Not Very Pleasant


by autosome

Gender: male
Age: 48
Race/ethnicity: British Jewish
Location: London
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: parent
Relationship status: married
Religious affiliation: atheist
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 300+
How many hookup stories have you here posted before? four

Not Very Pleasant

How long ago did this hookup happen? 15 years

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? start of booty calls

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 knew the woman from bumping into her in coffee shops and bars in the city of London where we both worked. She was rather dumpy, not the best figure and rather plain with mousy hair. She was a couple of years or so younger than me. She was nice, pleasant, not very interesting to talk to, little in the way of life experiences but we had a common interest in Terry Pratchet novels JRR Tolkien, which is how we got talking.

One day I bumped into her when leaving work and suggested an drink.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was very early evening and the Monument Bar on Fish street hill wasn’t that busy. We had a drink and chatted and during the conversation, I mentioned the word dildo, she then said “I’ve got one of those, actually it’s a vibrator”. This caused the conversation to turn sexual and generally I know once a woman starts talking about sex and sexual encounters, then it a pretty good chance we will end up in bed. By about 8pm we were on our way to her flat.

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? Once in her flat we had a glass of wine and started kissing and then made our way to her bedroom. It turned out that neither of us had condoms. So we performed oral sex on each other. She sucked me first, it wasn’t the best and she tried to perform deep throat unsuccessfully. After I finished going down on her, I was still very horny and very very erect. She said she was disappointed that I wasn’t inside her but didn’t want to get pregnant. I suggested anal sex. To my surprise she agreed, but admitted to never have had done it. I fingered her anus with some baby oil, slowly working my finger in and carried on like that while encouraging her to relax, I then added a second finger into her to encourage her anus to dilate further. She indicated that she was ready for my cock and I entered her doggy style, I have to admit I was fantasizing about another girI knew, as her bedroom was decorated in a Wiccan style and the scent of joss sticks was irritating my nose. 

I eventually ejaculated in her arse and she said she like the feeling of my cock throbbing and squirting in her. As I pulled out my cum started coming out too and I noticed it was tinged brown as no douching had taken place. It dribbled onto her duvet making quite an obvious stain.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None

What were your REASONS for having this hookup? It was a possible opportunity to have sex

Were alcohol or drugs involved? If so, how much? Moderate use of lager and wine

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 indicated that she would like to have sex again and next time use protection. She also stated that she was ok with me seeing other women as she’d seen me on dates around where we worked.

To whom did you talk about the hookup? How did they react? No one

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

Do you regret this hookup? If so, why? No regrets

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 led to a booty call relationship that was solely about each other using each other for sex. We had virtually nothing in common and never talked about anything other than a narrow set of books which we had differences in opinion of.

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

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