This is a story written over a period of time (when I had time that is) consisting of 10 parts. I regard it as highly erotic and covers one persons journey through 5 years of their life. If you are not into transgenderism then I suggest that this story is not for you. It is not all about sex, sex and more sex (granted there is a LOT of sex) but you may need tissues for other reasons too. A large part of this story concerns the feelings, the highs as well as the lows of the subject.
If you are offended by acts of a sexual nature, then you may find you are on the wrong site entirely. If you are too young to be reading this in your country/region, I will tell your mommy.
If you want to comment please feel free to email me at the address listed above, if you want to flame please feel free to drop a very large rock onto your head.
Al persons named and featured in this story are fictional and bear no resemblance to anyone living, dead or not yet born.
Part 4 – The Virginity
Tonight is a Friday night and I know the routine. Marie told me that she was bringing a new man to the flat and something different would happen, I wasn't to be told what but that I was to be totally clean and on my best behaviour.
8 o'clock came and my mistress wafted in through the door with a handsome black man in tow. It never ceases to amaze me how I now look at men in a sexual way, but at the same point I can't ever remember the point in time when they started to look sexually appealing to me. He had a good figure and well tailored clothes that hinted at a muscular frame, chiselled good looks and the deepest brown eyes I had ever seen, I knew I was going to enjoy pleasuring this man. I also knew from the appreciative looks I was getting, he was certainly going to enjoy me.
I was ordered to serve a light supper so off to the kitchen I trotted in my black teddy and matching thong, my hips swinging because of the heels I now habitually wore at home. I kept myself shaved from top to toe so that I would not spoil my hold up stockings and I admit, I did make a pretty picture from the back.
Dinner was served and eaten (I had already eaten previously in order to serve them better) and a bottle of wine was in the process of being demolished by this handsome man and my mistress. "Michael, it is time for the main course, please see to it that our guest is ready for this evening's festivities" I knew what that meant and I was immediately in front of his crotch opening his flies and releasing a nice 9 inch cock. My mouth immediately went into action licking and teasing the glans before plunging my mouth over his exposed manhood. I kept this up for 5 minutes licking and sucking before Marie dragged me away and led us to the bedroom. I was told to undress the man which I did, exposing a masterful hairless chest, dark brown nipples and a very well defined six pack. I took some time lingering with my tongue on his nipples before sliding his trousers and boxer shorts down his legs and giving him another very short mouth action on his raging cock.
I was told to come to the bed as Marie wanted to be prepared but I was unwilling to let go of this wonderful meat from my mouth, not that I needed have worried as it turned out. I was ordered onto my knees in front of Marie's willing snatch and I went to town, licking and slurping her pussy, next thing I knew this beautiful cock was back in my vision and I was alternating between sucking cock and slurping pussy. Marie turned onto all fours to allow this lovely cock access to her waiting and soaking pussy which needed no second bidding. He slammed full force into her and buried his meat into her up to the hilt in 1 hit and then started riding my mistress like a man possessed, all the while she was bucking back at him. After 5 minutes of this furious pace he changed his angle and started fucking her ass, something I knew would have her cumming in a very short time especially with the amount of pussy and clit fingering that was going on.
I could tell from the grunting and moaning that both of them were approaching their climax when he suddenly turned her over onto her back, lifted her legs into the air and started once again on her pussy, hammering into her hard and tweaking and sucking her nipples until she went wild, bucking and thrashing, forcing her pussy up onto this wonderful cock. I could see him cumming into her, his cock pulsing as he deposited his seed deep into her cunt.
They finally managed to come down from whatever cloud they were inhabiting and he rolled off, a veritable torrent of cum poured from her battered hole and down into the crack of her ass as they lay there panting and glistening with sweat. My own panties were damp with my addition to the smells that were abound in the bedroom when a hand gesture from my mistress ordered me to clean up our guest. "make sure he is clean now, I want him ready to go again shortly"
I really needed no other excuse to experience that cock again, soft as it was it was still covered with a mixture of his and her juices, a heady cocktail at the best of time made even better by my attraction to this god of a man. Slowly I started to lick and savour the smells and tastes of this wonderful meat and in short order I was rewarded by the stiffening of his manhood, now my intensity surged and I licked and sucked his man meat like a lollipop, willing it to rise further and return to its former glory.
"you certainly like that cock don't you my little slut?" purred my mistress, I could only grunt an affirmative as his cock was getting just long enough to reach into my throat, my favourite position. "that's good, because that cock shortly is going to take your virginity and you are going to know exactly what it feels like to have a load of cum dumped into your arse". My mind reeled and I paused in my sucking, however the words had another effect on the cock in my mouth which jerked, helped by the hand on the back of my neck pushing my head further onto it.
