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 6 – The Clients
The thought of stopping my part time profession did cross my mind, but was quickly dismissed as I was enjoying myself too much, the money was too good and the clientele was certainly worth it.
I don't know where Marie got these people from but they were all handsome, mostly well hung and certainly got a kick out of fucking both of us.
She came to me one day saying she had a rather strange contact from a prospective client, although this time it was not a man, it was a woman. The story went that this lady was married and had caught her husband one day dressed in her clothes, after the initial shock had died they began to talk and he confessed that he always wanted to have sex with a TGirl, so she thought about it and decided that if he was going to, he would do it under her supervision. I said that I had no objections and that even though Marie was not to be directly involved in this fantasy of his, I would still insist that she remained with us the entire time to make sure things did not get out of hand.
The appointment was duly made and the day came ...
Marie opened the door to a couple, both in their late 30's, smartly dressed in expensive tailored clothing and looking like they just stepped off the cat walk. She entered first and introduced herself as Isobel and her partner as Dan. From the moment Dan saw me I could sense his urgency and lust but Marie and I both agreed that we would not jump straight into the bedroom and start fucking, this had to be nurtured to ensure the wife really was ok with it.
As it turned out, we needn't have worried. She was definitely the dominant partner out of the 2, not in the same way Marie and I used to be, but definitely stronger than he was. We chatted over a couple of glasses of wine, she asked most of the questions and he chipped in with some but his main sport was ogling me. My chest had developed so that I no longer needed the bra fillers, I was a comfortable 34B and in the tight top I was wearing, it looked like they were trying to burst their way out. I was consciously crossing and uncrossing my legs, allowing him a good chance to view the tops of my legs above the line of my stockings. I have found that the flash of leg tends to spark more imagination than standing in front of someone stark naked, it allows the imagination to make up what cant been seen for a start.
The questions finally waned and we were just chatting about how this was going to go, Marie and the wife were getting on like long lost sisters and soon were settled on the sofa giggling like teenagers. I took this as my cue to get the ball rolling and I moved across to sit next Dan and snuggled up close. I could smell his musk and the tent in his trousers was unmistakeable and unavoidable. "So sweetie" said I "are we going to get along as well as those 2 there?"
"That's the plan" he said in a strained voice. His eyes were concentrating on my breasts and I was getting incredibly turned on by his gaze and also the looks I was getting from Isobel. There certainly was no jealousy and her and Marie's conversation, even though they were sitting only 8 feet away, was getting harder to listen to as both their voices had dropped. We were obviously the topic of their discussion. At one point I saw Marie's eyes open appreciatively as she sucked in through pursed lips, it was obvious that she was impressed by something and with my hand on a large bulge in Dan's trousers, I could guess at what it was.
It was while he was planting kisses on my neck that I whispered if we should move this to the bedroom and when he glanced over to his wife for confirmation, I turned his head back and whispered "That was not a request or a suggestion, it was an order!" and I bit the lobe of his ear ever so slightly. I immediately felt his cock jump and knew I had hit the jackpot. Not only was he interested in fucking a TG like me, he was also submissive; in the bedroom at least.
Standing up, I glanced over to Isobel who was watching this play intently, a half smile on her lips and a distinct redness about her face and neck, I hooked my fingers through the waistband of Dan's trousers and hauled him upright, "Now ladies, we are just off to the bedroom and don't worry honey, I'll take good care of him" as I winked at Isobel. I think she knew what I meant and the dominance I was showing brought a twinkle to her eye.
As we entered I heard Isobel ask Marie if we were allowed to watch, "Hell yes honey, I plan on doing exactly that, let's just let them get started first." I deliberately left the door wide open I and pushed Dan until he was backing up to the bed, it took only a little shove for him to fall onto it where he scooted himself up to the pillows. Like a cat I crawled onto the bed, straddled him and moved so close that my breasts were almost in his face. I felt his arms reach around me as he unzipped my dress and I pulled it over my head exposing my bubblegum pink matching bra and knicker set. Because of the hormones, my cock had shrunk from its handy 7 inches to almost 2.5 and was now totally useless to fuck with. I found that it was a perfect size however for beginners in sucking cock. I allowed him to kiss my neck and the parts of my breasts he could get to before I moved up the bed at the same time as pushing him down it until my crotch was positioned within inches of his face.
