the-hostess-with-the-mostest
TABOO SEX STORIES

The Hostess with the Mostest

The Hostess with the Mostest

by Billwells1
20 min read
4.53 (26400 views)
reluctancegangbangblowjobsgang bangoral sex
Loading audio...

It was the afternoon of my eighteenth birthday when I was walking up to the door of our fourth-floor apartment, I saw the bright red notice taped to the door informing us that the sheriff was giving us just 24 hours to either settle our debt to the landlord or we would be put out of the building. After lugging two shopping bags of groceries up four flights of stairs, I almost dropped to my knees and cried. I probably should have been more deeply surprised, but I was familiar with that type of warning. We've moved on the run before, leaving no forwarding address. This should have ruined my day but it was only the beginning. Later, when my mother came home, she let me in on a bigger secret, that her brother had been fucking her.

My name is Angela and I was about to come face-to-face with some very difficult and disgusting truths. My mom was my guardian, my sounding board and my closest ally. I never knew my father, he didn't marry mom and apparently didn't care for either of us. One set of grandparents were no more than shadows, the other died before I got to know them. I have one surviving uncle whom I would have trouble picking out of a lineup, I was just turning eighteen and my body was maturing way ahead of the rest of me. School was a challenge but I liked learning new things, however college would be way beyond my means. I was dependent on my mom for income and housing, plus her guidance and judgement was all that I could rely on. Today would be a test of all of that.

I went from despondent to disbelief. So many new and intriguing facts were being thrown at me at one time and in the background, the ticking of the clock was like the countdown to a rocket's launch. My home, my mom and my nearest family were all thrown into doubt. Suddenly, I needed to see the two closest relatives in my life as entirely different- and possibly loathsome- people. And I needed to make my mind up about them, in a hurry.

My Uncle Tim, who was almost twelve years younger than my mom and just a few years older than me, currently employed mom as a housekeeper in his home and it appeared, kept her on the side as his personal sex-slut! My mother Tanya broke the news to me matter-of-factly, fingering the poisonous eviction notice as if it was not unexpected and declared that Tim had offered a solution to our problems that I only needed to agree to, and we could soon both be living in his fancy house. If I would help her with the general upkeep of his big house, he would provide us both with our own rooms, private baths and a salary. He lived alone in a four-story, 20-room mansion, that was used mostly to entertain his business dealings about once or twice a month. The rest of the days would be preparing meals for the three of us, shopping, laundry and cleaning. And then, there was the part that would scrupulously remain unspoken. We would essentially become live-in maids who cooked and cleaned, while allowing him to fuck us both.

That "out of the goodness of his heart," Uncle Tim would become our benefactor and all would be wonderful; big home with no bills, routine housekeeping as salaried job, and mingling with his high-end party guests representing the swell people in society and leisure time to enjoy ourselves, what's not to like? This was the same guy of whom, not one single family photo existed. The Uncle I barely knew, but to receive envelopes with money in them and phone calls on holidays. The man that my mom had no childhood stories about and only recently became the subject of his obviously lewd largesse. And the guy who would be entitled to enter my bedroom at any time and spread my legs for whatever sexual perversions he imagined.

Though she didn't come right-out and say that this would be one of my chores, the distasteful impression was in the air. And as well as she camouflaged her own willing participation in this sordid tryst, I got the uneasy notion that she was recruiting or shanghaiing me into this lewd scheme. She seemed surprised and a bit disappointed that I didn't jump at this magnanimous bargain. I didn't have the time- or the opportunity- to engage the twelve stages of grief. Mom was perplexingly accepting of this twisted, incestuous arrangement. I learned later that she was more than comfortable, with "the give and take" of it all.

The clock was ticking on our acceptance, and the alternative was bleak but still I had my doubts, (to say the least.) Mom also mentioned as a sword of Damocles, that she was informed by my uncle that this deal had an expiration period and that it was non-conditional. It would be either a mom/daughter sexual package or no deal at all. As repulsive as that may be, it was also a sister/niece debauchery. And I wasn't quite sure just how much of this illicit scheme had been orchestrated by my mother. I felt trapped and amazed that she seemed so nonplussed at these vulgar, incestuous conditions that were presented to me, with no prior warning or plausible escape. Yes ofcourse, I could have declined or spit in the face of each one of them. Then I could pack my feeble belongings in a garbage bag and appear on the doorstep of some high school friend like an orphan and beg to stay without providing any explanation for my forlorn disposition. The alternative was a refrigerator box by the bridge stanchion of the overpass.

