Love & Sex

Everyone I’ve Ever Had Sex With: Male, 28, Orlando

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"This list is not done."

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Summer Camp
The first time I touched someone else I was at an all-girl summer camp. We were both 13 and snuck off to an empty cabin during lunch. She was dirty blonde, with a cute smile, and always wore pink. We had no idea what we were doing while we went down on each other and kissed way too much. So much that my lips started to get puffy and hurt. I made her come with my fingers and tongue, which was exhilarating, but afterwards I started to feel weird and asked her to stop touching me. We tried a few more times before camp ended. I never finished but she always did.

Car Sex
At 15 I was at a concert and a dude hit on me. I laughed, because at the time I still looked like a woman dressed in men’s clothes. I was apprehensive, but after a few dates, we hooked up in a dark park in the back of his Honda Accord. It was strange, short, and totally unprotected. I remember the first penetration felt extremely invasive. He gave me my first orgasm in a pool.

I spent five years on and off with him, having “heterosexual” sex that was really the gayest intercourse I have ever been part of. When I told him I thought I was a trans man, he asked me to wear more feminine clothing, I complied because neither of us wanted anyone to know. Meanwhile, I was doing him with a prosthetic dick (strap-on) every other night. I spent years after our break-up trying to convince everyone how truly closeted he always was – even though I still wasn’t out myself. 

First Time Cheating
At 17, I was dating that guy while working at the same summer camp. I met a woman who was six years older than me and covered in tattoos.  She was trashy, but commanding, which I found extremely appealing. We had sex in the cabin she led while the camper’s slept. She never asked permission for anything and took what she wanted from me without words. I was never sure if it was the domination or the taboo circumstances that turned me on so much. My favorite thing about sleeping with her was that she never gave me time to feel uncomfortable about my body. We never talked much after that summer. The girl I had hooked-up with when I was 13 was working that summer as well and she gave me the cold shoulder for a long time. 

Second Time Cheating
I was almost 18 and he looked like a 23-year-old Brad Pitt with a little less muscle. He was branded with a gang mark and had just gotten out of prison. 17-year-old me thought that was super hot and did him on my cousin’s living room floor without a condom. It was among the worst and shortest sex I’ve ever had. We didn’t even get undressed. Just pants unzipped and underwear to the side. I didn’t come and ended up getting an STD that made my downstairs feel like an itchy rock, three cheers for chlamydia! 

First Threesome
Desperate to get out of my parents’ house I moved in with car sex guy. I was very open about my attraction to women. We had both decided labeling myself as a bisexual female was easiest for everyone even though I was pretty sure I was a guy. The girl I had slept with at 13 (my first sexual experience) came to visit and on the first night we all had sex. I had imagined a threesome would be messy and awkward but I found it extremely sensual. Everything flowed. After a few weeks of continued threesome action, it was apparent they were both feeling some strangeness about sharing me. She asked me to leave with her, and when I declined, she admitted she had never gotten over me sleeping with the other women at camp and would never forgive me for not coming with her. 

Speaking Spanish
After moving away for college, and breaking-up with the guy I was living with, I met a feminine Puerto Rican girl whose name I could hardly pronounce. She spoke just enough English to order food at a restaurant. She loved to walk around naked, which was exciting, until it got boring. I’ve always felt like nudity can get really boring. She fell for me too hard, too quickly, which I found unattractive. By far the loudest girl I have ever slept with. My neighbors tried to get me evicted because of her screaming.

Our sex was very one-sided because I found the idea of her trying to get me off repulsive. It was never her fault and she didn’t understand why I didn’t want her to touch me, but discussing it was not an option due to the language barrier. I was never able to articulate to her why I wanted to break-up and I think my poor Spanish made her think I thought she didn’t wash enough, which I have always felt badly about.

Truck Hand Job
I was driving home from class one day when a dude in a red truck flagged me down saying there was something wrong with my car. My apartment building was right up ahead, so I pulled in and he pulled in next to me. He rolled down his window and said, “there’s nothing wrong with your car — I just want to get in your pants.” I told him I appreciated his honesty.

After a few minutes he persuaded me to get into his truck with him. He was built and super sexy. His windows were tinted and rolled-up. He could have murdered me and no one would have ever known — something about that turned me on. He whipped out the biggest erect cock I have ever touched and asked me if I would stroke him. I did, and after only a few minutes, he came all over my hand. He kept asking if he could return the favor, he never forced himself on me, but for some reason I felt empowered just walking away after making him come. He asked for my information so he could take me on a date, but I declined. He drove away. No name, no number, nothing. 

