My Time as a Maid [FF] [Bondage] [Part IV]

Anna found herself bent over again. Her heels did an exceptional job of propping her ass into the air, which gave Miss Crosby a large, centered target for the cane she held in one hand, tapping it into the palm of her other.

The hemp rope held her wrists together. Extended outward before her, and anchored itself taught and out of sight as the rope disappeared over the edge of the granite-topped kitchen island.

She had been bound for 15 minutes or so when the cane introduced itself to her skin, crashing down on Anna’s cheeks with a forceful blow. The sting was equally dispersed, erupting immediately from the whack. She cried out as the light tapping was alternated with hard slaps, which continued to paint red welts all over the thick ass of Miss Crosby’s maid.

She tried to move her ass, shake out the pain, but nothing worked. Anna had been spanked before by excited sex partners. With combs or open hands or the rare belt, but this wasn’t done as “rough sex”. There was a purpose here. To hurt her, and teach her a lesson. It was physical as much as it was emotional and mental, and poor Anna had to endure the punishment, the cascade of tears be damned.

Just an hour or two earlier she had cleaned in her restraints easily enough, making quick work of most of her typical duties. Her second day in bondage went by faster as Anna became more familiar with the shackles and more rehearsed in her maid chores. Miss Crosby spent the day by the pool, so it was with great surprise when she informed Anna that the maid had not completed all of her duties, and as such, must be punished.

“You understand why this is unacceptable, and why as my house maid you must be punished, correct?”

She stared daggers at Anna as she bound her wrists and bent her over the kitchen island. Whatever the punishment was going to be, it couldn’t be any worse than the look cast upon her, or the way Caroline spoke to her maid. Anna was incredulous, she double checked all her chores before reporting to Miss Caroline, and when she asked what she had forgotten, it was met with a sharp, cold, calculated “you know what you did”. She wanted to cry, and was successful in holding back tears up until the point when her ass was destroyed.

“You did so well last time, too. Maybe you grew too confident after I rewarded you. Success getting to your head, Miss Prescott? I think you need to focus, realize that I can drop you just like that.” The snap of her fingers emphasized how fast she could ‘hire’ someone else. Anna didn’t like that, her whimpers filled the kitchen as Miss Crosby teased, reprimanded and threatened.

“I’m truly sorry, Miss Crosby. I promise it won’t happen again, I will triple check every single chore assigned to me, you deserve only the best maid to service you and your household” Anna attempted to look the woman in the eye, wanting to reassure her was more about action than words, but talking face to face was better than talking face down to granite counter top.

Something cold and lubricated pressed into Anna’s now exposed asshole. It slid itself in despite the wiggling and whimpering from Anna. The anal penetration was a first. Anna had been curious about anal, but a lack of any long term boyfriend in her life always kept her from exploring the pleasure that she imagined would be derived from having her butt fucked. Her cheeks were spread by one hand and the buttplug was stuffed into Anna’s ass with the other. It burned going in, feeling stretched wasn’t a pleasurable experience, but once the whole plug was in and her now hungry hole hugged the toy, a little relief was welcomed. Then, it began to expand.

Miss Crosby gripped the tube dangling from the plug and closed her fist around it. One pump, two pumps, three pumps filled Anna’s butt with a rubber, baseball sized sphere. She knew what a buttplug was, she didn’t know they made ones that could be fucking inflated. The punishment may not have been warranted, but it sure was proper. It would get worse.

The implement came crashing down again on Anna’s ass. It was round two of caning. She yelped out, practically leaping over the island. If it weren’t for her bondage, the poor girl would have scurried right over the counter. Repeated blows all over her thick behind left her pleading for Miss Crosby to stop. She knew it was a fruitless endeavor, but she still had to plead for reprieve. The welts raised quickly, and Miss Crosby made sure to remind Anna that when she tried to wiggle out the pain and dance around the song the cane was singing, it only made the tube exiting between Anna’s buttcheeks swing back and forth. She pumped it twice more before the caning resumed.

She would tap the spot, warming up her skin with a flick of the wrist for a time before ramping up the force in which she torqued her wrist, ending with a sharp smack on Anna. She repeated this for what felt like an eternity, the burning ass of her maid was as red as the glass of wine that Miss Crosby held in her left hand, tears flowed down her cheeks and pooled on the counter.

“I think that’s enough corporal punishment for today. Let’s dry off those tears and let you think upon your indiscretions. Do you recognize these?” Anna had to see past the water still welling up in her eyes to make out two pairs of panties. She shook her head yes while sniffling.

