The Babysitter 50

I didn't need a "babysitter," since I was 18, but my father thought that I would throw parties and trash the house if I was left alone while he went on his honeymoon cruise with his new trophy wife. The sitter they chose was my new step-mom's best friend, Octavia, a bitchy overweight woman of fifty, the type who wore too much make-up and drank in the middle of the day. She actually volunteered for the job, saying that she would make sure to keep me under control. I dreaded spending any time with her, but my protests fell on deaf ears.

The first day, she laid out her rules for me. I couldn't leave the house after dinner! She was responsible for me and didn't want me to get some bimbo pregnant under her watch. There were other, equally stupid rules. I couldn't close the door to my bedroom or the bathroom, since she didn't want me masturbating. I couldn't use the computer outside her presence, so internet porn was out of the question. I must have been rolling my eyes because she suddenly stopped and asked me, harshly, whether she needed to write the rules down for me. I answered sarcastically that she should write them all down so that I could study them and be her obedient slave. She slapped me hard across the face; it was hard to believe a five-foot-two woman could muster that much power.

"You won't speak to me like that," she barked. Her look, though, was more cold than angry. I didn't really know what she was a capable of, so I decided I better pretend to go along with her rules until I figured out what to do about the situation.

"Your punishment will immediate and severe. You will not test me. I demand absolute obedience." I thought for a moment. With so many rules, though, I was likely to slip up sooner or later, and how bad could it be, really? I wasn't afraid of her spanking my bare bottom. She probably wouldn't do that anyway, risking the wrath of my parents. My plan was to test the waters first with a minor infraction: then I would know what I could get away with. I learned, in the next few days, that being late to dinner earned me an icy stare and a warning, a sarcastic tone resulted in a hard pinch to the both cheeks. I figured I could stand four weeks of her petty tyranny.

Octavia's only apparent hobby was making up her face. She spent hours in front of the mirror every morning, and I never saw her without a full coat of her "war paint." She reapplied her lipstick constantly throughout the day. Her long, painted fingernails could do real damage, as I had already learned. She even had her own ridiculous YouTube channel devoted to cosmetics for the "mature woman": what a vain and superficial broad, a thoroughly horrible person! If she was that vain, then why didn't she lose her forty extra pounds!

I tried to confuse her by obeying her respectfully one day, and then being a bit insolent the next, but without going too much over the line. Sometimes I would react to her slaps and taunts stoically; other times I would pretend to be upset and run to weep disconsolately in my room. I had to make sure that my reactions never fell into a predictable pattern. Her treatment of me didn't differ too much from day to day, though: I had a choice between an ice-princess and a raging maniac. When I had been particularly good, she gave me gentle kiss on the cheek, leaving a lipstick print that she said I was not allowed to wash off. That was the extent of her kindness to me.

Finally, something had to break. After a week of this stand-off, I tested her limits on purpose. When she left the house to go the supermarket, I went to the master bedroom--which she had taken for herself instead of the guest room, where she should have been staying--and found a pair of her panties from her suitcase. They were frilly, not exactly what I had expected. I turned on some BBW MILF porn on the internet and jerked off into her underwear. I wasn't even going to hide my tracks, so I left her computer on, with "pornhub.com" open in the browser. Weirdly, images of Octavia's never-ending lipstick teases and long red fingernails jumped into my head and made me climax within a few minutes. I realized that I wanted to feel her fingernails as she spanked my bare bottom. I wanted to make out with those luscious lips and then have her fuck my brains out. I threw the panties in the hamper, not even bothering to hide them. When she found them with my jism in them she would be enraged and I would gladly take my punishment. As she spanked me she would realize that I was enjoying it, that I myself had set this plan in motion.

Or maybe her whole domineering act was a way to seduce me? Either way, I didn't think this story would badly for me. The worst thing that could happen was that I wouldn't get to take Octavia to bed.

