JollyJohnnyP's blog post - Transgender School (a gay, tv & watersports fantasy)

My Mother had always wanted a girl and when I arrived, despite being a boy, she brought me up as a girl, even giving me a unisex name, Alex. She bought me pretty dresses, panties, girls' shoes and let my hair grow long. Of course, I didn't know any differently and made friends in the neighbourhood as a girl.

When I was old enough to go to school, she made sure that the school I attended wouldn't involve me in anything that required the display of my knickers. She always insisted that I wore two pairs of knickers, a tight pair of briefs to contain my little boy's bits under a much looser pair which didn't show the bulge and she impressed on me the importance of never letting anyone touch my knickers. So my early schooldays passed uneventfully with everyone thinking I was a girl and treating me accordingly.

At age 11, I had to move on from my primary school and now several potential problems arose, one was my voice breaking and the other was my developing interest in my 'boy bits' and, naturally, in what other children's underwear contained, and other children's interest in the contents of my knickers. However, Mother was very resourceful and during my last year at the primary school, she had searched for and found a boarding school which dealt exclusively with girly boys. Everything about "The Trevelyan Academy for Young Ladies" was designed to keep its pupils in no doubt as to their feminine roles in society, and their pupil intake was exclusively male. The boys who had male names were given girls' names and we were forbidden to do a wee-wee while standing.

The junior uniform was bottle green gymslip and cotton interlock knickers, white satin blouse, white stockings reaching just below the knee and black shoes. Unknown to us we were fed female hormones in our food, together with "antitestosterone" or "AT", a drug which neutralised some of the effects of testosterone such as the voice breaking. This meant we had no trouble passing as girls and later as young women. We naturally developed an awareness of sex as we entered our teens, especially when our breasts began to develop, thanks to the female hormones we were unwittingly taking. Also, the "AT" didn't prevent erections or the development of the male sex organs and so wet dreams were common and explained to us in our specially prepared sex education classes. We were told that we were a very special type of person, being both female and male but that with our breasts it was very difficult to pass as males which was why we were being brought up as females. It was also explained to us that females naturally were the target of male sexual interest and that we would be given practical experience in the sixth form of how to behave with males. We were told that if we preferred not to have sexual realtionships with males, that was fine and there would be no compulsion. This aroused our pubescent interest and it wasn't long before "practical experience" was a regular activity for some of us. I had a special friend, Jennifer, and she'd found out about anal sex on the internet and was fascinated by the idea. We discussed it and, not having any biological females around to experiment with, we decided to try it, the only question was who was to play the female role. We tossed (!) for it and I won (or lost, depending on viewpoint). Jenny was very excited and her penis rapidly stiffened, making a tent in her green knickers and making her arousal obvious as her gymslip was also showing a noticeable tenting.

This discussion had taken place during our leisure time while Jenny and I were out walking in the woods in the school grounds so we looked for and found a secluded spot to try out what we'd been talking about. Our only problem was lubrication but after taking off my knickers and lifting the skirt of my gymslip I looked round to see Jenny approaching me with her penis standing proud, leading the way, and her arousal was such that pre-cum was literally running out of her cock so I had no doubt that added lubrication would be unnecessary. I felt a dribble of warm pre-cum in the cleft between by bum cheeks before I experienced the thrill of Jenny's penis touching my anal rosette. She was very eager and I begged her to treat me gently. As she didn't want to hurt me, she reined in her enthusiasm and pushed very gently at my sphincter. I was pushing too and all of a sudden I felt my anus open and Jenny slid in with ease. There wasn't the slightest discomfort as she entered me, just the pure delight of being penetrated for the first time by a loving friend. Jenny started a thrusting motion and it was after only about five thrusts that Jenny uttered a long "Aaaaaaahhh" as she pushed into me as far as she could and her young testicles pumped spurt after spurt after spurt of fresh hot creamy semen deep inside me. I was close to coming too but held back because I wanted to return the favour Jenny had just done for me.

After Jenny had softened and pulled out, I told her it was her turn to receive my semen. She was very eager and removed her knickers before raising the skirt or her gymslip and turning her back to me. Although my pre-cum was significantly less in quantity than Jenny's had been, it was still more than adequate and to say Jenny was ready for me was an understatement. There was almost no resistance as my penis came into contact with her anus which opened like an automatic door and I slid into her until my pubes were touching her buttocks. As I began to gently fuck Jenny, I tried to think of other things to prolong the exquisite sensations that my penis was experiencing and which I knew would end with my ejaculation. I was reasonably successful in this and I managed twenty thrusting strokes before I was unable to hold back any longer and, like Jenny before me, I gave one final deep thrust up to the hilt as my cock exploded inside Jenny's rectum, disgorging the contents of my balls.

As I pulled out of Jenny, I felt a little pressure in my rectum and gave a gentle push, expecting a fart. It certainly was a fart but a very wet one in both sound and output as I subsequently felt Jenny's semen running down my left leg. I was very glad I hadn't got my knickers on as semen stains in the back of my knickers would have been difficult to explain to matron. Jenny had heard my wet fart and she suggested that we both try to expel as much semen from our arses as possible before putting our knickers back on. It must have been a strange sight to any onlooker (fortunately there were none) to see two girly boys squatting and periodically emitting wet farting noises as we pushed the semen out of our arseholes onto the ground.

