Bedding the Babysitter Ch. 02

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Note 1: Of course everyone in this story is at least 18.

Edit Update: A massive edit of the story occurred in April of 2018 by Tex Beethoven (the original was never edited by anyone other than yours truly) and Wayne.

Note 2: If you want to know how eighteen-year-old babysitter Jenny became a submissive slave to her neighbor Megan, please read Chapter One. Without further ado, here’s part two for you:

Bedding the Babysitter Ch 02:

Last night I had completed the seduction and domination of my eighteen-year-old babysitter. Today, a Saturday, I hoped to begin to make her greatest fantasies come true. So after my ex-husband (the less said about him, the better) came and picked up our son for his customary every-second-weekend custody time, I msn’d Jenny. It was just after lunchtime.

DrMeg: How is Jenny this fine afternoon?

Jenny78ph: Very well, Mistress.

DrMeg: That is good to hear. No regrets about last night’s events?

Jenny78ph: None! 🙂

DrMeg: Ready for your training to continue?

Jenny78ph: Yes, Mistress.

DrMeg: Are you dressed already?

Jenny78ph: Of course.

DrMeg: Come on over, we will research Karen before we head out to begin your transformation.

Jenny78ph: Transformation?

DrMeg: Of course. Your new look. We are going to make you irresistible to Karen.

Jenny78ph: But what if she doesn’t like girls?

DrMeg: Let’s find out.

Jenny78ph: OK.

DrMeg: So get over here right away.

Jenny78ph: Yes, Mistress.

Jenny arrived wearing the exact same outfit as yesterday. An adorably hot plaid but scandalously short school skirt, a white school blouse that showcased her nice perky little breasts, dark mocha thigh high stockings and, sadly, runners. I led her upstairs and slid out of my black leather skirt to reveal my black silk panties and matching black thigh highs. I requested, “Jenny, will you please come sit under my desk and pleasure me while I research your little dream cheerleader for you?”

“Yes, Mistress,” Jenny replied. She quickly crawled into place and went right to work with her eager little tongue as I began typing and clicking.

I gave out a soft moan and asked, “Jenny, what’s Karen’s last name?”

Jenny looked up at me from between my legs, so cute, and answered, “Pepper.” She then went back to pleasing my already damp pussy. I requested, “Jenny dear, please go nice and slow; I don’t want to climax anytime soon, I just want to feel stimulated and pleasant while I do this research for you; so try and emulate Sade songs being sung into my pussy.”

I believe she said, “Yes Mistress, I can do that,” as a response but it was incoherent, her suddenly singing tongue busy pouring a mix of misty melodies into my cute cunt.

As I researched, I learned that Karen came from a well-to-do family, lived in a massive upscale house and was an only child. On Facebook (on which, by the way, you should protect yourself much better than most people do) I learned she was a redhead with green eyes, she was short at 5’2″, but from her photos her breasts appeared to be quite large. I then created a new Facebook account under the fake name of Sarah Conners and requested her to be her friend, with a note explaining that I was a girl researching ‘Cheerleaders’ Impact on the Student Experience’ (again, you really should protect yourself from online predators such as myself). Not surprisingly, she accepted me five minutes later. I created a questionnaire for her and sent it to her, hoping she would respond. As I waited, I read her wall and learned some more about her. Her tone was often very sarcastic, she hated her mother, she loved getting compliments… revelled in them really… and could be quite spiteful. She frequently posted comments such as “Mrs. Wicks is a complete bitch” or “Did you see what Sara wore today, it made her look even fatter than she already is, if that is possible.” After reading her wall I looked forward to attempting to seduce her. I also learned she had a part-time job working at Mill’s Boutique (the best and most expensive women’s clothing store in town) and based on her status, she was at work right now.

All this time Jenny was slowly licking my pussy, nibbling jazz ballads ever so gently on my pussy lips. I moaned and said, “Good girl, my little virtuoso pussy pleaser. Now please slide a finger in your mistress’s pussy and finger fuck me as you lick me a bit more up tempo, perhaps like ‘Smooth Operator’; I’d like to come soon.” She obeyed, faster and with more syncopation, and I just leaned back and enjoyed her up-tempo stimulation. When I was close, I grabbed her head and pushed it into my pussy and just held her pretty face there as illegal bahis I semi-quavered through a small but intense orgasm. As I regained my equilibrium, Jenny still nestled between my legs, I noticed that Karen had already responded to my questions; she must be having a slow workday. I pulled Jenny up beside me to share my results inviting her, “Let’s see how your little dream cheerleader responded to my questions.”

