tagMatureThe Proposition

The Proposition


Please respond! This is my first submission and I would love feedback, positive and negative, so long as it is constructive. Thank you for reading my submission.


I doubt I was unique in any way. Finishing up my senior year of high school, just turned 18. Not a smashing success with the ladies, although pride compels me to admit that I have had my fair share of attractive girlfriends. Attractive, but without that perfect body girls seem to be clamoring for these days. And, of course, something about older women has always turned me on.

It could be that they are so experienced, and so confident, it could be that their maturity ensures that I do not have to worry about taking control of events, or it could just be my appreciation for a mature feminine figure. Whatever it is, I know I am not alone in being a teenage boy lusting after older women. However, whenever I would fantasize about them, the control they took always extended far beyond the normal boundaries of the confident older woman, or even the aggressive older woman. I realized soon that what I wanted, needed, was a dominating older woman. This is the story of how I found one.

"Jack, school is starting in fifteen minutes" my mother called from downstairs. I was usually late for first period, but my teacher was on vacation and the substitute didn't care. Anyways, I could only get away with being late if I arrived before roll was called, so I figured I had better hurry up anyways. Soon enough, I was out the door with a muffin, listening to my mom yell for me not to go anywhere after school. Usually she wouldn't have cared, but with the huge snowstorm predicted for tonight she obviously wanted me home as soon as possible. I doubted it would strike early enough to make haste home necessary, but an overprotective attitude is a common failure in most mothers I tend to forgive.

During first period (I was late but as predicted, the sub didn't care) I began to chat with Aaron. Aaron and I used to be pretty good friends, but sometime in high school he just stopped caring about stuff. I was always a highly motivated student, not quite a geek or a nerd, although definitely not the sporty type, so his seemly sudden lack of motivation was the beginning of the end of our friendship. It was never bitter though, we just drifted apart. I suppose you could call him a loser, if you like the term. He certainly was never very popular. In any case, he began to relay a message from his mother.

"Yea, I dunno why, but my mom says she just found something you left at our house years ago. Says she wants you to stop by after school to pick it up." Although we used to be good friends, and I am sure I had left plenty of toys over at his house when I was much younger, I couldn't imagine anything that has gone missing for so long that I would still care about.

"Alright," I said, "you want a ride home if I'm driving there anyways?"

"Naw, thanks though. I'm with my dad tonight."

Aaron's parents had divorced when he was in second grade. It was pretty messy, and I think it might have been the reason he became so nihilistic.

The bell rang then, cutting our conversation short. But he had given me the message from his mother, which was all he really needed to do in the first place.

Later that day, after school, I drove over to Aaron's house. Aaron's mom, Shelly, had remained friends with my mom despite the lack of communication between Aaron and myself. I had never really gotten along with Shelly, but there was no open hostility. We were on speaking terms, I just didn't like her quite as much as I like some of my other friends' parents. As far as MILFs go, Shelly certainly wasn't one. Whenever my friends and I would discuss the hotness of various moms, she never came up as a contender. Even so, I had always been attracted to her. Her figure was nothing special, she wasn't fat by any means but she wasn't exactly 21 either. In fact, she was in her late forties, and she looked it. But despite this, I had always harbored a bit of a fantasy about her. Whenever I would fantasize about a friend's mom, she was the only one I fantasized about.

So when I rang her doorbell, I was not surprised her greeting was friendly, if not warm.

"Just one second Jack, I'll have it in a second" she said. "Aaron must have asked you to come by and pick this up, thanks for saving me a trip." It turned out that it was not something of mine that she had found, but an earring of my mothers. She asked me to come in out of the cold, and I gratefully accepted. As I sat down, she told me that she must have left it in her car, and she ran out to grab it. Fifteen minutes later, she returned with the earring.

