Living The Life

After packing his bags and saying his goodbyes in "Thank You", what ever became of our intrepid tranny girl with his new breasts, new figure, and new life? Well, it turns out that becoming a tranny girl has allowed our hero to not only find a new side to himself, not only have more great sex than he thought possible, but it's also allowed our hero to starting living the life!


God damn, this is a rush! This stuff turns me on something fierce! It makes my nipples hard, puts a flush on my cheeks, and even under my corset and panties it also makes my dick hard too. No, not hard enough to tent those panties out but you can definitely tell that I’m turned on. Of course, the man kneeling in front of me can tell that as well and that turns him on even more and that, of course, turns me on even more and… well, you get the picture.

I never would’ve guessed that I’d have found so many men out here who wanted to be topped by a tranny girl like me. Yet, the mere mention that I’ve got “something special” between my legs in addition to having a good set of tits on my chest and I had guys lining up for the privilege. That took some getting used to.

Oh, I knew there were guys who had a “thing” for girly boys like me. My lover, correction, my ex lover, had found enough of those. But the ones she found were crude and insulting fools who I wanted no part of otherwise. She’d found them in a desire to break me. She’d brought them home to “do” me and “do” me they did. She figured that enough of this and I’d be convinced I was a worthless “thing.” Yeah, she misread me alright. Misread me completely.

During that time I also knew that there were at least some guys out there who were both interested in trannys and could respect them too. Steve was one such man. Sweet, sexy Steve. Turned out that once my mistress had forced a set of titties on me (yeah, forced – she didn’t ask me if I wanted such a thing. She just drugged me and found a surgeon to do the job) good ol’ Stevie boy couldn’t keep his hands off my tits and couldn’t keep his hands off of me, period. So I knew there were some men out there who I’d enjoy being with.

But I thought they’d want me to stay in the submissive femme role. Silly me. Almost as soon as I got out here to the Bay Area and began checking out the scene I found that I was wrong. So very wrong! Almost all the guys who started cozying up to me wanted me to be the aggressor. They wanted me to roll them over on their bellies and start plowing. I never expected this. But I learned. Quickly, did I learn. I also learned to separate the guys who had an interest in tranny girls from the tranny chasers.

Personally, I don’t have much use for the tranny chasers. They’re too damn closeted for my tastes. They don’t have the balls to admit they’re gay – or even bi. Instead, they want to pretend they’re with a woman – who just happens to have a dick. Too many issues there, thank you very much. Oh, they’ll do – as clients – but not for social needs. And not for personal needs. I want a man who’s comfortable with himself and isn’t afraid to say he likes cock. Those type of men work best for me. But the tranny chasers work too – if properly generous.

That was something else I quickly discovered once I’d moved here. It only took a couple of nights up in San Francisco at the Tranny Shack before I found that some men had a grip on their wallets for me as they were trying to get a grip on my titties. That, and they’d pay good money for even a brief few minutes of my attentions. Initially I was very much put off by this. I wasn’t a prostitute and nor was I a whore. A slut? Yes! You betcha! But nothing more than that. Well, over time, I began to reconsider all that.

First off, the bottom dropped out of the IT sector here in the Bay Area. As the new girl at the company which had hired me, sight unseen, from Back East, I was soon let go from their shop. I also realized that I didn’t have to do anything sexual with these men. By that I mean I didn’t have to have sex with them. Oh, I could bring them to the edge of things, play around with their cock and balls, wag my cock in front of their open mouths and even shake my bared titties at them – but I didn’t have to do more than that and yet they’d still pay for it. I learned this from some of the other T-girl friends I came to know who had already discovered this fact for themselves. Some of them had gotten themselves set up in the various “houses” in the Bay Area and began running a really brisk business from men who’d pay their money to kneel before a shemale.

One of them, Suzy Tease is her out ‘n about name and Goddess Sabrina is her pro name, invited me along to sit in on one of her sessions. That turned out hotter than I ever imagined. I knew she’d set it that way but even so, I was still really turned on by it and didn’t much care if this particular client was a ringer.

