Author’s note to the reader: The objective writing this story was to capture a really seedy and sordid encounter involving a few men and a transsexual prostitute. The story is sexual in theme and could be considered erotic by some, but it’s also pretty dark and bleak. You have been warned…

I wasn’t sure I remembered the last time I had seen Crystal straight. She hadn’t hit bottom yet, the psychosis and lunatic paranoia that would come to dominate her life as much as the meth was only hinted at now.


Crystal was a prostitute, a transsexual with enormous silicon tits, tummy tuck scars and all the tricks a transsexual uses to fool her traitor biology, paid for by curious men like me. She’d been pretty cute years before, when we met I was no more than 19 or 20, I guess. I’d been playing with my own ass since I was barely more than a teenager and I had recently become obsessed with the idea of getting fucked anally. I thought of myself as a straight man then, and a shemale had seemed like a suitable compromise – easier than to ask a straight girl, less “gay” than a man.

I visited her one night, money changed hands. I sucked another person’s cock for the first time, received my first real buggering, and felt her spill her seed on my 19 year old back. Later that night I cried with anguish and shame, the next day I masturbated to the memory of it.

Nearly 10 years passed and we met up again, I had not been idle in that time, my insatiable thirst for sensation had led me down dark and unscrupulous avenues and alleyways and whatever part of the soul in which guilt or shame reside had long since developed a near impermeable scab. She remembered me, “I came on your back”. Now, both of us older, reacquainted as friends with benefits, she still tricked, but I didn’t pay, most of the time we just talked.

Nearing 30 and after a 15-year diet of internet porn, I viewed regular hetero sex with a degree of ambivalence normally reserved for dry toast. My interests ran the spectrum of typical extreme porn from fisting, to pissing. One-on-one male-on-female porn was like light beer, what was the fucking point? A dirty minded or pliable woman can be persuaded to try most things and so given time and the right (or wrong) women I was able to emulate most of the porn that still titillated and there was little I hadn’t experienced.

But I was still transfixed with cock, big porno-sized cock. I was lucky enough to be reasonably endowed but, watch enough porn and you’ll soon feel like the only guy on the planet with a 6 inch dick. To Crystal it was all “just cock”, I guess you dine on truffles three meals a day and pretty soon its all “just fungus”.

The night in question we’d been talking about big dicks. She was blasé about it (as a whore will be), but she was intrigued by my fascination, in the tiny remnant of her psyche that wasn’t consumed with the need to find and smoke more rock.

She was going to have some guys over, maybe have a little party involving her favourite customers and dealers. She’d left me upstairs watching porn, straight porn, she hated shemale porn and that was what most of her clients wanted. She had bought a small bag of speed, and not wanting to be left out I’d chipped in half the money.

She showed me how to smoke it out of a busted light bulb. I’d tried a lot of other drugs, smoked dope semi regularly, took a lot of acid and the occasional E in my younger years. Ice was a bit like E I guess but with a dirty feeling, a real low down dog undertone to it that made you feel sleazy and dirty. Maybe that was just the environment or my preconception of the drug, or the way I’d seen it change Crystal.

She was on the phone trying to source more Ice, and simultaneously trying to find clients who might be wiling to come over and sponsor her next bag. I was upstairs alone and high, I’d taken a Viagra as well (one of hers) and had a pounding headache to go with the thick hot feeling of speed in my blood, for an hour or so I just watched porn, wondering why the hell I was even there and becoming increasingly frantic with horny desperation.

I heard people come and go downstairs, arguments on the phone, the wonders of doing business with dealers. And then some older guy came up the stairs with Crystal, she introduced us briefly before returning downstairs he wasn’t good looking in anyway, very forgettable I guess since I don’t really remember much about him, portly I think, my impression was of a regional branch bank manager. A few minutes later the same thing, another guy, this one older still, maybe 50 or so I guess more wiry probably, grey hair I think but in the dark room it was difficult to tell, and in these situations you don’t spend much time looking each other over..

None of us really spoke, we’d all come to see Crystal and she was the only one not there. So we just watched the porn in silence, the older guy and I smoking from the bulb until the measly stash was gone. The atmosphere upstairs was like a porno theatre, dark room, people fucking on a big screen and complete strangers all wanting someone else to get their dick out first. Emboldened by the drugs and the hour or so of porn I had already sat through, I broke the masturbatory Mexican standoff and unzipped my fly, pulled out my erect sweaty penis and started playing with myself.

Sure enough within minutes the two older guys did too. I immediately noticed that both guys had big dicks, the reasons for Crystals choice of guest became clear. We all sat there jacking away, I was sitting toward the back of the room was able to stare hungrily at their dicks without them really noticing, their eyes focused pointedly at the screen.

The guy sitting on the couch beside me had the smaller cock of the two, still bigger then mine, probably 7 or so inches, cut and fat. He was right there and had his dick out, and I was horny and repressed. And high. After a while I quietly mumbled, “Do you mind… do you mind if I suck your dick?”.

“Err, OK then”.

He slid forward a bit to give me better access, and I lowered my head down on his cock, and began by tonguing the shaft and his heavy hairy balls. I quickly got into it and after a while moved onto my knees between his legs to allow me better access, (and so my body wasn’t pressed against him any more than it needed to be). I gave him by best impression of a porn star blowjob, and became more daring as I warmed up. I gripped him around the base of his cock with one hand and played with myself with the other.

I felt him tensed and begin to moan softly, he began thrusting into my mouth. He never touched me with his hands; I guess that might have been a bit too gay for him. Strange little rationales we make with ourselves. When he reached the point of ejaculation he shot into my mouth, by reflex he reached out then and held my head down on his dick, but no sooner had he finished spurting then his hand pulled away quickly.

