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The story of Jane part 1, Becoming Jane

Transgender
2010-04-23

I pulled my car into the drive way. I was extremely nervous and even more horny. It had taken me half an hour to drive to her house. I had been out earlier and was about to call it a night when she had called me. I had met her on an online dating site. Her name was Ms. Chyna. She was a beautiful full figured black woman with a huge cock.
I’m not sure when it was exactly that i became interested in dick. Im good looking, but my shyness always made it hard for me dating girls. I am 5‘9“ and about 135 lbs. I have blonde hair, its not long but its not short either. I am thin but not very muscular. My first encounter with another man was when i was seventeen.
I had just broken up with my girlfriend and was very lonely. I was talking to an older man on a web site and we decided to meet up.

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   I met him in a pharmacy parking lot. I got in his black jeep grand cherokee. His wife was home, so we couldn’t go back to his house. He had a friend that was out of town who said we could use his garage.
He made small talk on the way to the house. I lied, i told him i was eighteen. He was just your average middle aged man who liked to fuck younger guys. When we made it to the garage he folded down the seats in the back of the jeep. He lay down a comforter and we climbed in the back. He kissed me deeply. His facial hair was rough against my face. I really didn’t get much out of him stuffing his tongue down my throat. I was relieved when he stopped kissing me and unbuttoned his pants. He slid his pants and boxers down to reveal his semi hard penis. It was about six inches long and was i would say average thickness.

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I grabbed his cock and began jerking it. I moved my lips to the head and began to run my tongue around the head of his hardening cock. He let out a little moan. I ran my tongue up the length of his dick. I then made my first attempt to suck a dick. It wasn’t overly large, but it was awkward having it in my mouth. I opened my mouth wide and got about an inch and a half in. I closed my lips tight around his cock and sucked as hard as i could. I slowly began sliding my lips up and down his cock while i jerked him off.
“Yea, suck that dick, yes that feels so good,” he moaned.
I began to pick up speed. He put his hands on the back of my head and began pumping his dick into my mouth. He started pumping it deeper and deeper into my throat. When he got it about 4 inches in i started to gag. He let go of my head and let me come up for some air.

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   I began sucking it again. I had fantasized about this moment four years and i barley could believe it was actually happening. He unbuttoned my pants as i sucked his cock. I slid my pants and boxers down. My hard 7 inch dick popped out. He began to rub and jack my dick as i sucked his.
“Let me fuck your ass,” he said.
He positioned me with my head against the front seats of the jeep. He pulled out some lube. He lubed up my asshole and slid a finger in. I let out a moan, it felt so damn good. He began to finger fuck my ass. He then put to fingers in and kept right on pumping them in my ass. Then he pulled them out. I felt the head of his rock hard dick come to rest against my asshole.

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   he lubed it up and put some more lube on my asshole.
“Just relax, i’ll be gentle,” he said.
He began pushing the head of his cock inside of me. It hurt bad. He told me to pull my ass checks apart, i did. He pushed a little more. Finally his cock was inside of me. He just let it sit there a second and let me adjust to having a dick inside of me. As i started to get used to the feeling it started to hurt less. He began to slowly pump his hard cock in and out of my ass. after a minute or so he started to pick up speed. He was moaning and slapped my ass a few times. He reached his arm around my stomach and jacked my dick.
He started picking up more speed. He grabbed my ass with both his hands.

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   He was now pumping his entire cock into my asshole, his balls where slapping against mine. It felt amazing. I began jacking my on dick. With his cock pumping in an out of me it didn’t take long before i was going to cum. I was moaning and almost couldn’t get my breath when i told him i was going to cum. I jacked my dick as fast as i could, and the the thick rope of cum erupted out of my dick. He grabbed my ass and shoved his cock as deep as it would go in my ass. He blewhis load inside of me, filling me up with his cum.
We sat there a moment out of breath. He then pulled his softening cock out of my ass. I could feel his cum dripping out of me. He grabbed a towel and cleaned himself up. He then gave it to me. I cleaned myself up and got dressed. He drove me back to my car and dropped me off.