I don't want to pin this all on my mom, or to blame her for placing me in this uncomfortable predicament, she didn't exactly choose this dilemma. Her upbringing had been a blur of shifting relations with no real base of support. Tim offered her work in his mansion that began as a one-time hostess for one of his parties and progressed from there. Nor do I wish to blame my uncle, though I find him at this minute, to be a complete shit. Until this moment, he was my favorite (and only,) uncle. His birthday and holiday gifts to me, were always unique and high-quality, and he would often slip money into my fist for movies, field trips and vacations. He would say that a young person needed to know that the world held good things, too. I never imagined that there could be a sinister underside or that he was "grooming" me for something evil, and I still don't.

After crying into my pillow for about an hour and lamenting the "woe is me" scenario, I realized that I wasn't really equipped to face the big, frightening world in any fashion that would allow me food and shelter for the immediate future. My recent graduation was by the skin of my teeth and my biggest accomplishment was becoming assistant head-cheerleader, that milestone involved only one blowjob.

📖 Related Taboo Sex Stories Magazines

Explore premium magazines in this category

View All →

I came back into the kitchen where mom was still sitting at the table in the same position that I left her, only with the addition of a pint bottle of vodka which she liberally poured into a glass of orange juice. When I sat beside her with a second glass of juice and reached for the bottle, she gave me that motherly look that implied that I'm underage and under stress, but then she realized that at this point, I was about to mature way beyond my eighteen years.

"Tell me again, mom..." As I watched a slow dollop of 80-proof reality lightening the orange liquid in my glass. "What exactly is the deal here?" She took a big swallow and a deep breath. Then she reached for the bottle and refilled her glass, clinking our drinks together and nodding solemnly, she began to tell the story.

My mom had two brothers. Jim was two years older than her and Tim was more than ten years her junior. Her father had died, leaving a small insurance policy that didn't go far for a wife with three kids. Jim died in a mysterious accident that also sent her mom over the edge, she passed shortly thereafter. Just entering her teen years, mom was sent to live with an alcoholic aunt and Baby Tim to an orphanage. There was a modest sum of money from her mom's "estate" which her aunt used to help raise her until she could be on her own. Tim was placed in a group home in another city with his share of the money held in a trust until his twenty-first birthday.

Time must have flown by for them both. Mom saw life as one continual struggle, something just short of Cinderella's, before kissing the frog. Tim probably wished that he owned a frog. Neither mom nor her aunt visited Tim on any regular basis and Tim had no clear memory of them until he was a teenager. By the time that Tim reached his twenty-first year, his sister was nearly 35 and their aunt had died. Tim's solitary consolation was comics, and he became quite an amateur artist in his own right. When he was able, he took the small investment from his trust and opened a boutique advertising firm that filled a unique niche. In just a few months, some dot.com asshole purchased it and abruptly, Tim was a millionaire. He then, invested in a marketing firm and another dope bought him out, again. He was now a multi-millionaire looking for something to entertain his twenty-three-year-old self.

Mom had no such luck. Now in her mid-thirties, her years matched her bra-size and both were beginning to droop. She had limited education and even less finances. Her greatest asset was her impressive bustline and men took advantage of her. She held tipped/wage jobs for a while and worked briefly as a "dancer," but the years and gravity were creeping-up on her. Through no real fault of her own, she had lost most contact with her younger brother- though mostly from distance, not loss of affection. She didn't even hear that he was a rich man until much later.

Still, as a middle-aged woman with one child, she had a slightly-used- yet sultry- sex appeal. She has shoulder-length brunette hair, with a touch of grey and almost almond-shaped brown eyes. Both traits that were passed to her daughter, my hair wasn't yet grey, (though this new "job" might be a test,) and I wore mine down to the middle of my back. We shared cheeks that were rounded and lips plumped full, a pleasing and sensual effect, though hers were bordered with added creases around her mouth and eyes. And she was buxom, to put it mildly. I had an ample chest, sporting a 36C but looked underfed compared to mom's bountiful rack. When stepping from the shower, my tits still bounced and the nipples pointed straight ahead, my mother cannot make the same claim. Yet, with all of that chest on a much shorter frame, no red-blooded male would turn her away. She remained curvy, if a little more jiggle than she would have preferred, and at about 5'5" she presented a dynamite package.

