My First Encounter

by Beata Bockman

 

I am thirty-five years old and I have been dressing since I was twelve. Most of the time I would just dress at home, once in a while I would go out driving but that's about it. My routine was to get home from work, get out of my male clothing, get in to a dress and then go online. I was starting to get bored with the dressing and going online thing, after all how much porn can you download. I was hoping to meet someone online. I have never met anyone while dressed and I very much wanted to change that. I had many on line friends but I just did not want to meet another girl and all of the guys that I met just wanted to meet after a three line instant message. I was not that kind of girl. I felt that I had to get to know someone first before I would meet someone and then how would we meet? I was not into public places and even as a guy I did not like going to clubs. It seemed that I was destined to be a virgin as a girl.

One evening I was dressed and on line when I received an IM from a man named Bill. He was 50, married and had kids. Not exactly what I was looking for but he seemed like a great guy. After talking for about an hour he asked if we could meet. Finally, I may loose my cherry, I thought. I suggested a few days. That's when Bill said that we could only meet during the week. OK, I thought what the heck, a weeknight would be good too. I just wanted to get this meeting thing over with. That's when Bill said that he could only meet during the day. My heart sank. I just started a new job and it would be a few months till I had any vacation. He was disappointed too. He could get time off from work but he could not let the wife know. If he disappeared on a weeknight the wife would get suspicious, there had to be a way.

We IM'ed each other for a few months getting to know one another better. This was when I discovered that Bill had a few kinks. He loved women in boots and leather and he liked to be tied up and fucked in the ass. How fortunate for me I thought. For some reason I wondered what his wife looked like.

I was at my job when the boss said that he was going to be out of town for a few days. Humm, I thought about Bill. Maybe we could meet. That evening I was dressed and online as usual when I got an IM from Bill. I told him that we could meet but it would have to be tomorrow. He said "hold on, let me check". Seems that his morning could be free. I had a date! I could not wait. We decided on a hotel near his work. I would check in and get dressed and page him with the room number. He said that he would show up about 9:00 am.

I had to get ready. I got my stuff together, making sure that I had my makeup, my breast forms, lingerie, and my outfit. I tossed it all in a suitcase and then I tossed some rope on top of it all and closed the case. I was ready. I had a heck of a time getting to sleep I was so excited.

The next morning I got dressed in jeans and a t-shirt, grabbed my bag and drove to the hotel. I was so nervous I almost bumped another car more than once. When I got there, I parked, grabbed my bag and headed into the hotel. Check in was uneventful and I quickly got to the room. The first thing I did was page Bill with the room number.

I checked my watch, it was seven AM, and I had two hours to get ready. I quickly got into the shower. I shaved my legs and chest, it felt good to get rid of the hair. I patted myself dry and quickly painted my toenails with a dark shade of red. Next I got out my breast forms and attached them to my chest with glue that I had bought last week. This was the first time that I had ever attached my forms with glue. I usually just stick them into my bra. This was a new feeling for me to be able to go bra less. I could not help myself, I had to dance around the room. The feeling of the breasts jiggling was incredible. I looked at the clock, one hour to go. I had better get busy getting the rest of myself together. I applied my makeup and then my blond shoulder length wig. Looking in the mirror I felt turned on by the creature that was appearing in front of me. Thirty minutes to get dressed. I hoped that Bill was not early. First I put on my lacy black bra, garter belt and stockings. Next I put on a thong that matched the bra. Next I slipped on my leather dress and then my knee-high boots. I had twenty minutes that left just enough time to attach my fingernails. I carefully glued on my nails, they were pre painted the same shade of dark red as my toes. Looking in the mirror I looked great. I could not help my self, I just had to strut around the room.

Just then I heard a knock on the door. I was so nervous, I felt like I was going to throw up. I quickly tossed all my male things in my suitcase and stuck it in the closet. Then, another knock on the door. Just then I realized that I had no idea what Bill looked like, I mustered my best female voice and said, "Who is it".

"Bill" was the reply. I opened the door and let him in. He was a good looking guy, tall, average build, with salt and pepper hair.

He said "Hello, wow you look great"

"Thanks" I said

That was when he pulled out a rose. "For you my sweet"

Having never received a flower before I was not sure what to do. I took it from him and smelled it. I realized that I had never smelled a flower before. I said "Thank you" and gave him a kiss on the cheek.

I closed the door and we went into the room. We sat down next to each other and talked for a bit. We had known each other for months so it was like old friends that had not seen each other for a while. After a bit, Bill put his hand on my knee and looked into my eyes. I felt drawn to him. We started kissing. Softly at first but soon we were kissing much deeper. Bill started running his hands over my body or maybe I started running my hands on his first. Before long I could feel my hard-on straining to come out of its tucked position. Fortunately the thong was holding it in place. I started undressing Bill. I soon had his jacket and tie off. I was unbuttoning his shirt and he was trying to unzip my leather dress.

I said, "That might be easier if we stood up". Once we were standing we continued to embrace and undress each other. I let my dress fall to the carpeting.

He paused to take a look. "WOW" he said. I just smiled. "Can you walk around the room a bit?" asked Bill.

I was only too happy to oblige. With my best hip swaying walk I walked over to the door and turned around. Bill was checking me out from head to toe. When he got back up to my face we locked eyes and I walked back to him. When I got close I pushed him back on the bed. Kneeling in front of him I proceeded to undo his pants and pull them down. He was wearing boxers. I grabbed the elastic and pulled them down as well. His raging hard on was standing at attention. I had never seen another man's penis this close. I must have hesitated because Bill asked, "What's wrong"

"Nothing" I answered, "Yours is the first one that I have seen this close," I added. Bill let out a little laugh but just then I kissed the head. I licked it. It tasted just like I expected, tasting like skin. I could smell the soap that he used. I took the head into my mouth, Wow, I am giving my first blowjob I thought. His penis seemed to get larger the more I worked on it. I licked his balls and the shaft, doing everything that I like when a woman gives me a blowjob. Soon I felt Bill grow even larger in my mouth and he started to buck a bit. He was about to cum. I felt the sperm race up the shaft and into my mouth, as my mouth filled with his cum, it felt wonderful.

"Wow' said Bill, "That was the best blow job that I have ever received.

My hard-on was raging and I though I was going to cum right there.

Bill said, " Remember when I said that I liked to get fucked by girls like you" as he turned over and got on all fours on the bed. I quickly stepped up behind him grabbing some lubricant out of my purse. I quickly greased my dick and then his ass being careful not to run my fingers on my raging hard on too much, I did not want it to go off prematurely. I placed the tip of my dick at the entrance to his ass and started working my way in. I could hear Bill moaning as I worked away. Soon I was all the way in his ass. Then I started pumping away. This was the first time that I had ever fucked anybody in the ass. It felt so tight. I reached around and stroked Bill's raging hard-on. It felt incredible to touch another mans dick while fucking him. Soon I felt him cuming again all over my hand. That triggered me and I came in his ass. We collapsed together on the bed gently kissing.

"That felt incredible" said Bill. "I which my wife would do that to me". We kissed for a while. Bill noticed the time, it was almost noon. We both had to get back to work. Bill took a shower and I contemplated what we had done. I had become a woman, well almost, I still have not had anyone fuck me, but that could be our second date.

  

  

  

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