I have been a transvestite for more years than I care to think about, always in secret, never divulging my desires to anyone – not even my closest friends or family, for fear of the ridicule that would happen.
Back in the eighties, I used to order clothes from catalogues or buy them from local charity shops and wear them around the large detached house that I shared with 3 other students in the southern English city where I was a studying for a degree, but only when I was on my own (when the others were away) ….… occasionally venturing out on to the patio in the dead of night …. Where I used to “relieve” myself !!
I had “discovered” bondage and was trying a few devices that I had had delivered – including a pair of leather handcuffs, a leather neck collar and leg restraints.
It was one summer Friday late, afternoon, that I decided to go the whole hog. My fellow students were away for the whole week, on a field trip.
I had 10 full days to enjoy myself.
I dressed up in my new, PVC French maid uniform, with multi-layers of net, tutu petticoats, this fluffed out the extremely short PVC skirt to almost horizonal, complete with locked on 4 1/2 inch heel ankle boots, stockings and suspenders and applied make up as normal.
I then glued on my blonde bob wig.
I must have looked a real tart, but I felt sexy and good looking.
I then started on the bondage. I fitted a restraint collar around my neck and a 12inch chain was padlocked to the cuffs on my ankles. This only allowed me to take mincing steps.
I then fitted a small and tight penis ring and long, fat dildo, stuffed into my anus – which felt REALLY good !
I finished the whole ensemble off with a large 3 1/2inch ring gag in my mouth, this mean that my mouth was jacked wide open and with a wide leather strap tightened around the back of my head, I tightened up the buckle behind my head, finally locking the cuffs round my wrists to loops on the collar. There was absolutely no way that I was getting out of this.
I sat down on the sofa, luxuriating in the feeling of pressure in my anus and the feeling of not being able to escape and the image of what I saw in the big mirror on the wall of tart in tarts clothing made me want to cum on the spot. Luckily, the penis ring prevented thus from happening.
I had hung the key on a hook in the hallway. But the key on the hook, fell off and down a crack by the skirting board, through the floor boards.
I knew that I was in trouble!
I tried without any luck to release my wrists from the collar, but eventually fell down onto the living room floor in total exhaustion.
I lay on the floor for about 6 hours, until it was dark outside and wriggled my way to the foot of the stairs where I managed to sit myself upright and this allowed me to get my mind clear over what I would have to do to escape from my bonds.
We had a phone but it was upstairs in my bedroom on the second floor and there was no way that I was going to make it up 2 flights of stairs restrained as I was and who was I going to call anyway ?
I had seen a few attractive girls going through next door, since the old lady who lived there, when I moved in, just over a year ago had been moved to an old persons home and the property had been sold, and assumed that it was being rented to students.
I got my mind around what I had to do …..
I didn’t want anyone to see me in my predicament, but also knew that there was no alternative, except starving to death. So I squirmed to the front door and pulled it inwards to get it fully open. I then squirmed out on to the pavement. The cool, fresh air hit my balls and made me shiver. I continued to squirm my way about 50 yards along the base of the wall in front of the houses trying to stay out of the direct light from the nearby street light and after 20 minutes had manoeuvred myself into the porch where I hit the bottom of the wooden front door with my forehead several times.
The door opened inwards and I looked up and saw, what looked to me like a schoolgirl in an extremely short black dress with her hair in pigtails, she was wearing stockings and, even more surprising, extremely high heeled ankle boots.
I tried to say “Is your mum at home” but it came out “Mumff, Gurgle, Mumff” due to the ring gag that was in my mouth.
She looked down at me and almost pitifully and said “What do we have here?”
She realised that I was a male and called another woman, who quickly appeared on the scene, telling me “not to run away” which was the last thing that I was capable of doing at that time !!
So there I was in an extremely vulnerable position, dressed in the most embarrassing outfit possible, restrained, with leather straps and chains, with a large dildo embedded up my arse and a ring gag in my mouth, lying in a strangers doorway. What else could go wrong for me ?
The older woman, who went in to the front room, momentarily, returned and took one look at me and started to laugh “You’ve got yourself in a predicament” she said “What should we do with you ?”
The younger girl, who I later, discovered was called Jackie, said “Can I have him, please ?”
I, of course, started to get extremely excited by what was happening to me, my penis got hard….
Jackie dragged me to the bottom of the stairs where I was able to sit up and have a better look at my surroundings.
I was still unable to move my arms or hands, since I still had the neck collar with my wrists securely locked to it – and my ankles were still fixed together with a short length of chain..
What I saw in the first room, shocked and scared me, but also excited me. A large built, black man was strapped with wide leather straps round his wrists, ankles and waist to a St Andrews cross, he was slightly older than I was, and totally nude and obviously impaled on a large dildo.. He was writhing around trying to get comfortable, but the older woman was holding a cat of nine tails in her hand and was whipping him, repeatedly…… around his absolutely massive penis and balls.
His penis was “ringed” with, what looked like a 3 inch diameter penis ring, to prevent him from cumming. This did not prevent him from having a raging erection though.
My anus was emptied of its obstruction by Jackie and the two women helped me to my feet and half dragged me, half carried me to the cross.
The ring was removed from my penis and a condom was fitted over it.
A wide leather belt was strapped around me, pulling me tightly against my fellow “detainee”, his huge penis had a condom fitted over it, it was then pushed deeply into my anus, breaking through my sphincter after a thrust and I could clearly feel it throbbing.
The chap behind me soon came with a loud grunt, and I too had followed suit, several times.
This was a totally new experience for me. I had never even seen another fully grown nude man before and here I was being impaled by a mans cock !!!
I would say that I found the experience unpleasant, but that would be a lie …. whilst it hurt me a lot …. it was a nice kind of hurt … the kind that takes you elsewhere …. floating on clouds perhaps ….
I was finally released from my straps and chains and then awaited my next new experience and after a shower in which I was rinsed down Jackie.
I was dressed as a schoolgirl in stockings attached to a basque, an extremely short black pleated skirt and white blouse and hooker heels and sat down at a desk and make up was professionally applied to my face and lips, and my wig was refitted. I looked and felt extremely feminine and that was was just right as far as I was concerned.
I stayed dressed as a schoolgirl for the rest of the week, doing minor chores for my new friends and this was the start of a new life for me.

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