Story for Mastsir

CHARLIE AND SANDRA

Charlie was a Cross Dresser. He loved all things feminine and spent hours dreaming about his wardrobe. His job was a bit of a high stressor but he had time during his busy day to surf the web, look up nice fem clothes for him to wear and check on his email to several other Cross Dresser's.

Sandra lived in a neighboring State and Charlie and Sandra wrote many emails to each other. Made up stories about sneaking into each other's bedrooms at night and butt fucking the other one. Sometimes knowing who it was and sometimes a stranger.

It was all good fun and Charlie would get excited and live in his made up world for a few minutes. He couldn't do that at home because his wife of 30 years was a true dominant. She pushed him around, gave him orders and generally made his already stressed life a living hell.

One Monday he got an email from his friend Sandra that she said she was going to a near by city for a few days on business and wanted to see Charlie if he could come by.

Charlie got the dates and figured out how to get away one afternoon. The drive was only an hour so he could go and get back easily.

The day came around and Sandra sent Charlie the hotel address and room number. Charlie left work for lunch and told his secretary he would be out for a couple of hours.

Upon arrival Charlie knocked on the room door and a beautiful girl opened it. She was bigger than Charlie, taller and her chest was enormous.

"Hi." Sandra said as she wiggled her tits and welcomed Charlie into the room.

"Wow, you are something else. Your beautiful and sexy."

"Isn't that why we're here."

Charlie reached for her waist and pulled her tight, they lip locked and tongue lashed for several minutes. Charlie had never kissed another man but Sandra was turning him on like a hot flame.

They had some wine and chatted about cross-dressing. Sandra told him things about clothes and undergarments that he didn't know. Her tits were water balloons. She said real tits are mostly water and these feel and act just like real ones, and if you tie them right the knot works like a nipple.

She demonstrated and I felt them again. Wow, like the real thing.

"Show me what you got." Sandra said.

"What do you mean?" Charlie said.

"I want to see your cock and ass."

"Oh, Okay."

Charlie took his clothes off and Sandra groped him several times, fell to her knees and took his manhood in her mouth. It was sweet and she made him stand tall.

Spinning Charlie around she planted her tongue between Charlie's cheeks and found the hot button at the bottom of the cleavage.

"Oh my." Charlie said.

"I want some of this ass." Sandra whispered.

She pushed him over on the bed and pulled her skirt and panty hose off exposing the biggest dick Charlie had ever seen.

Charlie rolled on his back to watch her get undressed and was amazed at her body. When stripped down she looked like a pretty face on a hunk of male body. He was trim and toned, big and hard.

She climbed up on the bed and rolled Charlie over, grabbed the KY bottle and lubed Charlie's asshole. He broke the seal on a new condom and lathered it up as well.

Mounting Charlie was quick but entrance wasn't so easy. Charlie after all was a virgin.

"You been fucked before?" Sandra asked.

"No."

"Well we need to take a different approach then."

Sandra pulled him back to the edge of the bed and dropped his legs to the floor. Reached under him and lifted his ass in the air.

"Keep it up here."

Sandra moved in with fingers and pressed first one and then two into Charlie's butt hole.

"Wow, baby you're tight as hell."

After several minutes of that Sandra mounted him again and managed to get the head inside, just barely. Holding his long hard dick with his right hand he kept it up against Charlie and gave a big shove.

"Owe, that fucking hurts."

"It will pass, always hurts the first time."

Sandra went to the bottom, gripped Charlie's ass and just held that for a minute. She could feel him relax a bit so she started going in and out. Not pulling out totally, just sliding back and forth.

"Oh baby, you feel good. Your so damn tight."

"It feels better now."

"I never had a virgin before, your great. Now give me your hands."

"Huh?"

"Put your hands behind your back, face in the bedspread."

"Okay."

Charlie put his hands behind his back and felt Sandra grab hold and pull. Accelerating his pace of fucking he pulled hard on Charlie, stretching his shoulders almost painfully.

Sandra reached over to a side table and got something that Charlie couldn't see. Suddenly he felt something being tied around his wrists. Then Sandra leaned back, pressed his groin in hard and pulled on Charlie's bound hands.

"Ah, that's better, not I can pound you properly bitch."

"What are you doing?" Charlie stammered as Sandra increased her speed and force of assault on Charlie's ass.

Sandra had a lot of stamina and she kept it up for several minutes. Then she pulled all the way out and re-entered Charlie again. The sensation of passing thru the sphincter was exhilarating for both of them.

Holding the rope with one hand and Charlie's ass with the other Sandra continued to pull all the way out and slam back in.

Charlie was beginning to wonder what had happened. "What are you doing?"

"Fucking you bitch, fucking you good."

"Maybe you should ease up a bit." Charlie cried out.

"Not a chance, this is good shit here."

"You're starting to hurt me."

Sandra pulled out and checked her dick. "No blood so it can't be bad."

"It still hurts when you go all the way in."

"You will get used to it." And Sandra continued to slam into Charlie's ass.

"Please stop."

Sandra pulled out suddenly and pushed Charlie to his knees facing the side of the bed. Quickly he moved around and sat on the bed in front of Charlie with his hard dick in his face. Stripping off the condom he shoved it in Charlie's mouth.

"See if that shuts you up."

Charlie had sucked a dick once but the force and size shocked him. Sandra grabbed his head and pulled him into her groin.

He couldn't talk but he gagged and coughed. Sandra gave him time to clear his throat and then began the assault all over again.

"I'm going to fuck your throat bitch. I like your ass better but this will work."

Charlie's hands were still tied behind his back and he had difficulty maintaining any balance at all. Sandra was holding his head; he was on his knees and had no leverage to escape the thrusts into his face.