"This is all part of fucking a TGirl, you must suck me off and if you are good enough, I might return the favour." What he didn't know was that there was no way I was going to miss the opportunity of sucking that monster before he fucked me. Hesitantly he reached up to the small bulge in my knickers and traced the outline of my penis through the material. Whilst it might have been small, it was even more sensitive than when it was full sized. I gasped at his touch and started to rock back and forth. I could see in the mirror above the bed that Isobel and Marie had joined us and were sitting at the bottom of the bed on the sofa watching intently. I even managed to notice that Isobel's nipples were extremely hard and poking the thin material of her blouse even through her bra. I winked at her again, she smiled lustfully.
I felt a finger hook into the waistband of my knickers and drag it down to expose my completely hard cock. His tongue reached out and flicked over the exposed head tasting my pre cum, causing me to gasp and jump at this lightest of touches, again a lick and then I felt his mouth close over my cock. Slowly but surely his lips travelled the length of my cock until his nose was pressed hard against me, his tongue tracing circles over the head and back down again. I held onto the back of his head and started to ease my cock in and out of his mouth, doing exactly what other people had done to me in the past. I'd had blowjobs from men before and women in my former life but this was the first time I had actually face fucked a guy, normally I was on the bottom.
I will admit that for a beginner he was quite good at it and I could feel myself getting a little carried away so I pulled out of his mouth. "Not bad for a newbie, but let me show you how it's really done." I span around so that my crotch was still near his face but I was now facing his wife and his cock. I unfastened his trousers and reached in to his straining hard on. I was something of a connoisseur of cocks now and after wrapping my hand around it could tell this was certainly a fine specimen. A good 9.5 inches with a bulbous head, slight curve to the right and tremendously thick. The veins on his cock stood out proudly as I released it from his boxer short prison. I flicked the head of his cock quickly causing him to jump in surprise before pulling down his foreskin and dragging my entire tongue over his cock head slowly. I traced the line from the underside of his head all the way to the base and back up again before spreading my lips and lowering my mouth onto his head and taking the first 3 inches effortlessly, up again and then down to 6 where he started to hit the back of my throat. The appreciative moans coming from the headboard told me I was doing a good job, not that I needed confirmation.
I adjusted my angle slightly and pushed my head downwards onto his cock and the head slid straight down my throat. I was used to having my throat stretched a little but the thickness of this dick took some getting used to, but I still sucked him like the seasoned pro I was. I withdrew my mouth and looked round, "Aren't you forgetting something?" I asked imperiously. I waggled my hips causing my tiny cock to swing before his eyes. He got the hint eventually and returned his mouth to my penis and started gently sucking, except that I didn't want gentle, at least not from him.
I raised my hips slightly, waiting for him to follow and bless him, he did just that and then pushed my crotch hard into his face, the back of his head being forced into the mattress. From this position I restarted face fucking him, all he had to do was keep his lips around my cock as I pulled out and then re-entered his willing mouth. Once he had got the hang of that I returned to his pole, licking and sucking the head of his cock occasionally taking it deep into my throat and holding it there just making swallowing motions to titillate his engorged glans. Meanwhile at the other end of the bed, Dan was getting quite good at sucking my toy cock and I could feel precum leaking out of me, as it often does.
I glanced at Isobel momentarily and got something of a shock, she was sitting on the small sofa with her legs spread fingering herself through the material of her g-string as she watched me suck on her husband's cock, Marie too had divested herself of her thong and was busy pushing 2 fingers in and out of her wet pussy. As I watched Marie leaned forward and kissed Isobel's neck which made her jump in surprise. She turned to look Marie in the eyes when Marie went to kiss her again, so softly, on the lips. Isobel moaned in pleasure and soon their little kiss had turned into some serious tongue wrestling. Marie slid her hand over Isobel's exposed inner thigh and, brushing the other woman's fingers out of the way, slipped 2 fingers under the thin cloth and straight into Isobel's soaking wet hole. This was incredible, I had never seen Marie so into lesbianism in the years I had known her, all I could think was that either I was a lot better than I thought or the whole charged atmosphere just made her take a leap of faith.
Isobel was certainly enjoying it and decided to reciprocate on Marie's smooth wet snatch, soon the noises coming from the end of the bed were louder than those coming from the bed itself.
I had to concentrate hard on what I was doing, I was getting paid to fulfil this man's fantasy and all I could do was watch 2 hot women fingering each other's pussies. On a change of tack, I decided to see if Dan was still a virgin, it was his turn to feel a finger in his ass. I stopped my cock sucking and jerked my own dick out of his mouth. Now that his focus was lost, he caught sight of the other antics in the bedroom and I felt sorry for him, he had no idea which way to look. Not giving him the opportunity to get too lost in lust I leapt off him so that I could undress at least his bottom half. Leaning over the end of the bed I removed first his shoes and socks then his trousers and shorts and threw them into a heap on the floor. Kneeling on all fours on the bed I lifted his legs up over my shoulders and went to work on his cock again. This time he had nothing else to concentrate on except my mouth and the fingering going on behind me.
