Lyn Sets Me Up With a Stranger

Before starting with the actual story, I would like to say a few lines about myself. This would enable my readers to understand the kind of individual I am and appreciate the story better.

I am a 50 something submissive crossdresser. I am outgoing and adventurous by nature and do have occasional discrete encounters with compatible individuals, men and women alike. In one of my earlier stories, "Meeting Lyn" I had described my encounter with a beautiful dominatrix named Lyn and my first session with here. In the course of time, I became one of her regular clients. She is an amazing woman with a fund of ingenuity and skill and made me live some fantastic appearances in humiliation, domination, spanking and bondage. She also satiated my urge to dress and feel like a woman in every way. Lyn gave me lessons on dressing up as a woman, how to apply mascara and makeup and useful tips on looking like a genuine woman in public. She was the one who christened my female name as "Jessica".

Gradually, she started to convince me that no matter how passable I would look in public as a woman, I would never have the feeling of being a complete woman until I had a one night stand with a man who would take away my "virginity". The next weekend when I was at Lyn's place she told me about the guy she had chosen for me and we had a brief conversation with him over the phone. His was a man of German origin named Karl and lived a few miles away from my place. He could speak broken English and told me that he was a top who liked dominating women and transsexuals and also spoke at length about the way I had to present myself to him for our "date". We agreed to meet the coming weekend when his wife would be away for the evening.

Lyn made it clear, in no uncertain terms, that I should be pliant to all his whims and do whatever it took to please Karl. She also lets me know, that post our meeting, I should call her up and provide a full account of my meeting with this guy.

It was a cold winter evening, the day I was supposed to meet Karl. I was dressed in a fake beaver coat, that covered almost the entire length of my body upto my ankles. But the catch was that I was almost naked under my coat. Inspite of the scathing winter cold, to comply with Karl's wishes, I only wore a corset (laced tight enough so that both ends met in the back), a pair of stockings, flat knee high boots and tiny lace panties. All my clothes were black.

. After quite a few difficulties I manage to find his house which was situated in a rather decrypt bungalow on the edge of the town.

When I knocked on the door it took a while before the door was opened and I could see a man looking at me. Before letting me inside his house, I must offer him a peek-a-boo from my coat so that he could check whether I was dressed (undressed would be a better word) the way he asked. Only after being satisfied with his inspection does he let me in.

With a few words, he lets me know that he is Karl with whom I interacted a week back. As I came inside and looked at his face more closely, i felt a bit let down. Karl was no prince charming or even a decent looking guy. He had a lean angular face, sharp squinted eyes and a scruffy unkempt salt and pepper beard. He looked rather mean and menacing to me. Definitely not the type of guy any woman would want to go on a date with (And i am a woman after all! ). I quickly glanced through the house and saw that the place was shabby and unkept, with odd pieces of furniture strewn around and the lighting was minimal.

Karl made no attempts whatsoever to engage in any small talk with me or making me feel at ease in his place.

"Nice meeting you Karl", I said and tried to flash a smile hoping it would make the atmosphere more congenial between the two of us. In response, Karl only let out a small incoherent grunt, took care of my fur coat and ordered me to remove my little panties.

I suddenly felt that the lighting in my room was rather intense. I was embarrassed and shivering and it was not only because I was almost naked. It was rather because Karl had not wanted that I get rid of all the body hair which covered almost all my body. In front of this rather hostile unfriendly man, who was almost unknown to me, I felt that these hair, humiliated me much more than my nakedness. He asked me to sit on a chair and remove my flat boots. He brought with him a pair of black patent leather pumps with treacherous five inch heels. I could see immediately that they would be too small for me and I presumed they belonged to his wife. Karl grabbed my lower calves with his fingers and tried to roughly slid the pump into my foot. But the shoes were just too small for me. Karl, appeared angry with himself and continued in his attempts until he finally succeeded in squeezing my feet into the shoes. They were so tight and my feet started hurting immediately after wearing them. But these are the shoes he wanted me to wear. When both my feet were shod in these pumps he made me get up and asked me to parade around the room.

He sat relaxed in the couch with a glass of wine as he watched me walking around the room, as if he was watching a Victoria secret model prancing in the catwalk. On the other hand, I had neither the figure nor elegance of a fashion model. And with all the body hair covering my body and with my sex, which does-not have any feminine characteristics, well in sight, I just could not understand what pleasure he was deriving by humiliating me like that. I felt i was maintained in a state, which was more humiliating than being stark naked . My legs were shaking and I had great difficulty walking on those sky high stilettos which I believed were never made for walking.

But Karl seemed rather pleased with my performance. After well over ten minutes of this show of mine, he asked me to rest on the chair. He fastened leather bracelets on my wrists and ankles. He forced my arms behind my back and padlocked my wrists bracelets. Then using ropes my ankles were tight to the chair legs thus leaving my legs drawn wide apart and my sex in sight.

When he brought to my lips, a glass of red wine, I feared that he might dope me. But considering the situation I was, did I had a choice to refuse? Then after depositing the wine glasses on the table, he started to caress my legs going upto my sex. At this point, shivers invaded my body and my sex didnot take long to react.

He continued to play with me like for for well over few minutes, and then, as soon as the wine glasses were empty, he unfastened the ropes which tied my ankles to the chair and fixed a chain to the leather bracelets which circled my ankles.

When this was done, he helped me to my feet and made me walk, in front of him, up the staircase which lead to a room, located on the upper floor. Apart from a few good slaps applied expertly to my large buttocks, made even more obvious by my too tight corset, he did not even help me to climb the stairs. With my heels way too high and the wicked chain which prevented me from raising my feet, on several occasions, I had the very clear impression that I would never manage to reach the second floor. On the other hand, this guy seemed to get an insane pleasure in spanking my buttocks vigorously and seeing me in pain.

In the room, he finally unfastened the chain between my ankles and wrists and put me on all four on the edge of the bed. He took out a leather belt and started hitting viciously on my thighs and buttocks. At this point, you could well guess the state of torture I was in. My feet were hurting from wearing those tight heels and my buttocks were on fire from the blows being reigned on me. Karl drew my legs wide apart and continued to hit me so hard that I couldnot distinguish anymore which of my thighs or my buttocks made me suffer the most. Tears welled up my eyes and I was on the verge of crying.

The remainder of the evening ran out very quickly. Karl applied a generous portion of a lubricant on my anus, he puts a ball gag in my mouth, puts a condom on his sex and, while strongly recommending me not to move, he tried to fuck me up the ass.

However, I was so tight and so scared that, even after several attempts, he did not succeed to penetrate me. He must masturbate to succeed to ejaculate finally.

I felt so relieved when Karl finally let me go! Later in the night, I called up Lyn and reported to her in detail about my adventure with this guy. I felt pretty embarrassed telling her all these details but I made her laugh uncontrollably for almost half an hour.