I will let that speak for itself.

Johnny and I were together for 5 months. When it was over, I decided to be a *bit* more selective. But it’s all relative, I suppose. Sometimes I had sex with former lovers Jason (#52) and Shenanigans (#60).

  1. September 2014. Dan. I met him out dancing with girlfriends, took him home, and had sex with him. He was kind enough to respond whenever I texted him, but left to his own volition he never reached out. We had sex a few times. I still wish I knew what his back story was.
  2. October 2014. Andrew, who I met for a threesome and ended up dating for 6 weeks. He had a big cock and could make me squirt with it. But my relief at meeting someone with whom there could be potential became intention and intensity and he backed away, unable to handle it.
  3. A lawyer who had potential but, after coming over one night fucking me on my couch and never removing his tie, shockingly it didn’t really go anywhere.
  4. The Dog Trainer. Provider of my first spanking. A dirty, dirty man, who would have been very pleased to control all aspects of my life. Despite some great chemistry over the phone, I just couldn’t do it and cut it off after a few dates.
  5. December 2014. Tony. Oh, Tony… my heart will always have a little place carved out, just for him.

Tony and I were together for almost 6 months. Right before we broke up, we took a three-week break where I got up to some serious crazy-time sex.

  1. May 2015. Mr Tinder, who had me squirting within minutes but went too far trying to fist me on a first date.
  2. My first swingers club experience as a unicorn. First guy I fucked there was Dale, while his wife watched.
  3. Swingers club. Anonymous dude #1
  4. Anonymous dude #2
  5. Anonymous dude #3; full swap with him and his wife, me and Jason.
  6. My second swingers club experience as a unicorn…this time at a gangbang night. First guy I fucked there was Kris, who was my “spotter” when Jason didn’t show up.
  7. Anonymous gangbang dude #2 who technically penetrated me but had a hard time keeping it, well, hard.
  8. Anonymous gangbang dude #3 who was older and chubby but had really good moves. And no, in case you are wondering, having read the rest of the story…the Dom and others didn’t fuck me.

The break turned into a full breakup, and I was back to dating. 

  1. June 2015. A guy I met on FetLife. I met him for a tea when I was sick, not expecting to be completely taken by his penetrating stare and luscious mouth. I brought him back to my place where I discovered his kinks aren’t really my kinks.
  2. Lewis, who had more to offer than his huge cock but who unfortunately disappeared. I reached out again after Tony and he’s become a fuck buddy.
  3. A daytime delight I met on Fetlife.
  4. Sex club full swap with Jason
  5. Another daytime delight I met on Fetlife.
  6. Fox (my boyfriend for about three months. It didn’t end well)

When things ended with Fox, Tony (#74) came back into my life. We stayed together for three months (“Chapter Two”) until I broke it off yet again. I’ve had some sexy times with Lewis (#84) since then, and some others. Tony and I also had several times together…of course. I was still having occasional sex with him a year later. 

  1. A man I met on OK Cupid and dated for almost two months. Super intense on both ends of the spectrum. Didn’t end well and his story is gone from the blog. I call him HWSNBN and if you don’t know what that stands for, go read some Harry Potter.
  2. A man I met via this blog, one night while on a business trip.
  3. Clark, the third of a threesome I had with Lewis, who fucked me seriously well and wanted a repeat. We subsequently had a foursome (and fivesome, and solo encounters!).
  4. Another man I met via this blog, who came over one night while on a business trip. It involved fisting.
  5. Ian, who I went on three dates with but a) he got weird and b) changed his mind about the distance between us.
  6. Doug, a “sailor” who I fucked on the first date on his boat, and regretted it by the second date.
  7. The third man I had over for group sex with Lewis, Clark, and Val.
  8. Drew, who I saw a few times for dates. Low key, believes in karma, and not looking for anything serious. Potential to be a good FWB. After he lied on a date and set up either a drug sale or a booty call with another woman, it’s not going to happen.
  9. Ron, a married-ish business man I met on a work trip.
  10. Todd, another man I met through Lewis. We had immediate intellectual and physical chemistry, one of those crazy connections. Turns out, however, in addition to living in a different city, he’s married.
  11. Alan, a tradesman who was sweet, bringing me flowers and cooking for me often, and kind of naughty too. He wanted to be exclusive before I was ready, and ultimately there were far too many differences between us, he wasn’t there for me when he should have been, and I broke it off, via text. He still texts me; a recent one was him naked in a Trump mask. I wish I was kidding.
  12. Leo takes the century spot. A very nice, stand-up guy who I dated non-exclusively for months, he joined me on a couple of trips but we were ultimately not compatible.
  13. I absolutely HATE that this guy is the one who took me over the century mark. Oh well, haven’t had a mild regret in a while.
  14. Jack. The first man I met from my most recent journey in online dating. Jack turned out to be a master manipulator and liar. A man all about the pursuit, at any cost. The cost was me. I think anyone would have fallen for his words.
  15. Charles was the latest man Lewis introduced me to. We had one of the best first kisses ever but unfortunately, he’s in a relationship so I am unlikely to taste his delights again anytime soon.
  16. Ray was very good with his hands, but sadly he wasn’t so good with the short commute between our houses. He was honest enough to say he couldn’t commit to a relationship because of our distance.
  17. Bruce held my attention for six weeks with regular phone calls and great banter. I only got to experience his magic penis twice. He realized he wasn’t near ready to date.
  18. The landscaper I met on Bumble who broke the three-week dry spell I had post-surgery. I knew on our first date he wouldn’t be my soulmate, but he made me laugh and his hands were really strong looking. He slept through the planned meet time of our second date but I invited him over for a booty call.
  19. A mid-fifties poet who seemed too soft for me, until we got into bed together. Outside the bedroom, he’s just not for me.
  20. The high-end tradesman with whom I had a few great phone calls before meeting him: a first date that felt like a third, so we had sex and he stayed overnight with morning promises to see me again. His communication since has been underwhelming.
  21. Dan the Plumber. Super cute, and super odd. In several months we’ve only had sex a few times, but he came for Christmas dinner and made friends with my Mom.
  22. Ugh. One of the kinda-catfish. I hate that he’s on this list. I don’t think I wrote about him; he doesn’t deserve my words.
  23. Gregory. Had what I thought was great potential; we had an insane amount in common. Unbelievably, a reader was a friend, recognized him, and told him about my blog. He read I was excited about our potential, and ended it.
  24. Zane, an intelligent and soft-spoken 35-year old who seemingly digs me. Not sure where things will go, if anywhere.

