Ian’s New Job Ch. 02

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Authors note- this story includes non-consensual, rough, and coerced sex. As well as straight and bi-sexual sex, crossdressing, and humiliation.


Wendy wore the shortest skirt she owned. A blue, pleated thing that stopped a few inches short of her knees. Underneath she wore red lace panties Ian had bought her for valentines a couple years ago, and never wore again.

She really didn’t have a lot of sexy clothes.

She wore a matching bra under a thin, button up blouse. Sheer enough to make out the outline of her bra. Nearly half the buttons were undone.

She sat quietly in the passenger seat as Ian drove. All too soon they were pulling into Grant’s driveway.

“It…this will be ok.” Her husband tried to assure her. Placing his hand on her shoulder. He had driven wearing nothing but a pair of black boxers. He hated to admit to himself that it felt weird to wear men’s underwear instead of panties.

Wendy just gave him a wan smile and stepped out of the car.

Grant smirked when he answered his front door. “My two whores.” He pulled Wendy into a kiss right there in front of the neighborhood. His hand slipping up the back of her skirt and squeezing her round ass.

Grant finally ushered them in. “Be a good little beta and offer her to me.” He ordered.

“I…uh…Grant, would you…would you like to fuck my wife?” Ian stumbled through words he never thought he would say.

“Not convincing enough, you pussy drip. Try again. And be humble.” Grant sneered.

“Grant, my pathetic dick isn’t good enough for my beautiful wife. I happily give her to you to use. Would you teach her how to be the whore she is?” The sissy obediently offered.

“Much better.” Grant grinned, pulling Wendy close. “Hear that? Your pathetic husband freely gives you to me.” His hand dug into her shirt, under her bra. Cruelly pinching and tugging at her nipple. “He doesn’t even try to fight for you.” All Ian could do is look down at his feet pathetically as his wife was molested in front of him.

Soon grant had pulled both her tits out. One arm around her waist, he lifted her skirt up and shoved his hand into her lace panties.

“You need to shave this, slut. A proper whore has a pussy as smooth as silk.” Grant tugged painfully at her curly brown pubic hairs.

Wendy grunted as the Alpha forced her to bend over the arm of his couch. He flipped up her skirt and yanked down her red panties.

She let out a long moan as his big cock entered her. She hated to admit that it really was so much more satisfying than her husband’s. It seemed to touch her everywhere inside. Pleasure everything.

Ian put his hands behind his back as his wife was fucked. His tiny pud getting stiff in his boxers.

Grant happily slapped Wendy’s ass in time with his thrusts. Slowly turning her pale ass pink, then red.

After he finally came inside her she just lay there waiting. Grant grabbed Ian’s hair and forced him to his knees. Shoving his sissy face in his wife’s sloppy twat.

Wendy moaned as Ian’s tongue gave her its own pleasure. Licking and sucking the Alpha’s cum out of her. Also pushing her to an orgasm. She pushed back and rubbed her used pussy on her sissy husband’s face as she gasped her pleasure.

When his two pets had finished Grant had them strip. Then he handed Wendy a strap-on with a big black dildo.

“Now you take another step in learning your proper place. Your husband is so pathetic, even his own wife is going to fuck him up the ass.” The cruel boss chuckled as the beautiful woman pulled on the fuck tool.

Ian submissively bent over the arm of the couch. The same spot his wife was fucked just moments before.

Grant handed the woman some lube. Wendy generously applied it to the dildo. Then to her husband’s ass.

“Tell your husband that he’s no man. You know what I want to hear.” Grant said from behind her. His hands reaching around to play with her big tits.

“Ian…you’re…you’re not really a husband. I’ve just been pity fucking you because you’re so pathetic. You couldn’t satisfy me like Grant can. This fucking should help you realize you aren’t a man in this relationship.” Wendy had tears in her eyes as she started to push the head of the dildo into her husband’s ass.

She felt terrible. Like she was betraying their vows. Their love.

For Ian, everything turned into the dildo burning its way painfully inside him. His little penis straining in its hardness. Turned on by his wife’s words as well as her violation of his manhood.

Grant chuckled. He sat down to watch as Wendy fucked her husband’s ass.

Wendy’s big tits jiggled with her thrusts. She winced every time she shoved the dildo into her husband’s ass. His painful, girly whines like claws on her soul.

Eventually Ian drizzled his little cummies down the side of the couch. Grant pulled Wendy off him and made the sissy lick it up.

