What’s your gender? Man
How old are you? 31
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? USA Colorado Springs
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Military
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)? 15
How many hookup stories have you here posted before? 0

Crazy Awesome POF Hook-up Leads to First Anal for Both of Us

How long ago did this hookup happen? 5 years ago

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

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? Just met that day

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? Jasmine was a short, maybe 5’3″, black girl, around 20 years old, pretty face, decent body, small bust but nice ass and not fat. Met her on Plenty of Fish (POF) while I was stationed in Texas. She had a young body, and some kind of baby-daddy drama, we never really talked about her or my life situations. I didn’t know her at all and really only very briefly chatted on POF before I invited her over to my house to fuck.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Began on POF where I was looking for casual sex. I thought Jasmine looked attractive, sent her a few messages and quickly in our chatting asked her to come over and fuck, she quickly agreed. My house was mostly empty, my wife had left a little before that and I was finishing packing our things up.

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? Jasmine pulled her car into my garage of my house, I quickly closed the garage door behind her and met her right there. The usual meeting someone for the first time was quickly overcome when I just grabbed and her and forcefully kissed her. I grabbed her delicious ass with both hands and just devoured her mouth. After a little bit of passionate making out I took her hand and led her to the bedroom, taking off clothes as we went. I had the curtains drawn, candles lit and romantic music playing, she really liked that. Once on the bed I quickly laid her on her back and went down on her. She had a very nice pussy, hairless, no strong smell, very enjoyable for me to lick. Jasmine quickly started getting excited and told me she wanted to suck my cock so I flipped her over and we 69’d, with me on my back, her wet pussy pressed into my mouth as she slobbered on my cock.

This delightful state of affairs continued for awhile until I started probing her ass with my fingers. She gave no resistance as I rubbed on her rose bud so I continued to play with it as I sucked her clit. I worked some of her juices on a finger for lube and started to insert it, she continued happily sucking my cock and moaning. I reached back for a small lube bottle I had stashed under a pillow and lubed up two fingers and proceeded to further penetrate her ass.

Once I had her a little stretched and lubed I decided I’d try rimming for the first time in my life. I started darting my tongue on her cleft and she moaned deeply, stopped sucking my cock long enough to huskily say, “Ohhh you naughty Daddy….. this is the best sex of my life.” Encouraged I continued penetrating her ass with my tongue (I couldn’t taste anything beside the lube which didn’t taste like anything).

Eventually I broke off long enough to ask Jasmine if I could fuck her ass, she replied simply “Yes” and I took up a position behind her doggy style. I tried to gently work my cock in but I must have gotten too impatient and pushed too hard too early because she yelped in pain and pulled forward away from me. I sheepishly said sorry and said I’d fuck her pussy instead, Jasmine said “No… it’s ok, keep trying just slow.” Further aroused by Jasmine’s desire to press on I went back at it, and had to work my cock around a little bit, eventually finding a good position with one knee down and one foot on the bed and got all the way in. Jasmine was very excited now and I remember saying again “Oh God this is the best sex I’ve ever had.” Once I had my purchase I started to build rhythm and fuck her hard. I remember pushing deeper and deeper into her until I had forced her off the foot of the bed and she was propped up against a dresser just taking my thrusts, ass up, back arched, head thrown back moaning and grunting loudly, a sheen of sweat glistening on both of our bodies.

I was surprised I hadn’t cum yet, her ass was so tight and all of this was so exciting and new, but I really wasn’t even close until she said it… “Daddy cum in my ass I want it.” That instantly set me over the edge and I grunted that I was cumming, pushed myself to the hilt, pulled her hips back and pumped my load into her ass.

Once I was done I plopped back onto the bed, Jasmine went into the bathroom for a few minutes to compose herself and that was about it. We kissed, I grabbed her ass and she drove off.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? Yes, one

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 felt a little guilty about the thing at first, and just completely drained physically and emotionally but looking back at it it was probably the best single fuck of my life. I hoped to keep seeing this delightful little gem of a slut again (and I say slut in the most complimentary way possible) because she really was great, but definitely just fucking nothing else.

I hooked up with Jasmine one more time, in her little duplex house in a bad side of town late one night. I fucked her pussy that time and I ended up cumming in her mouth, she swallowed it all dutifully.

I deployed soon after that and I tried staying connected to her through PoF for awhile, hoping to fuck her again when I got back. She told me that it was her first anal experience ever, and that she went on to prefer anal. She eventually got into another relationship and I lost contact for good. I’d happily fuck her again and even years later I think of her telling me to cum in her ass when I need to cum.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None, Birth control pill / patch / ring / injection / implant, Anal

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, To cheer myself up, I was feeling lonely, Power / Dominance, Revenge / Getting even

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? No one ever

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? I don’t know / I’m not sure

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? First time ever anal experience and it was fantastic

What was the WORST thing about this hookup? Still desire anal and my wife has zero interest

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Showed me how much I love anal

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

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

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