His dick tasted clean, but there was a manly scent to it. I breathed deeply through my nose as I engulfed the fat bulbous head, taking as much of it in my mouth as possible, swirling my tongue around the head to coax forth his seed. I was kneeling on the floor in front of Mr. George at this point, as I felt Jamie's mouth on my rosebud. He was rimming me again, and the feelings around my tender hole were amazingly intimate and arousing. I moaned around the cock in my mouth, adding those vibrations to the blowjob I was giving.
Jamie's mouth pulled away from between my cheeks, but quickly was replace by the head of his penis. There was no preamble, just a slight push as his dick slipped into my boi pussy without resistance. I wanted him there, dammit, its where cock belonged! As he started penetrating me, he would push me further onto Mr. George's cock...deeper and deeper it would go, as it started entering my throat. I fought back the urge to gag, pulling from my training at he gym, relaxing my throat and accepting the cock to be there. It wasn't easy, it took a lot of focus, and sadly that focus pulled away from my pleasure. At least my two lovers were enjoying themselves, that is, if their moaning was any indication.
Jamie stopped pounding away at my hole and said, "Mr. George honey, you want to give this new pussy a try before it gets ruined? I assure you its about the best its ever going to be! This slut is just constantly begging for bigger and bigger, he's a real slut boi." He giggled and laughed at his own statements. Cute as hell, but discerning a little talking about my asshole getting ruined. In my current situation, I was far too horny to care about any of that, I simply wanted to be fucked into pleasurable oblivion. Mr. George's hands pulled my mouth off his cock as Jamie's exited my butt.
I couldn't believe how hard it was to move, I was almost fucked into this position and my body didn't want to move. Mr. George and Jamie simply changed places, and my mouth immediately went to Jamie's little dick, taking it into my mouth immediately, not caring where it had been at this point. Mr. George started poking at my back door, pushing and prodding trying to fit. Eventually his impatience got the best of him, as he started forcing his wet cock head into me.
Just as it breached my boi pussy, my mouth flew off of Jamie's cock as I screamed, "oh....my...GAAAAAWWWWWWWDDDDDDDD!!!!" Jamie just laughed, and stuffed his dick back into my mouth, me trying to talk and moan around it. Mr. George was hilted inside me at that point, just sitting there letting me adjust to his size and shape. It felt titanic in size being larger than my plug, and it felt incredibly slick as I then realized Mr. George added lube to allow it to fit.
Mr. George started moving after a few minutes, and the feeling of stretching pain and p-spot pleasure were combining in the most wickedly seductive way. I would wince at the pain, but moan at the pleasure, over and over again these two dueling feelings would wash over me. My hand was on my caged penis then, trying to tug it and feeling the sheer volume of precum that had leaked out of me at this point. Everything was covered in the wet slickness, it dribbling out almost every time the cock penetrated me.
Eventually the burning sensation of the stretching of my rectum ended, and the only thing left was a numb sensation of the cock gliding in and out of my ring, with the pleasure being forefront now as my prostate was poked and prodded into submission by this man's cock. As I worked away at Jamie's cock with my tongue and mouth, I could feel him engorging as his balls pulled tight up to his shaft base. I knew what was coming as I slid the head of his cock to the entrance of my mouth. He started spurting his sweet tasting femboy seed directly onto my tongue.
Savoring that flavor for as long as possible, I finally had to swallow to allow me to breath deeply as Mr. George started pounding more forcefully in and out of me. Deep thrusts followed by his head almost exciting my body before being slammed all the way back in again. I could feel my asshole stretching just a bit further again as Mr. George's cock was engorging now as well, and then with one final slam, he started spurting his seed deep into my bowels, filling me with that warm feeling of his semen spilling out and trying to make me pregnant.
All three of us breathing like marathon runners, covered in sweat and sin. My ass pussy was quivering, pulsing, opening and closing down on Mr. Georges softening cock, and as he withdrew from me, I could feel some of his load come spilling forth, the escape of air and seed making disgusting noises. Mr. George and Jamie just laughed, my big dicked suitor just slapping my ass and calling me a good slut.
