His lips were pressed firmly around the soft cylinder of his best friend's cock. It was bigger than his and was fully erect. They had been streaking with a camp out of girls two backyards away. He and his brother Tom were both naked and he had lost a "dare" in a naked version of truth or dare. They were Freshmen in college.
That was the first time he'd experienced anything you'd consider bisexual, and that last time he'd physically be involved directly. He would recall this over and over as he chatted online to anonymous men in chat rooms and eventually the instant message feature of AOL.
"My lips press hard around you," Donnie would chat and then just fantasize. "My tongue presses on your tip, tasting your clear prequel."
He would make up the rest, how he would "gag on your length" or "cup your balls as I take the rest." He would milk his own precum chatting with several men at a time, getting them off and roaming rooms for others to start it all over again. One night, while his wife was away, he got 20 men off before cumming hard into the sweatshirt he had worn all day.
Their sex life just wasn't what it was after their son was born, not that they'd set the world on fire in the bedroom before that time. It dropped off after the birth, he had turned to masturbation to the new world of online images, chats through AOL. The fantasy world opened up and he would create multiple names on AOL, some even female as they would get more interest. He could chat anytime about sex and found he enjoyed being a woman to a man's desires.
Donnie discovered it was easier and hotter to chat with men in the bi-curious chats, with other married men in the same situation. He would type in 32 MWM and there would be a half-dozen requests that he could start conversations, looking for the most interesting one or just chat with as many as he could. He really like to weave a good story, most times having to be the top, forcing his cock in places just getting to image what that would feel like stroking in the downstairs office.
"You top or bottom" would pop up and he'd say bottom, but then "me too" would appear. He was quick to take control and claim he was "switch" and go top in the message exchange. That was not him in his married bed, Donnie always had trouble being aggressive, pushing his desires on his wife. He was horny as hell, reserved to push for kinky things and often for sex at all. Online he would push and be more dominant, talking about ramming his cock deep in a guy's throat.
He did look for women online and chat with, often trying to stay connected with those showing interest. He found himself chatting with an older woman who lived a few hours away south, and he also helped a young college girl with some science problems and continued an online friendship with her for years.
Donnie frequented a local gay chat that he monitored as there were gay men, in a city just 30 minutes away looking to hook up. This was way before apps that you could swipe your way to a hookup and Donnie chatted up to the point that he had to do something about his curiosity, then he'd back away.
He often would find someone in the chat and flirt with the idea of meeting up at a driving range, or workout facility. Donnie had a female hotel worker interested, a nicely curved African American who pulled the plug on him meeting her as he had to work in the city.
One weekend, his wife Mel left to visit her parents with the baby, but because of work Friday night he had to stay back. The next day, it was kinda rainy out so he was online early in the morning. Donnie hit the local board heavy, after a night hitting the random chats and messenger exchanges, getting off twice.
It was late morning and he'd began in the chats again, having gotten a few guys off, when he started chatting with a man from Des Moines with the username DSM0945. He was very engaging and asked personal questions about his curiosity, his body and his profession. It made Donnie very at ease in the way he made it all about Donnie.
DSM0945 asked Donnie if he'd consider meeting up with someone that night and of course Donnie was a little timid. He had started drinking earlier than planned and after getting asked again a little later admitted he'd "considered" the offer and got an address. He was giddy, scared and excited about the thought as they continued to talk.
"I'm actually asking for an older business man, who's wife is travelling" DSM0945 sent in the next message. "He lives in the old money section of town."
Donnie knew where that was from his days living in a suburb of DSM, and was down by one of their favorite blues bars. He chatted about the area, the bar, but the guy wasn't a public guy, that's how much money he had. He talked about how fit the older man was, his 8" cock and that maybe they could golf together after tonight.
"There's a group of guys who like to get younger guys out to golf with them," the message said. "They like to show them off."
"Wow, that's impressive," Donnie answered back, not sure what he felt about that, buzzing from wine and erect from attention.
"Yeah, they pay good money for it too, no real strings attached," It went on. "Unless strings are okay."
Donnie wasn't sure on what to do. He had told Mel he might go into DSM for dinner and maybe to some music, but this was wild to consider.
"Listen, he'd just meet you tonight and give you $250," it said.
They had good jobs, but were a little overextended on credit and things, Donnie hadn't become a good budgeter yet and $250 was a nice sounding number. He got a little courage and responded.
"And what if 'strings' were included?" He dared to ask.
"Oh, you're just curious, I wouldn't push it and he likes companionship," The message pushed back surprisingly. "There's no rush."
"I like his size," Donnie continued to push. "I've had experience with my friend who was 8""
Donnie went on to tell him about his experience with his friend in college and how he would be up for being naked together and sucking him possibly. "If drinking, I'm sure that would work."
"You're sure?" the message asked."He's about 8", thick and again he's very fit."
"Positive," Donnie quickly responded, his cock hard with excitement, he'd been ingesting his pre-cum as it went hard, soft, hard, soft, hard like a pump for the sweet fluid. "I'm in good shape and this sounds wonderful."
"If you're both naked and you perform an act, we're talking $500 minimum and he's a good tipper if you're going to hang around, clean him, swallow, that kind of stuff."