• The story which you are about to read may, at times, may seem quite preposterous. I have often wished that it was an episode of a nightmare or something, but I assure you that it is not. In fact it is probably true that I am enjoying my new life.? I have done so on the explicit instructions of my mistress's who hopes that in the recounting of my life story, that in the process of the telling of my story that I may come to more fully realise how happy I am at being able to satisfy and accept what I am, her slave-girl with benefits.
Please note I use a mixture of English spellings as per the Oxford English Dictionary, plus a few American spellings by courtesy of my spell check.
It all started just after my fourteenth birthday I was quite slim and small for my age but quite fit. My widowed mother doted on me and she really ensured that I had the best of everything. I think she secretly wished that I had been born a girl, and at the time I remember her looking in girls clothes shops and saying 'Wouldn't that look lovely on you, and sighing to herself."
But I was no sissy and although I was small for my age. I soon discovered that nature had endowed me with a cock that was rather out of proportion. The fact that we had to change in the school dressing room after sports brought my freaky cock to general notice. In fact many boys started referring to me as 'Donkey Dick' and I think that started the situation where I became the target for some of the more free wheeling girls at the school. After hearing me referred to in that manner the girls soon cottoned on to the fact that I had something special to offer.
My first sexual experience came when I was employed to wash the neighbours two cars It was a long job and the lady of the house told me that they would be out for most of that day shopping, but their daughter Judy was still at home in case of problems. They had not been gone long when the door opened and suddenly, in walks in a Judy their cute daughter. I knew Judy quite well, but this morning she looked as though she had taken a lot of extra care with her appearance. I knew her only in school uniform but today she was wearing some make up which was unusual, and she looked especially lovely in stone washed blue jeans and a very tight dazzling white blouse. I knew she was about the same age as me. She was very cute for her age and acted in a very cute almost babyish manner at times.
I had never really had much to do with her at school, but rumour had it that she had one or two current boyfriends on the go. Her blouse that morning was so tight that her breasts were pushing the cotton fabric out and her nipples could be clearly seen through the fabric of the blouse and it was so obvious she was not wearing a bra. I suspected her mother would object if she saw her dressed like that. I was no fool and I suspected that she had dressed as she had because she had an ulterior motive in coming to see me.
We got to talking as I carried on working, and pretty soon she popped out with the question "Why do the boys call you 'donkey dick' Tony?"
For a second I was a bit embarrassed and this seemed obvious proof that she had much more than a casual chat on her mind.
I replied "Can't you guess?"
She grinned and said "Yes, but pretty please, will you to show it to me."
"You are joking?" I asked.
"No Tony. I really want to see it for myself."
So, deciding that if that was what she really wanted I would certainly oblige and see where it was leading to, so I closed and locked the garage doors and I moved to stand in front of her.
"You will have to fetch it out of my pants as my hands are dirty." I told her. She was not in any way shy, as she just undid my belt and pushed my jeans and my underpants down to the floor. By this time I was really hard made very much worse as she let out a little gasp of delight and took into her small cool hands to fondle.
"Wow you are about twice as big as my boyfriend."
Then she said, kind of breathlessly, "You don't have a girlfriend do you Tony?"
"Not at the minute I told her, as I leaned down keeping my dirty hands away from her clothing and kissed her softly on the lips.
"Interested " I asked.
"You bet." She replied.
Then she pushed me away as she took my arm and pulled me across to the water tap and said "Lets wash your hands Tony I don't want dirt all over me when you fuck me. Tony?"
I quickly washed my hands not quite believing what was happening, then I slipped one hand inside the top of her jeans and massaged her teen aged tummy. Her arms came round, my neck as with the other hand I undid the buttons on her blouse, her boobs although not fully grown popped out into the open and I lightly cupped one in my hand, gently flicking the nipples. I leaned in toward her and for a minute or so, we kissed, our lips clung together, tasting each other's breath. Then she leaned forward and kissed me, much harder with a mouth-open, French kiss. Her breathing was getting faster and shorter. By now I was feeling pretty bold as she had made all the running...
