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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: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Local Authority
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)? 6
How many hookup stories have you here posted before? 1

Young Guy Has Dirty Sex With 50 Year Old Tinder MILF

How long ago did this hookup happen? 18 months

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? I got talking to her on Tinder and the talk soon turned suggestive, I was trying to get her to come over the same night but she had plans, so we agreed to meet for a drink the following night.

I met her in the car park near the bars which are next to my flat. She was slim, brunette, short hair and big natural tits. She was wearing tight jeans and a black top. I could tell straight away from the way she looked at me that we were probably going to end up in bed together that night.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We went to a bar and she was talking about her travels around the world with her ex-husband who she’d recently been separated from. She seemed really down to earth. She said it was her first Tinder date joked that she still had her Tinder virginity. We went to another bar and the conversation got more sexual. She said she hadn’t had sex in a while and was using vibrators quite a lot. I took this as an indication that it was time to take her to my flat to hook up with her.

Instead of going to another bar when we left that one I just started walking towards the building my flat is in. She said “I like the way you just assume I’m coming back to your place”. This was clearly a “shit test” so I basically ignored it carried on talking and walking and she followed. My flat is on the top floor and I let her walk up in front of me. There aren’t many sights that can compare to seeing a tight milf ass in jeans going up the stairs in front of you while you think about how you’re going to be doing her very, very soon.

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? When we got upstairs we kissed on my settee for a while and soon I was feeling her tits over her top. I was getting really hard and horny, so I just pulled my cock out of my pants. She said “If in doubt, whip it out!” then slowly began jerking me off with one hand while tickling my balls with the other. I could tell she was really experienced at handling a man’s cock because I’ve never felt a touch like that from younger girls I’ve been with.
I suggested we go to the bedroom and she said “I’m guessing you want me naked too?” and I said of course. She lay down flat on the bed and pulled her tits out. I started playing with them for a while, flicking my tongue over her nipples which were already hard. She asked me to go down on her and I readily agreed after she put her legs in the air and pulled her knickers off. She had a pierced clit which I had never seen before but her pussy tasted good (guess maybe, like fine wine, the taste of pussy improves with age!). I stuck my tongue inside then fingered her while I licked her clit and she was moaning. She squeezed her legs around my head which was pretty hot.
I was getting really horny so I got out from between her legs and put the condom on. I rubbed my cock up and down her pussy and said, “Is this what you’ve been looking forward to all night?” She moaned “Yesssssss” then I slid my dick into her pussy and made her gasp.
I fucked her gently for a few minutes, holding myself up with arms either side of her. She was feeling my bicep muscles while I pounded away at her amazing milf pussy. It felt like every ridge inside her was perfectly designed to make my cock feel good. I was very turned on and wanted to really go for it, so I sat up straight with my knees resting on the bed, held her legs in the air by the ankles and started shagging her as hard and fast as I could.
She was moaning and thrashing around the bed a lot at this point- I figured she hadn’t been fucked like that by an energetic younger guy for a long time. She said “You’re really taking my Tinder virginity here aren’t you” and I smiled. She came hard, letting out a long, loud moan and her legs quivered. She put her hands over her face and I pulled out. I stayed quiet to let her enjoy the post orgasm glow for a bit then said “Did you enjoy my cock?” and she said, “Yes- did you enjoy my pussy?”
I moved to lie beside her on the bed and put my arm around her. This wasn’t really a romantic thing, I just think it always feels good to do it with a woman you’ve just had sex with. I hadn’t come so I said “You know since I went down on you….” and she had her lips around my cock practically straight away. What followed was the hottest, most sensual blowjob I have ever had before or since. She gripped the base of my shaft and deep throated my cock really slowly, using a lot of spit. I’m not sure how she made it feel so amazing but it did. This confirmed what I had thought earlier when she gave me a handjob on the sofa- she was really experienced at handling guy’s dicks and knew exactly what we liked.
I told her I was about to cum and she sped up a little, then pushed all the way down my shaft, taking my whole cock in her mouth just as I came. I could feel my cum pumping out onto her tongue- I think I came a lot. She sat up and looked at me and I couldn’t hide how pleased I looked. I asked her “where did all that cum go?” and she gave me a cheeky smile.

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? Great- dirty useless fuck that I enjoyed.

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), Learning new things, experimenting

How intoxicated were you? A little tipsy/high

What substances did you consume? Alcohol

How intoxicated was your partner? A little tipsy/high

What substances did your partner(s) consume? Alcohol

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 knows

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

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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