The Matriarchy Tales: Sissy Willow

Author's note: In this series, each addition will be a stand-alone story and will be longer than a chapter in one of my other series. This tale is for one of my fans who messaged me about a year and a half ago, who goes by the name Willow when she's in her sissy mindset, and I hope she enjoys my take on one of her biggest fantasies.

It was Friday morning and she looked into the mirror to examine her makeup. Her dark eyeshadow and long, black eyelashes made her baby blue eyes jump right out at her. Her lips were made bright pink with lipstick and her cheeks had a subtle amount of blush, making her quite attractive for a sissy who couldn't quite pass as female.

Not in the face, anyway.

The rest of her body, though, was a genetic lottery to her. Being 5'7" tall and weighing as little as 135 pounds, it made finding women's clothing in her size very easy. She had quite the assortment of bra's, panties, dresses, skirts, and blouses, as well as less revealing slacks and jeans, but her favorite were her french maid's outfits. She had one in the classic black and white style, but she absolutely LOVED the one in pink satin and white cotton because it made her feel more like a sissy.

And that's the one she was currently wearing, along with white thigh high stockings, white lacy (and crotchless) panties covering the small pink cage that contained her clitty, and pink, four-inch 'fuck me' pumps. In addition, she had a white bra with c-cups encasing her adhesive-free breast plate, which she thought was a must for sissies. It was customized to her body size and skin tone, and with a variety of nipple sizes and shapes to choose from for the finished product, she went with small areolas and thick nipples, just like the love of her life. With some light makeup touches, the casual eye could easily miss where she ended and the fake breasts began.

She chose a breast plate over breast forms because the sexiest outfits usually showed off plenty of cleavage. Especially the revealing necklines of her maid's outfits. Looking down at herself in the mirror, she pushed out her chest and smiled at the sexy result. After playfully grabbing her fake breasts with her delicate hands and manicured nails coated in pink nail polish, she reached over to the faceless head on the corner of her makeup table and grabbed a hold of her long blonde wig with bangs that covered half her forehead.

She set it on her head and adjusted it until it sat correctly without looking like a wig, and then secured it to her real hair with bobby pins until she could pull on it without it coming loose. Then she slid the pink maid's headpiece on top and began looking herself over.

The maid outfit's sleeves barely came down to the halfway point of her slim upper arms and had white ruffles similar to the petticoat at the hemline. The white apron covered the majority of the front from the waist below and the skirt of her outfit flared outward enough to cover up her not-so plush rear. Any other time, especially with her women's jeans, she'd wear padded panties to help give her butt a more feminine shape, but her job as a sissy maid required a little more access to her hindquarters then that style panty would allow.

After examining her chest and cleavage once more, she turned to the side and looked at how the maid outfit contoured her slim abdomen. She then tilted her vanity mirror down and stepped back to examine how her legs looked in her white stockings. Liking what she saw, she lifted the back of her outfit to check out her ass and smiled to herself.

"You're such a sexy little sissy!" she said to herself, then smiled at how her life turned out.

She had her own sissy bedroom where the walls were painted hot pink, and her bedsheets were a floral pattern on a white background. Her bed was only a full size, but it was comfortable and very intimate during the rare times she had company. Her oak dresser sat against the wall about four feet from the foot of her bed and had a 42-inch TV on top so she could watch all her favorite sissy videos without getting up. Her closet was small, but full of her girlie outfits and a decent selection of shoes. Overall, it wasn't much, but it was a good sissy's bedroom.

She adjusted the mirror back to where it was, grabbed her pink purse, and exited her bedroom. Walking down the hall, she looked inside the master bedroom where her wife slept and saw that the bathroom light was on. Walking toward the master bathroom, she peaked inside.

"Hello, Mistress." she smiled, using her practiced feminine voice.

"Hello, my sweet little sissy Willow." her wife smiled back.

Her wife, Emily, was the most wonderful woman in the world. She was a professional Mistress and easily spotted her inner sissy desires. Emily helped bring Willow out of her fantasies and into reality, training her to not just be an obedient sissy, but one that was open-minded and sharing.

Not to mention bisexual.

