Bedding the Babysitter Ch. 03

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Note 1: All characters are at least 18 years old.

Note 2: Although I recommend you read parts 1 and 2 first, here is a summary of this series so far…

Note 3: A massive edit and rewrite occurred in April 2018 with Tex Beethoven and Wayne.

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.

Bedding the Babysitter: A Cheerleader’s Recruit

What a weekend! Jenny had become a perfect little submissive! Seeing her glow brighter and brighter as she came to grips with who she really is was very rewarding. Many people have been asking, dying to know what happened after that first glorious weekend. Well, the best way to tell you about the next stage of her journey is to let my young babysitter slave tell you about it herself. So if you want to know about Jenny’s journey to popularity, her submission at the hands of the head cheerleader Karen, her seduction of a teacher and how she fell in love, please read on.


My name is Jenny. Mistress Megan has asked, well demanded actually, but that’s ok, I like her telling me what to do, so she’s demanded (in a nice way) that I tell you about my past week’s occurrences, and of course I will obey. If you have read the first two parts of my Mistress’ Bedding the Babysitter series (which I highly recommend reading if you have not) you already know how I came to be a (happy) submissive slave. If not, and you’re silly enough not to go do that right now, let’s just say before that eventful and life-altering weekend I was a closet lesbian who had no real experience to know for sure whether I was an actual lesbian or not.

But after just one weekend with my beautiful Mistress, I had a new job, I had my fantasy of being with Karen the head cheerleader come true, and I’d been to a lesbian club. There, with my Mistress’ help and guidance, I had begun to really experiment with my sexuality and my obedience. (And to learn what really good orgasms feel like.)

The following story is the first week of the rest of my life, during which I had another adventure with my mistress, I attempted to seduce a teacher, I became an obedient cheerleaders’ servant and, oddly enough, became a cheerleader myself…oh yes, and I fell passionately in love.


SUNDAY FEBRUARY 2ND: A Reflection and Babysitting Again

As any calendar will tell you, next week actually began on Sunday. It was in the afternoon, the day after my brief submission to Karen at her workplace. I was exhausted from my long evening at the Le Chateau Club, a special club that caters to lesbian women, followed by a long night spent pleasing the governor of our state. I won’t get into the details of that long night, as Mistress Megan has instructed me to focus on my cheerleader submission. Let’s just say that our governor is one very demanding and kinky lady. And she’s really hot, but even if most people don’t know about the kinky part, everyone knows she’s hot, don’t you?

I got a call around 2:30 from Karen Pepper and here, as best as I can recall, is the conversation:

“Hello, is Jenny there?” a girl’s voice asked.

“Speaking,” I responded, unaware it was Karen.

“This is Karen,” she informed me.

“Oh!” I said, slightly surprised and instantly out of my comfort zone. It was one thing to submit to her in front of Mistress Megan, as I was only obeying my Mistress and I always feel safe when I’m with her, but it’s completely another thing to have to speak for myself. Instantly I reverted to the shy closet lesbian I had always been, the wallflower no one knew or noticed, insecure and unsure of myself. Now don’t get me wrong; I had friends, but they were both (all right, I didn’t say I had lots of friends) just shy geeks like I was. We lived in our little pond and cheerleaders lived in their much larger one. In reality they were royalty, we were the peasants.

“Just oh? Is that any way to greet someone who is going to make you popular?” Karen asked, slightly annoyed with me.

“Popular?” I repeated, in a haze.

“Yes, popular. You.” she said, “I put a lot of thought into this last night as I reflected on how great it was to have you between my legs yesterday. So I came up with a great plan.”

“You did?” I asked, unable to put a full, complete and intelligent sentence together. After all, this was Karen, the Head Cheerleader! You try and act intelligent around such a hot and popular girl!

“Yes, I’ve decided to make you a PomPom.”

This shocked me. The PomPoms were always freshman or second year cheerleader wannabes who were pretty much servants for the actual cheerleaders. They carried Ümraniye Escort the royalty’s trays for them at lunch, did their homework for them, and so forth. No senior had ever been a PomPom. It would be too humiliating. A long pause followed as I reflected on this revelation.

Karen broke the silence by asking, “You don’t want to be a PomPom?”

I collected myself so I wouldn’t embarrass both of us by blurting out, “Hell no,” before managing to actually respond with a stutter, “I-I-I thought only f-f-freshmen were PomPoms?”

