Bedding the Babysitter

Brief Summary: Jenny fulfills an order from both of her Mistresses by completing the seduction of her teacher (a brief sub-plot in Bedding the Babysitter 3).

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

Note 2: A special thanks to all who have emailed 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.

A NEW EDIT HAPPENED IN APRIL 2018 WITH TEX BEETHOVEN.

Note 4: Although I recommend you read parts 1 through 3 first, here is a summary of this series so far...

Part 1-Megan, a dominant but caring lesbian, seduces her cute and innocent babysitter Jenny.

Part 2-Megan takes her new submissive lesbian for a makeover and then shopping where she arranges for a fantasy to come true with a cheerleader that Jenny has dreamed about forever before escorting her pet to an upscale lesbians-only club for an adventurous evening.

Part 3-A marathon week: Head Cheerleader Karen becomes Jenny's second Mistress, taking her under her wing at school as Jenny joins the cheerleader squad at school, thus springing instantly from nerd obscurity to eye-catching popularity. Karen orders Jenny to seduce their English teacher Miss Morgan and Jenny makes progress using writing assignments, subtle teases in class and anonymous online chats; even while Karen advances her own seduction of Jenny's mother. In a domination session with Mistress Megan, Karen is punished while Jenny is rewarded. To end the week, Jenny attends Cheerleader Camp where Assistant Head Cheerleader Sabrina is punished for disobedience to Karen and bullying Jenny, while Jenny and the other Assistant Head Cheerleader Ashley fall in love...maybe.

Bedding the Babysitter Ch. 04

SUNDAY FEBRUARY 9th: Impossible Mission Completed

As I had promised, I dressed in my cheerleader outfit and red thigh highs and headed to the Starbucks on Winter Street in Boston, arriving fifteen minutes early. I ordered my drink and bought one for Miss Morgan as well, then sat down at an open booth where I could spy Miss Morgan as soon as she arrived, if she did arrive. I waited nervously for ten minutes, fidgeting at my risky boldness. And at 11:28 Miss Morgan, dressed in a pretty but conservative blue dress and black pantyhose walked timidly in the door. She surveyed the room and froze, face aghast, when she caught sight of my own face, which to tell the truth was as scared as hers. She stood there for a few seconds before gathering her courage and joining me at the booth.

I forced a smile, hoping she wasn't going to hate me, handed her a coffee, and greeted, "Hi, Miss Morgan."

She sat down tentatively and accepted the drink from me, wrapping her hands around the cup to warm them from the frigid air outside. I could tell her mind was reeling, attempting to come to grips with the reality of the situation. I was her own student! Silence lingered between us. I waited for a word or something from her, my heart pounding.

Finally, in a whisper so soft I could barely make out her words she breathed, "I can't believe it's you, Jenny."

"Did you have no idea at all?" I asked cautiously.

"No, although based on our interactions during the past week, I guess it should have made sense," she said, still dazed. "H-h-how did you change so much, so quickly?"

I explained, "This may be hard to believe, but like I wrote in my assignments, 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 her desire for me was fighting an opposing team of both her conscience and her school reputation. She took a nervous sip of her coffee, "Who is your Mistress?"

I smiled, I was pretty sure I had her, she didn't run screaming out the door, which I'd been scared she might, "Well, my main Mistress is a next-door neighbour of mine, Mistress Megan." I paused, making sure she would be listening when I told her my other Mistress. I looked deep into her eyes and yes, she was staring back into mine, "My school Mistress, the one responsible for my sudden popularity is...."

"Karen Pepper," 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 while she coached me with your seduction."

"Oh my God," Miss Morgan gasped, "so Karen knows about this too?"

"Yes, it was all her idea even though I really like you and wanted to do it, but it's ok, Miss Morgan. Mistress Megan is Karen's Mistress too and she taught us there is one key rule to submission. Never, never ever, lick and tell."

Miss Morgan laughed in relief, but then caught herself. Her smile faded and a serious look replaced it. "This can't happen, Jenny. I'm your teacher."

My heart stopped! Well you know, figuratively, not medical. "If that's how you feel, Miss Morgan, I will respect that," I responded. "But before you reject me and walk out the door, please keep in mind that even if you do, I will never tell on you and neither will my Mistresses. And if you accept me, I will be your perfect little pet. You already know (I hope) that I always strive to do the best I can at everything I do." I slipped my foot out of my shoe and hidden under the table, slid my foot up my teacher's leg.

This startled her, but as I hoped, she didn't move it 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. But because you're a teacher, the important thing is we just do that ravishing where nobody can see and always be subtle in public."

A second gasp and a flush of red heat escaped Miss Morgan's face 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. Nobody can see me down there and I'll be quiet as a mouse."

"Oh Jenny," she said, flushed, "Stop that!"

"Am I making you wet?" I queried, teasingly. "Nobody can see that, either." She didn't answer as I slid up my foot a bit more, now under her dress.

"Please," she whispered.

"Please what?" I asked.

"Not here," she forced out, not wanting me to stop on the one hand, but scared on the other.