They were both the same age, 28, and got married three years ago. Their female-led relationship had centered around Emily being Mistress and Willow being her sissy-self part-time. Not to mention the hotwife/cuckold subculture of FLR. When Willow reverted to being a man, he was still submissive to his wife, but not at all interested serving other men. When Willow took over, though, she was such an insatiable cock slut.

"Sleep well last night?" Willow asked.

Emily smiled and stretched her back with her arms above her head, pushing out her firm b-cup breasts. "Mmm...yes I did..." Going back to applying her smokey black eyeshadow to compliment her dark eyes, she added, "Frank will be back later tonight." she paused to smirk at Willow in the mirror. "So, I'll be needing more cleanup duty from you."

"I love to serve you, Mistress." Willow smiled back.

"And that's why you're the perfect little sissy wife for me." she replied, pausing to give her a little kiss on the lips. "You better get going, sissy; you don't want to be late for work."

"Yes, Mistress. I hope you have a good day at work too."

"I usually do." Emily smiled.

Willow exited the master bedroom and went downstairs to grab her breakfast and lunch, both pre-packed in a lunch bag along with her day's work schedule, and then went into the attached garage. Starting up her car, she opened the garage door with the remote and drove away, closing the door behind her. The first address was in a subdivision not unlike the one she lived in, but it was nearly fifteen miles away.

Her job, as chosen by her Mistress wife, was that of a sissy maid for 'Maid in Heaven, Inc.' It was a small-time business where sissies went to client's houses as maids to do housework that single men didn't want to do or didn't have time for. Her services included vacuuming, window and dish washing, laundry, and dusting. Not to mention the normal services a sissy performed for men. Prostitution was illegal, but a weekly house maid was not. Like with escorts, whatever happened between customer and client after the work was done, was 'completely separate' from the money transaction.

Maid in Heaven was a subsidiary of The Matriarchy, which was where Emily worked as a professional Mistress and dominatrix. All Maid in Heaven sissies are trained and 'owned' by Matriarchy Mistresses, that's how Willow got the job.

About twenty minutes later, she arrived at her first client's house and exited her car with a tote full of her cleaning gear (gloves, brushes, duster, etc...), an anal douche kit, and a travel makeup kit, and then knocked on the front door.

A middle-aged man with a short beard or long five-o-clock shadow wearing a bathrobe answered the door and smiled. "I've looked forward to seeing you again."

She smiled and curtsied. "Sissy Willow is happy to serve, Sir. May I enter?"

He nodded and stepped aside. Willow entered and set her bag down on the floor, knowing that this particular client preferred to start out with a good cock sucking. After he closed the door, he sat in his recliner and opened his robe, revealing his slightly hairy body and a quickly growing six-inch dick. Willow went over and knelt between his legs, smiling up at him.

"Thank you, Sir, for the privilege of serving you as your sissy maid." she said, then lowered her head and took his member into mouth. Her lips sealed around his shaft just after the blunt tip and her tongue began swirling around, tasting his precum and teasing him. The man moaned and put his hand behind her head, but didn't shove himself down her throat quite yet. He wanted to savor his first orgasm from the sissy's maid service.

The blunt tip of his organ repeatedly pushed against the back of her throat as her head slowly bobbed up and down, but she didn't gag. Willow's Mistress trained her too well with her strapon for that. She kept her throat closed to continue teasing the most sensitive part of his cock until the time was right to slide her lips down to his balls. The man moaned his appreciation from deep within his chest and pulled her tighter into his groin, holding her there. Sissy Willow looked up at him with her innocent-looking eyes, giving him no resistance, and received a sinful smile in return.

When he released her, she stayed put like a good girl for a few more moments, and then resumed bobbing her head. She never looked away, even as his member entered her throat on every down motion and caused her eyes to water. She batted her long, pretty eyelashes at the man as a means to clear away the tears before they fully formed and ruined her makeup, and he loved the sight.

So much so that he grabbed on either side of her head once again and took control.

He moved her along his cock like her face was his personal masturbator. He was slow at first, but he quickly increased the pace after the first few tears formed and made streaks of mascara run down her cheeks. The 'glucking' noises she intentionally made for his pleasure was music to his ears and encouraged him to use her as he saw fit.