This survey is completely confidential and will be tabulated for inclusion in an article I am preparing about ‘Cheerleaders’ Impact on the Student Experience’ for a national magazine. (Please answer all questions frankly and honestly, as your responses are integral to the validity of this article and for my analysis of the vital role that cheerleaders play in our secondary schools):

Name: Karen Pepper

Grade: 12

Age: 18

Cheerleader Position: Captain

Years as Cheerleader: 4

Do you approve of hazing within cheerleader squads? Of course. Like our sports teams, you must earn your place among us. We have a hazing week that includes a variety of tasks like making out with one of the ugliest boys in our school, attending gym class without any bra or panties, a competition for who can flirt with the most teachers of either sex (each acceptable flirtation to be witnessed by at least one senior cheerleader), stealing an item at the mall, and we always finish the week by requiring the new cheerleaders to imbibe alcohol while making out with each other and being filmed.

What is your favourite perk from being a cheerleader? I can’t choose only one, since there so many. I already have a scholarship lined up for next year’s college, I can have any hot boy I want, I get to wear my outfit anywhere I want and I am treated like royalty by most of my peers and teachers.

Do you feel you receive special treatment from your teachers because you are a cheerleader? Sure. All I ever have to do for the male teachers is give them my puppy-dog look or showcase my legs a little extra and I usually get what I want… actually, make that ‘always’. The female teachers are a bit tougher, but very few want to mess with us cheerleaders as we have a reputation for being quite influential and powerful.

How do you select your squad? It is based on looks, fitness and social status. This may sound conceited, but if you are not attractive, sexy-looking and well-connected, you probably should not aspire to becoming a cheerleader. On occasion we take on a girl without great social standing if we think we can train her, but usually this is not worth the effort as they never really fit in with our social circle. I know this is elitist, but when you’re the best, elitism is an asset.

Some schools are cancelling cheerleading programs because of the rise of teenage pregnancies; is that a concern for your squad? God no. I am not saying we don’t have sex, but we are all on the pill. As captain I insist on it, and our past captains have too.

Last question, is there any lesbian activity among your squad? Um…yes. Between cheerleading camp, nights in hotels during competitions and post-game celebrations there is often a fair amount of lezbo action. Plus, as girls dating incompetent teenage boys, although my boyfriend is in college, sometimes the only way to really get off is from a woman’s touch.

Any other comments: Please send me a copy of your published article. Kisses.

Thanks for participating in this survey!!!

“Well Jenny, I think it’s time to go shopping,” I said as I got dressed. She followed me out the door and we headed to the mall. I could see Jenny getting nervous as we arrived at our first stop…a beauty salon. We went inside and I had them give Jenny the full treatment. She received a leg wax, a smooth pussy shave (a waxing wouldn’t have allowed her much intimate fun for a few days), a manicure, a pedicure, a tanning session, a facial and finally she got a new hairdo, followed by having her make-up done.

When Jenny looked in the mirror, now dressed again in her modified schoolgirl outfit, she looked like a confident college girl on the prowl. She smiled, but asked guiltily, “How can I ever repay you for all this?”

“Don’t worry, believe it or not you deserve it, and this won’t cost either of us any money,” I responded slyly.

“Really?” Jenny asked, confused, her pure innocence still so charmingly adorable.

“Really,” I confirmed. “But I think it is time to pay for your makeover.” I grabbed her hand and led her to the private area behind the public salon. As we reached the head office, I walked in and greeted the owner, who was my best friend since college Krystal, giving her a hug and a tender kiss.

Krystal at almost six feet, towered over Jenny as she walked up to her illegal bahis siteleri and said, “So this is your new recruit. She’s very pretty.”

Jenny stuttered, “T-t-thanks.” Her hands trembled slightly as she fidgeted with her newly manicured hands.

Krystal put two fingers under Jenny’s chin and lifted her face up so they were looking eye to eye, although Jenny was gazing up and Krystal down. “Jenny,” she began, “Every girl who works here is a submissive slave of mine; does that surprise you?”

