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What’s your gender? Man
How old are you? 28
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Middlesbrough
Highest education received: College degree (eg., BA, BS)
What’s your current relationship status? In a serious relationship (monogamous)
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)? 7
How many hookup stories have you here posted before? 0

Brunette MILF

How long ago did this hookup happen? 1 year

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? 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? She was 50, short-haired brunette, average height, big tits. I met her on Tinder, got her number and the conversation turned sexual pretty fast. I wanted to go round to her place to fuck her that night (of course) but she insisted the next day was better for her so we made plans to meet up then.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met up for coffee at a little place near my house. We talked about our lives, her ex-husband and her travels around the world.

We moved to a bar and the conversation got more sexual. She talked about how she hadn’t had sex for a while and was looking for a fuck buddy. I said, “you might have found one.” She talked about how she loved doing herself with vibrators almost every night. I was getting bored of talking and thought it was time to fuck her so I started walking towards my apartment, her following, unlocked the door and started walking upstairs. She said “I love how you just started walking to your place!” but I ignored her and she kept following me.

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? Back at my place we were sat on the couch talking and I said “Are you going to kiss me then?” and she said yes. We made out for a while, me playing with her big milf tits all the time. I felt my cock starting to throb inside my jeans.

After a short while, I pulled down my jeans and boxers and got my cock out. She stroked my balls with one hand while slowly jerking me off with the other. I could tell she was very experienced in handling a man’s cock. I’ve never felt a touch like it before or since. I thought she must have pleasured a lot of guy’s dicks in her time and this turned me on even more.

I took her hand and led her to the bedroom. I was now naked and she was now only wearing her knickers and bra. Her tits were so big they were virtually bursting out. She said, “I’m guessing you want me naked too?” I said definitely. She lay down on the bed and took her bra off while I pulled off her knickers.

I started fingering her pussy and she immediately said “lick it” so I happily obliged and tasted her awesome milf juices as I flicked my tongue over her clit. She had very perky nipples and I played with them while I ate her out.

I decided it was my cock’s turn so I sat up from between her legs and put on a condom. I wanted to tease her so I rubbed the tip of my dick up and down her pussy and asked, “Is this what you’ve been looking forward to all night”. She said “Yessss” in a kind of low, animal-like way. I could feel how wet she was, she had got really horny and was basically gagging for my dick inside her at this point.

I put her out of her misery and slid the full length of my cock inside her soaking pussy. She tilted her head back and let out a moan of pleasure. Since she was 50 years old I thought she wouldn’t be used to getting fucked by a young, athletic guy so I thought I’d give her a treat. I started pounding her pussy vigorously in missionary position. She looked like she could barely handle it- she was grabbing the bed sheets and moving her head about moaning.

After not too long she let out a high pitched moan, her body shook a little and she put her hands over her face. I stupidly ask “Have you cum?” and she said “Yes!!!”.

I then moved up to lie next to her on the bed. I put my arm around her and we started talking. She mentioned how relaxed she was even though we’d only just met. I said cheekily “You know since I went down on you…” and immediately she grabbed my cock and put her lips around it. As with the handjob, she gave me earlier I’ve never had a blowjob as good as this one. The pussy fucking felt the same as with younger girls but there must be something about experienced women that gives them a magic mouth and hands. She slowly deepthroated my dick and it felt so good that I can’t really describe it. Any young guys who are reading this, go and get yourself a blowjob from a mature woman if you haven’t had one. You won’t regret it. After around two minutes of this, I could take no more- I said “I’m gonna cum” and she sucked me more vigorously until I shot my load in her mouth. She sat up and started talking again. I asked “Where did all that cum disappear to?” and she shot me a cheeky smile.

We talked for a little while then she decided she was going to go. I walked with her back to her car and kissed her goodbye.

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 had no interest in a relationship with this woman, she messaged me a few times and I gave lackluster responses. I would have liked to have sex with her again but I could tell she had started to like me and didn’t want to put her in a position where she would get hurt. I shortly met someone else I wanted to have a monogamous relationship with and told her this which she accepted.

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), To cheer myself up

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? Nobody.

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? A little bit

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Her handjob and oral skills were incredible and I’m glad I got to experience them.

What was the WORST thing about this hookup? Realising afterward that she took it more seriously than I did. I thought it was just a hookup for her too at the time, but I think she was actually looking for someone.

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? Fairly positive

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

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

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