Mary Ch. 01

If you're squeamish at all I suggest you find something else to read. This story involves abuse, bondage, homosexuality, transgenderism, and even non consensual sex, as well as gang bangs and prostitution. It is a dark and twisted tale only for the most jaded individuals. You've been warned.

All characters are over the age of 18

- Part 1 -

It was a warm Friday night. My wife had gone to her mothers for the weekend and took the kids with her. She hated me so I usually got away with staying home those weekends. That meant I'd have until Sunday evening to myself.

Laura and I stopped having sex about six months ago. The sex wasn't super often before that either but now it had completely stopped. It bothered me in the beginning but now i had restarted an old hobby from when I was younger.

Ever since I was younger, I'd sneak into my big sisters room and wear her bra and panties. This continued until she caught me in her room dressed completely in her clothes. She had told my parents and I was severely punished. It didn't stop me, I was just more careful to not get caught. As Arnold I was soft and sensitive. Being Mary, I was everything Arnold lacked the courage to be.

I stopped crossdressing when Laura caught me wearing her panties about 7 years ago and never looked back. I shoved Mary away in the attic and left her there. I continued shaving all my body hair, some things are just too hard to stop. I love the feeling of smooth legs touching smooth legs! But now that the sex had shut off, I picked back up where I left off.

I got a step ladder and jumped up in the attic to retrieve the suitcase with all Mary's clothes. That was my name when I dressed up as my alter ego. She was everything I wasn't. Where I was shy and reserved, Mary was bold and outspoken. She allowed me to be the version of myself I couldn't be in real life.

Mary didn't like to fuss too much with clothes. She decided to glue her big DD tits on and not wear a bra that night. She did put on tight thong panties that she tucked my cock into and my balls were pushed inside my stomach. She then dropped a sparkly halter neck dress over her head that hugged every curve on her body and stepped into a pair of 6" black high heels.

She had her choice of a couple different wigs. A blonde one that was super curly like orphan Annie, or a straight black one that looked like Lucy Liu's hair, or one that looked like tinsel on a Christmas tree. She flipped the tinsel wig on her head and applied dark Smokey eyes, and a bit of blush. Then carefully drew in eyebrows and lipstick topped it all off.

She stood looking in the mirror. She looked like a man in a dress but if she turned the light out and looked at herself using the glow from another room, she looked completely like a woman. That's all she needed to get what she wanted!

Mary drove up the winding mountain road to an area she frequented before her Arnold got married. She would have long nights of carnal pleasure in the woods near the city overlook with countless men and sometimes even women.

It had been many years since she had been there and it looked deserted when she got there, but she was all dressed up and wanted to remember how it was to walk in heels anyway.

She stepped out of the car, locked the doors and placed her keys in front of the passenger tire with a rock hiding them from view, then walked off into the night in the direction of the old abandoned mill.

She loved the air on her smooth legs and the sound her heels made crunching in the gravel. Her tits bounced with each step and she felt powerfully feminine in the darkness of the woods. She decided to walk to the mill and wait for 20 minutes then go home if no one showed up.

She leaned back against a wall and looked at the city lights. She was cupping her breasts in each hand when the first guy walked in to the mill. She couldn't make out his features but he was short and stocky.

"Hey baby, you looking for a good time?" The stranger asked.

It was a rhetorical question. He knew she was looking for a good time! In her best fem voice she said

"Whatcha want?"

He pulled his prick free and stepped in close. She didn't waste much time. She grabbed ahold of the dick and started tugging on it. She had forgotten how nice a cock felt in her hand. The stranger smelled nice, but she really didn't care what he smelled like. She just wanted his dick.

She crouched down onto her heels and placed her mouth over the man's cock. It was warm and easily manageable at 5" long. It was hopefully a nice warmup for the evening. Mary didn't hold anything back as she took the dick all the way into her throat and started licking the man's balls with the cock buried in her throat.

The stranger couldn't handle a girl that could deep throat and still lick his balls, and he erupted into her throat. She pulled back and sucked on the tip of the man's cock head until he pulled it free from her grip. She held the man's cum in her mouth, playing with it, letting it coat her mouth before tossing it back and swallowing it as he walked off into the night.

