tagBDSMBabysitter's Education Ch. 02

Babysitter's Education Ch. 02


Renee was gone before I had a chance to really enjoy the Sybian or ask her any questions. It was clear she intended to sexually torture me again tonight, although if her promise that power level 3 and maybe level 2 would make me cum, my experience would be different and much more exciting from yesterday. I started doing the math in my head. If I managed to stay in this position until she got back, I would cum two to four times per hour. Even if she came home early, that meant I had four hours riding the ultimate orgasm machine as I saw it called online. I could expect eight to sixteen orgasms... assuming she came home early. Another six were not out of the question if she stayed out late. I put that thought out of my head. She could never resist me knowing I was in her playroom and at her mercy. I was surprised she could leave at all.

My basic night went like this... the five minute slow speed was tantalizing and kept my lust simmering. Then watching my video for five minutes while the Sybian rested kept my libido steady. Then the medium speed would kick in. It was at this time I realized the little finger attached to the seat and inserted into my pussy would hit my g-spot on a regular basis. I closed my eyes and just rode the feeling. It got me close, but I didn't cum during the first cycle. When the Sybian stopped, I opened my eyes and my body relaxed. I was pretty confident that once I had my first orgasm, speed two would be strong enough to get me off, especially if I could keep the little finger in just the right spot. I knelt in anticipation waiting for the full speed mode to kick in. I was now pretty confident that Renee had set me up to orgasm in the double digits tonight. If true, that was a fine reward for me being a good girl indeed. I was watching myself on the TV, but I really wasn't focused on the show I was putting on there. I didn't know how far Carter lived from Renee, but I hoped she would get there in time for them to web into the feed from the security camera and watch when level three hit.

Were they watching? I don't know. If they were they didn't talk to me. But as soon as level three started, I was out of my mind. Yes the Sybian is probably the most expensive vibrator on the planet, but damn, it is worth every penny. Especially when you are bound and forced to ride it. If you have the opportunity to experience one, do it.

I welcomed the five-minute break to allow my body to calm down after my first orgasm. As before, the next five minutes on the slow speed did little but to warm me up for the anticipated level two assault to come. I was certainly pleasurable, but my mind was already preparing itself for the intensity of the next two rounds. As I prophesied, I did come on the next session with level two. It was right near the end and was a nice, happy orgasm. My body was not out of control, but I knew that was coming soon and probably on the next set of level three. I was getting to the point in the video where I questioned whether I squirted last night. Before then I knew I never had and I wasn't sure if I had last night or whether I was just wetter than I ever had been before. Just as the video started showing that part of my pervious performance, level three kicked in and I could no longer concentrate on the TV. Or the camera. Or anything else but the incredible buzzing on my clit and more importantly on my g-spot.

The Sybian's nub was dancing inside of me giving me a rapidly growing level of arousal unlike anything I had experienced. Had I been more turned on when Mistress fucked me into submission with her strap-on last night? Yes, I'm sure I was. But this experience, while different, was amazing as well. I'd never gone from relaxed but with anticipation to holy shit I'm going to cum so quickly. I'd watched Renee endure this having been ordered not to cum and I don't see how she could have done it. Right on the heels of my brain signaling a big orgasm was building and a freight train was coming down the tracks, I had an intense feeling like I had to pee. There was nothing I could do but ride the wave and when my orgasm crashed over me, I began to squirt.

If I had doubts last night, there were no doubts tonight as my cum sprayed out of my pussy and into the air. It destroyed me and left me hanging by my wrists from the cuffs as the sixth cycle finished up and the Sybian turned off. My chest was heaving and I gasped for air. I felt nothing below my waist. I was numb with pleasure. My head was still hanging low with my hair covering my face when I finally began to recover and join the living. It must have taken me the full five minutes to recuperate as the low buzz of the Sybian returned just as I raised my head and smiled a weak smile toward the camera. I hoped Mistress had seen that.

