Copyright 2014 Christopher D.B.

This story is written by Christopher D.B, please send comments and appreciation to christopherdb113@gmail.com

The Baroness would be home soon. She was a realtor so her working hours changed day by day. I’d taken to eavesdropping on her phone conversations and checking her agency’s web site for her open house schedules in order to have a rough idea of when she might return.

Starting with the second floor of the townhouse condominium, I double checked the bedrooms and bathrooms. The walk-in closet off the Baroness’s bedroom had a large three panel full length mirror, like something you might find at a clothing store, and I paused in front of it to inspect my uniform.

I wore a French maid style uniform, black satin with white lace trim and matching apron. It had short puffy sleeves and the hemline was halfway up above my knees. A white ruffled petticoat underneath filled out the bottom of the dress. That, combined with a properly fitted bra and silicone breast forms, transformed my male body into the shape of a female.

My hair was shoulder length and had natural body so I was not required to wear a wig. Some lipstick and light makeup completed the illusion, though I would never consider myself to be pretty. My facial features were too masculine, and this late in the afternoon there was the slightest bit of beard stubble growing in on my chin.

It didn’t matter that I wouldn’t pass for a woman in public. The look was good enough to be a sissy maid for Baroness Maria, who was a lifestyle dominatrix. She didn’t perform sessions for hire, but maintained a stable of male slaves to serve her various needs.

One of my black stockings had a run at the knee. I had learned to buy cheap ones, because such damage was inevitable when doing housework. However, if the Baroness were to spot that when she got home, I’d likely receive a flogging.

After making a careful check of the first floor, especially the kitchen, I went down to the maid’s quarters in the basement.

While the Baroness called it the maid’s quarters, it was really just a small partitioned off section of an otherwise unfinished basement. There wasn’t even a door, just a few roughed in walls painted pink, like a little girl’s princess bedroom. The space was furnished with a white metal framed daybed, covered in pink satin sheets with white satin throw pillows, and a small white dressing table with a matching stool and mirror. One wall of the maid’s quarters was made of four white wardrobe cabinets, one of which was mine.

Opening my wardrobe, I took out a new stocking. Hiking up my dress, I unclipped my garter straps, then sat down on the edge of the bed and kicked off my shoes. They were black patent leather, with thick heels about two and a half inches high. I could actually walk well in four inch stilettos, but I’d learned not to wear shoes like that when working as a sissy maid. They just weren’t a good choice for walking on freshly mopped floors or going up and down stairs all day.

Once I had replaced my stocking, I checked myself in the full length mirror mounted on one of the wardrobe cabinets. At last I was ready for the Baroness to come home. Glancing at the small clock radio by the bed, she could arrive at any time. I decided to just sit on the bed and wait.

Staring across the small room at the line of wardrobe cabinets, I always wondered if all of them were in use. Did Baroness Maria have four sissy maids in her stable? The cabinets were locked, so there was no way to tell. Of course I had tried my key on the other cabinets out of curiosity, but it wouldn’t open them.

I felt like I was going to doze off, which was actually permitted so long as my list of chores was done, when I heard a metallic rattling upstairs of the garage door opening. The Baroness was home.

Making it upstairs as fast as I could, I opened the door to let her in. Baroness Maria thrust her purse and laptop computer bag into my hands, and passed by me without saying a word. I placed those items on the kitchen table, and then dropped to my hands and knees in front of her. The Baroness placed one foot forward, tilted back in its high heeled shoe, and I got down lower to give her shoe a once over with my tongue.

The shoes were pumps made of leather in a dark burgundy, with the toes coming to a gentle point. The heels were about three and a half inches tall. High enough to be sexy, without looking slutty and unprofessional. They were an older pair and she kept all her shoes looking clean by having me lick them every time she left the house or returned.

She pulled her foot away quickly and presented me with the other shoe to clean. Baroness Maria was well aware of my fetish for high heeled shoes and enjoyed teasing me, making me perform this maintenance task but not allowing me to savor the smooth warm leather on my tongue.

