Things happen in the life of a transvestite who prefers to live life on the edge, it is a sense of danger that fires me on to meet strangers in the most isolated of places. I visited a town in South of England three years ago at the invitation of a Danish man I had met in London and spent the night with. I met him in a gay bar in Earls Court where transvestites often to go to meet men for sexual contact. I was staying in a friends apartment and she was at work so I had decided to dress up as a woman and visit the bar. I was only in the bar about ten minutes when a very handsome man of early middle age came to my table and offered me a drink. We chatted for a while and he invited me back to his hotel room in Central London. He was going to the coast for the weekend and he invited me to come along, I accepted and stayed with him at his friends house for the weekend.
The weekend was very erotic and he kept me in the bedroom for most of it, I told him I wanted him to cane me in the afternoon, he went into town and returned with wine, a roll of slim cord and a cane he had bought in an antique shop, he told me he spotted it walking past the shop. We drank the wine and he tied me to the bed posts, firmly but not too tight, he tied my ankles to the side of the bed when he had positioned me as he saw best to beat me. He told me to push up and to offer my bare ass to his cane. He came down very hard three times and I screamed, he pushed my panties into my mouth, he was concerned about the neighbors hearing my screams. He caned me hard six times and then stopped, he took the panties out of my mouth and asked how many more times I wanted the cane, I wanted much more so he returned my panties to my mouth and beat me a dozen more times with the cane, he brought a mirror to let me see the thin welts on my bare ass, I was red raw and the welts were pumping, I was very sore and he knew I had had enough, he untied my ankles and left me to suffer in silence.
He told me he would be off to town and that my beating wasn't finished, he told me he was well versed in the art of pain and that I would be sorted later on in the evening, he left me on the bed whimpering and crying with the soreness of the beating. It was two hours later when he returned, he smelt of alcohol and smoke, I craved a cigarette and he lit it for me and held it as I smoked, I inhaled it hard and when finished I asked him what he intended to do to me, he put out the cigarette and untied my wrists, he led me from the bed into a room which was totally empty, the floor was wooden and highly polished. He led me to the middle of the room and ordered me down on my hands and knees, he placed four leather strips in front of me then he placed the first strip over my wrist and proceeded to nail the strip to the floor with a hammer, he then did the other wrist and moved down to my ankles, I was nailed by leather strips doggy style to the wooden floor. He went out and returned with a pad for my knees, he said I would need it as this was going to be hard on my knees. He said I should make up my mind if I wanted it rough, I was to nod if yes and turn my head if I didn't, I was so excited and turned on I nodded and he left the room and returned with two mirrors, he carefully positioned them so I could see my own beaten backside from the earlier beating, it turned me on.
He shoved lubricant in between my anal lips and used his fingers to open me up, I knew he was going to fuck me at some stage,however he left the room again and returned with a huge vibrator, he had went to a sex shop and he said he bought the meanest and biggest. He then stood where I could see him in the mirror and took off his clothes, he stood semi erect and naked, his arms were glistening with sweat as I saw him pick up my panties again and place them in my mouth, he had soaked them in red wine, I saw him pick up the cane and my mid drift tensed as I watched him circle around me, then I watched my beating and the pain was making me jerk, his caning was severe, now I knew why he put the pad down, my knees dug into the thick leather and I felt my body shudder as the cane cracked down on my bare ass, then he started aiming for my thighs. After several harsh canes had hit on me he stopped, I was wet with sex juices as he took the huge vibrator and started to rub it hard into my anus.
I was delerious with sexual energy and sore from the caning as he used the tip of the vibrator to enter my ass, he used it firmly and I felt my anal lips expanding, he pushed it into my ass and then started to push and pull, the feeling was exhilerating, I was very hot and sweating, my shaved cock area was moist and very hot, I could smell myself being fucked and I could see the huge vibrator enter fully up my ass , he tied his belt to my groin and tied it tight so the vibrator was trapped inside me, it was humming and whirring and fucking my hole. Then I watched him take the cane and I tried to scream out as he caned me so hard, I could see my bare ass covered in welts and he hit my arms and underbelly. I was tied to the floor helpless as he caned the daylights out of me, I could feel the huge vibrator sodomizing me and it seemed like a bomb was going off as it vibrated and fucked me. He hit me several more times and then he knew he had done his job, I was in so much pain as I watched my bare ass vibrating with the huge rubber cock inside my ass. It fucked me until the battery died and I watched the Danish man masterbating in sexual excitement, he stood over my naked body and emptied his sperm filled cock on my back and ass.
I was exhausted as I turned my head to let him know I had enough, he undid the belt and the big huge rubber cock slipped out of my ass, he undid the strips of leather and I saw my body caned and raw, he carried me to the bedroom and he give me red wine and cigarettes, I must have slept for hours, when I woke my asshole was burning and my body was sore, in a strange way I felt great surges of pleasure as the pain worked around my body. It was worth every hit of the cane and it lasted for a week. He got hard with the sight of his work and he bid me to service his erection which was several times over the days we stayed. He never caned me again as he knew he had been too harsh. How much is too harsh, I still think back to that beautiful erotic and painful weekend. When you are nailed down on all fours like a dog and whimpering in pain and being sodomised by a huge erubber cock you know you are alive and the object of great desire to a complete stranger makes it so much more erotically appealing.
7 years ago. July 16, 2017 at 12:18 AM