In the weeks following their initial encounter John met up with Leo several more times. Usually it was on the weekend, late at night or early in the morning. It had taken a few days for them to text each other. But eventually Leo had broken the ice and John had responded. John knew that there would never be a relationship. He liked Leo well enough but there were no romantic feelings there and soon he realized that Leo felt the same. The first night was the longest conversation they'd ever had and when they met, they kept it light; usually getting straight to business. It was a good arrangement. They both had stressful jobs and after receiving the first text from Leo a couple of days after the night they met, John felt better about the experience. John had to admit to himself that although he didn't have feelings for Leo, he hated the idea of a guy fucking him, coming on his face, and then walking away with no further contact.
After the second time they had sex John was able to say, for the first time, and with confidence that he was a bottom. He'd had help in this.
"I didn't think you'd be such a good bottom," said Leo the second time they met. They were standing in John's living room making small talk before getting naked. It was about a week after the first night.
"Well I wouldn't say I'm a bottom..." said John uncomfortably. "I've topped before. It was a long time ago though. I guess I usually just...go with the flow." He trailed off feeling stupidly embarrassed. This was not Leo's intention. He coolly deflected.
"Oh, sorry," Leo said with a shrug.
"To be completely honest, I don't have a lot of experience with guys," John said.
"Well we can definitely work on that." It was mid-day on a Sunday. John was completely sober and a little nervous. Part of him still couldn't believe what had happened the week before, but he knew he wanted it again. John had spent that last week fantasizing about Leo. Thinking about what he would do if they met up again. He loved the attention he got from Leo and the fact that such a handsome young man was so attracted to him. John was also extremely attracted to Leo. His height, his masculinity, his naturally smooth dark skin. John loved it all. In the texts they had exchanged Leo had complimented John regularly and John knew that it wasn't just flattery. They had even gone as far as to trade pictures (never showing their faces of course). Two days earlier Leo had finally given in and sent a picture of his dick to John. John had received the text while at work and had masturbated furiously on his lunch break...and several times since. That Sunday, with John once again bent over his own couch, Leo had leaned down and whispered in his ear.
"Say you're a bottom." Leo was balls deep inside of John. John was naked except for white briefs that were pulled down around his thighs. His rock hard dick was pressed against the sofa cushion. John was in that place where he completely surrendered control. Leo raised up behind him and started fucking his ass rhythmically. Leo pumped hard but not as hard he could. He wanted this to last and wasn't sure how much John could take. Leo pushed the full length of dick into John and held it there. John could feel every inch of Leo inside of him.
"Say it. Say you're a bottom," Leo said again. John could hear a cocky yet charming smile in Leo's voice. It turned him on.
"Oh fuck. I'm a bottom. I'm a fucking bottom." He came unexpectedly, his body bucking and jerking on Leo's dick. The inexperienced older man could feel Leo's hips pressed against his ass cheeks, Leo's huge balls against his taint. John moaned as he grinded his ass backward against Leo. John sat up and rode the thick dick, jacking off as he shot wave after wave of cum until the ride was over.
"You're not done, are you?" Leo asked.
"Not by a longshot," John replied. He then proceeded to turn over, pull his rumpled underwear over his feet, throw his legs in the air, and get fucked in a pool of his own cum.
After that day John had gotten more confident sexually.
"I'm definitely going need dick tonight." John said it out loud. It was noon on a Saturday and he was preparing to drive back to his old home to go to his older son's basketball game. John loved his children but was nervous about being back in the old neighborhood. Pat, the man he had carried on an affair with off and on for two years, and his wife stilled lived there. It wasn't a small town but there were definitely too many people who knew what had happened. John also knew that the reasons for Pat and his wife, Trisha not moving were purely financial.
On the long drive back to his old home John felt waves of anxiety. He was starting to wish he'd met up with Leo that morning before heading out. But then thought better of it. Maybe the sex would have relaxed him enough to make it through the day without jitters. But then again, the idea of being around his family and old friends directly after getting plowed by another man made him feel a kind of awkward shamefulness that would have ruined the day. The drive gave him time to think back to the day about a year earlier that his life changed forever.
John and his then wife Sarah had gone to a party at a house in their sub division. They were friendly with that couple and several of their other friends were there. John was mainly looking forward to having a few drinks with people who were not his wife. Their relationship had been empty for several years by that time but Sarah had decided to be willfully oblivious to their problems...