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That was my first experience with a dick. Now over three years later i had just pulled up in front of Ms. Chyna’s house. This was going to be my second time have a cock inside of me and my first time with tranny.
I parked my car in the driveway. The garage door was already open. I walked into the garage past her truck and knocked on the door. A moment later it opened. There she stood. She was 6 feet tall. She was thick but not fat. She was wearing a skimpy black dress.
She took my hand and lead me into the bedroom. A porno was playing on her tv. The volume was turned down, but i could still hear the girl in it screaming as a man pounded her ass.

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   Ms Chyna wrapped her arms around me. She kissed me deeply. Her tongue slid into my mouth. My hands found her breasts. She was about a b cup. A started rubbing her tits as we kissed. I felt her nipples getting hard.
She pulled the dress down to reveal her beautiful tits. I began to lick and suck her nipples. She told me to take off my clothes. I did. She put her hand on my shoulder and gently pushed me down on my knees. She pulled the short dress up. Her big ten inch black dick popped out at me. It was by far the largest cock i had ever seen.

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   I grabbed her dick and pulled it into my mouth.
She was already hard. It was so big i could barely get it in my mouth. I worked at it and after a moment i got it in. That dick was so good. I licked it and jacked it. I slowly started shoving it deeper and deeper down my throat. I sucked as hard as i could. I was in heaven.
She began moaning. She pulled her dick out of my mouth.
“Get up on the bed, i want to fuck your white boy ass” she told me.
I got up on the little bench at the foot of the bed. She put her hand on my head and forced it down into the mattress. She lubed up her dick.

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   She told me to relax as i felt the head of the huge black cock press against my asshole. At first it wouldn’t go in but, after a few minutes she was inside of me.
She started pumping my ass slowly as she held my head down. She began moaning and began fucking me harder and faster.
“That ass is so tight it feels like a blow job,”she said.
She kept picking up speed until she was ramming all ten inches of her cock inside of me. At first it hurt. The pain finally went away. I was in heaven with that big black cock fucking me. All of a sudden she slammed the entire length of her dick into me and screamed.
“I’m cumming!”
I could feel her cock pulse as she shot her load deep into my ass. A moment later she pulled it out some. She than began working it in and out of me again. Once again she picked up speed. She fucked me for all i was worth until she came inside of me again.

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This time she pulled her dick out. My asshole felt wide and hollow without it in me. She went to a desk and brought out some flavored lube.
“Eat my asshole,” she told me.
“Yes, Ms Chyna. ”
I put the cherry lube on her asshole and began licking it. She began moaning and grinding her ass on my face. I stuck my tongue out as far as it would go and tongue fucked her ass. This really got her going. She was moaning and tugging at her beautiful dick as i tongue fucked her asshole and jacked my dick.
“Give me some more of that booty,” she said.
I laid down on the bed. I was on my back with my legs hanging over the side. She grabbed my legs and held them up. She positioned her dick against my asshole.

 

   She slid it into me easily this time. I felt more intense this time. She really started fucking me hard, pulling nine of the ten inches in and out of me. I was moaning and screaming. My dick was so hard it felt like it was going to bust.
She fucked me like a little slut for ten minutes. She pulled her cock out of me. My asshole felt like it could have been the grand canyon. She climbed up on top of me. She positioned her ass over my rock hard cock. She she dropped down on my dick. Her asshole felt so good, this wasn’t going to last long. Her dick was bouncing around on my stomach as she rode mine. I took her ten inches in my hands and began to jack her desperately as she rode my cock.
I felt my oncoming orgasm building.

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   I screamed that i was going to come. She rode me even harder. When my dick erupted inside of her, she came to. Her cum shot in thick ropes on my chest. She lay down on top of me with my cock still in her and kissed me.
We lay there for what seemed like hours. She got off of me and we cleaned ourselves up. I began to get dressed. I was almost dressed when she decided to fuck me again. I was wore out from our time together already, but i let her have my ass again. She fucked me hard and fast. When she was finished i got dressed. We said our goodnights and i left. I drove home that night sore from the good fucking she had gave me.
It was then that i knew i wanted to be a tranny

to be continued.

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