Charlie and Joe

By charles tyrrell

Published on Nov 26, 2010

Transgender

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Comments welcomed. I reply to all emails. merlinrules@yahoo.com


Little Charlie was a born pervert. He would try to look up little girl's dresses as they climbed a tree and followed little boys into their bathrooms to watch them piss. His hormones were kicking in early and hard.

One day while he was walking in the woods with an older boy near his little town shooting BB guns, he had a sudden urge to let his stiff little prick stick out of his overalls. He didn't yet know why but he wanted the other boy to see his bare prick.

The older boy looked at the prick being presented to him and asked Charlie if he wanted to jack off. Charlie didn't know what that meant but said sure, because it sounded naughty.

The older boy took him to a nearby barn and told him to undress, which Charlie did, a delightful naughty feeling overwhelming him.

Charlie watched as the older boy's hard prick sprang out as he dropped his shorts. The boy started to talk dirty as he squeezed pre cum from his rigid cock and started to play with his wet erection. "Look at my big cock. Fuck but it feels good to jack the hard fucker in front of you. Come on Charlie, jack your cock like I am," he said.

"Fuck yes, this feels so good, jacking my horny fuck meat. Your cock is so big, can I jack it? I am so fucking horny," Charlie said.

The older boy stood with legs spread and Charlie knelt down in front of him and took his wet cock in both hands and started jacking just like he had seen the older boy do.

"Oh yeah Charlie that feels so good. Pretty soon I'm going to cum in your hands. The cum will shoot out of the prick head and that is the best fucking feeling in the world. Fuck, I'm about ready. Oh fuck yes, keep going, here I cum!"

Charlie had never ever felt so naughty as when streams of warm cum shot all over his hands and bare chest. Charlie took the slippery cum and rubbed it over his stiff little prick and jacked until he had his first orgasm. Years later he looked back on the experience and wished he had known to suck him off.

The older boy moved away and Charlie lost his one and only jack off buddy. However, he was jerking off two or three times a day. Everything turned him on, even his Marvel Comic books. He was still in grade school with no outlet for his supercharged cock, except his hand. He started finger fucking his ass hole as he jacked his growing cock, a perv in a boy's body.


The years pass and, after several marriages, Charlie finds himself single. His first wife liked the way he fucked her with his oversexed 8" cock but she wasn't kinky and Charlie lost interest. He wanted her to fuck other guys but she thought that was sick.

The second wife was a perfect fucking slut. She got drunk and brought guys home and fucked them and Charlie loved the sloppy seconds. He was also wildly into porn and discovered a site where guys showed off their horny stiff cocks in panties and stockings. He had never forgotten the older boy's squirting cock and realized that cock turned him on more than cunt. And cock in panties was even more naughty and a super turn on for him.

He started wearing his wife's cum filled panties and her stockings while she was out drinking and fucking. One night he put on lipstick and was standing in front of a mirror jacking off in her panties when his drunken cunt and her latest boyfriend stumbled in and found him in her cum filled panties.

Well, that was the end of his second marriage. Now he spent his off time dressed like a fucking slut and jacking his big prick off into his drinks looking at male porn sites. One night, while he was drunk from drinking his cum laced drinks he took his picture and entered it on a male porn site.

He shaved his slender long legs and pubic area and even applied make up and a nice wig. He loved the black mesh stockings, lacey garter belt, thin silk panties (when he wore them) and a black party dress. Shit, he looked sexier than a lot of women.

He tried sucking his cock but couldn't. But he was fond of jacking off in his drink. He needed to jack off at least three times a day so he could get drunk on his cum drink. He even got a small cock shaped dildo to fuck his virgin ass hole and pretend it was the real thing. While he pretended a real cock was fucking his moist ass hole he started calling himself "Charlene."


One evening he noticed an email addressed to "Charlene." It was from a man named Joe. Joe wrote that he had seen the Charlene picture on the male site and thought it was beautiful and extremely sexy. He said he would love to chat.

Charlie wrote back that he would love a male friend and asked for more details from Joe. Charlie was a little high on his cum drinks and added a picture of him in just stockings, garter belt and high heels, his big cock wet with pre cum and standing straight out. Later Charlie wondered if he had scared Joe off by sending the photo.

The response from Joe made his heart race. Joe said he loved the Charlene picture so much that he made a copy and then jacked off on it. Joe said he had never been with a man but had been thinking about it for a long time. He just had to find the right person. At the bottom was a photo of Joe's spent cock laying on the cum covered photo. It was signed, "Love Joe."

Charlie was so excited that he jacked a big load into a glass and then added brandy and drank it in a gulp, savoring the taste.

"Dear Joe, his email read, thank you for the photo of your beautiful cock cumming on my picture. You are so sweet and very sexy to me. I wish you could see how hard my cock is for you right now. You excite me so very much.

"Other than having an older boy showing me how to jerk off when I was little I haven't made love to a man either although I have wanted to for years but have been afraid of being hurt. Could you love me, Joe? My love... Charlene."

To the email Charlie uploaded a photo taken from the rear. A close up of Charlie bent over holding his ass hole open dressed in just stockings and garter belt, big cock and full balls hanging down.

"Darling Charlene, the response read, yes, oh yes, I could love you. You are all I think of my wonderful Charlene. I hope you aren't offended but I would really love to meet you in person. Oh honey, I am yours to love. Yours, Joe."

The emails continued back and forth, telling of love and lust. Finally Charlie suggested that Joe fly in and meet him for drinks and to see if the chemistry was right.

Joe made reservations at a five star hotel that had an upscale bar downstairs for lovers. Candle light, dancing, soft music and private booths. A date and time for the meeting was set. Joe made it clear that he wanted to meet his Charlene, dressed as in the photo.


