“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.