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Sissy Bitch goes to Dinner

Anthony takes Nicole to dinner and meets the secretary he harassed earlier.
Anthony sat at his desk, glaring at his secretary. Although the poor woman had done nothing to invite his ire, he continued to berate her. She stood there in tears, hoping to keep her job, even though she knew that it was a hopeless cause. As she waited for the ax to fall, Nomi silently thanked the Lord for her back up job at Chez Louis, an upscale restaurant in the city. It didn’t pay as well as this job, but it was all she had left now.

“This is the second time this year that you have been late with the reports, Nomi, and that isn’t acceptable to me,” he barked.

“I know, sir. I’m sorry,” she stammered.

“Pack up your stuff and go. You knew when you hired on that I demanded promptness…professionalism. I have given you one too many chances, as is,” he said, dismissing her from his office.

Nomi turned on her heels and stomped out. She needed this job, but damn her if she begged. It was true that she was late with his report. He wanted it on his desk at five pm. She looked at the clock. It was only 5:03, and that was after she got her ass chewed for two and half minutes.

“Fuck him. He can kiss my lily white ass,” she said, aloud.

Nicole, who had been waiting in the waiting area, observed the upset blonde. Wanting to surprise Anthony, she had showed up unannounced and witnessed him in asshole mode again. Displeased, she approached the woman.

“Are you okay?” she asked.

“Huh? Oh…yeah. I’ll be fine. Are you here to him?” Nomi replied.

“Uh huh, but I don’t have an appointment,” Nicole admitted.

“Go right in. I’m sure he is just sitting there gloating in his supreme maleness,” Nomi laughed, grabbing the small box of her things.

Nicole smiled. While talking to the pretty blonde, she noticed a waitress uniform for Chez Louis’ in the box. A naughty plan blossomed in her head, and when the waiting room was empty, she called the restaurant and reserved the private dining room. Before hanging up, she requested Nomi to be their only server. Dearest Anthony needed a lesson on how to treat people with courtesy and leniency.

“Such a bad, bad boy, you are,” she said, stepping into his office.

Anthony’s head snapped up. Startled, his heart beat doubled, as his beautiful Mistress closed the distance to his desk. Just the mere sight of her made his cock harden painfully, but to be truthful, his cock had been hard all day. The silk of the pink panties made his every movement agony by caressing and tickling his shaft. Now, fully hard, he could feel the elastic band cutting into his flesh, as the thick mushroom head peeked out the top.

Nicole watched him squirm and wiggle. He looked like his ass was on fire. Frowning, she stared directly at him.

“What the hell is wrong with you? Sit still,” she snapped.

“I’m sorry, Miss. It’s just that these panties are uncomfortable,” he admitted.

“So…you did wear them. Good. I’m glad you did as you were told, but I am displeased with how you treated that woman back there,” she admonished.

“Who? Oh, you mean Nomi? She was late with her paperwork and…,” he began.

“How late?” Nicole interrupted.

“It was due at five,” Anthony answered.

“Five, huh? AM or PM?” she persisted.

“PM,” he admitted.

“It’s what…5:15 now? Don’t you think you were a bit harsh?” Nicole said, angrily.

Anthony opened his mouth to say something, but was cut off when she held her hand up.

“I don’t want to hear your lame ass excuses. You were a bad boy and need punishing,” she said, “Now…get up and drop your pants.”

Anthony’s shaft got harder, if possible, as he rose from his seat. As his pants pooled around his ankles, he dared to look up at her. He could only imagine how he looked, standing there in those silky panties; half of his cock was escaping from the top and his sac spilling out of the crotch. He watched her reach into her purse and pull out something flesh colored. Pre cum oozed from his slit, as she walked behind him and sat in his chair. She eased the panties down to the middle of his thighs.

“Lie on your desk, and then reach around and pull your ass cheeks open. Wide,” she said.