Karen responded, “Well, that’s usually the case, plus the odd second-year. But as Head Cheerleader, I really can do whatever I want and…” she paused, her tone changing ever so slightly to sound a bit more self-important, “…I want you to be a PomPom.”

“But what will other people think?” I asked, worried for the first time in my life about my reputation.

“Well, the other PomPoms will be furious and will do whatever they can to crush you. My fellow cheerleaders will be slightly confused but they won’t question me because they wouldn’t dare, and the rest of the school will finally know you exist,” she analyzed logically, before adding, “Although I imagine the gossip about you will range from mean to curious to sarcastic to who knows what else.”

Again, I had nothing to say. I was unsure what Karen had in store for me. “I don’t want the whole school to know I’m a…” I started.

“Lesbian?” she asked and then added, “Dyke?”

“Yes,” I whispered, ashamed.

“Well, that secret can remain a secret for the most part. I won’t announce it to the school if that’s what you mean. But I will expect you to be a ‘good little girl’ whenever you’re asked.”

“What do you mean?” I asked, just beginning to understand the full reality of yesterday’s submission. I had after all asked Mistress Megan to make me Karen’s slave. “Be careful what you wish for.”

“Well, I plan to use you over and over and over and over again, and my two co-captains will also be allowed to use your good little girl services sometimes too, understood?”

My face went white with fear as I realized what her plans were; although my pussy also went wet with excitement at the same time. Now, while Karen was a redhead with green eyes, large breasts and rather compact at 5’2″, Ashley Swanson and Sabrina McCafferty were her perfect counterparts.

Sabrina was strangely chunky for a cheerleader, I thought, with breasts way too big for any human girl at all; she was about 5’4′ and had a surprising amount of confidence in herself for a girl who wasn’t particularly attractive. On the other hand, Ashley Swanson was almost 6 feet tall, a brunette, with long, long legs reaching all the way to the ground, brown eyes and very small breasts. She was pretty, but in a conservative way if that makes any sense.

I attempted to answer ‘yes I understand,’ but nothing came out of my mouth. Karen, clearly getting tired of waiting, said, “Jenny, I know you want this, so don’t pretend you don’t. I have one question to ask you; if you say yes, then I will expect you to do as you’re told from henceforward. If you say no, then I’ll understand and will not bother you ever again, not even tell anyone about yesterday’s fun romp. Ready for the question?”

Feeling I was on a quiz show with everyone watching and hoping I got the answer wrong, anxiety filled me as I realized I didn’t want to displease her. I responded nervously, “Yes, I am.”

“Good girl,” she said like a mother would say to her little daughter if she did as she was told. She paused, leaving me hanging (I think on purpose) over what seemed like an eternity, “Do you ever want to taste my pussy again?”

My spine had a chill go down it and my pussy got a little wetter just from the question. My answer was obvious: of course I wanted to taste her again! She was my fantasy girl! Yet, at what cost? If I said yes, everything in my life would change: the whole school would know who I was and keeping my secret a secret would get a lot harder. That said, if I said no, I would never be allowed to please Karen again and I would remain the unpopular nobody I currently was. As my hand decided all on its own to influence my decision by rubbing my clit, I answered, “Yes.”

“Yes, what?” Karen asked leadingly.

Knowing that what she wanted was my formal submission, I said, “Yes, I want to eat your pussy again.”

“You will obey?”

“Yes, Mistress Karen, I will obey,” I responded like a good little slave. I then pleaded, “But please don’t humiliate me in public.”

“Mistress Karen, I like that. If you’re a good lesbian pussy slave, I will make sure you’re protected, my precious,” Karen reassured.

“Thank you, Mistress Karen,” I said sincerely.

“I will pick you up at 8 o’clock tomorrow morning. I will have your PomPom outfit ready for you,” she informed me.

“Understood, Mistress Karen,” I answered obediently.

“You’re Ümraniye Escort Bayan getting my pussy wet,” she said surprisingly. She then continued, “Be sure to wear those sexy stockings you were wearing on Saturday.”

“Yes, Mistress Karen,” I said, but asked, “Won’t they be totally visible below the PomPom skirt?”

“Yes, of course they will,” Karen responded casually.

“Oh,” I said, slightly worried.

“Do you have a problem with that?” Karen asked.

“No, Mistress Karen,” I responded, “It’s just… I don’t want the whole school to think I’m a tramp.”

