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By (user no longer on site) OP
over a year ago
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Ok, so this is my first real stab at writing erotica... I very much enjoy reading other people’s writings so just thought I would attempt to write something myself.
This piece is basically one of my biggest fantasies, written in a first person perspective and includes scenarios I would love to play out one day... I hope you enjoy!
So I am a closeted crossdresser, to the outside world I put up a facade of being a normal straight guy. I have had a number of girlfriends and casual hookups in the past and do find women and their bodies attractive although sexually have always had a few issues when it comes to ‘doing the deed’. I have always struggled to get or maintain an erection when with a women and this is made somewhat worse by the face I am very VERY small in that department.
My crossdressing started as a teen. I have an older sister who often went clubbing and had a number of mini skirts and dresses, I had also began to notice an ever increasing collection of thongs appearing on the drying rack. These were not standard boring cotton thongs, they were sexy, sparkly, metallic, microfibre and spandex material and every time I saw them my eyes were drawn to them.
One Sunday when sitting at home alone, curiosity finally got the better of me. I went to the drying rack, picked out my favourite thong, which was a metallic silver and a stretchy spandex material, I stripped naked and put it on. I was instantly aroused and very quickly got a full erection... and so it went on like that for a few months, just wearing her thongs and nothing else whenever I was home alone. One day, as usual I went to the drying rack to see what I could wear that day and noticed a short pink mini skirt and something that resembled a top (It was a black bandeau top). I also noticed that she had a padded bra the same colour and material of a red thong that was on the rack. I took all the items off the rack and slowly changed into them. It felt amazing, I was scared as I felt like I could come just by walking around in the outfit... well after that I spent the next few years, until she left home, dressing in her clothes whenever I could... I guess that should have been an insight into my future and what I was to become.
15 years later: Over the years I have still dressed on occasion, building up a collection of outfits and then throwing them away telling myself I won’t dress again but the urge remained. It is in the last 2 years or so that I have decided to embrace this side of me and when I became single a year ago I decided to stay single and explore my crossdressing and the BDSM/Fetish scene.
So I had been exchanging messages with a guy on a local swinging site, I had become comfortable (too comfortable) talking about myself, my desires, my deepest fantasies and my personal life. We had exchanged pictures and he was tall, muscular and attractive. I’m completely sub and love to be dominated and used. We discussed meeting and finally planned a date. He told me that as I was to be his sissy sub slut for the night I would be given instructions to follow prior to the meet and also for his arrival.
On the day of the meet, I checked into a hotel room and went to work on my make up, once I was happy with it I put on my wig. I then put on a black wet look padded bra and thong, slipped on some ultra shine black tights and finally put on a red tartan skirt and black pvc corset.
I sat on the bed and waited until finally there was a knock at the door. I opened it and was relieved that the guy standing there was the same guys from the pictures we had exchanged. He entered the room, setting a large suit case down on the bed and wasted no time getting to work.
A chair was placed in the centre of the room and I was handed a blindfold. ‘Put this on tightly’ he said ‘and no peeking’. I could hear him rustling around in his suitcase for a moment and then heard him place something on the chair behind me. ‘Right, I have placed a butt plug on the chair behind you. I want you to slowly work your way onto it’ he said. He had ‘kindly’ lubed the plug and I felt the coldness as I slowly lowered myself onto it... It seemed to go on forever but eventually I felt the familiar pop as it finally took its place and was now sat down, on the plug on the chair. I immediately hand my hands placed behind me and the chair and felt them being cuffed. These cuffs seemed rigid, not the flimsy kind you can get from a sex shop but the real deal. Next my legs were cuffed to the chair legs and finally my body tightly bound to the frame of the chair. I could feel myself becoming more and more aroused at the excitement of it all.
I sat there completely helpless and all I could hear was the sound of him taking items from the suitcase and plug sockets being switched on. Finally a bright light was shone a me which even through my blindfold was dazzling.... then there’s was silence.
Finally footsteps approached me and my blindfold was removed. As my eyes adjusted to the brightness I could see two large lights set up and a professional looking video camera in the centre.
I could see nothing but the lights...
Then he spoke ‘I can’t believe you don’t recognise me... although I have changed a lot since high school! Well I sure recognised you and I have never forgotten how you bullied me and lots of other people. I guess you were having to compensate for that tiny dick of yours’. I was stunned, shocked, he had looked familiar but not that familiar. ‘Well the tables are gonna be turning’ with that I started to feel the butt plug expand... just so you know, this is extra large, there is no way you are going to be able to get this out while it’s inflated... not that you can anyway as you so willingly allowed yourself to be tied to the chair!’ ‘I... I don’t know what to say... I’m sorry for what I did back then... I thought it was just a bit of fun’ is said... ‘it wasn’t fun for all your victims’ he said ‘and WE think you should be punished! Now I’m going down to the bar for a drink... you sit there like a good girl and enjoy yourself’. With that the plug inflated further, I felt it start to vibrate, and finally the door close...
To be continued...
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