Timmy's New Job Ch. 02

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Desperate, Timmy takes job as painslut & boytoy.
1.2k words
3.93
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Part 2 of the 4 part series

Updated 11/01/2022
Created 09/24/2011
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Timmy was squeaky clean and drenched, much to his disgust, with a girly perfume. Timmy was taken to another room full of bright lights, make up, and extremely erotic lingerie. Mary unhand cuffed Timmy, then the other four girls forcibly strapped Timmy to a swivel type make up chair in front of a large mirror surrounded by lights.

Puzzled, Timmy asked, "What are you going to do?"

"We will transform you into a hot looking little sissy boy." Mary said as she laughed at the look on his face. "Are you going to submit?"

"No. I'm no sissy." he protested.

"Do you know what that ball harness locked around your balls does?"

Timmy nervously shook his head no.

"You don't? Let me demonstrate." she said as she produced a remote and clicked a button.

Instantly, Timmy's back arched in writhing pain that radiated from his balls and into his groin. A second later the pain was gone, and Timmy slumped in the chair as he whimpered for mercy.

"Are you willing to become a sissy slave boy for Mistress Evilynn?"

Timmy did not answer fast enough, so Mary gave him another dose of pain. Only this time, she left it on. As Timmy jerked and bucked in convulsive pain he heard loud moaning sounds from the girls in the room. Through the reflection in the mirror he watched as they masturbated, then took turns sucking each others pussies.

Timmy felt the flow of electric current tingle like needles all over his balls and up his throbbing hard shaft. The head of his cock had swollen to an enormous size which proved too tempting for Mary. She vaulted onto the chair that the helpless Timmy was strapped to and shoved her ass into his face.

Mary forced Timmy to suck her pussy, while she sucked on his balls and then ran her mouth up and down his stiff, pulsing shaft. Next, she wrapped her naughty red lips around his all day sucker and licked off the pre-cum. Timmy moaned in pleasure as Mary deep throated his astonishing long cock!

Timmy worked his tongue furiously, as he sucked and licked the juice that squirted from her clit. Then he pressed his lips tight against her ass hole and sucked as he rammed his very long tongue through her anus and was surprised to find the soft yummy brown poop. He allowed his tongue to sink deeper into the brown goo, as he lingered over the taste.

Mary moaned and squealed with the surprise anal tongue fucking she was getting as she commanded, "Yes! Harder, whore! Deeper! DEEPER!"

Inspired by his depravity, she dove down on his cock and worked her head up and down faster and faster as the pressure grew inside her mouth. Realizing Timmy was about to cum Mary pulled her mouth off the boy's swollen cock and started to spank his balls hard, as he screamed like a little girl. She had acted just in time. She knew she would be a big trouble with Mistress Evilynn if she had taken Timmy's virginity! She clicked the remote off and watched, with relief, as Timmy's cock began to shrink.

"Why did you stop?" he asked as he cried in frustration.

"We can't play with you until Mistress Evilynn does. You belong to her. You will be her little boy, or girl as the case may be. Call her mommy, and she will call you mommy's little boy or girl. It depends on what she's in the mood for. Are you going to obey?"

"I'll do anything you tell me to Mary." Timmy said as he stared into Mary's eyes.

"OH NO! He's in love." Mary said as the others laughed.

"It serves you right for sucking on one of Mistress Evilynn's toys." laughed Becky as she expertly began to apply make up. Soon, the already long haired Timmy, more closely resembled a little girl then a boy, with make up that would appeal to the taste of the most discriminating pervert.

Timmy stared at his new persona in the mirror, with bewilderment. The face that stared back looked more believable as a little girl than a boy.

Mary stroked Timmy's huge cock as she proposition him, "If you agree to do as told and please Mistress Evilynn, then you will sleep in my bed when Mistress allows it. What do you say baby? When you aren't sleeping with mommy, you get to sleep with your big sister. Sound good to you? But, only if you learn to do all the naughty things that please me. OK, whore. Do we have a deal?"

Timmy nodded with lust, until Becky said, "You might change your mind and wont to sleep with mommy exclusively when you see her alarming figure. One of her breast is twice the size of your head. OH NO, now he looks confused!" Becky deviously laughed. "Besides, why are you the only one who gets to fuck with baby brother, Mary?"

"Do you expect me to share!" Mary shouted.

Miss Tover popped her head into the room and asked, "Any problems here girls?"

"No Miss Tover." the girls replied in unison.

"Then get him ready! Or do you all need to be hung by the arms and bull whipped?"

"No Miss Tover." the girls replied again in unison.

"And don't forget that I get first dibs on new meat when Mistress is not using it. Understand girls?"

"Yes Miss Tover." the girls all replied.

When Miss Tover was gone Mary reassured Timmy, "Don't worry about her. She just likes to make a noise. She plays only with Mistress, and never with her boys. If makeup is done, he needs to be dressed." Mary said to Becky, as she asserted her authority. "I'm your supervisor! Remember! If I want Timmy to be my toy, then he will be!" Mary said as she slammed Becky against the wall. "Got it? Now get him dressed!"

Soon, Timmy was wearing small, frilly, red, silk panties. The panties were crotchless, allowing the excited long cock and balls the dangle free. On his shapely legs the boy wore shear, black stockings that were attached to a black, silk garter belt. To top it off he wore a pair of six inch spiked heels that he found hard to walk in.

Then Mary put what looked like a diamond studded dog collar round his neck. It felt snug though not too tight. Then she put matching cuffs around each wrist. Dangling from each cuff was stainless steel clips. Each clip snapped onto steel rings hanging from both sides of the dog collar. Locks were added making it impossible to release the clips from the collar without a key making Timmy unable to use his hands.

They laid Timmy face down, and fastened matching cuffs around his ankles. While bending his legs back from the knees, short chains were clipped to the ankle cuffs, and the other end of the chains to a ring on the back of the dog collar leaving Timmy erotically hogtied on the floor. They pulled his arms behind his back, like bent chicken wings, and a strong steel pole was fitting through the openings behind his elbows. A girl took hold of each end of the pole and lifted Timmy up off the floor and placed each end of the pole on their shoulders like a yoke.

Now Timmy, still hogtied, dangled by his elbows from the steel pole as Mary said, "We're done. Let's take him to see Mistress Evilynn."

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