“M…my clothes?”
“You’re wearing them. You can get your things at the end of the day.” Grant told him.
Dejected, the sissy walked out to his receptionist desk. Hoping that there wouldn’t be any visitors today. He kept having to pull up the silk boxers as they were too big for him.
Around ten in the morning Amy came into reception. That was a rare occurrence. She spent most of her days sitting around her desk in the computer room watching porn.
“Boss says your the office sissy now. Git your skinny ass over that desk, boy.” She ordered him.
Ian’s eyes went wide at the thought, but he does as told. The fat woman laughed as her meaty hands beat a staccato rhythm on his round ass.
When she was finished, his rear was red and sore. “He also said you got a teeny pecker. I wanna see it.” She grabbed at his borrowed shorts as he stood.
She tugged the silk boxers down and laughed “Boy ain’t nuthin’ there.”
It was basically true. Soft he was less than in inch. Just a little bump. His balls were his only proof of manhood. Though they were tiny too. Like shriveled raisins.
“Ooop! Little turtle is gettin’ brave!” She laughed. His cock seemed to be getting hard at her derision.
Ian gasped when the grotesque woman grabbed his tip. He whined as she squeezed painfully and pulled it as far as it would go.
“Yup. That’s tiny.” She slapped his sissy bump back and forth a couple times before blowing him a kiss and heading back to her work area.
The next two days continued like that. Ian would receive two or three humiliating spanks a day. Sometimes from fat Amy.
Always wearing those silk boxers.
At night he still couldn’t get hard for his wife.
Then it was Thursday morning.
“Hey sissy! Get in here.” Grant ordered when Ian arrived. His boss and his fat co-worker were waiting.
“Amy will take you to get waxed. Body hair is something a man has. Not you. When you get back your new work clothes will be waiting.”
Humiliated, Ian followed Amy out of the office. His head hanging low.
Ugly Amy grinned at him as they got in his car. “Lets go.” She ordered.
The Fat woman directed him to some hole in the wall massage parlor. Apparently run by her sister.
In a small private room Amy had him strip down. Ian hesitated, uncomfortable with the whole thing. Then Amy casually reached out and slapped the sissy’s ass. Reminding him of his place. “Get to it.”
Ian quickly got nude and on the table. Amy herself did the hair removal. Backside first, then the front. Everything below eyebrow level.
Ian cried out with each strip of hot wax. It felt like his skin was coming off.
Amy had him flip over and took great cruel enjoyment out of stripping around his hard little peanut. Especially the pain from stripping his balls.
After an hour, Ian’s body was bare. Grinning at the smooth pansy, Amy asked, “You ever cheat on your wife?”
“No, of course not.” Ian responded, trying and failing to sound firm.
The ugly woman quickly stripped off her clothes. a big, pear shaped blob of naked woman. She hopped on the table. Hairy, moist, twat straddling the sissy’s crotch.
“Please I can’t.”
“We both know that’s not true. Your sissy dick is just asking for mama’s sweet cunt.”
It was true, the pain and humiliation had given his penis a raging three inch boner.
The ugly woman easily slid it in. Ian closed his eyes feeling the fat woman move her cootch up and down his tiny cock.
Soon, without wanting to, Ian shot a load into the messy cunt. Amy grinned at the sissy as she too orgasmed. “Aaah! That was great.”
When they got back to work Ian found lingerie laid out on his chair with a note. ‘Put it on Sissy’
He frowned down at the white lace corset, matching thong panties, and white thigh high stockings. A stark contrast to the dark upholstered chair.
Black high heels lay on the floor beneath.
Resigned to his fate, Ian stripped. Taking off his men’s slacks and dress shirt, in preparation for wearing the woman’s lingerie. His tiny penis grew hard at the very thought.
He started with the panties. Stepping into the sensual underwear designed for women. He slid the thong up his newly smooth legs. The tiny back settled between his feminine ass cheeks. Immediately feeling awkward. Like a punishment for being a sex object. In the front, his penis fit snugly under the white lace. Even hard it stopped just short of peeking out.
Ian stood for a moment wearing just the panties. His skin tingled and a shiver rolled through him. He knew he should just walk out. Leave. There was no way he could accept this.
Next the lace corset went on. He struggled to get all the hooks to catch. Minutes passed as he worked it. Standing in reception. Only the lacy thong to cover his shame.
When he finally had the corset properly on it felt strange against his skin. Sort of scratchy and tight. Like he was bound in a cage.
The cups at the top stood empty. They were only for B-size breasts, but he didn’t have anything to fill them with.
Then he sat. Reaching down he slid the first silky, white, stocking up his sissy leg. His body shivered as it slowly engulfed him. His tiny prick throbbed under its lace cage.
He thought putting the stocking on would be like putting on socks. But this was much more intense. Something about the stocking made Ian feel especially feminine. He felt lightheaded as he pulled the second one on. They stopped just short of his ass. The way they hugged his thighs made him want to fuck. Or…or be fucked.
He sat for a moment, rocking back and forth on his nearly bare ass. Strangely savoring the feel of the lingerie on his body. Little shivers of excitement seemed to roll through him, settling in his tiny prick.
Carefully he attached the suspenders dangling from his corset to the tops of his stockings. He could see his reflection in the window. For a moment confusing himself with a strange woman.
Then he sat. He easily slid his dainty, stocking covered feet into the high heels. They had a strap that snapped around his calf and he didn’t like the way they felt on his feet. Like his ankles were always pointed down.
Ian spent the day typing up reports. His strange excitement never abating as he waited for his boss to call in him.
Just before the end of the day, Grant gave him a buzz. Feeling awkward in the high heels, Ian stumbled to the man’s door. Then into his office.
“You…you wanted to see me sir?”
“Come in, pussy. Turn around so I can get a good look.” Grant ordered.
Ian stumbled to the center of the room. He took a moment to steady himself. Then he raised his hairless arms and slowly spun around for his smirking boss.
“Good. Very good. You need more practice in heels though.” Grant told him. “Now come here.” His confidence palpable, Grant crossed the room to one of the high backed leather chairs in the corner. Patting his thigh. He watched Ian slowly, carefully approach.
The bigger man made the sissy lay across his lap. Ian’s face pointed down, his round ass in the air. Nearly bare and vulnerable.
The sissy could smell the old leather of the chair. It’s scent was strong. Masculine. Dominant. One of Grant’s hands rested on the small of his back. Almost comforting. As if Ian belonged to the Alpha male.