For a while I worked as a transsexual street prost
When I first moved to Sydney in my mid 20’s I had trouble meeting the bills. This was desperate times so after a lot of soul searching I decided that the only thing I could do was to become a prostitute.
I knew Sydney that the transsexual prostitutes picked up clients on William Street near Kings Cross. Not really experienced on the ways of the street I drove down that night and went for a walk along the road fully dressed in all my slutiest outfit. Short black mini, Stiletto heals and tight leopard patterned top. In those days I still only weighed just over 50kg and since I am only 5.3” I looked like a small regular girl. I saw another group of working Tgirls and went up and started to talk to them. I told them that I wasn’t really sure about how to approach this and I wanted to make certain that I wasn’t going to encroach on any body’s territory or have some pimp come and beat me up for not working for him. They where really nice and took me under their care and gave me some great advice about safety, the cops etc. Since I was a newbie as well they told me about what spots it would be O.K to work from.
So began my life as a street prostitute.
I didn’t have a spot on the main road but on a small lane way called Premier Lane just behind the main street. It was a well known cruising spot for guys local for transsexual prostitutes. I rapidly started to see patterns emerging with some guys walking by me couple of times in a short period checking me out. I saw a small car coming up the lane and parked. No body got out after a while and I kept my eye on it. After a minute or so I could see it slightly rocking. I was pretty sure the guy masturbating while watching me. I decided to give him a little show and “accidentally” dropped my lipstick. I bent over so he could have a good view of my ass while I picked my lipstick (very slowly). After making sure he gotten a good view of my ass I walked towards the car and lent into the open car window. I could see a young guy in his late teens behind the wheel and he had pulled his shirt out and was trying to hide his raging hard on.
“Hi sweetie need a hand with that ?” I said
He seemed to be embarrassed that I had caught him and mumbled something. Then asked me “how much?”
I told him “$50 oral, $75 for anal and $100 for both” He said he would like to fuck me so I asked him if he would like to go some short time rooms. He said he only had enough for a fuck and couldn’t afford a room. So it was going to be sleazy fuck in public. There was a small dark door way set back from the lane just near the car so headed over and told me to join me. He gave me the money so I put a condom on him turned around against the door lowered my panties down and stuck my ass out for him. He pushed into me and started to pound away. Since I had been an actor growing up I made all the right noises and talked dirty and how good it was etc. He either was so excited or wanted to get away fast that he blew after only about 2 minutes. He couldn’t get away fast enough took off the condom and jumped into his car and drove off. Damn that was easy!
I took on a couple of more guys that night and made enough for my rent and headed back home around dawn.
After that I went back to work on the street most nights. I was making good money and got my self a few regulars that would come and see me.I honestly don’t remember most of them as when you’re having sex with 5 or more different men a night they all became just a blur.
With one exception.
Since I was so small I took on the persona of a naughty school girl. I went to a few second hand clothes shops and picked up some very short dresses in the colours of the local schools (In Australia each government school has its own uniform.). I would put my hair in pig tails sucking and licking on a lollipop leaning against a window sill looking all sweet and innocent.
I had raised myself in the pecking order amongst the other girls working on the street and had gotten myself a spot on William St where I could be seen more easily. One night I was approached by a guy in his 60’s or so. He only about 5.5” bald and a big belly. He asked me about the uniform and where I had got it. I told him that it was from a 2nd hand shop and he told me that he had recognized the colours as he had worked as the vice principal at that school before he retired. We went on talking and he said although he had fantasies about some of the students he had never acted on them. This was going to be a “specialty” trick so I negotiated a good price and agreed to go back to his place.
After a short tax ride we arrived at a block of old government flats. As he opened the door of his flat he told me that I should “Get into my office” It was an old dingy single room flat. He walked in behind me and said ‘Now explain yourself young lady, why where you in Kings Cross late at night?”
I said “I’m so sorry sir I had lost my train ticket and needed money to get home”
He looked at me sternly and “Rubbish, I’ve heard rumors about you at the school. One of the teachers heard that you had been sneaking into the boys toilets and sucking there cocks. You are such a good student and I didn’t want to believe it but now I know it’s true.”
I looked at him and started to cry “I’m so sorry sir I try to be good but I just get these feelings. I can’t help it”
He smiled and said “Well you going to need to be punished for your actions. I can either ring your parents you can take your punishment from me.”
Still crying I blubbered “Oh no please don’t tell them. I’ll do anything you want just don’t tell my mum and dad”.
“Alright go over to the table and assume the position”
I walked over to the table and lent over the table with my arms resting on it and with my dress riding up showing my white cotton panties. I heard him rustling threw a draw and taking something out. I glanced behind me and saw that he had gotten out a wooden cane about 2 feet long. He got behind me and slightly to one side and said “Right now you’re going to pay for being a dirty little girl”
I braced myself for what was about to happen. He wasn’t gentle and gave my ass a good hard hit with the cane. I gave a for real yelp from the pain. Damn I was really going to earn my money this time!
“Quiet or the neighbors will hear you.” and proceeded to give me six of the best across my ass. Stepping back he then pulled me up and told to “suck me like you like you do in the boy’s toilets.” At some stage he pulled out his cock. It wasn’t that big only about 5” but very very thick and uncut. I knelt down in front of him and started licking and sticking my tongue inside his foreskin. I opened my jaw wide and moved my mouth all the down his cock my tongue working on it as I swallowed it all.
“Jesus Christ” he moaned “now I know why the boys like you so much”
I kept working on his cock for about 5 minutes giving him my best value for money. Pulling me up he told me to go and bend back over the table. Putting a condom on him and lubing it generously I went back and assumed the position. He came up behind me and pulled my panties down and slipped them off over my ankles. I spread my legs apart ready to take his thick little cock. He grabbed my around my waist and pulled me back on to his cock while pushing hard into me. I gave another yelp as it pushed my ass wide apart. He pulled back and drove back into me again and again. He eventually locked himself into me. Putting his full weight on me he put his arms threw mine and started to grunt and lick my face and neck each time he’s cock stroked inside me. This was just a pure and total a****l fuck. He kept pounding me and pounding me and I thought he would never stop!
Finally he said. “Time for you to drink your daily milk” and pulled out of me. Roughly pulling me off the table he pushed me back down back in front of him.
He pulled his condom off and I saw that he shot his load while fucking me. He told me to open my mouth and poured most the contents into my mouth then wiped the remainder over my face.
“You’re a nasty little school girl whore aren’t you. You can go now and but don’t mention this to anyone or I’ll make sure your parents find out that you are working the streets for money”. I left the place with a very sore bottom and went home for the rest of the night.
I continued to work on the streets for about 8 months before I got a regular day job.I continued to go and work the streets very so often when I needed a few extra dollars I would go and do a few tricks. After a few years and a lot of extra Kilo’s I couldn’t get into my school girl clothes and the other girls working the street where a lot prettier than me so I retired gracefully
For me now it’s just sex for pure pleasure.
Posted by toniparr 3 years ago Views: