Charlie Becomes Charlene

By charles tyrrell

Published on Nov 26, 2010

Transgender

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Comments welcomed. I answer all emails. merlinrules@yahoo.com


After a long and difficult divorce I moved to another state and started a new job in a large office building.

I was rather depressed and confused but still very sexually charged. Most evenings I would have a few drinks, watch porn and fuck my hand. If I had enough to drink I would lick up my cum and finger fuck my virgin ass hole.

After several weeks at work a nice looking well dressed somewhat older man would stop by my desk and chat. We hit it off and I looked forward to his visits, short as they were.

As summer approached we started meeting outside to eat our lunches. We had a lot in common. He was also divorced and not dating. We agreed that men were a lot easier to talk to and understand.

One hot Friday afternoon while we were eating lunch John asked if I would like to spend the weekend with him at his apartment in a nearby town. I was quite taken by his friendship and said I would love to. He said to dress light because his air conditioner was acting up and I gave him my address.

Right on time he pulled up in his car and I put my bag in the back seat and got in wearing baggy shorts and a pull over shirt. He smiled and said I might still be over dressed.

He was stripped down to just brief shorts with a hint of a cock bulge. I wondered if my new friend was trying to seduce me. Fuck it, it had been awhile since I had a piece of ass and I was fucking horny.

He reached behind him and opened a cooler and got us beers and off we went. We drank and talked and were both a little ripped by the time we got to his apartment.

I followed him into his very small apartment and put my bag in front of me to hide my own swelling cock bulge. He was right, it was hot in there.

We sat on the pull out couch that made into a small bed and he made us tall cool drinks. John sure knew how to make a strong drink. I wondered if he knew how horny I was getting or if that was his plan. Fuck it; I was ready to get drunk. What could happen?

John drained his drink and stood up. He said he was going to take a piss and shower while he could still stand up.

He dropped his shorts in front of me and his semi rigid cock sprang out. The bathroom was right next to the couch and had no door. He stood with his hands on his hips and made a show of pissing. He said he hoped I didn't mind but the fucking place was so small. I told him I thought it was just right.

He stepped into the shower and I could see him soaping and stroking his fat prick through the clear shower curtain. I was getting seriously turned on to this perverted mother fucker.

I should explain that he is older, on the stocky side and has quite a bit of body hair. I am quite a bit younger, tall and slender; fair skinned and no body hair because I shave.

He stepped out of the shower, dried and went to get us more drinks. He sat on the toilet seat and watched as I showered. He made no effort to hide his hard cock from me.

I got out, dried and put a foot up on the sink and started to apply lotion to my slender long leg, my 8" of shaved fuck meat wet with pre cum. hanging down.

He mentioned that he had never seen a man with shaved legs, pubic area and cock. I was afraid he thought I was weird.

I told him that I used to watch my mother shave her legs and I thought it was sexy. I made my little prick hard. Later I started to jack off in her soiled panties and then go play feeling my prick soak in her cum filled panties.

As an adult I started shaving my legs and wearing stockings and panties under my street clothes. This lead to my downfall and divorce. My wife caught me wearing one of her dresses and jacking off. She left me.

John drained his drink and told me that he thought it was fucking sexy to dress like a woman. By now he was slurring a little and his cock was rock hard. He asked if I would model a dress for him.

I told John that I would love to dress for him but that I was fucking drunk and horny and hadn't been fucked for awhile. He said to finish my drink and let him see for himself.

He waited on the couch and didn't look while I got my bag. I pulled on shear black stockings over my smooth legs and then a black garter belt. Then a short black party dress and stepped into black high heels. Fuck the panties; I wanted the mother fucker to see my throbbing cum filled cock pushing the material out.

My fucker was so hard I could barely lean against the sink to apply my eye shadow and lip stick. I was so fucking loaded that I had trouble getting my black wig on straight.

I had him close his eyes as I stepped out of the bathroom and stood in front of him hands on hips and my rigid fuck meat pushing on the dress material. I licked my painted lips and smiled at him and asked if he liked what he saw. I told him that I felt so feminine and sexy that he could call me Charlene.

His mouth fell open and all he could say was, "Oh Charlene, you are so beautiful."

"I'm glad you think your Charlene is beautiful" I said as I knelt between his open legs. I kissed the pre cum off of his cock head and then licked up the pre cum puddle under his hairy ball sack and then licked up the under side of his cock shaft.

Just before I sucked his big cock between my painted lips I said, "John honey, your Charlene feels like such a cock sucking slut. Come on baby, fuck my cock sucking mouth and feed me your cum."

He grabbed my head and started grunting and humping and filled my mouth with cock. After only several minutes I felt him tense and then sucked the mother fucker dry.

I looked up and smiled with cum dripping over my pretty lips and kissed him, both drinking his load of love.

As he kissed me he ran his hand up my stockinged leg and to my soft bare thigh and held my pre cum soaked smooth ball sack and finally to my throbbing massive fucker which was slippery with pre cum.

Before he could suck me I said, "John I am a horny mother fucker. Don't suck me yet. Get me another drink and I'll try to get my cum filled fuck meat in your hot ass hole."

He got up and stumbled to the counter and got more drinks. He said, "Fuck yes; I'd love your big cock deep in my bowels. Fuck me until I shit cum for a week my darling slut."