After licking her other shoe clean, I stood and lifted my dress. She pulled at the waistband of my panties and inspected my chastity device to see that it was securely locked and hadn’t been tampered with. I was required to wear it to prevent me from masturbating while she was away.

As was our usual routine, I then went to stand in one corner of the kitchen, nose to the wall, with my hands behind my back, while she checked my work. Baroness Maria’s high heels clicked on the floor tiles as she made a painfully thorough inspection of the kitchen. Then she moved on to the rest of the house.

There was a long checklist of chores that I was required to do. It was posted on a door of one of the wardrobe cabinets down in the maid’s quarters. I’d practically memorized it by now, and while the list was long, if approached methodically it was possible to complete well and on time.

The Baroness returned to the kitchen, pulled one chair back from the table, and told me to take my position. As I moved into place, standing behind the chair, bending over its back and grasping onto the edge of the seat, I saw the paddle in her hand.

It was made of a dark colored wood, and cut in the shape of a large old fashioned hair brush. She lifted my dress to expose my backside, and pulled my panties down to my knees.

The swats echoed loudly in the kitchen, landing firmly on my buttocks. Her technique with the small paddle was always the same. Firm swats at a brisk pace, alternating from one cheek of my ass to the other. The real variable was how long the paddling would last.

I didn’t cry out, and though I squinted at the pain, no tears came to my eyes that might cause my makeup to smear. At last she stopped and said,

“Well done.”

Baroness knew that I liked to be spanked, so that firm spanking with the small paddle had actually been my reward, and the only thanks I would receive. Had I made any serious mistakes, she would have used a heavier paddle, or worse, her cane. At this point I might have been released to go home, but Baroness Maria told me,

“One of my sex slaves will be arriving shortly, so you will have to stay a while longer. Now come upstairs and help me get ready.”

In her bedroom, she callously stripped of her clothing and threw it on the floor, leaving the items for me to pick up. Baroness Maria stood just over five feet tall in her bare feet, and had a long mane of dark curls that spilled over her pale shoulders and halfway down her back.

Her beautiful breasts were thirty six double D’s. I knew the exact size since I was required to hand wash her bras. Her hips and ass were well rounded, and though her body had some extra pounds, she carried herself with a confidence greater than any super model.

As she sorted though her lingerie drawer I turned down the silver and deep blue satin comforter, revealing matching sheets underneath. By that time she had pulled on a cami top of purple satin with black lace trim, and handed me a matching garter belt to hook together at the back of her waist.

Baroness insisted on pulling her own stockings on, black sheer nylon, but it was my task to clip the garter straps in place, making sure they were properly adjusted. I handed her the final piece, a matching satin and lace trimmed thong backed panty, which she pulled on herself.

I then followed her to the walk-in closet, where there was an impressive collection of shoes and boots. Colors, heel heights, and styles for almost any occasion. She dropped a pair of shoes beside me, and I got on my knees to slip them on her nylon clad feet.

It was a pair of black patent pumps. The sole had a platform that was perhaps an inch thick, while the thin stiletto heels were about six inches high. I always thought of them as her fuck-me pumps, as they seemed to be a favorite pair of hers for times when sex slaves came over to serve her.

It was an extra thrill to give the smooth patent leather a quick cleaning with my tongue, knowing she had been fucked while wearing these shoes on a number of occasions. Like a porno queen she almost always kept her high heels on during sex, and I thought that was incredibly hot.

“Christine, fetch me some wine,” Baroness Maria ordered. As her sissy maid, she always addressed me with the feminine version of my name. I hurried down the stairs to the kitchen.

There were always a few bottles of a modest priced White Zinfandel in the fridge. I removed the cork, set the bottle in a bucket of ice, and then selected a single wine glass from a cabinet. The wine was only for the Baroness.

Although the sex slave who was on his way would have the illusion of a romantic encounter in her satin bed, with the Baroness all dolled up, it was his job to please her and nothing more.

