by

What’s your gender? Man
How old are you? 38
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Toronto, Canada
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Small business owner
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 0

Team Manager

How long ago did this hookup happen? 1 year

What was your relationship status at the time? Engaged/Married (monogamous)

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

How long did you know the person before this hookup? For more than 3 years

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 was a petite milf with small but nice fake breasts.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were at a sports tournament and it was completely spontaneous.

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? Both of our kids were playing for another team as call ups for a tournament. She and her husband brought their camper to stay in and invited myself and my child to stay with them as there were no hotels available. The kids slept in a tent. Her husband had to work on one of the days. Once the kids went to bed most of the parents sat around the campfire drinking. I went to bed early before as I’d had enough to drink and figured it was time to cash in. I was using the living area couch that pulls down as a bed for myself and the main bedroom was near the front with curtains separating it from the kitchen/living quarters. I had just brushed my teeth and taken a piss and was just pulling up my pj pants when she walked in. Good chance she had seen some of my cock but I’m too old to really care. I jokingly asked if she timed her entrance on purpose. She said, “of course, had to get a peek while I can!” And I said, “well that’s fine cause I put some hidden cameras in your room so make sure you are turned towards the doorway when you undress”. She went into her room and likely started to change out of her shorts and T-shirt as I called out, “the cameras not working you’ll have to change out here where I can see!” She laughed and I laid down on my bed to go to sleep when she came out and said, “so change right here then?” I told her it was only fair because she had just seen my dick. The banter went on for a while and I truly thought it was just harmless flirting when she lifted her shirt up half way to show the undersides of her boobs. I spit out, “those look nice but I can’t see the top half with that shirt on!” With that, we crossed the line and she took her shirt completely off and I sat there staring at her gorgeous breasts. My mouth was completely ajar and my cock was at 3/4 mast. I decided to counter and pull my pants down to my ankles and gently played with my dick. She grabbed her own boobs and gave them a squish. I patted the spot beside me on the couch bed and she sat down. Eventually, she reached into her sweats and started to play with her own vagina. I casually tugged her pants and she took the hint by lifting her hips and sliding them off. This continued for a while and I thought this might be it, a mutual jerk off. I was starting to get excited when I gently placed my hand on her thigh and squeezed it. She let out a moan so I squeezed some more and traveled upward to her thong which she then took off. She pushed me back so I was lying with my feet on the floor when she straddled my hips. She pressed her vagina on top of my cock and began to slide her opening along my shaft without penetration. It was absolutely mesmerizing to watch this woman fuck me without actually fucking me. This continued for a few minutes and other than me touching her thigh with my hand I hadn’t laid a finger on her. I looked up to check out her boobs and couldn’t resist any longer. I reached up and began to squeeze and caress with my hands. She placed her hands over mine and continued her rocking motion. After a few minutes, she threw her head back and slid off my cock as she began her orgasm and as soon as I saw it I began to erupt all over her stomach. Once we both calmed down a bit we just stared at each other. She leaned ahead and we began to make out lightly. I was so excited still that I actually got a semi and she reached down to stroke it, still covered in my come. I had a vasectomy years ago so I wasn’t worried when she sat up and we finally began to have intercourse. It was incredible watching her ride me in lots of positions and when she turned around in reverse I got a great look at her rosebud. I licked my finger and started to probe her anus slightly when she whimpered, “I want you in my ass!” Since my cock was already wet from her pussy and my cum we didn’t need lube and I began to ease into her slowly. We fucked slowly while she circled her clit. Eventually, I pulled out and began to jack off with my tip right at her entrance. I came all over her vagina and hand while she continued to finish herself off. I think the guilt for both of us started to settle in as we got a bit awkward and went to bed.

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? Guilty but at the same time completely satisfied.

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

What were your motives for this hookup? Attraction to partner(s), Just happened, I don’t know why, just went along with it

How intoxicated were you? A little tipsy/high

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? I don’t know / I’m not sure

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

To whom did you talk about the hookup? How did they react? No one

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? A little bit

Did your partner get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Do you regret this hookup? A little bit

Why do you regret this hookup? I cheated

What was the BEST thing about this hookup? The sex was crazy good

What was the WORST thing about this hookup? Cheated

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? Somewhat positive

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

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