Bottoming My Way to the Top

I was a 25 year old small town boy from Nevada with a lot of aspirations and ambitions but I was very weak in the eyes of my peers and friends. A person who wants to achieve anything needs to have certain set of qualities or talent. I had none of those. I was an average looking boy with a height of 5'8", not chubby but a lot of my 160 lbs weight was in my ass. That was probably the best feature of my body. I did have long hair but they were always tied in a bun so nobody had really seen how long they were but by the thickness of my bun, one could judge that I either had them very long or the volume was good. I can tell you that I had both. So I was in love with my hair but to not make it look feminine, I always had it in a bun. I was working in a coffee shop and even there as a waiter and not a manager. Also I had limited friends and even those weren't really close, one could call me a loner. So well, the people around me were right to judge that I didn't have any potential to be someone exceptional in any sense. Having said that, I can tell you that life isn't always fair and everyone has a different destiny.

About my sexuality, I always thought I was asexual. I never had any desires like my school friends to have a peek at a woman's panty or her cleavage. I did find myself attracted to beautiful girls. I admired them a lot and I loved how make up and good hair day could make a not so attractive woman, very attractive to me. So I was fascinated by make-up and having beautiful hair myself. At a very young age, I had decided to never cut my hair and they had grown till my back. I had trimmed them myself watching videos on the internet because I liked having them pretty and still didn't want anyone to notice. I had never had any attraction towards the boys nor was I overly focused on masturbating while watching a girl hence the thought of being an asexual. The only time I would masturbate would be thinking about others playing with my hair and even that was very rare.

One nice evening, while serving at a coffee shop, I had a customer who was constantly ordering coffee for a long time. He was a well built man in his late 30s and must be 6'2" and around 200 lbs with pure muscles. I could see him staring at me whenever I would turn back. I found it very odd and even though I wasn't really of rebellious nature I still decided to confront him about it. He smirked a bit when I asked him why he was staring at me. He was so confident in the way he replied. He said he was a model hunter and had a very special kind of business and with that big ass and long hair I would definitely fit his requirements. He asked me to meet him after my shift ended and I agreed to do it.

So later that night, he met me in the parking lot of our coffee shop and asked me if he could take me out to dinner where we could discuss the business privately. I agreed to it. He had a nice car that someone with a good taste and a very good income could afford. While driving, we had a normal conversation. He asked a few questions about me which made him sure that I was a loner and a below average worker who wanted a better life. After reaching a good restaurant, for which I was definitely not dressed properly, we sat at a corner table. After ordering us wine and some good food, we started our conversation about the business. He said his name was James and whatever he was going to tell me about his work was very confidential. James asked me about my monthly salary. I told him it was around USD 2500 per month including tips. He said he would pay me an initial amount of 10k for joining his business but I would need to provide certain things as security if I ever disobeyed our confidentiality pact. I said I lived in a rented apartment and didn't own anything substantial to be put for security.

He said he didn't need money but instead something that could be used against me if I ever cheat on him. He explained that he may need to click a few pictures or a video of me.

I was in two minds. There was an aspect to turn my life around for good or it may be that I would lose everything and my current job. He wasn't even telling me about the job but I could figure that he would be trying to make a model or something for a porn magazine probably. I wondered if he would take naked pictures of me, would it really do any harm to my life, as I really didn't have anyone to hide myself from. It would probably make me a bit famous. I thought about it and the money was a huge factor in my decision. So I said a yes. I was then taken to a gay bar where he introduced me to a friend who was himself a crossdresser. He introduced himself as Kandy and even though he was dressed superbly with great make up, one could tell that he wasn't really good looking. He was really sweet as he offered to do my makeup in the back room and said that I was probably the best replacement James could have had. I asked him what he meant by replacement. He said I would understand everything and to be patient. This was once in a life time opportunity according to him. I was so excited now.

I changed myself in a dress that made me look very feminine. I was given black panties and with that skin tight leather jeans with very low waist. My top was a backless top and I had to wear a thick gold chain with it. I had no bra and flat chest and one could definitely tell that I wasn't a girl. Kandy started working on my face and applied a few things: foundation, blusher, ruby red lipstick, black eyeliner and mascara with a silver eye shadow. Then he started working on my hair and after brushing and styling it for a few minutes, he asked me to go in front of the mirror. OMG! The change was amazing. I was completely transformed into a beautiful trap. The only thing that would give it away was my chest and the now protruding penis. I was hard looking at myself. My hair was left open and styled beautifully. I was so happy with my decision to go ahead just by looking at my hair.

James knocked and entered the room and was left agape after looking at me. He couldn't believe it himself. I could see the lust in his eyes and an erection growing in his pants. I couldn't blame him for it, even I wanted to fuck myself. For the first time in my life, I felt desirable and the feeling was amazing. He said and I quote, "You look so beautiful that I would marry you in a second" and that didn't go down so well with Kandy as he left the room without saying anything. Were they more than just friends or ex-lovers? Hell who cared, I was beautiful and it was my day but now I had a task to fulfill. We went inside the club. James ordered me a drink and I could see a lot of the gay men staring at me. A few even complemented me for my looks. James wanted me to dance with him and I couldn't say no. We were dancing on a song with my back pressing his stomach and I could feel him press his bulge. It was all so natural to be submissive to this man. I was dancing like a girl now and James was leading me. After a few minutes, he turned me around and now we were facing each other and he kissed me and that was the first kiss of my life and I felt wonderful. We kissed for a long time and even tongues were involved. We were now rubbing our dicks through our pants and it was a sensation very new for me and if James wasn't holding me, I couldn't have stayed on my feet.

