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RandomDude Member Since October 19, 2009

My Gangbang

RandomDude on Transgender Stories

It was junior year of highschool.  There was this one girl who I liked but was too afraid to do anything about it.  Her name was Jessica.  I thought she was too "cool" for me.  She always hung out in a group of 3 other girls.  She was short, about 5'2, her body was alittle plump, not too fat, but not too thin, just right.  Her 2 other friends were similar to her, except thinner.  Their names were Michelle and Bobby.  But for some reason, something was different that year. They were kind of like outcasts.  They just hung out with themselves and didn't socialize much.  One day I overheard the girls talking, they said something about a sleepover at Jessicas house.  This was going to be my chance!

Later that night, I drove my car and parked
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it on the street right before.  I slowly sneaked to their house, I noticed there were no cars.  My heart started thumping.  I walked as quietly as I could, and peaked through the window, they were sitting in their pajamas in a circle talking to each other.  I couldn't make out what they were saying.  Then all of a sudden, Michelle reached over and felt Bobby's croach.  All of a sudden I began to get excited.  I reached into my pants and started rubbing my dick.  Then I lost my balance and fell on a back.  I knew that was bad as it made alot of noise.  All of a sudden, I saw the girls through the window,and they saw me.  They opened the window and brought me inside.  They had wierd smirks on their faces, I thought it was hot, but they looked as if they had evil intentions.  Then Jessica asked me, "How much did you hear?"  I said, "Nothing".  She then looked at my croach and noticed my boner.  Her eyes were fixed on it, and she smiled and started crawling towards it. I said, "You wanna taste it?" and she replied, "only if you taste mine first" All of a sudden Michelle and Bobby grabby each of my shoulders and put me flat on the ground.  Jessica then took her shirt off.  I noticed her hard nipples, my penis began to grow and I knew it was going to be a night I was never going to forget. She then took her pants off and I saw her penis, for the first time.  She asked me, "You want it?"  I paused for a second and said, "hell yea"  She crouched on my face and put her dick in my mouth.  I could feel the warmth and tenderness.  It felt so good, I got hard.  Michelle then unzipped my pants and took em off.  I unbuttoned my shirt and threw it against the wall. I sucked on her dick for a good 5 minutes.  She then backed up, lifted my legs and pushed them over my shoulders.  She spit on my asshole and rubbed her spit all around and slowly lowered her penis into my ass.  I could feel her warm dick occupy space in my body.  It felt so good.  She thrusted in and out, and my penis hardened even more.  Then Bobby stood over me, naked, and she too had a penis!  She lowered her dick into my mouth and said, "Suck it you slut"  It tasted so good I sucked like there was no tomorrow.  Then Michelle came in and put her mouth over my penis and began to suck.  I was moaning like a little girl.  This was the greatest experience of my life.  Then Jessica screamed, "I'm gonna cuuuummmm" All of a sudden I felt my ass fill up with her fluids. Shot after shot my ass was getting filled.  Bobby said, "My turn to fuck him, move aside!"  Bobby and Jessica switched places, and I had jessicas dick in my mouth.  I could taste the cum around her penis, it tasted great.  Michelle then got up and put her dick in my mouth.  2 dicks in my mouth at the same time.  I sucked and sucked, Jessica then started giving me a blow job.  Then, Bobby came out of my ass and right over my mouth,  Michelle was pointing at my mouth too, pumping as hard as she could, they were moaning, and all of a sudden I felt shots come into my mouth from 2 different directions  It tasted great.  I didn't swallow it, yet, I just held it in my mouth.  Right then I felt like I was about to cum, I held it in until the last second and I could feel my penis opening and closing, it all went into jessicas mouth.  She then put her face infront of mine, and we locked lips, I could feel more cum loaded in my mouth.  I let my tongue swim in it  I then took 2 big gulps and it all went down.  I was done.  The girls pushed out every last bit of cum onto my tongue. 
I got up, put on my cloths and said, "Same time next week?"  They all smiled and said, "Fuck yea"  I smiled and walked out the door.  I knew my life was never going to be the same.