She’d chosen well as the client was absolutely gorgeous. Six foot something, 260lbs of pure muscle, hung like horse, submissive as all get out, a deep fetish for T-girls and also utterly, utterly closeted. He was pretty typical of a lot of tranny chasers in this. He’d realized he was bi and had a thing for “chicks with dicks” only after he’d already gotten married, bought the house, and popped out a couple of kids as well. He had a nice, high paying job with a law firm in San Jose and both his wife and his family were too uptight to cotton to the idea that their darling, perfect, straight laced, macho man, liked to be dressed up as a cheerleader and then bent over a shemale’s lap with his skirt hiked up so she could spank him and he could start squirming around until he felt her cock harden beneath him. Yet, that was exactly what he liked and, if done right, he would even manage to “wet his panties” as a result.

I couldn’t believe it when I first saw this man submit to Goddess Sabrina this way. Something bit me watching it. I felt a real strong burning inside me as I watched her put this man through his paces. For one thing, it was all I could do not to fall on that boy’s dick once Sabrina had “accidentally” worked it loose from his panties as she’d bent him over. She’d been doing the whole tease routine (and you wondered how she got her regular name?) with this guy for about half an hour before she decided to “punish” him for being “bad” by putting him over her knees. Damn, he had a cute ass. What sent him over was her caressing that cute ass after she’d spanked it nice and cherry red and then began talking dirty to him.

She talked to him about how I was there to help. How I was there to make further use of his ass. How I was a hot shemale like herself and how I wanted to take out my cock from my panties, line up my shaft with his rosebud, and jam my meat into his ass. That was enough for him. All that teasing, all that spanking, all that caressing, and just the fantasy of being done by a shemale sent this stud right over. That big beautiful cock of his began pumping out his cum for all he was worth. He made a beautiful mess on his Goddess’ latex skirt. Of course, he then had to lick it all clean. And then he had to kneel before me, worship my feet, and apologize for cumming without permission. Yeah, I was turned on alright. I was also hooked.

After she’d dismissed mister studmuffin, Suzy turned to me (no Goddess stuff between us girls) and started playing with the fire she’d set in me. Soon enough I was down on my knees with my face buried between her latex clad thighs and working my lips up and down her cute little cock. She’d been on the juice long enough that her pretty little bit of meat never really got hard enough to fuck with but it did get turgid enough for me to wrap my lips around it and make her coo with pleasure. She eventually laid me on my back, brought her lips to my shaft for just long enough to get me hard and get me wrapped, and then she moved forward and sank herself back down on it. She was using me as a human dildo and this was the first time I’d had my cock inside anyone in over two years. I’d almost forgotten what it was like to be the one doing fucking. Almost forgot. Odd how some things come right back to you! Shortly, I’d rolled Suzy over on her back and began giving it to her but good. Oh yeah, I was hooked. We laughed about how well she’d set me up – and then we fucked some more.
 

I figured that if this was what could happen in a session then I’d be a fool if I didn’t at least check it out. Also, at $250 an hour – cash – the money was a sweet enticement indeed. So, in short order I was once again at a new job as the “new girl.” This time though, it wasn’t my Java programming skills that was earning me my keep.

Suzy started me off slow. She knew I didn’t know squat when it came to handling men as a pro domme so she had me pair with her as she ran through some sessions with her other clients. She ran a house of her own up off of Mars street (yes, there is a Mars street in San Francisco dearie – it’s right next to Saturn street and also next to Uranus street) just up from the Castro. She’d been looking for a new girl like me to replace one of her other girls she wasn’t happy with. It turns out this one girl had been getting a bit too physical with her clients. Not that they minded this at all but such things inevitably would bring too much heat down on the house so out she had to go. Now that I was the new girl to replace her, Suzy had a bunch of her clients lined up for me already.