From her view point behind him, she could see his tight, brown sphincter. His body was trembling, as she pulled his cock down, wedging it against the desk. A large drop of pearly fluid hung from the tip a moment before falling to the floor. Nicole blew a puff of air across his rosebud, making it wink at her.

“Wider, Anthony!” she demanded, when his grip slackened.

Using her fingers, she smeared the pre com drooling from his dick all over his purple glans. Once it was shiny with his fluids, Nicole pulled his foreskin up and over the plum. She stimulated only the head, just by using his foreskin. Goose bumps formed along his spine, causing him to shiver. Lost in this sweet torture, Anthony nearly exploded when he felt her warm, wet tongue probe his ass.

“Ughhhh,” he moaned.

Her tongue pushed deeper; relaxing his hole. He gripped his desk, surprised that he hadn’t splintered the wood. His cock leaked; saturating her hand and making it slipperier.

Nicole tongue fucked his ass, until he was nice and relaxed; close to cumming. Then, pulling her tongue free, she eased the tip of a large butt plug into Anthony’s loosened anus. The wrinkles surrounding his ass hole began to smooth out, as the toy disappeared into his gut. Once the flared end of the plug cleared, his hole snapped closed.

“Nice. Your greedy asshole just swallowed my toy whole. Wanna see?” she asked.

“Yes…please,” he moaned.

He had often tried to take pictures of his ass when he played alone, but they always turned out blurry and horrible. Anthony stayed as still as he could, as she snapped the photo with her phone. A few seconds later, he phone alerted him about a text message. Nicole eased the pink panties back up; pulling them snug against the toy. Helping him stand back up, she watched in amusement, as he tried to reach his pants without pushing the toy out. Taking pity on him, she pulled them up enough for him to fasten them.

“Ready for dinner?” she asked.

“Uh…yeah,” he answered, unable to focus on anything, but the incredible pressure blossoming in his ass.

“Well, c’mon,” she said, slapping his ass.

Anthony groaned. The simple slap nudged the tip of the butt plug against his prostate. Just the normal act of walking had the toy massaging every sensitive spot he had. His rock hard cock was oozing large globs of juice, and he knew the entire front of his pants would be soaked by the time they made it to the restaurant.

The ride was exquisite hell. It seemed to him that Nicole chose the bumpiest roads. He wanted to cum so badly, and a few times, almost did. As they walked up the path to the door, he hoped that no one would notice the tent in his pants. The flimsy silk was not strong enough to hold his cock in place, so with each awkward step, it bounced. He followed her through the crowded dining room, waiting patiently as she stopped to talk to different people. Anthony kept his eyes forward, as he knew everyone was aware of his aroused state. The huge wet spot surrounding the tent was plainly obvious, but despite the fact that he was embarrassed, his cock remained hard as iron and all he wanted to do was blow his load.

Once they were seated in the private dining room and behind closed doors, she turned to him and asked, “Excited?”

“Yes, Miss. Very much so,” he agreed.

“I’ve noticed something about you. You act like a complete dick to women, especially those you are attracted to,” she said, idly playing with the silverware.

He sat, silently.

“Take Nomi…blonde, tall, beautiful…not to mention stacked. You were a fuck wad to her, but truthfully, you wanna fuck her, don’t you?” Nicole asked.

“NO! I would never do that to you, Mistress!” he said, alarmed.

“You are such a liar!” she laughed, “If you don’t want to fuck her, then what do you want?”

“Well…I want…uh…,” he stuttered.

“Jesus Anthony, if we’re gonna have this type of relationship, then you need to be honest with me,” Nicole sighed.

“Okay…I don’t want to fuck her. I want her to fuck me,” he admitted.

“Thought so,” she smiled, enigmatically.

About that time, Nomi walked through the doors. She had been excited about this assignment, until she saw who was sitting there. She just could not get a break. Normally, when one works the private dining room, the tips were awesome. It was just her fucking luck that Mr. Motherfucking asshole was her assignment. They locked eyes; her guarded and his wide.