"I know it took a while" she apologized, "but it slipped under the seat." I told her that I had to be going, because of the approaching snowstorm, and she told me not to keep my mother waiting. However, when I went to turn on my car, the ignition wouldn't start. I went back in, and she told me she would call Aamco. As we sat, making idle small talk, the snow began to fall. Soon enough, it was more than just a dusting on the road, and I thought that even if they came and fixed my car, there might be too much snow to drive home. Evidently Shelly was thinking the same thing because she left the room to call Aamco again. When she came back, she was livid.

"They said that the snow was too deep for them to come! As if I didn't call earlier when there was no snow at all." I looked out the window, and realized that indeed, the snow was doubtlessly too deep for me to drive home. I decided my mother would be freaking out right about now.

"I feel awful that this happened" Shelly began. "I guess that you are going to have to spend the night, that should at least ease the worry on your mother's mind." I called my mother to tell her, and she was predictably irritated. But not quite as angry as I had thought she might be. In any case, it looked as if I would be spending the night, and much of the next day at Shelly's house, if not longer. There was definitely not going to be school the next day, and who could tell how deep the snow would get before it would stop falling.

I excused myself to use the bathroom, and Shelly said "use the one in my room, the guest bathroom is clogged right now. I should start making dinner anyways." As I sat on the toilet, my eye caught a magazine hidden behind a few others. All I could see of the title was the world "Adult." This certainly would not have been in the guest bathroom. The magazine turned out to be "Adult Toys: Bondage and Control." As I turned the pages, my pulse quickened and my cock started to lift. I had always been fascinated in this sort of bdsm thing, and I often have wondered what it would be like to have a mistress.

As I walked out into the living room, I hoped the bulge in my pants from reading the magazine was not noticed. I saw her eyes flick to my groin, and I thought the corners of her mouth lifted in a subtle smile, but a second later the smile was gone.

"I feel I must apologize for the meal, but I was only expecting to cook for one tonight, with Aaron at his father's house. It should be ready in around an hour." I told her that it was quite alright, and whatever she made would be fine.

We began to chat about school, work, and eventually the topic of girlfriends came around. I told her that I had had a few, but I was single right now. "An attractive young man like yourself, single?" she half-joked. "Half my friends would kill to have a young man such as you to play with. Their husbands would be thrilled for them to have one too." "Their husbands?" I asked. "Yep. Nothing kinky or homosexual or anything like that, they just are afraid of their wives cheating on them while they are out of town on business. Women can get pretty lonely. If their wife had a boy toy their husbands knew about, the wives would be happy because they would get sexual gratification, and the husbands would be happy because they knew that their wives were not cheating on them behind their backs, but just having meaningless sex with a young male with whom nothing substantial could ever occur." "You sound like you really thought this through" I joked. "Oh I have! But that is not even the best part. Get this: if the boy toy was paid by the husband for his services, the husband would feel even more in control of the situation. Even more than that, it would reinforce the idea that he is only a toy, a prostitute, not an active partner. If that was the scenario, nothing could ever occur that the husband would not approve of. Clever, huh?" I had to admit that it seemed logical enough. But then she really surprised me, for all that I should have seen it coming. "That is the business I am starting" she said.

"What?!" I replied, startled. "I already told you. A service designed to keep women happy and husbands confident while they are out of town." "Why are you telling me this?" I asked. "Anyways, wouldn't it be illegal?" She replied "yes, it would be very illegal, which is why it would be strictly black market, recommendation only. This would also keep it in my circle of reasonably affluent couples. As to why I am telling you, isn't it obvious? I want you to be my first boy toy."

I sat there speechless for at least 10 second. It scared me, but at the same time, I was getting excited. Very excited. This was my dream, my ultimate fantasy. To be the plaything of a mature woman, to be under her total control, to please her every sexual desire. To be a slut. A whore. I realized that I wanted to do this. She must have seen it on my face, for she grinned and told me the clincher. "You would get paid, of course." At this, my hopes, eyes, and something else perked up all at once. "How much?" I heard myself ask. "Fifty percent, straight up. Cash." She replied. "I don't know exactly how much that will be, because I have not yet set my prices, but I can assure you that if you save it, by the time you enter college it will be enough for all the spending money you could ever want for your four years. I am not saying that it will pay for college, not by any means. But it will definitely take the edge off of college life."

