• Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Maid to Order Ch. 01

Maid to Order Ch. 01

12

Michele Ascending

My wife had left me a year ago. I'm surprised she waited as long as she did really. We were married when we were both eighteen when I was in the army. She had been my only girlfriend and I was scared she wouldn't wait for me because I was being deployed overseas. It was a whirlwind romance.

I'd heard rumours that she'd been a bit loose before we were married. I remember one of my mates down at the pub on my buck's night talking to another bloke, not knowing that I could hear what they were saying.

"I'm surprised Mick's marrying Cynthia. She's had more pricks in her than a second-hand dart board," he scoffed.

"Fuck! I remember way back in Infants School; she'd show you her knickers for a bite of your toffee apple," the other responded, laughing wickedly.

"My Uncle Stan reckons they'll bury her in a Y-shaped coffin!"

They both broke into peals of laughter and then one of them saw me and digged the other in the ribs and the laughing stopped.

Call me naïve, call me stupid, anyway I married her. I lost my virginity on my wedding night; well sort of.

I'd always had a fetish for nylon stockings, tights and silk and satin knickers. I started wearing my mom's and sister's knickers and hosiery back when I was ten or twelve; I had quite a collection and I'd wear them to bed feeling wonderful with the silk, satin and nylon caressing my body. Then I knicked a satin full-slip and wore that as well; that's when I discovered the joys of masturbation, and in particular masturbating while wearing hose, knickers and the slip.

My sister caught me when I was seventeen; I'd drunk some illicit beers with a couple of mates and foolishly went home and slipped into my girly underwear and wanked myself to sleep. I slept in, hungover, and my older sister came into the bedroom and found me. The cow told mom and she told dad and that's when I got the 'You need to join the army son; that'll make a man of you' speech.

At seventeen and a half I'd signed up, with mom and dad's blessing.

Don't get me wrong; I was heterosexual. I loved looking at women, especially when they wore short skirts, which showed off their nylon-clad legs and a tasteful glimpse of knicker and I wanked off furiously to pictures of lingerie- clad women. I'd just never had a real one until Cynthia.

So back to my honeymoon. As I didn't have much money, it consisted of three days and nights at my Uncle's cottage at Hastings but our first night together was in my bedroom at home before we drove down there.

Cynthia had worn white of course, but as we were both skint her wedding dress was a hand-me-down from her mom and was a 'modern' seventies affair with a tight bodice with a short taffeta skirt. At my request she'd worn stockings, white ones with back-seams and lace tops and white high heels.

By the time she made it to the bedroom she was so sloshed she could hardly stand and literally fell on the bed. She spread her legs and looked up at me drunkenly with her smeared makeup and bright red lipstick.

I stared at her bedazzled and fascinated. A woman, a girl really, dressed just how I liked; and she was all mine. My erection tented my uniform trousers.

"Come on then you silly bugger, put it in me I wanna go to sleep," she simpered.

I stood there for about thirty seconds staring at her long stocking-clad legs and gauzy white panties through which I could see her dark bush then I unzipped my fly and fell on her. My cock quivered when it came in contact with her stockings and as soon as it touched the silken gusset of her knickers I ejaculated.

Cynthia laughed cruelly and pushed me off her and fell straight to sleep. I woke up in the early hours and she was still fully dressed and snoring. I snuggled up to her and this time I was able to get my penis inside the gusset of her panties and inside her. It was warm, wet and wonderful and I came in about a minute but at least this time she hugged and kissed me after.

"Good boy," she muttered dreamily, and went back to sleep.

Of course we shagged ourselves senseless during our honeymoon; I was as inept as she was adept when it came to sex but she soon taught me how to do it 'properly'. Like I said, I'd like to think I was more naïve than stupid but deep down inside I knew there was only one explanation for her sexual prowess.

Needless to say I was informed a month later whilst I was overseas that we were going to be 'blessed with a child'. I was home when he was born and even allowing for the 'somewhat premature' birth, I realised that he'd been conceived before I married Cynthia. We just pretended like that wasn't the case and I raised little Joe as my own son. All was ok until just before my thirtieth birthday when I came home unexpectedly and found Cynthia bent over the kitchen table being fucked my best friend.

She didn't even show any shame and just smiled up at me; bent over the table with her skirt hiked up and tights pulled down as my mate pounded away at her.

