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Sex Lives: Someone Who Really Likes Leather Boots

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Sam, 24, talked to GQ about sexting, long-distance relationships, and wanting to have a threesome. 

Sex Lives Someone Who Really Likes Leather Boots

Illustration by Rob Vargas

Sex Lives chronicles the evolution of one person’s sexual history. This week: Sam in Los Angeles, 24, who is bisexual and genderqueer.

The first thing I remember feeling aroused by was probably leather, specifically leather boots. I remember being really young and seeing a lot of women wear leather boots and feeling turned on by it, and I really didn’t know what it meant. I also felt kind of self conscious about it at the same time because I think my parents picked up on it, or at least my mom did. My memory is a little fuzzy, but I just remember feeling like as I got older and grew more into my sexual maturity that my interest in leather and leather boots became more apparent. It kind of played into my gender as well, like feeling aroused by women wearing those boots—and also low-key also kind of wanting to be wearing those boots. Recently, I got a pair of actual knee high leather boots. I don’t know exactly what about it arouses me, but it’s the first thing I remember.

I remember the moment I developed sexual attraction towards men was at summer camp— it’s always at summer camp! The summer before seventh grade I went to a sports camp and there was a talent show and at one point all the male staff members and counselors lined up in a row and they were wearing these long sleeve shirts rolled up and unbuttoned and they were doing a can-can dance or something and I just remember staring a little too long at one of the staff member’s chests and feeling my hormones bubble a bit. I also had a counselor that summer named Grant, who was this hunky tall glass of Pellegrino. He was like really Christian, always had his shirt off and a cross necklace, and he played guitar. I think he was also part of that sexual awakening. I hadn’t really come to terms with sex in general at that point; I was definitely horny, but I was just very self-concious about acting on it. The following summer, I was at a different camp, a Jewish sleep-away camp, and that was the summer where I feel like the horniness reached its peak. After I got back from camp that year was the first time I masturbated and it was to—this is so funny just thinking about it—the music video for “This Love” by Maroon 5.

Around ninth grade I started watching gay porn.  But the end of high school was when I finally discovered or really came to terms with the term bisexual, and at first it was a little bit like, “Okay, this makes sense. But now how do I tell people about it? And what am I going to do if they react poorly?” So the first person I told randomly was my pediatrician. I was doing a check up for college and he was like “Is there anything else I need to know?” and I was like “Yeah, I’m bisexual.” And he was like “Ok.” I think he didn’t know how to respond. The reason why I told him was because I had literally no knowledge of how to deal with sexual encounters with men. I was very naive about everything and I thought he’d be a good voice of reason for that. But he did nothing. After that I told my therapist, and she was really validating about it. And then I told a friend of mine, who I knew was bi and I felt like I could trust her. So I came out to her and of course, she was very validating to. And then beginning of college was when I finally just embraced that label and started to tell people I was bisexual.

I actually had sex with a man before a woman, which was really hard for me to digest at first because I was still dealing with a lot of insecurity around my masculinity.

His name was Mike and he was a musical theater major, so you know, very horny, vaguely sociopathic. He was a fun lay, but when we first had sex it was difficult. I think I was just very self-concious. It was a chaotic night, too, because my roommate was extremely drunk in the room upstairs and just vomiting a bunch. It wasn’t a great first time, but it wasn’t terrible. That was my first semester of college, and then the next semester I started dating a girl named Eliza. We started hooking up at the beginning of the year and then we were dating and then we had sex for the first time on Valentine’s Day. That was also a little difficult; the big thing was I had a lot of trouble finishing. That’s something I’ve still kind of struggled with, mostly when it’s the first time with someone. After that I had sex again a few times with Eliza and it was easier and better, and then she and I broke up and I went back to Mike.

I haven’t had a lot of great sexual experiences with men, but the one really memorable one was a guy who was a year older than me, but we’d been in similar social circles and I saw him around campus a few times and at parties. Gorgeous face, beautiful blue eyes, tall, built and gay. We matched on Tinder one night and I asked him to come over and he did and we didn’t even have penetrative sex, we just made out a lot and he jerked me off and made me come and it was really hot. That was the only time we ever hooked up, but it’s still something I remember quite vividly. 

