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Crossroads Ch.02

A young crossdresser take things farther.

The second chapter in this crazy little tale.

I really loved my little adventure out as a woman. I liked the power I had over men. I was seriously thinking that I would like to live as a woman full time. That would be quite a commitment and one that would change my life forever.

As I said before I worked for a really liberal company and one day I got up some courage and went to my boss. I explained to her my desire to live in public as a woman. She smiled and was very understanding and said that it was my decision she and the company would support me and my job would not be in jeopardy. So the next day I went to work as a female. I started out dressing conservatively but gradually got used to wearing dresses some of which were cute and flirty.

I really started to notice the looks I was getting from guys when I went out to lunch or to run an errand. I always smiled back and enjoyed how they would look at my legs and ass or my chest before they looked me in the eye. It only added to the feeling if I was wearing some sexy lace under things. My nipples would get hard and show through.

I had been on hormones for a long time and my breasts had pretty much maxed out to the size they were going to get. Most of my bras were 36 C's. I liked the attention they brought me, but I wondered what they would be like if they were bigger. I didn't mean obnoxiously huge, but maybe a cup size. One was a little bigger then the other and that could be fixed with some implants.

Now this would be a big step. The more I thought about it the more I wanted to do it. I set up a meeting with a female plastic surgeon that was know to be friendly with CD's. At our meeting she gave me some silicone forms to wear in my bra to get a feel for how much larger I wanted to go. I took them home and over the next week or so I tried different sizes and settled on the ones I liked best. They happened to be the biggest ones. When I went back to see her she took some measurements and after looking at the forms I chose said I would come out with a 36 DD cup. She would use a little bigger implant in my right breast because it was just a little smaller then the left. She guaranteed they would look fantastic and very natural.

I had a fairly large inheritance so paying for it was not a problem. After a week of soul searching I called and made the appointment for surgery. The day came and everyone at the clinic made me feel very welcome. The nurse that was assigned to me pampered me and reassured me that I would look great. The surgery was done and I woke up slowly in the recovery room. I was eventually taken to a private room and rested. My chest was wrapped and felt like I had 50lb sack of sand on it. The doctor came in and told me everything went well. She said that my breasts now matched and might end up being a little bigger then DD. Once all the swelling goes down they we shall see.

I stayed one night then went home the next afternoon. I was taking a week off work and just relaxed around the house. I was getting used to the new weight of my chest and towards the end of the week went back to the doctor to get the dressing changed. When she removed the wraps she had me stand up and look in the mirror. I couldn't believe it. There were two very large perfectly matched breasts looking back at me. They looked perfect and very natural and they were mine. The nurses in the room marveled at how good they looked and how jealous they were of me. I put on a bra to get dressed and the 36DD I brought barely contained them. I would have to go bra shopping after the swelling went down.

After about 3 months my boobs settled down and felt like they were all me. I of course continued the HRT and felt more and more like a woman. I decided to go out on the town with my new shape. I had been working out a lot and my legs and ass were tight and sexy. I decided to wear the one essential every girl needed. A little black dress. This one was little and tight. It was cut low and showed off my new investments very well. A black lace push up bra helped display my assets. As I slipped on the matching pair of black lace thong panties I tucked my little balls up inside and wondered why I still even had these. That fact would have to be addressed soon. I wore some 4 inch heels because I wanted to show off my calves. My hair and makeup were perfect and out I went.

I went to a high class bar in a hotel. They had a bar that catered to rich locals and big spending out of towners. That is what I was looking for. A guy away from home that was looking for a one night stand. When I walked into the bar most of the men stopped and stared. As I walked toward the bar I loved the way these heels made my ass swing. My chest was swaying back and forth too. I immediately noticed a man at the bar. He was dressed in an expensive suit. He looked to be about 40 and from what I could tell he was in good shape. He hadn't stopped staring at me since I walked in. He was very sure of himself and walked right up to me. He offered to buy me a drink and suggested we get a table. I accepted and he led me to the table showing the rest of the men he had claimed his prize.

As we sat there he complimented me on how I looked. He of course kept stealing looks at my cleavage. The more he drank the more forward he became. He said he was from out of town and was here on business. I kept smiling waiting for him to make his move. He finally told me he just had to see my boobs out in the open and suggested we go up to his room. I reached and took his hand and said to lead the way. As we walked to the elevator I could tell he was drunk. Not to drunk to perform I hoped. I wondered how far I could let him go with me tonight.

We got to his room which was one of the executive suites. As soon as we were in the room he started groping my breasts through my dress and kissing me. As we made our way over to the bed I reached down to the front of his pants and found a nice size cock that was still growing. At least the alcohol hadn't affected that. I pushed him on the bed and started to do a slow striptease in front of him.

I undid my dress and let it fall. I stood there in my bra, panties and heels. He started undressing himself while he sat on the bed staring at me. He had a glazed look in his eyes and I wondered if he could perform. As I stood there I turned around and bent over slightly to give him a good view of my ass. I spanked it to show him how firm it was. When I turned around he was naked on the bed. His big cock was at full attention. I licked my lips trying to decided where I wanted it. I reached behind my back and unclasped my bra. I held the cups against myself as the clasp let loose and the straps slid off my shoulders. I hesitated just for a moment the let the bra fall from my breasts. They were out in the open in their full glory. He sat up and reached out for them. I walked closer so he could touch me. He had a little trouble focusing but managed to start playing with my tits. He squeezed and rubbed and pinched.

I let him do this for a little bit then I pulled away and walked around to the side of the bed and I turned off the light. He laid back on the bed and I joined him. He continued to give my big boobs lots of attention. He sucked on my nipples which made me very horny. I stoked his cock with my hand and felt it's length and thickness. He started squeezing my ass and I knew what I wanted to do.

I kissed him moving down his body as I did. When I reached his groin I held on to his cock as I guided it to my mouth. I heard him groan as I sucked on his shaft. I was getting him quite far down my throat. I was getting his cock very wet and since he was drunk he was lasting a long time. Finally when I thought he was wet enough I made my move. I kept his wet hard cock in my hand and I straddled him with my ass facing his head. I pulled my lace thong panties to one side and I aimed his cock at the entrance to my ass.

I hoped in the dark he might not notice where it was going, just that it was a hot tight hole. The wet head of his hard cock touched my virgin hole. I tried to relax and push down at the same time. My ass opened up a little and he started to go in. When his cockhead made it past my entrance I stopped to get used to it and I heard him groan. I let go of his cock with my hand and I arched my back and started to slide the rest of his cock up inside me. I slowly let it go up in me and finally I felt his pubic hair on my ass and he was all in. I felt soooo full. I started to go up and down on his cock getting a rhythm.

His hands were on my ass as I rode him. I heard him say that he loved how hot and tight my pussy was. I smiled to myself at being able to trick him into thinking he was fucking me like a real woman. As I continued to ride him I reached up to pinch my nipples and thought that's what I really wanted. A pussy. The pressure from his cock was working on me. I knew I was going to come soon. I picked up the pace hoping he was close too.

I reached down inside my panties to rub my “clit”. I was so full of his cock I couldn't take it. I started to shudder and a clear fluid started oozing out of me. My ass was spasming too and that set him off. He grabbed my hips and started ramming himself in me as far as he could go. I then felt it deep inside. His cock was shooting his seed deep inside me. He kept thrusting and shooting almost like he was trying to make sure his sperm got deep enough in me to get me pregnant.

Finally slowing I felt his cock start to soften. I rolled off of him as it pulled out of me. I kept my ass cheeks tight holding his load inside me. I crawled up and laid next to him and he kissed me. He told me how fantastic I was and what a tight pussy I had. He held me close and the drink and exertion finally made him fall asleep.

I laid there a little while enjoying the closeness. I moved my hand down his chest and thought how lucky his wife was, if he was married, or whoever gets to be with him. I slowly moved out from under his arm and got up off the bed. I collected my things and went into the bathroom. I checked my makeup and repositioned my thong and made sure nothing was leaking down my leg. I put my bra and dress back on and headed for the door. He was snoring softly as I slipped out and went back downstairs. I got my car from the valet and drove home.

I knew what I wanted now. This would be the final step. It would be risky and there would be no way back from it. I would call my plastic surgeon and have her recommend a doctor to do the surgery.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

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