Love & Sex

Everyone I’ve Ever Had Sex With: Female, 22, Boston

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It was hard to let go of such a good friends with benefits.

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My Kind of First Time
I was the virgin in high school that everyone thought otherwise. Before meeting him, I had a few "wait, you're a virgin?" situations that always fell through. I had made out with him a few times, until one night, he asked my friend and me to hang out with him, leading to a three way make out session. She left and so we continued. When he unzipped his pants, seeing his rather large penis made me blurt out, "I'm a virgin." He said "okay," and proceeded. After a few pokes, we gave up because it was hurting me too much. I was 17 at the time and we're still friends.

My Best Friend's First Boyfriend
We got along really well while my friend and him were dating. They broke up and a few weeks later, I found myself hanging out with him at my neighbor's house (which I was house sitting). It was quick and a little awkward, but surprisingly felt pretty good for my real first time. We hooked up a few more times but then the summer ended and I went to college across the country. I never told my friend about it and I haven't seen him since. 

The Bro
We were in the same friend group in high school and were always flirty with one another. One summer we started making out at a party, which led to us trying to have sex in my car but he had a case of whiskey dick. He invited me over the next week; turns out his dick was just small and he blamed it on the whiskey. We're still friends but are kind of mean to each other. 

Superman
I had just transferred to another college and although I had a few friends, I was feeling rather lonely. I made an OkCupid account and started chatting with a guy that looked like Clark Kent. After a few weeks of talking dirty and swapping nudes, I invited him over. He was tall, handsome, and built. We made small talk until he suddenly started fondling me. He was a little forceful and scared me a bit; I was sure he was going to fuck me and then murder me. Turns out he just liked it rough and helped me to discover that I liked the same. He gave me my first orgasm. I never saw him again. 

Stupid Engineer #1
We met on a camping trip through school. He asked me to hang out when we got back to campus and after a date or two, we finally had sex in my dorm room. He finished in my bathroom and although he was weird, the sex was decent, and I was starting to like him. I went home for a few weeks and when I got back, he told me he was seeing someone else. No hard feelings there but a few days later he called me up and accused me of giving him HIV, even though he got negative test results back. I made out with his friend at his birthday party as a "fuck you." Fuck him.

The Cuban
I studied abroad for a month in Cuba, where I met Sam. We met one night when my friends decided to go down to the waterfront to have a few drinks. He introduced himself and after what I thought was just friendly conversation, he asked if I'd consider having sex with him. I told him I'd think about. After a few days of teasing him and letting him get me off, we finally did the deed on a bench in the park. We had a few more outdoor excursions, including an alley way and a pseudo-foursome in an elementary school handball court that I refuse to go into detail about. It has scarred me to this day.

Kinky Online Matt
I had a craving for rough, anonymous sex. I stumbled upon Matt's profile and sent him a rather forward message. He gave me his number and after talking for a few days, I asked him to come over. After chatting over a couple of beers, I undressed myself in front of him and we went at it like two horny teenagers. We saw each other a few times a week, strictly for sex. He introduced me to BDSM and made me come every time. This continued for a month or so until he moved to another state.

My Friend's Friend
I took a weekend to visit with friends at the first college I went to. My friend that I was staying with was having a party. After a few lines of blow and a million drinks later, I felt it was time to sleep. Another friend of theirs was crashing so we had to share the pull out couch. We laid in bed chatting for an hour until I decided I was tired of all the sexual tension, so I kissed him. We started taking each other's clothes off and when he was about to stick it in there, he asked, "Are you sure this is okay?" I told him it was fine and he went at it for about a minute. We spooned to sleep and had a semi-awkward group breakfast the next morning.

The EMT
We met online and had really good chemistry the first time he came over. He was beefy and energetic and fucked me like a mad man. We slept together on and off for months until he started dating someone. It was hard to let go of such a good friends with benefits.

Stupid Engineer #2
We met one night when we were working an event. It was obvious he liked me and although I wasn't initially interested, I hadn't been asked out in a while and was more curious than anything. We had sex one night after hanging out and he screamed my name when he came. Our "relationship" was a bit rocky after that. We decided to be friends but I was going through a lot at the time and didn't realize I was confusing lust for emotion. He had absolutely no respect for me and was completely self absorbed; it's too bad I only realized this after the fact. We attempted to stay friends but neither of us has reached out to one another in months.

The German Soldier
I initiated conversation with him at a show. He looked like a German soldier, worked at a hotel and was in a band. We met up for coffee and he invited me over for tea and a walk in the park a week later; how romantic! We made plans to go to the Symphony a month in advance. He texted me drunkenly one night asking to fool around. I felt a bit pressured to invite him over since he was taking me to the Symphony. Although we had good chemistry otherwise, we had the worst sex of my life. A day before he was supposed to take me to the Symphony, he canceled due to work but said he'd be in touch. I never heard from again.

Kinky Online Paul
Around the same time that I had met the second stupid engineer, Paul and I started chatting over a mutual interest in a MMW threesome. After talking for a week, we met up for a bike ride and had a few beers. I invited him over that night and we had incredibly passionate and kinky sex. We saw each other once or twice a week and became really great friends with benefits. This went on for months until I met my boyfriend.

Last, But Not Least
I went home for a few weeks during my winter break. My friend and I went to a huge party in downtown LA. As soon as I met him, we were infused in conversation and spent the rest of the party together, mostly making out and him fingering me on someone's car. He gave me and my friend a ride home and asked to see me the next evening. We had insane chemistry and the sex was absolutely mind-blowing. We spent the next 48 hours together and he drove me to the airport when I had to fly back to school. We've fallen in love since. The distance is hard, but I believe when you find something this good, you have to hold onto it. I am 22-years-old.