My name is Dillon and I had a normal teenage life till now. It was going good. Puberty was being kind. I was filling in the right spots and no downsides like a pizza face. I was the star of the school swim team and the girls liked the look of speedos on me. Plus in a few years, a driver's permit and my first back seat pussy. Also add that my older sister Susan had just moved out to start college. Then came that day.

I was out back, bored. I found my old baseball bat and some rocks. I would toss a rock up and hit it. Not watching, one of the bigger rocks I sent air born smashed right thru my sister's old bedroom window. My sister lived on campus but my folks kept her room as she left it, for when she came home for visits. I dropped the bat and ran inside to see how much damage there was.

I was dead. Really dead.

The rock not only broke my sister's window but sailed across the room smashed the ceramic doll that had been for years passed down from mother to daughter in my family and whacked a hole into the wall. I kissed my life good bye as I heard my sister's car pull into the drive way.

Susan came in with her dorm mate Traci. I learned that mom and dad had to go out of town and she would be watching me. The whole town could hear her yelling after seeing her room. When she finished, she picked up the phone to call our folks. Another nail in my coffin. Who would be more angry mom or dad with me for being dragged home because of my mess.

Then something strange happened. Traci stopped Susan and had her hang up the phone. Then came a talk about how the damage could be fixed up good as new and no one would know. Susan pointed out the key problem, where was the money to do this come from. Traci asked if Susan knew where she got the money for college. She did not know. Traci went to our family computer. The folks kept it out so they could see if we went to any wrong sites. Traci quickly turned off the parental controls and loaded up a web site.

The site Girl Master was like nothing I had seen. My wet dreams and jerk offs had been to girls in bikinis and the girls' underwear section of catalogs. Now I saw all kinds of adult themed women. The site models showed anything for a women to wear or use for sex. Traci was making a fortune selling sex to women, but was missing an item. The women's site needed a token man or in my case a token boy.

I refused and acted out, but the threat of calling the folks broke my will. They said I went around in speedos, so this would not be anymore of a big deal and they would put a black bar across my eyes to hide who I was. So started my sex job.

Before starting the web shoot, I had to be made ready. Except for my hair and eyebrows, all my body hair was waxed off. I was told I was playing a girl's boy not a man and I shaved anyway for swimming. Then I was oiled up to look good. Even with it being my sister and her friend I got hard, but Traci said it would look good for the pictures.

The first ones were me as a baby. This got other guys off? I had a bonnet on my head. I was sucking a pacifier and holding a teddy bear. I was in a fuzzy one piece unzipped to show I was wearing a diaper. The diaper was not all fastened and the side of dick showed along with one of my balls.

The next shoot had me in leather. I was down on all fours in a leather jock strap. A thing called a ball gag was in my mouth. A spiked dog collar was around my neck. To add to the so called fun I was also in a dog cage.

Traci put up the pictures on her site as an advertisement. Girl Master! For the needs of women who have a good little sissy (me as a baby) or a bad little faggot (me in the dog cage) or anything else. I asked and hoped my job was over, but was told I had to wait to see if this brought in enough money for the damages I did.

The next day my sister forced me out of bed. Traci's web site had been offered a job for me. A women's group asked if the site's male model would strip for them and do a "private" show for one of the ladies. I could not, would not, and did not know how to do a "private" show. The girls played the damage card and I was forced to do it. They told me to cheer up and they would teach me. After digging around in my stuff they came up with my stripper's outfit. They had me put it on and then comeback.

I had on an old break away warm up suit with an old pair of speedos under it. The speedo was tight, but the girls said that it was good cause it showed my package and my ass stuck out. I just had flip flops on my feet so I could kick them off fast during my dance. To keep my secret id, an old Halloween robber's mask. How I prayed the string holding it on would not break.

The girls blinded me with a spot light and from the speakers a techno dance song roared. With the web camera going I was ordered to dance. My learning to be a stripper and stripping was recorded and uploaded to Traci's site. The girls stuffed play money in my too small speedo and groped me each time to get me ready. After learning to work my ass. I was instructed on how to do "it"

It was not to be with one them, that would be sick. To my shock, they produced a cheap blow up doll. It had a frozen face of horror on it with a large O opening for a mouth. The doll was laid down and I was told to please her first. The girls recorded as I played with the inflated breasts. Then they had me work below the waist. On the web site would be me with my tongue in a blow up doll. Still it looked better then when I pulled down my speedo and fucked the doll. The girls had me keep doing it till I looked as if it was not my first time. The last step was to build my endurance, so I would not blow the second my dick entered pussy.

