by Partyer1990

Gender: Male
Age: 44
Race/ethnicity: White
Location: Texas
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Communications manager
Religious affiliation: Roman Catholic
How religious are you? A little
Sexual orientation: Heterosexual
How many hookup stories have you here posted before? 0

Fucking Jenny

How long ago did this hookup happen? 1990

How would you best classify this hookup: One night stand with a friend

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 hooked up with my friend Jennifer. She was a year younger than me so probably 19 or 20 at the time. She was a petite brunette Irish American. Very cute! I had known her for about a year, always had been just a friend. I liked her but considered her flaky. She had had one boyfriend that she had lost her virginity to, an African American man probably about a year older than me. I remember this had aroused me when I learned she had slept with this man, I think because she was sexually available.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were at a party at my friend Tim’s house. A lot of barely underage drinking and probably some marihuana use. A couple of us had gone on a beer run to a liquor store and Jenny tagged along. She sat on my lap in the car and I got a hard on, and she must have felt this. I feel this is what got her aroused or whatever. We got back with everyone at the party and stayed outside talking. Now and then our friend Tim ( who later came out as gay) came out and talked to us. After a while we made out a while and then she basically told me I should come back to her place for sex. I was more than willing. We hung out at the party for awhile and then got a ride back to my apartment. We hung out there a bit and made out very passionately. I wanted to fuck her there. But my apartment was trashed so we walked to her apartment, probably about a mile away from my place. We talked a lot on the walk and it seemed like she was just broken up about her boyfriend (the black guy) … It hadn’t worked out. I wondered if she really wanted to do it, but kind of didn’t care. Already her behavior seemed like she was stalling. We got back to her place and her roommate was there. We ended up talking to her for like an hour. Again I remember thinking she was stalling, that she didn’t want to have sex with me. We talked to her roommate for like an hour, really banal conversation. By this time I don’t know if I was really interested or not and was ready to walk home. But her roommate finally went to bed and we went in Jenny ‘s room.

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? I was surprised she still wanted to have sex but she went into her bathroom and came out naked. She had a really cute body but I only got a good look at it for a second because she turned off the light and it was pitch dark. I stripped down and we made out. I groped her tiny firm breasts and started rubbing her pussy. She was aroused and wet but also sort of passive. She rubbed my dick a little bit. I ate her pussy for a while and again, she seemed to like it, but stopped me before she came. I got on top of her and fucked her missionary style for a long while. She seemed to get really worked up, maybe faking a little but definitely very wet. I fucked her pretty hard trying to come and she cried out “oh oh, I didn’t know you were a long distance runner!” She really did seem worked up and I think she may have come or almost come. But she also freaked me out so I didn’t come. I pumped her awhile and then stopped. She seemed fucked out and we just lay side by side. She got up and put on a bathrobe and came back to bed. I put my underwear on and laid back down and passed out. I spent the night.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? She had condoms and I wore one, I think the condom is one of the reasons I didn’t come. I never wore them with my regular girlfriend.

What were your REASONS for having this hookup? I was young and supposedly in a committed relationship but thought about and wanted to fuck other women all the time. My girlfriend was doing something else that night and Jenny was young, cute and made herself available to me.

Were alcohol or drugs involved? If so, how much? I probably had 4 – 5 beers and probably one liquor drink. I likely smoked some marijuana but not 100% sure, this was almost 25 years ago. I wasn’t incoherent or blacking out but definitely well buzzed.

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 remember her fondly but when I woke up the next morning I just wanted to leave, and I did. Walked back to my apartment, smoked some marijuana and took a nap. Went out that afternoon with my girlfriend and hooked up with her – back to normal.

A few weeks later. I caught a bad cold and Jenny came by and visited, she seemed pretty worried about me and brought me soup and wanted to take care of me. I basically was uncomfortable and told her that I thought it was a one night thing. She laughed it all off. But I think maybe she wanted to date me more seriously. Not sure.

A couple of years later she was in town and we went out to dinner. I wasn’t dating anyone and I think she wasn’t either. Again I think she was kind of feeling me out for a relationship but nothing happened.

To whom did you talk about the hookup? How did they react? I told a couple friends but didn’t want my girlfriend to find out. I played it cool. Over the next few years she hooked up with a couple of my acquaintances, similar MO, one night stands nothing serious.

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

Do you regret this hookup? If so, why? I don’t regret it … She was cute and had a hot body. I guess I regret not fucking her relentlessly until I came. I wasn’t as experienced. If I had it to over again I would have fucked her until I came, probably tried to get her to blow me.

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 is she was young and cute, the worst I didn’t come. It made me realize that sex is not any more simple than love is.

All things considered, how POSITIVE was this experience? A little positive

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

Anything else you want to add about this hookup or anything else? In the end, I bet most one night stands are like this. There are reasons why they are only one night.

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