Soon Sandra had defeated his gag reflex and was burying his pubic hair in Charlie's nose.

Charlie had given up, his mouth went slack and his body relinquished its tension.

Sandra just kept up the pounding. Then suddenly stopped, pulled Charlie's head back and grabbed is monster cock with his hand and started stroking it.

"I am going to cum bitch, and you are going to eat all of it."

Just as suddenly as he pulled out he started to spew gobs of white semen and sperm. Pushing his cock to Charlie's lips he said, "Open and suck."

Charlie did what he wanted and his mouth filled with the salty blend. It was more of a shock than anything else.

Still stroking and pumping Sandra kept the spuge coming. Finally he was empty and ran his finger around Charlie's mouth and cleaned all the cum up.

"Lick my finger."

"Now get up on the bed you piece of shit. I hate queers and your going to get fucked all night long. I have some friends that will enjoy keeping you filled with cum."

Charlie managed without his hands to stand and flop onto the bed. He felt Sandra untie one of his hands and pull it up to the headboard, saw him loop it around the bed post and bring it back to Charlie's other hand and retie it.

Then Sandra got another piece of rope and tied his feet to the bottom of the bed spread eagle.

"Now you look almost ready for a train fuck."

"I don't want to do this." Charlie sniffled. He was almost in tears from the shock and pain of the restraints.

"Well, ain't that too fucking bad bitch. I hate this make up, I am going to take a shower and wash my face."

Charlie lay quiet and tried to clear his throat and mouth. The sticky cum was hard to move and his mouth was dry. He could just barely lift his head and look around.

"Can I have some water please?" He called out.

"Yea, when I get done."

Shortly, Sandra came back from the bathroom and had a glass of water. Untying one hand Charlie could roll up on his side and drink as Sandra held the glass.

"You pathetic cunt." Sandra said as he stroked his flaccid cock.

The phone on the nightstand rang and Sandra went to answer it.

"Yea. About damn time; we are ready to go up here, is everybody there?"

He hung up and looked at his captive.

"The boys are here and the fun can begin. Do I have to gag you or will you keep quiet."

Charlie said, "Do I get a choice?"

"Yea, right up to the point where you start screaming."

There was a knock on the door and Sandra went to open it.

"Okay boys, put your donation on the TV and get your dicks out."

There was some mumbling and Charlie tried to look around but he was restrained so tight he could barely see what was beside him.

The first guy on the bed with Charlie swabbed Charlie's asshole with something slick and immediately sunk to his full length.

"OH SHIT that hurts." Charlie screamed.

"Shut up Charlie or you get gagged."

"Uh, sorry." He croaked out.

The first guy was pounding away and Charlie was loosening up a bit. The pain had subsided but by no means was this fun. When he pulled out and moved to Charlie's face he shot his load all over the side of Charlie's head, in his ear and hair.

Sandra said, "Oh, I love to watch cream pies, what a beautiful pile of cum."

She scooped some of it up with her finger and put it on Charlie's lips. "Open bitch."

Charlie opened and she put her finger in his mouth for him to suck.

"You want some dick to suck cunt? Hey guys the bitch wants to suck some dick."

One of the guys in line for Charlie's ass came around to Sandra and she untied his hands and retied them behind his back. He slid up under Charlie's face and shoved his erection in Charlie's mouth.

Charlie did his best but the double action was not giving him much pleasure. It was hard to do anything with his hands tied.

One by one the four guys climbed on board and fucked Charlie's ass and then left their loads in his mouth.

After number two he was wide open and the pain was gone. He really wished he could get untied; this might be fun if he could enjoy it.

When number four had lost his load and the guys were getting ready to leave Charlie relaxed and laid his head down on the spread. His shoulders ached, his asshole ached and he just wanted to be free.

Sandra came to the bedside and said. "All this fucking has me hard again."

She untied Charlie's feet and let him come up on his knees but his hands were still tied.

Dragging him to the side of the bed Sandra put his legs on the floor and started to slide into his gapping asshole.

"Wow, those guys really opened you up I think I can see your tonsils in here."

"Very funny. Let my hands go, please."

"Okay, would you like a shower?"

"Yea that would be nice." Charlie said.

She untied Charlie's hands and helped him to his feet. They walked together to the shower and Charlie got in the tub. Sandra turned the water on and adjusted the temperature.

"I will be out here if you need anything." She said.

When Charlie came out of the shower Sandra was laying in the middle of the bed stroking her big cock and watching a porn movie on TV.

"I want to breed you bitch. Do I have to tie you up again?"

"No, that's really more pain than the sex."

"Sit on the edge of the bed." She said.

Charlie sat on the edge and Sandra came and stood before him.

"Make it wet cunt."

Charlie leaned over and took his cock in his mouth and began to suck it hard. Maybe I can get him to cum here and save my ass for another day. Charlie thought.

Suddenly Sandra pulled back, "Your trying to suck me off bitch."

"No, you asked for me to suck you."

"Get your legs up."

Charlie lifted his legs and Sandra grabbed his ankles and pushed them way over Charlie's head.

Charlie's ass was exposed and Sandra wasted no time making entrance. The shower and washing had enabled it to shrink somewhat but it was still loose and offered no resistance to Sandra's incursion.

"That's just right now bitch. It feels good."

Charlie couldn't talk from the weight of his legs and Sandra leaning on his bent double frame. He could hardly breathe.

The pounding continued and Charlie closed his eyes and tried to think of pleasant things as Sandra had her fill.

Without fanfare Charlie felt Sandra release his seed and suddenly realized that he didn't put a condom on and was in fact breeding him; the final insult.

Charlie was exhausted when he crawled up into the bed and tried to rest his aching body. The only thing he heard was the sound of the door closing as Sandra made her exit.