My First Time

My First Time: Male, 19, Florida

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We’re looking for stories about the first time you had sex. Email  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.) Submissions may be edited.

Girls hadn’t particularly liked me during high school, so it was a big surprise when girls started flirting with me at college campus events or after classes.  I was — gasp — actually attractive.  I went on dates.  I had my first real kiss on one of those little dorm beds, the twin-sized ones that make it impossible to move around without elbowing your partner somewhere painful.  I wasn’t complaining.  Still, I turned down offers from several co-eds who wanted to “go further” during hook-up sessions. I had always wanted my first time to be with someone special, with someone I loved.

My search for a romantic partner went nowhere, and I was in a rough place at the end of my freshman year of college.  I was fighting with my parents more often,  my best friend and I were growing apart, my grades had begun to slip from too many late nights at the club, and my sense of personal morality (especially towards sex) was in turmoil.  So, being the frustrated, hormonal, extremely horny nineteen year old that I was, I focused on the sex problem.

I started wondering why I held onto my v-card for so long, despite the opportunities to lose it.  I spoke to one of my friends about it, and she encouraged me to “just get it over with” so that I would gain experience and know what I was doing for the future. When I start dating someone seriously, I reasoned to myself, I want to be able to please them.

That was an excuse. In reality, I was feeling lonely, and I wanted to sleep with someone to fill the void.  For the record, I don’t recommend that course of action to anyone.

I eventually heard about a party taking place at a resort close to where I was living. This was the first time I had ever heard of “swingers.”  Swingers are sexual polygamists — single or married, they typically have sex with other single or married people. The party they were holding was clothing-optional, with “playtime” to take place later in the night.

So, in the spirit of losing my pesky virginity and “gaining experience,” I went to an orgy.

It was absolutely one of the worst ways to lose my virginity that I could have dreamed up.  I was easily the youngest person there by 20 years.  I remember sipping a mixed drink and making idle conversation with another single guy three times my age.  He talked to me about his daughter and how she was doing well in middle school.  If she could see you now, I thought. I wandered away and talked to a married couple lounging in the buff near the poolside cocktail bar. They were fat and boring and ugly.  I was baffled.  I could not imagine a future where I was okay with the prospect of my spouse sleeping with another man or another woman.

I was not attracted to any of the party-goers. Halfway through the night, my brain started telling me to just get out of there. Find a mall to hang around, go see a movie, phone a friend. Don’t stay here. Nothing good is going to happen.

I made myself see things through.  I just wanted to get things over with and move on with my life.

Eventually, people started screwing each other.  Some retreated to guest rooms or private Jacuzzis. Others started going at it out in the open.  My new friend with the young daughter stuck it to a woman in the shallow end of the complex’s pool. Another woman demonstrated remarkable flexibility on the dance floor while alternating her attentions between two guys.

The best way I can describe my state of mind: I was in a daze.  I kept wondering what the hell I was doing there.  I wandered over to one of the private rooms. An enormously obese woman was sprawled on a bed in the center of the room, surrounded by a crowd of men.  I didn’t know her name, but she saw me and beckoned me forward. I figured what the hell and stood in front of her.  I knew what I was supposed to be doing.  It was very mechanical.  Step forward.  Check. Grab penis. Check.  Insert penis into vagina. Che—.  She was very flabby. I had a hard time getting inside while navigating around her rolls of fat. Wasn’t I supposed to be enjoying this?

Anyway, the actual sex lasted about ten seconds. I had half a second of pleasure as I orgasmed before stepping away. Just like that, I was no longer a virgin. I walked out of the room, found my clothes, and retreated to my car, never looking back. The ride home was a blur.

I will regret that night for the rest of my life. I wish I had waited and kept my virginity a while longer.

I want you to understand that in no way, shape, or form am I insinuating that swingers are horrible people, or that their lifestyle is wrong.  Sex means something different to every person. Some people are perfectly content having sex with strangers, more power to them.

However, a year after my virginity escapade, I had sex with someone I genuinely loved, and it was a wonderful experience. I can now speak from both sides of the issue. In my personal opinion, having sex with someone you really care about is the best way to go about things. It gives you an opportunity to connect on a personal level, and share every intimate part of yourself with someone you treasure, someone you know will value the gift you are giving them. Do not have sex because you are feeling lonely or want to get your virginity out of the way. Do it because it means something.  It’s a hell of a lot more fun that way.


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