I have been cross dressing since I was 15yo. I started wearing some of my sister's panties and as I got older I could wear my Mom's panties as well as her pantyhose. When I got old enough to get my own place I could expand my wardrobe and finally buy the high heels and boots I always wanted to wear with the outfits.

When I was able to dress fully and parade around my home without the fear of being caught by a family member I realized I was getting sexually aroused. Before I could wear the things in secret and take them off and that was it, my thrill of cross dressing was satisfied.

Now I was alone and there was no fear of being caught and suddenly I was overwhelmed with sexual desire. I have a decent size cock about Seven inches. My cock would be hard as steel within the confines of my panties. The urge to use my cock and ejaculate tormented me almost every time I dressed up.

I had never been really into Porn before. Watched a few Video's here and there, but my own thrill of cross dressing excited me more than any Porn video could. Since that wasn't the case anymore I began to watch those video's more often.

Right away the straight fucking video's lost their appeal, and I delved into the darker side of the industry. I began to watch CD and Tranny Porn video's and instantly I was hooked on them for sure. I would get dressed up and have a night of masturbation frenzy watching those video's of CD or Tranny's sucking a fucking in every way possible.

What I didn't realize was the effect those Films were having on me. I made less effort to date women now and I was cross dressing more during the week. The idea of being with another CD or a Tranny entered my thoughts more often. After a while I realized there was a hierarchy in the CD or Tranny world, you were either a top, bottom, or versatile. I knew I was a top even though I had never been with anyone. I had a hard cock and dressing up only made me feel harder, and I wanted to use my hard cock to fuck.

I had heard about Craigslist years before but never had a reason to look at the website until now. When I learned to navigate it I found what I was looking for, it was like Christmas for me. So many people wanting and needing things just as I did, not all qualified for various reasons of course.

I began to see a pattern emerge for CD's that most were submissive. Instantly I was aroused by the idea of being with another cross dresser that wanted someone to take control over them for a little while. I began my search, exchanged pics with serious inquires. Then I had to decide if I was going to take the next step. Until that moment I had always been with women off and on and very happy with the female body. Now I was going to uncharted territory of being with a CD or Tranny.
and
Thankfully most of responses were bottom submissive's. Many sent me pics of the small cocks in chastity devices tucked away inside their sheer panties. Their desires were to please me anyway I wanted. I was very selective, I only wanted the ones that dressed completely from head to heels. Full makeup, wig, as well as clothing.

The responses poured into my email box daily, we exchanged Pics and went from there. Within a few weeks I was entertaining during the week as well as weekends. I loved how they savored the length of my cock, seeing their lipstick around the base of my cock aroused me very much.

Their submissive nature excited me even more if that was possible. I converted one of my bedrooms into a Dungeon like setting. I attached chains to the walls and from the ceiling as well. I spent money on a padded bench in which I could chain them down and fuck them in that manner as well.

Then one night I met Janice and my world would change again in ways I never thought. Janice was a beautiful Tranny and also a submissive. She told me she was strictly bottom and that she wanted to be treated like any other bottom girl.

Janice came over and she was dressed sexy as hell, her breasts were not overly large but firm for sure. She wore a miniskirt with stockings and heels of course and after a bit of small talk I took Janice to the Playroom.

I chained her wrists above her head and peeled her top down exposing her breasts. I couldn't remember how long it had been since I had been this close to a female form. I relished the idea of teasing her nipples and biting them hard enough to make Janice squeal. I wore black vinyl opera gloves and slid my hands all over Janice's body. I even raised the back of her miniskirt and gave her a rather harsh spank on her ass. Janice squirmed and the sound of her voice let me know she enjoyed what I was doing.

When I told her I had a riding crop and flogger for ass Janice was almost begging me to use them on her. I walked around and took hold of the miniskirt and slid it downward over her hips and let it fall to the floor silently at her heels. I took notice of her shapely legs in her nude stockings she wore with her heels, and then I turned my eyes to what was being held in place by a thin material of lace.

