It’s been a while since this happened but I remember it like it was yesterday.

I had just turned 17a few days before my favorite holiday. I’m a good looking guy, 5’6” maybe 140 lbs. Not the biggest guy in HS but not the smallest either. I have what I call camouflage colored eyes. Sometimes their brown, others green depending on what I’m wearing. I have a nice slim toned body from track and always loved being outdoors.

Yep, Halloween was right around the corner. Trying to come up with a good costume was always a tough thing to do. I needed help coming up with a good idea or two, asking my friends and family, easily discarding their ideas of zombies, bums or a football player… I asked a few teachers at school. My English teacher, Mrs. Roberts laughingly suggested I dress up as a cheerleader. It’d be different but I don’t see myself doing it for obvious reasons. But after telling my girlfriend, she was all over it and decided to make this her thing to do! I couldn’t argue with her as excited as she was so I went with it. We had plans to go to her older sister’s Halloween party at her Dorm upstate so no one would know me and it was all for fun anyway.

So the morning of the party came. Sherry, my girlfriend, brought the costume over along with hers. She told me last minute she was going as a Vampiress. I couldn’t wait to see her in her costume. We fooled around a little then about 2 we got down to business of getting dressed up. She had me shave my legs and the little bit of hair on my arms and face, armpits came next, which I argued about but eventually lost. Oh well, get into character right?

Once all that was done, it was time to get dressed. First, satin panties, then cheerleader knickers, short white and blue skirt. Bra and some silicone breast forms. Well, the forms kept moving around so Sherry decided to glue them in place. After that was done, the bra went back on, followed by the tightest sweater I ever wore. I have somewhat short hair, so she pinned a black wig on my head. She followed that up with some knee high socks that went above my knees and finally some uncomfortable high heel shoes. Thinking I was done, I went to look in the mirror, that’s when she tackled me… literally! “Not until I’m done!” she said. Sherry sat me down in front of her and went to work putting make up on me. After what seemed like forever, she said I was done. But I was not to look until she got dressed. It took her about an hour, where I had time to take a few shots and drank a beer. By this time, the satin panties and the weight of the breast forms were making me incredibly horny. Finally, she said lets look in the mirror. I gotta say… she looked hot, kinda like a blonde Elvira. Surprisingly, I looked passable… even cute. A little slutty but I was kinda buzzed so it was all good.

I took a few more shots and we were off. I brought a 12 pack along for the ride and only had a few more left when we got to the party. Once there, I was extremely nervous but thanks to the alcohol, got into character. Sherry was playing her part too and we were both having a good time. A few times I seen guys talking to her, doing jelly shots with her, even grabbing her ass. I was not happy about that but was having my own good time to do anything about it. About half-way thru the party I noticed I pretty much always had a small crowd around me and guys handing me drinks. A little later my crowd grew quite a bit. Sherry also noticed this and got extremely jealous and decided it was time to go before something happened.

Once we were in the car, she was yelling at me for being such a slut. I thought, no one grabbed my ass or tried anything. I mistakenly told her she was jealous because I looked so much better than her. After that I got the silent treatment. I thought and finished the last few beers. We needed to stop for gas and she told me to do it. So I got out, went in to pay for the gas and realized I didn’t have any money. I went back out to the car, but she was gone! The bitch left me there! And I was dressed up as a slutty cheerleader!

I wanted to call someone but couldn’t. Wtf am I supposed to do… I went back inside, sat down and drunkenly tried to figure out my options, which weren’t many. I sat there for a few minutes, head down when this big truck driver said to me, “It looks like your friend left you, want a ride?”

“Are you kidding? Of course I do. Thank you so much!”

We walked over to his big rig, he opened the passenger door for me and helped me climb into the cab, squeezing my ass at the same time. Honestly, I kinda like it. Being treated like a woman by this huge man. He climbed in and we started rolling. He kept sweet talking me, telling me how beautiful I looked. How hot I was making him! I didn’t know what to say, I think all I did was blush.

We were about halfway to my house, a good 45 minute drive left to go, when Joe, the truck driver said he had to take care of some business and pulled over. I thought he was gonna get out and water the plants. You can imagine how surprised I was when he jumped back into the sleeper and yanked his pants down, pulled out an enormous cock and start stroking it. What the hell is happening? Even more shocking was the fact that I couldn’t keep my eyes off of it or the fact that I was pinching the nipples on the breast forms and rubbing my crotch like I had a clit!

So here’s this guy stroking his HUGE cock while I watched with all the interest in the world. After a few minutes he said his arm was sore and could I take over? I think I jumped in the sleeper and had his cock in my hand in less than a second. What the hell was I doing? This cock had to easily be 10 inches with the largest mushroom head and here I was stroking it, mesmerized by the size, the feel and the girth of it.

Without know what I was doing, the next thing I know, I’m tasting it and enjoying it. I slowly start taking more and more of his cock into my mouth and loving it. I’m drooling all over his knob and using that spit to lube the rest of his shaft. I was so into what was in my mouth, I didn’t notice he was playing with my asshole, squeezing my fake tits or even noticed I had a very erect cock of my own. He’s oohing and aahing, fingering my tight asshole, which was feeling amazing, no pain or it even seems like my asshole was drawing more of his fingers into me.

After a few minutes of this he stands up and flips me around on my knees and lines that monster of a cock up with my ass. I realized what he was doing and tried to get out of his grip but was unable to, he was just too strong. As he slowly sunk inch of incredibly hard inch into my backdoor the more I felt like this is where I was supposed to be. Sounds weird, I know. But this just felt so much better to me than putting my slim 5 incher into Sherry. Once I could feel Joe’s massive balls resting against my silk panties, I knew I was his bitch. He took his time and let me adjust to being stretched so thoroughly then began to pick up his pace. Next thing I hear is me moaning like a whore while bucking my hips back to meet his, trying to get every part of his cock inside me that I could. He loved this and turned onto his back, pulling me on top of him so I could ride his cock for all I was worth. I took him deep and shallow, slow and fast. Whatever felt good, I did. Joe told me he couldn’t take it anymore and pushed me off him, stood up and grabbed my face and blasted a huge load on my face, in my mouth, in my wig, the sweater. (which had so much cum on it, I had to was it 3 times to make sure it was all off.)

I laid in the sleeper for the rest of the way back, cum drying all over me, my ass felt like it was beyond empty. When the truck stopped again, I got up, Joe gave me his phone number and got out of the truck and Joe pulled off. Me still in a stupor, trying to figure out exactly what happened and why did I like it so much?
I had a moment of clarity and realized I never told Joe where to drop me off at. I looked around but couldn’t figure out where I was. I noticed a seedy looking motel across the freeway and an odd looking shack of a building directly in front of me. No sign or anything, just a nonde white building with 4 or 5 cars parked in the area and a lamp post….

Hope you liked my story and want to read the rest. Leave comments, good or bad and if your interested I’ll post more!

story by: trans_love

Tags: fiction young anal transvestite oral sex transsexual transgendered sex story

Author: trans_love

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