For those keeping score at home, that was three orgasms, including a soul-crunching squirter, in the first hour. While I was thankful for all three, I began to worry again about how I would survive three to five more hours. Sure I could quit any time, but I wanted to prove my worth to Mistress Renee and show I could handle anything she could dish out. But as the next low-level vibration period drew to a close, I had a new probably. Even that level almost brought me off. My body was becoming much more sensitive to stimulation. In any other environment, that would be a good thing, but here it meant I came again only two minutes into the medium speed time. That also meant I was close to coming again when it turned off. I cursed the timer. I am sure it will not surprise you that I did cum three times when it was turned back on high including another squirter on the third high speed round. And the fourth. My body had now decided the slow speed was enough to edge, the medium could get me off twice and the high speed three times. And I didn't want anything to change.

After four hours, the Sybian did shut down. I had remained kneeling on it the entire time. I was a sweaty, cum soaked, mess. I didn't squirt every time the high speed cycle came on, but if my memory served, I did four times and I felt dehydrated. After about ten minutes, it was obvious the torturous device wasn't going to start another cycle. I was very tempted to release myself and get some water to drink. I even went so far as to pull unhook my cuffs from the chain in anticipation of doing so. But when I began to stand up, both my legs were asleep and I ended up slumping forward. My face was on the floor, supported by my hands as a pillow, but I was still sitting on the Sybian and in that is the position I fell asleep. That was also the position my Mistress found me in a couple hours later. I woke to the slap of her hand on my ass.

"It looks like you had a fun night, my little tramp," she exclaimed. "At least half your body could follow instructions."

It took me a moment to focus on my Mistress. She looked like I felt. I think Carter rode her hard and sent her home wet. I managed a weak smile but didn't vocalize any words. It was pretty obvious how both our nights went. We ended up in her bed again and again she possessively spooned me. In the morning she again sent me to prepare breakfast while she showered. This time I was naked. I loved serving her in this way. She returned to the kitchen looking fresh while I was still walk of shame nasty. Again she allowed me to sit on her lap and again she brought me off while I was eating. I could get accustomed to that kind of breakfast. After I came she told me to shower and dress. I watched as she began to eat. I didn't like being separated from her, but I needed to wash. By the time I returned the kitchen was spotless. Mistress Renee told me to go home and that she would clean up my mess in the playroom. I volunteer to help, but she declined. That was a disappointment. But what could I do? I went home.

Monday morning Renee texted me a list of clothes to wear. They were not trashy at all and were perfectly normal for a student in class. I was kind of disappointed. Renee also treated me perfectly normal in class. I knew we were keeping our relationship on the down low, but a wink or secret nod acknowledging I was now her property would have been nice.

Tuesday she again dressed me. This time she had me wear a skirt too short to be appropriate in class. But since I didn't have her class I guess she thought it would be fun. I sent her a selfie aimed under my desk so she could see my legs as proof I had done it. That night when I went to bed, she called me and we ended up having phone sex. I masturbated while my legs were spread with my feet facing the corners of my bed in my new favorite position. We every sweet, nasty word she spoke into my ear, I became more aroused and I loved her just a little bit more. Thursday night was similar only instead of Renee speaking into my ear driving me crazy, she let me do the talking about my fantasies as we both rubbed ourselves to very satisfying climaxes.

Friday I was once again ordered to wear my shortest skirt. But this time Renee instructed me not to wear panties and to sit in the front row of her lecture hall. My heart started beating faster as I dressed and I was very turned on by the time I sat down in front of her. She didn't have to tell me that I wasn't allowed to cross my legs. I was sure she wanted me to sit there with them spread as far as the skirt would allow and flash her my needy pussy. I don't remember much of her lecture because I was thinking more about kneeling under her desk and eating out her pussy. But that would have to wait until I arrived to babysit that night.

For the remaining couple of months of the semester until Summer break that is pretty much how our relationship went. Renee told me what to wear to school each day. Progressively I started dressing sexier and sexier. She sent me links to an online lingerie store and we bought far too many racy undergarments for me. Even on the days where she had me dress down, I would be wearing something sexy under my clothes to remind me of my status. I loved it.

