by Jack

Gender: Male
Age: 30
Race/ethnicity: White Italian
Current location: NYC
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Healthcare
Relationship status: Single
Religious affiliation: Catholic
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 38
How many hookup stories have you here posted before? 0

Platonic No More

How long ago did this hookup happen? 5 yrs 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…)? 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? “Alexis” and I were very close in HS but she always had a boyfriend. She moved out of state after HS and I visited her once or twice and she returned to my city 3 times or so. I always had a crush on her. She has the greatest legs and B cup breasts. Beautiful face. And a great friend

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She came to town with her husband and she visited me with a girlfriend from HS who split early and we continued having drinks. She told me to kiss her from the bottom of her neck to her mouth in the bar. I did and ended by kissing her lips but no tongue and she said “do that again, that’s not a kiss.” I did it again and we made out.

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 went to my home. On the way in she said promise if we have sex we will be friends tomorrow like always. I promised. We sat in my living room kissing and she said “I want you to fuck me.” I took her shirt off and told her I wanted to fuck her. I was kissing her breasts. She told me she wanted me to fuck her doggie. And how easily I could slide inside her if she bent over the couch on the floor. How wet she was and to lift up her skirt and pull her underwear to the side and fuck her hard and call her a” dirty slut.”  I took over and bent her over the couch and fucked her calling her a little slut and told her how “tight her little pussy was.”

I love doggie but I wanted her to come and I’ found most girls don’t cum that way so I finished with her missionary.  She wanted  me to come on her tits and I did. She was a sexy, dirty talker. She liked to be dominated a little and enjoyed a lot of dirty talk. She told me that she couldn’t believe how hard I was and that she could feel it. And how big my dick is. I have a 7.0 inch dick but I think she meant compared to her husband. She was with him since 16 yrs old and was excited by the new experience. We remain friends.

Did you have an orgasm? Did your partner(s)? Yes we both did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I pulled out. We discussed STI history and as close friends. She knew I was clean and I knew she had only been with her husband. She was on the pill.

What were your REASONS for having this hookup? Attraction, friendship and alcohol

Were alcohol or drugs involved? If so, how much? Alcohol played a big role. I don’t think it would have occurred without it.

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 loved Alexa as a friend then and now. We are still very close and we became even closer friends after sex. I would love to enjoy intimacy with her again

To whom did you talk about the hookup? How did they react? One male friend. He know how sexy Alexa is and was happy for me. Wanted to hear about it, of course, but I was vague

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

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

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? This was a fantasy of mine since HS. I’m glad I had the experience and maturity when we screwed to last and make her orgasm. As a young man, I would have came in two secs.

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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