"I was always in fear of his female housemate coming home early…"
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My first. I met him online; I was a twenty-one-year-old virgin and he was a handsome, twenty-five-year-old med student doing a year of research in my city. I didn't even tell him I was a virgin, though the blood on the sheets said it all for me. He became more of a regular fuck-buddy than boyfriend (he was moving away in a year) and we would hang out and then bang all over his apartment. I was always in fear of his female housemate coming home early and finding us doggie-style on her couch… or her bathroom sink, or the floor, or almost everywhere except the bed. This ended when he returned to med school on the east coast. I was desolate for a few weeks, until I found…
The sexiest man I've ever slept with. He was smart, movie-star attractive, and amazing in the sack. On our first date we felt the chemistry and he just went down south without any warning — it was incredible. Still the only man I've been with who has ever enjoyed giving as much as taking, and damn was he good at it. The only downside was how hard I had to convince him to wear a condom. "I'm sterile!" he tried to tell me — don't worry, I made him wrap it up anyways. He wasn't looking for anything serious and I wasn't either, so I enjoyed the incredible sex while it lasted.
Anthony is a good friend of mine. We had a love-hate friendship for a year before having sex. He was a Texas transplant to Southern California, and our worldviews were almost polar opposites. I was anti-gun at the time, and he owned an AK-47. We could relax around each other usually only after smoking a bowl or two. We didn't actually consummate our mutual attraction until his last night in California — he'd decided to move back to San Antonio. We'd gone out clubbing with a group of friends and we decided to leave early and go to my place to do it. He drove. Probably the worse sex I've ever had. It was after a night of drinking so he had trouble keeping it up. He also wanted me to go down on him without any reciprocation, and I refused. Then he got mad and left me stranded at my apartment, since I had left my car at my friend's place. I was so angry and sexually frustrated that I rode my bike three miles at four a.m. to get my car back. I didn't talk to Anthony for a few months, but we eventually started texting and talking again and are closer than ever. We do have a flirty friendship and he has hinted about getting together again sexually when he visits, but since I've been in relationships, he hasn't yet had a chance to redeem himself.
A twenty-seven-year-old undergrad at my college. I wasn't really attracted to him, but I got really drunk on our second date, which led to having crazy drunk sex in his apartment. I was also dating Amir when I met Sam, so as that relationship became more serious, Sam and I ended up just friends. When I broke up with Amir, we slept together again, for the last time. We're still good buddies and hang out and drink often. He's now about to get married and have a baby.
My first real boyfriend was also a total sociopath and crazy motherfucker. We had a tumultuous relationship that lasted for about six months, during which he cheated on me multiple times. He also gave me my first orgasm through intercourse, so it wasn't all horrible. He was incredibly handsome, but dumb as a rock. When I finally dumped him for the last time (a very dramatic scene), he tried to threaten me and call the police with some BS story about me having my brothers beat him up. I ended up seeking a restraining order and had a very stressful time recovering from the breakup. As I was getting my restraining order, I found out his other ex-girlfriend also had one on him — and I learned how lucky I was to end it when I did. I learned a lot about red flags after dating him.
I met him, through Sam, at a bar. That should've been a red flag since he's turned out to be an alcoholic. This was a rebound relationship, as we met only a month after I dumped Amir. He had a very large penis but had difficulty finishing (something he blamed on his masturbation "addiction") which made sex less fun for me. A two-time Iraq War vet, he was also a super-jealous and possessive boyfriend who had trouble getting over the fact that Sam and I had slept together. In addition to suffering from PTSD and depression, he was also very stubborn and constantly made misogynistic and racist remarks. I almost broke up with him several times in only four months. But I had trouble letting go of seeing him not for who he was but who he could have been. A month after we finally broke up, he wanted to try to be "friends" and I was willing to give it a go. After hanging out a few times, he told me that he "still loved me" and we had sex. But when I finally told him I still had feelings for him, he responded with, "I thought we were just having fun," and asked, "Can I say no to being boyfriend/girlfriend but still hang out with you every weekend?" I told him no, and that was the last time we spoke. I haven't had sex since, but it's getting to be about time. Boys beware.