tagTranssexuals & CrossdressersDoes My Bum Look Big in This?

Does My Bum Look Big in This?

byTomsparty©

I became aware of my girlfriends strange fascination within weeks of us meeting. My bottom - It really turned her on. It seemed strange at first. I thought most women responded to a number of triggers like eyes, hair and muscle on a man. The list is long but in the case of my Melanie's it includes bottoms. She's quite specific in her taste: She likes round, fleshy bottoms - not what I would imagine women to prefer. Mine, though acceptable, was according to her too thin and firm. I guess you could say too manly. But what did she expect? I was a man after all. OK, not a manly man but nevertheless a man. She preferred rounder feminine bottoms – which threw up serious doubts about the stability of our long-term relationship and yet she repeatedly reassured me that I was her type. Like any man I thought her quirk was a bit twisted but I didn't really mind. She was beautiful and I was in love. Her many features far outstripped her kinks. She was a stunner, tall, slim, fabulous figure and a beautiful soft face framed with long straight blonde shoulder length hair.

To be honest I found all her attention rather flattering. Just as men like tits and legs. Melanie was a bum woman. Apparently it was the first thing she noticed about me when we met - that and my eyelashes. I knew about them as mine, according to Melanie, where longer than a woman's. She was observant like that because of her job - a beautician at a fashionable salon in town. Long eyelashes are as intrinsic to beauty as bone structure and flawless skin she said. I had that too, flawless skin, according to her but I was sure these where not the only reasons she dated me. Yes, before you wonder! We had an active sex life too. She had a ferocious appetite outstripping me by far. It was always fun and she was forever teaching me new techniques. Yet she was forever fascinated with my body. She was obsessed. As if she can't sleep, she can't eat or she cant breathe. She thought of nothing else. When I questioned her she said ' Obsessive love is like living out the thrill of a life without boundaries.' OK I thought. Why worry. She fancied me. I fancied her and we had great sex. Their wasn't a problem or so I thought.

One night after sex she droned on and on about my bum and eyelashes.

'If you could design your fantasy face you'd almost certainly max up the lashes,' she said 'Take Barbie's for example, which virtually graze her eyebrows.'

She was so proud of me - she wanted to introduce me to all her girls at the salon. Yes I was flattered yet I thought it was for the wrong reasons. She didn't talk enthusiastically about my male characteristics but more about aspects of me that where deciding girlish. She was persistent but I always declined. 'Meet me after work for a drink or pop in at lunchtime.' She would ask but I didn't want to be shown off like some trophy especially when what she considered my most redeeming features are not what I'd consider manly. Soft skin, flawless complexion, long eyelashes, hippie bottom - these are just some of the descriptors you wouldn't use to describe an ideal hunk of a man. I know I didn't posses a six-pack or a trunk like neck or rippling muscles of steel but I didn't want her friends to think of me as weedy an effeminate..

On recollection, I was probably my own worst enemy, as I would frequently let her use me as a model to try out some new product for work. Why she couldn't put it on herself I will never know. I would sit patiently at her dressing table as she amused herself with groovy eye shadow, pearly lipstick and eyebrow pencils. I normally let her have free reign but one day she got so carried away she tweezered my eyebrows into a feminine arch. She said brows are the defining feature of any face and without plucked eyebrows, the drawing is incomplete. I wasn't so sure. In fact I was mad, terrified everyone at the bank would laugh but Melanie was delighted with the result. Instead of apologising or attempting to cover it up she insisted that she maintained them that way and sure enough she incorporated it into what she called 'my beauty routine.' This seemed infuriating as she used to preen and pamper me more than any woman. It all seemed very high maintenance. She even tampered with my hair which I thought was a great natural colour and nice and thick but she was never satisfied and she would put lowlights then highlights in it as well as make me grow it to almost shoulder length. According to her I was the reason for her success at work.

She wanted to keep my canvas perfect and consequently every night she smeared soft cream on my face and gave me a manicure and pedicure weekly. She always did a great job initially I found the whole experience unnerving but as the weeks rolled by and her beauty sessions became routine I began to enjoy the routines especially when we nearly always ended up having sex. Weird but It really turned her on to see me all pretty.

