What’s your gender? Man
How old are you? 28
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
How many sexual partners have you had in your life (including oral sex)? 10
How many hookup stories have you here posted before? 4

She knew what she wanted

How long ago did this hookup happen? 1yr

What was your relationship status at the time? Single

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

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 45, average height and weight, long brown hair, pretty brown eyes and big boobs, she had 4 kids [I knew her daughter] and she was recently divorced, obviously at her age she had some miles on her and was a little past her prime but she exercised lots and kept in pretty good shape for her age. Obviously knowing her daughter I had no sexual history with her and although I thought she was a milf I never gave it any real thought. I knew her pretty well as her and 2 daughters shared a rental house, the girls had the basement suite.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Her daughter was having a big pool party and she was a pretty laid back mom who on occasion would join us for a few drinks, something which from time to time led to some innocent flirting which was mostly just us young horny guys teasing the MILF, I had fairly recently broke up with my girlfriend and that came up in conversation and she asked how I was doing, as the night continued we became drunker and she stuck around longer than normal, we tried convincing her to join us in the pool but she wasn’t having any part of that. I eventually had to piss and the downstairs bathroom was a lineup so I snuck upstairs, which was usually off-limits during parties but I knew she didn’t mind me up there. Right in the middle of my piss I hear the door open and I look over my shoulder and I see her locking the door behind herself. I frantically finish my piss and ask what she is doing and she responds “Well…’re about to get laid.” Standing there with my dick in my hand I find myself at a loss for words as she approaches, I was pretty drunk and any sense of right and wrong was pretty blurred. I guess in an attempt to avoid banging my friend’s mom, I mention a lack of condoms which she quickly shot down, saying she had dealt with that issue years ago, standing face to face she finally instigates things and starts jerking me off.

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? We just stood there as she yanked on my cock, she stops briefly and we undress each other, standing there in a lacy black bra and matching thong I can’t help but stare in amazement at how good she looks. She orders me to go sit on the toilet where she promptly straddles me, when she impaled herself on me it was almost surreal, as she bounced up and down on me I found it hard to tell if it was real or I was dreaming. She removed her bra unleashing her tits that were a bit weathered but I wasn’t about to complain–it was hard to say how long she rode me on the toilet for. I couldn’t get comfortable so I told her to move to the counter where I proceeded to pound her pretty hard. We were lucky the party was loud because she was very vocal, it didn’t take long for me to finish and I couldn’t help but finish inside her, I got dressed and she told me to get back to the party.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, one

Did your partner have an orgasm? I don’t know

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 was pretty happy with myself the next day, but she texted me begging me not to tell anyone. I agreed and she said she had never done something like that and it was a drunken thought that she shouldn’t have acted on even though she admitted she did enjoy herself. It was a one time thing, we have managed to kep things from getting awkward.

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, Intoxication, Just happened, I don’t know why, just went along with it

How intoxicated were you? Completely wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Completely wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? I don’t know / I’m not sure

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? 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? 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? The risk of getting caught

What was the WORST thing about this hookup? Awkward secret to keep, it was also weird when after I had blown my load, in a totally nonchalant manner she asked if I had ever fucked her daughter.

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

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

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