Anthony
Anthony walked in nervously. He hadn't done anything like this in years. At almost 50, he had been out of the scene for the most part for a while. He had been married to his husband for about 10 years at this point and generally lost interest with the "contemporary gays". He went to clubs very infrequently. He generally did not enjoy going. He was a former porn star, so he didn't have any problem getting people to talk to him. However, he was extremely picky. He always had his hot husband back home if he needed sex.
Anthony was definitely attractive, granted he had plumped up a bit since his "performing years". He was quite muscular, but not lean anymore. He was moderately hairy, having some light dark hair on his chest but a ton of hair on his stomach. Normally, this wasn't how porn producers wanted men to have body hair, but it was how his grew. He had a decent dick too, about 6 inches long and 5 inches around. He felt moderately "decent", but it was his face and cheekbones that made him popular. He kept a full but well-groomed beard.
He saw the flier in the bathroom last night. He was horrified by the proposition, but there was only one slip left. He took it instinctively. However, during his cab ride home, he stared at the slip that had become crinkled in his pocked. "What's the worst that could happen?" It was anonymous. If he couldn't get it up, he could just leave. In fact, that was what he was planning. It didn't hurt that this mystery woman lived very close to Anthony.
He looked at the bottom half of a woman staring at him from across the room. This wasn't his first time seeing a vagina in person. He'd never fucked one, but he's seen them. It didn't look like what he remembered. He kneeled between her legs and browsed some porn, jerking himself slowly. Surprisingly, he didn't have too much of an issue getting hard. He settled on some muscle bear porn.
After he was erect enough, he figured he should get going with it. He rubbed the head on her pussy, not really knowing where the hole was. He recognized the clit, maybe it was there? Keeping his cock right under her clit, he pushed. It didn't go in. Maybe that wasn't it? She was very wet, if that was her hole, it would have gone in. He moved down. Tried again. No dice. He got soft.
"Fuck", he muttered. He had to jerk himself off again. Finally, once erect again, he applied some pressure towards the bottom of her pussy. It slipped in very quickly. It was an unusual experience. It wasn't very tight, but the inner walls seemed to caress his cock. It had ridges, it was tight on the inside but not on the outside, completely opposite of a man's ass. The lips still seemed to grip onto his cock. It felt extremely wet. Anthony normally didn't like this, but it would have to do, he couldn't do much about it.
Anthony kept his eyes glued to the laptop screen. This didn't feel too bad, provided he had this visual stimulus. It felt like a very good blowjob, granted he usually didn't get off on blowjobs. After about 20 minutes of slowly going in and out of the wet vagina, he started feeling like he was going to cum. He figured he should speed up his fucking now so that feeling wouldn't slip away. He sped up, now pounding her quite deeply. He heard the woman gasp. He tried not to focus on that. His hands on either side of her torso, leaning quite deep. His happy trail started rubbing right on her clit.
Anthony was farther from orgasm than he suspected. He had to keep going through or he was going to lose all his progress. The woman kept making noise. Again, he tried not to focus on this, and only wanted to focus on the feeling on his cock. Suddenly, the woman moaned loudly, and her pussy squeezed him. He figured this was her cumming. The squeezing felt like she was trying to milk him, beckoning for him to cum in her. Something in Anthony found this insanely erotic. Anthony stopped humping and let her convulsions massage him. It didn't take much for Anthony to start shooting his seed in her. It felt like an insane handjob stroking the cum out of him. He hadn't realized that he was fully pressed against her.
After coming down from the high, Anthony pulled out quickly, pulled up his gym shorts, and walked hurriedly to the front door. He had a ping of regret already - he couldn't focus on this. The guilt would eat at him if he thought about it too hard. Once at the door his grunted a quick "Thanks".
Trisha recognized the South African accent.
Perfect. He has great genes.
To be continued...