On the big day Charlie made the change to Charlene. "She" had a long bath. She shaved her long legs, pubic area, the rest of her body and painted her toe nails and fingernails.

After she shaved her full ball sack her big cock was so turgid that she jacked off in her glass (es) of brandy. She spent time cleaning her virgin ass hole and only teased the brown pucker hole several times.

Finally she stood in front of the floor length mirror and studied the results. Fuck but she was beautiful. Tall, slender, perfect black wig and makeup contrasting to her soft white skin. Short black party dress showing her white skin above the black stockings. A hint of black garter belt to set it off. She would wear her black high heels when she left her place for the hotel.

She was a little drunk as she stroked streams of cum into her new drink. Fuck the panties, make it easier for Joe to find her large prick.


She took a taxi to the hotel and saw men watch her as she walked in. She thought it was a little funny that her cock was probably bigger than theirs.

She took the elevator down to the lounge and felt her cock swinging free and growing against the dress material. As the door opened she was glad it was so dark as her cock was getting hard.

She stood for a moment letting her eyes adjust to the candle light when she heard her name, Charlene. A very nice looking middle aged man stepped away from the bar and smiled at her.

"Joe?" she asked.

"Yes my darling. You look so beautiful. Let me show you to our private booth and then I'll get us something to drink."

She admired Joe's body as he made the trip to the bar. When he returned with the drinks she noticed his shirt was unbuttoned at the top showing a hairy masculine chest.

She in turn had crossed her legs showing her white skin and garter belt above her stockings.

"Joe, do I look ok to you? I am so nervous that I had several drinks before coming."

"Oh yes my dear. Shit, I got to admit that I've had several myself. Sorry, didn't mean to cuss."

"Dance with me baby. I love naughty words. Makes my fucking cock wet. Ok?"

Joe took her hand and lead her to the small dark dance floor. He looked into her eyes and slowly rubbed his hand down her back to her ass and pulled her close, their engorged cocks rubbing together.

Then he kissed her, tongues exploring. Charlene was in love with this hot man and her cock needed attention. Back in their booth they continued kissing and she felt his hand on her bare thigh, just above the stocking.

He finally found her 8"s of cum filled wet fuck meat. By now she was pretty drunk and giggled and said she must have forgotten to wear panties. She was so hot and hard.

"Joe my love, I am so fucking turned on. I feel like being a very naughty girl with you. I have tried to behave tonight since we just met. I love to jack off in my drink. Are you still ok with me?"

"Charlene, you are so fucking perfect. I have never even thought of jerking off in my drink but it sounds cool. I love the feel of your big wet prick. Shit baby, lets go to my room. Ok?"

In the elevator Joe pulled up her skirt and felt her bare ass with one hand while he stroked her throbbing meat with the other. She was trying to get his dripping cock out of his pants when the elevator stopped at his floor.

In his room she took off her dress and was beautiful in just her stockings, garter belt and high heels, her pulsating cock streaming pre cum and of course her make up.

"Hey baby, get me another drink while I take a piss. I'm about a drunk cock sucking slut."

Charlene was taking a long piss when she felt kisses on her neck and a huge cock between her ass cheeks. When she took the drink from Joe his hand felt down her belly to her shaved prick and held it while she pissed.

She downed her drink and turned around to find Joe on his knees. She moaned as he grabbed her ass checks and pulled her cock deep in his mouth sucked for a little while.

He stood up and she loved the looks of his body. Hairy while she was shaved and stocky where she was slender. And what a cock he had. Big and beautiful.

He held her hand as he helped her to the bed. She was really ripped.

"Fuck my ass you beautiful cock sucker, she said. But first let me suck your big fuck stick."

She couldn't believe how good his dripping prick felt and tasted as she sucked him.

Then she laid back and raised her slender stocking clad legs for her lover. He got between her legs and she felt his fuck meat probing her little brown ass hole.

Eyes locked in passion she felt his prick enter her ass, deeper and deeper. He drew his cock out and back in slowly so as not to hurt her. When he felt her ass open he picked up his speed.

She had never been so turned on and cried out that she was going to cum. He picked up his speed as her prick started shooting cum all over her chest and belly. The timing was perfect as he then started shooting streams of his cum deep in her bowels.

He had no sooner pulled his spent dripping prick from her ass than she pulled him forward and took him into her mouth. He started growing again and so did she. She had him get a glass and scoop her cum from her chest and belly. Then he added his drink and drank it down.

He said he loved the taste and pretty soon they were jacking each other off in to more drinks.

They must have passed out because suddenly it was morning and they were in each other's arms, cocks turgid again.

Charlene woke up first and smiled when she saw how hard Joe's cock was, even asleep. She leaned over and his cock slid right into her mouth. She loved the taste of dried cum and the fresh pre cum.

She went to the kitchen and filled a glass with orange juice and returned to bed. Joe was awake and watched his lover's big cock bounce as she smiled at him.

She got on her knees and said, "Good morning you horny ass fucker. Let Charlene show you how I fix breakfast."

She placed the glass of OJ under her swollen prick and started to stroke herself. Joe thought she was so beautiful, her painted finger nails against her smooth white prick as she jacked herself faster and faster.

Her painted lips parted as she closed her eyes and had her biggest orgasm, shooting huge streams of cum into the glass.

When she finished said handed Joe the glass and said, "Ok baby, Charlene has fixed your breakfast. When you finish how about you fuck my moist little ass hole or maybe you'd like me to suck you off like the good little cock sucker that I am."

"Oh Charlene, I love your breakfast. Let me pump my fucker into your drink now. Then baby, if you feel really naughty later you can wear your fuck me outfit and we'll see what we can get into. I want to show you off."

What a perfect couple.

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