A fictional story about a young lad that needs retraining. The island training centre. I was a bit of a tearaway lad, often getting up to mischief, just after my 16th birthday I borrowed my uncles car to go on a joy ride. My uncle saw me driving away and rang the police. I was caught and arrested, however the magistrate decided that rather than a prison sentence I was to be retrained and learn obedience. I was transported to a man made island that had once been a defence point in world war 2. The only way on or off was by boat. No helicopter pad. On arrival I was shown to the arrivals room where I was told to enter the shower area undress and shower using the supplied gel all over except my head and face. When I finished I noticed I no longer had any hair on my body only my head. I looked for my clothes but were nowhere to be found, I was instructed to wrap a towel around myself and enter the next room. In there was a matronly woman waiting, she told me to sit in a hair dressing chair and was then laid back over a basin. A strap was pulled across my chest and it clicked into place, a second strap was pulled over my thighs, I was secured, only my lower legs could move, I was strapped in. My hair was washed, conditioned then patted dry. Next the hair dresser rolled my hair and moved a large dryer over my head. Still strapped to the chair she switched it on and told me she would be back in 30 or so minutes. I sat trying to break free but the straps were too secure. The lady returned and removed the dryer the she removed the net cover and rollers, next she brushed my hair into a rather pleasant style. Next she shone an amazingly bright light over my face and chin. You will need a few more treatments, but after it will save you money by not having to shave. I wasn’t sure what she meant. When she had finished with the light, I was instructed to go through a door into the next room, where I was told there would be clothes put out ready for me to wear. “Where is my clothes.” I asked politely. I knew already not to be argumentative. “They are being cleaned and being made ready for your release”. She replied. I went into the next room and laid out on a table was a pair of bikini panties with matching camisole, a white blouse and black skirt. “I can’t wear these, I exclaimed, they are girls clothes”. I said. “It’s all you’ll get here unless you want to walk round naked.”. She told me. “Now I suggest you get dressed quickly, as it’s nearly time for lunch”. She added. I reluctantly dressed in the clothes provided, they really felt soft and sensual against my hairless skin. I followed the lady, who I found out later was called matron, to a dining hall. There were about a dozen other people stood in line by a serving hatch. And about 6 stern looking women watching them. I also noticed all the people were dressed similarly to me apart from colour of blouses. Two of them at the head of the queue were in flowery dresses and stockings or tights. We were all served our meal which was a healthy and given a protein shake to drink. What I wasn’t aware of at the time the protein shake was laced with female hormones. After the meal I was taken to administration, where I was informed of all the rules. No names were used, we were all known by numbers, I was 241. There was free access to all rooms except the administrative area. As I progressed through my sentence my blouse colour would change as each stage in my training would be reached and passed, approximately 3 to 4 months, eventually I would progress to the floral dress stage before my release back home. So I began my training by the end of the first week I noticed my hips seemed wider my pecs were tingling and my nipples grew hard under my camisole. After a fortnight my pecs were getting more pronounced into small breasts. After my first month I was given some training bras to wear. I also noticed when I showered and washed my developing breasts my cock stood to attention. Others also noticed, one of the other older inmates came to me and suggested we had a chat alone. She was number 38. I wrapped a towel around me over my young breasts and grabbed my lingerie. I was led back to her cell where we sat on her bed. Soon she had her arm around me telling me it was a natural progression with the hormones added to the protein shake. It would pass as my breasts developed further. Stopping the protein shakes now would have a really bad effect on me. As she was talking she was stroking my breast and soon I was making an obvious tent in the towel. So much so it had opened the towel and I was fully exposed to her. She reached down and took it in her hand and stroked me, causing me to erect even more. Suddenly she leant forward and slipped her mouth over my cock till her nose was pressing against me. OMG the intensity was overwhelming. She rubbed her thumb over my nipples while sucking me. The sensation was fantastic. I had never been sucked like this ever. I soon felt the feeling of impending cum. I told her I was about to come, and she sucked harder as I emptied myself into her mouth. When I finished pumping out my cum into her mouth she moved up and kissed me sliding his tongue between my lips, that’s when I tasted my own cum. Mmmm quite sweet in its own way. She