Of course, my presence here is just about as mysterious as everything else in this descent into sexual debauchery. I used to be this conservative looking preppy banker. No real hints in my growing up that I wanted anything other than tight blond pussy (ok, maybe with a pinch of ass...), a big house in Greenwich, two dogs, three kids and vacations in Aspen and East Hampton. I never prided myself on originality, just raw determination and the thrill of constant achievement. While life had not always been easy, it had offered me almost everything I had ever imagined wanting. The world was my oyster and I was determined to suck it all down.
So why am I shaving my asshole right now? And why have I started to refer to my ass as my "pussy" or my "cunt"? And for God's sake, why oh why would I ever want to stick a plastic hose in my ass and fill it with water?
What has happened to me?
I am in a hotel in the middle of nowhere meticulously preparing myself for E, according to the detailed instructions he left me the first time we were together. As he was departing my room that first day, he had leaned over my still naked body lightly ran his finger tips from between my shoulder blades down to my crack and softly uttered a few simple directives for the next time we meet.
"You will not have any hair here... or here... and less here."
"You will start working out with a real trainer to build up these and these... I don't like skinny"
"You don't need to bring any more of these... they are for pussies."
"And I want this to be tighter, wetter and ready to take me straight in the next time."
I felt humiliated, being touched like an animal and "appraised" so coldly by a man I hardly knew. Who the fuck did he think he was? And why the hell would I ever want to listen to this fucker? But whatever my brain may have been trying to tell me was over-ruled by the growing stiffness I felt in my otherwise completely ignored cock.
"Yes sir" I uttered for the first of many times.
"Oh yeah" he said as he walked to the door, "one more thing..." and as he opened the door, he casually withdrew a card from his rear pocket and flicked it in my general direction as the door closed behind him. No further explanation.
Stunned by all the events leading up to that moment, I stared at the little card unable to move. I could still feel the trails of his light touch on my body as he given my orders. And now I began to feel the rest of me as well. A slight ache in my throat, scratches on my buttocks, bruises on my shoulders and chafing on my face from where it had been held down on the heavily embroidered pillows. And soon thereafter, the throbbing inside me began.
Oh my god. I had just been fucking fucked by a fucking man. What the hell happened? And not just fucked, but I mean really fucked... by this older guy I had never met before and who had somehow overwhelmed my better judgment as I cruised for a twink online and somehow had gotten into my head and controlled me like some sort of fucking Jedi. Somehow, he had me naked and splayed out on the bed begging him to fuck me. But despite all my begging protestations to fuck me safe, he simply grunted no and forced his himself into me with no fucking rubber. And I couldn't believe the fucker dumped his fucking load right into my ass. What the fuck??!!
I didn't want to move. To move would be to admit this had all happened and it wasn't some sort of sick fucking dream. Movement would have verified that I wasn't imagining the squishy feeling inside my ass. Movement would have allowed me to feel the soreness in my back and butt from where he held me down as he pounded himself inside me.
But as the feelings slowly returned to my body, so too did my cognition of where I needed to be and how late I already was. I forced myself to sit up and immediately wish I hadn't. Now there was no doubt that I had just allowed a man to place his penis inside my ass. I could barely clench the muscles of my previously tight ass, but as I tried, I felt a trace of his cum dribble out and soak the sheet where I sat. I stood up... or rather tried... but my legs had trouble supporting my weight. I limped towards the pile of my clothes which had been rudely heaped into a corner of the bathroom and thru only the miracle of muscle memory, managed to pull on my boxers and t-shirt, allowing me temporarily to believe I was still my old self because I looked familiar in the bathroom mirror.
I paused before leaving the bathroom, briefly considering what to do with my ass. Having never been fucked raw before, it occurred to me I had no idea what to do next. Should I sit and push his cum out? Should I douche again? Could I bear to face the indignation of his wad pouring from my ass? But what would happen if I did nothing? Thinking wasn't coming easily for me, however, and I felt my watch tugging me out of the room and into my pants and shoes.
As I walked towards the door, I saw the card E had left for me still sitting on the floor. I approached it nervously, with a mix of anticipatory dread and inconvenient longing. On the card was simply a name and a phone number. But on the other side, were perfectly formed block letters, presumably written by E: "He will do what's next".
What the fuck was that supposed to mean? Jesus Christ, give me a break... That fucker certainly thinks a lot of himself.
I stuck the card into my pocket and walked out into the bright daylight to look for my car. As I drove back to my office and my normal life re-asserted its hold on me, I started to relax back into the comforts of my life's routines. I remembered my evening bike ride that afternoon, the cocktail party later that night, and the hope that Lori would be there. I sighed deeply and felt my whole body relax into my driver's seat, thinking to myself "everything will be ok".
But even as those words formed in my brain, I felt a small torrent of E's cum work itself out of my relaxing hole and soaking straight through to my pants...
(To be continued)