“You left these in the dryer. I found them when checking your work. This is unacceptable, it is not my job to empty the dryer, nor fold my underwear. That’s what I pay you for. If I have to do your job, that makes you useless. Do you want to be useless, Annabelle?”

“No, Miss Crosby. I want to be the best maid I can be. I want to be useful, not useless. I am so sorry, it won’t happen again, Miss Caroline. Please, let me make it up to you in anyway…”

“Oh, you are right now sweetheart. You look great even when you’re tears have smeared your eye makeup all down your face. Let’s clean you up?”

The panties muffled themselves into Anna’s face, cotton, freshly laundered and soft. They mopped up the tears, and were now covered in mascara and eye shadow and blush. Her ass apparently couldn’t be the only thing stuffed, as the panties were not only shoved into Anna’s mouth, they were secured with multiple layers of duct tape being wrapped around the poor girl’s head.

“I can’t have you whimpering any more, and I don’t care to clean up your pathetic drool from my counter top, so I might as well use those panties to solve both issues. After all, it must be of your opinion that panties aren’t to be folded and worn as underwear, otherwise they would have been properly placed into my dresser drawer and definitely not shoved into your mouth”

The plug was deflated in her ass and removed. The feeling that washed over Anna as the toy slipped itself out of her asshole was euphoric, relieving and still humiliating. Anna’s first anal experience could not have been predicted. Her second was just as surprising and degrading. Now, she was going to take a strap-on dildo into her properly prepared ass.

Her pussy grew wet as the woman pounded into her. It burned less than her welted cheeks, as the rubber cock probed into her hole. It spread her wide, the cock was less stuffing than the buttplug, but still felt huge in her ass and spread her hole much wider as it was thrusted in and out, over and over. She looked over her shoulder, trying to see the sight behind her, but all that resulted in was a few more spanks onto her welted ass and her hair being yanked. It was frustrating to Anna that she couldn’t see this beautiful woman as she had sex with her. She surmised that was the point. Punishment, objectification, humiliation. Obviously Caroline wanted it this way.

“Is this turning you on?” Anna’s gagged “Yes, Miss” was understood well enough. An abused, welted and burning set of asscheeks, a stuffed, then fucked butt, panties duct taped into her mouth, all experienced while naked and in bondage, and it absolutely was turning her on. How ridiculous. She felt ashamed, yes. Being yelled at was no fun. Disappointing this woman was terrifying. And yet, she could feel her pussy juices dripping down her leg and seeping into the fabric of her thigh high stockings.

The sounds of Miss Crosby breathing heavy and Anna whimpering echoed through the kitchen. Anna was pressed onto her toes when the cock was hammered into her, the heels clattered off of the tile as she came to rest, only to repeat itself. Obviously this wasn’t going to result in either of the women achieving an orgasm. So, on one hand Anna felt disgraced that she couldn’t be of any use in that regard. But on the other, knowing Miss Crosby would come up with all of this just to punish her had made her, for some absurd reason, feel special.

“Are you going to get yourself off when you get back to your bedroom?” Again, an emphatic and gagged “Yes, Miss”.

“Aw….how cute.” Miss Crosby patronized the butt fucked maid “I apologize Miss Prescott, but you will not.”

The cock slipped out of her, and with Miss Crosby, disappeared entirely. Relief came over Anna’s butt, having her hole devoid of the thick, rubber dick was incredibly welcomed after the hard fucking. She let out a loud, muffled, deflating sigh.

Anna had to wonder how Miss Crosby intended to stop her from playing with herself. She had thirty minutes to think on it before her questions were answered.

The metal, possibly steel, piece of equipment Caroline flashed in front of Anna looked like a bizarre pair of panties. Although it wasn’t something you picked up at a woman’s store, it was for better or worse underwear. The chastity belt was to be worn for five whole days. The metal locked itself around her waist and helped secure the other bit that ran between her legs. When the lock clicked shut, and the key disappeared back into Miss Caroline’s cleavage, Anna’s punishment was complete.

She would not be touching her pussy.

“Now, I’ve untied the rope from the island, you can figure out how to free your wrists. The lock to your ankles are with your pay in the envelope. You will also be responsible for your gag. I’ll see you in 6 days. Don’t be late, don’t complain to me about your new piece of clothing, and do not, ever again, leave behind laundry.”

((Thanks for reading this far. For whatever reason I felt this portion was a bit clunkier than the rest. Let me know what you think!))

Source: reddit.com/r/gonewildstories/comments/5py9hh/my_time_as_a_maid_ff_bondage_part_iv