Bedding the Babysitter Ch. 03bysilkstockingslover©
Note 2: All characters are at least 18 years old.
Note 3: Although I recommend you read parts 1 and 2 first, here is a summary of this series so far...
Part 1-Megan, a dominant but caring lesbian, seduced her cute and innocent babysitter Jenny.
Part 2-Megan takes her new submissive lesbian shopping, makes a fantasy come true with a cheerleader that Jenny had dreamed about forever and took her to a special lesbian only bar.
Bedding the Babysitter: A Cheerleader's Recruit
What a weekend. Jenny had become a perfect little submissive. Seeing her glow as she came to grips with who she really is was very rewarding. Anyhow, many people have asked dying to know what happened after this first glorious weekend. Well the best way to tell you about it 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 hands of the head cheerleader Karen, her seduction of a teacher and falling in love please read on.
My name is Jenny. Mistress Megan has demanded I retell my past week's occurrences. 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 submissive slave. If not, 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 if I was an actual lesbian.
But within just one weekend with my beautiful Mistress, I had a new job, had my fantasy of being with Karen, the head cheerleader, come true, and had been to a lesbian club. There I had begun to really experiment with my sexuality and my obedience.
The following story is the first week of the rest of my life, in which I have another adventure with my mistress, I attempt to seduce a teacher, I become an obedient cheerleader's servant and, oddly enough, become a cheerleader myself...oh, and I fall in love.
SUNDAY FEBRUARY 2ND: A Reflection and Babysitting Again
It actually began on Sunday afternoon, the day after my brief submission to Karen at her workplace. I was exhausted from my long night at the La Chateau Club, a special club that caters to lesbian women, and an evening pleasing the governor of our state. I won't get into the details, as mistress has instructed me to focus on my cheerleader submission. Let's just say that our governor is one very demanding and kinky lady.
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 voiced 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 felt safe when she was with me, but it was completely another to actually speak for myself. Instantly, I became 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 all just shy geeks like I was. We lived in our pond, they lived in theirs. In reality, they were royalty, we were the peasants.
"Is that any way to react to someone who is going to make you popular?" Karen asked, slightly annoyed.
"Popular," I repeated in a haze.
"Yes," She said, "I put a lot of thought into this all last night as I reflected on how great it was to have you between my legs. I came up with a great plan."
"You did?" I asked, unable to put a full complete and intelligent sentence together.
"Yes, I have decided you will be 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 their trays for them at lunch, did their homework for them, and so forth. No senior had ever been a PomPom. It would be humiliating. A long pause followed as I reflected on this revelation.
The silence was broken by Karen who said, "You don't want to be a PomPom?"
I collected myself before responding with a stutter, "I-I-I thought only f-f-freshmen were PomPoms?"
Karen responded, "Well, that is usually the case, and the odd second-year. But as Head Cheerleader, I really can do whatever I want and," she paused her tone changing ever so slightly, "I want you to be a PomPom."
"But what will others 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 have to do to crush you. My fellow cheerleaders will be slightly confused, but they won't question me and the rest of the school will finally know who you are," she said logically, before adding, "Although I imagine the gossip about you will range from mean to inquiry to sarcastic to who knows what."
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 am a..." I started.
"Lesbian?" she asked and then continued, "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 is what you mean. But I will expect you to be a good little girl when asked."
"What do you mean?" I asked, just beginning to understand the full reality of yesterday's submission.
"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 services, 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, strangely quite chunky, for a cheerleader, I thought, with breasts way too big for any girl; she was about 5'4 and had an odd air of confidence in herself for a girl who was not particularly attractive. On the other hand, Ashley Swanson was almost 6 feet tall, a brunette, with long, long legs, brown eyes and very small breasts. She was pretty, but in a conservative way, if that makes any sense.
I attempted to respond, 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 expect you to do as you're told. If you say no, then I understand and will not bother you ever again, nor tell anyone about yesterday's fun excursion. Ready for the question?"
Anxiety filled me as I realized I did not want to displease her. I responded nervously, "Yes, I am."
"Good girl," she said like a mother would say to her little daughter when she did as she was told. She paused, leaving me hanging 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 by the question. My answer was obvious; of course I wanted to please her again. She was my fantasy girl. Yet, at what cost? If I said yes, everything in my life changed; the whole school would know who I was and keeping my secret a secret would be 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 began to rub my clit, I answered, "Yes."
"Yes, what?" Karen asked leadingly.
Knowing that what she wanted was my ultimate 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 are a good lesbian pussy slave, I will make sure you are protected, my precious," Karen reassured.
"Thank you, Mistress Karen," I said sincerely.
"I will pick you up at 8 o'clock tomorrow morning. I have your PomPom outfit ready for you," she instructed.
"Understood, Mistress Karen," I obediently answered.
"You are getting my pussy wet," Karen 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 visible with the PomPom outfit?"
"Yes they will," Karen said causally.
"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 all the school to think I am a tramp."
Karen let out a soft laugh, getting more excited as she talked, "I will have the other PomPom girls and cheerleaders wearing the same thing. That way you won't stand out. Plus, I found them to be a turn on. The entire cheerleader's squad will be wearing them as well; we are going to start a new fashion revolution. Out with the old knee high socks and in with the thigh highs. You should feel special my pet, you are going 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, others will copy us. You watch."
"OK," I said, 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, "Mistress Karen, are you masturbating because of me?"
"Yes," she moaned, "Tell me a story my little lez, get me off."
I considered briefly before saying, "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 talk. 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," she breathed 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 honestly, my hand now rubbing my own clit softly. "Mistress Karen," I said in a questioning tone.
