While living with Sandra, she was in the habit of hooking me up with other chicks and couples. On one occasion she arranged an afternoon meeting with a couple—some insurance salesman with his girlfriend who his wife knew nothing about.
Shelly was 50, or so she said. She came in wearing only a sundress with strappy shoes. She must have been a perfect 10 when she was twenty. She was still at least an LA 8—and that’s saying something for a woman of her age. She kicked off her shoes on the way in. After some small talk, she just let her sundress fall to reveal her stunning body. I was in my mid-30s, and I had never been with a woman who was 50. I was pleasantly surprised. She had absolutely gorgeous breasts, and her pussy sported a nice, very closely trimmed naturally red bush with a touch of grey. I love to go down on a woman, and it was wonderful going down on her. While Sanda sucked on her partner’s cock, she was busy sucking mine. She was a pro cocksucker, but I was ready to go for her pussy.
Her pussy was so tight, it actually hurt. I have never been with anyone with such a tight cunt. I think we fucked for almost a half an hour, but I couldn’t cum, even with what seemed to be a priapism. I used lots of lube to see if it would help. I just kept pumping her pussy over and over, and I was really sweating. When I told her I didn’t think I could cum, she went back to cocksucking for a while and I tried her pussy again, but I still couldn’t release. I never did release. I could have let her suck my cock, but she didn’t want a mouthful of cum, so I didn’t bother. She was so disappointed, thinking my performance was due somehow to her, which was definitely not the case. Her pussy was tighter than a cock ring. I think it was too restricting. To this day, I still don’t know what happened.
Before they left, Sandra sucked me off. I am not sure what happened with Shelly. It was a rough afternoon. Here I had two women—an LA 8 and maybe a 5, and it was the 5 who got me off. I have never had that experience before and never since. I would have liked to try again, but it wasn’t to be. And so it went…