Two more gentlemen had arrived and were just watching the show as she finished up. With the taste of cum in her mouth, she was hungry for more. She stood up and pulled her dress back down over her crotch and stepped between the two men. Both had their cocks out and were stroking themselves. She was waiting for one of them to decide. She would get them one way or another, she could wait.

The taller of the two approached first and she bent over to take him in her mouth. His prick was bigger, about 7" long and so thin she didn't have to stretch her jaw to engulf his dick. She held her head still as the man grabbed her head and started fucking her mouth. She had to time her breathing with his thrusts. When his balls rested on her chin, she would cough and gasp for air as he choked her with his prick. She loved the roughness of a good face fucking.

The shorter shy guy turned out to not be so shy. He lifted Mary's dress and pulled her thong aside. He spit right on her asshole and placed her cock head right at her hole. Then he grabbed her hips and timed his first thrust with the guy in her mouth. When the tall guy thrust into her mouth, the short guy buried his cock in her ass. She wanted to scream out but her mouth was filled to the brim. She was getting slammed in unison from both ends. Light danced in her peripheral vision as the pleasure of the situation took over.

The pain of being forcibly fucked from both ends filled Mary with the pride that she could still take two men at the same time, and that she was still desirable enough to coax the cum from her company's balls.

She felt someone else place a cock in her right hand and she started tugging on it. It was the first uncircumcised cock of the night. They were easier to jack, fuck, suck, and take in the ass than their counterparts. She wanted him to stick around. It was a good 10" and thick. She wanted to have that cock inside her.

The guy in her mouth quickened his pace and she felt his impending orgasm building just before he pulled his cock free and sprayed hot jizz all over her face. She tried to catch as much as she could in her mouth but he just wanted it all over her face like he was marking his territory or something. She wiped as much cum off her face as she could and scooped it into her mouth just as another dick was placed at her lips.

The short guy behind her tensed up and shot his load. He had to be wearing a condom because she didn't feel the unmistakable sensation of cum flooding her bowels.

The big uncut man stepped behind her and pushed his cock into her slowly. He was truly a gentleman, allowing her time to get accustomed to his size. The boy in her mouth nutted in under three minutes and she was left alone with the big cock in her ass.

He picked her up and walked her to the missing window overlooking the city. She was set over the framing with her body hanging outside the building. He used the building as his leverage and he started pounding her little ass almost shaking the whole building around them.

They fucked like that for almost 10 minutes when he pulled out and grabbed her by the back of the neck.

"Hey, what the fuck are you doing!" She yelled.

He was a huge black man by what she could see in the darkness. He had produced a small length of rope and tied her hands together behind her not saying a single word. Mary was just an inch from his stinking cock as he was tying her hands. She thought if she could just get him to nut, he might lose his interest in trying her up.

She reached out and took him in her mouth, she could taste her ass and possibly some blood on his cock. Her ass sucked in cold air as she filled her mouth with his big black dick. She had a hard time getting him all the way in her mouth from that angle, if he'd just quit with the sucking ropes!

He fiddled with the knots around her hands for a moment and pulled her up backward by her arms causing a pained cry to escape her lips. He picked her up as though she weigh nothing and set her in the center of the room. He then tied her hands to a rope hanging from the ceiling all while she was kicking and screaming.

She was pulled up so that her torso was level with the ground, her head and mouth was right at crotch level and her ass exposed. He leaned in real close.

"If you don't shut the fuck up, I'll gut you like a pig, then fuck your brains out and leave you to die bitch!" He whispered in her ear.

Mary didn't make a sound after that. She knew better than to fuck with the big guy in her present situation. Her captor left her standing, strung up in the middle of the mill. He posted up at the entrance only 20 feet away and started selling Mary's body. $20 would buy her ass, $10 would buy her mouth, and $5 would get a hand job.