I was wondering at the miraculous coincidence that landed me in this situation. Right then I realized that it was no coincidence at all. She had asked me over to get the earrings knowing that there would be a huge snowstorm. She had not spent so long getting them out of her car because they were under the seat, as she said, but because she was sabotaging my car not to start. I wouldn't be surprised if she had had the earrings in her pocket the entire time. She probably never even called Aamco, and as for the magazine in her bathroom, she had doubtlessly sent me in there knowing I would read it and get turned on by it. She wouldn't have needed me horny to get me to agree to her idea, but she didn't know that, and it certainly didn't hurt. She has manipulated me the entire evening to get me in this situation, and it should have pissed me off. But I realized it didn't matter. In fact, I was glad she did it. I desperately wanted to be part of her idea, to be the toy of many older women. This was my dream, my fantasy.

So I agreed. She smiled and said she knew I would. I didn't doubt it. "Well, it is a good thing we have all night and part of tomorrow," she said," we will need to begin your training." "Training?" I asked. "Of course," she replied, "you can't expect me to allow you to go out to please women as you are. I need to teach you technique, to groom you to maximize your sexual appeal, and of course, to break down your inhibitions to the point that you will do anything, and I mean ANYTHING a woman asks of you. Still willing?" "Of course" I responded. "Good" she said. "Take off your clothes."

As I removed my shirt, she left the room to check on the meal. I heard her call "when I come back in, you had better be on your knees looking at the floor naked. If not, you will learn sooner than you wish what kind of punishment I offer for my disobedient toys." I was soon kneeling staring at the floor, my cock erect and pushing against my stomach. I was, of course, naked. She slowly walked in the room, even though she looked the same, had changed no clothing, she now radiated some sort of sexiness she had not had before. I soon realized that the source was her ultimate control over me. She began to outline her rules.

"First, I shall be addressed as Mistress. This applies unless I give you specific instruction not to. Also, it only applies when we are in business, or when I tell you it applies. For example, whenever you are receiving training or are present while I talk to a customer, you will address me as mistress. However, if we meet at the mall, or at your school, you needn't address me as mistress. If I should decide that I want you to call me mistress, I will tell you so, and you will obey no matter what the circumstance.

"Second, you will obey each and every one of my commands without question. You will have a safety word, 'mercy,' which you may use if things get too rough, but use it sparingly. I do not intend for this training to be painful, aside from punishment, so I doubt you will need it." At this, I let out a barely audible sigh of relief. The one thing I remained nervous about was any pain, which did not excite me nearly as much as the rest of the situation did. However, my Mistress's control over me though use of punishment did excite me, so I was content.

"Those are the only rules I require you to obey hard and fast. Address me as Mistress and obey me. The reason my rules seem so loose is that fundamentally, we are business partners, and although we are in no way equal, and although I believe I will enjoy being your mistress immensely, this is not a lifestyle for either of us. I do not require silence unless you are spoken to, and you may make minor mistakes without fear of punishment. I firmly believe that I can humiliate you without the needless rules which only complicate things anyways. And now, my toy, it is time to eat dinner. But first, I have something for you to wear."

And with those words she produced a simple leather dog coller. "You will wear this at all times while working. It is a symbol of your status as only a toy, only a pet. It will remind you that I own you, and I may do anything I like with you." She then put the collar around my neck, locking it with a small padlock. "The collar will be removed when you leave, and reattached when you come back for either business or training."

She then attached a leash to the collar, and led me into the kitchen. As I sat down, she looked at me, then glanced at the floor beside her chair. I didn't understand what she wanted, but when she took two plates, one of delicious looking steak and potatoes and the other of plain rice, and placed the rice on the floor, I understood. I slid too the floor, and kneeled in front of the plate of rice. She told me that I was not allowed to eat with my hands, and must eat like a dog. I buried my face in the rice, it was not as hard to eat that way as I thought it would be. I supposed the steak would have been harder to consume.

