Ian's New Job

He had to drive home like that. Cum drying in his underwear. His ass sore against the seat. His tiny balls throbbing with pain.

That night he couldn't get hard for Wendy again. She asked him what was wrong. He just told her it was the job search.

After she dozed off he couldn't help thinking about the spanking. His little prick getting hard under the covers. His hand stroked his little nub next to his sleeping wife.

Thoughts of his boss's punishment driving him to cream his shorts again. Ashamed, he went into the bathroom to clean up.

On Monday Grant motioned Ian into his office as soon as he got there. "I honestly thought you would be more of a man than to show back up." His boss taunted with a smirk. "Well, if you are going to be the office sissy it's time to start acting like it. Take off your shirt and pants."

Ian wasn't sure what was going to happen when he came in that morning. But this wasn't what he imagined. "But...But, I didn't do anything."

"No. It's not what you did. It's what you are." Grant stepped close. Looming over the smaller man. "You are a beta sissy. And you will be treated as such. Strip!"

Quickly Ian got down to his briefs.

"Just pathetic. Here you can wear these for now." Grant told him. The big man pulled open a drawer in his desk. He handed the sissy a pair of new red, silk boxers. "Put them on. Then bend over."

Ian stripped out of his tidy-whities. Blushing as he revealed his tiny penis again. The little thing throbbing to an erection despite the awful situation.

Ian pulled on the silk boxers. Then he bent over Grant's desk.

Ian gasped through a dozen sharp spanks then was dismissed.

"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.

"You know why you are being punished?" Grant asked calmly.

"I...uh. Because I'm a sissy?" Ian guessed.

"That's part of it." Grant said.

Ian's eyes went wide at the first spank. More a light tap on one asscheek. Grant was only swinging from his wrist.

A few more swats and Ian was moaning quietly at each one. Pink handprints appeared on the sissy's rear then faded before the next swat.

Grant paused. "We both know you don't deserve Wendy. Don't we?"

"Y...yes sir." The admittance sent a dark shiver through the helpless sissy. He didn't want to believe that.

Ian gasped as grant swatted harder. Pale flesh starting to stay pink. His tiny cock throbbed with each spank.

Again grant stopped. "Who does she belong with? You pathetic wimp." The handsome man asked.

"Uh...you?" Ian whined. The Alpha smiled. Then he swung his arm wide. Ian's ass jiggled at the hard slap. The sissy squealed from the pain. He gripped the leg of the old leather chair.

For support? For comfort? He didn't know. All he knew was the pain Grant unleashed on his ass.

Flesh turned from pink to red as Grant dominated the pathetic sissy.

Ian's ass clenched with each burning strike. He couldn't take it anymore. His arm flailed back trying to protect his sore bottom.

Grant just grabbed the man's wrist and pinned it to his back. Against the lace of his corset.

He spanked the weeping sissy's ass to a dark red. Grinning at Ian's ineffectively kicking legs. Clad in their white stockings. like a damsel in distress.

Finally, mercifully, the Alpha relented.

Grant stopped the spanking. He ran his fingertips in circles around the sissy's throbbing derrière. He could feel the heat rising from the punished bum.

"Who else should Wendy belong to? Answer you fucking cock sucker!" Grant demanded. He Grabbed Ian's short hair and painfully yanked his head up.

"Unh! Uh...everyone? Wendy belongs to everyone. She...She should be treated like a whore. Fucked...fucked by any real man who wants her cunt." As the words spilled out of Ian's mouth, cum drizzled out of his pathetic cock.

He wasn't even sure where the words had come from, but they seemed to be what Grant wanted. The big man let him up.

Ian stood before his boss dressed in lingerie. His sissy head lowered. Cum soiled his lace panties. His hand rubbed his warm, red, sore ass.

"Thank me for revealing your truth."

"Th...thank you sir." Ian simpered. Tears in his eyes and running down his sissy cheeks.

"Looks like someone made a mess." Grant chuckled.

Ian looked down. They could both see his stained panties. His tiny prick was soft again. Covered in cum. Resting in its lace crib.

"Clean it up, sissy." There was a menace in Grants voice. One that Ian had no will to defy.

With a lump in his throat and a weight in the pit of his stomach, Ian pulled off the soiled panties. Lifting them to his face. He could clearly see the pale slime.

He grimaced as he brought them to his lips. Slurping up the disgusting, bitter mess. Tasting cum for the first time. His cum.

He could hear Grant chuckle, but not see him. Not through the lace as he cleaned it throughly.

"Good enough, you sop. Get changed and go home. From now on you dress in your new uniforms as soon as you arrive. Understand?" Ian nodded. "And you stay shaved. Or else Amy will help you again."

Ian stumbled out of his bosses office. Nearly twisting an ankle in his strappy high heels.

"Practice more." The laughing Alpha called after him.

The next morning Ian found more lingerie waiting for him when he got to work. This time the theme seemed to be pink.

Pink stockings with little blue bows at the top. A pink silk panty. And a sheer cropped nighty, also pink. There was also a thin headband with a big pink bow on it.

Almost eagerly, Ian stripped. He couldn't take his eyes off the lingerie as he quickly unbuttoned his shirt. He tossed his business clothes into a pile under his desk as they cane off.

Sitting, his first act was to pull on the pink stockings. Covering his smooth legs in femininity. His little prick got hard with excitement. His ass clenched in anticipation of the day to come.

Ian stood admiring his reflection in the window. Too girly to be a real man. Pink stockings with their little blue bows high on his thighs. Little prick standing to attention.

He grabbed the panties and pulled them on next. Not a thong this time. Though the back only covered about half of his round bum. The hips had cute little ruffles, and the silk felt cool and smooth against his hairless crotch.