I am about three inches taller and have long, toned legs. Being taller makes me appear leaner but her petite frame looks to be built for pleasure. She has every desirable curve but her luscious body is cruelly softening with age. My belly remains slightly rounded through all of the gymnastics, and my ass is small but pleasingly solid. Going braless, the swaying effect of my front porch has caused men to walk into walls and even when more formally-attired, my drip-catchers present a solid profile. I look good in tight jeans, a side-slit skirt or anything with heels. Bending and stretching for four years kept things tight and supple. I am often complimented with a sexual innuendo, that I must be remarkably flexible, (I am.) Plus, I enjoy sex. I am not a sleep-around slut but my virginity is a thing of the past.

And I was about to make, (with an 80-proof boost,) the most important decision of my young life. This could be the last time that I needed to sleep under threadbare blankets with the leaky, rusted pipes of an overtaxed heating register attempting to offset the swirling breeze from the ill-fitting windows. Mom has told me tales of the magnificent house. Two gigantic refrigerators, a restaurant-quality stove, chandeliers, oriental carpets, an entire floor to ourselves. All of this for the simple exchange of my sexual virtue and the willingness to ignore any moralistic qualms centering on taboo perversions. It wasn't an easy choice but it wasn't difficult, either.

In the morning, Uncle Tim arranged for a driver and van to haul our stuff to his house. We loaded up our essentials and some appropriate clothing. A few favorite pieces of furniture and sentimental knickknacks made the trip, but the rest could be used by the bastard landlord to plug all of the leaks. There were no tears shed as we pulled away but the mood as we approached the wooded community that harbored his spacious enclave was unsettling. Mom worked in the house, but I gather that she was contemplating something different with having me around. My mind was a tempest of emotions that I had no control over. In our private thoughts, we both had to come to grips with the contract that we were about to enter into. A sort of cross between a gold-digging woman and a beaten dog.

🔓

Unlock Premium Content

Join thousands of readers enjoying unlimited access to our complete collection.

Get Premium Access

🛍️ Featured Products

Premium apparel and accessories

Shop All →

When we turned into the tree-lined drive and pulled under the covered portico, it felt awkward to drag our bags of second-hand plywood furniture and bargain-basement clothing across the parquet floors and oak bannisters of the grand English-style estate. Uncle Tim wasn't there to greet us but the driver let us in, and mom gave me the "cook's tour." Entering the marbled foyer and peeking left and right into giant rooms was like being in a museum. Obviously, there was a full crew to keep this mausoleum so immaculate, I suppose that mom was a "pity hire," and just there to distribute food and drinks. The sunken living room seemed large enough to play basketball and the formal dining room featured a table that sat thirty. There was a den that resembled The Oval Office and a glassed-in sunroom with tropical plants and rattan loungers that overlooked the inground pool. The downstairs held a billiards room with wet bar and a screening room that looked like the fanciest movie theater. The main floor had a formal kitchen with a dumb waiter, while the upper floor had a casual kitchen and living space along with guest quarters.

Uncle Tim was growing in my estimation, (I know that sounds terrible,) and women have been indebted to worse businessmen. But the fact that he came from nothing like me, had a miserable childhood and yet made a fortune that he is still young enough to enjoy, gave me some type of inspiration. The idea that he may be terribly perverted and that I may become an accomplice to my own degradation, gnawed at me but also lit a taboo tingle in my apprehensive uterus. Can money buy happiness? Only poor people say that it can't. It doesn't make a man more honorable or decent, but a whore with money is better-off than a poor one. There is an old expression that states: "Life is like a shit-sandwich, the more bread that you have, the less shit you have to eat!"

I almost skipped upstairs to see what mysteries were ahead. Mom held a finger to her lips, cautioning me to be quiet, she said that this floor was off-limits to anyone without Uncle Tim's permission. I was in awe. The entire third floor was a suite with heavy oak furniture and bed, a hot tub that would easily hold ten and a walk-in sauna room. There was a closet that could park two cars and an exercise room. One room was just for computer equipment and video games. I noticed that closed-circuit cameras were strategically placed in most rooms. And a set of double doors at the end of the hall that were kept locked, mom dropped her eyes when she motioned towards them.