"Sorry Mick, but this was always going to happen some day," she smirked.

"I'll give you my knickers and tights when Colin has finished banging me; you can add them to your collection, pervert!" she scoffed.

She was as good her word; I'll give her that. When I came back from the pub in the early hours of the morning she and Joe and most of her belongings had gone but she had left her panties and tights on the table next to a note.

'You keep the dump and I'll keep the car, the savings and Joe. I've had enough of you, the army, and your creepy compulsion with knickers and stockings.'

And that was that.

Our twelve year marriage had been one of convenience; I'd been away a lot with the army and I knew she's been shagging around while I was gone, just as she had found out about my knicker, stocking, tights and slip fetish. It was the elephant in the room for at least five years during which we'd hardly slept together. She often stayed out all night and I often slept in the spare bedroom dressed in my tights, knickers and slips.

Three months after she left me I was free of the army and living conformably by myself. Cynthia wasn't as smart as she thought and I'd been squirreling away money for years and having made Sargent before I left the mob, I landed a decent job working security.

Twelve months later a lot of other changes had also taken place. I'd renovated the 'dump' into a nice little townhouse, bought myself a little car and was living quite comfortably by myself. But the most amazing change of all was my very special secret.

Mom, dad, and my sister were disappointed but not surprised at my marriage breakdown. Even my father-in-law Bill felt sorry for me. My family never visited me and that suited me fine. When we got together at their place, mom and dad took every opportunity to express their disillusion with my marriage breakdown and their regret at not seeing their grandson Joe, who they stupidly hadn't figured out wasn't mine anyway. When we were alone my sister would often torment me about the time she found me dressed in lingerie. Once she even lifted her skirt and showed me the dark gusset of her tights and full-cut panties.

"Can't make up my mind if you'd look better in these than me?" she taunted.

"Fuck off!" was the best I could do to retort.

My father-in-law was really the only relative I could tolerate. He tried to get on with me and often invited me to go down the pub with him and I sometimes took him up on his offer. He was quite philosophical about the whole thing.

"You know Mick; I sort of felt sorry for you when you married Cynthia, I knew nothing good would come of it," he commiserated one night after a few too many pints.

"What about Joe?" I asked.

"Come on mate; we both know that Joe was on his way whether you married her or not," and that was that.

We never raised the subject again.

But what I really liked about living alone was that I was able to progress my fascination with crossdressing in secret. At first I just got around in panties and a slip, wearing either stockings or tights; but then I discovered that Cynthia hadn't taken all of her clothes, makeup, and shoes with her. She'd left a small collection of her stuff in one of the wardrobes in the spare bedroom.

I bundled it all up with the intent of donating it to charity when one of the items caught my attention and gave me an idea. It was a black long-sleeved cocktail dress; the fabric felt smooth and sexy to the touch. I hadn't seen Cynthia wear it for years; she'd packed on a few pounds after giving birth and it probably didn't fit her any longer which was probably why she'd left it behind.

I rubbed the fabric against my face; it wasn't as sleek as my nylon and satin lingerie but it still felt exotic and I wondered what it would feel like rubbing against my slip, panties and tights. I turned out the tag and it stated 'size 10, cotton Lycra blend, hand wash or dryclean', which explained the nice feel.

Nervously I locked up the house and closed all the curtains and blinds. Probably overcautious, but I was very trepidicious. I slipped into a pair of tan tights, delighting in the feel of the nylon on my flesh. I stepped into a pair of white satin panties and slid them up my legs and pulled them tight. Those familiar delicious sensations teemed through my body.

My years in the army had kept me fit and trim and as I had a small frame anyway I figured I might just squeeze into some of Cynthia's clothes, especially the cocktail dress which I had laid out on the bed.

I figured that the dress wouldn't need a slip under it; Cynthia had certainly never worn one under it so I picked it up and stood in front of the full-length mirror and tentatively held it against my body. It might just fit!

I lifted the garment over my head as I'd watched Cynthia do hundreds of times and pulled it over my head and pushed my hands into the armholes. I struggled and squirmed pulling the dress down; my hands getting caught in the sleeves and the tight bodice caught around my head as I tried to pull the garment on. Women made it look so easy! I couldn't help but laugh at my predicament but eventually I managed to get my hands out of the cuffs and pull the dress down over my body.

