During my senior year of college, I joined a group of friends from my hometown for a night out at the strip club. We started at a local bar and got a ride to the club around 11pm. When a friend got me a private dance, I was taken aback by the age of the stripper. No disrespect, she turned me on, but was clearly in her 40s, or older. Just surprising considering I assumed most strippers were on the younger side.

It was around Halloween and she was dressed in a nurses outfit with a short skirt. She sat me down and made some small talk, and started to give me a lap dance. We were both into it, and she pulled up her skirt and started to rub my cock up and down her ass crack. She turned around and asked me if she could take it out and I (of course) said yes.

I was turned on and fully hard at this point, and she was into it. She sat down on me and said “you’re making me wet,” and she really was wet, I could feel it through her panties. She continued with the lap dance, trying to hide my cock from anyone passing by the booth, and would sneak her hand down to massage it every couple minutes. “After my shift do you want to go for a ride with me,” while she winked at me. “You’re sexy.” She rode me hard in the booth for 5 or so minutes, I assume trying to get off from rubbing her clit on my cock. I’m surprised I didn’t cum, but I had been drinking. She stopped, started making out with me, and said to find her at 2am.

I continued to drink and chat with friends, and let them know about my plans for the night. She emerged from the back with her bag, and walked out to her car with me. She said she would bring me home, but wanted to take the long way so we could have some fun first.

We pulled up down the street from my house and started hooking up in the back seat. She had condoms (Skyn Large, the best condoms of all time), so I put one on and got right to it. I got on top of her and rested her legs on my shoulders. I put my cock in slowly, and she started to moan, “oh fuck I’m wet.” I continued to work it in. “Fuck the shit out of me,” so I started to go as deep as I could and she started to cum. “You’re going to make me cum,” and before I knew it, she was squeezing her vagina around me and she started to cum. I had never made someone cum so quickly before. Usually takes much more effort, but she was so horny. I started to thrust as hard as I could and ended up cumming a minute later. It was hot.

We talked for 5 or 10 minutes and I asked her if I could fuck her in the ass. I had a feeling she had an anal fetish from all of the rubbing and ass talk earlier in the night. She admitted she loved anal, but she didn’t want to because she hadn’t prepared, but that she wanted me to, “fuck my (her) ass loose,” another time. She told me that she had sons in their teens, and that she was looking for someone to hook up with consistently, and that she’s into guys in their 20s.

We hooked up five or six more times over the next few months and it was great sex. We tried anal but she said it was uncomfortable and wanted to continue with piv sex. It was gaping after, I lasted for a long time (surprisingly). She wanted to be tight for anal with others in the future, which I respect. Still incredibly hot.

An era I will never forget. Thank you, sexy.