We had phone sex once or twice a week depending on how Renee felt. I was up for it every night because I thought it was a great presleep activity, but she always kept me guessing as to whether she would call. On the nights I babysat, I always got there early enough to eat her pussy while she got ready and also had to do it when she got home. We never did repeat the two sleep over nights, although I volunteered to stay every time I was there. Renee thought it was better that I wasn't there when her son woke up. I couldn't argue, although I was disappointed.

As for my pleasure, I usually had some form of self-bondage and teasing to make my night interesting after her son went to sleep. He did almost bust me once as he woke up to go to the bathroom. Sometimes Renee would get me off when she came home (always after she came first) and sometimes I would be sent home unfulfilled. I was really looking forward to summer break because I figured it would mean more playtimes and it did. But summer was also a time for a summer job and I got one I did not plan for or expect.

School let out for the summer on a Friday. It was a weekend when Renee didn't have her son so I didn't expect to see her because she would be with Carter. But Friday night she called me and told me to be at her house at 9am sharp ready to work. I was giddy until she mentioned something about spring-cleaning and I pictured myself scrubbing the kitchen in my maid's outfit. Needless to say I was right on time and yes I was immediately instructed to put on the costume. But I didn't clean the house. I spent the day pleasuring Mistress Renee and she spent the day extending her dominance over me. That night she told me she was going to have some friends over and that she expected me to me my usual charming self. I noted that she didn't say she was going to share me with them, but I anticipated that is what she meant by my being charming. I wondered if Carter would be one of her guests. Given what I knew about him, I definitely figured Renee might share me with him. But as usual, I was wrong.

Early in the evening we both dressed for the party. I for one was glad the party was here as I was only dressed in lingerie. I thought I looked great, but I definitely didn't want to go out. I was dressed in white, betraying my lack of innocence. I had on a lacy bustier, a g-string that left little to the imagination and was already beginning to soak through, stay up white stockings and white stilettos. Honestly I can't understand how Mistress Renee could resist throwing me on the bed and fucking me with her strap-on. I hoped she planned that for later.

By contrast, she was dressed all in black, as befitting a Mistress, and in leather instead of lace. She was wearing a corset, a thong (at least she had a little more modesty than I did) fishnet stockings and leather bitch boots that came up to her mid thigh and had a four-inch heel. She was intimidating but also looked mouth watering. Looking at us as a couple, there was no doubt as to our respective roles.

She told me my job that night was to keep the drinks and snacks flowing to her guests. I would have help at times, but it was my responsibility to make sure she was seen as a good host. Again I took that to mean sexually. When I was not serving others, I was to kneel by her side. She had already taught me that position and we had been using it for a couple of months so I wasn't sure why she felt the need to reinforce that rule, but so be it.

There were three couples that arrived shortly after 8 that night. All three were lifestyle couples. Two were male Doms with female slaves and one was a female Mistress who arrived with two male slaves. Both the men were wearing collars and the woman was holding chain leashes attached to them. She was exceptionally beautiful and her slaves were very muscular and athletic. The other two couples were older men with younger, college aged girls. I theorized they had daddy fetishes or were sugar babies. But everyone seemed nice and after introductions I began taking drink orders. The Mistress instructed her two slaves to help me in the kitchen. They were friendly enough, although neither sounded as tough as their physiques would dictate. I suppose that is why they were subs, I silently chuckled to myself. That didn't stop me from imagining them bending me over the counter and having their way with me. Although it had been months since I had a real cock (Mistress Renee's strap-on was plenty for me) I wasn't beyond looking at a hunk of meat and wondering how they would handle a hellcat like me. But I digress.

The party, other than the obvious proclivities of those in attendance, was perfectly normal. That is to say, nothing kinky was happening and conversation was fairly vanilla for the first hour. Then as the drinks had been flowing a bit, conversation between the dominants began to take a more sexual tone as they began to "talk shop" and as Renee started talking about spanking I had the feeling that I might soon be called upon as a demonstration model. They older guys were fairly good looking, but I must admit I would have loved for Renee to offer me to the other Mistress to be put over her lap. Then again, since her slaves were male, I wasn't sure if she would want to punish me.