I reached into my purse and pulled out a printed piece of paper. I asked, confident I was right, "When you were chatting with me last Thursday night you said you couldn't stop thinking of a certain student. It was me, wasn't it?"

"Yes," Miss Morgan answered, but not making eye contact with me.

"And," I began before pausing for dramatic effect, "you said and I quote you," I looked down at the paper so I could read, "'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, you're right, I did say that, but it was roleplay and I had no idea I was talking to my actual student."

My foot moved to within an inch of her pussy. Inside I was confident I had won. "Doesn't matter, it was secret and nobody knows it was us, and I think even if you did know it was me you would have said it anyway and I'm really glad you did. Can we please go back to your place?"

When Miss Morgan didn't answer, I moved my foot all the way up so it was touching her panty-covered crotch.

To my great surprise and disappointment she blurted out, still real softly, "I, um, Jenny we can't, we just can't!" To my further surprise, she stood up and apologized, "I'm sorry, Jenny, I just can't do this." Before I could say anything at all, Miss Morgan hastily made her retreat.

After she left, I finished my coffee, contemplating what had gone wrong. After a week plus a bit of living a very charmed life, I guess I was bound to fail sometime. I texted Karen and told her of my epic failure. She didn't respond, so I finished my coffee and went to the bookstore, my personal solitude place whenever I was feeling down.

I went to the teen section and browsed the new titles. There's just something so exciting about holding a new book in your hand. Looking at the cover, reading the brief summary on the back or inside the book jacket, and reading how other authors are praising 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 horrible disease...love. It sounded interesting and different from other novels, plus I was definitely struggling with the word 'love' myself. I loved my time with Mistress Megan, I'd loved my one time at Le Chateau Club, I loved the attention I was getting at school now, I loved being submissive to Karen and I loved the thrill of the chase with Miss Morgan, even though I had failed.

But mostly, although I don't think I would label it love, or lust either, my feelings for Ashley were different from anything I'd ever felt before. I mean I had greatly enjoyed my newfound submissiveness and all that followed, but my time with Ashley was different. With her, 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 nonetheless 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 two days after a night of such naughty and yet romantic sex? Even though I was pretty confident she still felt the same way I did, I know she had yesterday anyway, but how does one ever 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. Could I give them up? Did I want to give them up? These questions spun in my head like a tilt-a-whirl until I thought I might get sick.

I grabbed a fruit smoothie and a muffin and sat down to read my new book and relax. I wasn't three pages in, when I heard a voice I knew. I glanced up from the novel I had just started and, sure enough, it was Miss Morgan ordering a drink too, a bag of books in her hand.

She hadn't seen me yet. I contemplated the odds of seeing her again an hour later. Concluding they weren't high, I took it as fate's way of giving me a second shot.

Once she received her drink, a fruit smoothie as well, she turned around and saw me. I joked nervously, "Fancy meeting a girl like you in a nice place like this."

She chuckled, also nervously. "Sorry for the hasty retreat earlier. I just needed time to think."

Realizing I might still have a chance, I sympathized, "I was surprised, but I think I can see how it was necessary.

Did

you have time to think?"

She scanned the room, looking for I don't know who or what, before sitting down beside me and taking a sip of her smoothie to give herself another few seconds to decide what to say to me. "Yes Jenny, I did," she prevaricated, not really giving me anything, but still here.

She seemed to be struggling for what to say next. "And?" I questioned, attempting to lead her on.

"I can't get you out of my mind," she confessed.

Inside I was giddy with excitement, but outside I played it cool, offering an olive branch, but not demanding anything like I wanted to, respecting her personal space. "The offer still stands, Miss Morgan."

She seemed to be attempting to process this when I decided,

bother her personal space

and to take a risk. I looked around briefly then grabbed her shoulders and kissed her; a quick, yet passionate three-second kiss. As expected, she didn't break it. Instead, I did and whispered into her ear, "I will be at the front of the mall in five minutes standing at the curb. If you want to take me up on my offer, stop by and pick me up. If you don't, I'll catch the bus and head home." I bit her ear gently and allowed my hot breath to linger. She gave just the softest of moans, all the evidence I needed to feel confident I'd gotten to her. Satisfied I'd enticed her but now forcing myself to leave the decision up to her, I stood up and walked quickly away. I was tempted to look back, but didn't.

I couldn't believe how excited and nervous I felt while I waited to see if my boldness had paid off! Two weeks ago I'd been too shy even to complain when my order was wrong at McDonald's. Now I had just propositioned my teacher. I checked the time every few seconds, hoping I'd enticed her enough.

Just as I was beginning to think I'd failed a second time, Miss Morgan pulled up. I suppressed my exuberant joy and just quietly got in the passenger side and she quickly sped off like she was the getaway driver in a bank robbery.

Once on the road, she said, "I can't believe we're going to do this."

I attempted to comfort her and convince her she was making the right decision. "Me neither, Miss Morgan. I've wanted this to happen for a long time."

"Really?" she asked, surprised.

