Ian's New Job Ch. 02

Ian took a deep breath. "I...I'm a sissy cuck. My...master demanded that I offer you my wife for the night. To do whatever you want to her." Ian found himself looking at his feet as he explained. Glossy, white high heels over his white stockings. He couldn't bring himself to look his wife or his father in the eyes.

Patrick grinned and stepped close to Wendy. She grimaced and looked away in shame, as the old man brazenly flipped her shirt up. Her large breasts fully bared to him. "Nice tits." He told her as he gave them a firm squeeze. "Yeah, ok. I'll fuck your whore wife, you little shit."

Patric pulled the brunette into a close embrace. "There's an old kennel out back. Grab a blanket and go sleep out there. While I rock this bitch's world."

Patric followed Ian to the backdoor. Tossing him a ratty blanket as they passed the little laundry room. Then the sissy was out in the back yard.

"Let's get something straight..." Ian could hear the old bastard slap his wife as the door closed.

With tears in his eyes, the sissy stepped into the fenced in kennel. He wrapped the blanket around himself and cuddled in the large dog house as a second story window opened. Shedding some light on the back yard.

Soon he could hear his wife gasping with sexual pleasure. His father's own fuck moans sending shivers down his spine. The occasional sharp snap of a hand striking skin would carry across the yard. Spanks or slaps, Ian had no way of knowing.

It was a long night. His father seemed to have the stamina of a twenty year old.

In the morning, Ian gently sucked on his father's balls. The old man's limp cock rested against the sissy's face. Slick with fresh jizz and Wendy's cunt juice.

Wendy had made breakfast. Now she sat next to the old man on the couch. He happily groped her between bites of bacon and toast. The sissy on his knees before his father. Serving him in a way no son should.

"Yeah, we are going to have to get together like this more often, pussy." The old man chuckled above his son.

Grant smirked down at his pet. "Sounds like you both had a great time with your old man." He taunted.

Wendy was laying across her master's lap. Nude except for a black garter and stockings. And her high heels. Her ass was red and throbbing from a spanking. She moaned quietly as Grant fucked her with two fingers.

Ian knelt in the middle of the room. Still in his lacy bra, though his panties lay discarded nearby. He also had a garter and stockings. Matching his wife's. His tiny prick still stung from the hot wax Grant had dripped all over it.

"Saturday night I have a really fun plan for the two of you. Make sure you take extra care getting ready before you come over.

Wendy gasped as her master's thumb flicked her sensitive clit. Her body shivered as she was taken by a small orgasm.

"I wonder what he has planned for us." Grant said as he stepped into the master bedroom Friday night. They were both naked and excited to sleep together. One of only three nights they were allowed per week.

"Something vile no doubt." Wendy said as she looked thoughtfully at her sissy husband.

With his slight body plucked and his make up on he really did look like a girl. Even naked, his tiny sissy bump was easy to overlook.

She ordered him to put on a purple lace panty and nighty. Cropped to show off his smooth tummy.

On the bed he lay between her thighs. Licking her to orgasm as she squeezed her big tits and thought about her master's cock.

Then she let him lay down and pulled his panties down fat enough so she could suck his little dicklette in her mouth.

She couldn't help a strange feeling of shame as she sucked the sissy off. Like she was doing something no one would approve of.

Afterward they held each other lovingly. Drifting asleep together.

They were both dressed in cute grey cocktail dresses. Short and a bit indecent, though neutral for most of the activities their master had called upon them to do.

"I have a friend who runs a bordello." Grant smiled at his pets. "You are going to prostitute your wife."

Ian's eyes went wide with shock, but Wendy just nodded her head. She had little shame or modesty left after the last few weeks.

Grant drove them to a large house in a lower class block near the airport. When they went in they were greeted by half a dozen washed out women in lingerie. And a handful of men in cheap business suits.

Grant worked things out with the madam.

"Great. Ian strip to your underwear." The sissy had a baby blue, silk bra and panty. Along with white stockings. Grant made him kneel near the entrance and tied the sissy's wrists behind his back.

He wrote 'PLEASE, FUCK MY WHORE WIFE. $50' on Ian's tummy in hot pink lipstick.