“Hi Nomi. I am so glad that you’re our server tonight. It’s sure to be a night to remember,” laughed Nicole.

She motioned for the woman to come closer.

“Now Anthony, where’s your manners? You’re supposed to stand when a lady approaches the table,” Nicole scolded.

He hesitated, sighed, and then stood up. Staring at the wall behind Nomi, he heard her gasp. Knowing that she had seen the large wet spot surrounding his rock hard cock, his face flushed red.

“Sit down, Nomi. He’s quite docile,” Nicole urged.

Nomi dropped into the vacant seat; her mind swirling. Something was amiss here. It didn’t take a rocket scientist to figure that out. She listened to the stunning brunette order a salad, with a large, thick cucumber on the side. Nomi stared blankly. Had she heard right? Did they want the cucumber whole…not cut up? She glanced at her former boss, still standing, and noticed that his tent was bobbing.

“When you return, please stay? I’ve informed your boss that we wish to have you as our only server,” Nicole grinned, mischievously.

Nomi nodded, and then went to order their food.

“When she returns, you will apologize for your rudeness and give her another chance. Just because a report is thirty seconds late is no excuse for firing someone,” Nicole told him.

“But…,” Anthony fumed.

“No buts! All you were doing was showing how big you thought your dick was. Be a real man!” she snapped.

“I’ll apologize, but I won’t rehire her. NO,” he growled.

Nicole just looked at him; disapproval plainly visible on her lovely face. Anthony felt his armor crack. He knew that he would end up doing exactly what she wanted in the long run.

“Fine…I’ll do it,” he grumbled, shoulders slumped.

“Thank you. It really means a lot to me,” she smiled, “Now…take those pants off and put this on.”

Anthony stared that the garter belt and hose in her hands. With shaking hands, he took the lingerie from her, and then looked at her; confused. She shook her head, sighed, and then explained.

“Okay…strip down to your panties. Good…now strap the garter around your waist…yes…like that. Sit down and pull the nylons on, but be careful not to ruin them,” she said, guiding him along.

“Before you fasten the nylons to the garter belt, you need to remove your panties first, and Anthony…I better not see that ass plug fall out,” she warned.

He straightened up; dick hard enough to cut glass. It never occurred to him that the feel of silk stockings would be so erotic. Of course, he loved them on women, but damn! If he knew then, what he knows now, he would have started wearing them sooner.

“We really need to shave you,” Nicole remarked, handing him a different pair of panties.

She watched silently, as he stepped into the tiny thong and pulled it up. Her pussy plumped just from the sight of him standing there in a white garter with matching stockings. The tiny triangle of white silk did nothing to hide his thick cock. His heavy ball sac was separated by the string that disappeared in the crack of his ass. He looked so erotic…so like the sissy bitch that she knew and loved.

“How do you feel?” she asked; voice husky.

“Sexy…horny...,” he admitted.

“I want you to tell Nomi your secret. Beg her to fuck your pansy ass with the cucumber,” she ordered.

“Yes, Miss,” he said, shivering.

He waited patiently for the blonde to return. Within about ten minutes, Nomi reappeared carrying a large salad bowl, which she immediately dropped. Scrambling to her knees, she started to clean up the mess, when Nicole stopped her.

“No…It’s okay. Let him do that,” Nicole said.

Nomi stood up and watched Anthony walk, stiffly, toward the mess. When Nicole asked her sit down, she slumped into the nearest seat. She didn’t know what to think of the situation, but would be lying if she said she wasn’t a little turned on. Knowing a little about D/s, she had always wondered what it would be like to dominate a man, but never acted upon it.

“Anthony…don’t you have something to say to Nomi?” Nicole said.

“Um…yeah…I guess,” he mumbled.

“Well, get that mess cleaned up. Be quick about it! We don’t have all day,” Nicole snapped.