"Yes, my slave," she asked, almost recovered from her orgasm.
"Do I have your permission to cum?" I requested.
"Yes my little tramp, cum for your mistress, do it now," she demanded.
I quickly rubbed my clit, faster and faster as I fantasized about all the things she would 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 cunt have an orgasm," I responded blissfully.
"That wasn't much of a scream, a good lesbian would scream so the whole world knew she was having an orgasm."
"Sorry, Mistress Karen, but my mother is downstairs and I would hate for them 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 are together, I expect the walls to shake."
"Of course, Mistress Karen," I agreed, "I will do whatever you ask of me."
"You are such a good little lez. What about Megan?" she asked.
"Yes?" I asked.
"Is she your mistress as well?" she asked,
"Yes Mistress Karen, Mistress Megan is my Head Mistress and I believe if I understand her completely, your mistress as well," I explained.
"Oh," she said thoughtfully, "Do you think Megan would take me as a slave?"
"Oh yes," I said, thinking I was right.
"Well, when do you plan to see Mistress Megan?"
"She texted me this morning, asking me to come over at five to babysit. I don't know if she means babysit or something else," I said, unsure of Mistress Megan's purpose and Mistress Karen's questioning.
"I see," Karen said, "Please tell Mistress Megan that 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 her mine and she gave me her digits back. I put them in my cell phone instantly under my favourite five.
"I will see you at eight tomorrow morning my slut," Karen confirmed once again.
"Yes Mistress Karen, I will be ready," I responded.
"Goodbye Jenny," she said using my name for the first time in a long while.
"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 and dominant to me which I thought was strange. I went to my desk and actually 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 in my school outfit. I arrived at Megan's and saw her dressed casually in jeans, a blouse, open toe heels that showed she had tan stockings on underneath. She gave me a hug and said, "You didn't know if this was actual babysitting did you?"
"No," I said slightly disappointed.
"Sorry to disappoint. I am going out for supper with a couple of friends of mine 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 greatly devastated. Trying to get her interest back I said, "Karen called me, she was hoping to be able to see you again."
"Oh," Megan said, "Well that could be arranged. Do you have her number?"
"Yes, Mistress Megan," I said as I grabbed my cell phone. I handed her my cell phone and she hit dial.
"Hi Karen," Megan said, "It is Megan." There is a pause before she continued, "So Jenny here says you are interested in seeing me again." After a brief pause she said, "Good, well I am free on Tuesday evening; 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 from something Karen said as 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 said, "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 said as an explanation.
"Thank you," Mistress Megan I responded gratefully.
Megan came up to me and kissed me on the 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 100th time in a row. Be sure to put him to bed at eight o'clock. After he is asleep, there is a reward in the envelope on the kitchen table."
I looked over to 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 changed my response to "Yes, Miss Cameron."
Max gave his mother a big hug and then ran to me and said, "Jen play hide and seek with me."
I bent down and said, "Of course, Max."
Max said, "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 what was in the envelope. As soon as I knew he was asleep, I went to the envelope and opened it quickly.
It was a letter. It said, "Dear Jenny. Go to my computer and log in. When you do, go to my files, go to 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 story. I went ruby red, I imagine, as I realized she had documented my submission. I read the story, learning exactly how I was seduced. I was in awe. I then relived my first time 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 Rosie.
I was still rubbing myself when Megan walked into her room. I was so immersed in her story that I did not hear her come home. She said, "I see you are enjoying your story."
"Very much so," I said.
"Guess what?" she asked as she pulled me up from the chair.
I looked into her eyes and asked, "What Mistress?"
"That story you read," she began teasingly.
"Yes, Mistress Megan," I queried.
She kissed me and then began, "I plan..."
Another kiss as she teased, "To." Her mouth moved to my right ear as she whispered, "submit this story," she continued as she moved to my other ear and finished the sentence, her hot breath on my ear, "to Literotica."
Her lips went to my neck as I said, "Oh my."
"Think very soon" she whispered, her hand sliding to my pussy, "the whole world will know your story." I moaned as she rubbed my clit. "Pervs, dykes, young eighteen year old girls like you."
"Whatever you wish, Mistress Megan," I breathed heavily.
"Good," she said, "As I plan to send it to my online friend Jasmine who will take the story and make it all erotic and so forth. Have you read any of her stories on literotica? She goes under the name silkstockinglover."
I recognized the name as I continued to moan, "The name sounds familiar."
Megan then abruptly quit touching my pussy and moved to the bed. "You can read all her stories tonight when you get home. She is one crazy bitch."
I stood there unsure what to do. I finally asked, "Can I please cum, Mistress Megan?"
"No," was all she said.
I waited for her to say more but she just stared at me with an unreadable expression on her face. It then turned into a slight smirk. This frustrated me greatly until I finally asked, "Why, Mistress Megan?"
"All good things come to those who wait," she said philosophically. Seeing my confused, frustrated and annoyed expression she added, "You are not allowed to cum until Tuesday. If Karen tries to force you, you tell her you are forbidden." She paused and then said, "Actually, give me your phone again."
I handed it to her.
She hit the speed-dial and after a few seconds she said, "Hi Karen, it is Mistress Megan." After a couple of seconds she continued, "Neither you nor Jenny are allowed to have an orgasm until I see you two together Tuesday evening, is that understood?" A second later she said, "Goodbye slut," and handed me back the phone. She then finished, "Don't worry my sweet, I won't touch myself until then too." She walked over kissed me sweetly one last time and said, "You better get going home. You have school tomorrow."
"Yes, Mistress Megan," I said, and feeling and depressed, left and returned home.