Karen let out a soft laugh, getting more excited by her developing plans as she went, “I’ll have all the other PomPom girls and even the cheerleaders wearing the same thing. I’ll wear the same thing too! That way you won’t stand out. Plus, when you and your other Mistress wore them yesterday I found them to be a turn on. So the entire cheerleader squad will be wearing them and we’ll start a new fashion revolution. Out with the old boring knee-high socks and in with the sexy thigh highs. You should feel special my pet, you’re about to start a fashion craze.”

“I am?” I asked, confused.

“Yes,” she answered, “When others see the cheerleaders and me, the queen of the school, wearing thigh highs, they’ll copy us. You just watch!”

“OK,” I said demurely, believing her, “I will be ready and dressed as you requested, Mistress Karen.”

“Fuck, I love being called that,” Karen said, giving a soft moan.

I asked daringly, “Mistress Karen, are you masturbating because of me?”

“Yes,” she moaned, “Tell me a story, my hot little lez, get me off.”

“I can do that!” I said, really liking the idea of getting my dream girl off. I considered briefly before beginning, “So you are at school, Mistress Karen, and your pussy is all fired up. You text me while I am in class, demanding I go to the bathroom. I ask to be excused from my class and quickly head towards the bathroom. I knock on the door and you say ‘get in here, slut’. I walk in and close the door, being sure to lock it. You then demand, ‘Eat my pussy, my lez whore’ and I get on my knees and dive into your pussy. You call me all sorts of dirty names as I get you off like a good slave should.”

“Aaaaaaaaaah,” Karen screamed into the phone as she had an orgasm from my dirty little story. Inside I felt a great joy and a spreading of warmth in my pussy as I knew I had pleased my mistress.

“Did I make you cum, Mistress Karen?” I asked, knowing the answer.

“Yes, my pet,” she panted into the phone, still breathing heavily.

“Thank you, Mistress Karen, for allowing me to help you cum. It is an honour to be responsible for your pleasure,” I said sincerely, my hand still rubbing my own clit softly, but now I was more aware of it. “Mistress Karen?” I asked.

“Yes, my slave,” she asked, almost recovered from her orgasm.

“May I have your permission to cum?” I requested. “My other Mistress says I can’t cum without permission anymore.”

“Yes, my little tramp, cum for your Mistress, and do it now,” she demanded.

I quickly rubbed my clit, faster and faster as I fantasized about all the things Karen might make me do. It took less than a minute and I moaned, “I’m cumming!” and let out an orgasmic moan.

Karen asked, “Did you cum, my dyke?”

“Yes Mistress Karen, thank you for letting your lezzie slut have an orgasm,” I responded blissfully.

“That wasn’t much of a scream, a good lesbian should scream so the whole world knows she’s having an orgasm.”

“Sorry, Mistress Karen, but my mother is downstairs and I would hate for her to hear me in such a compromising position. She thinks I am her innocent, sweet, pure daughter and not a lesbian cunt slave,” I explained.

“Fair enough,” Karen said, “But when you cum for me when we’re alone, I expect the walls to shake.”

“Of course, Mistress Karen,” I agreed, “I will do whatever you ask of me.”

“You’re such a good little lez. What about Megan?” she asked.

“Yes?” I asked.

“Is she still your Mistress as well?” she asked,

“Yes Mistress Karen, Mistress Megan wants me to consider her my Head Mistress and if I understand her completely, she is your Mistress as well,” I explained.

“Oh,” she said thoughtfully, “Do you think Megan would take me as a slave?”

“Oh yes,” I said, sure I was right.

“Well, when do you plan to see Mistress Megan next?”

“She texted me this morning, asking me to come over at five to babysit. I don’t know if she really means babysit or something else,” I said, unsure of Mistress Megan’s purpose and how to answer Mistress Karen’s questioning correctly.

“I see,” Karen said, “Please tell Mistress Megan I would love to see her again.”

“Yes Mistress Karen,” I said, “I am sure she will be glad to hear it.”

“What is your cell number?” she asked. I gave to her and she gave me her own digits Escort Ümraniye back. I put them in my cell phone under my favourite five.

“I will see you at eight tomorrow morning, my slut,” Karen confirmed once again. I was surprised and flattered she didn’t have to ask where I lived.

“Yes Mistress Karen, I will be ready,” I responded.

“Goodbye Jenny,” she said, using my name for the first time ever.

