Whether it was in the back of a cramped car, with your pants at your ankles, or in your parent’s queen-sized bed, we want to hear about the first time you had sex. Email email@example.com with 500-1000 words. (Don’t worry, we won’t print your name — but please do make sure to include your gender, where you were, and how old you were.) Want more first times? Follow us on Facebook.
It was an early spring day. My big brother, actually my half-brother, was in town.
Earlier that day I played a rugby match. It was the best game of my life, sadly we lost. After the game I took my brother with me to a post-game party. We left early because we wanted to meet with a cousin. I am the younger of the three, my brother was in his early thirties, my cousin in his mid-thirties. I was 21.
After we got together we went to a bar, drank beer, ate buffalo wings, and we caught up with each other’s lives. Time passed, we visited a couple of other places before my brother decided it was time to take his little brother to a strip-club, so we headed to a strip-club that doubled as a brothel.
My brother knew I was a virgin, he always teased me about that. Sometimes he told me that I was a loser, that I was gay, other times he tried to help me with my pick-up and social skills.
In addition to being a virgin, I had never ever had a girlfriend. Not a lame middle-school relationship many people experience, not a high school girlfriend, nothing. I was always the guy who had really good female friends. Every single girl wondered why I didn’t have a girlfriend, yet nobody wanted to be my girlfriend. In retrospect I really had some issues to work out.
It wasn’t that I had never been presented with an opportunity to get laid before; however, the two times I had the chance, I never realized I had it, so I wasted those opportunities.
My cousin, on the other hand, ignored this fact. So my brother decided it was time for me to lose my virginity. I always knew that this was probably going to happen. I decided that I was okay with losing my virginity with a sex worker. I thought that love making is supposed to happen with someone special, but sex is another thing. My line of thought was as follows:
It is like eating. I can eat some tacos with someone else to relieve our hunger while we chat about the weather, or we could have an intimate talk while having a 5 course meal. Both scenarios will relieve our hunger, and they require the same actions: eating, talking. However, those are two completely different experiences.
I decided to try the tacos and leave the 5 course meal for later. My brother told me to pick one of the performers. Meanwhile a stripper started chatting with my cousin, she was offering her services to him, but he said that tonight was my night. He told her that I was a virgin (in his mind he was just kidding). She was willing to take on a newbie, plus her price was relatively cheap compared to other performers.
Before anything else, business was taken care of, so my cousin and brother split the fee and paid her. Before I knew it, I was on my way to the brothel part of the strip club. We went there, she took care of some fees, a guy gave her a condom, some baby wipes, and hand sanitizer. She took my hand and lead me to our room.
It was a little bit dark, she asked “Is it really your first time?”
“Yes,” I answered.
“I don’t know why you’ve never had sex before, you are not bad looking,” she replied. She gave me some baby wipes, hand sanitizer and told me to clean up. She did the same.
After we cleaned ourselves, she began undressing me, she took her top off, and told me that she was going to start kissing my body, that everything that I was going to feel is what a woman would feel. She kissed my chest while her hands caressed my skin. She then started sucking my nipples. It felt so damn good, she sent a shiver down my spine. Afterwards she told me to do the same to her, and gave me some pointers as I was doing it.
Later she took my pants off, and asked if I knew how to put on a condom. I told her that I knew, so she proceeded to put the condom on my penis without any tutorial. She then got on top of me while I was in between a sitting and laying down position, she started riding me, after some time, she got off and started giving me a blowjob. I was a little bit numb on sensation because of all the alcohol I had ingested through the night, so it took a little effort to cum. After the deed was done, she told me that it was good that I lasted that long, considering it was my first time. She gave me some pointers on grooming my pubic hair, and a couple more about kissing a woman’s body, and that was it.
I was, and still am, happy with my first sexual experience. It was very clean, very informative, it took a lot of pressure off my next couple of encounters. I tried what she told me to do and it worked. Today I don’t even remember what she looked like, but when I think about that night, I always think about that really nice, caring, beautiful woman that got me through my first time.
—Male, 21, Mexico