Forced Waitress

David sunk to his bed and cried. He couldn't do this, he thought. He had to do this he realised. As he hung his head he viewed with disgust the layers of petticoats under the bubble gum pink, short, waitress uniform dress he had been forced to wear.  They fanned out beneath him, revealing delicate embroidered lace that lined the layers of white satin fabric. David pulled at the petticoats, lifting them reveal frilly lace topped, white stockings, stockings that hid any sign of David's moderately hairy legs. David was desperate, an English boy alone in America, on his travels, down on his luck, with no money and nowhere to stay. The motel he was now imprisoned in had offered accomodation with a waiting job. He had read the ad, applied and the manageress, a stern but attractive woman in her 40's, seemed eager for him to start. He had now re-read the ad again and again. It was his mistake, it clearly said 'waitress' he had read it wrong. He had now been fed, had stayed the night and now owed the manageress rent. He tried to explain his mistake but she  was not having it,' he owed her' she said.  She did not care that he was a boy, almost a man. He was pretty enough to pass as a girl, he HAD to pass as a girl or she would call the police and he would be spending the rest of his holiday in prison.

It was then the locked door to his room opened. The manageress walked in, took one look at her new 'waitress' and exploded. "This will simply not do" she snapped. David jumped, he knew he would never pass as a girl. His long blonde locks were simply not enough to satisfy the most short sighted of people he was a girl. But it was not that. "where is the underware I gave you?" she snapped, viewing with obvious anger, the pink embroidered and silk bow basque set still laying unused on the bed bedside David.

"I can't do that..' David started. He did not finish as he was slapped, slapped hard round the face, pulled from the bed and his dress quickly unbuttoned at the front. David tried to struggle, but was soon disrobed, the dress falling around him to the floor as the manageress yanked it from his shoulders. He now stood, half naked, except the stockings and his boxers, that hung low over his bottom, pulled down by the dress being so forcibly removed. Before David could react further the manageress pushed him back towards the bed and the discarded basque was wrapped around his middle and his arms pulled outwards and then through the delicate lace sleeve lined, shoulder straps. David was smaller in height than the manageress and his slight body no match for her, now frenzied, actions. His hands tried to push hers away as she took to the task of fastening each tiny clasp that held the basque together at the front, they were simply slapped away. David cried out 'no' but his cries just fell on deaf ears as he was the spun round violently, the force of which made him buckle and he fell forwards onto the bed. He was now bent over, his head forced into the bed sheets and he had no choice but to stop struggling and accept his fate. He could feel his body suddenly jerk, then jerk again, the manageress now pulling the thick pink ribbon that laced the back of the basque tight and then tighter still, before the manageress tied it briskly but neatly into a bow at the bottom.  It was then David's boxers were finally, shockingly removed. He cried out again, but his voice was stifled by the bed and his disobedience punished with a swift, hard spank to his bare bottom. David had not been spanked since childhood and the shock of it coursed through him, paralysing his whole body into temporary submission. This was enough for his limp frame to be stood up to attention, the elasticated suspender straps fastened to the lace of both his stockings and a tiny lace thong guided up his legs, over his thighs and onto his bottom. David tried to protect his dignity, meekly covering his penis with his hands, but once again his hands were batted away 'that flaccid little thing is not a real mans pride, you should be ashamed!' the manageress called out. David was, ashamed, humiliated and degraded. With complete submission he let her take his wrinkled willy, tuck it between his legs and pull the panties firmly into place onto his hips. 'Done' the manageress said, then guided the pink waitress uniform dress back up David's legs, slipping his arms through the puffed short sleeves and once again buttoning him back up at the front. David now let out a wail, a long cry of a young man reduced to a simpering sissy. But the assault on his masculine identity did not stop there. There was 'finishing touches' to be done the manageress said and then she was gone. 

David now stood alone again, locked into his room, standing crying, dressed as a waitress, feeling like a sissy and ashamed at how easy he had been submissively sissified. The manageress then returned, with pink stiletto shoes and a make up bag in one hand and a pair of what looked like chicken fillets in the other. The fight had gone from David long ago, he was now an obedient slave to his master, the manageress. 'Sit' she said and he did, facing his tormentor, snivelling, whipping the tears from his red eyes. The manageress now became calmer, almost motherly, commenting 'good girl' as she positioned herself before David. Then her hand reached down his front, into the lace lined bra of his basque and put one of the rubbery breast forms into the cup, before pulling out and grabbing a hand full of flesh on the way. She did this again the other side, then smirked. As David looked down he could now see two small fleshy mounds resting over the top of his bra and pushing outwards over his dress. He had breasts! While David almost marvelled, confused at this sudden transformation the pair of tight fitting pink stilettos were placed onto and forced over his white stockinged feet. The manageress then placed a firm, guiding hand onto his chin, pulled his head up and started applying a layer of foundation. Something strange happened now, for David's hatred for his tormentor turned into the slightest of bonds and he willingly let her apply the rest of the foundation, black eye liner and eye lash mascara and a layer of girly pink lipstick. David's new compliance to his fate was quickly rewarded by the manageress with another 'good girl' followed by the delicate massaging of his hair into a loose pony tail, trimmed with a pink ribbon. 'Very good girl' the manageress commented, now happy and content her work was finished.

"You will now work for 12 hours in the diner, you will serve all day and be the quite, compliant and happy girl you are now. You will not moan or cry and never tell anyone who or what you are. You are a maid, a pretty in pink, girly waitress who obeys her manager and does exactly what she says. Then and only then can you go. Understood?"

"Yes mam" David replied, sheepishly nodding his head. It was to be the end if his nightmare, if he got through the day, he thought. However little did he know it was only the start!
Surreycrossdresser Surreycrossdresser
36-40, M
10 Responses Sep 14, 2012

A very descriptive "tail". Thanks for sharing David's experience.. ....Mmmm!!!

Oooooh. I simply adore this. Imaginative and well written. You should be very proud.
I will be checking out part two, and other stories.
Thanks. X

A very exciting story. Thanks to Surreycrossdresser for writing and posting it. I'd also love to hear of the forced waitress' further adventures. Maybe the manageress gets him to continue in the role through a system of rewards in addition to the spankings and other punishments. Like he gets to *** in his satiny panties from her ministrations if he acts girly enough.


Thank you so much I do like that idea!

Beautiful story. He was a good girl

Very sexy story. My panties are damp!

Again left hanging good story

Awesome story x

nice story, thank you,

Thank you!

Baby, what a great story. Love every word. Thanks


Yes, I wish, I am hard from reading it. My pink lace panties do not cover me.


Yes, I am, can we be friends?

Hi ya, I would love to be friends. I have added you. Thank you so much for asking.

Very good story I loved it. I wouldn't have minded if our hero got a little more spanking to make him accept his fate.

And I wonder how he will react when guys start making passes at him and trying to feel him up.

Thank you so much, you have given me such naughty thoughts as well!