Grant took their clothes and threw them out his front door.

“Time for my casino siteleri whores to leave. Buy some sexier clothes and shave that forest.” He ordered them pushing the couple out the door. Naked and soiled.

Quickly they tried to cover their nudity. Humiliated and scrambling to the car.

“I…I’m so sorry about that, Ian.” Wendy started to cry. “I didn’t mean any of it.”

Ian hugged her close. “Ssh. I know. It’s ok. We are going to both do things that may hurt. Besides, it kind of turned me on to have you dominate me.

When they got home they showered together. Doing a lot of kissing. Then Ian carefully shaved his wife’s pussy bald. Kissing it lovingly when it was smooth.

Together they went out shopping for a new wardrobe. They started with Wendy. She picked out some shirts and skirts that were more risqué than usual. Then she picked out a bunch of lingerie. Silk and lace. Thongs and nighties.

The beautiful wife shivered every time she pulled on a thong or bikini bottom or shorts. Her newly shaved cunny tingled with excitement at each touch.

For a few minutes she simply sat there, nude in a dressing room. Brushing her bare softness and trying not to moan.

Wendy spread her legs wide. She thought of Grant as her fingers dipped into her honey pot. She should have been buying these sexy clothes for her husband. To please him.

Instead they were for Grant. Evil Grant and his big cock. She bit her clenched fist and shuddered through a small orgasm.

Her sissy husband waited patiently on the other side of the changing room door.

Then it was Ian’s turn. They only picked out clothes from the ‘ladies’ section. Skirts and dresses. Blouses and lingerie.

Ian blushed every time he stepped out of the dressing room to show off. His tiny pud hard with excitement.

Wendy was horrified to find part of her enjoyed treating him like this. horrified and aroused. The whole naughty afternoon was turning her on. Her husband emasculated before her.

Here it was just her and him. There was a spicy intimacy in his humiliation before her. One that was taken away when they were with Grant. Stolen.

“Looks like someone likes dressing like a girl.” She said, stepping close and reaching under the short skirt he was showing off. Her fingers found his hard prick. She tugged him as he licked his lower lip in excitement. “Ok, back in there you pathetic sissy.”

That evening when they got home, Ian immediately changed into a short skirt and silk blouse. He shivered as he pulled on lace panties and white stockings.

Wendy found she couldn’t keep her hands off him. Reaching under his skirt to squeeze his ass or pet his dick. Running her fingers up and down his smooth blouse.

She quickly changed into a sheer nighty and silk thong with stockings that matched Ian’s.

After dinner they made love long into the night. Fully aware that Grant would continue to pervert their relationship. Their sexuality.

“Please, Amy. I’m just a worthless whore. My pathetic, sissy husband needs to learn his place. I want you to do whatever you want with him.” Wendy was on her knees before Ian’s ugly fat co-worker.

Both she and Ian were stripped down to their lingerie. It was Monday morning and she had dropped her husband off. Ian wasn’t allowed to drive any more.

“That’s far too masculine for a wet sissy like him.” Grant had told them. The cruel man now standing behind them grinning at this new humiliation he was forcing on them. Making Wendy offer her loving husband to another woman.

“Ha! What a dumb cunt.” Amy said. She reached down and slapped Wendy across the face. Causing the submissive girl to gasp with shock and a strange excitement. “Sure, I’ll teach your worthless, twat, husband a thing or two.”

The fat woman grabbed Ian’s hair and painfully pulled his face to her crotch as she sat down. The sissy obediently tugged down the big woman’s jeans as Grant pulled Wendy to the door.

The brunette couldn’t take her eyes off her husband until the door closed behind them. Her last glance was of Ian licking and kissing the fat woman’s thighs. A tender act that used to be reserved for her alone.

But then, so was what she was doing for Grant. Moments later she straddled his bare lap. Her panties on the floor. Grinding her pussy against his big, hard, dick. She couldn’t stop shivering as his fuck rod caressed her newly bald cunny. She felt strangely vulnerable, sensitive.

He was sucking then biting her hard nipples. Savoring her submission to his every whim.

“We are going out to eat tonight, whore.” He informed her, gripping her hips tight. “You will dress like a total slut. So will sissy Ian. I want you both to be humiliated when we walk into that restaurant, understand?”

“Mmm, yes sir.” She moaned. Her body trembling.

