by Everett


Gender: Bigender (male assigned at birth)
Age: 28
Race/ethnicity: White
Current location: Boston, MA
Highest education received: Post-graduate degree (currently pursuing)
Occupation: Web development
Relationship status: Single
Religious affiliation: United Methodist
How religious are you? Somewhat
Any other term(s) that describe your sexual orientation/sexuality better/best? Attracted to women regardless of gender presentation
How many sexual partners have you had in your life (including oral sex)? 12
How many hookup stories have you here posted before? 2


My First Random Hookup


How long ago did this hookup happen? 2 years ago

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? My distance girlfriend of a year had been giving me the cold shoulder for several weeks – I would go and visit her almost every weekend but it was becoming obvious that she wasn’t interested anymore – and the past several weeks she had asked me not to go out there (claimed it was because she was busy and stressed out, but I later found out she was seeing another guy… she ended it a few days later). After one Friday’s shout-by-phone match where she succeeded in confirming that her and I were all but done, and I was pissed off and wanting a drink… A few hours later, I took a ride down to an Irish pub up the road, grabbed myself a beer and then heard “R” literally beckoning me over to her and her friend. “R” was a shorter, Latina gal, kind of curvy, with curly auburn hair — cute. She was very forward, said she thought I was cute and we should hang out… so we did.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I told her right off the bat about my soon-to-be ex, she genuinely felt sorry and told me I deserved better. We talked for several hours over several drinks and by time 1 or 2 in the morning rolled around we were were all over each other. She asked if I was okay to drive and if I lived alone, yes on both counts, so I paid the tab and we both bolted.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? There was no question as to what we were heading back to my place for, I’m pretty sure we were both naked within 30 seconds. I was fairly drunk, too drunk to be on top, so she just rode me and orgasmed several times. We then kissed and she fell asleep next to me

Did you have an orgasm? Did your partner(s)? I did not, she had several.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condoms, she also mentioned being on the pill.

What were your REASONS for having this hookup? Upset, lonely, horny, and the opportunity presented itself.

Were alcohol or drugs involved? If so, how much? Alcohol… lots.

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? When we woke up, neither of us had hangovers. We chatted for a little bit over coffee when I learn that she was 20 years my senior and had a 14 year old daughter. Not what I was expected, she certainly didn’t look 45. I drove her home, we exchanged numbers and she told me she’d love to get together again some time. We did meet up at another bar a week later, and she spent another night with me, no sex this time but lots of cuddling. Honestly, she seemed like a nice person but I just wasn’t that into her unless I was drunk, and that isn’t the reason I want to be with somebody.

To whom did you talk about the hookup? How did they react? A few fraternity brothers, they all said it was messed up but cool.

Was this a consensual and/or wanted experience for you? For your partner? Yes on both parts

Do you regret this hookup? If so, why? Yes, because my ex and I were still technically together at the time, even though it was a forgone conclusion at that point we were breaking up. (I told her the next day what happened and she didn’t even care.)

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? It was a bit of an ego boost, but I really wasn’t that in to her once the alcohol wore off. There’s nothing wrong with a casual hookup but I generally prefer to sleep with people I’m genuinely interested in – it was sex and nothing more I guess.

All things considered, how POSITIVE was this experience? A little positive

All things considered, how NEGATIVE was this experience? Somewhat negative

Anything else you want to add about this hookup or anything else? Nope

You have a hookup story to share? Submit it here!

Story Views: 454