So I started undoing the fastening on her jeans, first undoing the fastening at the top. As her jeans unzipped themselves in answer to my hand's pressure, I pushed them down to the floor for her to step out of them and then. I slipped my hand inside her panties and found a small patch of hair on her mound. She repeated the undressing process on me and soon we were standing naked and kissing our naked bodies clinging together. My rampant cock slipping between her lugs to rub freely against her warm wet pussy.
Then taking my hand she led me to a camping mattress already inflated leaning against the all and placed it on the floor so that we could both lay down on it. Following what I had learned from porno films I was soon licking away at her pussy. My tongue was eagerly kissing her teenage cunt lips with enthusiasm and eagerly searching for her clit and soon she was writhing and moaning as my tongue did its work very much to her satisfaction, and I was soon inhaling the scent of tender, sweet young pussy musk, surely the most wonderful scent in the world at least to me at the time.
She was moaning and wiggling around a lot and making a lot of noise to stroke her little cunt lips, and swirl around her bud. She loved it, repeating "Yes, yes, yes!" over and over as she started to have little orgasms and her juices were beginning to flow over my face I encouraged it, as I continued to probe inside her pussy with my tongue, squeezing her little ass cheeks in my hands.
My cock was now hard as a rock, and soon she was pleading with me to "put it in." So I moved and pressed my cock gently against her pussy lips. She was breathing into my mouth, her tongue was playing with mine, She took my cock into her hand and pushed me just inside her pussy lips She was dripping wet there, panting hard now. I rose up a little on my knees and continued to push, it took a little time as I slipped into her very young girl's pussy bareback ... It was like an electric shock for both of us as I sank all the way into her. I felt a big thrill up my spine as our flesh and juices mingled, giving us their full effect.
She was no virgin, but she was very tight, and from her groans I guessed that I was the biggest she had ever experienced. But both of us were wet with our juices so it went smoothly. I grasped her little butt and fucked into her slowly, pulling out just as slow so the head of my cock would scrape the tender, sensitive insides of her tight little channel.
Slowly, several times I did this, and then I picked up speed, beginning to fuck her faster and faster ... then I slowed down again, grinding around deep inside her, my balls pressing against her young butt cheeks, her back arched hard against me.
That movement felt so good that I could feel my seed, move in waves along the way, up from my balls and through my cock and then spurting inside her sweet young pussy- unprotected, my cock so deep inside her I could feel the pressure on my balls as she, too,
came, her little ass cheeks pumping against me, moaning into my shoulder, heels pounding on my ass.
It was a wonderful debut to the world of raw sex for me ... But it wasn't the last we shared. She was insatiable, that morning she helped me finish my work so that we could move into her bedroom. I later heard that she had dumped her boyfriend, and for a time she became mine exclusively until her family moved away. But by that time my attentions were beginning to be taken elsewhere.
That was the beginning of my sexual education, but shortly after this incident I became very aware of one of our new neighbour a Mrs Barbara Watts a well known clinical psychiatrist who had become very friendly with my mother. She was about 35, a tall slim blonde who I gathered was childless, and who had inherited quite a fortune from her divorced husband. I later found that she ran a secure home for well off female sex offenders. I thought she was lovely, and my interest in Judy quickly began to wane. Barbara became very friendly with my mother and increasingly she encouraged me to spend more and more time with her.
My conversations with Barbara became more and more intimate as time went on. But I found Barbara absolutely enchanting, but now in hindsight I realise that her approach to me sexually was quite well thought out and well planned.
Increasingly my interest in younger girls waned, and increasingly under Barbara's influence I became more conscious of the older women around me, for instance some of the younger teachers at school began to interest me sexually. On one occasion I tried flirting with our 28 year old Arts teacher, but soon found myself firmly rebuffed. But increasingly I soon found that I wanted to spend all of my spare time with Barbara. I was now very sexually attracted to her, and to some extent other older women. With Barbara's encouragement I hid a lot of the time I spent with Barbara from my mother, so that she would not get suspicious, and then to my dismay my mother was suddenly taken ill. She, had a very short illness in hospital and passed away. I was of course grief stricken, but Barbara was there to console me. Apparently when Barbara visited my mother she had got her to sign a paper putting me into her custody if she died.