They both got up and were talking to one another, I didn't really understand anything said as I just sat there on the floor leaking cum after rolling myself over to sit down. I did catch a glimpse of Mr. George handing Jamie a number of bills. I realized what I should have known earlier, that I just basically performed my first act of prostitution. I knew deep down what Jamie did for money, and now I did it too, I sold my body for money. I couldn't believe how much of a slut I was, a whore and a slut.
I weakly started getting up and went to the bathroom. I sat on the toilet to pee and expel what I could from my backside. As I wiped up with toilet paper, feeling around my hole and realizing it was barely closing. It was very hot to the touch and tender. I knew it would be sore in the morning. I could easily fit three fingers in my now gaping hole, with just about zero resistance. I wanted to puke at how disgusting I felt, thoughts of having to wear diapers the rest of my life uncontrollably entered my mind.
I got back to the living room to find Jamie and Mr. George having another drink, conversing and laughing together. They had dressed themselves, and their eyes fell on my crestfallen face and naked body, concern filling both of them. They swooped over to me, lovingly holding me and telling me it was all fine, and not to worry. It was natural for the boi pussy to be too worn out to close tightly right away, but it would, etc. Feeling reassured by their words, I got dressed then and thanked Mr. George for the good time, kissing him on the lips, and meaning it.
The ride home with Jamie was quiet, I didn't want to talk as all the thoughts of what had occurred ran through my mind. I was still aroused, but didn't see any way to get release while caged after what had happened. I didn't want to mess around with my backside at his point, too scared of it being gapingly open the rest of my life. Jamie laughed at my concerns, but told me he understood, telling me to leave the plug out for tonight, letting my hole rest up would be a smart move.
Instead of parting ways, Jamie followed me into my apartment. He explained how it works, what he does. Basically, he advertises online, but only in very specific, legit websites that require payment to join. This ensured legit offerings for those that sought them out and it ensured serious suitors for those employed on the website. It was win-win, sort of like a digital pimp.
After he finished with his explanation, he handed me $300, explaining that was my share for the evening. It was a lot of money for such a short amount of time and effort, I thought. Further, I had enjoyed earning it! I made about $1000 a week after taxes with my job, and in this city that was basically nothing. My monthly rent and cost of living was about half that, and it took me over 40 hours a week to make it. Apparently, I could make that much a week with just over 3 hours of work. It was an interesting thought, to say the least, thinking of the volume of money I could make with doing just 20 hours of work a week at this new trade.
Jamie broke me out of my reverie, as we showered together and went to sleep. Between the alcohol and sheer volume of my day's activities, I was too exhausted to worry about my arousal and quickly found sleep in the arms of my sweet little Jamie. No thought of what had changed in me these past few days, no care of being basically gay now. A dreamless night passed, resting my body for the weekend.
I awoke Saturday morning to find myself alone. Jamie had apparently gotten up early, made breakfast and left me some, and then went about his day. I assumed that he had some early morning clients to deal with or something. Weekends seemed to be his busy time, as the first time I saw him in the woods sucking cock was on a weekend.
After getting up and eating, I started my routine and was flushing myself out at the toilet as was now usual. I was curious of the outcome from last night, the lasting effects, and I felt around my asshole then to ensure its status. The good news is it was shut, not gaping open. There was resistance when I pushed and prodded with my finger. Sure, it slipped inside but if I concentrated on clenching up, it was nice and tight again. This relieved me and made me feel a lot better, again making me marvel at the adaptability of the human body.
After finishing up, I sucked on my butt plug to lube it up and slipped it back into place. My ass was sore, but the plug was helping me with accepting my new position in my sexual life, ensure I could take bigger cocks up my ass, making sure it was as pleasurable as possible for me, and it appeared my body would recover from these sessions. It filled me with a new level of confidence, to not be so scared about cock in my ass. I know, weird to think and feel that way, but it is what it is.