First Online Hook-up
I met a girl on a dating website who was a few years younger than me and super feminine. One night I picked her up from in front of her apartment building and took her back to my apartment. I knew as soon as I saw her I wasn’t attracted to her. To escape the situation, I went down on her as soon as I got her back to my place. She wasn’t very clean and kept screaming my birth name (a female name that I have never been fond of). My skin was crawling by the time she came. She begged to stay over. Before I dropped her off, I asked her where the nearest Taco Bell was. She asked if she could come too. I didn’t answer and proceeded to drop her off in front at her (her parent’s) apartment. Not even a grilled stuffed burrito cleansed the weirdness of that encounter from my palate. She called and emailed a lot afterwards. I never replied. 

Her First Time
At 19, I was single and a friend from summer camp called me out of the blue asking me very bluntly if, as a friend, I would take her virginity. I agreed, and when she arrived to stay the weekend in her huge truck and baggy pants, I decided I would let her top me. I hadn’t let a girl get me off since the trashy woman at camp, but something about their masculinity turned me into a mushy puddle, which was weird since the majority of the time, I topped the girls I was with. It was a bit awkward and she laughed a lot. Typically I think a little laughter is great — it gets you through the weird parts of sex, but her constant giggling killed the mood for me. Still, she gave it her all, but was too fast due to inexperience. Her confidence came off as counterfeit, which was a turn-off. She tried wearing a strap-on, but couldn’t understand the dynamics. I tried to top her, but she became a motionless statue.

Second Online Hook-up
I met a dude online that was only a few blocks down from where I lived near the university. He was dull and to this day, I can’t even remember his name. After a night full of drinking and dancing, I messaged him and because he didn’t have a car, picked him up off the curb in front of his dorm and took him back to my apartment. He brought his own condom, which was pleasant of him. He asked to use my computer and porn came up automatically in the browser (sorry, not sorry) so we watched it together for a while before we got down to it. Our sexual chemistry was awful and it was probably the quietest sex I have ever had. 

The Wrestler
We met online and he was the dumbest person I’ve ever slept with. We never had anything to talk about even though we were regular fuck buddies for six months. He was hot and I sort of knew he had a significant other already that wouldn’t fuck him, but we never talked about it. Every time we fucked we had anal sex, which wasn’t new to me, but it was the first time I was able to really relax and receive. I think it was because there wasn’t any real pressure from him to use my other hole or take my shirt off, like there was with the other guys. He was very pleased to just have my ass and he knew how to use lube, which I figured out quickly was extremely important. On one occasion when he was in my other hole, the condom broke and I ended up at Planned Parenthood to the tune of $80 for the morning-after pill. I decided after that I was going to take a break from men. 

Meow in Wonderland
Met a super feminine fashion student at school and took her on a few dates. She worked at Starbucks and gave me crap about not understanding the correct way to order and not accessorizing my outfits enough. She was really cute and we fucked a few times. It was always slow and she had no interest in getting me off. Which was cool because it let me off the hook so I didn’t have to try and explain why I didn’t want to be sexually touched. 

The Last Time
Out of no where, car sex guy came back into my life. (Honda Accord, not red truck.) We went out to dinner in an attempt to patch things up between us, but it became clear to me pretty quickly we no longer had anything to talk about. We went back to my place and had hateful rough sex. It was my first experience being hit repeatedly during intercourse. We choked, smacked, and ripped each other apart. There was real hate going on that was spiraling into intense sexual pleasure. I was bruised for weeks and so was he. We both came so hard we couldn’t breathe. 

Side note: other sexual acts attempted with car sex guy in those five years include: water sports (no thanks), lots of role playing, first time anal (horrible the first time, I wanted to die, but it got better), recording a sex tape (I hope somewhere that tape is broken into a thousand pieces), wearing a prosthetic dick (always and forever), giving a rim job (the first time he begged me to stop for the first few seconds, then was having such a good time, he was speechless.) He’s also the only guy I have ever swallowed for. Not sure if I would ever do it again.

The Dancer
She was younger than me, but I saw a sexual innocence in her that some part of me desperately wanted to destroy. I was in my junior year of college. I got her off the first time without even taking off her clothes. She was inexperienced putty in my hands and I loved it. I wanted to mold her. We moved in together after a year and I came clean about being a trans guy when she confronted me about our one-sided sex. She stayed with me even though I was still afraid to come out. In the meantime, she had a fine time experiencing multiple orgasms, BDSM submission, and anal sex for the first time. 

Sort of a Foursome
While super high and perhaps tripping just a little, we had sex next to two dude friends. The one bisexual guy kept reaching over and touching us. We kissed but never touch genitals with the other couple. 

Shrooming
Tripping hard on shrooms, the dancer and I hooked-up with a friend of ours. She was tall and blonde. I watched them go at it for a while and fucked them both with my prosthetic, making them come back to back. Sex while tripping is trippy, to say the least. We hooked-up again not tripping and it wasn’t quite as exciting. 