I dribbled copious amounts of spit down the crack of his ass and pressed my finger to his waiting hole. I could feel him tense a little but as I started to work my finger inside him he slowly relaxed, enjoying the sensations of his first finger fuck. I kept up the sucking on his cock and I could feel his orgasm approaching. Not wanting this to be over too soon, I removed my mouth from his weapon but kept up my finger work. Soon he was loose enough to allow a second all important finger to be inserted and his fucking became more insistent. Before I knew it I was pumping his ass with a regular fucking motion, his eyes were closed as he enjoyed these new sensations. Now was the time to go for the kill. I pushed my fingers in as far as they would go and pulled them up towards his ball sack. I could feel the round smoothness of his engorged prostate as I began massaging it. His cried out loud as this new pleasure hit him hard, his jumping around only served to make my motions more exaggerated than before and he started thrashing about wildly, pushing his ass harder onto my hand with every movement as his precious fluids began to stream from his cock head.
I returned back to my sucking, but this time it was with much greater urgency, shoving his cock as deep into my mouth and throat, licking, swallowing and still fingering his ass. He started face fucking me, every upward stroke of his dick went into my throat and every downward stroke caused my fingers to push harder onto his prostate until he could contain himself no longer. I felt shot after shot of his warm cum splash over my face, down my throat and into my mouth, depending on where his cock was at the time. He seemed to cum forever, another violent torrent was released when my fingers were forced out of his hole through his sphincter contracting on them.
I was going to swallow his cum but when I saw the faces behind me gaping in awe, I thought of a much better use for it. I leaned over to Marie, who still had her fingers in Isobel's cunny, and kissed her full force on the lips, transferring much of it into her mouth. As we broke our passionate kiss, Isobel looked to us with pure lust in her eyes and licked her lips, which met mine with the same kind of urgency. She proceeded to French kiss me fiercely stripping me of all her husband's cum and then went on to lick my face clean of all his still warm gism. Her hands went to my cock and stroked it gently so I put my hand over her pussy and started playing with her clit. This was definitely not in the script but then again, neither was Marie's hand supposed to be tweaking her nipples whilst her other hand furiously frigged her own sopping sex. I lifted Isobel onto her feet and our lips met once again, we crushed our bodies together and I could feel her pulse race against me. Marie stood behind her and stripped her of her clothes as I guided Isobel to the bed, leading her by hooking 2 fingers into her pussy and guided her onto her back beside her husband.
Dan in the meantime was loving this, and while he was not sporting a hard on, he was certainly trying. I lay between them, my face pointing towards Isobel's pussy as I pulled her over in order to taste her sweet juices which were pouring out of her. At the same time I pushed my cock towards her face and she wasted no time in sucking my 2 inch clitty into her mouth. I lifted my leg high so she could gain better access whilst I pulled Dan's head towards my waiting asshole. Hesitantly he licked my rosebud and then I saw Isobel's hand reach round behind his head and pull. His nose was buried in my ass crack as he struggled to breathe but he found tilting his head slightly allowed him air whilst at the same time jamming his tongue straight into my fuck hole. Caution apparently went to the winds as he probed my pink hairless ass with his tongue slowly at first and then pushing as far in as he could get.
At some point in time, Marie had joined us on the bed, also undressed and started giving Dan another blowjob. In no time at all he was rock hard again and I decided that it was time I felt this monster cock inside me. My ass ached for it and his tongue was no substitute. Turning my head from Isobel's pussy I said "if you don't fuck me with that cock of yours now, I'm going to strap a dildo on your wife and get her to do it."
I span Isobel round so we were crosswise on the bed, her mouth still on my cock and mine in the folds of her pussy as Dan took up position behind me. I felt his engorged cock head fumbling around my wet hole so I reached around to grab hold of it and pushed my ass back.
I felt him slide into my eager hole until it bottomed out and then the fucking began. It might not have been the longest I had taken in me but it certainly was the thickest and I felt my ass stretching and loosening further than it had before. I could only imagine the view Isobel was getting from underneath but she certainly worked my cock harder than before and I was soon bucking hard and I was leaking cum at a constant rate, all nicely taken and swallowed by this man's wife. The thought of that alone would have brought me to orgasm, even without the almost constant pounding of my arse and the sucking sensations that were sending electric shivers through my entire body. I was crying out for him to fuck me ... Fuck me harder and as I felt the final peak of my ecstasy his cock exploded flooding my insides with shot after shot of his wonderful sperm. My own cock was pouring spunk down Isobel's throat, and it was only then that I realised it was no longer my mouth on her pussy, Marie had come round to take up where my pleasure had left off and was enthusiastically fisting this beautiful woman's pussy and I saw my first female ejaculation as she squirted all over Marie's arm.
