My Passage to Womanhood, Volume 1

Chapter One

Chapter OneInitiation & Sexuality

It is true that I grew up in a family dominated by women. I had an emotionally remote mother who was a single-child herself and besotted with her image and evening life, and four younger sisters; I still remain close to my eldest sister today. My father was always travelling with his work and, when at home, he was pre-occupied with his charity work and clubs, so he was always out in the evenings and weekends. He was a caring Dad though and a lot of fun when he had free time.

Overall, I must say that, despite some limitations, it was a good childhood I experienced. By the age of eight, I was shipped off to what is known as a Prep School in the United Kingdom, a preparatory school to get kids, from eight to thirteen years old, up to passing a horrendous series of exams known as Common Entrance to enter our Public School system.

To freak our American readers out, in true Brit form, a Public School is, in fact, a private school; the reason for this is that, for many of the older schools dating back to Mediaeval and Renaissance Age origins, they were schools for the then middle class children. To raise some additional funds for maintenance and continuity they said regular prayers to the dead in return for fees, hence a service to the “Public.” Sometimes they are referred to as “Chantry Schools.”

Less of this history lesson though, and more about me, as I am sure that you do not want a potted narration of English schooling systems. However, my prep school was fun; I was bright intellectually and quickly made my way through the years to spend some three years in the top form.

Sports-wise I was, I guess, average though I did show a good proficiency at cricket and golf, the latter of which was to stay with me. I had lots of friends and there was all the exuberance of youth as we had huge, dense woods to explore and set up tribes with their huts and forts.

Like all eleven to thirteen year old boys, our hormones went on the rampage and there were always various “romances.” Even though the school was technically a mixed one, the boarding element of it was all boys. This led to some play in these huts or in each other’s beds. I can remember such playing with a friend, Richard, cuddled in bed together in our jim-jams, as the Second Master read us a story, “The Silver Sword” by Jonathan Cape.

Richard, who was twelve, had a lovely, small, pencil-like c**k with a long foreskin that I played with frequently, and he with mine. We even got to exploring each other orally and I enjoyed taking his erect p***s into my mouth and playing with his head.

However, and I don’t like to really mention this but I guess I should as it may have had some psychological impact on me, one night, in our dormitory, a man climbed into bed alongside me.

I felt his large, hard c**k up rubbing against my pyjama-ed bottom. I can not remember him cumming over me or into the bed sheets but I was certainly petrified and numb, just his hard c**k pressing against my bottom, between my cheeks, towards my anus, but not in it.

Only recently have I accepted what happened.

Whether it had anything to do with what was to happen I do not know, certainly I do not think it has affected my sexuality but maybe it influenced my want to be a bottom and submissive.

The intruder was probably the Second Master as, shortly afterwards, three of us went to the Headmaster about him after he had taken indecent pictures of one of my other friends, another Richard, who I got to know more intimately late in my time at the school.

He had lured him down to the garages and had my friend strip off for a photography session. The Master was immediately fired; in today’s world he likely would have been in prison. Our reward was an advanced s*x educational lesson and the three of us were made prefects the following term.

My first true experience and the loss of half of my ‘virginity’ occurred three years later at my public school.

Now this was a true Public School, boys only, full of daft and weird ancient customs and traditions, boarding in houses of sixty to eighty supervised by a Housemaster and his wife, along with a tutor.

While the school never had a major academic reputation, it has had its fair share of scholars to Oxford and Cambridge and many of the Old Boys have gone onto major leadership roles in business, religion, politics and diplomacy. There have also been a number of “artists” and a substantial number of sportsmen. However, it was considered as one of Britain’s major schools.

I was in my last year though, technically, I should have been in the year behind as I was one of the youngest of my year; my Dad had got the timing of my “going up” spot on and I was in a better group as to the way we cohered together.

I had progressed to being Head Boy of House for my University scholarship candidacy and, de facto, a School Prefect; this gave me considerable freedom to free-time activities as well as who I shared a study with as I controlled the study and dormitory allocations.

