Sissy Bitch Goes To Dinner free porn video

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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.

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Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm List of Characters. Me. Michelle A Natural transvestite sissy. Janice My Younger sister Aunty Bev Janice and My mother's Sister. Mistress Janet Headmistress of the young lady's academy Doctor Shirley Williams. My endocrinologist. Miranda. A very effeminate Sissy sales assistant. Miss Stern Miranda's mistress who owns the shop. Peregrine AKA Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James AKA Auntie Jamie Peregrine's...

1 year ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty...

4 years ago
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Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

2 years ago
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Sissy Rules Reads like a proper job description

(Found this on the internet... #65 seems especially made for me) Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows...

1 year ago
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Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

2 years ago
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Sissy Julian Chapter I Beginnings

Here we go again. Some boys simply are sissies. This is the story of one of them. It is not a story of discovery, although there is much of that, but rather a tale of a lovely boy's trip to self-realization, albeit a tad 'forced.' If lots of frilly sissy boy and girl outfits, super swishy behavior and a little sex, not to mention dominant women, are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fictional fantasy work. No references...

1 year ago
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Sissy Crissi Chapter 3 Leroys Turn

Chapter 3 - Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers...

3 years ago
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Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

4 years ago
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Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

4 years ago
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Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

2 years ago
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Sissy Farm Chapter Twelve

Sissy Farm - Chapter Twelve By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA....

4 years ago
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Sissy Sally

CAUTION: This is a forced fem story. If this is not your thing, please move on. All rights reserved. Sissy Sally Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house-...

2 years ago
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Sissy discovers Part 4

the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...

2 years ago
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Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

1 year ago
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Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

3 years ago
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Sissy New Year

Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

1 year ago
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sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

4 years ago
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Sissy Arm Wrestler

Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

3 years ago
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Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

3 years ago
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Sissy Farm Chapter TwentyOne

Sissy Farm - Chapter Twenty One - By: Beverly Taff List of Characters. Me, Michelle: A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Doctor Shirley Williams: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine, AKA. Uncle Penny: My transvestite uncle. (Aunty...

3 years ago
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Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

2 years ago
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Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
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Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

2 years ago
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Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

1 year ago
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Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

3 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

1 year ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

1 year ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle. (Aunty Bev's brother.) James: AKA. Auntie Jamie, ...

1 year ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
1 year ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

3 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

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