Transgender
2010-07-29
My name is John. I am 22 years old, 6’0” and about 180 pounds. I have never considered myself gay but I have had the occasional fantasy. I am a naturally curious person so when I started having gay fantasies, I started experimenting with household objects (cucumbers, plungers, etc. ) and started trying on make-up and lingerie. I loved to dress like a girl and fuck myself stupid with toys.
I have been friends with Justin (23, 6’1” and about 130 pounds) for several years. We got to be pretty close friends. We would go swimming and if no one was around, we would skinny dip together. We would watch porn together and things like that.
One day (after an exceptional sex dream between Justin and I) I decided that toys were no longer cutting it. I needed a real cock in my ass. Unfortunately, the only guy I felt comfortable around was Justin and I didn’t want to ruin our friendship. I devised a plan, I would send Justin anonymous emails asking for sex and see if he responded. A poorly thought-out plan. He never answered.
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So I tried a different tactic, I asked him if he had ever thought about sex with a guy or experimented with his ass.
“I’ve wondered”, Justin said. “But never tried anything. ”
Then he told me about some emails he had been getting.
“Do you know who curious-george0245 is?” he asked. “Because he has been sending me emails asking for sex. ”
“No, I have no idea,” I replied. I had chickened out. That was my chance to tell him what I really wanted.
Then for a while life continued normally. We still hung out a lot. I still wanted him to ravish me but never told him and we continued to skinny dip and watch porn together.
We decided to skinny dip again one summer day. I’m not sure if he noticed but I tried to sneak a look at his cock whenever I could. We came back to my house and he sat down to watch some TV.
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“I’m just gonna go get changed”, I said.
I hurried up to my room and thought, “It’s now or never”. I shaved my legs and ass and anywhere else I had hair. I then slid into a black silk thong and matching bra. I slid some black stockings on and shivered at the tingle I got from putting them on. I applied my make-up next, some foundation, some blush, some dark eye shadow, and finally a cherry red lipstick. I slipped into a low cut black dress and put on a pair of four inch black heels. To finish it off, I put on a black bob wig and stood back to admire my transformation.
“What took you so long?” Justin asked as he heard me coming down the stairs.
“John’s not here”, I said seductively. “Im Joanna. And you’ve been a bad boy. Now get out of that wet bathing suit. ”
He fumbled for the not as he let his suit slide off and his 7” cock sprang to attention.
I got to my knees in front of him and slowly began to lick his swollen head.
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I parted my cherry red lips and slid his hard cock into my hungry mouth. I started to slide slowly up and down his glorious cock. I reached up and started to massage his balls with my left hand and started to stroke his cock with my right.
“Holy shit Joanna, you’re fantastic!” Justin said when he could catch his breath.
I bobbed up and down faster and faster. I could see he was getting close. I sucked as hard as I could as I moved my mouth up and down on his cock. I swirled my tongue around inside my mouth to add to his pleasure.
“Oh my God Joanna! Im gonna cum!” Justin yelled.
I could feel his cock swell as he released stream after stream of hot, sweet cum into my waiting mouth. My choices were drink or drown so I swallowed every last drop.
“That was amazing!” Justin said as he slumped back onto the couch.
“We’re not done yet”’ I told him. “See, you’re still hard. ”
I reapplied my lipstick and sucked him a little more to get him lubricated.
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Then I got on my knees on the couch and put my hands on the back of it to steady myself.
“I want that hard cock of yours in my ass. Now!” I yelled.
He positioned himself behind me and he pulled my dress up over my ass. He pulled my thong aside and started to prod my asshole.
“Don’t be nice. ” I told him. “I want you to fuck me raw. ”
He didn’t need to be told twice. He rammed his cock in as hard as he could. I screamed with a mix of pain and passion. He started to fuck me very slowly.
“I cant believe this is actually happening. ” I thought.
He then pulled his cock all the way out of me.
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“Hey, I didn’t tell you to stop. ” I said.
Then he rammed his cock into me again. My ass was stretching to accommodate him and I loved every minute of it. He was grunting as he would pull almost all the way out then plunge his cock back in.
“Harder. Oh yeah”, I said. “Fuck me harder!”
I started to lean back into him when he would thrust forward. I could feel all 7 inched of him deep in my ass. I could feel him start to swell again and I knew what was coming.
“Oh fuck!” Justin yelled. “Your ass is making me cum!”
I pushed him back and his cock slid out of my asshole, which was already missing the feeling of having a huge cock in it. I turned around to put his cock back in my mouth but I wasn’t quick enough. He shot several streams of his delicious cum onto my face and into my wig. He looked at me, drenched in a shower of his cum, and said…
“You don’t know how long I have wanted to do that.
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