Wendy changed into a white, short lace skirt and matching camisole. She was by a large margin the most attractive woman there.

Then they waited. With her standing next to her husband looking sultry.

Soon the first John paid for Ian's wife. An older man, he paid the madam with a credit card who gave him a dollar and instructions in return.

The old man grinned as he walked back and shoved the dollar in Ian's panties and led Wendy away.

Before long the old man and Wendy returned. The John gave Ian a firm slap across his face and left with a smile.

The evening turned into a long night of dollar bills, fucks and slaps. Fourteen men in all. Wendy was sore and exhausted by the end.

Ian spent most of the night with tears in his eyes. His heart breaking a little more each time a stranger led his wife away.

Something about being so complicit in selling her body. Something about accepting the dollars as a pittance for breaking their intimacy killed a little of his soul.

When they got home early in the morning they both slept in their own bedrooms.

Sunday started with a call from grant. The smug man asked how they enjoyed their first foray into being whores. Then moved on without waiting for an answer.

He was excited about the orders he had to give the pathetic couple. The next part of his master plan.

Ian put on a cute pink bra and panty set. With little blue bows on his hips and in between the cups. He also had a white garter and stockings and a little blue bow in his hair.

Wendy wore a red lace one piece with a thong back. The lace was sheer enough that her breasts were clearly visible. As was the fact that her pussy was bald.

She has stockings that matched Ian, but without the garter.

They took a deep breath. Then walked out into the sunny day of their back yard.

Wendy got the mower out and Ian grabbed the gardening basket.

When they started on the front yard they drew onlookers. Cars slowed down as they passed. Neighbors peeked out of windows.

Wendy, sweaty and nearly nude as she pushed the mower. Ian looking like a pansy in women's underwear as he knelt and weeded the flower beds.

"I'm not sure we are up for a party." Wendy weakly protested.

"That wasn't a request." Grant growled over the phone. "Be at Hank's by seven." Then he hung up.

"A party with the boys." Wendy told Ian.

"I...what should I wear? Do they know? Oh god, what if Grant told them the things he made us do?"

Wendy patted his shoulder. "I'll help you pick out a nice dress. If Grant hasn't told them, then we will say you've taken up crossdressing."

Wendy led him to his room. Now fully decked out like a teen girl's bedroom, as Grant had purchased humiliating items for him. In addition to the princess vanity, the bed was a pink frilly canopy nightmare. Complete with half a dozen fluffy pillows and stuffed animals. The wallpaper was white with pink hearts. There was a pink armchair in one corner and a big wooden rocking horse in another. Big enough that Ian could use it with just a bit of discomfort. One wall even had two posters on it. One was of three stripped down sexy firemen. The other a sexy vampire man with a big bulge in his pants.

Ian had been ordered to masturbate three times a week while staring at the posters.

Wendy opened his dresser and pulled out a canary yellow, lace bra and panty set. Then a short, blue dress with a pleated skirt and a button up top. His bra was visible through the white cloth. A pair of white high heels and a blue hair bow completed his ensemble.

"No stockings?" He asked a little disappointed. He actually liked when they wore matching stockings. Without their rings it had become a strange form of intimacy to them both.

"Not tonight, sissy," Wendy told him as she caressed his cheek.

Then she headed to her own room while he got dressed.

Wendy's bedroom was a bit more stark. Plain bed, dresser and small vanity.

She was getting more excited by the minute though. Surely Grant hadn't told the others what he had done to her. The evening would help her feel like her old self. Hanging out among old friends.

She pulled out a pink silk thong and matching half cup bra. Wondering if they would play any of those stripping games. Usually she was only willing when she was drunk. Tonight though...

The thought of real men seeing her in her sexy underwear turned her on. The bra couldn't even successfully cover her nipples. Her little berries would be on display for all to see.

She pulled on a thin tank-top. Grey so her areola didn't show through, though her nipples were clearly outlined in the cloth.

Then a pair of tight workout shorts to match. Small enough that the bottom edge of her asscheeks were visible.

Then they were in the car and on their way.

They walked around the side of Hanks house. They could hear people on the patio. Wendy smiled as she turned the corner and saw her friends.