It was fascinating stuff. I soon learned that not all of the men who sought this out were as scrumptious as that first stud muffin. Some were downright repulsive. They were however, all clean (house rules) and all very well behaved. Suzy, being the good Madame that she was, insisted on that and kept a couple of beefy gay boys at hand to keep things in hand. So, I felt very secure exploring this new side of my existence and damn if it wasn’t a whole lot of fun!

My wardrobe that I’d brought with me from Back East was nice enough, and it certainly had served me well in the business world, but I soon realized (i.e. when Suzy had gone through my closet long before my first day on the job) that it wasn’t up to par for a newly created shemale femme domme. So, that meant it was time for some shopping! I know, a heavy burden to bear! I’d already known about Dark Garden and Madame S. but now I was able to head over there to do more than just window shop. I couldn’t afford much to start with at first so I kept it pretty basic. But with Suzy’s help I soon was kitted out appropriately to be a little sex kitten and bitch goddess all rolled into one.

Those first few sessions with Suzy were a real eye opener. I got to see how much planning Suzy put into them and how she set it up make sure the client got what he wanted, what he needed, and got it in just the exact amount of time he’d paid for. Usually this was just an hour long session. Sometimes it went for two hours but those were pretty rare. Suzy told me of the few clients she’d had who’d paid for an entire weekend and had her travel with them off to Vegas or New York to be their arm candy and showpiece Mistress for some event. That was expensive stuff and very, very rare. I’ve not gotten so lucky. Yet.

In time though, Suzy and I both felt comfortable enough with my progress that she let me run my own sessions. At first she was my helper. Eventually though, I no longer needed that support and was off on my own. That was work, at times, but it could also be a lot of fun. Yes, some of the things the clients wanted could be strange or, after a few such sessions, could get repetitive. But the money was excellent. Even with the “house fee” Suzy got, the money was still superb. Far better than what I had made punching at my keyboard working for that software house.

Soon my wardrobe had expanded to luscious proportions. Damn, did I ever have fun with that. Lotsa and lotsa silky things, nylon stuff for days, corsets, teddies, bustiers, panties galore, and – of course – shoes. Lots and lots of shoes. Glorious shoes. High heel heaven! Open toed sandals, platform heels, boots, stilettos – you name it. Most I bought for myself to use at work. Some I bought for myself to wear specifically anywhere _but work. Some of my footwear collection was bought for me by some of my clients. That could also be fun.

One man in particular was very fun with that. His needs were specific and they were simple and they were exact. He would be dressed as a little schoolgirl (of a specific school) and be kneeling for me as I entered the room. The beautiful five inch stiletto heels he wanted me to wear would be placed neatly in front of him, waiting for me to step my Cuban heeled stocking clad feet into. The rest of my outfit would be just as specific, just as simple and just as exact. Aside from it always being Cuban heeled stockings, it also had to be a black lace garter belt with a pink rose embroidered on the front center, no panties (of course), all under a very strict and tight black wool knee length skirt, and finished off with a white, starched, full sleeved blouse. Oddly enough, while he specified that my hair be bound up in a bun, my breasts should not be bound in any way and that I was to be bra-less under my shirt. A pair of “birth control” glasses (birth control because they were so damn ugly) would complete my outfit.

He was the naughty little schoolgirl who needed to be thrashed by her headmistress. I would slip into persona even faster than I slipped into those stilettos. I’m not a bitch in my normal life but I sure can play one when the money’s right! Soon I’d be pacing around this bratty little schoolgirl, my heels making a delightful clicking noise with each step I took on the hardwood floor. I’d punctuate those steps by tapping a length of bamboo cane into my palm or upon my skirt clad thigh.

It was a real trip to watch this man immerse himself in his fantasy as I walked around him and went there with him. Soon his girlish defiance would melt into a caricature of a petulant teen and then into a scared little girl who was soon begging not to be punished. All to no avail however. At the right point, after enough pacing and berating, I would soon have this nasty little girl bent over my desk for a proper thrashing! This to was detailed and exact. I’d have this “schoolgirl” bent over the side of the desk (we had a room fully set up as a classroom, another as a nursery, another for “doctor’s examinations,” another as a corporate office, two rooms set up as a sissy dressing room and, of course, the requisite dungeon space as well) such that I was standing beside him as his head was on the desktop and his face mere inches away from my crotch – close enough to see the outlines of my “un-girl-like bulge.”