Overtime I changed not just in appearance but also in attitude. I was never a rough type but slowly I was turning into an incredible softy and was concerned she was pushing me to social suicide. With dyed hair, arched brows, soft skin and manicured nails I was looking increasingly feminine. The strangest part was my acceptance of it all. I liked the attention. I liked to look pretty and please her. To be honest I had few close friends so I really valued our relationship and would be heartbroken if we where to split. Desperate to please her I found myself self subconsciously looking after my nails, hair and skin, avoiding what I considered dirty work.

I guess I had a rough time at school. I was always slight and feeble with hardly any muscle. The boys bullied me and the girls would laugh at me. They said I walked like a ballerina. I never had a girlfriend of any seriousness so meeting Melanie turned my world upside down. I felt so lucky. I adored the attention and learnt so much from her. She was such a strong character I simply couldn't resist her and why should I worry if she was changing me into a sissy when all I wanted was her attention. If this is what it took I was prepared to rough the journey though it wasn't until later did I found out how long and arduous the journey was to be.

All this body attention was interesting but she never strayed far from the topic of my bum. It was always her main interest and when ever in bed she would always stroke and fondle it. Of course I never objected, who would, though I did consider it rather odd. She treasured it as if she owned it and with my hair and face sufficiently girlish over the weeks she became obsessed about its shape. She would compare it with the arse of celebrities and became increasingly dissatisfied. I even believe she found cellulite attractive. Her major grievance was its size. She was convinced I'd lost weight and took it upon herself to fatten me up. Not in the all over sense but she seemed obsessed in increasing my buttock size. She made me do yoga and perform strange exercise and eat all manner of weird foods. She even spanked me with a wooden paddle. Insisting it was good for the blood vessels. I was embarrassed at first especially when she wouldn't allow me to spank her. Yet I enjoyed the submissive role. I loved it when she tore my pants down and spanked me over her knee especially if she had painted my lips with lips stick and coated my eyelashes with mascara and shaded my eye lids with shadow. The feeling of her hard handing crashing down on my soft bottom was a thrill. And sure enough overtime I did put on weight. But not all over as I would expect. She knew her stuff and oddly I began to change shape. My waist became smaller, my legs and thighs slimmer and my chest and arms shrank but to Melanie's immeasurable delight my hips and buttocks grew and grew. There seemed no stopping them and as they grew the regime of spanking, exercise and diet intensified. She measured them weekly and kept a record in a notebook like a train spotter but when ever I complained she would look at me with her puppy dog eyes and I'd submit. I was powerless.

One night after being made-up to look like a Barbie doll with my hair in pretty bunches and my bum stinging from a particularly hard spanking session after tremendous sex we lay on the bed exhausted. Without saying a word she rolled me on my front and began to knead my buttocks like bakers dough. I drifted into a dream like state as her fingers danced over my arse like wild butterflies. She talked constantly and for the first time confessed how she wanted to see my bum in something lacy and skimpy. She said 'a glimpse of bum in something sexy is a promise of sensual riches - a pleasing sight.' I blushed but immediately imagined myself in something soft and sensual. I should have guessed what was to happen next. It wasn't a surprise. Her intention was to make me wear her lingerie. She thought my rounded bottom was more suited to lacy panties than my normal briefs. As normal I didn't object as she suggested which of her panties she wanted to dress me in. As she teased me her caress got more frantic. Tiny thongs, slinky cami-knickers, high sided panties adorned with bows and lace her descriptions drove me wild.

It then dawned on me my buttocks where no longer firm and muscular but soft and wobbly like a woman's yet I found the experience rather enjoyable. Harder and harder she rubbed until my skin was warm and supple. My mind was a whirl and as she rubbed and talked about her sexy lingerie she widened her repertoire and in addition to panties she began talking about stockings, suspenders, high heels and bras. I loved the sound of her voice, her descriptions and what she intended to dress me in. I was putty in her hands. Then to my delight she smeared a dollop of some cold greasy cream all over my arse cheeks. I jumped with surprise but soon was squirming with delight as she massaged the cream into my skin. Harder and harder she rubbed and as she worked her fingers became more and more inquisitive. Furtively touching between my cheeks until they eventually teased my sphincter. I would object but being so relaxed and hot I let her work away tantalising my glory hole with light brushes of her fingertips. It was heavenly. It came as no surprise when she quickly slipped a greased finger deep into my hole. Without any explanation she paused momentarily her finger nestling inside of me twitching slightly like an inquisitive probe. She pushed it deeper and my cock stiffened as if about to ejaculate. Feeling my mood she pumped her finger slowly in and out like the piston on a engine. I couldn't resist squealing and to her delight I didn't object. To the contra I was soon pushing up on her finger and moaning like an excited teenage girl. It was a first and I never imagined I would get so much pleasure from being penetrated from behind. To be honest I found the whole experience rather embarrassing. It just didn't feel natural but natural or not I eventually shot another load all over the sheets and Melanie hugged me as if I'd just got promotion at work.