He mumbled a thank you, zipped up his clothes and quickly left without looking back.

The older guy was sitting on the other couch, he was still jacking away watching the screen, his dick was uncircumcised as well but very long, it seemed thinner because of the extra length but it was thick, and the large head bulbous and mushroom like. As I turned to him, still on my knees he made the same motion the first guy had, slid forward slightly and parted his legs.

Without standing I moved over to him on my knees. His cock was big, bigger then the few real ones I’d seen in real life, I spent a long time paying homage to his member. Really making a go of it, I sucked him for ages. After a while I sat on the couch, and he straddled my thighs, and fucked my face with steady firm strokes for a while longer. I masturbated myself between his legs, delaying my own cum, knowing that if I ejaculated before he did I would flee the house. It’s always in the aftermath of ejaculation that I feel the moment of regret and I knew it would come on strong and hot after this little escapade.

When my jaw began to ache from the prolonged face fuck I took him in my hand and jerked him, enjoying the feeling of this stranger’s long fat member. Without looking up I mumbled, “Would you fuck my ass?”.

“I’ve never done that.”

“Would you do it though?”

“I don’t think so”.


He hesitated for a while, neither of us willing to meet the other’s gaze.

The coffee table was littered with ashtrays and bongs, plastic baggies and a bottle of lube or hand cream, I squirted a large quantity into my hand and coated his dick in the slimy liquid.

We pushed the heavy coffee table away from the couch, and I knelt on the floor, resting my chest on the couch. He moved behind me, stroking his lubed cock preparing it for me.

As the man, pushed the head of his dick against my anus and gave a few preemptory pokes at the tighter outer ring, Crystal, having apparently exhausted all avenues of sourcing more meth came upstairs, tense and angry.

“Hello, what’s going on here?” she asked, her mind temporarily distracted from the disappointment.

She walked over, and flopped down in couch beside me, picking up the remote she flicked the channel. At 2 in the morning there was nothing on except golf. Her attention was torn somewhat between the tv and the two guys preparing to fuck in her lounge room, she gave me a cursory scratch of encouragement on the head like I was a pet that had finally learnt how to use the doggy door.

Old guy began pushing into me slowly, it was a bit of a struggle as he pushed the large head inside me. He grabbed me around the waste and began to fuck into me with a long slow thrust. I groaned as I struggled to accommodate the thick tube of meat that forced me open.

Crystal pulled up her dress and began flopping her stubby little penis around. I positioned myself between her legs and began kissing and licking the inside of her thighs and her tiny balls. She smacked her penis against my face as I worked my way under her balls to lick her perineum.

Crystal was slowly becoming erect, almost despite herself. She had picked up the light bulb crack pipe and had a futile drag on the baked remnants. There was the foul chemical stink but evidently it yielded nothing because she threw it aside in disgust. She placed her hand on my head then and pushed it down on her cock, holding my hair she began pushing and pulling roughly on my head absent-mindedly, focused more on the interminable golf coverage then us.

The old guy had built up a steady rhythm, I was moaning now, the long steady strokes felt incredible as he plunged into my ass. I became lost in the sensations and surrendered myself to the experience, pushing back on each thrust of his dick hungry for the next impalement, alternately groaning around Crystal’s cock and sucking with an unfettered hunger. For long minutes I was lost in my own world and when my foggy consciousness returned I heard them talking. Speaking casually as they fucked me, I’d missed the start of the conversation but they had been talking about me and what had happened while Crystal was downstairs.

Perhaps tipped off by a subtle change in my rhythm or some hooker’s sixth sense Crystal noticed I’d returned to the land of the living again and taking her hand off my head tilted my chin up to look at her.

“Having fun honey?

I nodded, sheepishly between the thrusts, my asshole now so inured to the constant pounding it felt loose and open. Crystal pulled on her dick, shook her head at me amused at my situation. The older guy was changing pace, each thrust slamming in hard staying rooted to the hilt for a little longer tensing, I knew he was preparing to come. I started sucking Crystal again faster and with focus, swirling my tongue around her 5 inch clit, lifting her legs up so she rested her feet on my shoulders, allowing her to push up into my mouth using my body as leverage I cupped the cheeks of her ass, squeezing them hard.

With a long groan the stranger behind me sunk his large dick deep into my ass slamming it to the hilt and I felt it pulse around my twitching abused asshole as he dumped his dirty seed into my bowel. It was enough to send Crystal over the edge and moments later she grunted, and I tasted her bitter cum in my mouth, a small spurt and she was done.

I felt the cock slide from my ass and the guy stood up, disappearing into the bathroom. Crystal pulled her short flannel dress down over her soggy shrunken penis and I knew she was done with me. Feeling suddenly abandoned and self conscious I withdrew, my own erection still hard and dripping I knew this evening’s proclivities had concluded without me. I reorganised my clothing, wiping my mouth and tried to sufficiently restore my appearance to depart with what laughable remnant of dignity remained to me.

I made hasty mumbled goodbyes, and moved in a daze out to my car fleeing to the security of my own home and bed. When I got there I showered, long hot and purifying, the threat of shame lurking at the periphery of my consciousness but more than counterbalanced by the thrill of excitement at the night I had just experienced. In my own bed, warm and clean again but still wired from adrenalin and speed I masturbated for a long time replaying the memories of my depravity. Later, with my own thick and pungent semen drying on my belly I lay waiting for sleep to finally rescue me from my latest deeds and wondering where I could possibly go from here.

Comments are closed.

June 2018
« Feb