Paying For It Doesn't Always Work

WHAT HAPPENS IN RENO...

How in the hell did he get himself in this position? How was he going to get out of it? All these were going through Phillip's mind as time clicked on. It had all started out as an excited business trip to Reno; he had looked forward to for weeks. It wasn't his first trip to Reno, and he had prepared to make this trip as awesome as his last one.

No, it wasn't the gambling that excited Phillip; it was the availability of the ladies. The ladies that would do for you whatever you wanted, for a price. Phillip had a passion, a fetish that he couldn't get quenched at home. He was a careful person, when he left his Hotel in Reno; he left his wallet, his keys including the hotel key in his room. He wanted nothing that would tie him to the alter him. All he did take was $300 in fifty dollar bills, folded up in his pocket, a gym bag full of his fetish needs and a $50 bill under the insole of his right shoe. He was always careful, always prepared.

He had left his motel, bag in hand, and started down the street. He knew from past experience where the street walkers or prostitutes could be found. He spotted one and slipped up next to her. The little chit chat just to make sure he wasn't talking to just another tourist. Yes, she was available, and she started rattling off prices. He held his hand up to stop her.

"I want something specific; I am not looking to get laid." He lifted his bag to get her attention.

"What's your gig she had asked?"

His eyes looked around as one might before divulging a secret. "I want 2 hours of your time. I want you to dress me up, make up and all. I want you to tie me up and spank me for wearing women's clothing."

"Yes, I could do that, no sex, two hours it would be $250. I don't have anything on my person to spank you with."

He raised the bag again. "No problem I have everything we need, except a room to do it in."

"No problem, I have a friend at the hotel across the street, a bell hop I do favors for, I'm sure he could swipe a key to an empty room." As she walked from the bar he got a better look at her. Damn she was hot, coal black hair, nice tits and an ass that was just awesome. He reconsidered why he wanted her. No, no he could get that some other time he knew what he wanted, no needed right now. "I'll call my friend, go by the elevator and wait.".

He did as requested and waited until his 'fallen angel' returned with the electronic key in hand. "615" She said as she pushed the button for the 6th floor. She unlocked the door and went inside with him close on her heels. She turned and held her hand out; he placed the money in her hand.

"Open your bag and lay all your things on the bed. "

He did as he was told laying them all out neatly as was his custom. A black maid's outfit trimmed in white, black hose, black garters with white trim, White panties with black trim and a bow at the top of the open crotch. He set the shiny shoes on the bed beside the outfit. A small make up case was put on the bed as well. Some ankle and elbow restraints and a few rachet straps with clips on the end to attach to the restraints joined the other items. A nice wide razor strop, a short doggy whip and a thin wooden ruler ended up there as well. She looked him over.

"Strip! If you tell me exactly what you want it will be a better session."

As he undressed, he spoke, he seemed ashamed. "I want you to shave me, make me look like a girl. Make up, especially red lipstick, dress me and spank me. I want you to humiliate me for wanting this as you are doing it. Make it hurt but make me feel really humiliated when you do!"

She nodded her head; she loved these little sissies. It gave her a chance to make easy money, and a chance to get even so to speak. Get even for the way men treated her. He stopped undressing at his underwear.

"Get that off you fucking Sissy! You don't deserve to wear men's underwear!"

She picked up the doggy whip and cracked his across his thighs. He let out a howl and pulled the underwear off and stood before her stark naked. She put the whip handle under his cock. "No wonder you want to wear women's clothes; this little thing is no bigger than a clit." She reached out and clamped onto his nipple. "Come with me you fucking sissy! I'll show you what I do to Sissy's! You are such a little sniffling bitch!"

She dragged him into the bathroom and pointed to the shower. Turning the water on she pushed him inside and his cock shrank even more as the cold-water blast against his warm skin. He knew better than to adjust it so he shivered in silence. He watched as this woman disrobed in front of him and she smiled.

"If you were half a man, you could be fucking this tight snatch, sucking on my nipples, but you're not, you are a fucking little sissy!" She rubbed her nipples as she walked toward him; they were erect in an instant. As she reached in adjust the water to her pleasure, she pushed the nipples toward his face. "Look you little cock sucking Sissy, my nipples are bigger than that pathetic little wee wee you got! Keep your hands off me you fucking little faggot! Turn around and face the wall!"

He did as he was told and she lathered up his back and proceeded to shave his back, bottom, legs, arm pits and deep down in his crack. "We want that little sissy pussy all clean and ready for action don't we sissy" He only sobbed as he watched the hair slide down the drain. She ran her hands all over the area she just shaved and was satisfied. "Turn around you little Sissy. She started to lather up his mustache and put his hand up to stop her. Her hand smacked his face with more force than he could have imagined. "Don't you dare raise your hand you fucking little sissy or I will Whip you like you have never been whipped!"