“And you will take the bus, so as many people as possible will see my fuck toys.”

Wendy gasped loudly as he finally shoved his cock deep in her. She rubbed canlı casino her big tits against his face.

She still had to get to work, but for the moment had lost herself in the perverted sex that Grant forced her into.

Wendy picked Ian up after work and took him to a couple stores. She had decided they would pick up some especially slutty clothes for their dinner.

She picked out a short, tube dress for her sissy husband. Shiny silver and it didn’t quite cover his ass. He was continuously tugging it down.

He also had fishnet stockings and a tiny lace thong that had a problem keeping even his tiny pud covered.

Wendy picked out a leopard print top. Basically just two straps that barely covered her nipples and then met to wrap around her waist.

Her tits were less covered than when she went to the beach. They jiggled and bounced whenever she moved. The shirt and lack of bra offered no support. She needed to use special tape to make sure her nipples stayed covered.

For a bottom she wore a short schoolgirl’s skirt. Like Ian’s it didn’t quite cover her round ass. She wore a silk thong that offered her a little modesty. Though none for her derrière.

She also wore fishnets. They matched her husband’s. Something about that comforted her. An intimacy they could share.

Wendy figured they would need to find ways to share that intimacy. It was obvious that Grant intended to strip away the bonds that most couples took for granted.

They both had black, high heels. Stilettos. Neither were super comfortable walking in them. Ian was just barely used to regular high heels.

They both stood looking at themselves in the mirror before leaving. “I don’t know if I can do this.” Wendy said. She barely recognized the woman staring back at her. Her long brown hair was now up and she looked like a prostitute who was trying to move upscale.

“I know, honey.” Ian gave her a loving hug. “Grant wants to tear down our resistance. This is another step in that. If we can dress like this in public, we will dress like this anywhere.”

She nodded a bit sadly. What were they becoming?

Wendy and Ian blushed as they stepped on the bus. They got a lot of stares. And no small amount of lusty grins. Wendy couldn’t help shivering with excitement. Somehow what she was wearing was even more humiliating than if she had boarded the bus fully nude. She kept reaching up to stop her giant tits from wobbling. Which merely drew more attention to the large pendulous orbs.

They met a beaming Grant just outside the fancy restaurant. “Excellent. You both look like complete whores.” He said as he pulled Wendy in for a kiss. Squeezing her round bottom under her short skirt.

Wendy shivered as they walked into the restaurant. Well dressed men and women sat eating and chatting at tables. When they looked at her it was with obvious disdain. Like she was worthless. Gutter trash to be used then tossed away.

She tried to keep her head down through the meal, but couldn’t help looking up to see who was watching. She shivered every time she made eye contact. Feeling dehumanized and more worthless each time.

By the end of the meal a change had come over her. And over her sissy husband. The humiliation had swallowed their egos. Leaving them even more timid and submissive.

After the meal, grant took them back to the kitchen. He had made arrangements ahead of time. Otherwise they wouldn’t have been allowed in the restaurant in the first place.

“I want you to masturbate in front of these men.” Grant grinned at his pets. “Show them just how slutty you are.”

The couple simply mumbled ‘yes sir’ and lifted their short skirts. Cooks and busboys grinned as they looked at Wendy’s shaved cunt. Then a small cheer went up as she started to finger herself. Ian pulling on his tiny bump next to her.

Wendy made eye contact with each man. Knowing that if any asked she would willingly fuck them in front of her husband. Knowing he wouldn’t protest.

Neither lasted long. When done Grant ushered them out the back into the dark alley. Chuckling as the kitchen door closed on them.

Dejected at what they continued to become, they made their way home.

Wendy had been ordered to wear inappropriate clothes to work by her master. After the Monday night dinner she had little choice but give in.

Wednesday she found herself stepping into an important client meeting. Wearing a blouse that exposed an indecent amount of her massive cleavage. As well as a skirt that was immodestly short and slit up one side, showing off the top of her stocking.

Her partner in the meeting was Bev. An older woman who Wendy had beaten out for a promotion almost a year ago. They had been bitter rivals before that. Now they were active opponents. The older woman took every opportunity to undermine Wendy’s work.

The older woman gave Wendy an astonished look when she saw how she was dressed. The men in the meeting couldn’t stop staring at the submissive kaçak casino woman’s tits.

As the presentation dragged on, Bev took more and more control. Something Wendy would have successfully defended just a week ago.

