This is a work of trans sexual fantasy, with mutual enthusiasm but without explicit discussions of consent. Though words like cunt, pussy, clit, womb, dick, and hole are used to describe the trans man's body, they are not intended to be read as feminizing. Just a heads up if that is not your thing.
~Horny reading!
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Late Thursday afternoon, John found himself staring at the ceiling of his living room, alternating between profound guilt and overwhelming horniness, when a Venmo notification dinged across his phone screen.
"Request for Payment: $45 -- Plan B from RileyBoyH"
The guilt and the horniness both won, immediately accepting the request, John pulls his now fully hard dick free of his sweatpants - violently hating himself for the entire 30 seconds it takes him to cum forcefully; ruining his pants and shirt in the process.
"Goddamnit" he mutters under his breath, "this is what you get for fucking a random college student with no protection, dumbass." Frustrated, overwhelmed, and disappointed in his failure to control himself yet again, John pushes up off the floor to run his soiled clothes through another unexpected wash cycle for the third time since Tuesday night.
~
By Saturday evening, John is resolved to clean up his act emotionally. He'd spent the rest of the week tormented by memories of Riley' s hard dick and wet cunt, the sound of his grunts, the way his moaning voice would break. More importantly, he reprimanded himself, John couldn't excuse the way he basically made a wordless getaway once Riley's parents came back from their date night. He had left the 19-year-old to figure out contraception alone, not engaging in any of the finical or emotional support he always prided himself on providing all of his previous, though less spontaneous, partners (who had all been women) (God he was so wracked with guilt that he'd had no time to figure out what this meant for his sexuality) (because Fuck did he want Riley as a man and Fuck did he not deserve to pursue that boy).
It was clear Riley was not interested in getting to know anything about John. The Venmo meant he knew John's number but there had been no follow up text.
Trying not to spend any more nights pointlessly hoping for a text that would never come, John reached out to his buddies to see if anyone was up for something this weekend. Turns out his friend Mike, who John hadn't seen since celebrating his 25th, was now assistant coach of their old high school football team and tonight was the homecoming game. A bunch of their old teammates were pulling through and John should join them.
By 8pm, John found himself waiting in the concessions line just before the half-time rush. Glad for a busy evening filled with familiar friends and football, John had just finished placing an order for his second pizza when his phone buzzed. Thinking it would be a food or drink request from one of his friends, he pulls the iPhone from his jeans, freezing in place when he sees that an unknown number had sent him a photo.
All thoughts of friends and food knocked from his mind, John hurries behind the bleachers as he tries to type in his passcode, failing twice with shaky fingers. Could it be him? Making it to a secluded shadow, John finally opens the image, blood and the sound of a marching band roaring in his ears.
There was Riley. Sitting on a toilet, pants and boxers around his ankles, knees wide to give a clear view of his drooling pussy and angry little cock. John couldn't think. He couldn't breathe. He was trapped, immediately straining against his jeans.
In response to his read receipt, a typing bubble pops up. John almost cums right then and there.