My Favourite Life

September 1, 2006

Shelly the Older Woman

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…

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  1. ohh man that sucks… impotence always comes when u need it the most

    Comment by shocking — September 2, 2006 @ 4:16 am | Reply

  2. dang that really sucks. hate that when it happens.. oh well at least you did cum later 😉

    Comment by aboutmakingmoney — September 3, 2006 @ 2:39 am | Reply

  3. […] All right. I’ll come clean—cum clean? I fall typically into the 2 to 5 minute range. I have lasted more and less, but mostly, I am in that range. About the title line, I have had this happen only once, and I was under duress. No really. I have experienced the other extreme as well, where I couldn’t cum at all after half an hour, so I gave up trying. I know a friend who has done the marathon thing, too, but that’s not what this is about. […]

    Pingback by Premature Ejaculation « My Favourite Life — September 14, 2006 @ 12:28 pm | Reply

  4. […] I have experienced many pussies in my lifetime, perhaps too many. In this experience I have had pussies that were too tight and pussies that were too loose—but only one of each. The remainder were somewhere in between. And you know what? It didn’t matter. I have to admit I am sometimes in the mood for a tighter or looser fuck, but most women can control to some extent how tight they are. […]

    Pingback by Pussy: The Tight, The Loose, and The Ugly « My Favourite Life — November 3, 2006 @ 6:59 am | Reply

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