What’s your gender? Man
How old are you? 29
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What’s your current relationship status? Single
Religious affiliation: Atheist
How religious are you? Not at all
What’s your sexual orientation? Heterosexual

Tis The Season

How long ago did this hookup happen? last night

What was your relationship status at the time? Same as current status

How would you best classify this hookup? Short fling

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

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 is 42, about 5’6″ average weight, black hair blue eyes, nice tits, a bit of a pothead and very flirty, little past her prime but still attractive in that milf/cougar kind of way, has a couple kids and is engaged. She started with my company six months to a year ago, she was friendly and flirty from day one and at first I just assumed that was her personality but I started to notice she was only really flirty and close with me. she never wore revealing clothes but I could tell she had nice tits. I thought she was hot but never thought anything would ever come of it.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were having an unofficial Christmas get together with the work crew at the local strip club and she came along, we partied pretty good for about 5 hours before everyone started to call it a night, she had moved to my table and was sitting next to me rubbing her leg against mine, we were both pretty drunk and I was trying to ignore it, finally the last few straggler left, we were the last two from our group, and about to call it a night as well when she asked for my phone number, I gave it to her and I immediately got a text that read “You have a nice cock don’t you….” she was staring at me with lustful eyes, I gave a simple yes response and I felt a hand on my leg, she asked if a had a GF, I said no then she asked when I last got laid, I told her it had been a few days, her hand ran up my leg and started rubbing my semi hard cock, her eyes lit up and she asked if I was fully erect, I shook my head and she bit her lip, she pulled out her smokes and said she should go out and have one, I told her I’d stay inside and finish my beer, thats when she leaned in and whispers in my ear “Just come out to my car, i’m not letting you fuck me, but I am gunna suck your cock” I gladly got up and followed. We got to the car and started making out in the front seat, we were all over each other as she told me she’d wanted to fuck me for months now cause she was certain I had a nice cock, she was rubbing it frantically then told me she needed to see it, I unbuttoned my pants and pulled it out and she just gasped then blurted out “Holy fuck! I figured you were big but not that big” she grabbed hold of it with one hand, then the other, she added “oh my god your cock is so thick, I have a small mouth so this is going to be interesting”

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?
I reclined the seat and she went down sucking, stroking and gagging any time she’d go for the deep throat, after about 10 minutes though she was starting to question her skills, I assured her she was doing great and I always took a while when it came to blowjobs, I asked where she wanted it and she said where ever I wanted, I told her it was her choice and she smiled saying she’d love to swallow it, I warned her I tend to shoot big loads and she just went back to it, a few minutes later I gave her warning and she stroked it out of me, coughing and gagging as each burst hit the back of her throat but she held it together until I was finished, she swallowed it without hesitation then commented that I had great tasting cum. We sat there for a few minutes then went right back to fooling around, I wanted her pussy and kept trying to get a hand in her pants but she kept blocking me, then finally said she didn’t want to cause she was a bit embarrassed that she’d get me all wet cause she was a squirter, that made me want it even more and I told her so, her pants were a thin material so I just started working her pussy over the pants and fondling her tits, she was starting to get fairly worked up and thats when it happened, she tensed up and let out a groan and soaked her pants, she sat there trembling and kissing me then crawled over to straddle me, this time when I went for her pants she didn’t stop me, I began to rub her dripping went pussy and with in minutes she was soaking my hand again, over the next 20 minutes she managed to squirt another half dozen times, we were both soaked and she could barely speak, pulling herself together enough to say she couldn’t handle any more. When she finally came down from her high she couldn’t help but notice I was rock hard again. I was within walking distance and going to leave but she insisted on driving me.

We pulled into my driveway and started going at it again, she started telling me how bad she wanted my cock in her pussy but she wasnt going to let me fuck her our first night fooling around, as if she planned on future hookups, I asked if she wanted to come in but she turned me down, I shut off the car and grabbed the keys, then began to head to the door, she came and grabbed the keys but instead of leaving she said she would come in for a bit, but she insisted we weren’t going to fuck, we got to my room and she was still was still denying me, I was hard as a rock and dropped my pants as I was having my hand soaked by another squirting orgasm, I reached into my nightstand and grabbed a condom, she just stared me down then shuffled to the edge of the bed, we stood up and she turned her back to me, bending forward on the bed I pulled her pants down and slipped the rubber on, she moaned and jumped as I teased her lips, then I pushed my head in, she was surprisingly tight then with about an inch in she told me to stop, I asked what was wrong and she just laughed and said “My little pussy isn’t exactly used to accommodating what you’re packing stud” when she gave me the go ahead I eased my self in deeper, until my balls were planted firmly against her dripping lips, she was breathing heavily and gasping unable to speak, I began to pump my cock into her, she was snug and I was definitely more than she was used to, I was bottoming her out when she instructed me to slow my pace and grind instead of thrust, she was shaking and whimpering almost, I asked if she was good, she just blurted out “Oh! UGHH! JESUS fuck! you’re rubbing my fucking cervix” she was loving it and cumming all over my cock, I began to thrust as her little pussy squeezed my cock, she clenched the comforter and began to meet my thrusts, I couldn’t hold myself together any more, grabbed her hips and hammered her poor little cunt, when I finally came to a stop I could feel her juices at my feet. It was a little after midnight and she said she really needed to leave.

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? It still doesn’t seem real, we will see how things go.

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Intoxication, It was easy / convenient

How intoxicated were you? Completely wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol, Marijuana, hashish

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

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

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? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? We work together

What was the BEST thing about this hookup? She’s a squirter

What was the WORST thing about this hookup? Co-worker

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

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

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