Roommate

RandomDude on Transgender Stories

It was freshman year of college.  The college had just started a new coed dorm which I signed up for.  On the first day, I was excited to see who my roommate was.  I was sitting on my bed reading a book, and I heard the doornob turn.  It was my roommate.  She was medium height, dark skinned, red hair, she wore a tight pair of jeans and heels.  What really jumped out at was her tits, they were huge!  Her face was pretty, but there was something about her that seemed odd.  I went and shook her hand, her name was Kim.

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The next night,

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she was out partying while I sat in the dorm and surfed the net.  I started looking at some shemale porn, it really got me hard.  I looked over at Kims drawer and saw a thong sticking out.  I decided I would give them a try.  I opened her drawer, and picked out the black thong.  I took off my pants and put it on all the way.  To the side of the drawer, I saw some black stockings.  I got a sudden impulse to go all the way.  I put on the stockings, they felt great, hugging my legs.  I was missing something, the bra!  I saw a black one and slipped it on.  All I had left was the makeup.  I put on some red lipstick and pink eye shadow.  I was one horny bastard.

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All of a sudden I heard the door open, it was Kim and she saw what I was doing.  I told her to not tell anyone.  She said,   “So you like chicks with dicks huh, you little slut.”  She had a weird smirk on her face as if she was going to blackmail me.  I said, “Lets just keep this a secret between you and me”  She locked the door behind her and slowly started walking towards me.  I could see her eyes focused on my boner, my heart was racing. “Kim, please…” I said, but she just put her finger over my lips to tell me to keep quiet.  She slowly leaned over and kissed me.  It had always been a fantasy of mine to fuck her, it was as if my dreams were coming true.  She took my hand with both of her hands and put it on her chest.  Slowly, she slid it down to her crotch and slipped it in her pants.  Before I knew it, I had a hand full of penis.  My blood rate shot through the room.  “You want some” she said.  I replied, “I want the whole thing,”

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I went and sat on the bed, stroking my dick to keep it hard.  Kim took off all of her cloths, I finally got a view of her penis.  It was a good 10 inches long.  I layed down on the bed, and she layed right on top of me in a 69 position.  I sucked her dick like there was no tomorrow.  The smell of her ass was nasty, but in a way it smelled good.  She then got up and said, “You’re my bitch tonight”  I put my legs over her shoulders as she got behind my ass.  Slowly I could feel her dick penetrating me.  My dick got rock hard instantly.  She got her hand and began stroking my dick.  She was thrusting in and out for the next 5 minutes.  It was heaven on earth, it was the greatest feeling in the world.

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I couldn’t hold it in any longer, and a giant shot of cum shot straight up and landed on my chest.  After 4 more shots of cum pooling on my body, it stopped.   Then Kim screamed, “I’m gonna cum…” and took out her dick and put it over my face.   I opened my mouth wide and closed my eyes.  I could feel shots of cum hit the back of my mouth.  A few seconds later, my mouth was full of her cum, and I swallowed it all.  As I lay there, she started licking the cum from my body.  When it was all cleaned up, she put her hand behind my neck and raised my head to kiss me.  I could feel her tongue as she was spitting the cum into my mouth.

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At the end, she rolled over and lay next to me. “Next time, your on the bottom” I said.  And she replied, “Yea, wait till you meet my friends”  My dick rose up again, I couldn’t wait for the next day.

Dorm Room Fun

RandomDude on Transgender Stories

I came back to my room early that day, I decided not to go to my second class of the day. As I opened the door, I caught a glance of my roomate on his laptop. He was watching short clips of shemale porn. A feeling of surprise and excitment shot through my mind. He looked back and realized that I had seen it. He was clearly embarrased, he closed the browser as fast as he could and tried to explain how it just came up, he didn't mean to look at it. I saw this as an opportunity to finally tell someone about my addiction. I told him it was ok, that I too love shemales. An instant connection was made. We had just moved in two weeks earlier, so we barely knew each other.

