This is my first story so I apologise for any mistakes made. This is also a story on my fantasy as being crossdresser and my first gay experience, so If your not interested in reading a transvestites story, then simply don't. Thanks.
Just a little info on myself: Im 16, about 5'9/5'10, I have medium longish dark hair and I have a slim body.
I had just turned 16 and my family had gone on a vacation for the weekend. I was left at home on my own because I had a school camp I had to go on, on the Sunday. I was going to be on the school camp for over a week, so my family wasn't expecting to see me until the week after. Since I was home alone all weekend, I thought I would take advantage and start wearing the women's clothing I had bought online and hid in my wardrobe. I was so extremely horny that I couldn't wait to wake up that weekend and start wearing my girl clothes. I firstly put on my black lingerie panties and bra and then slipped on my short white skirt which exposed my perfectly round shape busty ass. I then put on my tight pink top and then lastly I popped on my size 8 pair of black pump high heels. Women's shoes were definitely my favourite thing to wear when dressing up, they made me feel like a real women and a huge slut, not to mention how good they made my smooth skinny legs look. After popping on my clothes, I moved through to the bathroom where I put on my make up and straighten my hair until it look like a short girls bob haircut. I also painted my nails a bright red colour, and waxed all hair off my body.
After finishing putting on my makeup, I heard a van pull into my drive way. I looked out the window and saw what looked to be a delivery man. I heard the doorbell ring. I was a little scared and nervous at first since I was dressed up like a little girl slut, but I was so horny that I wanted to answer the door for this mysterious man. As I slowly opened the door, I saw this tall muscular looking 30 year old man looking me up and down. I began to bite my lip and ask the man what he was after. He began to stutter and told me there was a delivery of a pair of high heels for someone. I told him they were for me and he asked if I could sign a sheet of paper which confirmed my delivery package. I told the man I would be right back with a pen to sign the piece of paper.
As I returned to the front door, I couldn't see the man in my sight at all. But as i slowly turned around, I saw a shadow jump out from behind the wall and grab me with force. I began to twist and turn, but I was helpless with the strength of this elder man. He began wrapping duck tape around my mouth and rope around my wrists and ankles. I began to squeal and scream as the man picked me up and hurriedly carrying me out to his van.
No neighbour could hear me as I could hardly make a noise with the duck tape over my mouth. The man opened the back door of his delivery van and chucked me on a bed which was lying in the back of his van.
The man hopped into the drivers seat of the van then turned around quickly and injected me with sleeping fluid as I wouldn't stop squealing and moving around.
After about five hours of sleep, I finally woke up in the van and noticed that we were driving out into the middle of no where which looked like the desert. I said to the man "Please don't hurt me Mr, ill doing anything for you if you just please dont kill me". He laughed and replied "I'm not going to kill you! I just wanted to have a bit of fun thats all". I was a little worried and replied "What kind of fun?" He smirked and pulled over to the side of a long dirt road in the middle of the desert. He then said "Why don't you hop in the front with me and ill show you?"
I replied with a worried voice "If you say so".
I hopped in the passenger seat and saw the man looking me up and down. I looked over at his jeans and saw a huge bulge in his crutch area. I began licking my lips and rubbing my crutch area as if I was rubbing my own clit. He said to me "Why don't you start sucking on my cock to start this fun?" I saw him unzip his jeans and then flopped out the thickest and vainest 8 inch cock id ever seen. I began drooling and took a huge swallow as I was about to suck on my first ever cock which happened to be the biggest cock Id ever seen. The man grabbed my head with force and shoved my head down to start sucking his dick. It tasted amazing and I couldn't get enough! I began licking his shaft while he drove and spitting on the top of his tip.
After about 10 minutes of sucking this enormous cock, he pulled onto the side of a dirt road which led us into some hidden bushland. As soon as he parked the van, he reached over and tossed me into the back of the van. I was beginning to feel extremely horny since I was out in the middle of no where with this man I hardly knew and I was dressed as a little slutty girl and this man had no idea i was a young teenage boy.
As i landed in the back of the van, i turned my ass around towards him and said "Come her big boy and fuck this dirty little whore" He moaned with fury and jumped into the back of the van naked.
He turned me over onto my back and lifted my legs in the air. He took off my high heels and began sucking on my red nail painted toes. I began sweating heavily in the van as the hot sun was steaming through. The man began licking the sweat off my feet and then i grabbed his cock with my feet and pulled him closer towards me.
He turned me on my knees and push my head into the floor while i held my ass in the air.
I shouted "FUCK ME IN MY TIGHT ASSHOLE WITH THAT BIG COCK!"
He ripped off my skirt and panties and saw my 4 inch cock droop down. His jaw dropped and he just smirked and said "could this get any better?" He then slapped my face multiple times as hard as he could across my face with his huge cock.
I was then ready for this huge cock to be shoved in my tight teen asshole. He began impaling my tight asshole with his huge cock. I could feel every inch dig deep inside of my asshole and it sent me crazy. "Keep fucking this bad girl with your huge cock baby!"
I heard his moaning become heavier and his thrusts began to become harder and deeper as his sweat began to drip onto my back. I could tell he was close to cumming so i got him to turn me on my back and start fucking me furiously fast. "I want you to fill my asshole full of cum baby!" I felt his balls swell up and his veins in his cock began to bulge and impale the sides of my asshole inside. Then all of a sudden he let out the biggest moan!
"Yes cum for me baby! Thats right deep inside of my ass!"
I felt the cum begin to fill my asshole like a water hose. His cock began to swell as he dumped huge amounts of cum into my asshole. My eyes began to roll to the back of my head and i began curling my toes as the pleasure of my asshole being filled with cum sent me insane. As soon as he pulled out, I exploded my load all over myself, and the man began to lick off every drip of cum off my body.
All i could feel was my asshole being full of thick cum which began to bubble deep inside and drool out of the top. I was so tired from being fucked for hours that i decided to fall back to sleep again. And before falling asleep, i hear the man whisper, "The fellas are gonna love you!" And there i was drenched in sweat cuddling this elderly man with an asshole full of cum.
After a huge nights sleep, I was awoken to the man opening up the back door of the van and I noticed that I was in some place new. It looked like a warehouse in the middle of the desert which was surrounded by big trucks and motorcycles. I then look at the man and he says to me with a serious look on his face "Welcome to your new home slut!"