Now it was almost as if she was the older woman’s assistant.

The clients certainly seemed to think so.

After they were finished, the men shuffled out. The two professional women gathered their materials up.

“You’ll be fired if I let on how you came dressed today.” Bev announced from behind Wendy. “You look like a tramp.”

The beautiful brunette didn’t defend herself. She just continued arraigning files. Keeping her head down.

Bev grinned. She could sense some sort of change in the younger woman. It was obvious she could exploit it. But how?

Bev wanted to humiliate the girl like she had been humiliated when she was passed over. She grinned at Wendy’s back. Her round ass nearly exposed by her short skirt as she bent over the table.

Bev felt an amazing sense of power and exhilaration as she swatted the young woman’s ass. Wendy’s head jerked up and she gasped in surprise.

“You aren’t better than me now. Are you, whore?” Bev asked. She grabbed the woman’s long brown hair and swatted her again. “Are you!” She demanded.

“N…no ma’am.” Wendy responded meekly. “You…you are obviously my…superior.” She squeaked as another blow landed on her rear.

“You have everyone fooled, but not me.” Bev said as she lifted Wendy’s skirt up past her round ass. Revealing two beautiful pale orbs hugging a silk thong. “What a whore. You’re just a lying, manipulative bitch. Probably slept your way to your position. Didn’t you!” The older woman continued to punctuate her words with sharp slaps on Wendy’s now bare asscheeks.

Wendy winced as her derrière was punished. Her pale flesh slowly turning pink. It wasn’t true. She was a great employee. She had worked hard to get where she was.

Of course, where she was, was bent over a table getting spanked by a co-worker.

Wendy clenched her eyes shut in shame when she said, “Yes. That’s right. I’m terrible at my job. I…I manipulated and…and used my body.” There were tears in her closed eyes when she admitted, “I’m a complete whore, and don’t deserve my job.”

Bev let out a laugh of triumph. She shoved Wendy to the floor and walked out in victory. “Whore.” She hissed back over her shoulder as Wendy sobbed.

Grant was slowly and successfully dehumanizing the young couple. Ian was further along than Wendy. Things like wearing women’s clothes all the time and not being allowed to drive, constantly ground away at his ego.

Wendy was quickly catching up. Complaints about her dress had been made at work. Yet she continued to dress like a whore. She was sure to lose her job soon.

Grant had dreamed up some new humiliations for her. They were to be done mostly in private. Simply a way to show her that she was his belonging even when he wasn’t there.

The first…Quiet Time. Between four and nine in the evening, on weekdays, she was to wear some form of ball gag.

“Whores are to be seen. Not heard.” He had told her. “Society has incorrectly taught you that should have a voice.” Her cruel master had chuckled at that.

He even ordered her to do her grocery shopping in the afternoon. Wendy would be humiliated. Feeling dehumanized with the ball gag in her mouth. Other shoppers staring and smirking at her.

The second private humiliation…T-mail. Before she could take the gag out she had to undress, alone in her room. Then she had to run a strip of duct tape from the top of her bald pubic mound, down to cover her bare cunny. Then a piece each across her big breasts. Making sure to cover her nipples.

At her leisure she was to tear the tape off. Fast or slow, was her choice. First her breasts. Then her pussy. Always leaving her skin raw and burning.

The tape across her crotch was then to be mailed to Grant.

She found it humiliating to have to write out his address, then list the number of hairs pulled on the back of the envelope. Usually ‘zero hairs’ as Ian plucked her nearly every day.

The third humiliation was that they were to keep separate rooms. The master bedroom was to belong to their master. During the week they had to sleep alone in their own rooms. Their house was just big enough, after converting Wendy’s office.

Only on the weekend were they allowed to sleep together in the master bedroom.

Also Wendy was no longer to cook at home. Ian was told to do that. He had a pink apron with white frilly edging. And the words ‘the dutiful wife loves to serve’ printed on it.

Each day they were shown just how submissive they were. Reminded that Grant owned them. Controlled them.

It was Friday afternoon. Wendy had stopped by to pick up her sissy husband from work. Earlier she had been given a last warning at work for dress code violations.

Grant had quickly fucked her over his desk. pressing her big tits and her cheek against the hard wood as he thrust into her. Then he took his naked pets to the breakroom.

There he led them to a metal skillet on the counter. Set on a big hot plate it was noticeably making the room warmer.

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