Having no close relatives Barbara quickly had her lawyer arrange for the courts to agree for me to be fostered by Barbara, and then this was quickly followed some weeks later by a proper legal adoption. I had moved in to live with Barbara from the day my mother went into hospital.
But from the very first night with her she insisted that I slept with her. Her explanation was that I must be worried over mother and I was now in a strange house, and she wanted to be there to comfort me. I did not object in fact I was very pleased at her insistence. That first night I thought I had offended her because she was very quiet, but after dinner we had a few drinks, and she insisted that a few glasses of wine would not go amiss for me as it was a special occasion, and then Barbara suddenly said.
"Why don't we have a shower and get ready for bed Tony. We can watch TV afterwards or perhaps you might like to watch a video?"
I had just got in the shower and started to wash myself, when I was suddenly joined by a very naked Barbara, wearing a shower cap, who boldly said.
"Move over Tony dear let Babs wash you." and she started to wash me just like my mother had used to when I was much younger. I was a bit embarrassed at first and gave a little protest, but then I realised that Barbara seemed to spend a lot more time washing my groin and my now very erect cock than was necessary, which without much trouble she had succeeded in getting me quite hard. then taking me by surprise she knelt down and took my cock in her mouth until I came in long spurts into her mouth.
Then she placed one arm around my shoulder and at the same she pulled me close against her ample breasts and started kissed me on the mouth. I was not objecting in fact I found myself responding avidly
"Ooh. darling" She said. You are very big for your age. I hope you don't mind me making a fuss of you like this, and teaching you how to please me as a woman."
And then she put her hand down and slipped my cock between her legs where it rubbed very sensuously against her smoothly shaven pussy. Then she started kissing me again on the mouth. I did not mind in fact I thought this was great, this was my wildest dream coming true and I started to respond. I took her I my arms and then she said.
"Lets dry ourselves honey and go and watch some TV."
I must admit that I was a little disappointed, but that was the night I realised later that Barbara had begun my training to become what many would term a male whore. Soon we were sitting on the couch with her wearing a thin house coat, and me with just my dressing gown. However, the TV she decided we should watch was some very instructive porn films and they all seemed to be about boys my age having sex with slightly older women and girls. then we had two films about boys who liked dressing as girls. According to the films they seemed to like the experience.
As we watched the video she put her arms round me and pulled me close by now I had got the message that Barbara had carnal thoughts where I was concerned, and my cock was rearing up and ready for action. She slipped one hand under my dressing gown and gently fondled my cock while she encouraged me to suckle her nipples.
Suddenly she switched the TV off and taking my hand and without speaking she took me up to her bedroom. In the bedroom she stripped off her house coat and had me take off my dressing gown and she put her arms round me and said. "Tony let us pretend that today I have just become your lovely bride and tonight is our honeymoon and I am your lovely new bride which you are going to make love to for the very first time."
As she spoke she was running her soft hands over my body and quite boldly she was playing with my cock. In bed we lay face to face, as she played with my cock while at the same time she was kissing me passionately on the lips. I quite naturally responded by playing with her nipples and I was soon laying in her arms sucking on each nipple in turn, accompanied by her loud moans and groans, which told me that she was enjoying every second of it.
She pulled me away and then so that I was lying on top of her and I found that she had maneuvered her body and my cock was just pressing against her pussy lips. I could feel some moisture running out of her pussy as she slowly opened her legs and using one hand guided my cock inside her. Her hands were clasped tight round my buttocks as my cock slid inside of her waiting pussy. I could feel her cunt muscles clenched hard against my cock and producing a range of sensations that were so totally knew to me...
This was my first fuck with a grown woman and I was in heaven as together Barbara and I got into a rhythm as she pulled me up upwards and hard against her body. The rhythm got faster and faster until I knew that at any minute I was going to shoot my stuff into her. I felt my back arch as suddenly I let go a long spurt of my juices into Barbara. I felt her tighten around me and just as I thought I had finished, her body clenched me tight and she let out a loud noise something between a scream and a groan and I felt her have a massive orgasm as juices washed over my cock as they leaked out on to the bed clothes
Her hands were all over me, and she cried out again as she continued to hold me close. I felt her fingernails scratching my back as she seemed to have a whole series of smaller orgasms. She hugged me close and kept on kissing me. I was soon hard again and time after time we came, until exhaustion set in. That night we slept together naked, our naked bodies intertwined until the early hours when we awoke, as Barbara once again guided my hard cock inside her once again I responded and this time it seemed even better than before until once again as dawn broke we parted totally exhausted.
