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I met Charlene in my freshman year of college, about eight years ago. Back then she wasn't what I would consider very attractive. She was kind of tall and had very little curves to her body. Her hair was straight and un-styled; she had a flat chest, wore black rimmed glasses and had very oily skin. To add insult to injury she was the biggest geek I had ever met. But she was also the nicest person I had ever known and if I hadn't been shallow back then I could had easily dated her .

So I found myself defending her constantly throughout college. I even got my nose broken one time, protecting her from the jerks on the football team when they were pushing her around at a local bar.
After we graduated from college she moved back to New York City, while I headed out to California to start my career in the film industry as a computer animator. During that time, we stayed in contact through letters and phone calls. So when she called me up saying that she was moving out to Los Angeles I was very excited to see her.

As soon as she came out to California, we arranged to meet at the Peninsula Hotel where she was staying at, for dinner and drinks. I showed up to the restaurant around four in the afternoon and waited patiently for her to arrive.

“Steve?” I heard the soft voice of Charlene behind me.

I turned in my chair to see her and was floored at what I saw. There standing behind me was Charlene, and she was no longer the geeky girl I knew from our college days. She was about five foot nine with shoulder length red hair and emerald green eyes. Her breasts were significantly larger than I remembered, and she had more curves than a Grand pix race track. She was wearing a flirtatious plaid skirt the stopped about mid-thigh, A white blouse that had ruffles running about halfway down the front and knee high nylons that framed her smooth bare legs in between the tops of her stockings and the bottom of her skirt.

Slacked jaw, I stood up and gave her a big hug. “Wow you look fantastic!” I said to her.

She blushed slightly and said, “Well this is what ten grand can get you now of these days!” Then she laughed.

We sat down for dinner and caught up on old times. I found out that about a year after college she became a fetish model and was moving out to California because there were better opportunities for her here.
We talked about our love lives some and I found out that she wasn't seeing anyone, which perked my attention.

“So what about you? I bet all the girls here are just throwing themselves at you.” Charlene asked.
I laughed and told her that most of the ladies out here were either so vain that it would make you sick, or try to use me so they could meet a Hollywood producer so they could make it in the movies. Once they found out I was just a lonely animator, they drop me like a hot potato.

Six months after that night, we spent a lot of time together. I helped her find a nice villa up in the hills, showed her the night life of L.A. and even found myself fooling around with her some. We hadn't had sex yet but there was a lot of deep kissing and even one time she gave me an incredible blow job.
But every time I would try to get her naked she would stop me and tell me to wait. The constant teasing just made me want her more!

One night instead of going out we decided to rent a few movies and watch them back at her place. We sat on the couch, not really watching the movie, and kissed each other for a long time.
Charlene's tongue was deep in my mouth as she used her hand to massage my cock that was buried in my jeans. I squeezed her firm tits and teased her erect nipples under her flimsy T-Shirt. We were both hot and that night I knew I was finally going to have her.

In between the kissing and exploration of each other's body she whispered that she needed to tell me something before we went any further.

I lay back on the couch and asked, “Okay, what is it that you need to tell me?”
“Well…um.. you see..” She stammered with her words.

Not sure what she was going to say, I was getting concerned. “Just spill it, whatever it is I'm sure we can work through it.” I assured her.

She looked back at me and said, “I'm not what I appear to be.” She then took in a deep breath and continued to say. “I'm a transsexual!”

I was thunderstruck. This woman that I had been dating for months was really a man and had been so since the day I met her.

“Say something,” she implored me with concern in her voice. Then she followed up with, “If you want to leave I would understand.”

Quickly I thought to myself. This person beside me on the couch was more than a friend. She had become special to me. I remembered the time we shared in college and how “she” had always been there for me. “She” even took me to the hospital after my nose was broken by the “meat-puppets” of the football team.

I looked into her eyes and said, “I don't want to leave.”

With those words nothing else was said. She took me by the hand and led me to her bedroom.
When we got to the edge of her bed I kissed her deeply, caressing her body. She moaned out while my hands cupped her breasts, squeezing them and causing her nipples to become hard under my palm.
She had already removed my T-shirt and had unbuttoned my jeans. She pushed them, along with my briefs, past my hips exposing my hard cock. She grabbed onto my cock with her soft hand and began to pump it slowly. Large amounts of precum spilled onto her hand, lubing my cock entirely.

I enjoyed the hand job until she pushed me back onto the bed. There, she stood in front of me, undressing. She first removed her top, exposing her perfect rounded breast. Her areolas were perfectly round and her eraser sized nipples were poking straight out, which only got stiffer after she pinched them in a teasing manner.

Then she reached down with her hands to the waistband of her gray sweatpants. She pushed her sweat bottoms past her rounded hips, letting them fall to the floor. Totally naked before me I could see her hard-on. It was smaller than my cock; it was tapered from the mushroom shaped tip to the base where her balls met. There was a neat strip of hair shave just above it.

