by Everett

Gender: Bigender (although at the time only identifying as male)
Age: 27
Race/ethnicity: White
Location: Upstate New York
Highest education received: Post-graduate degree (currently pursuing)
Occupation: Call Center Supervisor
Religious affiliation: United Methodist
How religious are you? Somewhat
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Attracted to women, regardless of my gender presentation or mood
How many hookup stories have you here posted before? 1

Fuck My Life… Or Fuck Me?

How long ago did this hookup happen? 4 years ago

How would you best classify this hookup? Fuck buddies

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? Back when I was between undergrad and graduate school I used to read and comment on the website FML (Fuck my Life) quite regularly. I was home for the holidays one year and a girl randomly sends me a private message, saying something to the effect of “hey, you live in Fredonia? So do I!” We messaged back and forth for awhile before moving to Skype. She was 18 and a townie (grew up in Fredonia), dirty blonde, petite, beautiful soulful hazel eyes, just all around really pretty. We really hit it off and despite the fact she had a boyfriend at the time (who lived in Kansas and treated her very badly, at least from what she told me) we talked about everything and anything for hours. I knew she was way too young for me to seriously consider dating her (I was 24) but when she started asking me about my sex life and what I enjoyed (I was going through a long period of being single) and teasing me a bit on cam, I was definitely turned on. She suggested we hang out when I got back to town, and I of course said yes.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I texted her when I got back to town a week later. She quickly replied suggesting she come over and “watch a movie.” I picked her up downtown and we headed back to my apartment. We put something on Netflix, we sat down on the couch together. I tried to hold her hand and she responded by wrapping both her arms around me and resting her head under my chin. The chemistry was magnetic, and the tension quickly became palpable. We gazed into each other’s eyes for a bit and then she looked down at my crotch, and said “looks like somebody’s excited to finally see me”  and started rubbing my cock through my jeans. I started running my fingers through her hair and she leaned in for a kiss. After a few minutes of making out (and she was an amazing kisser I might add) she suggested we go somewhere we could sprawl out a little more.

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? We headed upstairs to my bedroom, she mentioned she was on her period. Trying to be a gentleman, I suggested we just cuddle this time, and she said “hell no, I didn’t wait two weeks in anticipation for my period to stop me from fucking you”. What resulted was an amazing blowjob (she said I could return the favor next time) and my first experience with period sex, messy but felt incredible. Afterward we cuddled again and chatted for several more hours, before I dropped her off for work with a kiss.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We talked about our histories quite a bit, in addition to using condoms.

What were your REASONS for having this hookup? My first fiancée passed away a year prior and I hadn’t dated since then. For me, I was lonely, needing intimacy and very horny.

Were alcohol or drugs involved? If so, how much? No, we were both sober.

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? She texted me a few days later because she wanted to “fuck my brains out” again. We met up at my place again and we were naked within minutes, pretty much a repeat of the previous time, minus the period, and with the addition of anal.

The sex was amazing but I felt so guilty continuing to pursue things with her, one because my fiancée had died a year earlier and I didn’t believe I had any business pursuing anybody ever again, secondly because she had stated several times she wanted to be “fuck buddies”, wanting to eventually patch things up with her boyfriend in Kansas, and at the time the idea of casual sex didn’t sit well for me. I broke things off with her a few days later.

To whom did you talk about the hookup? How did they react? Nobody

Was this a consensual and/or wanted experience for you? For your partner? It was fully consensual, and I don’t think there was any question in our minds as to why we were getting together.

Do you regret this hookup? If so, why? At the time severely…. Catholic guilt (I’ve since left the Catholic Church). Today I only regret letting my guilt keep me from giving her more of a chance and breaking things off so abruptly. We had incredible chemistry and a lot of fun together. There wouldn’t have been anything wrong with continuing it and seeing where it went. I always wondered what happened to her, I truly hope she’s happy wherever she is and remember our afternoons together fondly.

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? She was one of several people in my life who started breaking down my Catholic guilt regarding sex, and opened me up to the idea of a casual  hookup as being an okay thing.

All things considered, how POSITIVE was this experience? Fairly positive

All things considered, how NEGATIVE was this experience? A little negative

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