Not Bisexual
We met up with a friend at a theme park, and throughout the day, got to talking about how although everyone thought he was gay, he was really bisexual. Later that day we decided to give him an opportunity to prove it and got a hotel room. He had a hard time getting it up to fuck my girlfriend, and although I desperately wanted to top him, I jerked off instead while I watched them. No one came. It was sort of sad and silly. 

Hey, Dude
Super high at a party in our apartment complex, an acquaintance asked if he could come home with us to have a threesome. We laughed it off, assuming he would want to fuck both of us as women, which was out of the question. A few minutes after we got home, he knocked on our door, came in, and took his clothes off. I hadn’t had a dick in my mouth for years and I think seeing me enjoy myself doing it confused my female partner, who assumed being a trans guy meant only being into women.

My willingness to go down on him surprised me too. I wasn’t fully convinced other bisexual trans men even existed, and didn’t want to lose the respect of my female partner as a top. When he touched me, I wiggled away and put the attention on her. He started to fuck her, without a condom, which pissed me off. By the time I found one to give him, he had whisky dick and asked if I would fuck him in the ass instead. It was a pleasant surprise and I was eager to oblige. I put on my prosthetic, but he was a novice bottom at best and couldn’t relax no matter how much lube I used. I don’t remember if anyone came, but I know the next day I kept telling her how drunk I was and that under normal circumstances I would have never given him head.

First Foursome
We hooked-up with a “lesbian” townie couple one New Years, under the influence of way too much vodka. They were okay but certainly not among the most attractive people I have ever slept with. I say “lesbian” couple because after that night, one of them came out as a trans guy, which was a random coincidence. I never came out to him, and when we had sex, I told him not to touch me, but again, I’m just a mess for masculinity and I let him for a little while the girls fucked each other. I think about that other trans guy often and how I wish I would have taken the time to talk with him about how I was feeling. I was too scared then to be honest with anyone, including myself.

Strange Pairing
We laid dormant for a while, only fucking each other, then a few years later, the friend who asked me to take her virginity came for a visit and we all three ended up fucking. She had gotten better and although, again, I was very opposed to it at first, I let her take some control with me. It was the first time I ever squirted during sex. It felt good to have the experience of ejaculation, but still very weird. That strange grossness and guilt I always felt when I used certain parts of my body crept in. We paired off, which was very new to us. I let her fuck my girlfriend while I wasn’t there and we fucked alone. Just once. 

The Straight Couple
We made friends with a straight couple and slept with them one night. I watched the guy fuck my girlfriend, while I fucked his girlfriend. He went down on me for a little while and wasn’t too bad at it, but I felt really uncomfortable and stopped it. I never touched him. He lied about wearing a condom and his girlfriend kept saying his name while I went down on her. It was super weird. After they broke up, the girlfriend came to our place wanting to hook-up with us alone. It was alright, but sort of strange because she had no idea what she was doing when it came to getting a female-bodied person to orgasm. 

The Honeymoon
In my mid-20s, I married my girlfriend, but that didn’t stop us from continuing our sexual experiments. Part of the reason I married her was because this was the sort of thing we both enjoyed. We found a girl while we were honeymooning the Keys and went back to her super fancy "clothing optional" hotel. I wasn’t too keen on getting naked, but figured YOLO or whatever and jumped into the hot tub with the girls in the buff. I watched them kiss and mess around while I drank. We went back to her room, smoked weed, and I fucked them both til they came. She tried to touch me, but my wife redirected her. My wife was a pro at that and I love her for it. We found out later after friending her on Facebook that she was a Republican. Random hook-ups sort of lost their fun after that.

Kindred Spirits
Less than a year later, I came out as a trans man. I was done living a lie and pretending to be female. When I started transitioning to male, I met another guy at a support meeting. We hit it off and my wife and I started plotting out our moves to hook-up with him. I found out he had never been with another guy before and this would be my first sexual experience with a guy who knew I was male. Drunk at a house party, we ended up in a room with him and his ex-girlfriend. Too timid to touch each other or make a wrong move, we fucked the girls and they fucked each other.

It took three more times of us all sleeping together for us to do more than kiss. We went off by ourselves one night and screwed like animals on the living room couch. We fucked so hard we both bled. It was painful and freeing. A year later, we’ve figured things out a bit more. We’re currently in a triad relationship. My wife, him, and myself. We all have regular sex paired-off and with all three of us. There’s no jealousy and so far, everything is wonderful. I have never been happier. As sexually fulfilled as I am, there is talk about opening up the relationship to have more experiences. Not emotional, but sexual, relationships. I feel good and prepared for that. I’m not sure where, how, or when that will start, but I’m ready to make up for lost time. 

I'm married and super partnered to one woman and one man who I adore, but this list is not done.