But alas, Renee was not ready to share me that night. The purpose of the party was a collaring ceremony, as both of the older men wanted to officially collar their young slaves. It was interesting to watch. Both girls were obviously thrilled and both gave their new official masters head after their collars were locked on. I was jealous. I had not known about collaring ceremonies until that moment, but I wondered why Renee had not chosen to collar me. Later after everyone had left, I asked her for permission to ask a question and then asked her why she had not made it official that I belonged to her. I was confused because I had worn collars during our play, but apparently play was all I meant to her. She told me that because she was a switch, she felt weird about collaring me and that she loved me very much and hoped I would remain her perfect little slave girl. Our dynamic seemed different after that. I knew she was submissive to Carter, but I didn't know if he had collared her and I didn't see why that meant she couldn't collar her own slave too.

We got to play on Sunday too. I was still a bit upset over not being collared, but Mistress Renee still delighted in binding, teasing and spanking me so it turned out to be a pretty good day. As I was dressing to leave she gave me a piece of paper with a name and an address on it. When I asked what it was, she told me she had arranged an interview for me for an internship at a law firm. The firm's name was Lehr, Hillman and Jenner. I told her I had never heard of them.

"It's a small firm," Renee told me. "They handled my divorce. Just three partners and they all specialize in different things. Hillman does divorces, Lehr does real estate and Jenner does tax issues. They need a research assistant for the summer, maybe longer and it would be a great learning experience. You need to be there at 11am tomorrow morning. Don't be late."

"I'm not sure I want to be an intern," I countered. "They get paid shit and get dumped on for work."

"Nonsense," Renee replied. "You need a summer job and this will pay better than retail. Plus it is not a stuck up law firm and will look good on your application when you finish up Community in a year and want to transfer somewhere."

That did make sense to me so I agreed to at least go and talk to them about the position and get some interview experience if nothing else. Renee dressed me very professionally for the interview. She explained that even though it was an intern position, you should always dress like you are applying to be CEO. She did allow me to wear three-inch heels instead of my usual four-inch because she didn't want to risk having me fall down, although hidden from view I did have on some sexy and lacy lingerie. "Even though you are a professional," Renee explained, "you are still a woman and should always remember that."

I got to the office early so I would be sure I was on time. I sat in the car for about 15 minutes with the AC blowing full power to keep me cool. I was nervous and started to panic a bit, but five minutes early I summoned up my courage and walked into the office. Although Renee had said they were not stuffy, the lobby was very formal and the receptionist was very formal. I suppose she had to make a good first impression for the firm and she certainly did that. I told her I was here for an intern interview and she said I was expected. She gave me an application to fill out and said Mr. Lehr would be with me as soon as his meeting was over. I started to relax as I filled out the form. Having a task always helped me. It took about 10 minutes to do the paperwork and then another five for Mr. Lehr to walk into the lobby and greet me. He was an older man (at least to me) probably in his mid forties. I pictured him as not exactly handsome, but not bad either. Kind of middle of the road. But I wasn't there looking for a date, so it didn't really matter. He was the firm's real estate lawyer.

The interview itself went fine, by my estimation. He made the position sound interesting. The money wasn't great, but for an internship at least it was paid. My expenses at home are not too much so I could save most of the pay for school next year. I was OK with that. The hours were pretty standard 8 to 5, although if they had a big case he did warn me that overtime might be necessary. As long as it wasn't on a Friday night when I was babysitting some OT wasn't a problem. Our interview lasted about 20 minutes and then he passed me off to Mr. Jenner. He was about the same age and attractiveness. He was the tax specialist and I could tell his mind was razor sharp. I felt like I had screwed up a couple answers with him and he was more specific in his questioning than Mr. Lehr had been. I made a mental note about their contrasting interview styles and took mental notes of how to approach future interviews. Again we went about 20 minutes or so. Then he said he would hand me over to Ms. Hillman.

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byTappy_McWidestance© 3 comments/ 34043 views/ 15 favorites

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