by Saul
Gender: Male

Age: 29
Race/ethnicity: White
Location: US
Highest education received: College degree (eg., BA, BS)
Occupation: Bookkeeper
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? None


The Childhood Friend

How long ago did this hookup happen? 5 Years ago

How would you best classify this hookup? Friends With Benefits

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 had this childhood friend. Let’s call her Jane to protect her name. I had known her since we were very young children and I had never thought about her in that way. She was short with pale skin and Raven colored hair and she was curvy. We were very close friends and she had never thought about me that way either.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were at my apartment and both were dealing with recent breakups. We were sitting on the couch talking when she kissed me which lead to some heavy making out. Eventually we headed for the bedroom.

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 undressed each other and I had never realized how hot she was. A lot bigger breasts than I had any idea that were nice and firm. We made out naked for a while and I began to lick and suck her breasts and she gave me oral which I eventually returned. Normally Jane was a quiet person but she was a lot more aggressive in the bedroom than I would have ever thought. She initiated most things. I achieved orgasm several times and so did she and we went at it again. We did missionary and doggie style and girl on top, which was her favorite because she liked to be in control. She was incredible in bed and it was one of the best nights of my life. Ultimately we fell asleep late and I woke up with her in my arms the next morning and she went home.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I used protection that first night even though I knew Jane was clean and on the pill. We both were very safe.

What were your REASONS for having this hookup? We were both lonely and horny.

Were alcohol or drugs involved? If so, how much? Maybe had a glass of wine each, not much.

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 spend the next two years as friends with benefits, often fucking two or three times a week and sometimes more. One weekend we went on what was supposed to be a ski trip but we spent the whole time in the hotel room in bed. We explored sex together and were FWBs until I had to work out of the area for about six months and she had a boyfriend when I got back. We were never really anything more than casual. Things are awkward between us now.

To whom did you talk about the hookup? How did they react? At Jane’s request I have never told anyone and we were always trying to keep it discreet.

Was this a consensual and/or wanted experience for you? For your partner? It was for both of us.

Do you regret this hookup? If so, why? A little bit. Things have been awkward between us since she got married last year.

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 the best sex of my life and Jane was an incredible lover. Before her I had never been one for casual hookups and I had no idea women could enjoy sex too.

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

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

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