(Note: All of the characters in this story are fictional, bearing no resemblance to anyone living or dead, and they are all at least 18 years of age.)
Tony Gilbert hadn't had a decent piece of pussy in several days. His last sexual encounter (with long-time girlfriend Margaret Cameron) consisted of more-of-the-same. Of late their sex had become marital, that is, on schedule and without variety. Tony was well acquainted with Margaret's primary sexual orifices by now. Both of those holes soaked in gallons of his seed.
Like his friends, Tony had some pussy on the side, indeed, at one point Margaret had been a member of Tony's othersnatch harem. Now, as his regular girlfriend, Tony took every opportunity to step out on her. In this wise he was little different than his contemporaries. Tony's seraglio consisted of Margaret, Ch'hiya Sakai, Rosanne Peraino, Donna Dennison and GeorgeAnn Vachetto. Occasionally, Tony hooked up with Dana Chandler and Jonna Kindler, though these latter trysts tended to be few and far between. Both those girls had seraglios of their own.
Margaret knew Tony was cheating. She did her best to drain him, leaving him without the time and/or energy for othersnatch. At the same time, Margaret tended to her duties as a part of Delphia's crew. She fucked other boys at Delphia's behest. Margaret didn't consider this behavior to be "cheating". To her, this behavior was merely paying dues for membership in the club.
On the Thursday in question, Margaret, Ch'hiya and Delphia triple-teamed Kurt Kuhlmann in the school auditorium. Delphia bet both her friends that they couldn't make Kurt cum. She offered a twenty to the girl that managed it. None of them did.
Delphia assured her two friends that she would successfully take Kurt away from his girlfriend Denise. She bet a twenty on that, too. Margaret didn't say anything, but she doubted it. She'd seen Kurt and Denise around town. They looked like a happy couple.
Margaret recalled her earlier congress with Kurt. He'd been mechanical, seemingly unaffected by her vaginal charms. They'd fucked doggystyle. His penis was thicker than Tony's. He'd fucked her through several searing orgasms, but his detached authoritarian manner put her off. Delphia liked it, though.
In any case, Margaret didn't feel up to fucking Tony that day. Her pussy was wrecked. She thought Tony would notice. This left Tony with a three-day window since his last orgasm. He was either going to fuck or wind up with his dick in his palm.
Early that Thursday evening Tony retired to his bedroom. Using his cell phone, he called Rosanne Peraino. They chitchatted for awhile before Tony got down to brass tacks. He needed some pussy. It being a school night and only eight degrees outside, there was no way Rosanne was going to leave her comfortable home just for a piece of ass. Rather, she described her craving for dick, his dick in particular, and told him what she'd do with it, if only it had been in reach. Tony mentioned how he'd like to yank her ankles into the air and fuck her blind. Rosanne admitted that she'd like nothing better, but first, she said, she possessed a nice esophagus, with a big clit in it, that required his immediate attention. This led to a prolonged conversation of intrigue and fantasy, ending when both of them collapsed under their strident masturbatory efforts, Tony's stomach and chest covered in jizz, Rosanne's penis-shapped dildo sweaty wet with punani froth.
Later that night, very late, Tony awakened abruptly with a raging hard-on. This was not unusual. He was nineteen years old. He hadn't bothered to wipe the jism away from his torso. Now it dried and felt all crinkly between his nipples. Tony realized that this boner was not going to subside on its own. It needed the wetness and swelter of a vagina to achieve a measure of succor. Tony stroked himself diffidently, already knowing the solution to his problem, always wondering if the solution was worth the risk.