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. Could I give that up? Did I want to give it up? These questions spun in my head like a tilt-a-wheel until I thought I might be sick.
I grabbed a fruit smoothie and a muffin, and sat down to read 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 good, 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, “Fancy meeting a girl like you in a place like this.”
She chuckled nervously. “Sorry for the hasty retreat this morning. I just needed time to think.”
Realizing I might still have a chance, I asked, “Did you have time to think?”
She scanned the room, looking for I don’t know what, before sitting down beside me. “Yes, I did.”
She seemed to be struggling with 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 played it cool, offering an olive branch. “The offer from this morning still stands, Miss Morgan.”
She seemed to be attempting to process this when I decided to take a risk. I 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. If you want to take me up on my offer, pick me up. If you don’t, I will 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, the evidence I needed to feel confident my seduction was working. Satisfied I had enticed her, I stood up and walked away. I was tempted to look back, but resisted.
I couldn’t believe how excited and nervous I was while I waited to see if my boldness paid off. Two weeks ago I was too shy to even 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 enticed her enough.
Just as I was beginning to think I had failed a second time, Miss Morgan pulled up. I 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 are going to do this.”
I attempted to comfort her and convince her she made the right decision. “Me either, Miss Morgan. I have wanted this to happen for a long time.”
“Really?” she asked, surprised.
“Miss Morgan, I began to think I might be a lesbian when I started taking your class. I began dreaming about you. I fantasized kissing you, touching you, pleasing you. I just never thought you might be interested in someone like me.”
“Oh my God, Jenny, I have 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?”
The conversation was getting very real. I knew I had changed a lot these past couple of weeks 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 announced 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 are a great young lady and have a bright future ahead of you.”
Tears began to roll down my cheeks. It was 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 am 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.
Her face turned red and her breathing changed just slightly. “Jenny, are you sure?”
“Miss Morgan, I am unsure of many things in life. But when it comes to this,” I paused, “I have never been surer of anything in my life.”
We arrived at her house and pulled into her garage. Once parked, Miss Morgan seemed to hesitate, unsure what to do next. I moved my hand under her dress. 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. My tongue parted her lips and, although tentative at first, Miss Morgan kissed me back. I pushed my finger hard onto 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 so many nights while in my bed with just me 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, “Let’s go inside, Jenny.”
Attempting to push the envelope, “Yes, Mistress Morgan, anything you say.”
She gave a slightly startled look, but didn’t say anything as she got out of the car and 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 pushed me onto her bed and crawled on top of me. She leaned in to kiss me. Her lips barely touching mine, she kissed me ever so gently. She followed the soft pecks by sucking on my lower lip. I had never been kissed like that and it was driving me crazy, making my pussy very damp. She moved down to my neck and gave 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 my breasts. Once freed from their confines, Miss Morgan cupped both in her hands and looked like a child in a candy store. She spent at least ten minutes adoring my breasts. She kissed, nibbled, and sucked on my nipples. The tenderness and deliberate teasing had me on the edge of complete ecstasy, desperate to come soon. I whimpered, “Mistress, please let me come.”
She bit my nipple, not hard, but hard enough to make a statement. “Princess, 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 horny body. Either way, when her head moved lower and under my cheerleader’s skirt, I let out an excited moan.
Miss Morgan asked, “Is one of your orders 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, her finger making just the slightest of contact with my pussy.
“Aaaaaah,” I let out. “I thought your first name was Wanda.”
“That is my middle name. I can’t have people knowing my real identity online.”
“That makes sense,” I whimpered again, her finger teasing me.
“You have such a beautiful vagina, Princess.”
She leaned in and under my skirt. I moaned in reply, as her tongue made contact with my pussy lips, “Thank you, Mistress Cameron.”
Her tongue explored my whole pussy region. She slowly moved her tongue up and down my lips, lightly teasing me. Her tongue slid below my pussy lips and teased the crack of my ass. I wanted to see her, so I begged, “Can you take my skirt off, Mistress? I want to be able to watch you.”
She moved out from underneath my skirt and, without a word, reached for my skirt. I lifted my ass to assist her and soon I was only wearing thigh-high red stockings. She smiled seductively before returning to my feverish pussy. She continued the slow meandering teasing, still avoiding my clit. I could feel juice beginning to leak out of me, her teasing driving me to the brink. My moaning began to increase with each lick of my teacher’s tongue. Suddenly, just when I couldn’t take it anymore, she slid a finger inside my pussy while at the same time taking my swollen clit into her mouth. In a second, I screamed, “Oh my fucking God, Miss Morgan, I’m coming.” An electric jolt tore through my body as an orgasm exploded out of me and through me. Miss Morgan let go of my clit, but kept finger-fucking me as she licked the juices leaking out of me. Much to my surprise, the continued attention kept my body revved up and, as one orgasm simmered, a second began bubbling inside. I begged, “Oh yes, Mistress Cameron, don’t stop, make me come again.” A second finger slid inside me, joining the first, and I let out a squeal of delight. She again took my clit into her mouth and somehow licked it while at the same time sucking it in her beautiful mouth.
The sensation and the stretching of my tight pussy had me again on the verge of orgasmic bliss. To my surprise, Miss Morgan finally spoke, her words sending shivers through me, “That’s it baby, come for teacher, come harder than you ever have, Princess.”
Hearing my sweet, beautiful teacher order me to come was the final breaking point. My body shuttered to a second, smaller, but still gloriously beautiful orgasm. “Oh yes, Mistress, you are too good to me,” I moaned, pure pleasure resonating inside me.
Miss Morgan pulled her two fingers out of me. She lapped up my juices for another minute, before sitting back up and moving beside me. Lying face to face with me, my juices coating her face, she complimented, “You have the most delicious pussy I have ever tasted.”
The compliment sent a chill up my spine. I am sure I blushed as I responded graciously, “Thank you, I bet you taste divine yourself.”
It was Miss Morgan’s turn to blush. “I get very few complaints.”
“I bet you don’t,” I teased, before asking, “Anyone I know get the privilege of pleasing you?”
Her face went from blissful to panic as she responded, too quickly, “Oh, no, no. I was just talking hypothetically.”
Her reaction told me she had at least one lover and I wondered if it was someone I knew, but decided not to push it, deciding instead that it was time to return the favour. I attempted to be seductive, “Miss Morgan, is there anything I can do for you?”
I could tell she was slightly nervous, which seemed ironic after what she had just done to me. I could tell she was trying to find a way to tell me what to do, so I decided to do it for her. I moved up and kissed her gently. I pulled her up and unzipped her dress. With a bit of a struggle, I took off my teacher’s blue dress. I was then face to face with her beautifully firm breasts, barely being held inside her white lace bra. I kissed the top of her breasts while I fumbled with the buckle of her bra. Eventually, I released my teacher’s large breasts from her fabric prison and took one of her nipples into my mouth. Miss Morgan moaned and I cupped, fondled and sucked on her large ‘C’ breasts for a long time, becoming completely lost in them. Finally, I moved down her body and slowly pulled off her pantyhose. I suggested, “Miss Morgan, for future reference, it is way easier to get to your appetizing pussy if you wore thigh-high stockings.”
“I will have to buy some then,” she replied, her breath already anticipating my tongue.
Once I had her pantyhose off, I slowly removed her pink undies. I returned between her legs, eager to taste her. Her pussy was not shaved nor really hairy, just natural. I buried my head between her legs. Her legs stiffened, anticipating my touch, but I teased, “Miss Morgan, can I eat your pussy?”