Lyn Sets Me Up With a Stranger – BDSM – Free Sex Story

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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 40 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 really stuck a chord with her and 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”. I had my initial apprehensions on this but Lyn manipulated me so cleverly that I eventually agreed. 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 only 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 makes it clear, in no uncertain terms, that I should be pliant to all his whims and do whatever it takes 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 Karl.

It was a cold winter evening, the day I am supposed to meet this guy in question. I am dressed in a fake beaver coat, that covered the entire length of my body upto my ankles. But the catch is that I am almost naked under my coat. Inspite of the scathing winter cold, to comply with Karl’s wishes, I only wear 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 are black.

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

When I knock on the door it takes a while before the door is 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 am dressed (undressed would be a better word) the way he asked. Only after being satisfied with his inspection he lets me in.

With a few words, he lets me know that he is Karl with whom I interacted a week back. As I come inside and look at his face more closely, i feel cheated by Lyn. 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. 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 makes no attempts whatsoever to engage in some small talk or make me feel at ease.

“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, takes care of my fur coat and orders me to remove my little panties.

I suddenly feel that the lighting in my room is rather intense. I am embarrassed and shivering and it is not only because I am almost naked. It is rather because Karl had not wanted that I get rid of all the body hair which cover almost all my body. In front of this man, who is almost unknown to me, I believe that these hair, humiliate me much more than my nakedness.

i feel an urge to urinate and ask rather politely if I could use the bathroom, but Karl once again ignores my request. He asks me to sit on chair and remove my flat boots. He brings 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 probably belonged to his Wife. Karl grabs my lower calves with his fingers and tries to slid the pump into my foot. But the shoes are 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 are 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 are shod in these pumps he makes me get up and asked me to parade in front of him around the room.

He sits relaxed in the couch with a glass of wine as he watched me very intently parading 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 couldnot understand what pleasure he is deriving by humiliating me like that. My legs are shaking and I have great difficulty walking on those sky high stilettos which I believed were never made for walking.

After well over ten minutes of this show of mine, he asks me to rest on the chair.

Karl seems rather pleased with my performance. He seized my calves with his fingers and 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 then kisses me on my lips. He smelled of alcohol and tobacco.. Surprisingly, I feel excited when he inserts his tongue into my mouth. He continues to play with me like that, with a flood of kisses and caress. After a while, he fastens leather bracelets on my wrists and ankles. He forces my arms behind my back and padlocks my wrists bracelets. He then fixes a chain to the leather bracelets which circles my ankles.

When this is done, he helps me to my feet and makes me walk, in front of him, up the staircase which leads 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 does not even help me to climb the stairs. With my heels way too high and the wicked chain which prevents me from raising my feet, on several occasions, I have the very clear impression that I will never manage to reach the second floor. On the other hand, this guy seems to get an insane pleasure to spank my buttocks and to see me in pain.

In the room, he finally unfastens the chain between my ankles and wrists and put me on all four on the edge of the bed. He takes out a leather belt and starts hitting me from behind. At this point, you could well guess the state of torture I was in. My feet are hurting from wearing those tight heels, my thighs are on fire from the blows and I feel like my bladder is full but I am forbidden from reliving. Karl draws my legs wide apart and continues to hit me so viciously that I cannot distinguish anymore which of my thighs or my buttocks make me suffer the most. Tears well up my eyes and I am almost about to cry.

The remainder of the evening runs out very quickly. Karl applies 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 to me not to move, he tries to fuck me up the Ass.

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

I feel so relieved when Karl finally lets me go! But the journey back home also proved to be hairy. Back in my car, I am shocked to look at myself in the mirror. My wig is askew, my makeup is ruined, and my lipstick is smeared. I look like a female impersonator gone berserk. I am still so nervous that my hands are shaking and I find it difficult to concentrate on my driving. By now my I am feeling that my bladder would burst before I reach home. But considering the state I was in, it was impossible to think of stopping my car and getting down. Finally, i just couldnot stop myself from peeing right inside my car, and soiling my panties, my beaver coat and the entire bucket seat upholstery of my car. What a comfort when I finally reached home.

Later in the night, I called up Lyn and reported to her in detail about my adventure with this guy. I feel pretty embarrassed telling her all these details but I made her laugh for almost half an hour.

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