Location: Boston, Ma
Highest education received: Some college (currently in college)
Religious affiliation: Grew up Protestant, but none at the moment.
How religious are you? A little
Sexual orientation: Mostly heterosexual
How many hookup stories have you here posted before? This is the first
The Guy with the Skulls
How long ago did this hookup happen? 3 months
How would you best classify this hookup? One-night stand
Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? I tried online dating for a while and I came across this guy who was 42. I thought he was attractive, but not extremely so. We agreed to meet at a fancy restaurant near my house (he didn’t know it was close by). I walked in and couldn’t believe my eyes! He was wearing a leather jacket and a scarf. He had a tattoo on one arm and there was an outline of a new tattoo on the other arm and he had these cool skulls bracelets (surprisingly nice). He was beyond attractive. There was something about him!
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The minute I saw him I knew I was going to have sex with him. He went to Afghanistan twice and he told me a few stories, but all I could hear was the wild sex we were going to have. We had to go to a different place because the restaurant was closing. At this bar a drunk gay guy approached and talked about the tattoo and wouldn’t go away. So I leaned in and got very close to him and he turned his head and kissed me as to hint that we were busy. The guy left and he gave me the most sensual kiss. We automatically knew what was coming next. We decided to go somewhere “private.” We ended up at a hotel.
What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I’m a hyper sexual person very comfortable with my sexuality and not shy about it. We closed the door and were ripping each other’s clothes off and I remember he had two skull tattoos near each hip bone. Soon after kissing desperately he started going down on me, then I gave him a quick blow job and we had sex for about 30 minutes and after a 20 minutes break we did it again. We mostly talked dirty to each other and after we laid down very close listening to each other’s heart beat and we fell asleep.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We didn’t use precautions and I’m on the pill.
What were your REASONS for having this hookup? I enjoy the thrill of flirting, seduction and the anticipation of making out with a person. He seemed like someone who would be able to keep up with me.
Were alcohol or drugs involved? If so, how much? We had a good amount of alcohol. Enough to be slightly drunk.
What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I went home in the morning, bravely while performing a walk of shame and we talked a few times and that was it. I panicked when I got home and remembered that we didn’t use a condom. I saw my life pass in front of me. But I was lucky enough to not have gotten anything. But I was and still am glad I had sex with this man. It was fun and a good story for my erotic memoir.
To whom did you talk about the hookup? How did they react? I told my two best friends. The girlfriend was shocked that I didn’t know him and sex with him anyway.
The guy friend thought it was a great story.
Was this a consensual and/or wanted experience for you? For your partner? Yes, it was very consensual.
Do you regret this hookup? If so, why? I don’t regret it.
What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The best part was being comfortable with someone just as sexual as me and that he wasn’t threatened by it.
I’ve learned to never have unprotected sex and to always bring a condom with me and not be afraid to ask for a guy to put one on.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? A little negative
What did you think about this story? Tell us in the comments – just be nice!
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