For that was the pussy-tron, no better fake pussy. It had soft feel battery heated insides and fake outside hair with fine tune suction. For the camera I would work myself off and before blast off pull out and shot. I made the time longer with each practice. The girls said I was now ready for my "private" show.

My dance was held at some motel. I don't know which one. I was kept down in the back seat of Traci's car and snuck into the room so the manger would not know about it. Traci gave me some pills to take before my show. They seemed to have strange effects. I felt more at ease but my dick and myself got more turned on. I worked my money maker even with the women looking as old as my mom. They put money in my speedo and used the time to feel and stroke my hard dick and balls. My face has never been pinch as much as my ass was. I shared drinks with the ladies as I did lap dances and posed for pictures. When the time came Traci took my speedo and the money in it. She helped my nude but hard body into the next room and left me.

Boy was I out of it. In my haze the woman looked like my mom. She sat nude on the edge of the bed with her legs wide apart. She talked about how this was her first time with a person who did it for money. How I was so young, I could be her son. It would be hot so she would play as if it was her son under the mask. I did not hear but heard my mom calling me. I stumbled and fell. I saw and crawled to her open pussy.

I was trained well as my tongue teased her furry friend. She grabbed the hair on the back of my head and tried to shove my whole head up inside her.

"Oh Yes!"

"Get in deeper Dillon!"

"No ones ever done this before!"

"Good boy Dillon!"

I did not hear what she said I was to busy with my first real pussy. It was an older one but tasted and smelled nothing like my plastic partner's did. She stopped me and told me it was time to fuck. The lady lay down as I mounted her. Again an older pussy but way better then a plastic one. I pounded her and the bed springs. Funny I kept thinking I was looking at my mom the whole time. Then after the work out small parts of me return to the pussy I came from.

Finished the lady and all the other ladies left. I was left alone nude, still hard, and in the robber mask. Traci returned and helped me home after gathering everything up and the hidden spy web cameras. She said tonight would be gold. Good cause I had my first real fuck.

I can not say when because I was still out of it from the other night, but my sister woke me up. She had me come down stairs in pjs, a robe, and slippers. Down stairs another web shoot had been set up. My sister worked the camera and Traci was going to work me. Traci was dressed as a guy?

"Well sport. You have been a bad little fellow."

"Um? Sorry?"

"Sorry Dad!"

"I'm sorry dad?"

"Not good enough. Off with your robe and bend over the table."

Confused, I took off my robe and bent over the table. Before I could react, Traci bound my legs and arms under the table with an item on sale at her web site. I was trapped.

"Sorry son. You need a good spanking."

My hearing was fine on that one but I could not break free. My bottom pjs were slowly pulled down and boxer covered rear was shown.

"No. This calls for a bare ass whipping."

Traci yanked my boxers down and gave me a taste of what was to come by slapping my backside with her hand. Some sadistic paddle was on sale at her web site and it showed how it worked flesh on my butt. Within minutes, I had a scarlet red rump and was crying a pool of tears with snot build up. Then something thick and long was slipped in my mouth like a giant plump hot dog only made of plastic. The thing went in and out of my mouth and throat. After it was slicked up.

"The black kong strap on is easy to wear and easy to get ready as one can see. It will please either type of partner."

What? What the hell, no. My mind could not react quick enough. The fake black head started its forced marched. I felt as if the biggest dump I had ever taken was going all the way back up me. The plastic dildo savaged my ass hole as if there was no tomorrow. It even got worse.

With me begging for her not to and the strap on still way up my chute, Traci undid my bindings so she could turn me on my side. I was on my side on the table with my sister zooming in with the web camera. My hard dick was sending load after load of teen sperm out of its top. Having my ass fucked was such a turn for me, I shot my load without even having to touch myself.

"As stated. Will please any partner."

"That is a wrap."

Staying on the table with a red behind and a sticky front, I sniffled and wondered how much I stilled owed?