The next few days were tense. Obviously, she knew right away what I had done, but instead of punishing me immediately, in a fit of rage, she was planning her perfect humiliation. After expressing fake concern for my mental health, and calling me a "dirty, depraved boy" in the next breath. She asked me what I thought my punishment should be, and I came up with a few lame suggestions, like being grounded--I wasn't going anywhere anyway so it made no difference. "Oh, forget it, just lower your pants and take your spanking," she said. I pretended to be surprised and shocked, but I obeyed. I bent over and put my hands on the dining room table and she hit my bare butt repeatedly with her open hand. She kept going until she caught glimpse of my raging hard-on and brusquely ordered me to pull my pants up again.

The next time I jerked off into a pair of Octavia's panties, I made sure I did it while watching her own YouTube channel--and made sure she knew it too. At this point, another spanking was pointless. After a few more days, she sat me down again and said that I had been a big disappointment. She had tried to instill some discipline in me, "for you own sake," she said, but I was a worthless, dirty-minded piece of shit.

The next morning, I awoke and realized I was naked and tied to the bed in the guest room. I heard women's voices from other parts of the house, at least two or three. I waited for what seemed forever and Octavia came in. "I bet you thought that spanking was your punishment, but I have something different planned for you."

She started with my ear, blowing into it, then nibbling on it gently, then thrusting her tongue into it aggressively. She licked my neck, then began to work on the rest of my face. I pretended to feel disgusted, at first, squirming a bit, but then I gave in to the experience. If I turned my head away from her, there was another woman on the other side who would start licking my face. She was a seventy-year old woman who looked like she followed the dubious make-up advice from Octavia's YouTube channel. For the next hour, I felt three or four tongues and multiple hands all over my body, on my nipples, my butt, and my abs. While Octavia thrust her tongue into my mouth, I felt another two mouths on my cock. I came quickly the first time, but after a few minutes they would start again. Each time, I took a little longer to cum, until finally, after five or six orgasms, I was left alone and fell into a deep sleep. I awoke in the late afternoon, no longer restrained, and jumped into the shower.

The next morning, at breakfast, she said "I hope you learned your lesson, young man." "I just have one question for you, I responded, "When can we do that again?"

"When did you figure out my plan for you?" Either one of us could have spoken these words, but in this case, she was the first to pose the question. "Your dominatrix persona was exaggerated from the start. Nobody is as bitchy as you were pretending to be. Anyway, I felt I had nothing to lose by playing along. Whether I was obedient or rebellious, the end result was going to be the same. Anything I did to entice you into punishing me just made it better for me in the end. The only way you could have made me suffer was by ignoring me and not taking the bait."

"When did you realize I was on to you?"

"I guess it was when you deliberately defiled my panties. I thought that you were intimidated, but at that point I realized that you had absolutely no fear. If you could commit so brazen an act, wanting to be caught, I knew my threats were idle. Your new stepmother has been monitoring your internet porn activity for a few months, and she told me about your submissiveness and your fantasies about taken by an overweight older woman, so I knew you would eventually fall into my trap. As you say, if you were rebellious, I could punish you, if you were docile, I could simply dominate you, so either way, we end up in the sack together."

Luckily, I had two more blissful weeks with Octavia before my father and his new bimbo bride came back. Since I had won the battle of wills, I moved in to the master bedroom with her, without asking permission, taking the dominant role in our relationship from that point forward. I did enjoy it, though, when she dug her fingernails into my back when I was drilling her. She could slap or spank me, tease me with her red lipstick, or verbally demean me, but in the bedroom, she would submit to my desires.

When my dad and stepmom came back, I did not, of course, tell them of any conflict I had had with Octavia. I just said we had gotten along marvelously (this was half true!). My dad was skeptical, because I'm sure he had heard that most people thought she was a nasty piece of work. Even my stepmother, supposedly her best friend, knew she could be short-tempered. "Sure, she chewed me out few times," I said, "but I probably deserved it." Octavia seemed embarrassed by this exchange and did not say a word.

At this point, I had only one aim: to make sure that Octavia would be my sitter when my father took his next trip. I would do or say anything to make that happen.