Mary was captured, in danger, being sold off like some sex slave, and horny as fuck! She was pulled up so high that she was teetering on her high heels and one slight misstep would cause her to fall into her arms, wrenching then further back into an even more painful position.

The first man he sold her ass to was quite rough. He spit right on her anus and shoved his cock in forcefully. Every 10 or so pumps, he would slap her ass hard causing her to jump and squeal. He would just laugh and continue fucking.

Within the first 5 minutes, She'd already made the big black man $40 and there was already a line forming. Mary felt so hot, and desirable, but the situation was fucked up. She would have done all that shit for free. Hell, she would have let them tie her up. It had happened before but something felt different about this guy. He didn't even finish when he started fucking her the first time.

Some guys came in and were really gentle with her, while others roughly fucked her face and ass. I lost count of the cocks She'd serviced throughout the night, and we even passed out once when someone choked her as they fucked her throat. It was both super hot and scary at the same time! she'd had what She thought was rough sex before but this was a whole different kind of rough sex. She loved it!

The sun was just rising up over the hills as the last two men finished in her mouth and ass. She didn't know how much money she'd made him but The was a fat wad of cash stuffed in his pocket. He came and cut her down. Holding her under his arm like a small child he carried her out of the mill and into the woods.

The air was cold and prickled her skin into goose bumps everywhere. When we passed my car and continued on to the only other vehicle in the lot, I started kicking and screaming.

"Hey, let me go, god damn it!" I yelled.

He dropped me into the back of a pickup truck and punched me right in the gut. I folded in half and groaned loudly. He ripped her panties off and stuffed them in her mouth, then stuck a piece of duct tape over them.

As Arnold I was scared shitless. I couldn't take it I need to get the fuck out of there however I could. Mary on the other hand seem to thrive on that shit. Her cock was poking straight out and leaking as the big black man tied her legs together to her hands. She was hogtied and pushed roughly into the back of the truck. He closed up the tailgate and drove off.

Mary lay bound and completely helpless in the back of his truck. Her tinsel wig blew around her face in the breeze, and her dress was hiked up over her hips exposing her ass and cock. He wasn't really careful in the way he drove and so she rolled a few times from her right across her belly and onto her left smashing her cock painfully underneath her. She slid from side to side as the truck drove through the mountain turns at a dangerous pace.

We slowed to a stop at a red light as we enter the city. A street lamp lit up the entire intersection, Mary included. Mary looked up at the driver of large red dump truck, and to Arnolds horror she winked at him as sexy as she could from someone who was hogtied and gagged.

What the fuck was she thinking! Arnold screamed inside his head. That was someone that could help us escape, but Mary was still laying there trying to get her fucking rocks off.

It's strange, four different people saw us laying there, and not one did a thing to help.

We pulled to a stop and parked at the edge of an out cropping of tall buildings. Mary could see many lights on and TVs flickering behind curtains. Mary guessed they were in the housing projects.

The man got out of his truck and walked around to the back. He dropped the tailgate and threw a blanket over her, then dragged her out to the edge by her feet. He leaned in so close to her face that she could smell the cigarette he just finished.

"If you make one sound I'll cut your throat and drop you right here bitch." He whispered harshly.

And then he picked her up and stuffed her under one arm and carried her into the building. Mary could see the yellow painted lines on the asphalt and then the sidewalk just before she entered the building. The black and white checkered linoleum tiles looked like they hadn't been cleaned since they were installed.

They stopped and she heard the unmistakable ding of an elevator opening its doors. They rode on the elevator for a long minute. Mary could hear the elevator cable stretching and pinging under the weight. They stepped out and walked down a hallway of red carpet that had been stained black over the years and was burned in several places by what looked to be cigarettes carelessly tossed aside.

They stopped at a brown door. The threshold was missing and she could see light pouring out through the bottom of the door.

!Bang bang bang!

Mary's body shook as the man pounded on the door. The ropes were digging painfully into her legs and arms. She had a serious cramp in her right leg, but her cock was still poking lewdly straight at the floor and leaking. Mary was built for this, anytime someone got a little rough with Arnold, she would step in and make sure he didn't get hurt. She pushed Arnold back as far as she could, he couldn't handle anything that was probably about to happen.

"Who is it?" A voice replied weakly from behind the locked door.

"It's Adam open the fucking door cunt!" He yelled.

Mary heard three locks and possibly two chains before the door popped open and swung inward. She counted 20 seconds from when the first lock was clicked to when the door opened. 20 Mississippi's was how long it would take her to get out once she was inside.

She had twisted in his grip and was now pressed painfully against his body. His arm dug into her ribs as she was being bent sideways from her own weight. Her cock pressed hard against his thigh. Her panties were soaked with spit and the tape was pulling painfully at her cheeks.

He grabbed the rope connected to her arms and legs and set her on a table like a piece of luggage. Without warning he ripped the tape from her mouth and pulled her panties free. Her dress was hiked up high above her hips and her erection was stabbing into the table. He pulled his 10" monster out and placed it right at her lips. He waited until Mary opened her mouth to take his cock in her mouth.

Adam grabbed ahold of her head and started fucking her face like a woman's pussy. She forced her jaw open so her teeth didn't drag over the tender flesh in his tool. It went on for what seemed like an eternity. He would occasionally pull his dick free to slap it on her face then forced it back into her throat. Tears and saliva were steaming down Mary's face when she felt the first shot of hot bitter spunk land on her tongue. Then he buried his cock in her throat and fucked deep until she passed out.

Mary was carried into a room and dropped on the floor in a heap.

"Get her ready, I want her out working tonight!" Adam said gruffly.

She heard the door close just as she started regaining consciousness. She lay hogtied in a dimly lit room with four other people. There was a bathroom without a door, a nicely made bed with stuffed animals and a computer directly across from the bed with a video camera and lights set up to the side.

The girl nearest said hello.

"Hi, I'm Tiffany, what's your name?" The skinny black trans girl asked.

Mary looked her up and down and in a split second noticed her feminine looking face, her uncovered size D breasts with small nipples that sat a little wide and her enormous cock! She wore a small black cock ring with little pink jewels around the perimeter. She was sitting rather strangely. It was as though she knelt down and fell sideways onto her ass cheek.

"Hi there, I'm Mary." She said quietly.

Three of the four seemed to be sleeping, and she didn't need to be starting off on a bad foot with any of them.

"What is this place?" Mary asked.

"This is Adam's place. We his sex slaves. We do what he say when he say it, or we get punished." Tiffany said.

"What kind of punishment Tiff?" Mary asked.

Tiffany pointed to the small black ring around her cock and balls.

"There a perimeter sensor. If we pass it, we get shocked. Adam also have a remote to shock us if he want." Tiff said.

"So if I'm going to get out, I need to remove this first?" Mary asked quietly.

"He'll just fuck you up. Best to not even try. Accept it, you a slave just like all us too!" She said.

Mary could play the part for as long as she needed, but one day she would get out.

"You can go shower, I'll make you up a bed. You look exhausted." Tiff said.

Mary got up and rubbed her wrists. There were angry red welts where the rope dug into her skin. She was glad to be free of the hogtie. She stepped into the shower and started washing all the dried cum, and grime off her body. The water was turning a disgusting brown color as her body turned a soft pink from the hot water. At least she had hot water with great pressure! She inspected the cock ring clamped around her junk. There were charging leads. That meant it would have to come off to be charged.

She stepped out and dried off. Her fake titties fell off from the hot water of the shower and she held them in one hand and the other held her towel around her waist. It wasn't big enough to wrap all the way around herself and tie up though. She dropped the towel into a pile with a couple others and stepped back into her soiled dress.

Tiffany had laid a blanket out on the floor. The other three were sleeping on the floor as well. They were covered up but she could see one was a pudgy little Mexican kid in his 20's another a tall looking t-girl in her 30's and the other a short cute looking blonde girl maybe just turned 20. Mary it seems was the oldest in the group at 40 years old.

"Thank you, why doesn't anyone sleep in the bed?" Mary asked laying down and pulling the blanket over herself.