We had both so enjoyed losing our virginities that there was no doubt about repeated excursions into the woods from then on to repeat the wonderful orgasms we had both experienced that first time. It was one hell of an improvement over wanking, which previously had been our only release.

The years passed and we moved into the sixth form at age 16. This entailed a change of uniform but this time it was a bottle green pleated skirt and white satin blouse over a white bra but under our skirts we could wear what we liked over our white suspender belt and black stockings. The school had an arrangement with a local lingerie shop run by a very understanding and helpful elderly lady. Groups of about six of us would be taken to the shop where we could feast our eyes on a vast range of knickers of many different styles and fabrics. Some of us preferred loose fitting silky knickers with thigh-length elasticated legs (which we were told were called directoire knickers) so that our cocks and balls would be caressed by the silky material with every movement. Others preferred tight panties that kept their wedding tackle under control and wouldn't show any tenting should an erection occur. The styles included briefs, French knickers (not very practical for hose of us with above average equipment) directoire knickers, panty girdles and thigh length tight panties, to name a few. Some of the girly boys even chose to stay with the bottle green cotton interlock knickers we'd worn up until now. Another alternative was double layered terry towelling knickers for those who either had an incontinence problem or, like Jenny, produced copious quantities of pre-cum when aroused. These had been available in our early years but it was considered embarrassing to have to wear them so they were always worn under a larger pair of the regulation knickers. But now they were considered a 'badge of honour' as anyone who produced enough pre-cum to need them was the envy of others. As I didn't have any particular favourite style or fabric, I chose a variety so that I could experience what they all felt like before deciding which was my favourite. I even included a pair of the 'nappy knickers' as I called the towelling briefs, and a pair of waterproof rubber knickers to go over them to guarantee that any wetness would be completely contained.

It was in the first term of the sixth form that the teachers started taking a sexual interest in us. The teachers in the upper school were all men, some of whom dressed in women's clothes. We were each allocated one of them as our personal tutor, the idea being that we could go to him to discuss personal problems or anything intimate. However, it was common for our personal tutors to explain all about the practicalities of sex, both homo and hetero, and to those of us willing to participate in homosexual activities, the tutor was very eager to demonstrate what this involved.

My tutor was Dr. Webster, a tall athletically built man who was particularly well endowed in the genital department. As it had been impossible to keep Jenny and my intimate relationship completely secret, we were both told that Dr. Webster had a large penis and that he tended to be allocated girly boys who had already gained practical experience in receiving anal penetration as they wouldn't find it as difficult to receive his endowment as would a virgin. I remember my first time with Dr. Webster. First he told me that he knew that Jenny and I had been intimate (at which I blushed) but that I needed to widen my experience and would it be acceptable for me to have sex with him. He emphasized that it was entirely up to me and that there would be no pressure to conform. I must admit that I had been intrigued by the rumours about Dr. Webster's cock size and was keen to find out if I could take him. I replied that I would welcome his attentions and when would be our first time. He told me to return that evening at 8 and to bring a nightdress as I would be staying overnight and sharing his bed.

I was a little nervous as I knocked on Dr. Webster's door just before 8 but I needn't have worried. He opened the door dressed in skintight long white lycra shorts (cycle shorts style) but very thin so that almost every detail of his cock, balls and bum could be seen in outline. On top he had an equally figure-hugging white lycra long sleeved teeshirt and again every detail of his body was clearly outlined. Once I was inside and the door was closed behind me, Dr. Webster hugged me and suggested that I remove my skirt; I followed his instructions and he complimented me on my white tight thigh-length panties which were very similar to his shorts except that mine were satin with about 8 cm of lace around the bottoms of the legs. He told me to join him on the sofa and he started chatting about human behaviour and interactions, sliding his hands up and down my satin clad thighs as he was talking, occasionally touching and even fondling my genitals. My response to his caresses was an ever growing erection which became quite uncomfortable so I had to reach down inside my panties to straighten out my penis which by now was oozing a little pre-cum. In response to Dr. Webster's suggestions, I returned the favour, stroking his thighs and genitals in much the same way as he was doing to me. Like me, he too was getting aroused and it was then that I saw why he had a reputation as a 'big man'. I thought his penis would never stop expanding and the bulge in his shorts was truly astonishing when he suggested we go to his bedroom. He asked me to remove my knickers and to get on the bed on all fours with my bottom towards him. He then lowered his shorts to reveal the true magnificence of his enormous penis which was about 7 cm in diameter (nearly 3 inches) and at least 25 cm long (10 inches). He knew that I would be worried by this huge weapon so he explained that the anus is very elastic but that he would let me stretch mine using a tapered butt plug before he inserted his penis and that if at any point I didn't want to proceed further I could stop and tell him I'd had enough. This was very reassuring and, although a little scared, I really wanted to feel that vast cylinder of flesh inside me.

