The Cucksitter Ch. 01

My knees ached as they supported my shivering naked form on the cold hardwood floor. I looked up lovingly at my beautiful wife, Sarah, as she stood over me with a mischievous smirk on her lips. She lowered herself, her straight brown hair bouncing on her pale shoulders as she approached my level. Without a word, she grabbed my small flaccid cock and stuffed it into a tiny pink chastity cage. The lock turned with a click, and Sarah stood back up.

"You're to be on your best behavior tonight," Sarah spoke, condescension in her voice. "Don't embarrass me."

I nodded. "Yes ma'am," I replied. "I'll do my best."

Sarah smiled. "You'd better."

Moments later, the doorbell rang. Sarah turned and walked down the hall and into the foyer. Her tight black dress clung to her thin muscular form as her high heels clicked with each step. I couldn't believe how incredible she looked tonight. A pang of jealousy rose from my stomach to my chest as I thought about the fact that another man, and not me, would be appreciating Sarah's incredible beauty tonight.

Sarah pulled open the door and a frumpy woman in her early fifties entered, but not before administering a quick bow. This woman wore a long black skirt with flat black shoes. Her chubby upper body was mostly obscured by a black peacoat, and her greying hair was neatly bound in a bun behind her head.

"I'm glad you could make it on such short notice, Miss Cheston," Sarah said. "Last minute dates can be difficult to arrange a cuck sitter for."

Miss Cheston nodded knowingly. "Of course dear," she replied. "It's my duty to make sure cuckold husbands don't stray. It often involves last-minute calls, so nothing to worry about."

Sarah smiled and nodded as Miss Chestion removed her coat. Beneath it was a simple black blouse. Her stomach protruded above her skirt and hung a bit low, likely due to years of being overweight. Her large breasts hung similarly, giving the woman an almost motherly look.

Before long, Miss Chestion approached me.

"I assume this is the cuckold that will be under my charge this evening?" she asked.

Sarah nodded. "Yes, this is my house husband, Dan," she replied. "He's a bit rough around the edges, but he generally does as he's told."

Miss Cheston scowled. "Rough around the edges? I'll see what I can do about that. I trust you signed the agreement in full?"

I blushed, embarrassed by the fact that these two women were talking about me as if I wasn't even in the room. Truly humiliating.

Sarah nodded. "Yes, you have full legal rights to do anything you need to train and supervise my property. I am quite confident in your abilities, and permit you to do literally whatever you think is necessary, no matter what."

Miss Cheston nodded. "Very good," she replied. "I've been in this business for decades. Some say I have a heavy hand, but I've found it's necessary when dealing with cuckolds who are 'rough around the edges', as you so elegantly put it."

Sarah laughed. "Whatever you need to do, please do," she replied. "I look forward to the results."

The two women turned to me, as Miss Cheston began to inspect me. Her aged and experienced hands moved down my chest and stomach towards my caged cock.

"Very good, I'm familiar with this device," Miss Cheston mused. "Impervious to escape, and quite uncomfortable during any unwanted erections."

Sarah nodded. "I had some issues with misbehavior in the past, and this helped quite a bit," she replied. "Now, if you'll excuse me Miss Cheston, I need to be off. I'll be back around 3 am, or perhaps later depending on how things go."

Sarah turned to me. "Be on your best behavior for the cuck sitter, or you'll regret it," she commanded. "Miss Cheston is infamous for her creative and terrifying punishments."

The blood drained from my face, but I tried to hide my fear by just nodding silently. Before long, my incredible wife was out the door. I couldn't believe I had let any of this happen, but what could I do?

Miss Cheston stood over me as I ruminated, her chubby arms crossed just beneath her breasts.

"You'll address me as Madame," she ordered. "Any breach in protocol will result in immediate punishment. Do you understand?"

I nodded meekly. "Yes Madame, I understand."

Miss Cheston nodded. "Good, now let's get to work," she replied. "Sarah told me you're expected to wash the dishes, so we'll begin there."

I moved to stand up, but a heavy hand quickly stopped my ascent. "Just what do you think you're doing?" Miss Cheston asked.

"I-I was going to go to the kitchen..." I began to reply before a painful sting erupted across my cheek. Miss Cheston had slapped me!

"You do not make excuses for your misbehavior, cuckold," she replied. "Your place is on your knees. You do not rise without permission. Now, let's try that again. Go to the kitchen."

