by Rocco

Gender: Male
Age: 48
Race/ethnicity: White
Current location: California
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Teacher
Relationship status: Attached now (single then)
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 81
How many hookup stories have you here posted before? 4

Fun With a Former Lesbian

How long ago did this hookup happen? 18 years ago

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…)? 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? She was a curvy brunette executive. I placed a racy ad in the local alternative weekly newspaper she responded and we agreed to meet for a picnic lunch at a local park. I was recently out of a relationship and not looking for anything too serious, while she was interested in exploring her Heterosexual side, having recently broken up with her girlfriend. On meeting her I found I really liked her and the feelings were mutual. We agreed to meet a few days later. Obviously we were meeting for sex, but she suggested we meet for dinner first, which actually was fine with me.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? After a fun dinner at a local restaurant with lots of eye contact we headed back to her place.

We began making out in the living room. She was a great kisser and we both were getting turned on. She interrupted the proceedings and declared that this is where we agree to use condoms. I was naturally willing to oblige since this was what I expected anyway. So having settled that issue she stood up, took my hand and led me to her bedroom.

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? She closed the door, even though nobody else was home, then we both quickly undressed. We kissed some more. She had wonderful breasts with responsive nipples and her pussy got really wet as I sucked on her nipples and fingered her below.

Then she announced: “now I am going to suck on you!” It was quite a turn on, yet it left me feeling like she had watched porn to gain insight into how straight folks go about it. I was really enjoying the blowjob, but soon I was overcome by an intense desire to fuck. I reached for a condom and she announced “let’s fuck!”
She proceeded to lie down, spread her legs and then using one hand to spread open her pussy, like they seem to do in hustler magazine. We started fucking and it felt terrific. She seemed to really enjoy it and we tried different positions before returning to missionary to finish off. I had a great orgasm. I suggested we have another go and this seemed to surprise her. She had no idea this was an option but soon enough she warmed to the idea and we went at it a second time. The second time was even better; the giddy eagerness of the first time seemed replaced with a feeling of being together in a shared adventure.

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

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? We used condoms.

What were your REASONS for having this hookup? I was feeling horny.

Were alcohol or drugs involved? If so, how much? She had a glass of wine before.

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 did not really have any expectations, but we wound up getting together about once a week fora couple months. She wanted more, but I was not ready for this yet and so we drifted apart.

To whom did you talk about the hookup? How did they react? I told one female coworker who was married. She commented “well, some people have a tennis partner they get together with once a week for a game. Maybe this isn’t that different, except you aren’t playing tennis.” Telling her about it was actually counterproductive because it confirmed in my mind that this was just a fuck buddy situation and nothing more, limiting my options.

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

Do you regret this hookup? If so, why? No, not at all.

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 thing was the sex. The worst thing was that I was so focused on the sexual novelty that I failed to recognize the long range potential and so ended up staying aloof.

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

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

Anything else you want to add about this hookup or anything else? I think ladies sometimes overestimate the capacity of guys to get a hint about relationships. Had she said to me that she really wanted to be more than just fuck buddies I would have been open to this but instead she kind of hinted at this and never came out and said it. Funny how these things only become apparent many years later.

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