The three of us could barely move other than collapse on the bed in a tangle of writhing and sweat soaked bodies. The cock in my ass was still there, occasionally twitching but gradually softening and I could feel the trickle of cum leak out from around his member. It seemed as though it would never stop but when he pulled out of me the floodgates really opened and my arse was literally soaked in sticky cum, running down my legs, over my ball sack and onto my very limp dick. Isobel finally opened her eyes and turned around so we were head to head again, I felt her come closer and her lips met mine. This time the kiss was full of tenderness and was little more like an elongated peck but it caused me to respond in a way I had not in over a year. I wrapped my arms around her and pressed my body into her, our tits touching, my ultra sensitive nipples pressed into her warm forgiving flesh and our mouths opened, our legs entwined and our crotches pushing against each other. Even if I had been fully hard I could never have satisfied this woman in the way she wanted, especially not after the fisting she had just received and I felt so terribly sorry for her at that moment because even in the height of passion I could not give her what her body so desperately craved.
We broke our kiss and she looked me straight in the eye "Will you teach me something please?" she pleaded "I'll pay you whatever you want"
"Honey, you weren't supposed to join in, nothing we did was requested by you so you won't be paying a single penny extra and at the moment, I would do anything for you; just name it and it's yours."
"I want you to teach me how to do what you do, I have never been able to take anything in my arse and I want you to be my first." I was in shock, of all the things that had been going through my mind, this didn't even show up on any scale I was looking at but with her looking at me with her deep blue eyes, part scared, part tearful with a whole heap of brave thrown in. I couldn't say no. It had been a long time since I had actually used my cock to fuck anyone, on a couple of occasions I had used a strap on on a guy as part of his fantasy but that was as far as it went. I wasn't even sure if it was possible anymore, but on cue I felt a stirring in my loins as if something knew it was the topic of conversation.
I kissed her again, deeply and lifted her uppermost leg high up onto my hip. With my free hand I started to tickle her pussy again, just to get her relaxed and my fingers as lubricated as possible. With 3 fingers in her soaking wet snatch I started to probe her virgin ass. Strangely I thought that this was the second virgin ass I was going to break in tonight, I wonder who's is going to be tighter.
My question was answered almost immediately as I couldn't even penetrate her most private hole with the tip of my finger. Every time I tried her sphincter would instinctively shut tight allowing nothing in. Worse was Isobel who was getting frustrated which only exacerbated matters. With my partially trapped right hand I soothed her, stroked her hair and whispered gently to her in order to calm her down. It's not unusual for this to happen as that reaction is perfectly normal and natural and getting frustrated about it is not going to help the problem go away.
"Isobel, I know how to make this work, but you have to help me. I want you to push with your ass as if you are going to the toilet, not too hard and I can promise you, this will work." I saw her indecision but she closed her eyes and nodded. I felt her sphincter relax and start to open as I kept up the pressure on my index finger. Sure enough only after a couple of seconds my finger slid into her up to the first knuckle. Immediately it clamped shut and forced my finger out but quickly relaxed, Isobel again pushed and again my finger slid in. The reaction this time was mild in comparison, only a slight pressure on my finger as I pushed yet more inside her. Soon I had run out of finger and I was glad to note that she was as clean inside as she was outside. I started a rhythmic fucking movement, nothing too fast and soon she was moaning and pushing back against me. I suddenly felt a flash of jealousy, this woman could take a cock in both holes if she tried, 2 cocks fucking her, depositing 2 loads of cum at a time. She could get through twice as many cocks as I could in the same period of time and I hated her for it although I did love fingering her asshole.
I manoeuvred myself between her legs and lifted them both high up my body, spreading her ass cheeks wide apart and I prepared to insert my cock into the last virginity she would ever have. I guided my almost useless cock to her puckered hole and began to press forward and up, almost immediately her ass clamped shut but this time I didn't need to say anything. She mashed her lips against mine and pushed herself onto my cock which was straining to be inside her and then she pushed out with her ass. Her hole relaxed and I felt my cock slipping inside her a fraction of an inch at a time. I might not have much down there but she enjoyed every single part of it slipping into her willing tight hole.