Nomi stared in astonishment, when her hard ass ex-boss quickly dropped to his knees and started picking up stray bits of lettuce and carrots. Her gaze was drawn to his ass; high in the air. Tilting her head to the say, she leaned forward; staring hard at the strange pink thing wedged snuggly in Anthony’s ass.

“Is that what I think it is?” she asked Nicole.

“Yes…dear Anthony likes to put things in his ass. Want a closer look?” Nicole laughed.

Anthony’s cheeks burned. He listened to the women discuss his fetish and blushed harder when his cock bobbed from their discussion. He obediently crawled to their feet when the mess was cleaned up and waited for his Mistress to give him further instructions.

“Um…I…uh…I apologize for treating you…like…shit,” Anthony mumbled.

Nomi’s left eyebrow arched sharply in disbelief.

“There that wasn’t so hard, now was it?” Nicole crooned.

Anthony sat there; gritting his teeth. His facial expression told her just how hard it was to apologize to Nomi.

“Isn’t there something else that you wanted to say?” Nicole gently prodded.

He remained stubbornly silent.

“Hmm…it seems that the apology took a lot out of him. So…I’ll have to be the one to tell you the big secret, Nicole remarked.

“It’s no secret that Anthony feels that women are beneath him, but have you ever noticed that he only treats certain women like crap? For example, when I met him, he thought that nurses were fuck toys. Imagine his surprise when I made him my fuck toy. He was just saying that the reason he treats certain women like that is because he wants them sexually,” she continued.

“So…he wants to fuck me, huh?” Nomi replied.

“Oh no no no! He wants you to fuck him,” Nicole answered.

“Holy shit! Mr. Tight Ass wants to take it in the ass. Is this true?” Nomi asked Anthony, “You want to feel my fingers wrap around your cock…very nice cock? What else do you want me to do?”

Anthony’s chest heaved; cock bobbed harder, as he said, “I won’t deny it. Yes, I want you to do things to me.”

“Now c’mon…grow some balls and tell me what you want,” Nomi persisted.

Anthony noticed that Nomi’s nipples were erect; poking out sharply. A faint red flush covered the exposed skin of her chest. Growing braver with the knowledge that she was as turned on as he was, he looked directly into her eyes.

“I want you to play with my ass. I cum hard like that,” he admitted.

“Let me get this straight. You want me to fuck you like a bitch, and what do you propose I do it with; seeing that I don’t have a spare cock with me?” Nomi asked, breathlessly.

“Would this do?” Nicole prompted, holding up the cucumber.

Nomi took the vegetable from her hands and looked at it. It was sturdy, thick, and long; definitely able to withstand plunging in and out of an ass. Especially since it seemed that his ass was already loosened.

Nicole studied the woman. She was breathing heavy; eyes glazed, but had the uncertain look of where to start. Vacating her seat, she went around the table behind Anthony.

“I imagine that her pussy is already nice and wet, Anthony. Why don’t you check to see if I’m correct?” Nicole told him.

Looking at Nomi, he waited for her permission. She lifted her skirt to her waist and scrambled out of her panties. When she sat back down, he pulled her to the edge of the chair and spread her thighs. Rubbing his cheek over the satiny soft skin of her inner thigh, he breathed in the pungent scent of her wet pussy. Drops of pearly fluid gathered along the seam of her hairless labia. He was unable to resist their call, so he leaned closer and plunged his tongue between them. Nomi gasped. Just the feeling of his strong tongue scooping out her creamy fluids had her clit buzzing madly. She reached down and opened her iris with both thumbs and watched his tongue disappear into her dark canal.

“Suck my hole,” she said, and then groaned when he wrapped his lips around her entire inner labia and sucked hard.

Her fingers f0und her pulsing clit and rubbed hard. It had been so long since she last came that she knew this one was gonna be big. Using her thumb to retract the loose skin covering her bud, she trapped the sensitive flesh between two fingers and jacked it like a tiny cock. She was so close. Just a small push would send her over the edge.