While he was mixing more drinks I stood up and took my dress off. When he turned around I was standing there wearing only my stockings, garter belt, shoes and my wig and make up. The black stockings set off my soft white skin and my throbbing 8" shaved cock.

He said, "Motherfucker but you are fucking beautiful. I love you Charlene baby. I think I'm fucking drunk enough to take your huge fuck meat in my little shit hole. I've never been this cock sucking horny."

John got on his hands and knees and reached around and spread his hairy ass. I kissed his little brown hole and then stuck my tongue into the little opening and tasted his sweetness. No more cunt for me.

My cock was so slippery with pre cum as I rubbed it around his hot hole. As the hole opened up a little I tried to ease my cock head into it but it was so tight.

I reached under him and grabbed his hard prick and he came all over my hand, squirt after squirt of warm cum.

I rubbed his cum onto his ass hole for lubrication. Then I started rubbing my prick head on his brown cum covered hole. He pushed back a little and I pushed forward and my cock head popped into his ass opening.

With my hands on his hips I pushed until my fuck meat started it's trip into his dark cavity. I fucked in and out slowly until my pole was lubricated and his shit hole accommodated my rigid prick to the hilt.

"Fuck Charlene, my fucking ass has never had this much fucking meat in it. Oh yea baby, fuck me faster. Oh shit but I've never been this fucked."

I was so turned on feeling my huge cock deep in his warm moist cavity. I started fucking and pounding his mother fucking ass faster and faster. I could feel my huge load building as I pumped and he grunted.

The tension built and built until I started pumping strong streams of cum into his depths. Stream after stream until I was exhausted.

I pulled my slippery spent fucker from his violated ass and flopped over on my back. The drunk mother fucker straddled my face with his leaking ass hole and bent over and took my softening cock in his mouth and started sucking.

I kissed and licked his draining shit hole while he sucked my limp prick back to life. Then we kissed like two drunk whores, he tasting his ass juices and me tasting my slimy cock juices.

We must have passed out because suddenly there was a knocking on his door. John staggered to the door and looked through the peep hole and yelled through the door to wait a minute.

He whispered to me to go put my dress back on and do my makeup. He said there was a fucking fairy cock sucker who stopped by every so often, usually higher than a kite.

I was putting the finishing touches on when I heard, "Come on in Jeffery. Haven't seen you for awhile, what's up?"

"Hey John, I'm fucking wasted and hornier than shit. Cool man, looks like you are ready to fucking party."

"Fuck Jeffery, I have a friend over and we are drunker than shit. Wait till you meet Charlene."

Just then I stepped out of the bathroom. Jeffery's eyes got big when he saw me. John was right, Jeffery looked like a fairy. Short, slender and an assortment of rings in his ears, nose, lips, eye brows and a large stud in his tongue. He must have been all of 5 feet tall and a hundred pounds.

I said, "John my darling, look at you. Do you always answer the door naked? Are you going to embarrass me in front of your nice guest? My god, your prick is hard again."

"Hello Jeffery, my name is Charlene and I am so glad to meet you. John, please make us some drinks while Jeffery and I get acquainted."

I took his soft hand and led him to the couch. His eyes were glued to my stiff fuck meat swinging under my dress.

As I sat on the couch I made sure my dress pulled up a little so Jeffery could see my white thigh skin just above the stockings and the black garter belt. My horny 8" prick pushed the dress material up.

I put my arm around Jeffery and he slid over next to me. I told him I wished I had a son like him and asked him if he wanted to kiss me. He looked up at me and I kissed him and sucked his probing tongue into my mouth. I could feel his tongue stud as he explored my mouth.

He was breathing heavily and he rested his hand on my bare thigh. I put my hand on top of his and pulled it up my thigh and let him feel my throbbing fuck meat. He gasped as I pulled my dress up so he could see my shaved nakedness.

I rubbed some pre cum over his lips and asked if he liked my cock. He told me he would love to feel my big fucker in my mouth and suck me dry.

John said, "Take you clothes off Jeffery and let Charlene see your pretty little prick. Maybe she will really let you suck it off while I fuck her hot ass hole."

Jeffery stood naked in front of me, skinny with a 4" dripping prick. I leaned forward and gave his little wet fucker a kiss and told him he could fuck me anytime.

I bent over; legs spread, and put my hands on the couch with Jeffery under me and John behind. I could feel John's hard cock probing my shit hole and Jeffery took my rigid cock in his mouth.

I felt John's slippery cock enter my puckered hole just as Jeffery started wildly sucking me.

"Oh John honey, your mother fucker feels so fucking good in my wet ass and Jeffery baby, suck me like a good little son. Shit Jeffery, your tongue post feels so good, suck me baby."

John grabbed my hips and started pounding my ass and his hairy balls slapped my ass cheeks. While the horny drunk mother fucker rammed my slut ass hole Jeffery was a fabulous cock sucking freak.

As John shot his load deep in my bowels Jeffery gulped as I fired a huge cock load down his throat. I told them I loved them and wanted to suck my son off while daddy John kissed my dripping ass juices.

I kissed Jeffery's nipple rings on down to his very hard little prick and sucked his lovely boy part until he released his pent up load. I could feel John licking my freshly fucked ass.

We decided we were a perfect family. What more could anyone want?

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