She crawled onto the bed and lay on top of me. I felt her firm breast on my chest as we kissed and her hard cock rubbing against my precum soaked cock.

While we kissed she started to grind our two cocks together. The feeling was odd but yet exciting. Both of us oozed globs of precum onto each other, making our cock's slick.

After a long make-out session, she brought her knees up to either side of my hips and began to ease my cock into her hungry ass.

With her on top of me, my cock pushed past the part of her round ass and found the tight opening of her hole. She slowly moved herself up and down easing it inside of herself. My cock was so covered in our combined precum that it easily slid inside of her. I could feel the tightness of her ass press against the tip of my cock and then it popped inside of her.

She gasped as my long thick cock began to go deeper inside of her. After she got used to my large mushroom head filling her ass, she eased the rest of the way down on me. She was tight and I felt every inch of my cock violate her.

“Ah fuck! It feels so good!” She cried out as she rocked her hips.

Grabbing onto her hips I helped her to rock faster. I felt her cock leak a fountain of precum onto my belly, more would squirt out each time my cock pushed deep inside her.

As we fucked she lowered her head down and kissed me deeply. Her breasts massed themselves against my chest.

Breaking away from our kiss I rolled her onto her back and pushed her legs back towards her ears. I bent down so I could lick and nibble on her stiff nipples. They stuck straight out from my flicking tongue and biting teeth.

While I fucked her she reach down and began to stroke her cock, which was shinnying in the evening light from the gooey precum that covered it.

I could tell she was enjoying me fucking her because her eyes rolled back into her head and she screamed out from my pounding cock.

“Oh fuck…. I'm going to cum!” I yelled out.

As I fucked her hard and fast, making our bodies slap together, I felt my cock began to grow more sensitive and twitch with each thrust.

“Cum for me baby! Fill my ass with your load!” Charlene yelled.

Hearing her talk dirty was all it took to push me over the edge. With one last thrust of my hips, my cock began to pour my thick cum inside of her tight ass. I filled her until my load oozed out of her tight hole that my cock filled.

I rolled off of her and she quickly move towards my cock and began to lick my throbbing cock clean. Her spit and some of my thick cum ran down my shaft, down between the crack of my ass.

She licked one of her finger and spread my legs apart. She told me to relax and that it was her turn to cum. I was so turned on by Charlene that I didn't care what she was going to do next.

With her spit covered finger she traced the outline of my puckering ass, and then slowly eased her slender finger inside of me. When she did that, my cock began to grow hard again.

She probed me with one finger than two; eventually she put a third finger in me. She was stroking my cock back to life while she fingered fucked me.

“Are you ready for me baby?” She asked.

“Fuck yea, please fuck me!” I begged her.

She got in between my legs, spreading them so she could get her cock inside of my virgin ass. Then she pushed the tip of her slender cock inside. A sharp pain rocked my body at first, but gradually went away and was replaced with the most exciting sensation I had ever felt before.

Slowly at first she fucked me, and then she began to fuck me faster and harder. My ass was stretched out by her cock but I loved ever moment of it.

Her cock was deep inside of me, massaging my prostrate. A thick stream of precum oozed out of me, spilling onto my belly. She rubbed the clear fluid on my belly with her hand and used it like a lube to stroke my rock hard cock.

While she fucked and jerked on my cock, I felt myself getting closer to cumming again.

“Oh my god.. I'm cumming!” I screamed out loud.

Charlene didn't speak, but she made loud grunting noises instead, as she pummeled my burning ass deeper. As she pumped my cock with her hand I began to shoot my load. My hot cum was thick and sticky and it painted my chest and belly.

My ass milked Charlene's cock as I came. That was too much for her to handle and she started to dump her load inside of me.

Her cock became thick as it twitched inside of me. I felt her hot load pour inside of me as she screamed in pure bliss.

She fell on top of me and kissed me deeply as her cum soaked cock slid out of my gaping ass and I felt her cum ooze out of me.

For the rest of that night and into the early morning we fucked and sucked each other until we both passed out from exhaustion.

It has been a year from that night and since then we have moved in with each other. I had quit my job at the animation company and we started our own adult movie company, specializing in transsexual fetishes. After each movie has been produced and, as they say in Hollywood, put in the can, we throw a casting party with all the stars and crew of the movie we just finished. On those nights both Charlene and I have some of the wildest sex, and I couldn't be happier if I tried.

The End.
20 comments

Anonymous readerReport

2014-07-16 21:00:51
I want a shemale friend

Anonymous readerReport

2014-07-10 03:05:38
Looking for a shemale to fuck me like in the story im 19 and skinny. Text me 720 690 0679

Anonymous readerReport

2014-04-24 23:07:31
that was an amazing story im straight and it made me horny

Anonymous readerReport

2014-04-09 00:11:36
Great story. Loved it ;)

Anonymous readerReport

2014-02-25 07:55:15
dear anonymous reader complaining about him calling a tranny a man, that's what any normal guy would think at first before accepting the fact. it's accurate, so go back to being a faggot and hop off his dick

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