Getting Back in the Dating Pool

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 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 ship doing the same thing. It was a great deal, he was paid a nice sum and the company setting it up provided full room and board for the entire three weeks, along with full access to the park and all the other cruise amenities. He thought about asking Madison to go with him, it would have been amazing to have her join him for some uninhibited coupling away from people they knew. But reality butted in and he realized it would be very difficult to explain both of them being gone at the same time and lots of questions would be asked. It was much easier for him to say yes given that Madison could look after Krazy Kat. He could never remember the name that the cat had been officially given when she had appeared in their home, but Krazy Kat fit her to a T.

When he returned, well tanned and without having gained more than a pound or two, Madison met him at the airport. They chatted about what occurred over the last three weeks as she sped up the highway to his house. They barely got into the door before she was all over him, stripping off his clothes in the mud room, which was probably going to have happened anyway, as the laundry room was right there. She dragged him down the hallway to the bathroom and started up the shower, stripping herself as the water warmed up. There was no doubt she wanted him and wanted him immediately as they climbed in under the warm shower. He was glad to clean off the travel dirt, but was even happier to run his hands over her body.

He snuggled in against her back and wrapped his arms around her, his right hand sliding over her left breast and massaging it firmly, with the occasional tweak of the nipple. She leaned back into him as she felt his erection prodding into her lower back. His left hand slid over her belly and worked its way carefully into the folds and began rubbing her clit. Her first wave of orgasm was over with quickly, the fastest he had ever gotten her to climax. It was obvious that she had needed the release. He soaped her up and enjoyed the feeling of her body sliding against his. The soap foam slid down her body and dripped off her breasts. She did the same to him, the lather lubricating their skin and making for a very erotic situation, but also threatened to send them flying on the slick tub. By the time she got both hands to his cock, he was immediately sending an eruption of cum across the tub, splattering on the wall and sliding down to the drain.

They rinsed off and dried each other, before moving to the bedroom. The bed was one of the few places in the house they seldom used for their sexual release, but this was unusual. He'd had a number of women approach him during the cruise, but they were either underage girls or grandmothers with more than a few extra pounds on them. So he had essentially been without any relief other than his hands for almost a month.

She was in full control as she pushed him back on the bed, not even allowing him to get his feet off the floor before she came at him. For the first time, she attacked his cock with her tongue, slathering over the eight inches of flesh as it throbbed in her hand. She slid it between her lips and rolled her neck, her tongue continuing to dance around the bottom of his tool as the top of her mouth stimulated the head. Sliding her head up and down, a few gags caused all kinds of strange sensations on his bare dick. More and more of his penis slid down her throat until it was firmly swallowed, her nose tickling his pubic hair. It was only a few moments after getting there that she started humming, at first he thought she was choking, but her eyes let him know she was alright. And that was enough to push him over the edge, spewing cum down her throat as he yelled in pure bliss.

She sucked him slowly as she removed his tool from her mouth, no saliva or cum left as the suction cleaned him off. Madison wiped her face off and climbed up on the bed beside him.

"We need to talk."