17 thoughts on “Men I’ve had sex with

  1. I enjoyed reading the list, although I didn’t read the whole thing. Can you blame me? It’s really long – which is good for you btw 😉
    I like the comments – he hasn’t aged well, and prematurely bold. It always makes me feel better when I see people my age looking worse than me. I know, I’m a bitch.
    I am very curious about the rock star. Is he known in Europe?

  2. Saw your comment on Gretchen’s Sisterwives post and had to come read this. My list would be much shorter (I’m 19!) but is also chock full of bizarre stories. You earned yourself another reader!

    • Sabina – thank you and welcome!! I can tell you at 19, I felt a lot of shame around my sexual habits. Granted, sometimes it was about trying to feel good about myself, and liking the attention of men… but I’ve realized I’m also simply a very sexual person.

      From what I’ve read, it’s different today for women your age. But I don’t know if that’s really true… what do you think?

      • Yes and no. It’s very complicated. The hookup culture in college is prevalent, and generally women aren’t highly shamed for having sex with people they don’t know that well. At the same time, though, there does seem to be a cut off point at which it becomes not okay/makes her a slut. I think a lot of girls feel like they are pressured to have to settle for hookups when what they want is a relationship because of how normalized hookup culture has become, and that’s not exactly healthy sexuality either.

  3. Loved this article and just from the the first read, I love you! I love your uninhibited and raw nature and the zero amount of fucks given for negative opinions about your sex life. It’s extremely empowering to find and read an article that remotely articulates things I have done and felt. Me and my best friend have lists, stared them at age 20 or so and she actually keeps mine with her and updates it for me.

  4. Ahh, yes…

    Ms. St. Vincent, I owe you a thousand apologies and myself a death by a thousand cuts. So concentrated on simultaneously keeping pace with your current posts and working through your back catalog, I had completely forgotten these, your categorized Pages.

    Were I a spot less dense, our earlier, superfluous exchange would not have even occured. Your patient indulgence and gentility in not lambasting my obtuseness could not be more humbly appreciated.

  5. 100? Fuck! Or rather Fuck x 100!!!!
    I’m in awe.
    Actually this makes me feel frigid. (And can you have a word with my Wife please?)
    It looks like you’d fucked more people by the end of first term at Uni than I have. Ever. I know it’s quality that counts, not quantity, but fuck! I’m in awe.
    Anyway, I’m intrigued to sit down and digest this list properly. (It might take a while.)

  6. Hello Ann . I read many topics of you and stopped here for a while .. May people think you are whore or whatever. But I see that you are hungry of love not sex. Yes all of us need love . Real love, deep love, unconditional live and eternal love . We need To love and to be loved. There’s a quote says ( men give love to got a sex but wine give sex to got love) . Almost I believe in it . I don’t know how you look pretty or sexy . But real love should continue. It requires effort to pass obstacles. Those who give love to got sex . They have fake love. Because live in their mind is a way not a target.. hmmm I am not a saint . I am also guilty in some ways .. But what attracted me in your page . That you have tender heart easy broken but highly sensitive and sweet emotionally . You deserve more . You need to take deep breath and wait for long relationship with this unconditional love . Sorry it my wish to you not advise. Have a good life dear Ann

  7. I have really been enjoying reading your blog and have admired your frankness about your sexuality. I have struggle internally with my own sexual needs and desires and have slowly come to terms and accepted it is who I am and it is very refreshing to come across someone who is also open and accepting of her own sexuality. I started keeping a list and lost track, I could try and track it again I suppose, maybe I will one day and put together a blog post about it!! For the first 50 years of my life I only had sex with 2 men, both of them husbands. The last 18 months I am in double digits!!

What do you think?