I had just returned to her bedroom and was pouring a glass of wine for Baroness Maria as she primped her hair in front of her bathroom mirror when the doorbell rang.

“Let my sex slave in,” she ordered.

Before opening the door, I looked out the peephole. I recognized the tall blonde man. I think his name was Carl, and he had served the Baroness on a few recent occasions. Perhaps he was her new favorite toy.

“Is the Baroness in a good mood?” he whispered to me as I let him through the door.

When serving Baroness Maria, I wasn’t allowed to speak to anyone, let alone one of her slaves. I knew the same rules applied to him, yet the few brief times we had been alone like this he always tried to make some quick conversation. As usual I said nothing, and just started walking upstairs.

The Baroness was reclining seductively on her bed when we entered the room. I made my way to a low stool in one corner, and I sat down to wait for any more orders.

“Strip for me, slave,” the Baroness commanded, and then took a sip from her wine glass.

Carl was wearing a shirt in some blue color, which looked as if it might be part of work uniform. He made a slow show of unbuttoning it and posing for the Baroness. Dropping his shirt to the floor, he slowly flexed his muscles, trying to pose provocatively for her. He wasn’t a body builder by any means, but probably hit the gym a few times a week, which was more than I ever did.

Like all of her sex slaves, he was clean shaven, and had no tattoos or body piercings. Of course he had another required feature, which was very obvious as soon as he dropped his khaki pants. Though he still wore some boxer shorts, I could tell that he was getting aroused at the sight of Baroness Maria.

She had explained to me one time that she wasn’t interested in finding just any man with a big cock. She wanted one that she felt was a good fit. About eight inches long and a bit thicker than average was her preference.

Baroness had pointed out months ago when I started my sissy maid training, that I simply didn’t measure up as a man and would never be able to become one of her sex slaves. Although she had some uses for me in her bedroom, I think I was allowed to watch her with her sex slaves in order to humiliate me, reminding me of my slim five inch erection.

Carl was ordered to join the Baroness on her bed. He began to kiss her passionately, first on the lips, and then moving down to her neck. He slowly caressed her body, keeping his hands above her waist for now and off of her breasts.

When it came to sex, Baroness Maria was never in a hurry. Sex slaves had to take their time to slowly build her arousal. She took another sip of wine, emptying her glass. A quick glance at me was the only cue I needed, so I got up to refill her glass.

“Christine, get me nice and wet for this big cock,” Baroness said, slipping out of her thong and spreading her legs.

I knelt beside the bed and she hooked one nylon sheathed leg over my shoulder. Her dark patch of pubic hair was always nicely trimmed, though I never had the pleasure of doing that task.

Whenever Baroness Maria ordered me to go down on her, it was my task to only get her wet, and not try to pleasure her, as that was a job for her sex slave. I always found it to be humiliating, being ordered to lick her pussy while she made out with a well hung stud. She would never know that the loss was hers, as previous girlfriends and even my ex-wife, had always been thrilled with my oral skills.

Carl was ordered to remove his boxer shorts and then the Baroness shifted her position so she could suck his cock while still being serviced by me. She never gave a real blowjob and would certainly never allow a slave to cum in her mouth. This was the final stage of her foreplay where she would suck and lick his cock just enough to get it completely hard and slick to enter her.

However, this time something was different. She was taking more time than usual and judging from the motion of her body and noises I heard, it sounded like she was stroking his cock quite a bit.

At last she sat up on the bed and pushed me away.

“I’ll give you one minute to get hard, and not one second more,” she scolded her sex slave.

The straps of her cami top had been pushed off her shoulders, allowing it to drop and expose her fantastic set of tits. I looked over at Carl lying on the bed, his erection only at half mast. He gripped his penis firmly and stroked it franticly.

Baroness Maria kept looking back and forth between the clock on her nightstand and her sex slave’s cock, which didn’t seem to be getting any harder despite his best efforts. Who knows what his problem might be? Performance anxiety? I wouldn’t be surprised.