"come, it is time you took care of me" I moved across the bed, still on all fours and placed my mouth over my mistresses pussy, licking up all the juices my tongue could find, across her perfect and recently fucked ass and then into her pussy to recover what I could. The man had moved behind me and hooked the crotch of my panties to one side, I felt him drip saliva right onto my asshole and work it around with his finger. Now up to this point I had taken 2 of my mistresses fingers in my ass in her training of prostate massage so I was no stranger to having my ass probed, but I knew full well that this cock would be something else entirely. His probing of my ass felt good nonetheless and I soon forgot my trepidations and went back to my job of licking and sucking Marie's pussy and ass, occasionally probing her stretched anus with my tongue for that extra something.
So intent was I on pleasuring my mistress that I was unaware that the fingers had been withdrawn, it was only when I felt something blunt being pressed against my hole did I realise I was about to get fucked for the first time. The pressure ramped up and I felt my asshole begin to stretch wider and wider, he would draw back a fraction of an inch and then resume his inexorable progress inside me. I felt as though I was being stretched to the limit and the pain was almost unendurable and sweet at the same time when all of a sudden pop, my ass closed around his head. A shot of intense searing pain shot through me making my jump but mistress had been waiting for this. Her hands closed around the back of my head and pulled my face harder into her crotch, jamming my extended tongue deep into her waiting cunt.
He held still for a minute and withdrew slowly, I felt my ass closing once again before he pushed a second time and in popped the head again, another shot of pain but less than the first. I felt like begging for him to stop but my love for my mistress and the feelings of wanting to please her overwhelmed me so I gritted my teeth and bore him. His second push managed to work his cock deeper inside me than I thought it was possible, in reality it was only his head and maybe an inch of his thick cock inside when he started to pump, every stroke going deeper and deeper with his strokes getting longer and longer. I was soon amazed to feel his tight ball sack in contact with mine and I realised he was all the way inside me, the pain had long since abated now there was just pure pleasure. I felt his hand reach around to my unbelievably hard straining cock which was leaking fluids at an incredible rate, he scooped up some and on his next trip out of my ass, spread some onto my strained and stretched hole. He was actually using my cum for lubricant.
This soon had me pushing back against him, forcing my ass onto his shaft, willing him to fuck me harder. I realised that this is what all this had been building up to, I was now totally subservient to my mistress and whoever she thought fit to fuck me, to ram their cock down my throat, to force their pussy or tits into my mouth, I was their sex slave and they could do anything they wanted to me.
His rhythm picked up and his cock slammed into my willing arse time after time, occasionally re-lubing my arse with copious amounts of my own cum or his spit to stop my hole from drying out, just when I thought he couldn't fuck me any harder, he did. I was so lost in my own pleasure I totally forgot to lick the pussy that was in front of my eyes, but my mistress sensing that I was somewhat overwhelmed took care of her own pleasure and allowed me to experience my first fuck without let or hindrance. This thought only made me love her all the more, just as I loved this anonymous black cock that was currently ploughing my arse ready for his seed. And when it did come, I knew I had been planted. His thrusting grew frantic, great grunts came from his mouth and I felt his cock swell in my ass, stretching it further as he shot volumes of cum deep into my willing pussy. Feeling his cum splash my insides sent me totally over the edge and I filled my knickers with everything I had left.
His thrusting stopped with only the occasional twitch as he collapsed on top of me, his cock still buried in my pussy and still pulsing the occasional dreg of cum into me. It was a miracle I didn't fall on top of Marie but she had the presence of mind to see what was going to happen and moved out of the way first. After a few minutes he withdrew his member from my hole and I felt my first trail of cum trickle out of my used and abused hole, over my ball sack and mingle with my own juices in my totally ruined knickers.
I had never felt so utterly satisfied in my entire life. I loved the feeling of his sperm in my ass warming me from the inside, my hole slowly closing and stopping the flow of fluid from my insides. This was now my cum, this was now my purpose in life, I was here for this reason, to serve cock, to take cum and to feel like a woman. That realisation shocked me at first, but I knew then that I truly wanted to be a woman. No, I truly WAS a woman but it took an injection of sperm to make me realise that. The memories of first putting on women's clothes and feeling how natural they felt, sensing the wiggle of my hips when I wore heels and the feeling of sexiness when dolled up to the nines all made perfect sense to me now.
The rest of the night was something of a blur, I was fucked again and again in varying positions, my mistress and I would share the cock for the rest of the night until we all collapsed into an untidy heap on the bed. I lost count of how many times the cock exploded inside me, of how many cock full's of thick creamy spunk ended up inside my pussy but I do remember waking in the morning, feeling extremely sore on mistresses's bed and strangely alone. I was revelling in the feeling of an abused but satisfied man pussy when I heard my mistress bidding farewell to our anonymous guest and the door closing behind him.