"Miss Morgan, I began to think I might be a lesbian as soon as I started taking your class. I began dreaming about you, not just daydreams, real ones. I fantasized about kissing you, touching you, pleasing you. I just never thought you might be interested in someone nerdy like me."

"Oh my God, Jenny, I've had inappropriate thoughts about you all semester! Way before you began to dress so provocatively. I loved how cute, innocent and pure you looked," my teacher confessed.

Insecurity hit me. "Do you mean you like the old me more?"

"No, but the old you was more the real you, don't you think?"

This conversation was getting very real. I knew I had changed a lot this past week in all areas, but not once did I think it was a bad thing. Was I losing the real me?

Was

the old me even the real me? If not, who was the real me? These thoughts ricocheted around my head like a racquetball. I shared my sudden insecurities, "I don't know who the real me is anymore, Miss Morgan."

"Just do what

you

want to do Jenny. Don't do things for others' approval. You're a great young lady and have a bright future ahead of you."

Tears began to roll down my cheeks. It was so strange to have someone tell me to be myself, especially when I no longer knew who that was. Finally, I spoke the only truth I knew for sure. "Miss Morgan I'm still trying to

figure out

who I am. I don't know what I want to do next year, I don't know where I want to be next year, but I do know where I want to be right now." I put my hand on her knee and squeezed gently. "I think maybe I want to be in charge of my big decisions like schools and careers once I decide, and let wonderful people like you make the little intimate ones for me. Submitting to people I trust feels very right to me."

Her face turned red and her breathing changed just slightly. "Jenny, are you sure?"

"Miss Morgan, I'm unsure of many things in my life. But when it comes to this," I paused for another squeeze, "I have never been surer of anything in my life."

We arrived at her house and pulled straight into her garage without getting out. Once we were parked and the garage door shut behind us, Miss Morgan seemed to hesitate, unsure what to do next. I moved my hand under her dress. Her dreaded pantyhose blocked access to the pussy I now craved to sample. I leaned in and kissed her again, making sure she didn't have time for second thoughts. We were both about to invade each other's personal space most rudely, and that decision was now a done deal! My tongue parted her lips and, although tentative at first, Miss Morgan kissed me back. I pushed a finger hard against her covered crotch as we kissed. She moaned into my mouth, and we kissed for what seemed like an eternity. It was passionate, it was gentle. It was exactly how I had imagined it on so many nights while in my bed with just me and my dreams and my fingers. I felt a tingle down below and finally broke the kiss. I began to unbutton her blouse. She stopped me, attempting to catch her breath, "I want this too, but let's go inside, Jenny."

Reminding her of my ground rules...I didn't have any...I answered, "Yes, Mistress Morgan, I'll do anything you say."

She gave me a slightly startled look but didn't say anything as we got out of the car and she led me into her house. Once inside, we went straight to her bedroom and it was now Miss Morgan's turn to surprise me. She aggressively pushed me onto her bed and crawled on top of me. She leaned down to kiss me. Her lips barely touching mine, she kissed me ever so gently. She followed up on her soft pecks by sucking on my lower lip. I'd never been kissed like that and it was driving me crazy, making my pussy very damp. She moved down to my neck and gave it some soft nibbles and teasing sucks, spending enough time on each spot to potentially leave a hickey. Slowly she moved down my body and pulled me up so she could take off my shirt. "Oh, my," escaped her lips when she saw my tight white breasts, still bundled in my white lace bra.

I shivered slightly, suddenly cold and feeling like prey to my salivating teacher. She kissed the tops of my breasts while reaching behind to unbuckle my bra and release them. Once they were freed from their confines, Miss Morgan cupped them both in her hands and looked like a child in a candy store. She spent at least ten minutes adoring my hot breasts. She kissed, nibbled, and sucked on my nipples. Her tenderness and deliberate teasing had me on the edge of complete ecstasy, desperate to come soon. I whimpered, "Mistress, you're so good, please let me come."

She bit my nipple, not hard, but hard enough to make a statement. "Princess, just lay back and enjoy. I want to savour every minute of our time together." She bit my other nipple before sliding her tongue down my belly. I had never had someone use her tongue in my belly button, but the feeling was shockingly erotic. Maybe because it was so close to my pussy, maybe because I was so horny or maybe it was simply another erogenous zone in my overactive teenage body. Whichever way, when her head moved lower and under my cheerleader's skirt, I let out an excited moan.

Miss Morgan asked, "Is one of the orders you obey no underwear?"

"Yes, Mistress Morgan," I responded, my breath giving away my anticipated eagerness.

"Please call me Cameron, Princess."

"As in Cameron Diaz?" I had to ask.

"The one and only," she whispered, "don't you think I look like her?" her finger making just the slightest of contact with my pussy.

"Aaaaaah," I let out. "Yes actually, you really do and you're just as pretty, but I thought your first name was Wanda."

"That's my middle name. I can't have people guessing my real identity online."

"That makes sense," I whimpered again, struggling to talk sense with her finger teasing me so distractingly.