The rice was incredibly salty. Soon, I decided I needed a drink. She saw me looking around, and asked me what I was looking for. When I told her, she said "Of course, I cannot have my toy thirsty. Would you like something to drink?" As I nodded eagerly, she looked me straight in the eye, puller her skirt up and her white panties to one side. As I looked at her hairy pussy, I suddenly realized that she expected me to drink her piss. I hesitantly put my mouth against her pussy, and opened my lips. She sighed softly as she let a stream of yellow liquid flow into my mouth. I swallowed reflexively. It was salty, and warm, but I was not repulsed. I even enjoyed it somewhat.

Soon she pushed me into my back, sitting on my face, and I could not swallow all her piss. It ran out of my mouth and all over my face and chest, her sitting on my face all the while. I couldn't breath, I had to let all the piss into my mouth or suffocate. She then stood up and finished urinating, telling me to lick her clean. I did so, and noticed that she enjoyed it. I continued to lick her, even though I had long since cleaned her of all remaining urine. She moaned slowly, then started breathing faster. I pulled her clit in between my teeth and brushed it quickly with my tongue. She grabbed the back of my head and rammed my face into her pussy, crushing my head with her hands and thighs.

She threw her head back and screams "oh my god I'm cumming I'M FUCKING CUMMING FUCK IIIIIiiiiiiiii" she trailed off, panting heavily. She then rolled off of me, and her breathing slowed. "Well, my pet, it seems you can pleasure a woman orally. Your technique was lacking, but you more than made up for it in enthusiasm." I was crushed, I had thought from her screams that she was in ecstasy. She looked me up and down, and told me that the next thing she had to do was give me a shave.

"Nothing excites a mature woman with a boy toy more than a reminder of his young age and subservience. All your pubic hair, and the hair around your ass, needs to go." She led me into her bathroom, and sat me down on the toilet. As she rubbed shaving cream onto my cock and balls, I felt the beginnings of an orgasm being to grow. She started shaving, and it intensified. Soon, she finished, and I was about to orgasm. She then dumped a glass of cold water over my cock, rinsing off the remainder of the cream and killing my orgasm. I groaned and she grinned and said "we can't have you cumming so soon, my toy. There is so much more I have in store for you tonight." She had be bend over the toilet so she could shave my ass.

I looked in the mirror after she had finished, and saw my white cock and balls bare and gleaming. She slapped my ass, and I was startled to feel the lack of hair which I had grown accustomed to. The air felt cool on my newly shaved ass and cock, and I enjoyed the feeling of being bare for all who wished to see. Somehow, with the hair gone, I felt more naked, more vulnerable to the mature dominating women I would soon be prostituting myself to. I loved the feeling. I felt sexy.

As my Mistress led me into her bedroom, she told me to get in the bed and start playing with myself. She got out a camera and began to take pictures. "What are you doing?!" I asked. She got this dangerous look in her eyes, and said "excuse me?" I realized then that I broke one of her rules: never questioning her commands. She told me as much, explained that she was taking photographs for meetings with clients, and for her personal enjoyment, as was her right as my employer not to mention Mistress.

She then set up a video camera and told me that from now on everything we did would be caught on video. She made me lie across her lap, and told me to count off 20 strokes for disobedience. She slapped me once. Hard. It hurt. She slapped me again, and it hurt even more. The next time, I thought I could feel my ass starting to grow red. By the seventh, I thought I could feel my ass begin to glow red. I lost count after that, but soon the pain of each slap merged with a pleasure, both a mental ecstasy of submission to a dominant woman, and also a physical, sexual response to her abuse. By the time the twenty were up, I was harder than I had ever been in my life.

She then told me to lie front down on the stool for her arm chair. I did not see what she returned with from her dresser, but I heard her soft words. "This will hurt at first, especially because I just punished your ass for disobedience. If you feel the urge to resist, just remember that this will hurt even more if I have to punish you again before I ram this up your ass. And I guarantee, before the night is out, this will go up your ass."

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