Janice's cock was tucked inside but looking at the size of her cock, I knew it wasn't going to be held back for long. Janice was big, I could tell even before she got hard. Her cock was thick and it's girth already strained against the lace panties she wore. I know I stared at it for a few more moments, having a difficult time looking away. Most of the people I had been with with small to average in size, Janice was the first person that had a cock of any reasonable size.

I finally moved behind Janice and went about doing what I loved to do. Within minutes Janice was squirming and begging me for more and sometimes a little less. Her cheeks were nicely pink and she wanted to go a bit further if possible. I gave her what she wanted, getting aroused at the way she squirmed. I flogged her breasts, pinching her nipples until she could barely speak. I looked down and saw her cock was now protruding out below the waistband of her lace panties. Janice was fully erect, the veins filled with blood and there was even a bit of wetness at the tip of her cock.

I dropped the riding crop to the floor and reached for her cock. With my vinyl gloves I caressed the head and slid my hand over the rest of her shaft. Janice instantly squirmed and breathed harder. I stepped to her side and touched her hardness again, this time squeezing her cock a bit more. Janice begged me to stop and it only aroused me more. I reached over and pulled the rest of her cock out from behind the lace.

I slapped it and Janice jerked, even lifting one foot from the floor. She groaned from the pain and pulled at the restraints above her head. I took the crop from the floor and tapped her hardness a few times, hearing Janice groan with pleasure had me hard within the confines of my panties as well. I went back to work on her ass again, the crop and flogger bringing the pink color close to red once more.

Janice told me she needed a break and I released her wrists from above. I led her to the padded bench and had her kneel and lay down on the flat surface. I secured her quickly and walked behind her ass. Her cock hung down and curved slightly, I took it in my gloved hand and squeezed it. Janice moaned and I felt her thick cock throb even through my gloves.

Normally I would have teased my partner a little longer before I took them but I could barely contain myself with Janice. I reached down and lifted my vinyl skirt and slipped out of my panties. Standing behind Janice I slipped the condom on and inserted my hardness into her.

I filled her quickly and Janice squealed and squirmed as I forced all of my hard cock into her behind. I tried to fuck her slowly, trying to hold back the erotic sensation of this moment. I thrust into Janice a bit harder and faster and already I knew I was going to last the way I had done with the others. I fucked Janice like a owned her, just taking what I wanted. The pleasure was too great and the way Janice begged me to fuck her sent me over the edge and I began to cum all too soon. I didn't stop fucking her until the last sensation of release had passed.

I finally pulled out of Janice, the end of the condom was heavy with my cum. I stood back and looked at her still strapped to the bench with her cock still as hard as before. I pulled my skirt down and reached for her cock once more. Once again it pulsated in my grasp and I knelt down and stroked it a few times. Janice moaned with pleasure and I slowly began to jerk her off. The more her cock throbbed and pulsated the more turned on I was even though my erection was fading.

Then suddenly I realized that for the first time I was going to put a cock in my mouth. The sensation almost made me dizzy, the warm flesh sliding between my painted lips and over my tongue. I took her cock as deeply as possible, not able to take all of Janice. She jerked on the bench above me, her hard cock throbbed within my mouth. The rush of excitement seemed to lead me on and there was no turning back.

I stroked and sucked her cock as Janice squirmed above me still chained to the bench. Almost at once I could taste the precum, and knew Janice was very close to cumming. I worked her good and now her cock throbbed as my mouth slid back and forth along her shaft. Thankfully Janice gave me warning just in time as I pulled her cock out of my mouth, I could see my own lipstick on the moist flesh of her cock now. I held my one hand at the tip of her cock as I jerked her off faster.

Moments later I felt a spasm through my gloved hand and then saw a solid stream of white cum hit the palm of my hand almost at once. I kept stoking her cock, almost milking her if you will, the thick fluid coated the black vinyl of my glove and dripped off the sides quickly.

I didn't stop milking her until I had about every drop Janice had to give. Finally I let go of her cock, it was still swollen from arousal and slightly red in color from my lipstick. I held her cum in the palm of my gloved hand, thick hot fluid that maybe one day I would have to take the next step and try as well........................... ......................