“That’s enough,” the Baroness told him. “Now stand in that corner. Christine, take your seat.” I scurried off to my stool while a worried Carl walked slowly to the corner. Baroness produced a set of handcuffs and secured his hands behind his back. She then straightened her cami top and pulled on her thong.

Picking up her glass of wine and cell phone, she closed herself in her bathroom. Before long I could hear one side of her muffled phone conversation, but couldn’t make out any of it.

“What’s gonna happen?” Carl whispered to me from across the room. There was a real sound of fear in his voice. I didn’t answer him. For one thing, I wasn’t going to speak to him since it was against the rules, and also I had no idea. I had never seen a sex slave fail to get an erection before.

At last the Baroness came out of her bathroom. I avoided eye contact. She took a cane out of a dresser drawer and ordered Carl to kneel before her.

He walked clumsily on his knees, hands still cuffed behind him, begging for mercy the whole time. Maybe half an hour ago he had strutted into her bedroom as a stallion, but now he was a groveling weasel.

She slapped him across the face and told him to shut up.

“Your days as a sex slave are over,” she told him. “I have another sex slave on the way and I’m going to cane you until he arrives.” She swished her cane menacingly several times, the slim bamboo rod hissing as it cut through the air. “Consider yourself lucky that he doesn’t live far away.”

Carl was then ordered to stand up and bend over. He was whimpering with fear. Perhaps he had been caned by her before. While I enjoyed a firm paddling, caning was a real punishment. A searing and burning pain that felt as if it cut deep.

As her cane sliced through the air and left red stripes on his ass, I was glad it wasn’t me receiving the punishment, but hearing his muffled cries of pain was rough. She paced herself, giving him several strokes of the cane and then berating him.

“Your limp dick is worthless to me,” she said. “Sex slaves get no second chances.”

Baroness Maria’s cane sliced through the air several more times, cracking loudly on his ass.

“When my sex slave gets here you’ll see what a proper erection looks like. I’m even going to let you watch me get fucked. In the unlikely event that you get hard,” she sneered. “You don’t have my permission to jerk off.”

She began to cane him again, when mercifully for him, the doorbell rang. I was ordered to go downstairs to let her sex slave in.

Looking out the peephole, I was a little surprised at what I saw. He was clean cut and well dressed, Baroness Maria’s normal type, but he was a black man and I had never known her to cross racial boundaries before.

“I’m here to see Baroness Maria,” was all he said, when I opened the door. Some sex slaves try to stifle a laugh when they see me in my frilly maid’s uniform, but this guy was cool just stood outside for a few moments until I waved him in through the door.

When we got upstairs, the Baroness was sitting on the edge of her bed mumbling some final demeaning words to Carl, who was still in handcuffs and kneeling beside the bed.

“Christine, fill my glass,” she ordered. As I pulled the bottle from the ice bucket she said to the black man, “Taylor, drop your pants and get hard. I’ve already wasted my time with this slave,” she pointed to Carl who was just looking down at the floor. “I won’t waste any more of my time so you need to get it up now.”

The tone of her voice was stern but Taylor calmly lowered his trousers and boxers to his knees and slowly started stroking his cock. He began to get hard almost immediately.

While her other sex slaves that I’d seen all had similar sized cocks, it was obvious to me as his erection started to grow, that Taylor was better hung than any of them. Within a very short time he stood calmly with his hands at his sides awaiting his next orders, his erection standing at least ten inches tall and extra thick.

“That’s how it’s done,” Baroness Maria said to Carl, and then ordered Taylor to sit on the foot of her bed. She knelt beside him on the bed and bent over in preparation to suck his big piece of dark meat. Wiggling her ass in Carl’s face, she said.

“Now lick me and get me nice and wet. Don’t try to pleasure me since you’ve already failed me today.”

Baroness Maria started giving Taylor’s cock long slow licks, while a dejected Carl inched up closer to the edge of the bed and began to lick her pussy. As soon as Taylor’s cock was glistening with her saliva, she took it into her mouth and began to suck him slowly and seductively.