John was from the year before that, but there was only a few months age difference between us. He was about the same size as me, five-foot seven, quite olive skinned dark haired, slender, and a suggestive tad effeminate as he regularly ran his hand through his thick hair. He lived at some distance from the school.

He was a wonderful cricketer, a superb slow spin bowler and had joined me on the 1st Eleven. So there was a basis for our natural friendship despite the perceived “Year” difference. We regularly had shared practising the game together and also this extended to other sports such as rugby, both being ‘backs’ at that sport being amongst the sprinters and kickers of the team.

Our privileges, with me being a School Prefect and both of us as 1st Eleven, allowed us to practice as we wish and avoid the compulsory run that befell anybody not on formal sports on any given day. This also meant that we had the opportunity for long chats and gossips.

John’s year had a reputation for a lot more “s****l activity” than my year.

There were two boys in my house that were known to be indulging in each other and John himself carried a reputation, largely because of his attractiveness and feminine ways. I had never seen anything directly evident up to the point I now come to, but I would own up to having a crush on him for some considerable time.

Life was to advance” big time” one day after heading back to the House following a sports practice session.

The House was still quiet and we had the advantage of being first into the bathroom section. Now this will gross some of you out, but it seemed that we were still living in ‘primitive,’ Victorian times. True, cold baths and showers had gone out of the window, but bathing was still communal.

Five baths for the juniors and middle school and then three for the seniors with a large washbasin area separating the two areas; two people to a bath and copious amounts of water over the side and refilled, which kind of kept the water a pale muddy colour, especially after rugby. As the formal games came in, it would be chaos in there.

To share a bath was nothing strange, so we ran it and disappeared into the changing area. This was hierarchically arranged, the Head Boy having a very quiet area, then fellow House Prefects in descending order of seniority and so on, right down to the newest of the new.

John and I stripped down out of our cricket whites, donned towels and went into the bathroom area. Into the bath and we started chatting about something; I can not remember what but it was something obliquely sexually related as something got us going. I do remember though getting out of the bath, drying off and heading back to my changing area. No other boy had returned from his activity.

John appeared from around the corner and sat down near me; he was just in his towel and carried on chatting. Somehow, he managed to dislodge his bath towel and I could not but help notice his c**k that had already nicely hardened.

Now we had seen each other enough times but this was the first time I had seen him so stiff; really, it was the first time I had seen any of the boys that hard. He was pretty big, dark and he had a very nice head to him.

His hand came over and onto my c**k, mentioning that he had fancied being with me for some time and whether I minded.

I let him continue and he took my hand and placed it on his now throbbing member. It did feel good though. John took the lead and cuddled up towards me, moving forward to kiss me, his tongue probing my lips and I allowed him into my mouth.

I could feel myself hardening but this wasn’t the place as, even though it was the most secluded and quiet place in the room, there was still a risk of being spotted.

I suggested my study as I had single occupancy of that. I had had to evict an old friend of mine who had been a prefect as he had, stupidly so, been caught smoking. This was one of those cardinal sins that beset schools at that time.

So, we quickly dressed and headed over to my room and the privacy it offered us.

Once inside, John continued his kissing of me, pulling me towards him, and feeling me in my trousers. I could sense his size and went to release him.

Soon we were out of our trousers and underpants and I pushed him back onto my couch so that I could go down on him and take him deep into my mouth.

He filled me with his seven plus pulsating inches and I let him begin to f**k me orally. He didn’t last long and for the first time in my life, I experienced the saltiness of sperm, flooding me, exciting me, and pushing me to a new sensual height.

John moved me over on the couch and went down on me. I was smaller, with just a tad less than six inches but I have always had a reasonable girth. Quickly, I was turned on too; the tension and excitement surged through me and I released myself into John’s waiting mouth. He moved to kiss me, intermingling the taste of our c*m.