"So my little cock slut, I see you are awake. How is my little whore this morning?"
I tried to sit up but my sore arse stopped me in my tracks. "Just you wait there for a minute" she said, a look of concern shooting across her face. She went around the bed to her nightstand and brought out a tub of cream, "I hadn't expected you to go at it quite so hard last night, I can only imagine what your poor little pussy must feel like this morning". With that she rolled me partly onto my side and spread my legs so she could gain access to my aching cunt. Dipping her hand into the tub of cream she spread my arse cheeks apart and inspected the damage.
"It's looks very sore, but its closed up again nicely, no tears or bleeding and apart from the redness you would never know you weren't a virgin anymore." she applied the cream to my tender hole which made me jump as it was quite cold but soothing at the same time. She gently inserted a finger into me which made me jump and wince but the pain was only momentary as the cream did its beautiful work. Finishing her first aid she turned me onto her back "So tell me, what did you think of last night's activities?"
I told her how much I enjoyed it, how pleasurable it was to feel the object of so much passion and finally told her of the realisation I had come to after that first fuck. She just looked at me, I could see tears welling up in her eyes and I thought I had upset her or displeased her in some way, then the most beautiful smile broke across her face and I could see they were tears of joy and not sadness.
"I have been hoping you would come to that realisation for about 3 months now, you see unlike Kate who has cross-dressing tendencies, I saw you as a full transgendered person who couldn't see the wood for the trees, there you were going through a succession of female partners never once realising that it was you all the time who wanted to be loved, wanted to be fucked and you who wanted to feel what a woman can only feel which is the pure ecstasy of a man making love to you and planting his precious seed where he wants it most."
With that she hugged me fiercely and we both wept. "OK" she said eventually after we had both wiped our tears "this is going to take some planning but we should also see about getting you a new wardrobe."
After a brief search on the internet we found a TG friendly clothes shop and made our way there. The sun seemed so bright, the day so light and I wondered how much this had to do with my mood. It felt as though a great weight had been lifted from my shoulders as we browsed through the dresses and skirts, blouses and finally into the back of the shop where all the lingerie was. The attendant was a pretty looking thing, darling figure and perfect breasts that stuck out, she introduced herself as Rebecca and was full of hints and tips. I would never have dreamed that she too was a full TS, having been through surgery 3 years before and living with her partner happily for over 2 years.
The pile of clothes mounting on her arm looked far too much and I wondered how I was ever going to pay for all these, I mentioned my fears to Marie who just smiled coyly and told me all would become clear soon. After a bit more browsing, she sent Rebecca off to see about some shoes and then drew me aside. "When I called you my little whore this morning, I wasn't joking. That man who came around last night was no ordinary man, he was what we call a 'punter'. That little episode you gave him last night earned you £2500, it was going to be put aside and I was going to reveal to you that you were essentially being pimped out as a very expensive call sub once we had finally figured out exactly which direction you were going to go on, well now we have."
I was stunned, I was actually a whore, I was someone who sold my body to the highest bidder purely for sex. I was to be used as a fuck hole time and time again and it appalled me, then intrigued me then turned into full blown lust as I realised that not only could I get as much sex as I wanted, as much cock as I wanted but I'd be paid to do it ... I'd have done it for free and £2500 was a hell of a lot of money. "Let's go shopping" said I
Another 18 months has passed ...
Marie was good to her word, she found a private doctor that specialised in transgender treatments, he was ultra professional and referred me to a psychiatrist, private again, who helped me with my case. I was apparently a clear cut case of transgenderism realisation of which has only surfaced recently through developments in my personal life and the meeting of a kind enough spirit that allowed my true feelings to blossom. I decided at this point that I was not going to let him in on the secret of exactly HOW I came about this revelation, the less said the better. All in all, that took about 6 months of repeated psychiatric evaluations and was rubber stamped by a second psychiatrist. Finally my treatment could begin ...
The actual drug therapy was remarkably simple, all this constant sex in a subservient role seemed to have the effect of dampening my ability to produce testosterone and my doses of estrogen had to be dropped twice because of over development. While all this was going smoothly however, work was not.
My budding femininity was starting to show and it was getting increasingly difficult to hide the fact. Being the male dominated society it is, Marie and I decided it would be better if I stopped work until my change was sufficiently advanced for me to pass as female with absolutely no questions asked. I was however tasked with practicing my lifestyle change, makeup techniques, how to walk in 6 inch heels, fashion tips and the like.
And then 3 months later my mother died...
Dont forget to read the next installment: Part 5 - The Family