Getting Back in the Dating Pool - Sex Stories

Getting Back in the Dating Pool

... ass?”

“Yes, actually my first memory of you is you bending over a table in one of the classrooms, working on a poster. You were wearing dark hosiery and a pleated skirt that mounded over your butt and split around your cheeks.”

“Okay, name some others.”

“Really? You want me to go there?”

She reached over and started to massage his cock through his pants.

“Alright. Your friend, Louise, wearing a pair of gray yoga pants. She’s got an athlete’s butt and I have admired it since that first day. Even went to her wedding and the wedding gown didn’t hide it’s charms. Then there is Chelsey, she was an ice skater and came in after practice one night to where I was doing some volunteer work to see her mother. I pretty much went crazy over the tight leggings and short skirt. That was another one of those that could have gotten me into a lot of trouble if someone had really noticed me looking.”

“So, always the ass?”

“Not always, mostly.”

“Legs?”

“Sometimes the legs, particularly if there are patterned stockings or tight leggings, your mother would be a good example.”

“Oh, you have a thing for my mother?”

“I wouldn’t call it a thing, she’s pretty good looking, after all, your beauty came from somewhere! And your smile is almost the same as hers.”

Madison had kept her fingers moving the entire time she was grilling him. The images in his mind as he brought these memories to the surface were pushing him toward orgasm and wondered if she was just going to ...

... finish him off with the hand. But she surprised him, “If you have admired my butt so long, maybe you should fuck my ass.”

He thought about how tight that would feel and before he knew it a full erection was standing between his legs. She went to the bathroom and returned a couple moments later with a pair of towels and a bottle of lube.

She proceeded to lube up his erection making it throb in anticipation, the pre-cum leaking out of the top. With his cock lubed up she smeared some more lube on her own ass and proceeded to climb on top of him. With a bit of careful placement she put her ass hole against the tip of his cock and slowly relaxed, letting her sphincter muscles slowly expand to allow his entry. Even getting the tip past the initial opening had him as hard as steel and he wanted to thrust up, impaling her on the shaft, but he held himself back, not wanting to hurt her. It took some will power, but he let her take control. He wiggled up further on the couch so she wasn’t at the edge, he didn’t want her to fall backwards and hit the floor.

Then she surprised him again. This time with a small vibrator that she slid into her pussy and turned on. His cock was immediately excited by the sensation of the vibrations through the thin walls separating the vibrator from his temporary anal home. She was just as excited, the stimulation sending her quickly over the top and shuddering with orgasm after orgasm. He finally couldn’t take any more and rolled over on top of ...