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This is a true story (I have changed the names for obvious reasons) about how, with the help of Literotica, I finally became a woman. My boyfriend challenged me to write this account and submit it to Literotica and anyone who knows me, knows that I nearly always accept a challenge. I am very grateful to michchick98 who kindly took time out of her busy life to act as my editor and made very useful amendments and suggestions. I am also grateful to FG, without whose encouragement I would probably still be just imagining this event. Enjoy!
I was born in London in 1987. My mother had severe complications during her pregnancy, and as a result, her womb needed complete removal immediately after my birth. From my earliest days I preferred “boy’s toys” like Action Man instead of Barbie Doll and I loved sports; including soccer, cricket, tennis and the martial arts where I became a Black Belt in both Judo and Karate. I have won Cups and competitions in all those fields. I also enjoyed drama, but I was always given the “male” parts if the production was short of men.
My cousin, Charlotte, was like a sister to me (she was a month older), but was totally feminine. When she was thirteen she was raped and stabbed by three men, and despite a massive police search, no one was ever caught. She had to be admitted to a psychiatric hospital where, nine months later, she was raped again, this time by a member of staff who was later convicted and had to serve ten years in prison. Since then she has been in state of “permanent psychiatric shock”, a coma, and although she does not recognise anyone, I still try to visit her as often as I can.
Her mother, my mother’s twin sister, was so traumatised by what happened she had a stroke and died, while her husband took his own life. The shock of all this gave my mother a heart attack (some identical twins have a psychic link) and within three years of Charlotte’s rape she was also dead.
From the day my mother died, my father could not concentrate on anything for long and lost all interest in life. One cold winter night, he lost control of his car, drove into a wall and died instantly. So, by the time I was eighteen I was alone in the world apart from my dog, Prince. By now I had started nursing and the hospital allowed me to keep Prince in the nurse’s quarters. He was so popular and everyone loved him, but sadly, I had to have him “put down” a few months ago.
In all this time I had never had a boyfriend, and what had happened to my cousin left me with a dislike for men. All my friends and colleagues had boyfriends and by April 2008 I was the last virgin on the soccer, cricket and martial art teams as well as in my intake year for nursing. George, the Tom Boy, had never even been kissed.
I can’t remember exactly when I found Literotica. I was just bored one night and fancied reading a sci-fi story on line. Page after page rolled by, but one attracted me (I can’t even remember the title now) and I started reading it. It was not just sci-fi, it was erotic as well. One thing led to another and I discovered this community of people who were not afraid of sex. In December I registered a profile, read the stories, but thought nothing more of it
Then in April, Luke, one of the most attractive, young, athletic doctors in A&E, the place I was working, asked me for a date. I thought he was taking the piss but I went along, straight from tennis in my track suit and met him in the local bar. I was on my guard and therefore nothing happened, not even a kiss. But, Luke was persistent and asked me out again and again. I’d go, but always as Tomboy George, and I never let him get close. One night I got home and found I had received a “personal message” from another Literotica Member, F.G. That contact was to change my life.
On canlı bahis şirketleri 14th May those of us in our intake year took our final nursing exams for this academic year. In the autumn, some will continue at the hospital while a few, like me, will continue our training in the forces, (I’m due to join the British Army in December and am already in the Territorial Army, the Reserve Force).
We all went for a drink and Luke was there. He whispered in my ear telling me how much he fancied me and what he would like to do to me in bed. I was horrified and just laughed at him. But he persisted and challenged me to come to his flat the next day where he would cook me a meal. No strings, I could leave when I wanted and he would do nothing without my agreement, not even try to kiss me.
There was never any question of him forcing me into anything. I’m a martial arts champion and he knew I could snap him in two if he ever tried to do anything I didn’t want him to. I always accept a challenge so I accepted his invitation, knowing I would get a good meal while he would finally give up trying to bed me!
But I had not allowed for F.G. in all this. She also challenged me, dared me to go to this meal with Luke, not as a tomboy, but as a feminine girl. As I’ve said I never accept defeat, and I never dodge a challenge, so I agreed to go as Georgina, not George. Problem was, I only had one dress, one skirt and little feminine deportment. I rarely wear high heels (I’m six foot one) and I walk like a man!