That was the beginning. Anal penetration was added to our long list of love games and she kept telling me how lucky I was to have such a sensitive arse. More surprises where to follow. Unhappy with my weight gain she injected my developing bum cheeks weekly with some strange substance she got from work and when she had a little over she also injected my lips. That hurt and they became very plumb and full. She said it was only temporary but that was 3 weeks ago and I still look as if I'm constantly puckering for a kiss. It was true they look incredibly sexy when Melanie coated them with pretty pink lipstick but come on... how far was she intending taking me?

After a few weeks panties became part of my wardrobe as mush as hers and we ended up sharing the same top draw as she threw all my underwear away. She loved me to wear clothes that displayed what she considered my best assets. She'd turn up the heating in our flat and make me wear just her panties. She would love to see me sprawled on a chair in front of the TV in nothing but her tight panties - sex invariably followed. She couldn't keep her hands off me... so why should I complain. But all this attention was creating a few other issues. With my increased bum dimensions my own jeans and suit trousers began to show the strain. Melanie got such a thrill from what she called MVPL (male visible panty line) when I wore my suits for work. Even a few of the cashiers began to notice. She tried to alleviate the situation when one Saturday after I couldn't button my favourite jeans she treated me to a new pair. Made by my favourite designer they fitted perfectly. Yes they hung lower on the hips than normal and there seemed less room for my cock but other than that they fitted in all the right places. Melanie was thrilled. It wasn't until weeks later that I noticed they where a size 14 and designed for women. I should have guessed her game then but I was hooked and she was reeling me in like a hungry fish.

Her constant attention to my arse had transformed its skin to something reminiscent of a infants bottom. Hairless and remarkably smooth my skin had developed an amazing sensitivity that felt the slightest touch. I had even developed an appreciation of delicate fibre and now hated course trousers. It was while I was in the shower that Melanie commented on my legs - I had soft, downy hair on my legs which Melanie felt looked odd against my smooth soft buttocks and I should consider waxing. I laughed - of course but she knew I'd do anything to please her and after I'd dried I found my self lying on a soft white towel on our bed as she stirred the wax in one of these home waxing kits with a wooden spatula. She took her job seriously and wore her sexy white beauticians dress. She knew it turned me on as I could clearly see the outline of her own sexy lacy panties and bra. She also played a CD at the time and burnt one of those smelly candles. I felt quite relaxed in a girly sort of way but the whole experience was agony. She said I was tremendously brave and suggested while she had the equipment out she wax my back and chest at the same time. I didn't refuse. According to her many of the men at her gym wax. Needless to say after she had moisturised me all over paying particular attention to my buttocks we had the best sex ever.

Exhausted and flaccid I lay on my back gazing dreamily at the ceiling. We had drunk ourselves silly and I was off my face. I couldn't remember much about anything. Melanie was talking gently and though I felt her jump out of bed I barely noticed her slip a pair of panties up my smooth legs. I didn't even smell a rat for I'd been wearing them for weeks. They felt sensual, soft and incredibly light. I lay still and ran my fingers over my new undergarments. I felt the prickle of lace and a tiny bow in the centre of my waist. I smiled with delight as I realised she had also waxed my pantie line. I propped myself up on an elbow and looked down at my feminised torso. The panties where gorgeous. They where a soft, subtle shade of pink, semi transparent and adorned with white and darker pink flowers. A month ago I would have torn them off angrily but I felt strangely comfortable and secure. She asked me if I liked them and before I could think straight I'd agreed. I sat upright my soft cock barely noticeable in her panties. Sure of her footing - convinced I wouldn't object she slipped my arms into a matching push-up bra and clasped me up before I could utter a word. I was speechless as she padded the cups with handfuls tissues then plumped them into a convincing shape. My breasts were enormous but they accentuated my hourglass waist and shapely hips. Confused I swung my legs off the bed as she rummaged in her stockings draw. Next I watched transfixed as she rolled a pair of sheer tights up my legs. They felt amazing on my new super smooth and moisturised legs and my cock began to spasm excitedly as the soft tights caressing my smooth legs drove me wild. I didn't object. She fussed around me like a mother hen and soon I was wearing a pretty camisole, skimpy half-slip and a beautiful light floral dress that clung to my every curve. The dress was a surprise – even at this stage of my transformation I didn't expect to have to go the whole way. But tonight she seemed determined to complete my feminisation. If this was the journey she seemed determined to gallop the last few furlongs.

