Short Story - Tom's Desperate

Tom sold properties he was good at it but this recession had him scared he just could not get a sale. He worked every hour he could and tried every gimmick.

Once night he was drinking with a friend and spent the whole night moaning to his pal - how hard things were, how impossible a sale was at the current moment in time. Finally his friend blurted out dude your very femm looking why not try the pink pound as a gimmick pretend your gay or better yet dress as a sexy business women and show a bit of thigh!

His friend added you know what they say 'Sex Sells'

That night a drunk Tom returned home to find several bills in his post box. He fell onto his sofa with a glass of scotch and fell a sleep.

He woke on Saturday and went to work trying to make up for any losses during the week. He knew there would be no customers so he wore his jeans and a fitted shirt which he did not bother to tuck in and left his hair loose. He walked into his local news agent and picked up a paper he turned to queue to pay for the paper and while standing in the queue dropped an insert from the paper the man behind him tapped him on the shoulder and said

Miss excuse me you dropped your paper

Tom turned around and the man said oh sorry I thought you were a Miss.

Tom paid for the paper and walked towards his office he passed several women's boutiques and his friends words bounced around his hung over head - Sex Sells the mistake in the newsagent and several girl friends all suggesting he try dressing as a girl.

He stopped outside one of the larger boutiques - Career Girls flashed in pink neon in the window. He swallowed deeply and stepped in.

A largish middle aged women nodded at him and smiled - how can I help you Sir or is it Miss she whispered the last bit of her statement

Tom blushed. The women held his hand and gently patted the back of it and smiled it is ok dear we don't mind and if you tell me what you need I can help.

Do you like frilly, lacy or more sport like undies. What are you dressing for darling. Oh and what is your name.

Tom blushed and whispered back Tom

no darling your femm name

Tom blushed harder still and shrugged I don't have one.

The women smiled and said sweetly not to worry and then proceeded to walk around Tom hummm she mumbled and nodded and smiled at Tom

Suddenly she stopped and said yes I have it.

She walked into the back and pulled out a stunning traditional boned corset in black with purple flower highlights and matching high leg panties.

She then found the most life like breasts forms in DD cup that Tom had seen she shooed Tom into the back of the shop and told him to strip

Tom stood naked infront of the women she smiled my honey she said you do have a femm figure your soo lucky to be so womenly Tom's clit stood out she gently stroked it and said we can deal with this later now please turn around Tom did so he felt her spread his cheeks and smear something cold onto him then on his legs and then his arms

She said honey my name is Miss Matilda but you darling can call me Miss M. I am going to remove your body hair not that you have much to remove.

Tom was then half guided and half pushed into the shower to wash off the cream. He stepped out and Miss M rubbed cream into his body he enjoyed the feeling and found his sissy clit getting hard.

Next he was told to bend over a chair he felt her fingers probing him and then something push into him.

Miss M errr what are you... he tried to stand up but Miss M pushed him back down and shussed him quiet.

Tom felt totally exposed and humiliated he felt that he could not sink any lower but then all of a sudden he felt his shame deepen as the tube hit his prostate and sent shivers into his tummy he little sissy clit dribbled cum onto the chair and Miss M tutted as she poured hot water into his bowels.

She put on rubber gloves and started to wank his sissy clit violently Tom moaned half in pleasure half in pain and then came into Miss M's palm she feed him the cum and then stopped the water and plugged him a butt plug. She then injected him with a special liquid and told him to wait there.

He felt his extended tummy groan and moan and he called for Miss M

Nothing...

He called again

Nothing...

He started to panic but did not want to move either (the liquid he had been injected with was a submissive hormone and also contained a high dosage of female hormones)

He did not understand why he had to obey he just knew that he had no choice.

He almost screamed this time MISS M PLEASE....

Several seconds past and she appeared smiling yes dear what is it?

My he blushed.... My

Yes dear please refer to it as your ass pussy

Tom blushed and he started to cry my ass pussy I need to go to the loo

Oh I see Miss M smiled well of you go.

Tom stood up and held his tummy he was sobbing freely now.

What is it hun oh I know as Miss M walked next to a stumbling in pain Tom it is because you want to be a girl and you do not have a name.

Tom nodded.. he would agree to anything just to sit on the loo

She smiled well what name is it to be?

Tom blushed and between sobs said anything you want Miss

Miss M smiled and pushed Tom onto the loo

he let himself go and closed his eyes and covered his face and cried as his bowels emptied into the loo.

