The grocers stares came often as Anna pushed the shopping cart up and down the various aisles. Vacationing families, the remaining college students, and old ladies all had double takes as the cuffed girl made her way around the store. Anna blushed, but all she was concerned about was not seeing anyone she would recognize.
Luckily the list Miss Crosby provided was short and simple. Three bottles of white wine, a bag of grapes, some sort of artisinal cracker and various wedges of cheese. She picked up some prosciutto, smoked sausage and something called patě. The young girl that handed her the sliced meat didn’t bother looking at her eyes once the lock on her wrist cuff jingled. They both blushed.
Anna hit the self-checkout in an effort to stifle any more stares. She felt guilty, as if Miss Crosby would be disappointed. But she quickly made her way to her car and was on her way.
She pulled into the gated entrance, the guard waved her through as her visits had become that routine. Anna took a different way this time, circling around the expansive neighborhood and eyeing the various styles of mansions and estates. Pillars, cape cod style houses, some ugly some gorgeous. The cars were all high end, BMW and Mercedes Benz, Jaguar and Range Rover. Surely the neighbors had to wonder what the 1998 Nissan Sentra was always doing parked in Caroline Crosby’s driveway. It stuck out like a sore thumb.
Anna’s stomach churned as she turned the corner. Miss Crosby’s Audi was always parked in the garage and the driveway was always empty. But today 3 cars joined Anna’s in the driveway. All brand new, all luxurious. The grocery list all of the sudden revealed its true intentions.
She let herself in as she’d done a dozen times before, and was immediately greeted with a murmur of chatter and laughter. The grocery bags hit the floor silently and Anna had to muster up all the discipline to not walk passed the foyer and into the kitchen. It was clear Miss Crosby had guests over. Maybe she just wanted Anna to run out and get a few bites and snacks, and she would be shooed away as “plans changed at the last minute”.
She left the two bags on a small bench and slipped herself into the bathroom. There, her hopes were dashed. She hadn’t been this apprehensive and nervous since her first visit.
**Annabelle,
As you can surmise, I have guests over. Today you will be less of my personal maid and more of a servant. Do not be nervous, my friends and I will be by the pool when you arrive. They are well aware of my personal and private delights and the type of girls I fancy, but this will be the first time they’re privy to meeting one. Be proud, Annabelle, you’re the first one to be shown off. Please, do dress and greet us.
-Miss Caroline**
“Jesus fucking christ” Anna swore out loud. She read the note over once more. The way in which this woman would simultaneously humiliate Anna (calling her a personal delight), and mix it with praise (first one to be shown off), couldn’t be executed any better. The key to the cuffs was present, Anna unlocked them to get dressed, and promptly put them back on, as she didn’t care to be reprimanded for a uniform violation. Her uniform remained the same otherwise, save for a pair of nipple clamps that were adorned with 2 bells each. They didn’t pinch harshly, the teeth were solely used to affix themselves to the tanned nipples of Anna. These were meant to be worn all day and to jingle at every step.
They did.
The first few steps took Anna to the kitchen, where she placed the bags on the counter she was so very much fucked over just days prior. She could hear the voices clearly now, including Caroline there was 4 total women.
Anna surveyed the three strangers. They were all in sunhats and glasses, their faces obscured. One woman was a bit overweight, her one piece hiding her middle-aged mom belly. The second was blonde and very thin, freckles could be seen even from this distance. The third was built more like Miss Crosby. Her breasts did all they could to slip out of her bikini top. She repositioned herself on her belly to tan, Anna blushed at the sight of her thick, juicy ass.
She opened the sliding glass door, the pool babbled and birds tweeted away as the bells of Anna’s nipple clamps gave away her arrival far before the clicking of heels or a “Good Afternoon” could.
Miss Crosby was the first to notice. She smiled at Anna and stood up from her chair.
“Girls, I’d like you to meet Annabelle Prescott”
They turned and gawked, and for a second Anna’s world stopped, and everything went mute as if some bomb went off and stole her hearing. Her ears buzzed, and not in anyway that would stimulate her. There she stood, her pussy exposed to strangers, her tits clamped with her breasts on full display, in lingerie normally reserved for intimacy. But what most surprised Anna about this particular situation was that her mind immediately snapped to obedience. She spread her legs, placed her arms behind her and together, and kept her shoulders back, back straight and eyes forward.
“It is a pleasure to meet you, Annabelle” one of the women said.
“There’s no need for introductions, ladies.” Miss Crosby made her way to Anna and made a slight adjustment to her clamps and continued on “Miss Prescott here is a very diligent maid, and completely understands the importance of discretion. She does not need to know your names, and will simply refer to you as Miss, or Ma’am. I am assured your own discretion is without ask. You may refer to our servant as Anna or Annabelle. My guests would prefer wine, make yourself useful, one glass at a time please”
Anna thanked Miss Crosby. “It is a pleasure to meet Miss Crosby’s closest friends. I hope I serve you well today” she smiled as if she were serving a table at her work. Unsure of where those exact words came from given that she was terrified, she pivoted in her heels and hastily retreated into the confines of the kitchen.
“You were not lying about her butt, Cari” she heard a woman say.
*Cari*. Not Caroline. Her friends called her Cari. There was so little she knew, and that made everything so much more surreal.
The four glasses of wine took four trips out. By the last trip with wine, the thin woman was standing with her feet in the water, on the first step of the pool. When Anna handed her the glass, she spoke to the women.
“God, I remember when I was this perky. No extra skin anywhere, no need to go to the gym everyday, just blessed with great tits”.
The woman reached out with her free hand and cupped Anna’s breast. This took her a bit by surprise, the freckled woman seemed apprehensive at Anna’s retraction. “Annabelle” Miss Crosby spoke up “Spread your legs like you were taught, arms back. Allow for inspections”. *Inspections*. Her pussy tingled.
Emboldened by the obedience of the girl in front of her, the woman brushed Anna’s hair back behind her ears and jingled her clamps, pinching the metal teeth with her own fingers. She ran her finger around the top of her smooth pussy, noting how “girls these days shave everything”. Anna, mind swirling, enjoyed the soft touch of the tiny and red headed woman. Goosebumps raised on her skin and a firm grabbed a hold of her butt cheek. The woman spoke not to Anna, but of Anna. She was truly eye candy in this moment.
“It is much better that way” Miss Crosby replied. “Girls these days are also very open to anal. When I was in college that was an impossible feat. Now, they barely put up a fuss.”
The women were curious about this fact. They discussed anal for quite some time, peppering Caroline with various questions ranging from the childish (how do you make sure there isn’t shit) to technical (how do you insert bigger items, how long can one keep a plug in).
Anna eavesdropped as much as she could. These three were your typical middle aged chatty kathys. They discussed husbands, kids, affairs. Other, obviously less important, friends and accomplices were talked about and ridiculed. Anna had served them two glasses of wine a piece, but Miss Crosby had barely touched her first. Caroline talked the least, and Anna had the feeling she preferred the women paid more attention to the nude girl in front of them. This made Anna feel uneasy and worrisome, a trivial thought though, blending in seemed the easier route compared to the alternative. That’s when conversation turned back towards the college student. It was a wonder to Anna that they could somehow manage to not discuss their best friends topless maid.
They asked Caroline about the outfit, marveled at Anna’s abilities to walk in the heels, mentioned her butt time and time again. The heavier woman asked what the leather cuffs were worn for. Their eyes widened and they sat forward when Miss Crosby informed them that Anna always cleaned shackled.
“Annabelle, sweetie. There’s a Louis Vuitton rolling bag sitting at the edge of my bed. Please retrieve it, and bring it poolside. There’s no need to look inside”
Miss Crosby was correct, there was no need to look inside, as the bag was heavy, zipped shut and so obviously containing a multitude of bondage gear.
Source: reddit.com/r/gonewildstories/comments/5wak2o/my_time_as_a_maid_part_vii_ff_bondage
Looking forward to Part VIII!
So is this the last part?