Pizza Boy Sissy Pt. 01

A fantasy fiction.

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My name was Sam and I was a 18 year old pizza delivery driver. I just finished high school graduating early and started the summer working for Papa Pizzas. I had never really been a ladies man due to my non masculine body and long girl like hair. I was also really nervous to try to get with woman because I had a small penis. Because of all of these circumstances over the years I got addicted to watching shemale porn.

There was something that got me off about a sissy than a woman could. I never thought I would want to be a sissy, I just liked to watch it. We'll that was all about to change.

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It was just like any other day at Papa Pizzas and I was really bored waiting to take a delivery. When it finally came out of the oven I quickly headed out to my car to deliver the pizza. I really enjoyed delivery jobs because I could drive around and smoke and take my time. This delivery was headed to downtown. When I arrived at the home I got out and went and knocked.

All I heard was a man yell come in so I opened the front door and stepped in. The man was waiting for me with the money and a smile. As we were about to wrap up the conversation and head out I noticed at the end of his hallway a TV with a video of a shemale being railed by a huge cock. I kind of stared at it for a second which is why the man noticed I saw it. He seemed to be really embarrassed and apologized if I felt uncomfortable.

I don't know what got into me but for some reason I told him I like the same kind of porn. The man was pretty surprised and I could tell he was not as embarrassed. As I tried to leave the home the man told me to come on by tonight if I wanted to earn a huge tip. He introduced himself to me as Kevin and shook my hand. Tips are what paid my bills and allowed me to buy more bud. I wasn't gay or a sissy but I really thought it might be worth to do what he wants for the money. I told him I would be back around 9 pm that night.

I was so nervous finishing my shift that night. I didn't know if I was going to go through with going to his house but by 8:50 I was in front of his home. I really was strapped for cash and thought doing what he wanted might be worth it. So I decided let's get this started and went and knocked on Kevin's door. He opened the door instantly.

Kevin had to have been a solid 6''3" while I was only 5'8". He was a bigger man probably about 220 pounds and pretty muscular. He welcomed me in and handed me a drink. He said it was captain and coke, my favorite, so I gladly started to sip on it. We walked down the hall way where the TV was into a room. It had a bed and a coach and there was a lot of lube bottles and napkins laying around. He told me next time I come over he would clean a lot better.

We both sat down on his coach in front of the TV. He asked me what I wanted to watch and pulled out a DVD case filled with tons of shemale porn. I rummaged through them for a minute until I found one called "Big Cocks and Sluts 4". I gave it to him and he put it in. We watched the DVD for about 5 minutes and he started to unbuckle his pants. He told me that he was gonna have some fun and I was welcome to join. His cock was about 10 inches and about 3 inches thick. He squirted a bunch of lube on his already hard cock and started to stroke. I thought about master bating to the video but for some reason I could not hard. It might of been because my new friend Kevin was jacking off hard next to me. I started to focus on the cocks on the TV until I started to watch Kevin master bate. Kevin was really into watching the TV until he noticed me glancing at his cock. We both mad eye contact and couldn't look away from each other.

I don't know what got into me but I got off the coach on my knees in front of him and started to lick his cock. I was staring up into his eyes slowly running my tongue up and down his cock and around the tip. I started to taste some his precum mixed with lube but it made me feel more lustful. I then started to suck on his cock, slowly shoving inch by inch into my mouth. I had never done this before so it took me a while to breathing through my nose. The whole time I did not lose eye contact until he pulled his cock out of my mouth hole. He pulled it out and jizz started to shoot all over my face and hair. I could not keep my mouth shut so I started to swallow it. I licked his dick clean and sat back out the coach out of breathe covered in jizz. Kevin looked at me and told me that was amazing and threw a crisp $100 bill at me. He told me he was going to bed and come by tomorrow anytime.