I was finally able to squeeze into the dress and smooth it out over my body. The first sensation I felt was the slinky feel of the hem whispering against my nylons, then the delightful perception of the fabric against my bare chest. It was very tight; too tight, but it actually looked quite good if you just looked at my torso and legs and ignored my bloke's face and unshod feet.

I chuckled at my reflection and I found myself becoming aroused, very aroused. I lifted the hem and looked at my firm thighs where the tan hose gave way to the dark chocolate gusset of my tights. I was wearing my panties over my tights and I pulled down the front of my knickers and saw my hard cock stretching the dark nylon gusset and the curls of my pubic hair through the gauzy textile.

In my mind I blocked out everything above my neck and imagined a lithe woman lifting the hem of her dress, displaying her panties and hosiery. A little wet patch appeared at the front of my tights and I reached down and began to stroke my thickening penis through the diaphanous nylon. A few strokes later my knees buckled and I gasped as a globule of white semen bubbled through my tights. It was one of the most intense orgasms I had ever experienced.

I wiped away the mess with a Kleenex and padded downstairs in my stocking-feet and grabbed a beer from the fridge and sat in my favourite lounge chair smoking a cigarette, drinking my beer, and just enjoying the experience of wearing the dress, hose and knickers. It was not only sensual it was comforting.

Over the next few days as soon as I came home from work I squeezed into the little black cocktail dress and did the same thing. It just felt right wearing the dress, tights and knickers. I eventually went through the rest of the clothing Cynthia had left behind. If this had been a story like the ones I read online about a first time crossdresser, all of the dresses, skirts, blouses and brassiers my wife had left behind would have fitted me perfectly. Sadly that was not the case. I could just squeeze into the cocktail dress but the rest of the clothing was far too small; I even tried to get my feet into a pair of her shoes but I couldn't get my toes further than an inch or two inside them. I did find a bra that fitted but it was uncomfortably tight.

I kept the cocktail dress and the bra and ditched the rest in a recycle clothing bin.

I kept the small cosmetics case she had left behind and one evening my curiosity overcame my trepidation and I decided to give it a try. After securing the house as usual I had a shower, shaved myself closely, and dressed in panties, tights, bra and my full slip I sat in front of the vanity mirror in the bedroom. I had watched Cynthia apply her makeup countless times and was prepared to give it a go. I could see why Cynthia hadn't bothered to take the cosmetics; a bottle of foundation was down to its last few dribbles, the eyeliner pencil was worn to a nub. The mascara was gluggy and the little box of rouge had just about expired, as had the small eyeshadow palette; the saving grace was a brand new pot of finishing powder. A couple of tired looking makeup sponges, pads and brushes completed the forlorn ensemble I arrayed on the dresser.

The whole thing was a disaster. I caked my face with foundation, powder and rouge; for the life of me I couldn't get the eyeliner right and my eyes looked like a panda's, not helped by the gluey mascara cacked to my eyelashes and the bright blue eyeshadow I chose. My lips! Oh god my lips! I smeared the bright red lipstick all over them and outside of my lipline and couldn't get it right. Eventually they looked like the lips I had seen on a golliwog when I was a kid.

I sat in front of the vanity mirror and was dismally disappointed. I looked like a six year-old playing dress-up in mommy's clothes and makeup.

I squeezed into the cocktail dress to see if that would help and stood in front of the full-length mirror. I looked at myself critically in my clown makeup, my ill-fitting clothes, leg hair clearly visible through my nylons, my pathetic unshod feet and short military style haircut, and laughed. Then I wept.

"Pathetic cunt!" I whispered.

"Fucking Nancy-boy!" I croaked.

"Fucking pervert!" I screamed.

I ripped off my clothes and fled to the shower and scrubbed the makeup from my face with a facecloth. I wasn't even dry when I gathered my pathetic collection of lingerie, the dismal assortment of makeup and the too-small cocktail dress and threw them in the bin, purging myself of my pitiful fetish once and for all.

I opened up the house and drank myself into oblivion, swearing that it was the last time I would give into my perverted urges.

My resolution lasted four weeks, then I snowdropped a pair of tights and knickers from the next door neighbour's washing line and put them on. For a couple of weeks I was content to leave it there. But I couldn't get over the immense feeling of satisfaction I had experienced wearing that little cocktail dress.