I’d make a wonderfully drawn out process of raising his little schoolgirl skirt and then make an even bigger deal out of just how much of a slut he was for not wearing any panties! With one hand laced into his hair and holding his face in place, I’d then begin to cane his cute little ass for all the “wrongs” he done. He was quite experienced at this and not only did he have a high pain threshold but he also had a rather leathery ass from all the other thrashings he’d gotten over the years. This meant I could continue canning his butt for some time. It took some practice on my part to time it right and to gauge how he was holding up but I usually could do so pretty accurately by watching his body’s reactions and listening to how short his breaths were becoming. His babbling apologies for being such a bad girl were usually not the thing to go by as he liked being able to cry that way.

Finally though, I’d relent and fold his skirt back down over his ass, stripped as it now was. Then I’d have him kneel before the overstuffed chair next to my desk as I “examined” the “filthy smut” he was “caught” reading in the girl’s locker room. This was all part of the scene and it was usually an issue of one of those gay skin mags. The title varied from session to session but it was always one which had lots of big cocks to admire. I’ll have to admit, a number of the men in those magazines had some truly nice pieces of meat to admire!

As I would “examine” this “smut” I’d become aroused by it all. I’d take off my glasses, “examine” some more, and then begin unbuttoning my blouse – button by slowly undone button. Soon I’d be so hot and bothered from looking at that smut that I’d have my skirt hiked up such that I could get at my stiffening cock – what’s this! The headmistress has a cock! Oh no! – and as I’d pull on it, my nasty little schoolgirl slut would creep forward off of her knees and begin nuzzling my oh-so-sexy stilettos. I would sit there with my legs crossed and oh-so-casually dangled one foot in front of his face. He’d become transfixed on my shoes and soon would be lavishing himself upon them with a gusto. I’d put aside the “smut” and begin taunting him with my heels. I get such a rush when I do this.

Soon I’d have one foot pressing the point of its shoe into his balls as he wanked himself under his skirt while I had my other foot up by his face. He’d be holding onto my ankle oh-so-delicately as I allowed him to lick my shoe all over and suck on its stiletto heel. The peak of all this would come when I’d shift feet so that he was now sucking on the shoe that had some of his precum smeared on it. As he did this I’d pull on my cock and taunt him that he was a nasty cum sucking pussyboy cocksucker slut. That was enough. That sent him right over. Every time.

I’d wait for a few seconds as his orgasm would roll through him before I then pushed him off of my heels. There’d usually be some of his cum splashed upon the shoe I’d on his balls. So, as my bad little schoolgirl slut would lay there at my feet she’d get to lick that off of my shoes once again. Then, with my stilettos nice and shiny clean once again, our scene would be at an end. I’d have him get back into his original kneeling position and then I’d step out of those heels just as I’d stepped into them. With that, I’d then leave the room. As part of the scene’s end he would take care of cleaning everything he’d made a mess of. He’d then pack it away in his case – including my shoes – and be off with himself.

Like I said, this can be great fun.

Some of my other clients just want to play dress-up with no SM involved. They just want an hour or so of getting to be “one of the girls” as we sit down with all the make-up laid out and the different outfits they are to wear. Those scenes can be pretty light and fun. There are also the harder scenes I do down in the dungeon room. Those can get real nasty and darkly verbal. But even there, they really are just a slap and a tickle compared to the real stuff. The stuff that I’ve already done or was already done to me. There’s much in the leather/ SM/ fetish world that I do not do with my clients. I separate that so that I have some SM left for me. SM which isn’t associated with the business or with any of my clients. Keeping that separation keeps it real and keeps it fresh.

