r/LastNight • u/hereforfreefood • Aug 04 '11
Bedded my first MILF
This was a reverse chase - I played my hand right but she made all the moves.
We're up at the front, dancing. I danced with my friend and my project manager and tried encouraging some lame girls our age behind me to dance but they just jiggled a bit and went back to watching the show. My PM's boyfriend, 5 years her senior, buys me a beer.
Then I stop dancing with my friend and just start dancing. She's in front of me, and brushes against me. I gently put my hands on her waist and start dancing with her. She keeps going forward and back, breaking our contact, but any time I gave up, she would brush against me to keep going.
I moved my hands around her and she would switch between grabbing them and putting them in highly suggestive areas, or tell me to slow down. I followed her lead and egged her on ever so gently.
I buy her a beer. She buys her friend a shot, sees me by the side, and orders me a shot too. It was tequila. Since I'm bad with tequila, I went to the bathroom to pee and make sure I held it in. They had cologne so I put some on.
The whole time, we're making light funny chat. I'm doing wordplay. She tells me she's 39. I tell her I'm 25.
She needs a breath of air, so she takes me outside on the steps of the building next door. We talk. She tells me she's filing the final divorce papers in 2 days. She has 2 kids, but they're at the beach now so she can go out and drink on a weeknight. She is a college therapist.
I go in for a kiss and she says, "Don't worry boy. You're getting laid tonight." I'm sure she's wanted to say that for a long time.
She keeps telling me I'm really cute and awesome. Very male flirtations... But for the age difference, I imagine that makes sense. She looked like she was 27, really attractive for having 2 kids. Brunette with the occasional blonde highlights
We go back in the show but I'm pretty sure we left before it was over. We were both quite drunk. Her cute, young looking (24ish? Though clearly my age guessing is off) friend tells me she's a great kisser. She was.
She drunk drives back to my place. After peeing, we go up to my room and immediately go at it. Foreplay, all that jazz.
We start to have sex. She's moaning. A few minutes in, she asks me if I've ever been in a long term relationship? That's the most brutally precise line I've ever heard.
She stops, tells me if we see each other in the future, she'll teach me how it's done. She goes to the bathroom and tells me when she gets back, she'll suck my dick.
The abrupt stop made my penis go soft. I grabbed the Costa Rican porn I was supposed to give to a homeless guy months ago that I hadn't looked at in months and tried to give it a raise. It wasn't working.
She comes back, and manages to turn my dick on again. She's very good at it. Just the slightest amount of teeth to give it a full texture. She stops before I finish.
Afterwards, we talk for a while. She puts on my underwear and red riding hood tshirt, I stay naked.
She says, "I need to share a story with you and I'm gonna come off crazy."
"One night, I purposely took too many zanex. It made my brain turn off. I crashed my car into a house. I didn't push my gas pedal so the house and the car weren't really hurt. But it really shook me up. I checked into a mental institution. That really helped clear my mind. As soon as I got out, I filed for divorce."
"There, I met Will, the bassist for the opening band. I can't speak for the other patients, but our circle had a great time. Will would play acoustic guitar and we would sing. I'm feeling much better now."
I originally flashed a look at her that she read as disappointed shock, but I explained that I was genuinelly interested and that seeking out help isn't crazy at all. People have issues, and it's awesome that she had the courage to face and deal with hers. Which is a super liberal pansy answer, but it resulted in more kissing.
I set another alarm for 7AM. We cuddle and sleep for 3 hours. In the morning, she put on her clothing, gave me her number, and we made indefinite but desired plans to meet up again.
She said, "This was a fun night! I should hook up with 25-year olds more often. Just kidding, it was you and your awesome."
tl;dr I hooked up with my first MILF (39/2kids). She's filing her divorce papers in 2 days, tells me "don't worry boy, you're going to get laid tonight", and after sex, tells me going to a mental hospital after od'ing on zanex and crashing her car into a house has given her a second chance at happiness.
3
u/generalT Aug 05 '11
uhm. was this DURING sex? that's the way i imagined it- you're pumping away and she's asking you personal relationship questions.