“Put your thumb in my ass,” she panted; fingers never stopping.

The sensation of her ass being penetrated sent her over the edge. Bearing down hard as she came, her muscles contracted and squirted warm, sticky, clear fluid all over his face. Anthony’s tongue tried to catch every drop, but the jet was too quick, and he ended up with much of it dripping from his nose and chin.

“Nice. I didn’t expect a squirter,” Nicole praised.

Anthony looked up from her crotch, expectantly.

“One good turn deserves another, but since you like being treated like a bitch, I want you to leave my cum all over your face,” Nomi said, after catching her breath.

“Anthony, lean over the table. Good…just like that. Stick your ass out further, and spread those legs,” Nicole demanded.

Nomi stood behind him and looked over to Nicole, who told her to start by removing his thong panties. The gentle nudge was all she needed. Once his lacy thong was lying on the floor, she touched the butt plug in his ass; making him flinch. She grabbed the flared base and pulled slightly, watching his hole stretch, but let it bounce back into place. She knelt down and looked at his dripping dick. Large white globs splashed to the floor every time she touched the plug.

Nomi stood back up straight, and this time she pulled the plug out completely. Anthony howled; dick standing up. She watched, as his slack anus remained wide open; quivering. Slowly, the muscles of his sphincter drew closed; not all the way closed though. She grabbed the cucumber, which was at least two times thicker than the plug. The chill of the still cold veggie made his rosebud flinch. She pushed the tapered end into his pucker. It sank half way inside his gut instantly. Surprised, she had expected more resistance.

Nicole chuckled at her expression, and said, “I know…he’s an ass slut, but that’s what I love about him…my sissy bitch.”

Nomi focused back on the grunting man in front of her. Mesmerized by how wide open he was getting, she pushed the vegetable in further and reached her hand around him. Resting it on his lower abdomen, she pulled out the cucumber, and then back in. His belly bulged and sank with her rhythm; cock knocking at her hand.

“Faster…please…,” he groaned.

Nomi braced her hand on the table and used her entire arm to work it in and out of his gut. She slammed his ass hard, making him grunt and moan. Not wanting to hurt him, she drizzled the oily salad dressing over his paper thin anus and worked it in with the cucumber. By then Anthony was gibbering nonsense and close to exploding. She wedged the green toy in his ass, telling him to hold it there with his ass muscles. He held on tightly.

“Stroke your cock, Anthony. I want you to cum all over the floor, as I spank your rude, woman hating ass!” Nomi growled.

Anthony’s hand danced up and down his shaft. His cock got harder; glans dark purple. She slapped his ass cheeks, jarring the cucumber buried deep inside. The redder his ass got, the harder the vegetable nudged his prostate. He could feel his hot fluids racing up his large vein. As the first gushes of cum erupted from his piss slit, the cucumber was pushed out of his anus and dropped to the floor. His bruised hole twitched; skin a deep purple.

She looked at her ex-boss, who was bent over a table; ass red, asshole agape, and standing in a puddle of his own cum. She wiped her hands on his face.

“He wants to offer you your job back, Nomi?” Nicole said.

Having forgotten the woman was still here; she jumped, and then said, “Thank you, Nicole, and thank you, Anthony. This was indeed a night to remember, but I have to decline the job offer. There is no way in hell that I would go back to the abuse you like to dish out at work.”

With that being said, she left the room. Nicole glanced at the prostrate man and sighed deeply. She helped him get dressed and ready to leave.

“Wow…I didn’t expect her to turn you down. Oh well…live and learn,” Nicole remarked.

Anthony sat gingerly in the seat. His ass was on fire again, but he never felt so relaxed. As she drove through town, he wondered when he would get to fuck her.

This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than Lushstories.com with this note attached, it has been posted without my permission.

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