From my stool I had a perfect view of the threesome and my penis was straining uncomfortably as it tried to get hard inside the plastic confines of my chastity device. Normally when the Baroness was with her sex slaves I looked away and tried to put my mind on other things to avoid this from happening, but this time I couldn’t look away.

I felt Baroness Maria was trying to tease me, occasionally pushing her long dark hair back so I could get a better view of her lips wrapped tightly around that thick black cock. It seemed she could only take less than half of it into her mouth. Taylor gently caressed her hair and shoulders, and began to breathe deeply, clearly enjoying himself.

Once Baroness Maria’s saliva had dripped all the way down to the base of his cock, she told Taylor to lie back on her bed. Callously placing one spike heeled foot on Carl’s chest, she pushed him away from the edge of the bed. His work was done for now but it seemed he would be allowed to watch.

Baroness Maria straddled Taylor, firmly grabbed his thick erection, and inserted the tip into her moist pussy. With great care she slowly lowered herself and a let out few gasps that might have been a combination of pain and pleasure.

Her pale curvy ass and hips were beautifully framed by her garter belt as it looked like she was slowly impaling herself on that huge black cock. Baroness Maria only took about half of it in before pulling out a bit. Apparently finding a comfortable depth for herself, she began to slowly ride her sex slave.

Normally the Baroness would begin to fondle herself, gently rubbing her clit until she had an orgasm, and it would be her sex slave’s responsibility not to cum until that happened. However, this time the Baroness kept her hands planted on her slave’s muscular chest. Taking his thick penis a little deeper each time seemed to be all the stimulation she needed.

By the time she had taken him all the way in, my penis was painfully cramped inside my chastity device. Baroness Maria sat there on top of her sex slave, his massive erection filling her completely, and slowly began to gyrate her hips. Her breath came in short gasps as she moaned deeply.

Then she began to ride his cock at a moderate pace, nearly pulling out and then sliding all the way in each time. Her pussy now stretched to accommodate that massive black penis, Baroness Maria was wet with arousal, her juices gleaming on his cock.

“It’s a little late for that,” The Baroness suddenly laughed at Carl, who was still kneeling beside the bed. I looked and saw that he was hard. With hands cuffed behind his back, he might as well have been in chastity like me.

While I expected Baroness Maria to ride that big black cock until she climaxed, she dismounted her sex slave, mumbling some instructions to him that I couldn’t hear.

Baroness Maria lay on her back and spread her legs widely. I caught only a quick glimpse of her wet gaping pussy before Taylor blocked my view. He entered her slowly. She tilted her pelvis and raised her knees up high in order to take him all the way in.

With her black patent stiletto heels pointing at the ceiling, Taylor began to fuck her, slowly and passionately, with long purposeful thrusts.

The Baroness began to make deep stifled gasps as her sex slave quickened his pace. I knew that sound and she was just moments away from a powerful orgasm. She ordered her slave to fuck her harder.

Taylor obeyed, violently slamming his cock into her balls deep, pushing her ass down into the satin sheets with each stroke. His dark skin was glistening with sweat and her nylon sheathed legs trembled as Baroness Maria let out a series of orgasmic moans.

She continued heavily panting as her sex slave continued to heavily thrust himself into her, repeatedly pounding her ass into the bed. I was certain that my balls were blue, yoked at the base by my chastity device, and my penis was compressed painfully inside.

Then her sex slave gave several deep grunts and slowed his pace as he came. Baroness Maria lowered her legs, stiletto heels planted in the satin sheets as Taylor’s violent fucking slowed like a freight train easing to a stop.

“Well done,” she said, faint of breath, and Taylor pulled out his dripping half hard cock. At this time I would normally be asked to hand her a small towel so she could clean herself, but this time she had other plans.

Baroness Maria got up and sat on the edge of the bed, legs spread wide in front of Carl’s face. She grabbed him roughly by his short hair, and pulled him towards her dripping pussy.

“Clean me up, slave” she ordered. “Don’t try to give me an orgasm, just lick up his cum.” Suddenly she turned to me.