Fresh as in like the man I have here in front of me. He’s handsome enough and muscular enough. He’s not some huge buffed out runway model stud but he’s tight enough and good looking enough that few would throw him out of bed. Beyond his looks though it is his attitude. He loves tranny girls like me. He’s very, very bi and very out with that. No closets for this boy. He’s also kinky and submissive – and that’s two things I like in my men. Don’t get me wrong – two other things I like in my men is that they be kinky and dominant! But not him. He’s not one of the men who I like to rule men and sweep me off my feet. I’ve a couple of those and they do a fine job of putting me in my place when I’ve the itch that needs to be scratched that way. For the other times though, there’s my pussyboy here.

That’s our play name for him. He likes to be objectified in our play and “used” both physically and sexually. That is more than fine by me! He is pliable to my desires without being some limp dishrag of a “do me” queen. That’s the reason he’s gotten this far and that’s why he’s wearing my collar. We “clicked” together so well that it just felt right for him to give himself to me that way. I like that. So does he. He’s now part of my growing household.

Right now, he’s part of me. Effectively at least. Or at least joined with me. I’ve just spent the past hour working him up. And working him down to. I may be feminized and have a nice smooth and womanly musculature but I can still throw a flogger hard enough and well enough for it to count and he’s gotten pretty well counted tonight! His back is nice and red and marked up. I love the feeling I get from swinging my floggers. They’re very different from my singletails. Those things are more like scalpels to my floggers being like flexible baseball bats. The singletails cut while the floggers thud and for a man with a nice meaty back like my man’s, the thudding is wonderfully sexy.

After good strong beating, I took him down from the St. Andrews and had him kneel before me as I snapped a bunch of clothespins on his nipples and around his pecs. Then I had him put his face down there between my nylon clad thighs. Pussyboy is a wonderful cocksucker. He good at it and he also enjoys it so very much. That’s a good thing for it takes me some time to get nice and hard. Even being on as a light a dose of hormones as I am will tend to do that. But my pussyboy is persistent for he knows that by being so he is pleasing me and that once I’d hard enough there’s other things to do with my cock aside from sucking on it – and that’s what came next.

Popping his lips off my shaft, I had pussyboy clamber up into the sling and I shackled him into it. Once I popped his buttplug out, he didn’t remain empty for long as I soon slid myself into him in its place. His sigh of pleasure and the way his eyes start to roll back into his head as I fit myself into him is something that always touches my soul. Aside from the pure carnal pleasure my fucking him gives me I also know the connection it gives him and that’s one of the reason we’re so close.

Working myself into position, I begin to slowly draw out the fucking. We both love this and are enjoying the rewards that come with having worked up to it so well. I lean forward over him and begin to slowly remove the clothespins on his chest. Each one that I pop off makes it own little zinging addition to the wonderful sensations already swirling around his body. For his part, he begins to caress my breasts and nipples. I’ve left just enough slack in his bindings for him to do that. I do love having my tits played with.

After a good long while of this, I begin to pick up the pace of my fucking my man. I always have to choose my heels carefully for this as I put a lot of pressure on them as I buck into him. Breaking a heel now could be dangerous!

Soon though I’m holding on to his thighs and slamming into his ass. The impacts from my pounding him are shaking his entire body as he lays there in the sling and they make my tits bounce and sway along with the rhythm. With just the last clips left on his nipples he’s soon begging me for permission to cum. I’ve trained him that well that he’ll keep himself at that edge until I tell him to go over it. He usually doesn’t have long to wait.

After enough pounding and bouncing and tweaking of my nipples, I’m there too. I tell him to start working his cock and he takes one hand off of my tits and wraps it around his shaft to start pulling on that. I pause for a second, lean in, take hold of those two remaining clothespins and bring my painted lips to his mouth. His breath is ragged as his eyes heavy with lust, as our mine. My tongue parts his lips and buries itself deep in his mouth. He yields his mouth to my tongue just as he has his ass to my cock. I pop those clothespins off of his nipples and suck his moaning cry deep into myself.