Dr, Webster then went to a cupboard and returned with a large container of lubricant with a dispensing pump action nozzle and a large tapered butt plug which was comfortably small at the narrow end. He liberally applied the lubricant to both my anus where he used his finger to ensure the inside was well coated and to the butt plug which he suggested I should insert; that way I could stretch myself at my own pace and go as far as I wanted. I wanted to go all the way - at the thickest point, the plug was slightly larger in diameter than Dr. Webster's penis so I knew that if I could take it all, his penis shouldn't present any difficulty. It was very different inserting an inanimate object up my arse compared to the familiarity of Jenny's penis but it went in easily enough to start with and as I pushed it deeper I could feel my anus being stretched wider and wider. It began to feel uncomfortable so I eased off, withdrew the plug a little and then pushed it back in with a short fucking motion, pushing it a bit farther in with each thrust as my anus got used to the intruder. It must have taken me 10 minutes before I felt the widest point pass my anus which then contracted around the narrow neck of the plug. Dr. Webster had so enjoyed watching my progress that his erection was, if anything, even harder than before. When he saw he pushing hard to expel the plug, he took hold of the end and assisted me by gently pulling. Once again my anus stretched to the maximum diameter of the plug as it slid out and, before it could close completely I felt the warm moist tip of that huge penis pushing at my anus. It was still uncomfortable as my anus was again stretched wide open but it was a real feeling of triumph as I felt the monster slide in and in and in. It felt as if it were never going to stop but eventually the entire length was inside me and I hadn't uttered a murmur. Dr. Roberts asked if I were comfortable to which I replied "Yes" and then he started to fuck me, very slowly at first, periodically adding some lubricant, and then gradually increasing his pace as I got used to the monster piston inside me. We must have been fucking for half an hour before he started grunting and his thrusts became deeper and faster until with a final "Oooooooooh" he pushed all the way in and pumped an unbelievable quantity of semen into me. I begged him to stay inside me for as long as possible but it was barely a minute before I felt that huge sausage shrink and slide out of my very satisfied rectum. You may wonder how I know haw much semen was pumped into me that night - it will become clear as you read on. When Dr, Webster had withdrawn, he went to a chest of drawers and brought me a pair of nappy knickers and a pair of rubber knickers. He suggested I wear both as I was likely to leak in the night and he wanted to keep the bed dry! I removed my stockings and suspender belt before I put on the nappy knickers and was reminded of how pleasantly surprised I'd been when I'd first tried on my own pair at how comfortable they were. The wide well padded crotch felt particularly comforting as my balls and cock nestled down in it. The rubber knickers came next and I then took off my blouse and bra, put on my nightie and negligee and once more joined Dr. Webster on the sofa. While I had been changing, Dr. Webster had produced 6 bottles of beer and 2 tankards and suggested I might like a drink. I accepted his offer and enjoyed my first taste of Old Speckled Hen which later became one of my favourite beers. After the first bottle he suggested another and between us we downed the contents of all 6 bottles. It was then time for bed. We both climbed into the queen sized bed and Dr. Webster encouraged me to snuggle up to him with my head on his chest and my legs wrapped around one of his. I couldn't resist feeling his penis which even when flaccid was still well over a handful. It swelled slightly at my touch but we were both tired and after muttered "Goodnight"s, we drifted off to sleep.

I awoke at about 2:30 in the morning with my bladder demanding relief. Dr. Roberts was fast asleep and I didn't see how I could get out of bed, use the toilet and get back in again without waking him, which I didn't want to do. The urgency in my bladder was so great that I involuntarily let out a spurt. I had a moment of panic thinking that I'd wet the bed before I remembered that I was wearing the nappy knickers and the outer rubbers. It was then obvious that I didn't need to use the toilet at all; I could just do it in my knickers. This felt very naughty but I thought it was the best solution to my bladder problem. So I just relaxed and let the contents of my bladder pour out into my nappy knickers. I was astonished at how pleasurable it was, The warmth of the flood felt really good as it cascaded over my balls before being absorbed by the double layers of towelling and the feel of the warm wet towelling against my bum, balls and cock felt somehow comforting and soothing. It was while I was revelling in the delights of wet knickers that I became aware of a wet stickiness at the back and realised that Dr. Roberts had been right about my leaking during the night as it was his semen that had trickled out into the knickers, which had certainly "earned their keep" that night! I felt a slight pressure in my rectum and squeezed, expecting a fart, most likely a wet one, as on that memorable day when Jenny had taken my virginity, but instead a considerable quantity of liquid was squirted out, making the previous leak insignificant by comparison. Dr. Webster certainly knew what he was doing when he'd told me to wear the nappy knickers!

It was 8 o'clock when Dr. Webster gently shook me awake later that morning. It was a Saturday so there was no rush for classes, and we both showered before sharing a leisurely breakfast after which I put on my school uniform and went back to my room. It had certainly been a night to remember and I looked forward to many more semen injections from Dr. Webster's monster syringe!