Miss M stroked his hair while whispering good girl well done

Now show me how a girl wipes herself

Tom did so and then as directed stood up and waited for his instructions

Miss M lead him to the dressing room and started to chat about pleasing a man, sucking cock, Tom was lost he was dizzy and totally broken.

Miss M started to spray glue onto his chest and then fixed on the amazing breasts she then blended the edges in with colour and makeup.

Tom felt the weight on his chest and was instantly turned on he loved the way they moved and loved the fact that the forms had a wire and clip attached to his real nipples so that when the nipples on the forms were pressed or touched they would harden and then send a small electrical charge to his nipples below sending waves of pleasure through him.

Miss M said there now take a look

Tom was amazed a buxom blonde naked babe with a small but hard cock stared back at him his hair was perfect the breasts forms just right and his makeup a little slutty but somehow fit his persona.

Now Tom I think we shall call you Tammy.

Tom shivered he loved the name - why was he going along with things why did he need to he was lost and could not find a way back.

She dressed Tom or Tammy in the black and purple corset and stockings. Then she put on the tight black business women's dress followed by the matching jacket.

Next she added sexy necklace, then she made Tom step into 6 inch stripper heels.

Tom stood still looking at his reflection his breasts looked amazing and Miss M clapped in delight as she told Tammy to walk towards the door and then back again.

She corrected Tom's walk and then handed him a hand bag and shooed him out the door.

Tom walked out of the boutique confidently he felt amazing. The hormones secretly doing their job and making him feel womanly and totally at ease.

The breeze blew around his thighs and blew up his dress bottom he quickly placed his hands on his skirt and smoothed them out. He loved the feeling of openness his skirt provided and loved the feeling of the boned corset holding him in and upright. He enjoyed the sensations the silky material the straps pulling tightly against his thigh holding up his stockings, he even enjoyed the feeling of his panties riding up his ass.

He giggled as he looked down and watch his breasts jiggle.

He stopped at the crossing and could not resist running his hands down his sides and following the curve of his body.

He started to cross the road and he jumped as a car beeped he turned to see a man winking and mouthing something naughty at him.

Tom now Tammy blushed and smiled as she picked up the pace and crossed the road. She loved the feeling of the heels and adored the noise of her heels on the pavement.

she smiled to herself as she could see guys staring at her.

Finally she arrived at the house she searched for the keys in her handbag and opened the door and then placed the for sale sign on the lawn.

She stood by the sign and waited.

Within 10 minutes two guys pulled up and said hello and asked about the house. Tammy's mind whirled she was doing it she was making a sale. The guys seemed interested as they followed her around the house.

She could feel their eyes staring at her ass and she loved it.

With out warning she was pushed to the floor and knocked out. She woke feeling a warm splash on her face she was lying on her side and felt something on her mouth and something holding her hands together. Her ankles were also strapped together.

He vision started to clear and she realized that one of her assailants was pissing on her to wake her up. She was dragged to a kneeling position and then the man with his cock out stopped pissing on her and wiped his cock dry on her face and hair.

She closed her eyes and sobbed. She felt rough hands pull her eyes open and the other man place his cock on her noise she almost gagged the smell was awful the fingers pulled at her eyelids and made her stare directly at the cock.

Still with the ball gag in place they pulled at her clothes stripping her down and as the corset was pulled away the support for her huge breasts forms stopped and they fell the men laughed and began to pull at them the adhesive was so tight it in turn pulled at his skin.

Tom felt ashamed as his mind raced with mixed feelings and his sissy clit jumped with delight. He felt the man pull at his breasts and laugh as he pretended to milk him.

The tied him up and left him on the floor his cockette erect they laughed at him and began to wank over his face.

They came in his face several times his make up running and cum dripping into his eye he had to close one as the cum stung horridly.

They bent him over the table and fucked him several times Tom moaned as best he could and came several times himself he was now totally female nothing in him was left Tammy was truly born.

The men left Tammy tied up and with a for sale sign and a plate full of cookies. Laughing as they left.

Tammy sat on the firepalce next to the cookies cum oozing from her holes dripping into her eyes her make up a mess and her matted cum covered hair.

Time passed slowly and then Tammy heard heels on the wooden floor she lifted her head up to see who had come into the house.

She try to cry out as she saw it was Miss M her muffled cries for help caused Tammy to blush.

Miss M hussed her and said you are sooo perfect darling I do this with all my faggot clients it is such a good earner....

Tammy's eyes widened with shock and she sobbed Miss M walked out of the house

Tammy's swa several men walking in through her tear stained eyes she lowered her head in shame and cried.