Little Big Man

May 1, 2024 // By:analsex // No Comment

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A series of stories with transgender themes which I hope will be of interest to those who like women, or would like to be a woman. Which includes me!


It really is difficult to believe. Out of such chaos and misery could come such bliss. The misery was quite a while ago now, that fateful day when I arrived home devastated. That afternoon old Gilligan had called us all in, the whole sales team. The company had decided to restructure and we were out. All five of us. Out on our ears, with immediate effect.

“The weekend starts now,” he had said. “And don’t bother coming in Monday.”

Sacked, at my age. OK, the other four guys, none of them was over 25 but me, well, I was ‘over the hill’ at 35, certainly in this trade, what chance would an ‘old man’ like me have of finding another job? Certainly not in Hackfield. Most cities may have two or three other possible businesses where I could use my skills but not Hackfield. It was Gilligan’s firm or nothing.

I had to hand in the keys to the company car, and take the bus home. What indignity. Walking down the road towards the house I wondered what I was going to tell Leslie. But it didn’t matter. I called out as I opened the door – no reply, maybe she was visiting someone, even shopping perhaps. I opened the door to the lounge. And yet more disaster, the ultimate disaster I had always dreaded, faced me.

There strewn across the floor, were my clothes. Not my suits, my sweaters, pants. My ‘other’ clothes. My dresses, bras, panties, and my makeup bottles and tubes and my shoes and my padding. Leslie had found them. Obviously. Hell, and my photo album. They were ruined, all ruined. The dresses were torn or cut, the tights were ripped, the make-up was all in a big bag, tubes opened, everything smeared and mixed up. My shoes had been broken, all the heels had been hit with a hammer or something. And my breast-forms, my prize dressing item, they were cut and pulled apart. Un-usable, the lot.

And in the middle of all this mess, in the middle of the lounge, was a letter. Addressed to ‘Mike – or – whoever – you think – you – are’. I opened the envelope. Loads of cash fell out, all in fifties and hundreds. I counted them, several thousand. What the heck?

I looked again, there was a letter.

‘Mike. You disgusting pervert. So this is where all our money has gone. Here is exactly your half of what we have left. Get out of my house before nine o’clock or I’ll use my half to pay someone to beat you so senseless. How could you, you bastard? L.”

No ‘love from Leslie’, obviously.

I looked again, she had torn several sheets out of the photo album. All showing me in varying states of undress, usually with really tarty make-up, shoving one of my dildos or something else similarly shaped up my ass.

This was it. The end. I had three hours to get out. I could do it of course, grab a couple of suits and so on and go. But go where. And then do what? No job, no wife, no house – it was hers, inherited from an aunt. I just sat there and felt very sorry for myself. Finally I knew the only way out. I walked back into the hall and opened the small drawer by the phone and took out my gun. I went back into the lounge, sat on the floor surrounded by the remains of all my finery. I put the barrel into my mouth and pulled the trigger.

It clicked. That’s all, it just clicked. Then I noticed the ammunition clip was empty. I checked in the drawer again, she had not left me even that way out, she had taken it. I sat down again in the middle of the lounge floor and looked round. It was not all there. All the stuff I had hidden in the loft was there, all in tatters or ruined.

But – a small ray of optimism. My new tart’s outfit stuff wasn’t. I’d left it in the garage, well out of the way behind some old tools so that I could get at it that weekend. When Leslie had been due to be at her mother’s, when I had been going to dress up really sexy and do disgusting things with my new maxi-dildo. I’d got all the stuff out of the loft – maybe Leslie hadn’t found that.

I rushed into the garage and pulled the tools out of the way. The two bags were still there, untouched. I dragged them out and into the house and up to the bedroom. It was at that point that I think I became rather mentally unhinged. I remember everything I did but I can’t for the life of me explain why.

It was because a single realisation came to me. No job, no house, no wife. Nothing. In a way I was free – suddenly – from convention. Heck, I’d just tried to commit suicide, that was certainly unconventional. My thought processes seemed logical to me though I do realise now I was definitely unhinged. I seemed to be moving automatically. In the bedroom I stripped. In the shower I smeared Leslie’s depilatory cream all over my body and watched my light brown body hair sink down the plughole. I’d always thought of removing all my body hair but I had always chickened out, afraid of what Leslie might say.