Ian picked up on the strange mood right away. There was anticipation in the air. An awkwardness not caused by his women's clothing.

Then he noticed the only other wife was Tilda. The chubby blonde.

"Lookin good, Ian!" Bart said in what seemed like a jovial voice, though the sissy thought he caught a predatory edge to the man's voice.

That's what he felt, Ian realized as Ben handed Wendy a drink. The boys had always seemed like predators to him, but now it felt like it was out in the open.

"Ah! The whore of honor has arrived. And her pathetic sissy cuck." Grant announced as he stepped out of the house behind them.

Ian saw a shudder run through Wendy. The shock on her face. The thin veneer of normalcy she had built for herself shattering.

The spell had been broken. The boys hungrily grinned at the submissive couple.

Grant stepped close and put an arm around Wendy's waist. He could feel the beautiful woman trembling as he hugged her. "The boys have been waiting to see more of you fore some time." He brazenly reaches for her big tits with his free hand. Squeezing them in front of the crowd. Savoring the broken look of despair on her beautiful face. "I've told them all about your new position in my company."

"Yeah, on your knees, slut!" Tilda called out. Wendy shuddered at the venom in the chubby woman's voice.

"Let's get this party started." Grant grinned, licking the side of Wendy's neck. He moved her up on the patio, so everyone could get a good view. "Now show the boys what you've selfishly been keeping from them." He ordered, stepping away.

Ian gasped when Tilda grabbed him and pulled him to the side. Away from the boys and his wife. She lay down on a lounger and pulled him down next to her bulk. "They're going to wreck your whore wife, sissy." She whispered in his ear.

On the patio, Wendy gripped the bottom of her tank-top. She didn't have enough ego left to resist. Her self respect had been burned away by Grant. If the men she considered her oldest, and best friends wanted to abuse her...she wouldn't resist.

The gathered boys cheered as she pulled the grey shirt over her head. Her hard nipples visible just above the half-cup bra.

She turned and bent way over to pull her shorts down. Obediently making sure the show was exciting for the men. The thin cloth slipped over her amazing ass. Now mostly revealed. Only her thong protected her modesty.

Standing back up she reached back with one hand. Covering her big breasts with the other. Hiding her tits as the pink bra fell to the ground.

The boys cheered again when she revealed her breasts with a little flourish. Looking to Grant for approval.

Tilda groped Ian's chest through his dress, as they watched. Rubbing him through his lace bra.

Wendy nibbled her lower lip. Then quickly pulled her panties off. She stood before the men in all her nude glory. Waiting for her next indignity.

"I think the boys deserve an apology for the way you've treated them. Keeping your goodies for yourself. Or worse, for that sissy."

He stepped up and pushed her to her hands and knees. "Crawl..." He sneered, savoring the word. "Crawl to each man and say your sorry. Then kiss his penis to show your submission."

Shivering, Wendy crawled on her hands and knees to the first man. Ben quickly pulled his hard dick out as she whimpered, "I'm so sorry, sir. Muh...my ass is yours to play with." Then she leaned in and pressed her lips against the tip of his dick.

"Holy fuck!" Ben gasped as she gave his cock a long kiss.

Then she crawled to the next man. Another dick kiss. This time with a little tongue. As she crawled away he slapped her round ass hard. Leaving a soft red hand print.

So did the next man, and the next. Wendy crawled to each of her friends. Kissing dicks and getting spanked. Decisively showing everyone, including herself what her new role in the group was.

On the lounger, fat Tilda had pulled off Ian's dress. She was grinning and giggling as she watched Wendy humiliated. Her hand was in Ian's yellow, lace panties. She pinched and pulled on his tiny prick as Wendy debased herself.

Most of the men had pulled out their phones and were taking pictures of the beautiful naked woman as Grant made her pose.

"You want the boys to have something to remember this night by, don't you?" He asked her as he made her bend over a chair. "Wiggle that cute ass for the camera." He ordered. The naked woman obediently obeyed.

Over and over she posed. On her hands and knees, kissing Grant's shoe. On a chair, her legs wide, fingers pulling her pussylips apart. On her knees, squeezing her big tits together and licking her lips for the camera.