Over the rest of the term, which did not have that much to run, we were inseparable.

I admitted to a fetish to him and he played along with me; I had always had a ‘weakness’ for wearing the pyjamas of those that I had fancied and, preferably, once they had worn them so I could sense their odour. I would sneak into the respective dormitory and borrow them, then change in the toilet blocks and wank myself off.

I let on that I had borrowed John’s several times over the years, as he was one of my favourites to think about and wank myself off on, and how I loved his odour.

From then on, John would wear his for me and, weekly, he would pass them on so I could wear them for the following week. He had favourite yellow striped ones that I loved being in, and then blue ones and maroon ones, both with white piping and a soft silky “nylon-esque” fabric, which I also adored the feel of.

I got a big charge out of knowing that he was “close” to me with his scent and all the rest as to where his body had been, and the residue of any c*m etc., on them.

John then extended this “wear and loan” to his underpants, psychologically and subconsciously, I guess, making me his property. My bottom, c**k and balls were sitting next to where he had been, a continual reminder of him to me.

You will see that this dimension of me was to grow and feature heavily in my submission to my future partners as my life progressed. Body odour and particularly s****l scents have always been an integral part of my “turn-ons.”

Our next major experience came in the school holidays.

John lived over a hundred miles away from me in the depths of Yorkshire. His parents decided to go away on vacation by themselves, and his elder sister was also away travelling on her “gap year.” So, I was invited down to stay with John, the logic being to keep him company and given that we were responsible, bearing in mind the position that I held at the school, we could live by ourselves. There was a housekeeper who came in to prepare meals and to ensure the house was clean and proper.

The first thing we did when we had a moments privacy was to kiss and, before we headed out with his parents for some dinner, John produced a pair of his used underpants for me to get into and feel that more comfortable in being in his control.

That night, we slept together for the whole night, the first time we had been able to do so; our s*x was mainly oral and in m**********g each other. The following day, John’s parents departed and, once dinner was over and the housekeeper had departed, we were truly alone.

I forget what we did that evening but it was in and around the house. As the evening wore on we became more exploratory and tactile with each other. John started teasing me about taking me, breaking our virginities.

To that end, he suggested that I should, perhaps, be more girlie for him. I looked at him somewhat perplexed and he explained that he thought I should wear some feminine clothing to help my look, to be his special girl..

Despite expressing some misgivings about being discovered, he calmed me down by saying that we were alone and there was absolutely no risk of anybody disturbing us.

Given my sensual side, I was not amiss to the idea and went along with his play.

The long and short of it was that we ended up going into his sister’s bedroom and to her lingerie drawers to see what she had that I could be dressed in. John soon zoomed in on a white lacy bra, matching bikini style panties and a suspender belt, followed by finding some black stockings. They were the brand “Warners,” well respected as a leading maker back then.

John also pulled out of one her medium length white nighties for me.

I can remember him saying, “Here we are, change into them and you can be my girlfriend for this visit if you enjoy the feeling.”

He left me to change into the soft, sexy and alluring feminine items, the very transition of becoming what I am today, a woman.

Now I haven’t mentioned anything about myself. Back then I was five foot seven, weighed around sixty kilos and was fairly slender with a thirty-four inch chest. My hair was a coppery colour, face was freckled and with greyish green eyes.

I slipped out of my outer clothing and felt the lingerie in my hands, probably as I was still rather nervous about this. Its touch was so soft, sensual and sexy to me. I slipped into his sister’s bra by putting it on backwards, attaching it from the front onto the little u-clips, before turning it around and slipping my arms through the straps. I chose some of her panties to act as padding of the cups.

The suspender belt went on next and I rolled on my stockings, thanking myself for having a female family so I knew roughly how to do it in rolling the stocking up before putting my toes into it and unravelling it up my legs. I attached them to the garters and this started to feel sensual and very different, especially with the garters gently pulling on their hosiery partners.