I dashed back into the bedroom with the bag and pulled out the new breast-forms I had bought from one Bostancı escort bayan of the bags. Totally unrealistically I had wanted, in the privacy of my own house and alone, to show the biggest pair of boobs I could possibly get away with. By that I mean which I thought I would look good in, me with my slightly warped and twisted mind. Which is why the breast-forms were a little on the large side. I had measured them earlier, I thought I’d end up with 48-DD boobs. Not just big, but very big.

I unwrapped them and smeared the adhesive over the back, then lay back for a few minutes to allow them to adhere to my chest. I thought I had better put a bra on while I was still slightly lying down so that standing up wouldn’t put too much strain on the adhesive. I had my silver 48-DD bra ready.

The next hour seemed to fly by, again I remember absolutely everything I did but have little real idea of the thought processes which went through my head. But I have an over-riding image in my head, at the end of that time, of sitting on the stool in the hall, looking into the long mirror there, and trying to dial the phone with my long nails. Long vermilion nails that is, a deep bright red color and long, nearly an inch longer than my own. Totally impractical but I still have the memory of extreme satisfaction in wearing nails which went with the rest of my ‘look’. Over the top, that was the idea.

I looked so very over the top. I had never been of the opinion that I could make a convincing woman when I was dressed. Too tall for one thing, just six foot. OK I know there are quite a few women that tall but they are mainly sensible, very few have a penchant for stiletto pumps with six-and-a-half inch spike heels. I did. As I looked in the mirror I liked what I saw, even more than I had done in the past. The shiny black patent pumps showed off my long legs well, as did my sheer black seamed stockings. As I sat there listening to the dial tone for a few seconds my eyes moved upwards in the mirror, over my long sexy legs, past my knees, across the smooth acres of thigh exposed by my too-short skirt. I smoothed my stockings, revelling in the experience as I watched my red-tipped fingers oh-so smoothly sliding across my nylon-covered flesh.

“Er – hi there. Can I have a taxi please? Yes, as soon as possible. Yes, that’s right”.

I gave the girl on the line my address, placed the receiver down and waited. I knew the taxi firm quite well, Leslie and I had used them a few times. They were quick, the girl on the line had said less than ten minutes, I knew she would be right. I stood up and looked again into the mirror, my gaze continuing to scan upwards. Past the high hemline of my tight black leather micro-skirt, past the tight silver top which hugged my figure closely and showed it to best effect.

And what an effect. The tight top over my bulging tits, the low cleavage revealed, I was delighted with the results of the ‘make-over’ on my chest with the new bulging boobs, the smoothness of the surface covering the edges where the breast-forms met my own skin. I looked carefully, I just couldn’t see the join. I had ‘real’, massive, tits! Wow!

I remembered a comment from the assistant in a trannie shop where I had once gone for a make-over – Harriet, I think her name was. I had tried to get her to tell me just how good I did look. She had been reluctant, then I realised she hadn’t wanted to lie but didn’t want to put off a potential customer. Finally she had come clean, basically saying that I was too tall and had the wrong sort of face to be really mistaken for a woman.

Maybe sitting down she had said, and certainly not in daylight. I had thanked her for being honest, she had finished by telling me to keep away from high heels. I almost told her ‘I’m a transvestite – I can’t’, but I didn’t say it.

As I heard the taxi pull up outside I glimpsed my legs again in the mirror. So much for Harriet’s advice! I checked my make-up once more. The long smooth blond-ish hair, the very carefully over-made-up face, I liked what I saw. Obviously. I had gone too far with the make-up but that had been deliberate. Quite heavy over my face, black eyeliner, thick false eyelashes with deep coal-black mascara. I had even shaved off my own eyebrows and replaced them with careful application of eyebrow pencil. The full effect, offset by thick gold hoop earrings, a wide gold choker, three bracelets, five big heavy ‘gold’ rings on my fingers. I looked good. But then I would think that wouldn’t I?

Just for once I didn’t care if any of the neighbours saw me. This was to be my final exit. Outside my front door for the last time, I checked in my purse, id cards – well, maybe I should keep them. Make-up, Leslie’s letter and the cash, keys. Keys? Wouldn’t need them. I took them out and posted them back in through the letter box of the locked door. Finished. Michael was finished. I turned and strode proudly out to the taxi, head held high, chest thrust out, boobs bouncing, boy did that feel good!

I looked at the taxi-driver, his mouth was open at the sight Escort Bostancı heading towards him but he didn’t drive away. I opened the door and got in.