I grimaced, my right cheek throbbing and stinging with pain as I began to crawl my way down the hall and into the kitchen. Miss Cheston remained always a step ahead of me, walking with a degree of poise reserved for British royal dramas.

Before long, we were at the sink. I looked up, but dared not stand.

"You may rise, cuckold," Miss Cheston commanded. "Wash the dishes."

I quickly scrambled to my feet and grabbed a dish from the sink. I then opened the dishwasher before Miss Cheston grabbed my wrist.

"Cuckolds are essentially house slaves," Miss Cheston spoke, an educational tone in her voice. "They do not deserve access to modern conveniences. You'll be washing these dishes by hand from now on."

I opened my mouth to protest, but the sting lingering on my cheek reminded me of the consequences of that. I returned the dish to the sink and turned on the water before beginning to scrub.

"That's better, cuckold," Miss Cheston replied. "However, I saw that look of defiance briefly flash in your eyes. That's not acceptable behavior for one of your station."

Miss Cheston pulled a black leather crop from her nearby bag. She tested the weight in her hands briefly before taking a swift swing at my left ass cheek. I cried out in pain as the crop hit with a loud crack. Lightning shot up and down my body following the impact, and I nearly dropped the dish I was scrubbing into the sink. A rapid hit from the crop followed again, this time on my right cheek. I bit my lip to avoid crying out again.

I did my best to keep scrubbing and moved on to another dish as Miss Cheston continued her assault. Each hit with the crop hurt more than the last as my cheeks became sore and inflamed. It seemed like she was hitting harder and faster each time too. Before long, it was just too much.

"Please, Miss Cheston..." I choked out between hits from the crop.

"Please, who?" Miss Cheston replied. "You don't use my name, cuckold."

She grunted as she hit my ass with such extreme force that I cried out.

"Please, Madame," I gasped. "I can't take much more. Please..."

Another hit, this time in the same spot as the previous one. My vision began to blur as I nearly dropped the dish in the sink. I quickly finished it and moved on to the pots and pans, rushing to scrub them as the relentless beating continued. Miss Cheston seemed uninterested in stopping.

I grimaced in agony as I moved the last pan to the drying rack. Miss Cheston administered one last disciplinary strike to my sore throbbing behind before stopping.

"I hope you've learned your lesson, cuckold," she spoke, clearly out of breath. "No amount of begging or pleading will stop a punishment. Your wife has been given those same instructions, and this will be a new norm for you."

I nearly collapsed as I leaned over the sink to try to keep my balance. I let out another cry as a swift strike connected with my raw ass once again.

"Why are you still standing up?" Miss Cheston demanded. "A cuckold house slave's place is on its knees. Your task is done, I should not need to tell you to return to your natural place."

I quickly dropped to the floor as tears streamed down my cheeks. This woman was both brutal and relentless. Why had my wife hired such a monster as the cuck sitter? I thought her job was to keep an eye on me, not torment me!

Miss Cheston panted above me. Her blouse and skirt were visibly stained from the sweaty exertion of tormenting me with that blasted riding crop. I wanted nothing more than to rip it from her hands and show her how it felt.

Before long, Miss Cheston caught her breath. She looked down at me, a disappointed frown on her face.

"You have a lot to learn about your place in this world," she said. "It seems like I have a lot of work to do."

She turned and began to rummage through her bag before finding a black metal locking neck collar with an attached chain leash. She unlocked the collar and silently placed it around my neck. I could smell the dripping sweat on her as she leaned forward to bind me. The device locked with a loud click as Miss Cheston returned the key to her bag.

"This device cannot be removed without the key, of which there is only one copy," she explained. "It seems like caging your cock was not enough of a reminder of your place. Perhaps this tight collar will help."

She was not kidding about it being tight. It felt like my breathing was nearly restricted, and moving my neck was no longer easy. The device was surprisingly heavy, and the chain attached to it even more so. The chastity device had almost felt like a fun sex toy in a way, but this truly felt like a slave collar.

"Now on to the matter of your punishment," Miss Cheston continued, a pensive look on her face.

Punishment? Wasn't the beating I just endured punishment enough?

"I can tell you're confused," Miss Cheston spoke. "If you don't handle a punishment with grace and acceptance, you will receive another one. This will continue until your behavior changes. It's the only way to train a delinquent house cuckold like yourself."