Then to my surprise Barbara moved her head down my body to take my cock into her mouth. She started sucking and moving on me until once again she brought me to the brink of orgasm And then it happened ... spurt, spurt, as I came in her mouth.
She pulled me away and then she carefully pulled me over on top of her so that I was lying on top of her and I found that she had maneuvered her body and my cock was just ready to enter her pussy. I could feel some moisture running out of her pussy, as she slowly opened her legs and using one hand guided my cock inside her. Her hands were clasped tight round my buttocks as my cock slid inside of her waiting pussy. I could feel her cunt muscles clenched hard against the length of my cock, and producing a range of sensations that were so totally knew to me. Not even young Judy had the expertise of my new lover.
This was my first fuck with Barbara and I was in heaven as together we got into a rhythm as she pulled me up upwards and hard against her body. The rhythm got faster and faster until I knew that at any minute I was going to shoot my stuff into her. I felt my back arch as suddenly I let go a long spurt of my baby seed into Barbara. I felt her tighten around me and just as I thought I had finished, her body clenched me tight and she let out a loud noise something between a scream and a groan and I felt her have a massive orgasm as her juices washed over my cock as they leaked out on to the bed clothes
Her hands were all over me, and she cried out again as she continued to hold me close. My cock was soon hard and as I we came again she seemed to have a whole series of smaller orgasms. She hugged me close and kept on kissing me. We seemed to be going for hours until exhaustion set in, and we slept our naked bodies intertwined until the early hours when we awoke. Night after night after that Barbara insisted that we have sex and this time it lasted a bit longer and it seemed even better than before until once again as dawn broke we parted totally exhausted.
Then to my surprise Barbara moved her head down my body to take my cock into her mouth. She started sucking and moving on me until once again she brought me to the brink of orgasm And then it happened ... spurt, spurt, as I came in her mouth.
Barbara seemed to have a very high sexual appetite and she seemed to be intent on teaching me everything it was possible to learn. Then one night a month or so after I had moved in with her she said.
"Have you ever thought what it would be like to be a girl Tony?
I said "Yes I did often because my mother had sometimes wished that I was a girl."
"Well honey" Barbara said. From now on I am going to teach you how to be a girl. From now on you will only wear girls clothes when you are home with me. And quite soon you will be a lovely girl I am sure. I am not trying to make you into a girl I just want you to be able to pass as a girl when necessary. I always wanted a daughter and in you I have a wonderful lover and now it would make my life complete if you also became the wonderful daughter I never had."
Chapter 2 Next
I Graduate with Honours
By now I was completely in Barbara's power. She looked after me and made me feel so wanted. She was both a mother and a lover." from that day I was gradually introduced to girls clothes. I would go to school wearing girls panties under my clothes except on sports days when I had to change with other boys around, and most evenings I would be trained by Barbara on how to apply make-up, and how to look after my growing female wardrobe. We had to be very careful to ensure that I was not seen by the neighbours, but quite soon I began to feel confident in wearing high heels. I was a bit conscious that I now had partially plucked eyebrows, and I had to be very careful to ensure that I did not carry the smell of perfume with me when I went to school. But Barbara would inspect me very thoroughly before I left the house.
So I was lost and agreed to go along with the change. I must admit that I enjoyed the softness of girls clothes, and I had to admit that I had enjoyed the feelings that it gave me.
About two months after my mother death when all the legal things had been sorted out and my adoption was complete Barbara suddenly announced that we were moving house, and that before we went we would complete my transformation.
