Ian found that when he thought of his wife there was no problem getting hard. It was just when it came time to preform. His sissy penis knew it shouldn’t be allowed.
The customer returned on Monday. The older, swarthy man. He obviously disapproved of Ian.
The sissy wore a green one-piece thong. It was lacy and hugged his body. He had matching stockings and the strappy, black high heels.
He curtsied for the man and got him coffee.
An hour later the man stepped back out of Grant’s office, and walked to Ian’s desk.
“Mr. Grant says you are no man. ”
Nervous, humiliated, and not sure how to answer Ian admitted, “Would a man allow himself to be dressed like this?”
“No!” Was the man’s stern reply. “You will service me, then.” It was a command, not a question.
Ian didn’t even protest as he followed the man over to the couch. Passively accepting his place, on his knees between the man’s legs. Ian took out the hairy gentlemen’s cock.
Still limp, he slurped the man noodle into his mouth. Sucking and licking till it grew hard. The taste of pre-cum a strong reminder of what was about to happen.
Ian’s sissy head bobbed up and down on the strange man’s hard dick. The tip tickled the back of his throat. He slid his hand in the man’s boxers. Cupping a pair of sweaty, hairy balls. Massaging them with his dainty fingers.
Soon the man roughly grabbed Ian by the hair and, with a few forceful thrusts, shot Ian’s mouth full of his disgusting jizz.
Ian swallowed it all, and licked the man’s dick clean.
Ian wiped tears of shame from his eyes. “Anything else sir?”
“No! And you are no man.”
“No sir.” The sissy whispered, mostly to himself. Still on his knees as the man swiftly walked out the door.
Ian could smell the man’s ball sweat on his fingers the rest of the day. No matter how often her tried to suck them clean.
Ian spent the week sucking Grant’s dick in the morning and the swarthy man in the afternoon. If he showed up.
Wednesday Ian was wearing a short, taffeta, fairy skirt. Pink lace thong. Black garter with matching stockings. A pink A-cup bra that he couldn’t stop tugging at. And strap on fairy wings.
He practically felt like he was fluttering through the door when he was called into Grant’s office.
Grant was standing in front of his big desk. The sissy’s prick twitched. A frightened shiver passed through him.
“Bend over the desk cream-puff.” Grant ordered.
“Did…did I do something wrong?” Ian hadn’t been spanked all week.
“Don’t talk back, sissy.”
Ian obediently bent over. Elbows on the hard dark wood. His skirt was so short that his bare ass and panty covered crotch were revealed. Vulnerable.
Grant rubbed the sissy’s little cock, then flicked his balls through the lace. Then he grabbed the waistband of the submissive man’s pink panties. Ian’s eyes went wide, as they were yanked down his round ass. Falling to the floor.
“Mmm, not perfect.” Grant said, giving the sissy ass a swat. “Still it’s tight and sweet.” The big man gave the ass another playful spank, as he pulled out his cock.
Grant pulled a tube of lube from his desk. Wiping it on his big dick he said, “Time for your next lesson, you sissy cunt.”
Ian whined when he felt Grant’s fingers separate his ass cheeks. He shivered as a big finger rubbed at his tight anal flower. Lubing it. Circling the virgin hole. His whole world seemed to spin with the motion.
Ian hissed as the finger pressed inside him to the first knuckle. Painful and intrusive. Then it was gone.
Grant leaned into the sissy. Grabbing his hair and yanking his head painfully up. His big, lubed dick rubbed against Ian’s round ass.
“Time to truly make you my little bitch.” Grant hissed into his ear.
Then with no more fanfare he took the last of Ian’s manhood. Spreading apart the wimp’s asscheeks and pressing the tip of his cock to the sissy’s clenched pucker.
Ian squealed as the cruel dick pierced him. Like it was drilling into his soul. His ass spread open in a burst of pain. Sissy tears pit-patted onto the wooden desk.
Grant grunted in pleasure as his big dick painfully jackhammered into the tight pansy ass.
Through clenched teeth Ian begged “N…god no! Please! Uuunh!”
As the man’s big cock hammered him, Ian’s own penis got hard as well. It slapped up and down into his sissy tummy, as Grant fucked him from behind.
Ian was reduced to painful grunting. His body tingling all over. He couldn’t help pressing back into the man violating him. Helping the Alpha painfully ram home. He could feel Grant’s balls slapping against his thighs he was so deep.
With a smile Grant triumphantly fucked the sissy secretary. Now seemingly a willing participant in his own anal violation.
Soon Ian was coming all over the front of his boss’s desk. His sissy cum drizzling down the front.
Grant had his own orgasm soon after. Filling the twink ass up with his masculine cum.
Pulling out he spun Ian around, pushing the twink to his knees. Grant made him clean off his slimy cock. Ian slurped and licked Grant’s dick clean. His face grimaced at the foul taste.
“Now clean up the mess you made.”
Panties still around his ankles, Ian crawled around and licked his own weak cum from the front of the desk.
“You must understand by now you aren’t really a man. You are a beta, a wimp, a sissy. You are basically less than a woman. You were just made to serve real men, Alphas like me.” Grant lectured to him from above.
Ian moaned while he licked up the jizz. Moaned because he knew it was the truth. Had always known. That was the inner wall that crumbled at his first blow job. The wall betas build to try to pretend they are men, when it’s obvious they are not.
Thursday Ian wore a sheer grey gown. It covered him from neck to ankle. With a lace bosom and a slit up one side. Underneath his black thong and matching garter and stockings could be clearly seen.
He had started the day with Grant’s dick in his mouth. Then he was called back to see Amy.
The fat woman was already nude. Thighs spread, one hand already fingering her hairy cootch. A big grin on her face.
“Give mama’s cunt a good lick, bitch.” She ordered.
His shoulders slumped as Ian got to his knees. Pressing his face between her meaty thighs.
Her crotch smelled of vinegar and sweat. It was moist and hairy.
As he licked. The fat woman moaned loudly above him. Grabbing his hair painfully.
“Yes! Yes! That’s it! Lick mama! Lick that cunt!” The ugly woman had a strong orgasm. Rubbing her wet pussy all over his face.
“Ha! Fucking, bitch.” She shoved him away, and turned to the porn on her computer.
His head low, the submissive man walked back to his secretary’s desk.
Ian frowned later, when the delivery man came in.
The young man grinned, and motioned Ian over. He forced the sissy over his desk. He lifted Ian’s gown and pulled his panties down. The handsome man spit on his hand, wiping it on the hard dick he pulled out. The Alpha forcefully rammed it up Ian’s pansy ass.
Ian grunted at the pain and intrusion. Every day his grunts sounded less like a man.
The Alpha reached around and gripped Ian’s hard little dick. Grunting with his effort the man quickly pumped the sissy’s cock as well. “We had beta-fluffer like you back in my fraternity.” The young man explained. “I know how you need to be treated.”