Tilda has stripped and forced the sissy to the ground. His face buried between her meaty thighs. She moaned and squeezed her own breasts as he licked her wet cunt.

The boys lifted Wendy up and placed her on another lounge chair. Hank pulled her arms above her head and tied her wrists to the frame, as Grant had told him.

Her cruel master leaned in and whispered in her ear as he pinched her nipple. "I want you to feel helpless for this next part." He pushed a rubber ball gag into her mouth. "You always thought of us as your friends. We always thought of you as another cunt to fuck." He gave her a sneer as he tightened the gag's strap.

Wendy's head was spinning as Hank lay down on top of her. Then she moaned as his big dick penetrated her helpless pussy.

The big man groped her tits. Squeezing unnecessarily hard as he fucked her. He grunted as his cock speared deep inside the bound beauty.

After Hank shot his load inside her she was mounted by the next. Ben happily gave her face a few slaps as his dick slid into her sloppy cunt. Then he moved on to her breasts. Smacking them back and forth. Enjoying the way they jiggled and bounced as she squealed into her gag.

Over and over the boys fucked and abused her. Running a train on her beautiful pussy. They had each taken some ED pills so they could fuck her more than once.

By the time they were done, Wendy's pussy was a gaping mess. Sore and caked with jizz. She had been brought to a handful of powerful orgasms, and lay there exhausted.

"Ah, ah, ah! Not time to sleep yet, you stupid cum dumpster." Tilda stood naked and large above the bound woman. She pulled the ballgag out of Wendy's mouth. "My turn."

The fat woman settled her bulk on the beautiful mess. Straddling the bound girls face. She rubbed her crotch against Wendy's lips, already wet from Ian's cunt licking.

Wendy obediently licked and sucked the fat woman's pussy. A slave even to other women's pleasure.

The boys laughed as Grant forced Ian to crawl between his wife's legs. Submissively the sissy began to lap up the Alpha's cum.

Grant stood behind the wimp and raised a leather belt. Ian squealed as he was whipped. The leather kissing a line of fire through his lace panties.

Finally the boys started to leave. Joking and marveling over the pictures they had taken, the abuse they had given, and the potential for the future.

Soiled and used, Wendy and Ian made their way back to their car. Then back home. They showered together and lay down in the master bedroom. Snuggling each other to sleep.

Monday Grant had his two pets in his office. A tall man with a thin mustache and an expensive suit sat on a chair in the corner watching.

"I'm very proud of the two of you. I think you are ready for the next step on your journey. Strip naked." He ordered the couple.

"This is Mr. Jorst." Their master explained as the pair quickly got nude. "He brought papers for you to sign that will annul your pathetic excuse for a marriage."

Wendy and Ian both gasped as they removed the last of their clothes. Grant grinned at the couple. Waiting to see if either would protest.

When they didn't all four gathered around Grant's big wood desk.

"Uhrum. Now. These papers state the marriage is unlawful as Ian has never been a proper man." The tall lawyer harrumphed at them. "Would you say that is correct miss?"

Wendy hesitated, then gave a slight nod. Mr. Jorst showed her the dozen spots on the document that she had to sign or initial.

When she took the pen and leaned down he grabbed her hips from behind. She gasped when he pushed her even further. The lawyer's long thin cock pushed easily into her pussy.

"That's it miss. Be a good girl and sign. Uhrum." He ordered.

There were tears in her eyes as she signed the papers. Though she didn't hesitate. Her tits slapped together as the tall lawyer fucked her from behind.

"Uh, hungh. Good, good!"

When she was done he pulled out and pushed her away. "Uma, now you boy." Mr. Jorst said.

Ian openly wept as he started to sign. The lawyer shoved his slimy dick far up his ass.

When Ian had signed all the spots the tall man kept him there. Pushing him so his chest was across the annulment documents. The sissy whimpered with each thrust of the man.

Finally Mr. Jorst groaned loudly as he came in the wimp. Then he stepped away. "Uh, ha. Very good then. You are both now single."

With a nod to the beaming Grant, the lawyer took the document and left.

"Wonderful." Grant said. Grinning down at his favorite toys. Ian and Wendy knelt on the floor. Hugging each other.

"Now the real fun begins." He told the two slaves.