by Hungry Separated Guy

Gender: dude
Age: 50
Race/ethnicity: White
Location: NYC
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: IT Consultant
Relationship status: Separated
Religious affiliation: Extremely Atheist
How religious are you? Not at all
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? People think I might be gay but I’m not
How many sexual partners have you had in your life (including oral sex)? 100
How many hookup stories have you here posted before? 0

Alaska is Hot

How long ago did this hookup happen? 2 weeks

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? Pretty Black-German mixed-race. 31. Met in a bar because I sat next to her. She was with her best friend and step-brother. I thought she was good looking so I said something to her and she turned toward me and we didn’t stop talking.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I went on a solo trip to Alaska and it was my last night in Anchorage. A friend suggested I go to nice bars – and it works! I was looking for a hookup because it had been over a year since I had been with a woman. I got a vibe immediately but I never push until I get a green light. We went to a series of bars and I paid for everything for her and her step-brother (great guy). When we were alone, I suggested we go somewhere so we could “kiss” but we couldn’t get away. I kissed her and said, “that was nice,” and she liked it. Then we talked openly about going to my hotel and that this would be a one-night stand. We had both had one-night stands in the past.

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? In Alaska in June, it’s daylight all the time, so it was bright in the room at 3 AM. We kissed, I undressed her and we got in bed. I remember she said, “Don’t just finish quickly. I want you to pleasure me (orgasm).” So I gave her oral and she came. I put on a condom and we had sex in several positions for maybe an hour but I didn’t come (I don’t like condoms). We fell asleep and my alarm went off 30 min later, so I changed my flight from 7 AM to 3 PM. We had sex again for about an hour with a condom (didn’t come but hard the whole time). I said I wanted to take the condom off but we agreed not to. She didn’t give me oral 🙁 but I didn’t think to ask either).
She said I was her first “white guy,” and was shocked because she didn’t think a white guy would ever be interested in her. She left around 9 AM.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I told her I might have condoms, but even if not we could still have fun. In my hotel room I found two condoms. She said I was crazy for wanting unprotected sex and listed all the possible diseases.
I even told her I would like to get her pregnant! I don’t have kids and would like to. She has a 14-year-old and a two-year-old. I thought she would be a great mom.

What were your REASONS for having this hookup? I hadn’t had sex for ages and we had chemistry.

Were alcohol or drugs involved? If so, how much? We were both pretty drunk and even drank a bottle of wine in my hotel at 3 AM.

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? We texted and still do. I told her I wouldn’t forget her.

To whom did you talk about the hookup? How did they react? My best friend. He congratulated me for finally getting back on the horse after my wife left me.

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

Do you regret this hookup? If so, why? No. I’m very romantic so I have feelings no matter what, but we both knew it was once and done.

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? Best thing: I feel better about myself. Worst?: No oral sex for me, but it’s not that big a deal – oh, and I didn’t come (drunk and condoms).

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

All things considered, how NEGATIVE was this experience? Not at all negative

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