Highest education received: College degree (eg., BA, BS)
Relationship status: Single
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Bicurious hetero man, likes to watch black men
How many sexual partners have you had in your life (including oral sex)? 30+
How many hookup stories have you here posted before? 0
18 Years Later
How long ago did this hookup happen? 1 Year
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/Sex with an ex
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’s a petite brunette, about 5’3″ with small tits, great ass and a cute face. Straight, shoulder length hair. She’s the first Mom I’ve ever had sex with. We’ve known each other since we were 14, we’re now 33. We were each other’s first high school sweethearts. We’d had awkward formative sexual encounters together as teenagers including some oral sex. I think she always had a strong sex drive but was very repressed at that young age. We came very close to hooking up about 7 years ago before her kids were born. We had a romantic past, but had become friends in the “end”.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The seed was planted 7 years ago. I always regretted not getting inside her pussy and still harbored dangerously hot fantasies about us together, despite being in a serious relationship with another woman for a time. Her marriage inevitably began crumbling and she came to confide in me one day. Over the next several months we began daily/nightly sexting sessions, she began sending me naked photos, and it continued to escalate to the point of sex. There was a lot of planning involved given that we were meeting in secret and trying to avoid her husband. After several hookups we became estranged for the summer, but reconnected in the fall after I sent her a text on her birthday.The one I chose to write about occurred after we had been estranged. We reconciled and entered into a fuck-buddy contract. We agreed to meet at my apartment for no-strings-attached sex, usually in the morning when she was on a long break. I smoked a joint before she got there, and I was nervous even though we’d been together before. I was more excited to feel her than ever before.
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? We began kissing passionately the second she walked through the door. She was wearing heels, a tight skirt and sexy green top. We undressed each very slowly. She stroked my dick for awhile then I began eating her pussy. She had begun growing out her bush because she knew how much it turned me on. She came from oral after a few minutes. The sex began in missionary, then we progressed to cowgirl where we spent most of the time. She obviously hadn’t been fucked in awhile and really grinded on my cock for a good 40 minutes and it was truly awesome to feel her melting all over me. We kissed passionately throughout.
Did you have an orgasm? Did your partner(s)? Yes. After she came 7-8 times, I took off the rubber and she got on her knees in front of the bed and watched me masturbate myself to orgasm. She closed her eyes and turned her head slightly as I came. My semen landed on her tits, neck, face, and thighs. After taking a few moments to catch my breath, we started kissing again and without saying a word I began slurping jizz with my tongue and we shared it together in each other’s mouths before she swallowed it.
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I wore a condom. She was not on the pill.
What were your REASONS for having this hookup? 18 years of pent-up lust is a very good reason. Once we began a sexual relationship, I realized she was the kinkiest and most adventurous woman I’d ever been with. I wanted her more and more because I felt free to express my sexuality with her.
Were alcohol or drugs involved? If so, how much? She had a small glass of wine, I had smoked marijuana about an hour 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? We took a shower together and she went back to work. This was followed by a couple of more hookups, but none as intense or memorable as this one. We eventually broke it off.
To whom did you talk about the hookup? How did they react? I’ve only shared details with my shrink, have mentioned it in passing to others. My shrink thought it was exciting and spent a lot of time talking about it.
Was this a consensual and/or wanted experience for you? For your partner? Totally consensual and yes we both wanted it badly.
Do you regret this hookup? If so, why? Not at all- one the most thrilling days of my sexual life.
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 part was the excitement of putting all of my sexual charge into someone I’d lusted after for many years, and feeling totally free.
All things considered, how POSITIVE was this experience? Somewhat positive
All things considered, how NEGATIVE was this experience? A little negative
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