“OK” I said, thrusting a fifty note at him. “Drive.”

He did. As soon as we got out of the street and round the corner I leaned over towards the driver’s compartment and in as sexy an impression of a female voice as I could manage, which was probably not very female at all, I told him to drive me to the truck-stop just outside Hackfield, on the northern side of the freeway.

I couldn’t see his face but I did hear a grunt from him, a rather disdainful sound. He knew what was going on. I know now why I had chosen that particular place though at the time I really was still on autopilot, just reliving out a fantasy without really considering any sort of consequences. I’d seen a report in the local paper about that place, it had been raided by the cops a month or so earlier and several trannie hookers had been arrested there. Trannie hookers? Well, now that could well be me.

It was getting dark when the taxi pulled in outside the truck stop there. I handed the driver a fifty and beamed at him saying ‘Thank you darling’ in a rather silly high-pitched voice. Totally unconvincing. He sneered at me and drove off. I turned. I pushed open the door – and I went in. I stood there on the threshold and looked. There were about five or six men in there. They all turned to look at me. I froze.

I heard the door close behind me, heard the grating squeak of a badly-oiled hinge, and shivered at the noise. I ‘woke up’. Came out of my reverie or whatever it was. Suddenly I was awake, totally, more awake perhaps than I had ever been in my life. I looked round. Hell!

The guys in there were all looking at me. Not surprising really considering what I looked like. I could just about see my reflection in the plate glass at the side of the truck stop. It was really getting dark outside, the reflection was quite clear. And what did I look like? A trannie, that’s for sure. Far too tall and too well-built for a woman, I was sure absolutely every man in that diner was looking at this totally tarted-up transvestite in disgust. So how the hell was I going to get out of this? How was I going to get out of that diner alive?

I shivered again. There was no way I could run away. The taxi had gone, I was on my own. I just had to, in some way, brave it out. I had never really thought of myself as having courage but it must have taken some nerve to do what I did next.

I walked forwards towards the bar, remarkably steadily considering my skyscraper heels. Looking back I am amazed I did it. My very first outing dressed up. And here I was, strolling down between the tables. It did feel good.

All sorts of emotions washed over me. The main one was simply pride. I was proud of myself. Proud of the way I looked. Proud of being, in some way, a woman. What the hell, I knew I looked like a man in a skirt. A pansy, a poofter, a fag, a guy tarted up, a caricature of a woman. But I loved it. Even the leers from the truckers in there, they began to cat-call as I approached the bar. As a guy I had been average, middle of the road, a nothing really. But as a woman, like this, I was something even if the closest words to describe me were probably ‘trannie slut’

“Well hello there, gorgeous.”

I stopped. I shook. The guy sat at the bar had just spoken to me. He was looking straight at me, at ME! At the slut right in front of him! I smiled rather weakly and took a deep breath, in some way feeling my massive fake tits swell out as I did so. He noticed that! I moved forward again, more confident in my ultra-high heels now, and slid my tightly wrapped bum onto the stool next to him. I sat up tall and proud and enjoyed yet again that wonderful feeling I had experienced so often in the privacy of my own kitchen as I slid one nylon-encased leg over the other.

“Well hello there honey” I purred in as provocatively sexy a voice as I could manage.

I heard myself and thought there and then ‘That sounds pretty good – Michelle’. Michelle? Well, or course. Like many TVs I had chosen a name a little similar to my original name. Michael? Well, right now I was obviously Michelle.

“And what do you call yourself, little lady?”

I heard the mocking mutterings from the other five or six guys in the diner, not very loud but loud enough for me to hear.

“Lady – huh!!”

“Little lady, what a laugh!!”

“Little, that he isn’t, not with those tits eh?”

I tried to ignore them and turned back to the guy who had asked me.

“Michelle” I said, not muttering now, much more clearly, much more confident.

And very daringly I reached out and laid my right hand on his. What the fuck was I thinking about? Well, to this day I really don’t know. That ‘madness’ which had taken me over was still there to some extent. I was still not in total control of my actions, going through the motions of being a trannie slut without really realising it. I was oblivious to the consequences, just acting out Bostancı Rus Escort a fantasy without thinking about it. Fantasy, yes, I got a real thrill as I looked down and saw my own somewhat feminine-looking hands, extra-long scarlet fingernails and all, caressing that guy’s own big gnarled hands.