Next Ian slipped on the high heels. Light blue to match the bows on his stockings. This pair wasn't shiny. The material almost felt like velvet under his fingers. Once again they made his feet and ankles feel weird.

The nighty made him shiver as he pulled it on. There was lace where a woman's breasts would be. Offering just a little more modesty than the rest of the sheer cloth. It was tight and scratchy against his skin. His nipples hardened from the sensation.

Finally he placed the bow on his head. Sensing that, more than any of the rest was announcing to the world that he was a sissy.

Ian sat at his desk doing his paperwork. Though he would get up every half hour and walk around the room. Practicing in the high heels. Getting more confident in them as the day wore on.

Early in the afternoon the front door chimed as it opened. Ian's eyes went wide as the delivery man rolled a stack of boxes in.

"Gonna need you to sign these." The young man said. A handsome twenty something. Blonde with a chiseled jaw. Ian was always a bit intimidated by him. He reminded Ian of the type of jocks that bullied him in school.

He grinned when Ian stood and crossed to him.

"Costume party? Lose a bet?" The young man asked.

"No sir." Ian timidly responds. "My new uniform."

"Huh." The man said thoughtfully. "Tough job market." The sissy couldn't meet the younger man's eyes.

"Yes sir."

"Makes you look like a fucking bitch." Ian could feel his little sissy penis twitch at the Alpha's scrutiny.

The delivery boy reached down and grabbed Ian's little dick through the silk panties. "Looks like you like being a bitch though, don't you?"

Ian wanted to scream 'No! No I hate it. I'm a man damn it!'

What he says was, "Yes sir."

"The bow does a great job of announcing that you are a little cock sucker." Ian shivered at the man's words. "You should tell your boss to get you a little choker though. Complete the look."

The young man grinned at him. "I'm in a hurry today, though." He squeezed the little prick hard enough to make Ian moan. "I'll have to catch you next week."

Then the Alpha was gone. Back out the door.

Grant came in to reception a little later. Taking a moment to admire his handiwork. "What a little fuck wad." He smirked.

He had Ian stand and bend over his secretary's desk. Lightly swatting the sissy's rear as he gave him instructions.

"We will have a customer in later today. I want you to offer the man coffee and to give him a nice curtsy. Understand?"

"Unh! Yes...yes, sir." Ian had a hard time thinking about anything other than the stinging swats on his silk covered ass.

Ian's hart skipped a beat when a swarthy middle eastern man came in. Giving the secretary a confused look.

Ian sent a message to let Grant know his appointment had arrived. Then he got up and carefully walked over to the man. He grabbed the bottom of his nighty and pulled it away from his smooth chest as he bent his knees slightly stepping back with one foot.

He had watched a bunch of videos on curtsying after Grant had instructed him. Practicing till he felt he was doing it right.

He was actually a little proud as he stood before the man.

"May I do anything for you." The sissy dutifully asked.

"Humf. Coffee, I have an appointment."

Ian brought the man his coffee and asked, "Is there anything else?"

The man just shook his head and waited.

Soon Grant was ready, and the man disappeared into the office.

Just before close on Friday, Grant called the sissy into his office. Ian walked over to the desk. More confident now in his blue high heels.

The taller man grinned and moved to sit on his couch. "Come over here, and get down on your knees." Trembling, Ian did as he was told.

Submissive, in feminine lingerie and on his knees he looked up at Grant. Handsome and powerful in a dark blue power suit reclining on a black leather office couch.

"You know what to do sissy." Grant said, smiling down at the kneeling man.

Ian gulped heavily. The moment he had been dreading had arrived. How? How can Grant expect him to do this. He isn't gay, hell, neither is Grant. When he looks up he just gets an impassive look in return.

Ian looked at his boss's crotch. An obvious bulge in those pants. He didn't want any of this. Didn't want to be a sissy.

Yet, he couldn't seem to refuse Grant. The Alpha seemed to know just how to push him. Plus he needed the job. Otherwise he and Wendy could lose everything.

Oh god, Wendy! What would she think.

Ian couldn't bring himself to reach forward. To do this disgusting, degrading act.

About to say something, Ian looked up at his boss. SLAP! Grant open palm slapped the wimp across the face.

Something in Ian crumbled. A barrier to something important. His manhood.

Ian reached forward running his palms up Grants muscular thighs. His fingers finding the man's shiny leather belt. He unbuckled then unzipped his boss's pants spreading the fly open. Feeling lightheaded and floaty. The office air was cool on his lingerie clad body.

Black silk boxers covered the big hard cock underneath. So muck larger than his own pathetic nub. Grant was probably eight inches, maybe even bigger.

In a daze Ian ran his fingers along the shaft, smooth through the silk. He could feel where Grant's dick flared at the tip. He could see the outline in the shiny cloth.

Ian pulled the boxers down. The hard cock springing to the ready. The sissy's fingers lightly slid up and down the shaft. Finally stopping at the tip, his thumb and forefinger massage the helmet-like end. His gaze is drawn to a drop of pre-cum. His thumb spread the glistening liquid in little circles.

Ian leaned forward, his body trembling. For the first time in his life, he tentatively stuck his tongue out. Touching the hot veiny shaft of Grant's big dick. Giving it a little lick.

With a quiet moan he ran his tongue along the length of the penis. The sissy lightly kissed the tip when he reached the top. Ian could taste the bitter pre-cum. Then he kissed his way back down to Grants balls.

Part of him wanted to run away. To end this horror that had gone too far. His eyes blurred with tears as he sucked one hairy ball in his mouth, then the other.