F.G. told me I had to come to terms with myself and stop blaming all men for what happened to Charlotte. She challenged me to sleep with Luke if I felt attracted to him. My head was spinning! I had lived such a sheltered life as far as men were concerned. All I could remember was my Irish Catholic mother telling me that “good girls don’t touch themselves”. That “good girls wait until they are married before allowing their husbands to touch them”. That “good girls realise their husbands have needs that women would never understand”. I wonder what she would have thought if she knew I was reading erotic literature?
F.G. advised me to get my legs waxed, shave my pussy and arm pits and take a close friend with me to pick an outfit for the night and take a bottle of my favourite wine. Then while we were online together, Luke telephoned to tell me he had booked a taxi to collect me and had arranged for another to take me home after our meal. F.G. challenged me to call him back and tell him to cancel the taxi booked to take me home. I was caught! If I did call Luke I would appear what my mother would call “loose”. If I didn’t I would have dodged a challenge.
Nervously, I called Luke back and told him to cancel the return taxi. He was shocked when I told him but he said he would tell the cab company to keep it on standby.
I went with my close friend Sue to the shops and bought an outfit; a black top and short skirt, red self hold stockings along with a red lacy bra and matching panties, a red slip, red lacy panties, red scarf and black high heel shoes. I had my hair “done”, nails manicured, legs waxed, had a tanning session and I shaved those important parts. I got back to the nurse’s quarters feeling sick.
My heart was pounding, as it does when I’m serving at tennis at match point, or taking a vital penalty in a shootout! I could feel my pulse in my head, chest, throat and stomach. I had one more exchange with F.G. and told her I was terrified. Medically I knew I was safe because Luke and I work in Accident and Emergency and are regularly checked for HIV and other sexually transmitted diseases. I’m also on the pill to help regulate my periods.
My last message to F.G. read, “Oh God, I feel sick, I’m going to die. I’m really going to do it! Oh canlı kaçak iddaa God. Taxi’s here. Think of me.”
My stomach was in knots when my taxi arrived to take me to the doctor’s quarters where Luke lives. For the first time in my life I was dressed as a sexy woman, but struggling with my high heels as I don’t wear them often. When I arrived, I nervously rang the bell to Luke’s flat. As he opened the door his eyes went straight to my cleavage. There was a dark lust in his eyes and I felt my nipples harden. He kissed me on the cheek and invited me in. Took my coat, hung it up then took my bottle of wine and opened it.
“George? I don’t know you,” he said.
“I’m Georgina today,” I replied. Then I heard myself saying, “A girl who wants you to make her a woman.” My heart was pounding.
He sat me down, poured me some wine and we sat next to each other on his settee. The bulge I could already see in his pants was evidence of what was to come. I could not believe that a rugged handsome Aussie man like Luke would get that excited over me! He could see my consternation and led me to the dining table. We sat and enjoyed the dinner. He really is a good cook (I’m not, I go for ready meals and tinned food) and after we finished eating he led me back to the settee where we started kissing. That was the first time I had ever had someone else’s tongue in my mouth.
“Do you really want to do this?” he whispered. I could feel my pulse racing and I know I blushed. I just got up and asked him to take me with him into the bedroom. “Why the change?” he asked as we went through the bedroom door.
I just smiled. “I’ve been taking lessons on my own sexuality,” I replied and flung my arms round him.
He began unzipping my top. Next my bra was off. His eyes narrowed. “My God, underneath that tomboy is a beauty I’ve always believed was there,” he said.
“The tomboy isn’t here today – she’s on sabbatical. I’m here in her place,” I replied and began to unbutton his shirt.
He started holding and twisting my nipples. No one had ever touched me there before and pleasure explosions rocked my whole body as my nipples became hard like small chunks of diamond. When he started licking and biting them my pussy started throbbing and I could feel my arousal heighten, evident by the wetness I felt between my thighs.
He quickly removed his trousers and under pants and for the first time I saw his magnificent cock. I had seen naked men before, but I had never seen an erect penis in my life, apart from in diagrams as part of my studies. This man was losing control because of me! And what I now know was pre – cum was oozing from the tip of his cock. I gasped.