Being a military man I formulated a campaign, meticulously planning my transformation from hairy panty wearer to full on transvestite. I combed the Internet, visiting the myriad sites offering advice to first time crossdressers. I ordered some breastforms and three wigs from an online provider to be conveyed to a post office box I had rented. I put together a shopping list and drove to a city far from here, even going to the trouble to rent a hotel room so I could stay overnight.

I hit the huge mega-mall first thing in the morning as soon as it opened, going straight to a shoe store. I declined the assistance of the gum-chewing shopgirl who was obviously far more interested in swiping and tapping her phone and drinking coffee anyway, and made my way to the back of the store where the larger size shoes were kept. I wasn't wearing socks and I had a cardboard cut out that I had stencilled from my foot. I tried the stencil against the soles of a few pairs of shoes but it wasn't much help despite the claims of the online adviser who said it would assist me acquire shoes in my size so I went to plan B. Carefully ensuring that no one was looking I kicked off a loafer and quickly tried on shoes until I had three pairs of high heels.

I didn't even need the elaborate story I had concocted for the shopgirl; she hardly looked up from her phone as she swiped my purchases and took my cash.

I left the shop beaming.

I dropped the shoes off in my car and headed back inside to a large department store where I picked up a large cosmetics case that according the display sign: 'contains all the makeup a woman could ever need'. I hedged my bets and made my way over to the lingerie section and purchased a dozen pairs of good quality tights; this time I selected sheer-to-the waist, rather than the ones with the dark gusset. A quick look around confirmed that the store only sold stay-up stockings but I bought a dozen pairs in black and flesh tones.

In the next aisle, despite feeling a little nervous, I took my time and found three pairs of lovely satin knickers with matching brassiers. I knew my panty size but the brassier size was my best guess based on my chest measurements and with a C-cup to match the breastforms I had ordered. They were black, white, and red which should do me nicely. I picked up some nice slips in my size and decided to head to the checkout before I attracted the attention of the sales assistants.

I thanked god for self-serve checkouts but I was extremely nervous as I scanned my purchases, looking around to see if anyone was paying attention but at this time of day the store was almost empty and no one paid me the slightest notice.

I returned from my car sweating profusely, even though it was autumn. I had checked out the offerings of the women's apparel section online so I knew what I was after and made my way to women's wear grabbing a shopping trolley on the way and throwing in a few t-shirts from the men's clothing section.

The next thirty minutes were heaven and hell. I was so excited, selecting a black leather skirt and a white nylon blouse to go with it, carefully checking the size and praying that my online research would ensure they fit. Then I found a lovely red cotton-lycra blend, long-sleeve dress with a V-neck, tight bodice, and some flounce from the waist down. My prize was the black cocktail dress that was almost identical to the one I had purged, but in a size 12. Then a store dummy modelling a navy-blue pencil skirt and mauve satin blouse caught my eye. On impulse I decided that I wanted the outfit and I found the skirt easily enough but then I spied a blue-haired matron wearing the store's uniform heading my way. I nearly panicked but I found the blouses on a shelf above the skirts, so I grabbed one in a size 12 and I threw it in the trolley and pulled the T-shirts over all my purchases.

I was guiding my trolley through the maze of aisles when Ms Blue Hair caught up with me.

"May I be of service?' she asked, her brows raised as she peered into my trolley.

I blushed, my face turning bright crimson and beads of sweat breaking out on my brows.

"I err, I err, I..." stammered, completely forgetting the ludicrous story I had prepared for this exact contingency.

The matronly lady reached out and put a calming hand on my wrist.

"Not for the wife then I take it?" she winked.

"Well, err, no," I blurted out.

"Come with me please sir," she indicated an aisle with an outstretched palm.

Stupid me began to think of all sorts of ridiculous scenarios. I was going to be taken into custody by the store security for attempted shoplifting, I was going to be humiliatingly thrown out of the store, or I was going to be accused of being a pervert and the police would be called. All absurd synopses of course.

12
  • Index
  • /
  • Home
  • /
  • Stories Hub
  • /
  • Transgender & Crossdressers
  • /
  • Maid to Order Ch. 01

All contents © Copyright 1996-2023. Literotica is a registered trademark.

Desktop versionT.O.S.PrivacyReport a ProblemSupport

Version ⁨1.0.2+795cd7d.adb84bd⁩

We are testing a new version of this page. It was made in 175 milliseconds