He was shocked, he stood very still. He knew there had to be tears in his eyes from the sting. Quick work was made of his face, chest, and crotch area then finished up with the legs. She rinsed him off and he stood back as she lathered herself up. She reached at her lower lips, spread her legs a tad then he saw the golden nectar come gushing from her pussy. She saw the excited look in his eyes, so she moved her hand about until it squirted on his legs. "What's the matter little Sissy never see a woman stand and pee before." He shook his head, and she only smiled. She rinsed off and rinsed off his legs again before stepping out of the shower. After drying them both off she made him lean back against the sink and she took the medical tape and taped his little member back toward his crack. "You'll be pissing setting down the rest of the evening you little sissy!"

Reaching into the bag she came out with a thick butt plug. "Oh, some little sissy wants something up his little pussy tonight." She bent him over then used the hot damn lube he had to prepare his waiting pussy. A groan came from deep within. An even deeper groan came as she shoved the plug deep inside him. She pulled a small elastic hair band from her purse and looped it over the head of Phillip's trapped cock. She pulled it through the loop on the butt plug and looped it so it was fastened tight.

Pulling a chair in front of the mirror she made him set and watch as she made him up like the fucking little slut he was. "Oh, I hope you make a nice girl because you are a pathetic little man." She put base coat on his face then finished him off with mascara and blush. Eye lashes and eye liner followed then the bright red fuck me lipstick. She set the wig in place and looked him over. "Damn I think I could pimp you out Sugar!" She slid the stocking up his legs, made him stand and put the garter around him, attaching the stockings to it. She had him slip into the short maid's outfit and finished it off with her shiny new shoes.

"Oh, you are such a hot little Sissy!" She went to the large Ottoman and bade her Sissy to help turn it on its side. She laid the web straps out on an 'X' pattern and set the Ottoman on top of them. "Now my little Sissy, get up on your elbows and knees! It is time for you to get that Sissy ass spanked! Get going you fucking faggot! Get in position!" Her doggy whip caught Phillip in the crack of her panties, and he lurched onto the Ottoman. "Spread that fat fucking ass of yours, you worthless Cunt!"

Phillip spread as wide as he could, and she put the ankle cuffs on each ankle. Then moved up to his side and put the elbow cuffs on as well. Reaching down she clipped the ratchet straps to each cuff in turn. The right elbow cuff tightened at the same time as the left ankle, as did the left elbow and the right ankle. He was not only spread wide but pulled tightly against the Ottoman. His ass high and spread, his head low and hanging off the Ottoman. She grabbed the thin wooden ruler and started spanking as close to his exposed butthole as possible, occasionally hitting the butt plug. Phillip howled to high heaven. The smacking stung hard, and Phillip was crying out begging her not to spank him there.

"Please don't spank me there! Please!"

"Shut up you fucking whore! I am going to spank that nasty cunt of yours till it is swollen and sore!" She proceeded to spank his swollen red ass hole, every once in a while, she would swing underneath catching the tip of his little cock and making him squeal. "Are you going to give me a good tip for doing this to you my little Sissy assed Cunt? You give me some more money and I will stop spanking that swollen little cunt of yours and spank your fat fucking ass! How much money you got my little Cunt?" Phillip managed to sob out "$50."

"$50! $50! Why you worthless Cunt you got more than that!" She dropped the stick and started rummaging through his pants. "Only 50 fucking bucks? No credit cards? You worthless Cunt! I ought to leave your ass like this! She dug through the gym bag finding nothing; she picked up the whip and started striping his ass across the panties. "You want humiliation you little cock sucker! You want humiliation! You are going to get it!"

With that she went to his face and pulled it to her ass as she bent over, sliding the panties to the side she rubbed his face against her ass hole. "You can kiss this goodbye you fucking cheap ass Sissy! " With that, she walked to the bag and pulled out a penis gag, slipping it in Phillip's mouth and pulling the straps over his head. "I have had enough of that Sissy fucking mouth! You, cunt faced, bitch suck on that for a while!" Out the door she went along with Phillip's trousers. The door slammed and Phillip was left alone.

What the hell had he gotten himself into?

NEXT

Hours passed and Phillip was no closer to getting loose than he was when she left. His arms were numb as was his legs. He had tried to throw his body to one side to turn over the Ottoman, but it just wasn't happening. He dozed. He was awakened by a slight noise; it sounded like a card slipping into the reader. The door opened. He didn't know to be elated, humiliated or scared, but he was soon to find out.

"What the fuck is this?" A man stepped in front of Phillip a very large man from his perspective. "What the fuck are you doing my room?" Phillip could only mumble through the gag. The man reached down and removed the gag.

"Oh, thank you! Thank you I have been here for hours! Please unhook these straps sir."

The man circled Phillip, his finger tracing the red whelps on Phillip's ass. His finger thumped on the exposed part of the butt plug. He made his way back to the front. "Why are you dressed like this and why were you left tied up?" Phillip was so embarrassed, and the man made him explain his fetish.

Phillip told how the prostitute wanted more money and having none she left him, like this! The man started unbuckling his pants. "This just doesn't seem to be your day, Sugar!"

"NO!" Phillip begged, You don't understand I am not gay, I am not Bi, I just like to play dress up and be spanked some but that is all I am" The man shoved the penis gag back in his mouth and slid the straps behind his head. Phillip's eyes were wide with fear as the man turned and stripped his clothes off. The guy was big, not fat but muscular and hairy. Phillip thought of a carpet, hardly anywhere on this man's back could you see bare skin.

When he turned to face him, the breath caught in Phillip's throat. The man's cock was thick as Phillip's wrist and nearly as long as from Phillip's elbow to his wrist and it wasn't even hard. He stood silent in front of Phillip.

"I am going to shower then I will decide to take those restraints off or not." As he walked away, Phillip could see that huge cock swing back and forth. Phillip started struggling harder of that was at all possible, but to no avail. He heard the shower shut off and steam came from the door as the man came in his view. But the view was different now, the man's cock swung straight out in front of him. If it seemed huge before it was Gigantic now. As Phillip lay there unable to move, the man stood in front of him.

"I have made a decision; I hope you don't have a plane to catch!" He went behind Phillip to the bed and picked up the wide razor strop. "I don't see why people get into this, but I am about to find out. The strop swung so hard it brought a sharp cry from Phillip. There was a 3-inch bright red stripe across both his cheeks. It hit a second time, and the redness shone brightly through his panties. The big man gave him 20 then ran his hands up Phillips legs, the panties were soaked and dripping, poor Phillip had lost control from the long time he had been tied and the force that the razor strop hit. He jerked the butt plug from its home and Phillip yelped.

A thick finger went through the open hole in his panties. It circled his little butthole and pushed inside. Grunts were escaping Phillip's gag. The fingering stopped. Phillip looked up to see the head of this hard cock bounce across his cheeks. The straps from the gag were being removed and the gag pulled out. The head bobbled against Phillip's lips. "You can do this the easy way, get it nice and wet or I can dry fuck that little hole of yours!" Phillip shook his head again.

"But, but I am not gay."

The man grabbed the ruler on the floor and started spanking Phillip's balls until he heard what he wanted. Phillip was bawling and begging to suck the man off. He grabbed Phillip's jaws and pushed the huge head against his mouth. Phillip's mouth stretched until he got the girth inside his mouth. He could taste the man's precum. Poor Phillip could not even take enough to feel the balls slapping against his throat. He pulled out leaving a trail of spit from the cock to Phillip's mouth. The man's hands rubbed his cheeks and began hand spanking his panties. He started pushing the thick cock through the opening in the panties. "I don't think that little plug will prepare you for this Sugar!"

Phillip could feel the head against his sore swollen hole. As the man pushed harder, he could hear his panties rip. A large hand grasped his mouth keeping him still, just in time as the big head stretched his poor little asshole. Phillip's screams were muffled as inch after inch worked inside his ass. Tears were running down his face as he felt the cock saw in and out his virginal ass. The thrusts were coming harder and faster, and his own breath was ragged. His hips were gripped harder, and the fucking became wild as the man reached his climax, he rammed Phillip's ass harder and harder. Phillip screamed and somewhere along the way passed out.

He awoke lying in the bed, his dress off and he was only in his garters and hose. He was weak and sore; his ass hole was burning. He was weak; he tried to slide to the edge of the bed. A heavy arm came over pinning him to the bed, even asleep he was stronger than Phillip. He pulled Phillip closer; he could feel the man's cock brushing between his cheeks. Phillip tried again to slip away but in moving about seemed to be rubbing against the big man's cock. He tried to be still hoping, it would go away, but it wasn't to happen. A hand grasped his mouth as the other his hips. He felt it again, the thick hard cock sliding into his sore swollen ass hole. Thankfully he didn't shove the whole thing in, only a few inches. Slowly he rocked Phillip as he fucked him. A much softer fucking and he shot squirt after squirt filling his Sissy pussy up. He rolled over and shortly the snoring began.

Slowly, and quietly as possible, Phillip slid to the edge of the bed. Barely able to walk, he quickly found the maids outfit and managed to slip it on. Straightening his wig, he stopped long enough to place a call to the taxi company and whispered his address. He made his way to the elevator. My God his asshole was sore, he could barely walk straight. He left the building when the taxi pulled up outside. The taxi driver gave him a second look but hell this was Reno. It was only a block away but there was no way Phillip was going to walk there.

He gave the driver the $50 he had hidden in his shoe and made his way into the hotel. Keeping his eyes down; he asked the clerk for the key to his room. Closing the door, he let out a long sigh, glad this ordeal was over. Gingerly his fingers removed the tape holding his cock between his legs. A long hot shower cleaning off all the makeup, his fingers went to his poor asshole it was gaping open. OMG was that SOB hung! He looked at the clock; it was only a few hours until the meeting. He called the desk to make sure he got a wakeup call in time to get up and ready before lying down on the bed.

Phillip realized he was walking funny as he made his way to the business meeting. His ass hurt like hell. He needed to be focused on this meeting it was very important to his future, but it was on last night's happenings that his mind was dwelling. After meeting the board members, he took his seat gingerly. He had been having serious gas attacks all night; he hoped he could control it through the meeting. The president strolled in and took his seat. OMG it couldn't be... The man from last night!!!

THE END

SIZZLEBUNS