Author: SkyscraperTreehouse

[MF] Dirty sleepover touching

This happened when I was around 32 and my female friend Dani was 20 or 21. Dani was a platonic friend, she was part of a group of girls I was friends with. I’ve always been into younger (legal!) women, but Dani and I never had anything. She was super pretty but she never seemed into me as anything more than friends so I never pursued it.

Dani lived in San Diego but her and her fiends often partied in LA a couple hours away. I live halfway in the middle in Orange County. One night at like midnight she texted to see if I was awake and asked if she could call. She said she was driving home from LA and needed to talk on the phone to stay awake. I offered that she could stop and crash at my place or even stop by and grab a coffee to wake up. She passed on that at first but then said she wanted to stop by because she was getting really tired.

She stopped by and ended up deciding to crash at my place. I was excited but then again she hadn’t seemed flirty and had never really shown any desire to take it further. Read more »

40 [M] I picked up a legal 18 [F] from high school and fucked her all afternoon

I’m sure some won’t agree with what I did, but I have to share the story. I posted a kind of risqué abs photo last week and someone I didn’t know DM’d me and said “I’d fuck you”. We started chatting and it was an 18 year old girl in a town next to mine. We started chatting and exchanging pics, and at one point I was so sketched out I had her take a pic of her ID to make sure she was legal (she has braces). She was legal, and she really likes older men. She told me she was recently with a 33 year old guy but wanted to be with someone older. We chatted for a couple days, and tentatively made plans to meet on Friday afternoon. It was only at that point when I realized she was still in high school. She asked me if I could pick her up at school, and asked that I park in a shopping center close by so nobody saw. I went at the agreed time, still not really knowing if she would follow through. When she was a few minutes late I really thought she chickened out. Then, she showed up and jumped straight into my car and gave me a hug. She’s super cute, 18, latina, braces, a little chub, and big full c cups. She had a cute dress on. Read more »

I [M] fucked a woman [F] while she FaceTimed her BF

Had to share an insane recent Tinder experience. I’m 40 (M) and matched with someone that is 30 (F) with an interesting proposition. She said her and her BF were looking for another guy to add to the bedroom and asked if I was interested. She admitted she had been in relationships in the past where they brought additional partners into the bedroom but hadn’t done anything like that with her current BF.

We chatted for a few days, got to know each other, and talked a lot about how it would go down in the bedroom. We made a plan for an evening we were all available and set some ground rules. Literally 30 minutes before I was headed out the door to go to her place she texts and says that her BF is chickening out. He doesn’t want to do it. Although he has a solution, since he knows she wants a new big dick. He wants me to go to her place, and she will FaceTime him in (they don’t live together). She asked if I was still into it, well of course I am. Read more »