“And what do they call you, lover?”

Had I really said that? The tittering and cat-calling carried on behind me but this time I didn’t look. Autopilot or not, I was still enjoying myself.

“I’m called Big Mack” he said.

The noise behind me increased, it sounded much more than the few men I knew were really there.

“Hush up you all!” called out Mack, looking past me at the ‘crowd’.

Suddenly it quietened.

“Well, Michelle. I reckon after what happened in here last week you’ve got some guts and I’d like to buy you a drink. How about it? I’ve been on the road for two weeks now and I ain’t getting any and my old woman’s prob’ly shacked up with the bastard from the store she works at. All I’ve done is jack myself off ev’ry night for two whole weeks so I reckon I deserve some. And since there ain’t no others queuing up for me, honey, I reckon you may well do me just fine.”

At which, to my total amazement, Big Mack moved his hand away from mine and slid it up my leg, from just above my knee until it was so nearly sliding up under my micro-mini. I shivered. Hell, I shook visibly, this was SO amazing, I just couldn’t believe it. Had it happened at last? Had I – got myself a man?

“Hold on Mack.” A voice came from behind me. I was about to turn when, out of the edge of my view another man, almost as wide as Mack, moved between us. “Let’s find out what this ‘girl’ is out for. I heard about last week too, the trannie guy was asking twenty dollars a suck and got greedy when somebody wanted to fuck him. So how much is this big tart charging?”

I looked at him, then across at the other four men behind him, still sat, hardly eating, intent on the events unfolding in front of them. They were all, well, nearly all, well built guys. Apart from Mack and this guy, one of the others seemed tall, two of the others were shorter but all of them were big and wide except for the tall skinny guy at the back. Any one of them, except maybe him, was quite capable of beating me to a pulp if he wanted, indeed probably any one of them could kill me with his bare hands. I smiled at the big guy.

“So honey, what’s your name then?”

“He’s Fat Jack” butted in Mack. “Hold your horses, Jack, I’m first. I can see your snake is getting excited already bit you can wait your turn, I’m first.”

He turned and spoke to me, again putting his hand on my leg and this time sliding it just a little up under my skirt to reveal my stocking tops and a hint on my bare thigh. I looked down between Jack’s legs, then at the same area below Mack’s belt and realised. These guys were all excited. Both their cocks were getting larger. And I had done that! Whatever else happened, had done this, got these two men aroused and in all likelihood the other guys too.

“Well Mack, I’m not greedy. Not for money anyway. How about buying a girl a drink? A gin and tonic and then I’m yours.”

Mack didn’t need to be asked twice, he looked towards the guy behind the counter who moved quickly and then put the glass down in front of me. He raised an eyebrow at Mack, then went back and came back with a large bourbon which he handed over to Mack.

“Cheers” I said, smiling, raising my glass towards Mack and drinking deeply.

I was ready for that. I usually drank beer, never was too hot on harder liquor, but this time the G and T seemed more suitable. Mack took over half of his double down in one go and then reached over to touch my neck ever so gently, though he wasn’t so careful when he slid his hand down and over my ‘breasts’, and then had a feel down in my cleavage.

“Now, darling, take your time” I cooed, trying to look and sound sexy.

But Mack was not so keen to wait, he was aroused and in something of a hurry. He squeezed my right breast and got up off his stool, reaching to grab my right hand and drag me after him towards the corner of the bar. Not private, not secluded, but not quite so on display as we had been sat up at the bar.

I was new to this but I had fantasised about it so often that I knew the drill, or at least I knew one version of it, the one I had read about in so many stories and dreamt about so often. It started with a kiss. I was ready for that as I sat down next to Mack and his big meaty hand settled yet again on my thigh, this time sliding up even further than before. He looked down sat my exposed stocking tops, at the garters holding up my sheer seamed stockings, and groaned.

“Christ. Michelle or whoever you are, you do sure as hell turn me on. I haven’t felt so horny in years. Come here!”

I was kinda ready for anything at that stage, but not for the ferocity of Mack’s advances. Within seconds he had pulled me on top of him and grabbed my ass close to him so that my tiny thong and my bulging ass-cheeks were exposed to the world. Or at least to all the other guys who had moved up closer to our corner so they could watch. Mack buried his face in my neck, nuzzling me hard with his lips and his unshaven chin, then pulled my top away from my shoulder to reveal my very ample and well-filled bra cups.

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