Coming up for air, I rear back and begin really pounding his sweet ass. His hand is a blur as he pounds his cock. “Now, my pussyboy. Now. Cum for me now!” I tell him through my clenched teeth as I too roll over the top. Our climax is so sweet. So deep. So powerful. I love making love to my man like this.

Falling forward onto him, I rest upon his chest and lazily come back to earth from my climax. I love feeling my cock still inside him, listening to his heart beat as he too comes back to earth, and using my hand to idly finger his cum that was spattered onto his chest. Usually, there’s enough for me to rub onto my tits and coat my nipples. He has to be ginger in licking them clean as they become quite sensitive once I’ve climaxed. Yes, this is living the life indeed.

As good as this life is, I’m not quite ready to set up a “house” of my own. I’ve seen the administrative headaches that Suzy goes through keeping her house up and running – us girls can be a real handful at times! No, the household I’m in the process of setting up consists more of a group house with my immediate partners. So far there’s pussyboy here, he is my primary, and there’s also slutgirl, she’s my secondary and is also a real girl – pussy and all – who enjoys a tranny girl like me about as much as I enjoy lapping on her sweet, sweet pussy. That is, after I’ve singletailed her back and ass long enough to get that pussy nice and wet. Then there’s pussygirl.

Pussygirl is a first for me. I didn’t think I’d be attracted enough to the idea of having a tranny girl like me around. We’re a solitary lot in many ways. I certainly didn’t think I’d cotton to idea of feminizing a man down the path similar to the one I was forced down. But there’s something tremendously arousing to me about the idea of a man sacrificing so much of his masculinity to my dominance and control. I’m not sure where this will wind up or how far it will go. I’m certainly not being cruel or deceptive like my ex was with me. Pussygirl is a consenting and equal partner in every step of his feminization.

So far it’s just been the normal hormone routine along with some strict dieting and even stricter corseting. I’ll admit that it is tremendously useful having a live-in domestic like pussygirl. The house is spotless and she’s become a pretty good cook, albeit under pussyboy’s help as he’s an excellent cook. Right now I’m not sure which of my three submissives has the better deal.

Pussyboy, being my primary, has the closest access to my heart but he has no exclusive access to my cock. He has to share that with slutgirl and, occasionally, with pussygirl. For her part, slutgirl now has two tranny girls to hang with and play with along with pussyboy’s full-on masculinity when she’s of a mind to it. For her part, pussygirl is living her dreams of being dominated full-time, being a service submissive, and being feminized in a detailed and loving manner as well.

For my part, I’m just living the life. I’d no idea that my being sissified and winding up with a nice set of tits would serve me so well. Especially once I took back my life and lived it on my terms once again. I do still think of my ex, every now and then, and wonder how she’s getting on. It’s been a few years now. From what friends I still have back there, and from my more recent friends who’ve traveled through there, I’ve learned that my ex has now gotten even fatter and more miserable since I left. Pity. I guess she really threw herself into her job once I was gone. It also seems that dear old Steve is no longer with her either.

We actually crossed paths a year or so ago. He was out here for a vacation and had found my listing on Goddess Sabrina’s website. He recognized me straight away. Actually, I don’t know whether it was that he recognized my face or recognized my tits, he always loved my tits. In any event, that meeting was a tad strained, but we did catch up with each other and how our lives had changed. He left my ex within a month or two of my having cut out. She’d gotten even worse and more vindictive. As I wasn’t there, she had only him to take it out on. Oh well, poor Steve. I was even flattered when he made a pass at me. But I demurred. Too much had changed and to much water had flowed under that bridge. I was also a very different person now. I think that may have been what turned him on so much. I’ve gotten able to tell with some men. The feeling I was getting from him was that he wanted me to be the one holding his ankles up. Well, such things are better left in the past.

So, we bid our goodbyes and parted at that. He went home to his life and me, I went back to living my life - living the life. And let me tell you, for a tranny girl like me, with tits like mine, in this city, and with my kinks? Hell, living the life is good!