Then we proceeded to the top floor, a kind of attic that would have been considered a penthouse in many luxury apartments. She showed me rooms that would be for us, each with an attached bath. The view from this height was of the well-groomed grounds and surrounding woods and fences. Even the cabinets and drawers looked too highly polished to touch, without gloves. I wouldn't even sit on the big, twin beds until I'd showered. It was all girls' dream, if only it could stay that way. I was surprised to hear the crackle of an intercom, and the pleasant voice of my uncle inviting us to join him for a late lunch downstairs after we had settled in. The interruption brought my fantasies back to reality. This place has eyes and ears. We both eyed each other and took a deep breath as if anticipating a cliff dive into shallow waters. I also still had not figured out if we were all in this together or if it was every man (so to speak,) for himself.

We proceeded down the steps, anxious and wary both. I hadn't seen him in a few years. I was still wearing braces then, (that he had paid for,) and was surprised to see him looking so young and fit. He had the family's dark hair and brown eyes. He wore a devilish smile as he seemed to be appraising me while complimenting my mother on her child-rearing skills. He was well past six feet tall and muscular on a 210-pound frame. Tim was cleanshaven but the dark trace of whiskers would always be there. He had broad shoulders and a trim waist with thick, athletic arms. I felt odd in finding my uncle to be sensually handsome but the air was thick with libidinous, erotic anticipation. His dark, unflinching eyes could look right through you.

I was wearing a calf-length, black, pleated skirt that emphasized my long, shapely legs with four-inch stiletto heels. When dressing this morning, I worried that the outfit looked a bit slutty but then I was reminded of the nature of this arrangement. Women are often insulted when they see hookers or porn actresses dressed in revealing or suggestive attire, but when you consider that the object of the exercise is to attract a man sexually, why would you wear a burka? I also chose a low-necked, form-fitting, pink sleeveless blouse with a figure-enhancing red bra underneath. My lips and nails were also accented in a warm shade of red, and my long hair was brushed to a glossy shine and laid enticingly over the sculpted cups of my tight bra.

I wasn't actually intending to "capture" my uncle, but I did want to make a memorable impression, afterall, I reasoned that this is my new boss and possibly a meal-ticket. The illicit taboo thoughts had already been placed in my mind, I just needed to adjust to them.

Mom was wearing sleek, black pants that hugged her curvy ass and heels that kept her nearly my height. And she topped the look with a sexy, silk shirt that she wore unbuttoned down to her bodacious cleavage. She had a dangling, silver necklace with a pendant that disappeared into the deep crevice between her plump tits. Even my eyes bugged-out when I first saw her hefty melons squeezed tight and defying gravity every time she bent at the waist. Her hair was nicely styled and newly touched-up and laid gently on her shoulders. For the first time, I noticed the unmistakable similarity in our characteristics, other than me being slightly taller.

I was surprised that Uncle Tim had brought fried chicken and all the fixings, I didn't think that rich people ate with their hands and used paper napkins. But he was very pleasant, even opening a six-pack of beer and asking my mom if she thought I was old enough to indulge. He offered a comical toast and said that we should relax and enjoy ourselves on the first afternoon, and then he casually enquired about our general well-being and we all asked obvious questions that most family members don't find the need for. We sat comfortably in the casual kitchen as we got reacquainted. There were some laughs and a few tears, but a certain tenseness lingered in the air.

When the meal was finished and cleared, we each had another beer and moved to some nearby couches. Mom and I sat together on one while Tim sat across from us. He seemed easy and relaxed while I felt the tension of a job interview. There were never any probing questions and the smile never left Tim's face, infact he offered helpful suggestions and implied that though we would have work to do, we continued to be family and we should feel right at home now. However, there were also moments when the pleasant conversation hit a lull, they weren't long or embarrassing but I sensed an uneasy, and unspoken examination or interrogation being conducted. It was like each of us had a secret that they wanted to remain hidden while looking for any vulnerable and telltale twitch in the other, that would give you an edge. The Victorian setting, the enigmatic players and the exotic, illicit subplot of the entire affair was like living in a giant game of "Clue."

Enjoyed this story?

Rate it and discover more like it

You Might Also Like