Sex Lives: Someone Who Really Loves Leather Boots


His name was Mike and he was a musical theater student, so you know, very excited, vaguely sociopathic. He was a fun layman, but the first time we had sex it was hard. I think I was just very embarrassed. It was also a chaotic night, because my roommate was extremely drunk in the upstairs bedroom and was throwing up a bunch. It wasn’t a great first time, but it wasn’t terrible. It was my first semester in college, and then the next semester I started dating a girl named Eliza. We started dating at the beginning of the year, then we went out together, then we had sex for the first time on Valentine’s Day. It was also a bit difficult; the big problem is that I had a lot of trouble finishing. It’s something I still struggle with, especially when it’s the first time with someone. After that I had sex with Eliza several times and it was easier and better, then she and I broke up and I went back to Mike.

I haven’t had many good sexual experiences with men, but the one that really stood out to me was a guy who was a year older than me, but we had been in similar social circles and I saw him on campus a few times and at parties. Magnificent face, beautiful blue eyes, tall, built and cheerful. We met on Tinder one night and I asked him to come over and he did and we didn’t even have penetrative sex we just kissed a lot and he jerked me off and fucked me made her cum and it was really hot. It was the only time we met, but it’s still something I remember very well.

Recently, with my current partner, Katie, we traveled long distances. I just visited him in New York and the last time I visited him was particularly hot because it was a little more spontaneous. There wasn’t much foreplay, I just put my dick on without lube. I guess I call this particularly hot simply because I think I often struggled with sex. And it’s pleasant, it’s very refreshing and erotic when it’s easy. When I don’t feel compelled to try so hard. I think that can be said for all the times I’ve had really hot sex with someone – it’s always been hot not only because of the pleasure but also the ease.

I was in New York a few summers ago and it was going to be like my hot, sexy summer in my mind, but it really wasn’t. I met a few people, but it wasn’t as ideal as I wanted it to be. But there was a guy, Jack, who’s actually a pretty big Twitter person and activist and he was working right next door to me and I think the proximity made me bold so I sent him a times in early summer and we started chatting and it was pretty naughty. He was sending emoticons – not just emoticons – emoticons, okay? We finally make time for coffee and it’s really nice and then later that night I’m at a rooftop party in Bushwick and get a text. He was like, “It’s nice to meet you today,” and I was like, “As well,” and he was like, “I really like how hairy your legs are.” And then it kind of started to get into sexting. It was my first time sexting and I was a little nervous about sharing nudes, but I was like, “You know what? I’ll just do it. So he sent me a picture, and of course his dick looks amazing. We saw each other once again at the end of the summer after about two months, but that was it.


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