Part 2 Of Hookup Night

by Steve

What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Palm Springs
Highest education received: College degree (eg., BA, BS)
What’s your occupation? RN
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? I enjoy a little male fun at times
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? 10-12

Part 2 Of Hookup Night

What was your relationship status at the time? Dating casually

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than 6 months

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? Sherry was at the chat room gathering as Teacher. I had hooked up with a drunk teacher earlier in the evening and we had some fun but she cut it off earlier than I would have liked. After she left I asked housekeeping to come up and change the linens and towels telling them that I had spilled some liquids on the bed, while what had really happened was that Teach was one hell of a squirter. I went back to the bar after Teach left and talked with several ladies from the group.
Sherry was older than me by probably 40 or 45 years. I would guess her age to be 65-70. That did not deter me because all I was interested in was getting my dick wet.
Sherry is tall probably 5 feet 10 inches, slender, attractive, smallish tits, a cougar climbing a vine tattoo on her right leg from her hip to her ankle. her pussy is shaved and she very much enjoys sex

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were talking in the bar. Sherry and I had chatted some in the chat room but never sexually. The bar was another story. We were sitting next to each other. She kept leaning into me with her right hand on my thigh. She would whisper into my ear things like “is it hard?” “Do you like it wet,” She told me that she knew that Teach and I had fucked earlier and she wanted to get some of the same. I told her to meet me in my room in 30 minutes. I said my goodbyes and left. I got up to my room and my room was nice and neat – all fresh towels and linen.

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? Sherry knocked on my door and I let her in. She came into my arms and we kissed passionately with lots of tongue. She began rubbing my bulge and I grabbed a hand full of nice tit. We moved to the bed and she undid my zipper and pulled me out, got down on her knees and began to suck. Very nice job working the head over, massaging the balls, sucking the balls, I stood her up and undressed her, pushed her back on the bed and proceeded to eat her pussy. She was moaning loudly as I worked her clit and g-spot over. She came all over my face. I continued to eat her pussy and she came 3 more times. I spread her legs and slid my cock home. Fairly tight pussy, just wet enough to make good lube. I had already cum 3 times with Teach so I knew I was good for a while. I stroked her missionary for about 5 minutes, got her doggie for another 5, rolled her on top of me cowgirl and reverse cowgirl, her pulling on my balls as she rode me. She turned cowgirl again and leaned over for me to suck her tits. I took her nipple between my teeth and started tugging and she had a massive orgasm, her pussy clenching down on my cock plunging in and out of her. She came a couple more times. I rolled her over missionary again and pounded. I finally had her lay on her right side with her right leg straight out and her left knee bent up to her chest. I straddled her right leg and slid my cock into her sweet pussy, with my balls dragging on her thigh and my cock deep inside of her I filled her pussy with my cum. We fucked twice more and fell asleep. She woke me in the morning with a nice blow job, got up and left

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than 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? We talked some over the weekend but did not hook up again. She may have hooked up with one of the other guys there, I don’t know. We met at a couple of other gatherings and hooked up once more which was very enjoyable. I enjoyed my cougar fucking my brains out

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Thought it was an important experience to have, Making new friends, It was easy / convenient

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? Small amount of alcohol or drugs, not enough to feel it

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? one of the other ladies knew I had hooked up with both Teach and Sherry, we got together the next night but that’s another story

How would you best summarize people’s reactions about this hookup? Relatively positive

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? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? we both wanted it. She was considerably older but very sexual and I now know why cougars are what they are

What was the WORST thing about this hookup? nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? no

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

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

Anything else you want to add about this hookup? Sherry was a very sexual older woman that knew what she wanted and made sure I got what I wanted

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? as long as everyone is on the same page it’s great

What do you think about the Casual Sex Project? great

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