We packed the cases and the next day we left early in the morning and we stopped at a very expensive hairdressers A short while later, my head was under the faucet of the sink, as a lady expertly washed my hair with a sweet smelling shampoo. Next she rinsed a conditioner through it ... or so she said. As I was waiting for the conditioner to work, I dozed off and I was awakened by an odd tickling sensation on my feet. I looked down and one of the shop assistants was filing and painting bright red nail polish onto my toenails.
"Well, Toni, I think that you are going to be a real beautiful young lady and I think we shall just have to spell your name Toni from now on darling" Barbara told me.
Have a look at your self in the mirror sweetie!" And she whirled the chair around, so that I could look in the mirror.
There was only one major change so far, My hair had been wrapped tightly in rollers, and shortly the attendant squeezed a foul-smelling liquid onto my rolled-hair. I knew then that I was getting a perm!
"Don't worry Tony it will be absolutely adorable with that natural golden blonde colour that you have."
A short time later, after sitting under a dryer, I was having my fingernails filed and polished the same bright red colour, by the same young lady who had previously done my toe nails, while Barbara had come back to the salon with a whole lot of shopping, just as the assistant started to comb my hair out, producing a flattering golden blonde pageboy style, reaching to just above my shoulders.
As the morning wore on I found that Barbara had spent quite a lot of money on new clothes for me, to save me the embarrassment of shopping as a boy for girls clothes. Next one of the assistants started tweezing my eyebrows into a thin feminine arch, accenting my eyes with blue-green shadow, eyeliner, and mascara. Finishing with a slight blush stroked on my cheeks which gave me a nice glowing look, while a red lipstick, that matched my nails, made my lips look wet, kissable, and desirable. In the end, I was definitely a Toni--and even I had to admit to myself that I looked absolutely stunning.
Barbara took me into a back room where she helped me on with a pink padded bra, padded out with tissue paper, pink garter belt, flesh coloured stockings and a white minislip. Over it all came a red mini dress, the skirt stopping about an inch above my knees. On my feet, Julie had found some red patent leather shoes, with a strap across the instep and about a two inch heel.
A look in the mirror together with Barbara and I must admit I made a very passable girl. Barbara had also bought me a raincoat and an umbrella, together with a red handbag. There were a few other clothes in her bag like a very sexy nightdress and spare panties. Just as we had finished Barbara said "Even I did not think you would be this glamorous. I just love my new daughter..."
Barbara had also bought a few items of jewellery for me, a heavy gold chain like the one she always wore, then she told me Toni dear we will just get your ears pierced, so that you can wear some really nice earrings"
Later over lunch at a local hotel Barbara asked with a big smile "Do you like being a girl Toni? But always be clear honey, I also love the real Tony the one underneath the clothes."
That day was my public debut as Toni, we travelled to a local sea resort and registered as mother and daughter at a very select hotel. Barbara explained that over the next few days I would have to be a girl in public all the time, to get me used to my new role. For the next few days we sunbathed, danced at night and did all the things that mothers and daughters do, including shopping and trying on new clothes.
Then on the last day Barbara sat me down and said. "Tony. Tomorrow we go to our new home, but I am not really supposed to tell you everything now, but I am going to. First of all I have no intention of turning you into a girl permanently, although I must admit that most of the men now seem too want to look at you rather than me. I and two other ladies jointly own a clinic for very wealthy women who have fallen foul of the law, through slight psychiatric problems. In every case it was because they had sex with young boys. But because they are so wealthy and because they have the right contacts in high places, their husbands have put them into a voluntary clinic where they will serve their sentence instead of all the publicity of going to court and prison, but now they are incarcerated in our clinic until the courts judge them fit to go back into society.
We don't see why these poor ladies should be deprived of their fun, especially as they can pay for it, and so you will be their guest, and we just want you to be as nice to those ladies as you have been to me. Our license does not allow us to have any men under fifty years of age working in the clinic, but we are finding that these ladies or girls in most cases need young male company. You are to be that male company, but as far as outside authority is concerned you are just another inmate with problems. We have created a complete set of medical records for you in your female name of Toni Nash, and so you will be treated just like one of the girls. But after lights out, well I am sure that the girls will keep you very busy."
All this happened just before my fifteenth birthday and I said to Barbara "What about school?"
"Well honey I think that your schooling will be in very good hands as you will see when we get there.