Jenny was attempting to process this information while Krystal returned behind her desk and continued, “For example, your manicure and pedicure were done by Carley and Jen. Those two were high school best friends I met at a club one night who both ended up pleasing me and another friend of mine in the ladies room. Your waxing was done by Kiako, who is a fourth-year med student originally from Japan and easily one of the prettiest girls in the entire world, although she doesn’t think so. She is also the most obedient little slave I have ever had. I picked her up in a movie theatre during an arts film I attended one day. Halfway through the film I changed seats to sit beside her (there were perhaps six people in the entire theatre) and without a word I placed my hand on her leg. When she didn’t react negatively to my initial advance, I simply whispered in her ear, ‘Open your legs, honey.’ She did so without hesitation and I fingered her to orgasm right there in the theatre. She came quickly and loudly, so loud the few other people in attendance were turning around to gawk at this cover-girl-appearing Japanese woman cumming on my fingers. I then sucked her juices off and whispered to her, ‘You are the most beautiful girl I have ever seen and I want to see you again. If you want that too, here is my card; be at my salon tomorrow at 6:00 in the evening.’ I kissed her, handed her my card and left. Of course she showed up the next evening, and has now become a great little cunt pleaser.

The others have stories too, my sweet, and you will learn them over time if you wish. I happen to have a part-time job opening here as salon facilitator; you would answer the phone, book appointments, work the till, do final clean-up and so forth. Are you interested?”

Jenny’s face lit up like a flare as she replied, “That would be great!”

Krystal walked around to sit on the front of her desk, raised her skirt and said, “Excellent! Are you ready for your first session of on-the-job training?”

I laughed, Jenny blushed, but since I obviously approved, she walked up to Krystal and knelt in front of her before requesting timidly, “Ma’am, may I please be of service?” Receiving an affirmative nod from Krystal, Jenny leaned into Krystal’s completely shaved pussy and began pleasing her new employer as I looked on. Partway through, I knelt behind my little vixen, gently squeezed her ass and slowly slid a finger inside her cunt, providing her with some encouragement but not getting her off. Jenny eventually brought Krystal to an orgasm and I pulled my finger out of her wet pussy.

“Well, I definitely think you are hired,” Krystal beamed as she stood up. Can you be here for training next Friday evening?”

“Yes, ma’am,” Jenny responded, her lips shiny with love juice before she licked them clean.

“Great,” said Krystal. “Be here at 5:00. We will train you till 9:00 and then you can attend our weekly Friday night social, which usually goes quite late,” she paused for emphasis, “if you get my drift.”

“Oh, I think I do,” replied Jenny, willing but still slightly nervous.

Krystal gave a little chuckle as she said, “Alright, go see Kirsten again and get your make-up touched up. You look like you just ate somebody’s pussy.”

I laughed and chit-chatted with Krystal as Jenny got a quick touch-up. As I returned to the front, Kirsten was just finishing and I heard the fortyish make-up artist telling Jenny, “I can’t wait to eat that young pussy of yours, Jenny.”

I chuckled as I escorted a newly drop-dead-gorgeous but completely red-faced Jenny back to the car. As I pulled away from the curb I teased, “Well Jenny, two pussies in two days, you’re turning into quite the little lesbian slut aren’t you?”

Jenny probably would have blushed even more if that were physically possible, as she responded, “I can’t believe I just licked a complete stranger.”

“Did you enjoy it?”

“Yes,” Jenny responded dutifully. “I just wanted to make her happy; I always hate being a disappointment.”

I sighed slightly. “Oh Jenny, we really need to work on your self-esteem. You are a beautiful girl, a smart girl and a very nice girl. Don’t you know that? Krystal doesn’t hire just anyone, she saw something special in you, just like I do.”

“Thanks,” Jenny responded, although her tone indicated she didn’t completely believe me.

“We’re here,” I announced as we arrived at our next stop, Mill’s Boutique. I assumed Jenny had no idea who worked here.

“Mill’s Boutique?” Jenny queried as we canlı bahis siteleri arrived. “Isn’t this that place where the rich and famous shop?”

“I suppose it is. Come on sweetie, I have a surprise for you.”