broke the kiss and instructed me it was my turn now. I had never before been past kissing girls. Now I was being offered to perform oral sex on one. She stood and unclipped her skirt and slid the zip down. It dropped to the floor and before me was a sight I had only ever seen in a mail order catalogue. Tan stockings being held by white suspender straps and bikini lacy panties. Her bulge looked very inviting. Her bulge!!! She was also a he. She eased her panties down and her impressive cock hung, semi erect. I reached out for it and held it in my hands. It grew to full hardness, a little bigger than mine. She put her hand on the back of my head, but I didn’t need any encouragement to take her into my mouth. Bobbing my head up and down while caressing her nylon clad legs and suspender clips, I could hear her gasps as I brought her to her release. I automatically swallowed as much as I could as it pumped into my mouth, some leaked out onto her thighs. After she had finished filling my mouth and throat and I had swallowed it all, I licked up the spilt cum from her thighs. The total experience of being sucked and then sucking had been totally natural to me. What was my life becoming? As I continued with my training I became more and more feminine in my ways and was very accepting of my progression. As time went by oral sex between us became more frequent, until one day I was laying over my latest friend ,183, in a classic head to toe position when she started to press her finger against the rose bud of my hole, then she reached across to her bedside table and picked some hand lotion. Squeezing the tube she applied it liberally to my hole then inserted her finger next she inserted two fingers opening me up even more. All this time she was still paying lip service to my very erect cock as I did to hers. With her fingers in me and her lips sucking me I was extremely close to pumping my cream into her mouth. Then I felt the pressure against my hole as she tried to insert her rubber cock into me. What I didn’t know was she didn’t have a rubber cock, another girl had tiptoed into our room and had straddled her head and was pushing herself into me. Oh wow the pressure as she pushed through entering me. Then she stopped, the pain subsided, then she pushed further into me until I could feel her tummy touching my bum cheeks. Slowly she started moving in and out. Gradually building up speed and my pleasure, my other girl was still sucking me as I was her. Then the girl who had just taken my cherry clasped my hips and thrust herself fully into me and I could feel her spasm as she emptied herself into me. “Thank you sweetheart for letting me be your double first”. She said. It was the same girl who had given me my first oral sex number 38. It had been 12 months since I first arrived and I had become more adept at dressing, choosing matching outfits and makeup. I hadn’t argued with anyone or felt the need to. I was calm all the time. After another 6 months I was summoned to the admin office, I was informed I could now choose to wear stockings and suspender belt or basque style corsets or tights, ( pantyhose). I asked could I have the option of both as some days I felt that stockings etc would suit my mood better, I also admitted they did feel fantastic on other girls. I was granted 1 month of tights then 1 month supply of stockings etc. Then I could make my final decision. At the end of 2 months, my choice was made. Stockings. I was taken to the stores where I was issued with 4 suspender belts two black 2 white, 12 pairs stockings various shades and two basques one white with pretty blue bows and the other black with bright red bows. My next six months were spent in continuing the training. At the end of my two years in this training centre and several enjoyable sexual sessions with other trainees. The administration staff made no advances on me sexually. I was informed I would be returned to the main land. A new identity had been arranged by the magistrate who had sent me to this man made island. I was told to pack all the clothes and lingerie in a provided suitcase and I would be delivered to a mainline railway station with a ticket to my final destination. I had 8 hours to arrive there, or a warrant would be issued for my arrest, as I was now old enough I would be sent to a male prison wearing my lingerie and a dress. Not ideal in fact, Positively scary. I did of course arrive on time and was settled into my new hostel. I was given a list of employers that were seeking staff. After Brexit, Britain’s businesses were booming the economy was running at an all time high. The three major political parties were in total agreement. European Parliament was crumbling as more countries sought to leave. I secured employment as a PA to a wonderful boss, who I later discovered had also served two years on the concrete island. We now work closely together and even closer at home since I moved out of the hostel and into her home. Some Weekends we shop together buying some wonderful dresses and very erotic lingerie to wear and tease each other. It’s a wonderful life living as I do in my feminine guise. If you ever get caught breaking the law, 2 years on the island will change your life for the better. Carole. XXX