“Christine, show my sex slave to the door.” Taylor took his cue, got off the bed and quickly began putting on his clothes. I only had a minute or so to watch a humiliated Carl lapping up another man’s cum. A punishment I suppose that was fit for a failed sex slave.

I escorted Taylor to the door, knowing I would probably see him again, yet unsure that the Baroness could take a beast fucking like that except on rare occasions. A truly obedient slave, he departed without saying a word.

When I made it back upstairs, I was ordered to pour the last of the wine into Baroness Maria’s glass. Carl was still busy cleaning her pussy and it was obvious that he was not enjoying the task.

On very rare occasions, the Baroness had allowed me to masturbate and cum on her high heeled shoes or boots. It had been an honor and a privilege, but with that came the responsibility of cleaning up my mess. To Baroness Maria that meant I had to lick my own cum off her shoes. While I didn’t care for the taste and the slimy texture, at least it was my own cum. The thought of licking the Baroness’s freshly fucked pussy while globs of another man’s cum oozed out into my mouth was disgusting, and she was making sure that Carl lapped up every drop.

At last she pushed him away and commanded me to hand her a robe. I selected a long black satin robe from her closet and placed it on her shoulders. She stepped out of her black platform pumps and picked up articles of Carl’s clothing and began tossing them out the bedroom door and down the stairway.

“Now march your sorry ass downstairs,” she said to Carl. “Christine, freshen up my bedroom and then you may be dismissed.”

Carl, his chin wet with her juices and Taylor’s cum, carefully stood up with his hands still cuffed behind his back. The two of them went downstairs.

I picked her shoes up off the floor. The black patent leather was still warm from her feet, and I held them one at a time over my nose to deeply inhale the aroma of her sweat. Not just any foot sweat, but smell of her feet that had been in these sexy shoes while getting what may have been the hardest fuck of her life. The scent was intoxicating and I could feel my aching cock try once again in vain to get hard inside my chastity device. Despite the discomfort, and even though I hadn’t been ordered to do so, I slowly and lovingly licked her pumps before setting them in their place on a shelf Baroness Maria’s closet.

The satin sheets were in disarray on the bed, and the matching comforter had slid off into a shiny pile on the floor. There were two distinct wet spots on the sheets. One where the Baroness’s juices had dripped from her pussy, and down across her asshole while she was fucked. I couldn’t resist burying my nose in that damp patch, deeply taking in the scent of her musky arousal.

The second wet spot was smaller and at one edge of the bed, where she had forced Carl to lick her clean. He was downstairs now where the Baroness was giving him a vicious scolding. I realized I had been wasting time for my own pleasure. Knowing she would not tolerate that, I quickly stripped the sheets off the bed and remade it.

The new sheets were also of satin, but in a deep burgundy, with a matching comforter. I had to make the bed quickly because of lost time, but was able to do a neat job that would pass any of her regular inspections.

When I walked down the stairs and into the living room, Carl was on his knees before the Baroness. He was begging and pleading for her to give him another chance as her sex slave.

As I made my way down to the maid’s quarters I thought he was an idiot. I couldn’t imagine returning with such pressure to get an erection and satisfy her, now knowing what sort of humiliating punishment waited if I failed.

After removing my makeup and changing into my normal clothes, I packed my uniform and girly underwear into the laundry bag on the floor of my wardrobe cabinet. It was getting full so I would take that home. I was not allowed to wash my own clothes on Baroness Maria’s time.

Back in the living room, the Baroness seemed to be in a pleasant mood. I’d overheard Carl leaving a few minutes ago. Without a word she handed me the small key to my chastity device.

With great relief I opened my pants and removed the contraption, dropping it in my laundry bag. Despite being flaccid, my penis ached from being confined while highly aroused. I might have to soak in a hot bath for a while when I got home, but I was dying to masturbate.

Remembering Taylor giving Baroness Maria the fucking of her life with his huge black cock while Carl watched helplessly, I knew I would have an orgasm powerful enough to rival any sex slave.