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What’s your gender? Man
How old are you? 22
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Ohio
Highest education received: Some college (currently in college)
What’s your current relationship status? Single
Religious affiliation: Jewish
How religious are you? Somewhat
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 1
How many hookup stories have you here posted before? 0

Losing My Virginity To A MILF Twice My Age

How long ago did this hookup happen? Two years ago

What was your relationship status at the time? Single

How would you best classify this hookup? Fuck-buddies / Booty call

How long did you know the person before this hookup? For 1 to 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 my best friend’s roommate who happened to be a little more than twice our age (43-44). I’ve always known that she is a little crazy and a big slut from stories she would tell us and by the number of men my friend said she would bring home. I would see them pretty frequently so we became good friends but I was always pretty reluctant to pursue anything sexual with her because I was a virgin and found her a bit intimidating.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? She’s the type of woman who’s pretty much down with anything with most people. She also has a super insatiable sexual appetite so over the time that I’d known her she made quite a few passes at me. However, as I said before, I was a virgin at the time and she had always intimidated me so I mostly ignored or declined all of her passes with the exception of a kiss here or there. That was until one day I basically decided (probably while jerking it) “fuck it” and began to be more open-minded about using her to lose my virginity. Eventually one day I just decided to go all in and while we were alone I asked her “so when are we gonna screw?” She seemed a little surprised by this because I had always rejected her in the past but after this, I made an effort to always be ready if the situation came up again. This included jerking off just before going to see her in case something did happen between us I could last. One day when I arrived at her house, she had just gotten back from the bar with some other people I knew and was obviously pretty drunk and feeling “enthusiastic.” I could tell because she was constantly groping and talking dirty to me. Knowing this was going to be my night I went into the bathroom as everyone was leaving or falling asleep to jerk off one more time so I could last a little longer my first time. As soon as I exited the bathroom and entered the room she was in, she flipped off the lights. Her lips met mine and she began to fumble with my belt.

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? As soon as we both got undressed, I began to take the opportunity to explore and worship the first naked body I’d ever seen in person. I forced myself to pull my tongue out of her mouth and began kissing, licking, sucking, and biting all the “feel good” places on her body like her ears, neck, breasts, naval. Eventually, I settled between her legs and started planting some kisses in her inner thighs and blowing hot breath on her pussy as I’d seen in how-tos. After a little teasing, I finally began to eat her out the best I could for my first time. I knew enough to try a little fingering and clit sucking. I didn’t receive a ton of praise but she didn’t seem bored either which I took as a sign that I did just okay. After that, I returned my mouth to hers so that our pelvises would line up and I entered her. She felt amazing on the inside and fortunately had just jerked off, I was able to pound her as deep, hard, and fast as we wanted without being too worried about coming early. She gave me a lot of positive feedback loud moaning, smacking my ass, and throwing her legs in the air like a pornstar all which helped to boost my confidence. Feeling motivated I continued to fuck her with everything I had using long, hard, deep strokes. The futon we were on would shift and creak pretty violently every time I buried myself in her which led me to wonder if she’d tell me if I’d gone too deep for her. However she only seemed to be enjoying it so I didn’t worry. I tried to pull out my cock out as far as I could each time before ramming it back in but this caused me to slip out a number of times and I fumbled to find her opening again in the dark which was embarrassing though. Then we switched positions and I ended up laying on my back where she took a place by my feet and began to suck my cock. The head wasn’t the greatest because I could feel her teeth at points but when she would jack me off with my balls in her mouth and it felt amazing. Then she looked up at me from my crotch and asked me “aren’t you going to come for me?” This turned me on a lot but it also embarrassed me a little because at certain points I’d had trouble staying hard after having just jerked off and I knew she already came once for me so I felt some pressure to produce something for her. I suggested she ride me and I told her I’d come inside her. Although it took some concentration after I got into the rhythm of her bouncing on my cock and watching her tits sway, I did manage to get off in her. It was more of a dribble than a spray though I was sure. After that I was still so eager to please so I went down on her again right after having come inside her.

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 still jerk off thinking about the first time I fucked her and we’ve hooked up since then although she is still the only woman I’ve ever been with. She’s reliably dtf pretty much anytime I hit her up. We also just hang out as friends sometimes. Having written this I might message her to tell her about it although I won’t let her read it because she still doesn’t know she took my virginity.

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, Learning new things, experimenting, Thought it was an important experience to have, To feel better about myself, Submission / Relinquishing power, Didn’t want to disappoint my partner, It was easy / convenient

How intoxicated were you? A little tipsy/high

What substances did you consume? Marijuana, hashish

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? Very

Did you consent to this hookup at the time? I didn’t give a clear ‘yes’, but I didn’t give a ‘no’

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? I waited for a while to tell my best friend but apparently when I did she had already beaten me to it.

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? Pleasing her. Pounding her as hard as I could without worrying about coming too quickly. Losing my virginity. Being with an experienced partner

What was the WORST thing about this hookup? Difficulty coming/ staying erect. Being unable to find a pussy opening in the dark.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? It’s given me more confidence and experience.

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? I will never forget it!

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 don’t mind casual sex and I think everyone has needs. I would like to try sex with a loving significant other though as I feel casual sex can lack intimacy.

What do you think about the Casual Sex Project? It’s liberating to tell your own story and really hot to read other’s stories!

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