The dress was stunning and very flattering. I'd never seen it before though she insisted that she hadn't bought it specially. It was of a gorgeous silky fabric, incredibly light and floaty that stretched perfectly over my curves. I barely noticed it on. It fitted perfectly tight round the waist, perfect round the bust and hung from my large hips as if made for me. According to Melanie it was made from 'power-mesh- which shapes curves and creates a super-smooth line. I had to agree - it had me powerless

Delighted with my acceptance she held me lightly by the hand and guided me to her dressing table. I sat on her stool, automatically smoothing my dress under me as I sat. Melanie smiled kindly. She slipped my feet into some cream coloured high heels and buckled the tiny straps round my angles. I'd never worn women's shoes before and they felt gorgeous accentuating my shapely angles and lengthening my already willowy legs. She made up my face and pulled on a beautiful shoulder length blonde wig. Thirty minutes had past since we made love but in that time I'd been transformed into a pretty young girl. The moment I was shown a mirror and my new look was revealed was a little bizarre. The transformation was like magic. I felt like a waxwork model with my new beautifully made-up face, feminine clothes and long slender legs perched in towering heels, but remarkably I got used to everything quickly - the dress was so comfortable, the panties really sexy and the taste of fuchsia pink lipstick on my swollen lips practically drove me wild. As a joke I slipped on her huge sunglasses and minced around the room wavering my arms limply around my body criss-crossing my legs like a catwalk model. It was then I felt my eyelashes brush against the sunglasses and realised shed added mascara to make them even more dramatic. I turned my back on her and bent at the waist holding my knees. I shook my bottom and felt the flesh wobble and the hem of my skirt flutter like butterflies around my knee. Melanie was amazed. 'You look beautiful,' she kept telling me. 'Your lashes really open up your eyes. You're so pretty there is no denying you'll get the lions share of the male attention.'

What came over me was a mystery. I was putty in her hands. And knowing as much I worked my new feminine personality hard, affecting Princess Diana gazes here, Disney doe-eye flutters there. I felt so pretty and confident. 'I could become addicted to dressing up,' I gush performing a spectacular twirl in the centre of the room. We both gasp as my skirts flutter upwards and Melanie captures a glimpse of lace panty.

'Oh darling!' she cooed 'I knew you'd find this fun, we're so alike without them you're simply naked.'

'Them?' I question.

'Make-up skirts, tights, bra, heels, the whole wardrobe I just couldn't live without my pretty things and I'm so glad you feel the same.'

Why I felt so girlish was a complete surprise but I felt gorgeous, romantic sexy and totally emancipated. I could see her getting excited so I happily obliged as she bent me over the back of a chair. With my plumb backside proud I felt vulnerable and yet I trembled with anticipation. She ran her hand over my bum softly, her fingers teasing my crack. I gasped as she slides my skirts slowly up my back, cm by cm revealing my tights and panties. I blush wishing I'd worn stockings - I ask you! Stockings! What had become of me? Melanie made me hold my skirts high round my waist as she eased my tights and panties down a few centimetres. I didn't know what to expect - just enough to slip a well-greased butt plug into my hole. Satisfied she let my panty elastic snap back and my dress fall gracefully over my hips as if poured like cream over strawberries.

Report Story

byTomsparty© 19 comments/ 179577 views/ 22 favorites

Share the love

Report a Bug

Next
2 Pages:12

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel