Finally, after months of searching, there it was! The ad Jennifer had been searching for finally showed up on Craigslist! She just knew this was the right one for her, she could feel it!
Housekeeper with Benefits Wanted: Rubenesque, petite brunette wanted to perform chores around home. You must be submissive and obedient, willing to take instructions without question and willing to accept punishment if you do not perform up to par. I will teach you what I require and you will learn as you go. I am waiting for you to contact me for more information. I expect you to respond promptly.
Jennifer was typing a response email almost as soon as she had finished reading the listing. It was so exciting to find the right ad; she couldn't wait for the response.
I believe I am the maid that can provide you with all the services you require. My housekeeping skills are impeccable and I am willing to provide additional services that you may so desire. I am new to this, but am a quick study and eager to please. If you are willing to teach me, please contact me.
On a whim, Jen decided to attach a copy of herself in her old French maid uniform. She went with it figuring that it accentuated every curve of her voluptuous body. In her mind the picture was a gamble. She had responded to CL ads before, only to be disappointed. This outfit used to fit a little better, but she had put on a few pounds and gravity was taking its toll in the years since she bought it. Jen had met a few men, sight unseen, only to be told that they considered her too old, or that they were expecting a 20-something gym body. They wanted a tight firm ass, and perfect breasts. "Perfect," she thought, "you mean fake! These are all me and someone needs to appreciate that!" Glancing out the window, Jennifer saw the local hottie jogging down her street. Rachel Bream was the teenage daughter in the house on the corner. Her long golden locks and large breasts always turned the heads of the neighborhood boys and men. Sure she may play innocent, but we all know that she knows damn well what she is doing when she squeezes on that obviously small sports bra and those skin tight bike shorts to run in. "Enjoy those big firm boobs now," Jen says aloud to herself. "They may be nice enough to get you some attention now, but in a few years you are gonna look like me." Jen glances down at her sagging D-cup breasts, barely covered by the maid costume. She unties the neck straps and turns to look at herself in the hall mirror. Cupping each breast in her hands, she raises them and says, "We've had some fun in our days, haven't we girls?"
Jen lowered her breasts slowly to their natural level, almost as if watching gravity take its effect on them through some high speed camera that has filmed her over the years. She thought back to the first and only time she put the outfit on for her former boyfriend. That was several years ago and the two had been living together a few years. She was looking to spice things up a bit and decided to surprise him when he arrived home from work. But instead of the reaction she expected, he told her to take the silly thing off. It's not Halloween he said... That had been the final straw with him. Shortly after that, Jen moved out on her own again. In the years since, she has pursued her sexual education. The internet was a wonderful place for her to discover so many new things. In retrospect, she realized that her old flame was actually holding her back. If she were still with him, she never would have discovered the wide open world of fetish sex, and her most recent interest in being a submissive. Just the thought of being controlled by some strange man excited her.
At first Jennifer checked her email inbox every hour. She was so aroused at the thought that she could feel her panties get damp each time she logged in searching for any response. With none in the inbox, she was dying to give her hot loins some attention. Just a few fingers briefly, she thought. The good stuff is yet to come. "Mmm," the moisture on her fingers tasted like honey on her tongue. "How long before he samples my kitty?" she wonders, as she slides her fingers in again. Her fingers are sufficient for now, but she grows impatient as the hours, then days go by.
It actually takes the better part of a week before something happens. Jennifer was actually starting to feel like this was not going to be the one. Doubts had clouded her mind and she was just about to give up. She decided to look for the last time. "If he hasn't answered me now, I will give up," she decides. But there it was! On her last try, the response had finally arrived!
You have waited for me this long. I see you can be patient. You have passed the first test. Most other responders send another email before the week is out, but you did not. I like that.
"He likes me! He likes me! Oh I hope this works out!" The moistness between her thighs returns as Jennifer read on...
I require two things. You must arrive to my home attired as I direct, and you must respect my time. If you will commit to these things, we may proceed.
Jen's response is short and to the point.
Sir, I am eager to serve and please you. Please allow me the chance to prove it.
A day later his response is received. Jennifer practically cums in her pants when she sees his message in the inbox.
You have been granted the chance. Do not let me down. Tell me your sizes so that I will have the proper uniform for you when you arrive.
"Sizes," Jen wonders. "I have my own maid outfit already, but if I must follow instructions, I will do as I am told."
I wear a size 10 pants and a medium or large top, depending on how tight I want the blouse.
Jennifer figured she would give her new mystery man the chance to decide if he wanted her in a clingy outfit or not. It seems the game had begun already. "I wonder what sort of uniform he is going to make me wear."
In two days' time Jennifer received another email instructing her to come to his home on Saturday in the early morning for a 6am start. She was to wear absolutely nothing under an overcoat.
Your uniform will be provided when you arrive.
In the early spring an overcoat is not a problem, but in the mid summer Jen wonders if an overcoat will provoke questions from the neighbors. "Wow," she thinks. "This guy is serious business!"
Saturday arrives and Jennifer has prepared herself as instructed. After a shower, she shaved her pubic hair, and applied her sexiest body lotion scent. Striding to the front door wearing nothing between her smile and her green sandals, Jen takes an overcoat from the closet and puts it on. She carefully ties the waist belt, takes a deep breathe and steps out her front door. Walking down the driveway, Jen tries to shake the feeling that the neighbor next door picking up her paper from her lawn knows what she is up to. Jen throws up a polite wave as she walks to her car, not wanting to let go of the coat for too long. Climbing into the front seat she notices a heat growing between her legs, and grabs the coat flaps to ensure she doesn't flash the neighborhood.
Thinking about what is the day may bring as she drives, the heat between her legs continues to grow. Squirming in the driver's seat, she can't help but reach a hand between her legs at the red light. She smiles at the male driver in the car next to her as the light changes, waving her cum soaked fingers "good-bye" as she speeds off. It is one of those times that she wishes that she was not driving a stick shift so she could continue her fingering as she drives, but she has another idea come to mind. Turning the a/c vents, she manages to send a cool breeze directly into her lap, helping cool the fire down below. The exhilaration is inspiring on the drive.
Turning into the driveway, Jennifer can see his modest home. It is not the awe inspiring mansion she had imagined, but she was not going to let that spoil the excitement. It was a two-story brick house with a chimney on the roof. "Must be at least a 3 bedroom." she evaluates. In the driveway, again cautious not to flash the old man on the next driveway, she clenches the bottom of the coat as she walks up the driveway in the morning breeze. The cool morning air is enjoyable as it flows up between your thighs.
Jen rings the doorbell, and the door opens wide. With the shaded by the trees in the front yard, she cannot see the face of the man that greets her, but she hears his gravely voice,
"You are quite prompt. Very good. You may address me as Sir. Do please come inside." Stepping thru the door, he shuts it behind you and asks if she has dressed appropriately. Jen nods her response. "Please remove your coat and hang it on the stand by the door." Turning towards the stand, Jen's stomach starts to churn. The feelings of insecurity start to creep into her mind. Untying the belt, the fear of rejection starts to cloud her brain.
"Why do you hesitate," he asks her?
Jen realizes that she had frozen to the spot and not yet removed her coat. A strong hand rests on her neck from behind. His breath is warm on her neck as he says, "Let me make myself very clear. I expect from you absolute obedience, and immediate satisfaction, do you understand?"
His hand tightens on Jennifer's neck with the question, and his other hand reaches to pull her coat open. She feels the air conditioned air on her backside for the briefest moment before his free hand comes in hard and loud on her soft white generous bottom. A moan of pain escapes her lips as her hips lunge forward in reaction to the slap. Jen is not sure if she was actually hurt, or just shocked.
"Now," he says, "down the hall on the right, you will find a room containing your uniform and cleaning supplies. Please put on the uniform and bring the bucket back here with you."
Slowly Jen slinks down the hall, thinking about what just happened. She dared not turn her head to peek at her backside, but she imagines it is already turning red. She knows he is watching her, and she hopes her imperfections are not disappointing him. In the room she finds a mattress on a metal frame. It resembles a military bunk in its simplicity. On the bed is a bucket with several items inside. Some she identifies as cleaning tools, but the rest, for now, are a mystery. Hung over a chair is the uniform. A purple sleeveless men's undershirt, the kind affectionately called a 'wife beater.' Under the shirt is a purple pair of panties, cut more like shorts than underwear. Pulling on the top, Jen realizes that it's too tight. "This has to be two sizes too small," she thinks. With each breath the fabric mercilessly squeezes her breasts. The panties are too small too, leaving more than half of her ass cheeks hanging out the bottom. They take some getting used to, but the fabric is quite forgiving.
Jen takes a moment to look at herself in the mirror. A deep sigh escapes as she does not like what she sees. "Why is time so cruel to women and not men," she asks as she looks at her sagging breasts again. The men used to stumble over themselves as they used to compete for her attention. Her diminutive 5' 2" 103lb frame only accentuated the size of her 34D bustline. Her long flowing auburn hair waved freely in the breeze, waving in potential male suitors. In recent years though, she has put on a few pounds and inches. The washboard stomach is gone, and everything has started to sag. The auburn hair is still there, but she occasionally helps it out with a dye job. "Well," she thinks, "youth doesn't have experience. At least I got that!"
Jen grabs the bucket and walks back down the hallway hurriedly, knowing she has made him wait. He is standing in another doorway now. He ushers her through and she is standing in the kitchen.