My heart sank. How could I have possibly handled that ravaging with grace? I nearly passed out!

Miss Cheston's eyes lit up. "Of course, that one..." she mused to herself.

Without further explanation, she yanked on my chain and pulled me to the floor, laying me flat on my back.

"A cuckold slave is many things," Miss Cheston explained. "But one of the most important roles to play is that of the seat. You must be able to silently serve as a place for your owner, or one of her guests, to rest. Think of yourself like a travel cushion with some extra usefulness."

I looked up at the sweaty woman with confusion in my eyes. What was she even talking about? How could I be a cushion for anyone? Also, was I expected to serve my wife's guests? Thoughts raced through my mind, but I wasn't given long to ponder.

Miss Cheston moved to straddle over me. I could see up her long thin skirt now. Despite her age and her poise, she wasn't wearing underwear. Her fat unshaven ass and pussy were visible above me. I realized now what she had meant by 'seat', but that realization would do me no practical good.

Miss Cheston grunted as she began to lower her fat body. Her knees creaked as her ass approached my face. The stale scent of sweat and unwashed ass began to waft up my nostrils as she descended closer and closer to me. Before long, my nose was parting her cheeks as she lowered herself into a restful position.

Many men fantasize about facesitting, and it's hard to blame them. However, the act is usually done on a soft bed with the woman using her knees to buffer some of the weight. Generally, she's showered first as well and hasn't worked up a massive sweat beating the guy's ass prior.

Being sat on by Miss Cheston was not at all like this fantasy.

As she settled in on my face, she slid her legs out in front of her. The cold kitchen tile did not give an inch as Miss Cheston transferred the full weight of her body onto my face. The massive weight was both suffocating and incredibly painful. My jaw ached and my nose was pressed back by her tailbone. The hair between her ass checks bristled against my face, itching immensely.

Worse than all of this was the smell. Miss Cheston's fat ass trapped sweat incredibly efficiently, and the hairs were caked in it. My eyes teared up in the sweaty prison beneath her cheeks, and my nostrils burned. I let out an involuntary cough, followed by a gag as the smell truly hit me.

Miss Cheston leaned back and let out a sigh of relief. "Cuckolds do make for wonderful seats," she spoke. "Nothing like having a portable ass cushion wherever I go."

We remained like this for quite some time. My whole face ached, and taking each breath was a huge effort. Worse though, I was simply not getting used to the smell. Each time I breathed in, I had to fight the urge to cough and gag. Miss Cheston breathed heavily above me, seemingly catching her breath from earlier. I tried to speak, but found the act incredibly difficult as a result of the weight on my face.

Just as I thought I was going to pass out from the weight of her body, Miss Cheston spoke.

"Why aren't you pleasuring me?" she asked, her voice flat and judgmental. "Cuckolds exist to please their betters. Put that tongue to work."

I couldn't believe it. This painful, foul prison was punishment enough. Now I had to lick her sweat-caked asshole? This was a bridge too far. There was no way Sarah intended for this to happen! I strained my neck to shake my head in protest and managed to choke out a gurgle of defiance.

Miss Cheston scowled above me.

"I had suspected you would be disobedient," she mused. "Very well. We will do this the hard way."

The hard way? This was already horrendous! What could she possibly do to make this worse? Moments later I regretted that thought. Miss Cheston's cheeks clenched, and I could feel her asshole suddenly flex against my nose. A wisp of hot air escaped and quickly expanded into a deafening rippling blast.

I was immediately humiliated and disgusted. The foul air forced its way up my nostrils, overwhelming my senses of taste and smell with the stale sulfuric air of Miss Cheston's bowels. My body summarily rejected this assault. My legs kicked and flailed as I choked on the noxious cloud. The seal between her cheeks and the floor kept the air trapped, there was no escape from this assault.

"It's perfectly normal to fart on a service cuckold like you," Miss Cheston explained, her tone condescending. "Men and women have bodily functions. It's your job to pleasure your betters even if they are bloated or gassy."

Miss Cheston cleared her throat and leaned back. I could hear her gut bubbling above me as I struggled to stay conscious in the foul prison.

"Of course, these bodily functions can also be used to punish disobedience," she continued. "Until you start licking my asshole, the reprimand will continue. Unfortunately it also now tastes far worse, but you can blame yourself for that."

