Getting Back in the Dating Pool - Sex Stories

Getting Back in the Dating Pool

... her, pulling her legs up to her chest and the peaks of her skinny ass grinding deep into his crotch. He pounded for almost five minutes before his balls crinkled up and shot another load into her, coating her tunnel. Truly exhausted, they lay motionless for several minutes before she made him move off of her.

That became his incentive for hitting various milestones of weight loss and fitness levels, a good session of anal when he reached them. It proved to be a good motivator as his waist thinned down and his upper body strength improved. Not only was his body getting healthier, he was learning to prolong his love making. Part of it was to make sure that Madison was satisfied, but also to prolong his own pleasure. He never knew when she might decide that she no longer needed a friend with benefits.

Madison’s parents were a bit concerned with the amount of time she was spending with him, but she explained it as that he was her latest project. She was trying to get him ready to go out into the social world with the idea of finding a girlfriend and stop being a recluse. And when she was working on him, she wasn’t thinking about her own situation, it was helping to buffer her pain and helping her adjust to her own need to go out and find someone. Her parents would have been more concerned if the two had been closer in age, but given their age difference was over 25 years, they really didn’t think anything long term could come out of it.

A couple of times a week, she ...

... would follow him back to the house after the workout, or show up at his door after work and push him back into the house. Most of the time she would start by laying him out on the floor and riding his face, letting him lick her to ecstasy over and over. During their time together she never went for oral sex on him, something he wasn’t too upset about, after all, he was getting laid on a regular basis. His tool was a bit on the large side, it would certainly have caused her some trouble. That wasn’t to say she wouldn’t give it a lick or two as she teased him to full size. But Madison much preferred having him plugged into her vagina, stretching it as she rode him to an orgasm or two. And true to their agreement, she always made sure he had an orgasm before they finished up for the session.

And there was certainly an increase in interest in him from other women. Before when he attended church, Madison and her parents were the main interface, along with a couple of other widowers and a few couples that had been good friends. No one pushed him to change, but Madison made it happen. There were a few women that had divorced that would give him a smile that at first was a bit uncomfortable, but his younger sidekick could read the signs and worked to encourage him to respond and would surreptitiously excuse herself so that they could chat alone.

Then Matt got a great opportunity to head to a major theme park and teach a couple of one week art classes, followed by a week on a cruise ...