He pulled me to him and I can remember being worried that his pre – cum would stain my new black skirt. “Don’t worry about that,” he said as he unzipped my skirt which was soon joined by my slip on the floor.
All I had on now were my stockings and panties and our eyes met as he lowered me down onto the bed. I was already wet and he could see I was.
“Last chance to change your mind,” he said. “After this …”
I didn’t give him time to finish that sentence, instead I just grabbed him and kissed him. I took hold of his cock, not able to believe that I, George the tomboy, had made this wonderful specimen of a man so horny. I had “pushed the right buttons” and turned this handsome, fit, athletic doctor on!
Suddenly, he groaned and shouted, “NO!” as he shot his load onto my stomach, my breasts, my legs and my hand.
I was saturated in his warm, sticky cum. I can’t believe how innocent I was, but I’d never seen cum before and I had to check with him. “Is that when the sperm is released?” I asked.
He nodded and was full of apology, but I was flattered. I never thought canlı kaçak bahis any man, never mind this man, would ever do that because of me. I kissed him and reassured him as I let him rub his seed into my nipples. I thought back to some of the Literotica stories I had read and leaned in to lick his cock. That was a taste I have never had before, “creamy and musky” is the best way I can describe it.
Gradually he hardened again. “You have been given a reprieve,” he said. “Last chance – do you want to keep your virginity or not?” I didn’t answer, I just kissed his cock; the cock that was soon to become my conqueror.
He pushed me down again onto the bed and removed my saucy red knickers. “They’re wet,” he said. “Naughty girl.”
I blushed and kissed him hard. As my tongue invaded his mouth I felt his fingers on my pussy, another first, as never before had anyone ever touched me there; pushing, rubbing, testing the lips. Next his cock was at the entrance. He was so big. I was so small. How would he get that into me?
He sensed my panic. “Last chance. Yes or no?”
I cried out, “Fuck me now Luke, before I change my mind!”
He pushed forward gently. I’ve been through the pain barriers at soccer and tennis but this was different. He pushed again and I yelled in agony, as panic set in. I wanted to stop, I couldn’t go through with it, but it was already too late. He was different now, and kind, considerate, gentle Luke had gone. In his place was this sex hungry beast who was going to “have me”.
He had given me my last chance to save my virginity and I had refused it. I realised then that I was living through my final seconds as a virgin, and for the first time in my life, I surrendered. My heart was racing but time seemed to stand still. We made eye contact and then I screamed as he launched forward and I felt something give deep within me. It felt rather like an old, thick skewer being driven through a piece of meat. Then there was a ripping sound as my hymen split in two and I finally lost my virginity. I yelled again as blood started flowing from my pussy down my thighs and on to the bed.
He lay there for a few seconds, almost apologetic as my eyes filled with tears. I was in agony, and he knew it. Nothing had ever been in my pussy before, I did not even use tampons, and now this monster cock, full of seed had invaded my most private space. As we lay there, him on top of me he started rocking back and forth, gathering speed. Each movement brought more and more pain as he pounded into me.
Then, gradually the pain began to ease and another sensation took over. The pain was still there but this other sensation gained momentum. Pleasure was starting to break out in my womb, my pussy, my breasts, and my nipples which felt as though they were about to burst. Then, just as I thought the pleasure could never be more intense, nature took over and I felt the muscles in my channel grip his cock as a tidal wave of pleasure lifted me up, almost out of my body.
For the first time in my life I was experiencing, through the pain, total orgasm. I was cumming, gushing on his cock with such pleasure I thought I would pass out. I dug my nails into his back while his name roared from my lips. Then my eyes met his and he groaned with me. Now it was his turn to shout, releasing wave after wave after wave of seed down my channel, giving me another, even more intense orgasm as I felt it splash into my virgin womb.
I held him. He held me, his hands grabbing my breasts as we kissed. He eased himself out slowly, apologizing that he had hurt me. He told me not to worry about the blood on the sheet and we just looked at each other as tears continued streaming down my face. Then there was a silken peace as we fell asleep in each other’s arms.
Years ago, long before there was a TV series of the same name, and because of my love of military things and my martial arts, my father gave me the nickname, “The UK’s Warrior Princess”. Well, the “Warrior Princess” is a woman now, learning fast. Watch out world!
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