Bottoming My Way to the Top Ch. 02

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The beautiful boy indulges in his first criminal activity.
2.6k words
4.38
13.2k
5

Part 2 of the 2 part series

Updated 06/08/2023
Created 01/06/2018
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gtanya
gtanya
132 Followers

For our first adventure, James chose a safer destination in Las Vegas, Nevada. He explained that most of the tourists in the city came here for about 3-4 days and hence there was no chance of getting caught by someone as we would already be gone once I had played with my man. We would find an easy target here coz people came to this city to be adventurous.

Since meeting Kandy about a couple of weeks ago, I had been practicing at home with the make-up kit that was provided by James and the few hairstyles that I could learn from Youtube. I was getting good day by day but still was far away from what Kandy had made me that day. I was so involved in being Tanya that I had completely forgotten about Terry (I had failed to mention my name in the first story). The only time I didn't have my make up on was when I was grocery shopping. I had already quit my job as I needed to concentrate on being feminine. On probably the 10th day, I had gained courage to go out completely dressed as a girl. I went in the night to a new shop for grocery, paid the bill and nobody really behaved differently with me. That was a bit reassuring. Being Tanya was fun and exciting and I masturbated a lot in the 2 weeks, always thinking about how I had kissed a man as a girl, took his cum on my face like a girl and how I was going to be the seductress. I was still a boy but dressing feminine made me feel so lively. I had been continuously thinking about learning what styles would excite the men more and would make me look hot.

James had not really been in touch in these past 2 weeks and had informed me that we would be leaving for Las Vegas exactly after 2 weeks from the day we had met. He called me on the 13th day to inform that he would be picking me up in a caravan and I was told to bring my make up kit along with a few panties and bra that James had bought me. According to James, I would be having a full wardrobe in the caravan and I would always be dressed feminine. He picked me up from my house and the caravan was huge. He said, he owned it and had been using it with Kandy for the past 2 years. I took a tour of the caravan as we started moving. It had a small bed along with a sofa for 2 to sleep. Also there was a toilet, a small kitchen and a couple of wardrobes. I believed one was mine and other for James. I asked James permission to open it and James replied that I shouldn't be that formal and to go ahead. The wardrobe was amazing. It had 6 shelves and out of the 6, 4 had drawers. The top shelf was It had so many dresses, a lot of drawers with panties, lingerie.

The top shelf had a couple of wigs with a blond and a red head wig both placed on mannequin's heads. The second most shelf from the top had 3 piles of clothes, dresses, skirts + tops and gowns. The third shelf had 2 drawers, one filled with artificial jewellery all placed in boxes and the second one had accessories with watches, sun glasses, lockets and a few other things. Fourth Shelf had a single drawer and it had all types for bras, panties, lingerie and stockings. I could see the tags on them and they were all new. James had invested a lot in this. Fifth shelf had a drawer filled with sex toys. Butt plugs, dildos, vibrators, strap-ons (why was it needed, I thought), chastity devices and a few more kinky toys. The last one was the biggest shelf with atleast 10 pair of heels and footwears. This was probably heaven for a girl in making. I wanted to take out everything and try them on but James called me. I didn't realize that I had spent half an hour looking at the wardrobe and we had stopped for lunch.

After picking up our lunch from McD's we left and this time, I sat next to James. He started explaining the plan that his friend in a club has found a couple of men who fit our description and they have been here just for a day. They have just been looking and have been afraid enough to approach anyone. Tonight I would have to use my charms to get into his pants and be his girly-boyfriend for the next 2 days. I was listening carefully when he explained how I was supposed to take him to my room where James would have set up hidden cameras for both pics and videos. He would be in the van outside the motel and if there is any emergency, he would intervene. I was nervous as hell.

At around 4 pm, we reached the motel which was walking distance from the club where we were supposed to hunt. I then started doing my job, shaved myself completely clean from face below, put body lotion, wore my bra and panties and started doing my make up. I chose to look classy more than slutty. I wanted this man to feel that he was going to have a real life experience and not with some paid whore.

My make up was subtle. I used foundation, blush and a bit of concealer. I chose a light pink shade of lipstick and a similar shade of nail polish and black eyeliner to go with it. I then wore a black dress to go with it, put my hair in a very high and tight ponytail. I think I looked good but waited for James to tell me otherwise. He came in the room to check on me and was stunned. He said I look gorgeous and the only thing that was needed was a pair of black heels and my beautiful smile to go along.

After completing my attire, we left for the club and we were there by 8 pm. We met the bartender who introduced himself as Matt. He showed me a couple of pictures on his phone of the men who were supposed to be my target and forwarded the pics to my cell phone. He explained to James that they had tipped him quite well the other night and looked quite rich. Both the men were alone but had a ring on their finger and were looking out of place, so it was probably their first night in a LGBT club. With this information, James gave him around USD 2k and said the rest would be delivered if our plan was successful. He then went inside through the back door and I stepped in the club through the front door. For this first time, James was going to be in the club to give me a bit of confidence and to notice what mistakes I would make.