And he did.

Her mouth stayed on his dick while he took off his robe and stood, positioning himself to fuck her face to his heart's content. Willow remained submissive and compliant, looking up at the dominant man as she served him like a sissy should. She reached out and grabbed the backs of his thighs, caressing and clawing in response to his raw sexuality, throating his member as he eagerly thrusted. Tears freely flowed down her face, ruining her makeup with multiple streaks of mascara and she loved it.

Because that's exactly where a sissy should be and that's exactly how a sissy should be treated by a dominant man.

His breathing soon became shallower and more erratic, letting Willow know that she was about to be given a delicious treat. He humped her face a few more times and then buried himself down her throat, letting his orgasm explode outward and his sperm ejaculate straight into her stomach. She was a little disappointed at not being able to taste him, but his grunts and moans were reward enough for her sexual services.

Once he was spent, he slowly pulled out from her lips as they remined sealed around his deflating organ, sucking every last drop of fluid from him. With his member free, he playfully slapped it against her face and lips.

"You always give better head than my girlfriend." he smiled.

"Thank you for letting me serve you, Sir. It's always a pleasure." Willow smiled back.

He pet her on the head and then grabbed his robe, heading for the upstairs shower. With her makeup in ruins, she grabbed her tote of cleaning supplies and began with his downstairs bathroom. She cleaned his house once a week, so things stayed pretty clean and her visits were usually only two hours long, depending on how much stamina he had. Each of her clients received two orgasms as part of her sissy maid services, one before she cleaned their home and once more after. That was reason enough to hurry through the cleaning portion of the job, but she prided herself on quality of her maid's service as well, so she did her best to take her time and be thorough.

It would also give her client more time to recover for a second round of sex.

Meanwhile, her Hotwife and Mistress Emily was in her lair, waiting for her own first client of the day. She was wearing black thigh high fishnets with black, four-inch heeled latex boots that went up just above her knees, a black latex overbust corset, and elbow-length latex gloves. Her makeup was immaculate with dark eyeshadow, eyeliner, and mascara, ruby red lipstick, and a hint of rouge. Her dark brown hair was tied in an offset braid down her left side and hanging down the front of her shoulder.

Her first client was a regular and was some kind of businessman. He was used to taking charge and making all the decisions in his daily work life, but he needed a break every week to let someone else take control. Emily looked at the clock that hung on the wall above the black toolbox that contained the implements of her trade and saw that he had only one minute to arrive. If he was late, she'd punish him, but he suddenly opened the door and entered, wearing only a bathrobe and his play collar.

He took off the robe and hung it on the hook next to the door before kneeling before his Mistress. "Good morning, Mistress." he said, his hands resting on his knees and his head slightly bowed.

"Good morning, slave." she replied. "For a moment, I thought I was going to have to punish you for being late."

"I had a phone call from work that..." he began, stopping abruptly when she raised her hand.

"I don't want to hear excuses. You're here to serve me and my sadistic pleasures, nothing more."

"Yes, Mistress."

Emily went to her toolbox and opened a drawer. She examined the various floggers, whips, canes, and paddles, and chose the four-foot-long leather whip. Taking it from the drawer, she approached her slave and wrapped it once around his neck. Lifting his gaze upward to meet hers, he gently kissed her clit. Emily loved having every client start off the session that way; it was a sign of their deference and submission to her female authority.

Unless she made them go pussy-free, that is.

She then wordlessly used the whip as a leash and led him to a metal stockade with padded leather at floor level. Her slave knelt on the leather, resting his wrists and head in the three half circle slots, allowing her to close the top half and secure him with a loud click from a padlock. He was slightly bent forward so his ass was presented for her torment and his mouth was at a decent level with her crotch.

All slaves should worship their Mistress with their tongues as thanks for their whippings, after all.

Her heels clacked along the hardwood floor as she stepped back to the perfect distance for the whip she'd chosen. She gazed upon the man's naked rear, lowering it to study his vulnerable balls. She smiled to herself as she remembered the new toy she'd gotten for her stockade, and then went to the toolbox to retrieve it.