I kicked and tried to cry out, but Miss Cheston weighed far too much. To make matters worse, the toxic fumes were making me feel dizzy and weak. As I tried to focus and stay conscious, another wave of air near-silently hissed from her asshole. This fart was hot and wet, far more foul than the last. I let loose an involuntary gag, which unfortunately simply caused me to suck more of it in.

This assault continued for nearly twenty minutes. The prison between Miss Cheston's cheeks got worse with every passing moment. I was truly surprised at how much my body could take while staying conscious, but part of me wished I would simply faint and end this nightmare. After the tenth fart, I finally broke. Miss Cheston was not messing around, she was going to keep this up all night.

A reluctant tongue parted my lips and inched its way toward the source of my suffering. It poked at Miss Cheston's asshole as she let out a soft sigh.

"That's better, I had feared you would faint before finally learning your lesson," she spoke. "Now slide that tongue in and service me. You'll be doing this for your wife every morning and evening before bed from now on. She's specifically requested it."

Sarah requested this? I felt like I hardly knew her anymore. I let out a sigh as Miss Cheston's moist asshole accepted my tongue. It was both soft and tight and gripped me as I entered. The taste of stale gas quickly hit me as my tongue slid in. I had expected this given how much she was farting, but it was unpleasant nonetheless.

My jaw ached as I began to probe Miss Cheston's asshole. Her juices were worse than the gas. It took all of my concentration and willpower to avoid gagging and retching. I found myself wondering if Sarah also tasted this way, or if she'd somehow be more enjoyable to please. As I pondered this, Miss Cheston began to undulate above me, encouraging my tongue to slide deeper.

Before long, the large woman above me was essentially fucking my face with her asshole. Small bursts of hot gas assaulted my tongue as she used me for pleasure. Her weight felt like it was going to crush me and the tile floor beneath it, but I miraculously held on and remained in one piece. With each thrust of her hips, she began to pant more, and sweat began to drip down her crack and onto my face. One more humiliation to add to the pile.

Miss Cheston's asshole suddenly gripped my tongue as her body began to spasm. She let out a loud moan and nearly flattened me as she dropped all of her weight onto my face again. Her orgasm grew in intensity as her ass thrashed me around as if I wasn't even there. One last rippling fart slipped out of her as her climax peaked, causing me to nearly throw up in disgust.

Miss Cheston's climax soon ended, and she leaned forward while nearly out of breath.

"That's better, but next time you'll serve without the need for punishment," she choked out. "That was an easy reprimand. Next time it won't be nearly so pleasant."

The old woman rose and composed herself. I was left on the floor beneath her, a filthy mess of sweat with the odor of stale farts still wafting around my head. The taste of her ass on my tongue was the worst of all, though. No amount of brushing or mouthwash would ever truly get it out.

Miss Cheston checked her watch.

"It's about time for your wife to return home," she said. "Let's get you ready."

Miss Cheston grabbed my leash and asked for me to rise to my knees. I crawled behind her like a nervous pet as she walked me to the front door. I was still trembling and in a daze from that horrific punishment when the door opened and my wife burst in. She was grinning and sloppy, her hair quite the mess. With the way she stumbled, she had been drinking as well.

"Ah Miss Cheston, I trust Dan behaved well enough?" Sarah asked.

Miss Cheston crossed her arms beneath her breasts and shook her head. "Not really, but proper punishment was administered," she replied.

Sarah laughed. "That's good enough for me, I trust you'll be back tomorrow to continue the training?"

Miss Cheston nodded. "Yes, every day this week," she replied. "Of course, there's one more duty I'd like to supervise before I depart."

Sarah's eyes lit up. "Oh right! Let's get to it."

Miss Cheston yanked on my chain as Sarah stumbled over me and lifted her dress. She wasn't wearing any underwear, and her wonderful pussy was glistening. Miss Cheston grabbed my head and forced it closer to my wife's crotch. It became glaringly obvious why her pussy was so slick, there was cum all over it.

Before I could react, Miss Cheston had forced my face right up against it.

"Lick your wife's lover's cum, cuckold," she ordered. "This is your primary duty. Show her your obedience."

The salty goo had already begun to drip onto my tongue when Miss Cheston gave the order. It took all of my strength not to gag. I considered protesting but remembered what she had done to me earlier. Compared to that, this task would be a cakewalk. Still, something about it was almost more humiliating.