I took a table at around 8 pm and the club seemed to be pretty crowded by then. It wasn't a big one so I believe, they had around 10 tables and a small dance floor to go along. I was sitting in the corner table sipping on a drink which I had collected from the bar. There was a problem then, a lot of men had started asking me for a drink and dance and I had to say no to all of them. I could see one of my targets looking at this and was probably feeling that I was going to reject him as well. But he did approach me. He was named as Harry and he was around 5'9",that would be around the same height as I am with heels. He asked me if he could join me on the table and I said yes. He was confused to know that I had allowed him to sit with me when I had rejected almost 8 others. I told him that none of them wanted to sit with me, they just wanted to dance with me and probably have their way later. He was a gentleman and said, he would never do that to me. He was trying to look at me again and again but seemed a bit confused.

So I asked him if he wanted to ask something and he did. He hesitated but asked if I was a girl or a boy. I smirked and replied what would you want me to be? He replied that he had never been to a LGBT club and didn't want to offend me by asking such questions but he was very curious about it. I told him that it was okay and I was biologically a boy but you could term me as gender fluid as I felt happy as both boy role and a girl role. He seemed to be happy with my description and we continued chatting. He ordered a couple of drinks for us and we were getting along quite well. He told me that he was 35 and has never been with a boy before. He was upfront in telling me that he was looking for a one night stand with someone as beautiful as me and suggested that he would be willing to pay for it. I tried looking a bit offended by it and told him that I was not a whore but I would forgive his honest mistake and would be willing to make him have a beautiful night with me.

I told him that I had a boyfriend and he was away on a trip. We had an open relationship and he was away on a trip so I took a trip of myself to Las Vegas to have some fun. He looked happy hearing all that and started trusting me more. He told me that he had a family with a couple of young kids. He had a good white collar job and was well respected for it. He was doing this coz he couldn't come out as bisexual to his friends and family and wanted it to be a one time thing. I could see that he had a good watch and his clothes were also very nice. I thought I had hit my target and I messaged James with the picture of Harry. We then took off and I told Harry that my motel was on walking distance. We walked together and he had his arm around my shoulder. While walking he slowly moved it to my ass and looked for my approval, for which I just smiled. He continued fondling my bottom while we walked to my motel. I moved my face towards him and we kissed.

As soon as we reached my room, he was all over me. He kissed me with passion and I kissed him back. I wanted to please this man and really wanted him to have a wonderful night. I took my hand and placed it on his cock. He was hard as rock and probably as big as Officer John. I started undoing his pants and placed my hand on his jockeys. I rubbed him and got on my knees. His pants were off and soon I could feel the heat coming out of his jockeys. This man was furiously excited and moaning madly with my touch. I could feel the power I had over him in that moment. I took his jockeys off and touched his cock. It twitched in my hand and already had a drop on it. I continued stroking him slowly for a couple of minutes before putting my mouth on his cock. That made him moan very loudly. I gave him one of the best blowjobs I had ever given (That was only the second one I had given) and he came like a torrent and filled my stomach. I was told by James to make sure that I seduce him well enough after he came for the first time. "Once a man has cum, he loses his desire to do stuff which is taboo for him" taught by James.

So I cleaned his cock and as soon as I saw him getting up to leave, I forced him down in a girly manner and started strip teasing for him. I removed my dress and was only in my bra and panties. I slowly removed my bra and opened my hair. I had them on both my nipples and bent forward to kiss him as he was sitting on a sofa. I had one of my hands on his cock and could feel him getting hard again. I straddled his lap and continued making out till I could feel his dick poking my balls. I stood up and took off my panties and I was only wearing my heels now. He was very excited to see my dick. He surprised me by taking me in his mouth and held my bottom while sucking me gently. I played with his hair while he kept on sucking me till I was very close. I told him to stop and I wanted to be his first boy. I put on a condom on him with my mouth and straddled his lap again and slowly inserted him in me. He just kept still or was probably doing something, I had all my focus on riding that dick. It felt amazing to ride a dick after riding dildos for a couple of weeks. Soon he started adding to the thrusts and then held me and controlled the fuck. He made me scream and moan while moaning himself. He came again after almost 20 mins of fucking me. I had cum sometime in between. I could see his belly wet with my cum and licked it dutifully.

I then told him that I wanted him to sleep with me, so that James could have some more pictures of us. We were fast asleep in the spooning position and I woke up in the night and took pictures of his personal information from his wallet. I gave his phone to James through a small window and waited for a few minutes (He had seen him put his passcode through the camera). He did his job and I kept it back as it was before. We fucked again in the morning and this time in the doggy position. We parted ways later and left the motel that very day with James.

Now was the time for James to work his magic. He found out that Harry lived in Washington and had a top position in a big manufacturing company. James had all his necessary information now. His email account, email contacts, phone contacts. He went through his facebook account to gather information about his family.

After a week of our night, when I was back home, James had left for Washington. He kept the other process a secret from me. He didn't tell me how and what had happened after that. But a week later from that, James handed me 30k in cash. I was astonished. This was a lot of money for me. I started imagining things and having dreams about being super rich. I didn't even ask James about the money he earned. I just trusted him and thanked him for it. He said this was going to be a beautiful partnership and we should celebrate and hence we went for drinks later that night and I ended up riding James for most of it.

(to be continued...)

gtanya
gtanya
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AnonymousAnonymousabout 3 years ago
more

more please!!

AnonymousAnonymousover 3 years ago

I need more

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