We got out of the car and walked towards the front door. But I paused before we entered and cautioned Jenny, “Before we go in I should explain that once we go in there, there is probably no turning back.”

“What do you mean?”

“Well, you can continue coming over to my place no matter what happens here, and you have a job with Krystal so you will still have lots of opportunities to be submissive, but if you walk through these doors and I proceed with my plan, you will almost certainly end up with a reputation in your school as a lesbian. Are you ok with that?”

Jenny tried to register what I was saying, “Um, probably, but I don’t understand.”

“Do you know who works here?”



Jenny’s face went white.

“If you go in there, I shall treat you as my lesbian slave in front of her and you must obey me absolutely and without hesitation.”

“Oh,” Jenny whispered.

“Jenny, I don’t want to do anything to you that you aren’t ready for. So if you feel this will be too much for you, just tell me no; I’m not ordering you to do this and you won’t hurt my feelings or disappoint me. But if you walk through this door and do everything I tell you, I am almost positive you’ll be eating Karen’s pussy very, very soon.”

Jenny considered my speech at length, really thought through it, and finally replied, surprisingly upbeat and thoroughly, “I trust you, Mistress. I will never refuse anything you ask of me and if you think this is a good idea, then I do too. As you say, I’m not obeying you in doing this, I’m right with you. So let’s go!”

“Great, Jenny!” I enthused, “Let’s go have some fun!”

I took her hand and we walked into Mill’s Boutique. Now I should say that my divorce as well as my job keeps me financially well off; I’m not a millionaire, but I do live a very comfortable life, so I could afford the absurd prices this boutique charged. The shop today wasn’t that busy, with only a couple of people browsing through clothing. One was a slightly overweight girl with someone I assumed was her mother, looking at wedding dresses; the other was obviously a trophy wife looking at cocktail dresses and treating her saleswoman with unjustified distain. I didn’t see Karen at first, which worried me a bit as we walked over to the cocktail dress section. As I was looking around, we were fortunate enough to have Karen come over to assist us.

“Good afternoon ma’am, “Karen greeted me politely, dressed in a classy black skirt, nude pantyhose, three-inch black boots and a white blouse. “May I help you with anything?”

I smiled and said, “Yes, you probably can. We’re attending a special gala tonight for charity and I need an outfit for myself and for my friend here. The outfits must look sexy, but not slutty.”

Karen asked for our sizes and left to select some outfits. I looked at Jenny and asked, “Are you ready to begin Operation Karen?”

Jenny laughed, as my question seemed to break the tension, although she fretted, slightly hurt, “Karen didn’t even notice me.”

“Well you do look very different from your usual appearance. Even though you’re still dressed in kind of a school uniform, you’ve gone from your normal conservative unflattering look to much more of a revealing, sexy look. Plus with your fresh make-up and hair, you could easily pass for twenty-one, which we will attempt tonight,” I said teasingly.

“What’s tonight?”

“That’s for me to know and you to find out later,” I responded coyly. “I enjoy surprising you.” At this moment I saw Karen returning with a few dresses and announced in a hushed voice, “Operation Karen is underway.”

Karen arrived to find both of us laughing merrily and said, “I chose a few dresses I think you might like.”

I tried on three different dresses that were all stylish and of good quality, but not what I wanted. So I said to Karen, “Honey, these are all ok, but I need something that will have every girl there checking me out.”

Karen showed just the slightest bit of shock but regained her composure quickly before she offered, “I think I may have just the thing.”

Karen left us again and I said to Jenny, “This is going to be easier than I thought.”

“How so?” she asked.

“Just watch. But now I need to know whether you want her to be your little slave or would prefer to be hers.”

“I want to be her slave,” she replied shyly but without hesitation.

“I thought you might,” I acknowledged just as Karen returned. She handed me a gold gown that was long enough to hide the tops of my thigh high stockings, but with a generous enough slit to display them occasionally for anyone paying attention. I gave her an inappropriate kiss on the cheek giving her a start, and said, “This looks excellent.” I took it from her and went into the change room. After donning the dress, I came out and studied myself in the mirror. I spent a bit of time analyzing the outfit before appraising, “It’s nice, but these black stockings don’t match the dress. Jenny, may I try your dark-colored stockings?”

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