Misadventures of a sissy boy

I just turned 18 y/o and I decided to move out on my own without a room mate. I found a great job that allowed me to payoff my bills and put a little away.

I am a 135 pound skinny nerd boy who had been outside of the puberty experience. My body figure was a skinny curvey waist. And I noticed through out my schooling I had a bubble butt. Playing sports my friends called me buns. I worked out at a local gym. I remember a couple of guys checking my butt out but did not think anything about it. I knew about sex with man and woman by looking at porno. But never knew what gay sex was all about.

One night I was at my computer looking for porn video. And a pop up plastered itself on my screen. Forever changing my life. It said do you want to see your favorite shemales in action being fucked by hot men.
I was like what is a shemale? So i hit the button. I saw the gorgeous women with curves tits tan-lines and nice bubble butts. I saw the action. And I loved it. I was looking at the shemale and she loved that a guys penis was either in her mouth or pumping that delicious bubble butt. I came upon Patricia Araujo.

Man she was good. I was tingling in my ass when the top was fucking her in an Indian position. All hear is oy oy oy destozo. Man I wanted to be her. But reality hit. If I am gay. I am to chicken to come out. Even asking my parents to let me go through the partial procedure to becoming a transgender woman. So I browsed more.

Saw do you want to become a sissy boy? I immediately said you damn right I want to be one. I hit the button and sissy hypno porn came on. The process of like hypnosis to convert you to being a pathetic sissy to serve men and their needs. A woman’s voice saying words that your butt was a pleasure hole for men to deposit their sperm into. I watched sissy hypno for over 2 months. I could not get enough. I wanted get out and do it now.

I would use walmart to buy a few womens clothes by using self checkout. Then I relized i could buy online. Bought sexy panties, thongs, skirts, tight shorts, blouses and lingerie. Bought a whig that was blondish brown. And makeup to complete my look.

In a town one hour away I saw a class how to dress up and if you want try out a man to fuck you in your new life. I just wanted the class. But I was curious. So I signed up. It was held on a Wednesday. When I arrived they take you and have a one on one tutorial. My teacher was a gorgeous trans. Named Val. She asked me if I was a virgin I said yes. She smiled. She applied my makeup allowing to work on it too. Then I dressed up. She said wow you look hot. Do you want to walk the floor and see new sissies getting fucked or trained to fuck. I said yes.

We get on the floor of a warehouse. And there are several booths open to everyone to see. The men teaching how to suck a cock or bent over and being fucked doggy style. My last one i saw the sissy was asked if he wanted the cum inside his ass he moaned yes. Val asked me if I want to try it. I nervously said yes.

Val leads me to a booth. The handsome six pack guy named tony looks at me and says wow you look hot. He turns me around looking at my figure and assets. His hand grabs my buttocks. Say oh wow a nice bubble and firm. He tells me to get on my knees. I pulls out a 7 1/2 inch cock. He instructs me how to handle it. Then he slowly pushes it my mouth. It taste salty. He goes deeper and i gag. My eyes water up. He pulls back and continues to pump it into my mouth. He stops. Get up sissy.

Leads me over to a bench places me on it with my ass sticking out. He sees my thong and pulls it over to the side. I am nervous. Of course , it was going to be the first thing to penetrate my butthole. It was only for exit only. And now a cock will enter my body to be used to excrete a mans semen inside of my body.

You ready sissy fag. I said yes daddy. He smiled. I felt the head at the entrance of my butthole. He slipped it in slowly. And it hurt a lot. He left it in place. The pain subsided. Wow it feels great. He pumps my butt unti he he cums. I had a crowd by the door of my booth. He asked me if i want his cum inside of me . And in my feminine squeaky voice said yes daddy. He pumped his load into my ass. The first one. I was already addicted to it.

I packed my stuff and headed home. I was elated. I found something I like to do. I stopped at a rest stop. And went into the woman restroom. I had to pee. But refused to push out the cum in my ass.

I sat at a bench. I pulled out a cigarette. I really did not smoke. But conversation can be made. As I was about to light up a young scraggly guy walks up and lights my cigarette. He says his name is ken. In my feminine voice I say my name is Briana. We talk for a while. He says he travels up and down the freeways looking for sex. Wow come right out and say it.

He is checking me out. So Ken where do you go to do the deed. He grabs my hand and we walk out aways from the restrooms. There is a dirt path that leads to a park bench. He grabs my face and starts kissing me. His hands are rubbing all over my body. I feel him cup my butt.

He tells me to turn away from him on my knees on the bench. I says when I saw you get out of your car i got instantly horny. I have not had sex in several weeks. I can tell he was high on something. But hey another cock in my butt. He pulls up my skirt. Revealing my thong between my crack. You have a ni…. You are a guy. He saw my nut sack. You need a hole honey or not. He leans in and kisses me again. Pulls the thong away from my crack. He spits on his dick and pushes his 7 inch dick into my ass. Aaaaaaahhhhhhhhhh as reaches the end. His whole cock is enveloped by my boi pussy. He starts to fuck fast. He is sweating. I squeezed my butt muscles and he slams hard up against my ass. His cock pulsating a huge load into my butt. He lasted 5 minutes. I am still addicted to cock.