Recently with my current partner, Katie, we’ve been long distance. I just visited her in New York and the last time I visited was particularly hot because it felt a little more spontaneous. There wasn’t much foreplay, I just put my dick in without lube. I guess I characterize that as especially hot purely because I think I’ve often had difficulty with sex. And it’s nice, it’s very refreshing and erotic when there’s ease to it. When I don’t feel like I have to try so hard. I think that can be said for any of the times that I’ve had really hot sex with someone—it’s always been hot not just because of the enjoyment but the ease of it.

I was in New York a couple summers ago and it was going to be like my hot, sexy summer in my mind, but it really wasn’t. I did hook up with a few people but it wasn’t as ideal as I wanted it to be. But there was a guy, Jack, who is actually a pretty prominent Twitter person and activist and he was working right near where I was staying and I think the proximity just made me bold, so I DMed him once at the beginning of the summer and we started chatting and it was pretty flirty. He was sending emoticons—not just emojis—emoticons, okay? We finally make time to get coffee and it’s really nice and then later in the evening I’m at a rooftop party in Bushwick and I get a text. He was like “It’s nice meeting you today,” and I was like “Likewise,” and he was like “I really like how hairy your legs are.” And then it sort of started to get into sexting. It was my first time sexting and I was a bit nervous about sharing nudes, but I was like, “You know what? I’m just gonna do it.” So he sent me a pic, and of course his dick looks amazing. We saw each other one more time at the end of the summer after like two months, but that was it. 

He and I have the same last name but it’s a pretty common name— we’re not related. So I’m back at school after that summer and we start to sext again and he was like “We didn’t really talk about this but I’m into doing younger/older brother role play.” That was not something I wanted to do. I shut that down, but then the next time he sort of brought it up again, he was like “Hi, fellow [Last Name].” And I was like “Oh my god, this is so perverted.” After that, I didn’t engage further.

Fantasy-wise, I definitely want to have a threesome. My partner and I are ethically nonmongamous, just because the distance and we both love each other and care about each other and want the other person to be sexually fulfilled. I hooked up with a guy recently and I told Katie, my partner, about him. She was very, very into it. I also told him about my agreement with Katie and he was also very ok with that. And Katie actually wants to have a threesome with me and this guy, but I’m not excited about the idea as much. But maybe I’m feeling a little cautious about it because of the potential for what can happen, just based on what I’ve heard from other people having threesomes. A lot of people say it’s not as exciting as you might think. It’s just very new to me because I’m already in such new stage of my sexual development with this long distance relationship that’s also open. It’s all new to me, but very exciting. I feel like I compartmentalize things a lot, especially when it comes to relationships. It makes me feel grounded and in control; I like routines. I’m autistic, so having that disability just makes me think about things in a certain way. I think I get a little bit frazzled and flustered when I have to readjust. I feel like there’s been a lot of readjusting with our relationship, but I think in a good way. She’s very gentle and patient with me; I came out to her as autistic the last time I visited her and she was very validating about that.

I was diagnosed with PDD-NOS as a child, which was in the DSM and is no longer there, but essentially it was considered a mild form of autism. I had a lot of early intervention. I received a lot of intense speech and language therapy throughout my childhood. That definitely helped me manage my autism, but I think I still harbored a certain resistance to certain things—especially systems that were very rigid and very binary. I feel like in that way my autism does play into my bisexuality, and I think I can also say that about my gender too. I’m in a really interesting place where I’m really questioning how I identify; I feel like I have been suppressing a lot of my femininity over time and I’m starting to really embrace it now and feel validated by other people, not just myself. Katie has been really helpful in that regard, her both being a sex therapist herself and just someone who I can talk to about really anything. I mean my autism has informed every aspect of my life, but my sexuality and gender in particular.

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