After a few mins, he took me to a table. He said he had no clue that I was gay and It would be so much easier for him. He thought he would have to convince me to do such things and he was proud of his vision to pick boys like me. I replied that it was my first time being with a man and even I hadn't thought about being gay but it all seemed very natural to me. Probably Kandy's work made me want to do everything that I did tonight. James meanwhile, had a plan. He pointed towards a middle aged man who had his back towards us. He explained that he wanted to test if I looked beautiful to others or was it just him. Also he needed me to play a bit with this man and let him explore my body a bit. Doing this with a stranger would test my boldness to do any job. If I pass this test, the 10k and a very well paying job was mine.

I was a bit nervous but didn't want to show this to James, so I got up and went to the table where this man was sat. He was probably in his 40s, had good physique and looked tough. I introduced myself as Tanya and he was John. I don't know why but that name just came to my mind. He obviously knew that I wasn't a real girl. I sat with him having asked if he was expecting company to which he said he wasn't. He ordered a drink for me and we soon started talking about bit about ourselves. He told me that he was a businessman and was on a tour across Nevada. He was originally from Reno. He had a couple of kids and a wife back home and this was his first time in a gay club. I told him not to worry and this club was very friendly for the newcomers and with that I put my hand on his thigh. I had no clue about the club or what was I doing with this man but it just felt natural. He took notice of my hand and got himself close to me and soon we were kissing. I was kissing a stranger and it all felt natural to me. I could feel him getting hard in his pants and he moved my hand on his crotch. It felt big and I started rubbing my hand over his dick. He was totally getting into this and he started kissing my neck because of which I started moaning.

Even though the music in the club was loud, but people could still hear me. John then asked me to come with him to the toilet. I was nervous as hell but I only wanted to portray a confident image. We went inside and it was empty. He dragged me in the corner cubicle and took me inside. He took no time in removing his pants and he wasn't wearing any underwear. He kissed me again as his hard-on started poking me in the stomach. I took hold of it, for a sec I thought it was to adjust it but it struck me that I had another role to perform right now. I started stroking him and soon I felt him kneading my ass cheeks. I was moaning continuously with his assault on my lips and neck and now my ass. He asked me to get down on my knees as he was very close to cuming. He said it was his fantasy to paint a pretty face like mine. I didn't want to disappoint this man and I went down on my knees and made a puppy face while looking at him. This probably sent him to the edge and he blasted a huge shot on my face and followed by a couple of other ones.

I started searching for the toilet paper with whatever vision I had left. But I realized that there was no toilet paper and so I removed the cum with my hand as much as I can. John meanwhile had dressed back and left a 20 dollar bill on the toilet seat. He thought, I was a whore and I realized a lot of other men in the bar must be thinking the same once I get out. I was scared as hell. I took the money and got outside the stall. James was there and he clicked a picture of me. I didn't care. I just wanted to clean myself up and get the fuck out of this place. After cleaning myself, I saw that James wasn't there. So I went outside and found a couple of men asking me for a blowjob or to take me home to which I denied and went outside the club. I could see James waving towards me and I went to his car. As I sat inside, there was someone else in the car and it was John. I was shocked to know that he knew James. James then introduced him as Police Officer John Carpenter. I thought what had I done.

My life went upside down in that very second and It felt like I was going to pee myself. But James calm me down by shaking the 10000 dollars that he had in a 100 dollar bills. So the Police was okay with this. That made me calm and I started listening to what James had to say. He told me that he and John were brothers and John is the one that protects him and his business if they get in trouble. He explained that what I did today with John was going to be what they would do. The only difference being instead of using the video (he had the video of me stroking John) against me, it would be to blackmail "innocent bi curious middle aged men" who I would seduce. He said that he was a con artist and he had been doing this for last couple of years with Kandy. He had moved on from Kandy because she had grown quite old to be so seductive and a few people may recognize her now. He said I couldn't imagine the amount a bi-curious straight guy would be ready to pay to save his image and whatever I would earn with James would be divided in 40-40-10-10 ratio with "Tanya-James-John-Miscellaneous Sources" respectively.

He then asked me if I was in or out and said if I said in, I won't be able to get out at least for a year. I had no clue what to say but being assured about a help from Police made me say a yes then. He followed with explaining how he did his business.

He would select a city and he would go to a bar which is frequented by gay men there. He would note down a lot of information about the target man which would be suggested by his source. This man would ideally be an above average or modestly rich married man who would earn 30k a month. Once James had enough information about this man, he would ask me to seduce this man in the bar and enjoy a couple of nights with him. I would only introduce myself as a traveller and not a whore. I would have to enjoy his company and know a lot of his personal details. Meanwhile James would record almost everything we do together and then after a week of doing the same, he would start blackmailing the rich man. He would ask the man to dump the money at a place where no one could see them in exchange of the pictures and videos. Once they get the money, they will move on to another city. He explained that there would be no changes in the rules. One city could only have one man. Although it was a stupid thing to say, but he told me that I could not get attached to any man who would fuck me. In the end, he estimated a personal income of 200k in one year. Till that point, I was scared but now I was scared and excited...

Can an ordinary boy, turn into a successful rich con artist...

(To be continued).