Of Course My First Time Pt. 01

These stories are my darkest fantasy's
I was 32 recently divorced from a beautiful woman. She really broke my heart and was getting to the point that I didn't care about anything anymore so I decided to try and fulfill my fantasies.

I always very cautious and aware of what people thought about me but at the time I was so broken hearted I just didn't care anymore and I was willing to go for it.

Didn't have a lot of money but I was able to find a buy now pay later department store online.

Needless to say I went a little overboard I bought four bras 45$ each with matching panties I bought at least six dresses that totaled over 550$ and of course slips to go underneath (I love slips) I also purchased Wolford pantyhose for $60 a pair which was crazy but oh my God how they felt.

This was the first time I had purchased clothes that actually fit me I was always wearing my wifes for my sisters when I was younger.

I found a Rene of Paris wig online on eBay it was blonde shoulder length and just looked so good compared to all the other cheap ones I bought at Halloween stores.

So one night I decided to get dressed and put some pictures online I'm 5'7 about 120 lb I had a small drug problem that got worse and this caused me to lose a lot of weight so I was pretty tiny.

I put on the woolford pantyhose and at the time I only had bird seed inside a pantyhose for breast but they worked just fine I had just started taking hormones so they really hadn't started working.

I shaved every bit of hair off my body and I made sure that I got every single bit. I shaved almost all my eyebrows off. if I was going to do this I was going to do it right. I put on a white satin bra with matching panties put on the woolfords and started on my makeup I was very proficient at putting on makeup I would sometime put makeup on for my wife and dress her up sexy and have her dance around so I knew what color foundation to wear I knew how to put on eyeliner and how much blush to put on my cheeks. I had an a-line black dress that was just above my knees and some tall boots. I'm sure you've heard this a million times when I looked at myself for the first time I could not believe it. but it was true and if you were there you would agree I was truly gorgeous I was so turned on that I began to dance around the house as if I was a topless dancer dancing for men I had my blinds open and I didn't really care if anybody seen me it felt unlike anything I ever felt in my life it was so exhilarating I had so much energy and I was ready for a man.

I looked so damn good. At least that's the way I felt about it and after putting the pictures on Craigslist and getting 200 emails in one day I think men felt the same way.

Anyway the first time.

I met a guy who was probably in his late 40s he look like the type of guy that didn't have very many sexual experiences he was a little nerdy and I really wasn't sure what to expect when he came over I just purchased a two layer slip that was light pink and over it I put on a flower design dress that was just below my knees it was very sexy and very in style

I put on my heels which I tried to keep them low so I wouldn't be too tall and waited for him to arrive.

When he arrived I was very scared I had never kissed a man much less slept with one I had really had no homosexual type of contact and I was also at the time the scared of AIDS so I thought I better play it safe no kissing just a little grinding maybe.

He sat on the couch and I sat on his lap I begin to grind my ass into his cock it immediately stood up he reached around and grabbed my breast and I could feel his hot breath on my neck and his whiskers rubbing against me then I felt his tongue travel towards my ear this is my real weakness if you stick your tongue in my ear I just fall apart and that's just what he did.

I could not stand it I slowly turned my head around no longer worried about AIDS or anything else our lips met in the most wonderful kiss his tongue was deep inside of my mouth I was eagerly slurping it up I sucked his tongue and I had never been so turned on I stood up and grabbed one of his fingers with one of my fingers and led him towards my bedroom I could not believe what I was doing I was fixing to go to bed with a man. When we got to my bedroom he removed his clothes I pulled off my dress and left on my pink slip which is so soft and of course my pantyhose we got under the sheets and I felt his warm body getting next to mine I kissed him and I moved my hand down towards his cock pulled down his underwear and I slowly went down on him slurping up his cock kissing it licking it pulling it i licked his balls up and down I'm very sensual person and I was out of control I got on top of him and I begin to slowly kiss him over and over and over with small little kisses and then for some reason I screamed I love you he rolled me over got on top of me and his cock started pressing against my ass cheeks I didn't know what to do I had never had anal sex but I guess he knew what he was doing cuz he slowly worked it in I was gripping his cock with my ass he was pounding me so f****** hard still we were kissing which really turns me on and usually I don't come very fast but I exploded all over him he finally did the same and his cum was oozing out my ass it felt exhilarating and forbidden I knew this wouldn't be the last time. After I kissed him good night and he begged to see me again I decided I wanted to go out.

I had never gone in public and after he left I put on some shorts and a long t-shirt and my new girly tennis shoes and I went for a walk in the neighborhood as a woman and I knew this was what I wanted from now on and yes there was more to come.

I always felt the more forbidden the better as they say I'm not easily amused so forbidden would soon become my downfall no one was off limits I tried to think of the most forbidden person and I decided it would be my stepfather who I despised but I news the way that I looked he would not be able to turn me down and I was right let me know if you want to hear about it.