By this time Dan had managed to get up from the bed and was currently only inches away from the cock that was fucking his wife's arse while he wanked himself off. No matter how much he stroked his meat however he couldn't maintain a hard on but that didn't mean his mouth should go to waste. I lifted my leg high and ordered him to clean me off, I was covered with his cream and it's only fair that he should be the one to remove it. His tongue leapt to my sore ass and soon he was licking and slurping my hole like a pro which only turned me on all the more. Now the sensations were building up rapidly and not just for me. My position between Isobel's legs meant that I was rubbing her pussy all over and the new sensation of being fucked up the ass were winding her up to a wonderful orgasm. I tried to time my movements between Dan and Isobel, torn between my own pleasure and the pleasure of the beauty in my arms as she bucked against me. Every time I heard her moan it turned me on that bit more, the moaning turned into panting, the panting into swearing and grunting and finally screaming as her movements pushed herself harder onto my cock, harder onto her own crotch and shuddering from another orgasm timed perfectly with mine. I felt her juices gush onto my crotch as my cock dry pumped her ass as I had no cum left to give, but I pumped all the same.
I don't know how long we lay there in each other's arms panting, trying to recover our senses, all I do know is that when I came back to my senses my cock was touching Isobel exactly where she asked me to.
Isobel and Dan slept with us that night, she had a nearly insatiable appetite for sex and even Dan managed to recover after an hour or so, long enough to fuck all 3 of us again. Once we even managed a threesome with Isobel in the middle, Dan fucking her pussy and my cock in her arse. I dare say it wouldn't made it into the final cut of a porno film, but it was enjoyable nonetheless.
I was awoken in the morning by a semi hard cock nestling between my ass cheeks, its owner just stirring. Isobel and Marie were spooned together, the strap on probably still inside Isobel's newly discovered fuckhole sleeping peacefully, they looked so beautiful and at peace, it would be a shame to wake them so early but the cock between my cheeks was waking up too. So was my lust.
Moving as little as possible I pushed my ass backwards and up so that I could feel the head resting against my hole and all I did was move backwards until it once again filled me. I could feel it growing inside me as it reached full hardness and as Dan started to pump backwards and forwards. I stopped him with my hand, half turned and put a finger to my lips telling him to be quiet. I pushed back once more so that all of his available penis was buried in me and then used all the muscles I could think of to milk the last remaining drops of cum from his balls. I had finally learnt the trick Marie had used on me what felt like a millennia ago, it's all down to using your internal muscles to create a sucking and rubbing sensation on the head of a man's penis. I soon heard his breath ragged but muffled by the pillow as his hands mashed my breasts getting more urgent by the second. Sure enough I was rewarded with the familiar feeling of cum being pumped deep into my belly followed by his rapidly softening dick.
I awoke later, all alone, very sore but with a wonderful feeling of a job well done and an arse full of yet another man's cum. I made it out of the bedroom to a totally empty flat, had a look in the mirror (I looked like I had been hit by a bus), checked the time, it was a quarter past 2 in the afternoon and noticed the hand written envelope on the counter, there was no stamp
"My dearest Michaela
I cannot truthfully put into words the gratitude we feel towards you, you have opened our eyes and our hearts to each other and for that I cannot thank you enough. Your wonderful personality, your love and your amazing skills are a tribute to all that is good in this world and I pray that you are able to find your true place in life as you deserve to be loved unreservedly for the kind hearted warm and gentle person you are.
I do not know your past but I can see your future, at some point you will come to our house where I hope we can show you as much love and tenderness as you have shown since we met.
My mother recently passed away and this time has been very difficult for both of us but you have shown me that there is life after death, there is a man who loves me very much and there are people in this world who will cherish you. I hope I deserve the honour of being called a friend.
Yours lovingly
Isobel"
I sat in tears reading and re-reading this note, that sweet girl who has so much to offer thinks she would be lucky to have me as a friend - what could I do.
I tore the cheque into little pieces and dropped it into the bin, went back to bed and cried myself to sleep.
We met many times after that, sometimes at our place, sometimes at their house in Buckinghamshire, we even stayed the weekend and went horse riding. Isobel had truly blossomed into a raving sex addict, she could now take Dan's cock in her arse, although not as easily as I could but she was getting there all the same. I managed to fuck her again in the ass and even went on to fist her whilst Dan pummelled her tightest hole. Marie and Isobel always ended up sleeping together whilst Dan and I always ended up draining each other of each other's bodily fluids. And thus the relationship continued.
Dont forget to read the next installment: Part 7 - The Treatment