Seducing at the Local Watering Hole

This post is sponsored by The T Bar.

by Enjoying Life

What’s your gender? Man
How old are you? 37
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? small town
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Logistics
What’s your current relationship status? Dating casually
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 30 or so
How many hookup stories have you here posted before? 0

Seducing at the Local Watering Hole

How long ago did this hookup happen? Last fall

What was your relationship status at the time? Dating casually

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than a week

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 met Jane at a local bar. I chatted her up and found out she went there for a few drinks to get away from the drama of some family stuff. So I humored her. She was 5 foot 6, dark hair, average build. She said she was a high school English teacher. We went outside because she wanted a smoke. Then we went for walk. I just had the feeling that she wanted to get laid. We talked about a lot of stuff, mostly relationships. I was casually dating but didn’t say that. She broke up with some guy that she was dating for way too long and said she was through wasting her time with things that didn’t go anywhere. I complimented her on her personality and intelligence and that she looked beautiful. She liked that. I got her number. I called her the next day to set up a date.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? On our date we went to a bar. She was drinking a lot. She threw her leg over mine as we were chilling on a sofa in the bar. A bit later, she went out for a smoke. I never saw her for a long time. i looked around and found out they wouldn’t let her back in. The said she had too much too drink. She was pissed and embarrassed. I said these guy are jerks then hugged her and kissed her. We laughed it off and walked back to her place. She did not expect guests so she told me not to judge her for the mess in her place. I said no worries, my place is the same. We started making out in her apartment. We went into her bedroom and started taking off each others clothes. I didn’t have a condom and she didn’t have any either. She said she didn’t want to get into anything just yet. We made and then I started fingering her. She was moaning a lot and we fell asleep together. We went for breakfast. I continuned to compliment her on how sweet and nice she is. Wanting to seal the deal I made plans for dinner with her a day later.

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? Our dinner date was fine. We both had a lot to drink and were feeling good. She told me she was 40 years old. I said she looked younger than that and said she has nice skin. I was thinking she was my age, 37 or maybe 38 but 40 is fine. Older women also are a turn on for me. At this age there is a don’t give damn combined with a bit of jadedness from bad relationships, so I find that a good challenge. I went back to her apartment and saw that she cleaned it up a lot. It didn’t take long for our clothes to come off. I started fingering her again since she liked that. Once she was good and wet I put on the condom and started fucking her missionary. She said she likes it when I squeeze her nipples. So I was pounding into her and squeezing her nipples and massaging her breasts. She said she likes the feeling of my big dick. I told her to lets try doggy style. I pounded her from behind and since she liked me squeezing her nipples, I started spanking her as fucked her doggy style. She liked that too. She went from all fours to resting her head on her arms. I liked how her ass was now higher in the air and I squeezed her ass hard. She liked that too. I came and then we rested a bit. She liked to kiss and cuddle after sex. She said she used to be a competitive swimmer and wanted to get back into swimming again. It sounded like she had some body issues. So I complimented her on her body she looks great and she is also great in bed.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I left after we had sex. I called her the next day and we talked a bit. Since she said she was through with bad relationships, I didn’t know what she was expecting about this. She also said that she didn’t want children at this point in her life. So I just said we can date and would like to get to know her better. I was dating other women casually at the time so it was good for me to not get too wrapped up with anyone as I figure them out. Of course I didn’t tell her this. We met up again about 8 or 10 times after that and we had sex every time. She was also good to go without condoms a few times. She loves the closeness and feeling. She was a bit bitchy but in a good way. She was very opinionated about a lot of things. I didn’t agree with half of her ideas but this tension turned me on. It made the sex more aggressive. I liked pounding into her and fucking her hard after some “lively” debate and I found that she actually like it rougher. She really liked my big cock too.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Condoms

What were your motives for this hookup? Fun, pleasure, horniness

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? None

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? She liked to fuck and she said she likes a guy with a big dick. That was a good compliment.

What was the WORST thing about this hookup? I broke it off with her after a couple of months. She was getting to be too emotionally needy. I told her I wasn’t feeling well to meet up two times in a row and she took a fit over the phone. That’s how it ended.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It’s good to see that I can still hook up the same way as when I was younger, and in fact I am entering my prime years since I am more confident with more experiences.

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

All things considered, how NEGATIVE was this experience? Not at all negative

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I’m still learning about myself.

What do you think about the Casual Sex Project? Interesting.

You have a hookup story to share? Submit it here!