And then came the panties. I stepped into them and pulled them up into position. I was transfixed and hooked for life with the feeling, and with the implication that I was “female.”

This was driven by the feeling of the soft material against my skin, the sight of the lace and smooth, ribboned front panel holding me in and, finally, the deep meaning of the gusset up against my perineum, knowing what that soft material normally held.

I slipped into the final item, the nightie, and it felt wonderful.

This was such a new and highly stimulating feeling and that I was to play the role of girlfriend to my young man, John, who was waiting for me. I took one of his sister’s brushes and ran it through my thick hair, sweeping it outwards. I also managed to find her perfume and sprayed myself with that.

Nervously, I left the room and headed down the corridor to John’s room.

John was already in bed, so I climbed in alongside him and cuddled in.

He was already ‘wowing’ me over how I looked and just how sexy I was.

He moved close to me and was soon exploring me with his mouth, gently kissing me, and working me up into an excited, stimulated state. His hands roamed over me, feeling me in my girlie envelope, seeking out his object of desire and playing his light fingers over the front of the panties to tease me to full hardness.

His hand slipped in side and I moaned with the pleasure of his touch. He caressed and gently frotted me, slowly building me up further.

His fingers moved down my love area and under to find what was to become my gurl p***y, touching me softly, stroking me, then letting a finger play over the entrance, and, finally, to insert it into me.

It felt a little weird but my muscles relaxed around him and he pushed it a little further in.

He moved down my body and edged my panties aside to take me in his mouth.

His mouth felt good as his tongue rolled around my head, taking in my stiffness.

I wanted to return the compliment or, more importantly, to have him in my mouth too.

I suggested that we moved into a sixty-nine and John adjusted himself around so that I could enjoy him, his dark musty c**k rapidly filling my mouth and allowing me to taste his pre-c*m.

I just so loved pleasing him in this manner and to feel him surge deep into my throat.

This was not to be though.

John pulled out of me and turned around.

He took my panties down, removed them from me and then turned me over, pushing my nightie up off my well-proportioned bottom. He slid a couple of his pillows under my tummy and had me lie on them face down, thereby presenting my derriere for his pleasure.

His fingers roamed over my globes and up and down my valley mercilessly probing my anus, preparing me for his eventual taking of me. He took a little lubricant gel and applied it to my rosebud; this made me open up that more for his invading digits and they were feeling so good in my “home.”

I felt John move up my back and his hard, throbbing c**k at my gurl-entrance.

He smoothly pushed at me and, tenderly so, I ceded to him, my entrance ring easing to accept his wanting snake into me. I grimaced a little, but all his foreplay paid off and John was able to slide into me easily.

God, he felt wonderful in there, filling himself deep into me and pressurising my gurl g-spot. This is what I needed, to be feminine and f****d like a girl.

He started to f**k me at a light rhythm, letting me relax and rock to his pace, allowing me to press my bottom back onto him and prevent him from sliding out of me.

He held my bottom tightly with his hands but, as his momentum gained and my rocking strengthened, he took hold of my shoulders and I could sense his chest across my back.

I was feeling so hot and excited and the next thing I felt was him ejaculating his love juice deep into me. I came just behind, a mind-blowing orgasm and, at that time, one of the strongest of my young life.

I look back with affection on this, as it was a wonderful way to be taken for the first time.

Another boyfriend was later to say, “that once you have had a hard c**k deep in you, you will always cherish one.” It is true; but that first c**k, John’s lovely weapon, has always held a special memory for life in my brain.

The stay was a huge amount of fun, watching cricket in the daytime and even playing two games, as well as our exploration of each other with all the time and space that we had to do so.

His sister’s lingerie got well used but I was pretty handy at getting it washed, dried and pressed. Too soon it was all over and his parents returned, but it set a strong foundation for a discreet but torrid relationship that we managed to have back at school, with the advantage of John sharing my study the following term.