His name was Ryan, he was a large white guy. He was a backup linebacker on the football team. I always caug
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ht glimpses of him changing and got jealous of his body. He could probably take anyone on in a fight and get any girl he wanted. He was invinsible, but now I knew a secret about him, that no one else knew. I, on the other hand, didn't have the body he had. I was a 5'11 mexican. I got too lazy to cut my hair, it was at about shoulder length, but i shaved still. I shaved it the shower, so it made it conveniant. I had shaved my pubes and my ass too, just to get a clean feeling. My parts felt like rubber afterwards.

That night, ideas rushed through my head, as I thought about it, I wanted to fuck him more and more. I decided I would make my move the next day. I had it all planned out, he wouldn't be able to do anything about it.

The next day, I left for my 9pm class, as usual, but instead I went over to the local JP Penny. Wearing my big trenchcoat so no one could recognize me, I bought a pair of black stockings, some black panties, and a black bra. I bought a bunch of random makeup, I didn't even realize what I was getting. I went over to the dorm bathroom, and began changing. The stockings felt so good, they hugged my legs and gave me that tingling feeling. I put on the rest of the makeup, the blue eye shadow and maroon lipstick. I looked so sexy in the mirror. I pulled out a bottle of baby oil put a large dab on my hand and started rubbing my ass hole and nuts. It felt so smooth down there, I was finally ready. I put on my trench coat and quickly went over to my room. I quietly opened the door and tip toed inside. He was really into the computer, I saw him hunched over, wacking off while watching a man tear apart the ass of a shemale.

I whispered in his ear, "how would you like to be him?" He turned around like a deer in headlights, he started rambling about how it wasnt how it looked. I put my finger on his lips and stood up straight infront of him. I took off my trench coat and dropped it on the floor. I told him, "how do you like this?" I could see the excitment in his eyes, his dick started growing even more. I knew at that moment that he was mine. I felt like such a whore, but it felt so good, it had always been a fantasy of mine.

I bent over, grabbed his head, and stuck my tongue in his mouth, we made out for a good 5 minutes. It got us both in the mood. He took off his shorts and shirt all the way and layed down on the bed. He was so buff, and his six pack was so hot. I got up on my knees and began pumping his cock. It was a good 7 inches, but it was very wide. I took my hands off and only used my mouth. I began going up and down, getting it lathered up for what was to come next. I tried to go as deep as possible and almost choked. It was so large and warm, it tasted so good. He got up and I took his spot laying on my back. He stripped off my panties, revealing my hard boner. He lifted my legs over my shoulders, and guided his dick to my ass. I was already lubed up. With one thrust, he shoved the head of his dick in me. I could feel my ass being occupied by his cock little by little until it was completely in. It was an amazing feeling. My cock became rock solid. He increased his speed until his was pumping me fast. It was like heaven on earth. My own dick was getting ready to explode.

He told me he was about to cum, he quickly pulled out and shot into my mouth. I felt my mouth get filled up by his salty fluids. I swallowed all of it in two big gulps, showing him my mouth. My own dick was throbbing. I told him to get on his knees on the ground. I stood up and made him suck my pole. I jizzed all into his mouth. I could tell he was holding it in. I told him to stand up, I leaned in and kissed him, i could feel my cum in his mouth flooding into mine. We kept kissing for a minute. My own salty cum was now all in my own mouth. I swallowed it all.

That night, I didn't have to sleep in my own bed. We cuddled all night, talking dirty, kissing. He told me he had friends that he had to introduce me to. My dick instantly got hard, thinking of the possibilities. For now, I had my fuck buddy, my man, I could try anything with him, and I planned on doing so.