“Goodbye Mistress Karen,” I responded, and she hung up the phone. I did the same and reflected about our conversation. Karen was submissive to Megan but dominant to me, which I thought was strange. I went to my desk and did some Calculus homework for a while and then began to write my Pride and Prejudice essay that was due in a couple of weeks.

At ten to five I put on white thigh high stockings, a red sweatshirt, and a long skirt, as mother was home and would think it odd for me to leave on a Sunday in my school outfit. I arrived at Megan’s and saw her dressed casually in jeans, a blouse and open toe heels that showed she had tan stockings on underneath. She gave me a hug and said, “You didn’t know whether this was actual babysitting, did you?”

“No,” I said slightly disappointed.

“Sorry to disappoint. I’m going out for supper with a couple of friends and then to a movie. I should be home around 9:30 or so.”

“OK,” I said, trying to be my usual bubbly self, although inside I was devastated. Trying to get her interest back, I said, “Karen called me, she asked me if I wanted her to be my Mistress and I said yes. I hope that was ok.”

“Yes, that’s what we established on Saturday, so it’s fine. She probably just wanted to formalize it by getting you to say so.”

“Yes, it did sound like that, Mistress. She also said she was hoping to be able to see you again.”

“Oh,” Megan said, “Well that can be arranged. Do you have her number?”

“Yes, Mistress Megan,” I said, grabbing my cell phone. I handed it to her and she hit dial.

“Hi Karen,” Megan said, “It’s Megan.” There was a pause before she continued, “Yes, it’s good to hear your voice again too. So Jenny here says you’re interested in seeing me again.” After a brief pause she said, “Good, well, I’m free on Tuesday evening, are you? Good. Now you must understand if you come over, you are mine for the night.” After a brief pause, Megan gave me a wink as she said, “And I expect you to treat my little Jenny well. Learn to be a good Mistress to her. In return she will be a perfect slave.” Megan laughed at something Karen said and she then added, “Yes, she is very obedient. I will see you on Tuesday at seven PM, do not be late.”

Megan handed me back the phone and asked, “Are you free on Tuesday?”

“Oh yes, Mistress Megan!” I said a little too eagerly.

“Great! I am going to train Karen how to be a good Mistress to you,” Megan explained.

“Thank you, Mistress Megan,” I responded gratefully.

Megan came up to me and kissed my lips gently. She then broke the kiss and said, “I will always look after you, my sweet.” She began to leave and then said, “Max is in the basement watching Toy Story 3 for the hundredth time in a row. Be sure to put him to bed at eight o’clock. After he goes to sleep, there is a reward for you in the envelope on the kitchen table.”

I looked over to see a vanilla-coloured envelope on the table. She smiled and said sternly, “Do not open it until Max is asleep.”

Max ran up the steps at that moment and so I responded with, “Yes, Ms. Cameron.”

Max gave his mother a big hug goodbye and then ran to me and said, “Jen, play hide and seek with me.”

I bent down and said, “Of course, Max.”

Max announced, “I get to hide first!”

I smiled and started counting, “1-2…” Max immediately ran away to hide.

Megan smiled and said, “Jenny, you really are the perfect all-around babysitter.”

“I aim to please,” I said, awkwardly seductive.

“That you do, my precious,” Megan said as she headed out her front door.

I spent the next couple of hours playing with Max, who is a funny, funny boy. We watched Toy Story again, played games, had a snack, cleaned up his snack mess and I read him three books. He eventually fell asleep, way later than he was supposed to, while I eagerly anticipated whatever was in the envelope. As soon as I was sure he was asleep, I hurried to the envelope and opened it.

It was a letter. It said, “Dear Jenny. Go to my computer and log in as DrMeg, password JennyBoss1. When you do, go to my files, find the bin called ‘my stories’ and click on Bedding the Babysitter. Read it.”

I followed Mistress Megan’s instructions and, after a few minutes, I was face to face with my own story! I went ruby red I imagine, as I realized she had documented my entire submission. I read the story, learning exactly how I was seduced, and all the thought my Mistress had put into planning it. I was in awe! I then relived my first time with her from the printed screen and began to rub myself. I took my time, just teasing myself. As I read about Saturday, a flood of memories washed over me. Each detail made me smile, made me cringe, made me want to relive it again and again. I finished the story and was surprised to learn that Mistress Megan had lined up to please Big Rosie.

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