The Agony and the Ecstasy

Before I met my second wife I spent a lot of time in the online dating scene. One site, in general, was a treasure trove of one night stands and short flings. On one particular occasion, I met a redheaded woman named Sam. Our first date was short but promising, we had plenty to talk about, both of us writers. I like to call these meetings fuck interviews, where you feel the person out and if you can see yourself waking up in the morning next to them then it's game on. Sam was a little crazy, but I like crazy women. A friend of mine once asked, “Why do you like crazy women so much?” To which, I replied, “Because they're unpredictable. You never know when you're going to get a finger up your ass.” Anyway, on our second date, we went to an outdoor skating rink in Manhattan. I'm a shitty skater, weak ankles and all, but we managed to make it out without too many bruises. Afterward, we decided to go to an Irish pub on 6th Ave for a drink or three. Once there, Sam revealed to me that she was trying to behave herself. She'd had many affairs, some with married men, and she didn't want to feel bad about herself in the morning. After this confession she made a proposal, we could go back to her place and do anything, but at no time could we fuck, or could our underpants/panties come off. Now, I don't know how I manage to always find the women with these strange restrictions, it's been that way since I was a teen. If you read my earlier stories about Debby and Dawn you'll know that I never got naked with them or even kissed, but I guess we find each other. When we got to Sam's place we had a little bit of weed and then started making out on the sofa. Mindful of the rules, we pulled each other's clothes off until we were down to Sam in a tank top and panties and me in a pair of silk underpants. I did eventually get the t-top off and was greeted with a pair of lovely b cup breasts with nipples the hue of a fine rose wine.   Over the course of about an hour and a half we did things I've usually only seen in porn, but all without penetration. Doggy, reverse cowgirl, me with my face buried deep in her pussy soaking up her scent, grinding against each other...etc. She must have come 4 or 5 times, and I was so into her hot little body, but in the end, the restriction was just too much for me and at about 4:00 in the morning I just hadn't cum yet. Exhausted, I slipped my hand down to my cock, and not breaking the rules, stroked myself to a long needed release as she looked on. Sam, if you're reading, thanks for one of the most frustrating and exciting sexual encounters of my adult life.