Bedding the Babysitter Ch 04

Bedding the Babysitter 4



Brief Summary: Jenny attempts to fulfill an order from one of her two Mistresses, when she meets with her unknowing teacher to finish a seduction she had slowly been doing all week (a brief sub-plot in Bedding the Babysitter 3).



Note 1: I recommend you read parts 1-3 to know the complete story of Jenny from shy, nervous in the
closet lesbian to submissive, sexy cheerleader and seductress. That said, you only need to read part 3 to learn the set-up of her seduction of her teacher that she completes in this chapter.

Note 2: A special thanks to all who have e-mailed me about Jenny and requested I continue the story.

Note 3: Last, but certainly not least, a special thank you goes to Steve B for his suggestions and Estragon for his copy edit.



BEDDING THE BABYSITTER 4

SUNDAY FEBRUARY 9th: Mission Completed

I dressed in my cheerleader outfit and red thigh highs and headed to Starbucks, getting there fifteen minutes early. I ordered my drink and bought one for Miss Morgan as well, and sat down at an open booth where I could see Miss Morgan when she arrived, if she arrived. I sat for ten minutes, fidgeting at my boldness. And at 11:28 Miss Morgan, dressed in a pretty, but conservative, blue dress and black pantyhose walked in the door. She surveyed the room and stopped, face aghast, when she saw me. She stood frozen for a few seconds before joining me at the booth.

I smiled, handed her a coffee, and greeted, “Hi, Miss Morgan”

She sat down tentatively and took the drink. I could tell her mind was reeling. She was clearly attempting to come to grips with the reality of the situation. Silence lingered between us. I waited for a response from her, my heart pounding.

Finally, in a whisper so soft I could barely make out her words, “I can’t believe it is you, Jenny.”

“Did you have no idea?” I asked.

“No, although based on the past week, I guess it makes sense,” she said, still dazed. “H-h-how did you change so much, so quickly?”

I explained, “This may be hard to believe, but I found a Mistress and she opened up a whole new world to me.”

Miss Morgan still looked completely out of her comfort zone. I could tell she was fighting her conscience. She took a nervous sip of her coffee, “Who is your Mistress?”

I smiled, I was pretty sure I had her, “Well my main Mistress is a neighbour of mine, Mistress Megan.” I paused, making sure she was listening when I announced my other Mistress. I looked deep into her eyes, “My school Mistress, the one responsible for my sudden popularity is….”

“Karen,” she whispered, putting two and two together.

“Yes,” I confirmed, “How did you know that?”

“Just thinking about the week and how odd you were acting and I recalled Karen’s smirks,” Miss Morgan reflected.

I agreed, “Yes, Mistress Karen has been giddy all week with the thought of your seduction.”

“Oh my God,” Miss Morgan gasped, “Karen knows about this too?”

“Yes, it was her idea, but it is ok, Miss Morgan. Mistress Megan is in control of Karen too and there is one key rule to submission. Never, ever, please and tell.”

Miss Morgan laughed and then caught herself. Her smile faded and a serious facade replaced it. “This can’t happen Jenny. I am your teacher.”

“If that is how you feel, Miss Morgan, I will respect that,” I responded. “But, before you reject me, keep in mind I will never tell. I will be your perfect little pet. You know that I always strive to do the best at everything I do.” I slipped my foot out of my shoe and allowed my foot to slide up my teacher’s leg.

This startled her, but as I hoped, she did not move away or ask me to stop. Instead, she asked, already wavering, “But what if someone finds out?”

“No one will, Miss Morgan,” I assured her, “Plus we are both consenting adults, free to ravish each other in any and every way imaginable.”

A second gasp and a flush of red escaped Miss Morgan while she tried to deal with her conflicting emotions.

Attempting to push the envelope, aggressive even for me, I offered, “If you wish me to show my true loyalty to you Miss Morgan, I will crawl under the table and please you right here, right now.”

“Oh Jenny,” she said, flushed, “Stop that.”

“Am I making you wet?” I queried, teasingly. She didn’t answer as I allowed my foot to slide up a bit more, now under her dress.

“Please,” she whispered.

“Please what?” I asked.

“Not here,” she got out.

I reached for my purse and pulled out a piece of paper. I asked, confident I was right, “When you were chatting with me the other day you said you couldn’t stop thinking of a certain student. It was me, wasn’t it?”

“Yes,” Miss Morgan answered, not making eye contact with me.

“And,” I began before pausing for dramatic effect, “you said and I quote you ‘I want to take you home and use you as my personal sex slave’”.

“Oh my God,” she blurted, looking up, “Did I really say that?”

I handed her the transcript of our chat. She reread the entire conversation before finally speaking. “Ok Jenny, I did say that, but it was role play and I had no idea I was talking to an actual student.”

My foot moved to within an inch of her pussy. Inside I was confident I had won. “Can we go back to your place?”

When Miss Morgan didn’t answer, I moved my foot so it was touching her panty-covered crotch. “I, um, we can’t, we just can’t.” To my surprise, she stood up and apologized, “Sorry, Jenny, I just can’t do this.” Before I could respond, Miss Morgan hastily made her retreat.

After she left, I finished my coffee, contemplating what went wrong. After a couple of weeks of living a very charmed life, I guess I was bound to fail. I texted Karen and told her of my epic failure. She didn’t immediately respond, so I finished my coffee and went to the bookstore, my personal solitude whenever I was feeling down.

I went to the teen section and browsed the new titles. There is just something so exciting about holding a book in your hand. Looking at the cover, reading the brief summary on the back or inside the book jacket, and reading other authors praise the book. I spent an hour browsing through title after title, making a list on my Ipod touch notebook of books that caught my interest. If I bought every book I wanted to read, I would never have any money. I finally settled on a novel called Delirium. It was about a time in the future, where when you turn eighteen you have an operation to prevent a disease…LOVE. It sounded interesting and different from other novels, plus I was definitely struggling with the word LOVE. I loved my time with Mistress Megan, I loved my one time at the Le Chateau Club, I loved the attention I got at school now, I loved being submissive to Karen and I loved the thrill of the chase with Miss Morgan, even if I did fail. But mostly, although I wouldn’t label it love, or lust either, my feelings for Ashley were different from anything I had ever felt before. I mean, I had greatly enjoyed my newfound submissiveness and all that followed, but my time with Ashley was different. I felt something more than just pleasure, something more than just the heat of the moment, something completely different and foreign. I couldn’t explain it, or quantify it, but none the less it was embedded deep in my heart. I wanted to call her, but really had no idea what to say. How do you attempt to have a normal conversation the day after such a night of naughty and yet romantic sex? Even though I was pretty confident she felt the same way I did, how does one know for sure? Especially under the circumstances we began our relationship, me a cheerleading sub and all. Not to mention, even if we did start a taboo lesbian relationship, I already had not one but two Mistresses.