I get home and put my dirty clothes into the washer. And proceed to take a shower and push out the cum. I had a great day. The next day was Saturday. I was browsing the porn sites. Now I know how they feel. I see craigslist. Looking for sex section. I browse. But nothing turns me on. I decided to dress up and take pictures. Very provocative they were. Mostly my cute bubble butt.

Then back to shemale sites. The one thing i saw on a few were tanlines made by a thong. So i found a place who used bronzers. They were a gay establishment. So I made an appointment. They give you a thong to use through the process. I stepped into the chamber. The spray started. When finished I had to wait for 15 minutes. When I got out. Wow I had a sexy thong tan line.

Monday night I was getting horny Tuesday was going to be another day off. So I played around with the makeup. I wanted my eyelids to have a smoky look like the women of the 80’s. I put black and green. Wow my eyes really stood out. Put on the base and ruse lip stick made my lips plump. Shaped my eyebrows a little. I was ready. I put on my tight leather shorts on. I had a pink thong on. Put some falsy pads under my b cup bra. And shirt that had a little midriff showing. I really look like a ho. A damn good looking one. Took a picture.

I went to craigslist and placed an ad. Sissy boy 18 yo looking for a top to fuck my bubble butt. I put the new photo on and couple of others. Send info. I can host or travel out. It was about 630 pm. I was ready why wait. 730 a reply comes in. Wow nice assets. Can I fuck your ass at my place. Here is my address: 74565 mountain drive. Walk in go to bedroom i will be waiting for you. I reply back on my way should be 10 minutes. Cant wait!!

I drive over it is a quiet street with two houses. I see the door is ajar. I open it slowly and walk in. I walk to the back and turn to see the guy lying in bed. He gets up and walks over to me. He looks me in the eye. You look beautiful babe. I say thanks. You can call me daddy. Ok daddy. He pulls out his 7 1/2 inch dick. I grab it as i lower myself as i was thought.

I start to lick it looking up at him as he looks down on me. I open my mouth and wrap my lips around it going down on it gagging a little looking up still. He says suck it faggot. I get excited. I grab his balls and lick them too. He pumps into my mouth a little. I taste a salty precum in my mouth. I am engaged in his dick for 5 minutes. Then he pulls away. He planned the whole event.

He pulls off all of my sexy clothes.He tells me to position myself on the side of the bed. Lying on my stomach on bed but standing arching my butt for him. We kiss some more. I realize there is a mirror facing me. I will see him fuck me. He goes down behind me. And eats my butt out plunging his tounge deep up my butt.

He gets up and says he wants to strap my ankles to a device i will be standing on. That is weird. He says it will give me more leverage. There are straps on the bed too. He says he will strap my arms to them. Basically keeping me in position unable to move. I was getting worried. Is this guy a serial killer. Oh shit I hope not. He undresses goes over to a dresser drawer pulls out a small bottle and some type of strap like a tie.

He scootches up to my butt. His Eight inch dick throbbing at the base of the entrance to my butthole. He slowly pushes into my hole. A little pain. He says sniff on this. In my mind oh shit he will knock me unconscious and rape and murder me leaving my body on the street.

He says its poopers. Will make my ass relax. I take two hits. Wow!! What a sensation. He slowly plunges into my gaping butt. Receiving every inch. He starts to pump my ass. In and out in and out. I feel every curve and vein. I watch him in the mirror. You like my cock babe. I said yes daddy. We keep up a good pace. He yells at me damn it keep arching your fucking ass into me. I get a little scared. He has a funny face as he drives his dick harder and faster into my butt.

What did I say you fucking faggot arch that fucking ass or I will show you how. I arch harder as I look at him in the mirror. He slaps my ass hard. He grabs my hips for better driving leverage. FUCK IT YOU ARE NOT DOING IT. He grabs the tie and proceeds to wrap around my neck. Strangling me as i see him in the mirror doing it. In my mind i am scared. He pulls hard back and my whole body arched into each thrust. I see my life slipping away as I look at him thrusting into me. He would lighten up the pull back hard. Oh you fucking faggot i want to cum into your ass so bad. Do it daddy. Thats what I want to hear babe. He drives it harder. I see my smoky eyes roll into the back of my head. He better cum soon or I will pass out. Then he slams hard up against my butt pulling my neck back with the tie. I feel his cock throbbing and pulsates a huge load into my ass. Aaaaaaahhhhhhhh damn that is a fucking nice pussy. He finally releases the tie. I an sweaty. I feel sweat on my backside on my back dimples. He pulls out and his load leaks out. We both collapse and fall a sleep. I will wake up in the morning next to him. What is next?