Returning to her slave, she knelt down behind him. "I have something new I want to try out on you, slave."

"I'm happy to serve you, Mistress." he replied.

"Yes, you are." she simply replied, attaching the ball parachute to his scrotum and then tying it to the small metal loop on the frame of the padded leather.

She adjusted the length of rope to give him some room to move forward, but not much. Standing up, she went to get her whip from the toolbox's benchtop and returned to stand behind her slave. She flicked her wrist to give him a gentle strike on his left cheek and he jerked forward, the parachute preventing his balls from going passed a certain point and making him groan in slight pain.

"Mmm, I'm going to like using this." Emily smiled, flicking her whip at his right cheek.

Flinching forward again, his balls stayed put and he groaned. Emily smiled. She didn't have to whip him very hard to make him squirm, but that didn't mean she would go easy on him.

Thwack!

He jumped forward from the harsher strike and then yelped from his stretched scrotum. "Be careful, slave..." Emily smirked. "You don't want to hurt yourself. That's my job..."

Thwack!

Her slave managed to stop himself from jerking forward, but not completely. He groaned in the pleasure of his Mistress using him for her own sadistic desires and his erection oozed out a drop of precum.

"Thank you, Mistress..." he whimpered.

"Aww...you're welcome slave..." she playfully replied just before whipping his lower back.

She continued lashing out with her whip until he had several faint, crimson lines down his back and rear, then she released him from the stockade and removed the ball parachute from his scrotum. Giving him a playful kick between his legs from behind, she told him to turn around and begin worshipping her latex boot encased feet. On his hands and knees, he kissed each boot a few dozen times and polished them to a shine with his tongue.

"You have been very good, my slave." Mistress Emily said.

"I'm glad to have served you to your expectations, Mistress." the man humbly replied.

"Lie on the bench and your Mistress will take care of you."

The man crawled to a padded bench, stood, and then laid face down on top of it. Emily swapped her elbow-length of latex gloves for a piar of disposable ones. Then she grabbed a jar of salve and began applying it to her slave's reddened skin. Once done, she put the salve away and threw away the disposable gloves, grabbing a new pair and a small bottle of silicone-based lube. She then squirted out a drop on each of her right middle and index fingers and applied it to the underside of his flaccid member. As she rubbed his organ, it pressed against the bench and hardened, causing him to moan his gratitude.

"Thank you, Mistress." he said.

"All good slaves should be rewarded." she replied, giving him no more than the short rub of her two fingers.

She made sure to keep him hard but far from the edge of climax. She was not the kind of Mistress that rewards her slaves with an orgasm. She saved such things for the men in her life that she knew and cared about and not clients, who were in a different category. She teased him for about ten minutes, then turned her attention to his balls. She squirted out a few more drops of lube and coated his entire sac.

Wrapping her index and thumb around his testicles, she pulled downward, earning a low graon from the man, and slowly loosened her grip until his sensitive orbs slipped from her grasp. She then wrapped her fingers around him again and repeated the sexual torment several more times before grabbing him with her entire hand and squeezing.

"Thank you, Mistress." he croaked, eyes clenched shut from the welcome pain.

"You're very welcome, my slave." she smiled. "When you get home after our session, what are you going to do?"

"I will record myself...masturbating to your picture..." he panted, "...and then stop just as...I cum...to ruin my orgasm for you..."

"Very good, my slave..." she replied, squeezing down harder on him with one finger after another, kneeding his balls. "And what will you do with your mess?"

"Catch it..." he paused, an almost high-pitched grunt escaping his lips, "...in my hand...and lick it up..."

"And why is that?" Her fingers stopped kneeding and simply clamped down hard.

"Because...your slave's cum...belongs inside him..."

She slowly began releasing her grip and said, "That's right, my slave. You only deserve a ruined orgasm and your cum must go back inside you because that's where it belongs." She let him go entirely and went back to her toolbox to throw away the disposable gloves.

"Yes, Mistress..." he panted, relieved.

Turning back to him, Emily said, "You may go now, slave."