Bedding the Babysitter Ch. 02bysilkstockingslover©
Disclaimer 1: Of course everyone in this story is at least 18.
Disclaimer 2: If you want to know how 18-year old babysitter Jenny became the submissive slave of neighbor Megan, please read part one. Without further adieu part two:
Last night I had seduced my 18-year old babysitter. Today I hoped to make her greatest fantasy come true. So after my ex-husband came and picked up our son for his usually every second weekend custody time, I msn'd Jenny. It was just after lunch the following day.
DrMeg: How is Jenny this fine afternoon?
Jenny78: Very good mistress.
DrMeg: That is good to hear? No regrets about last night's events?
Jenny78: None! :)
DrMeg: Ready for your training to continue?
Jenny78: Yes mistress.
DrMeg: Are you dressed already?
Jenny78: Of course.
DrMeg: Come on over, we will start researching
Karen before we head out to begin your transformation.
DrMeg: Of course. A new look. We are going to make you irresistible to Karen.
Jenny78: But what if she doesn't like girls?
DrMeg: Well, let's find out.
DrMeg: Get over here now.
Jenny78: Yes mistress.
Jenny arrived in the exact same outfit as yesterday. An adorably hot plaid school skirt, a white school blouse that showcased her nice perky breasts, dark mocha thigh high stockings and, sadly, runners. I led her upstairs and I slid out of my black leather skirt to reveal a black silk panties and matching black thigh highs. I said, "Jenny come sit under my desk and please me while I research your little dream cheerleader for you?"
"Yes mistress," Jenny replied and quickly she went to work with her eager little tongue as I began typing.
I gave out a soft moan as I asked, "Jenny, what is Karen's last name?"
Jenny looked up at me, so cute, from between my legs and said, "Pepper." She then went right back to pleasing my already damp pussy. I requested, "Jenny dear, go nice and slow."
I believe she said, "Yes mistress," as she responded, her tongue never leaving my cunt.
As I research, I learned that Karen came from a well off family, lived in a massive house and she was an only child. On facebook, which by the way, you should protect yourself from much better than most do, I learned she was a redhead, with green eyes, she was short at 5'2, but her breasts looked quite large. I then created a new facebook account under the fake name of Sarah Conners and I asked her to be a friend, with a note that I was a girl researching cheerleader popularity (again you really should protect yourself from online predators). 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 lots about her. She was very sarcastic, she hated her mother, she loved getting compliments, reveled in them really, and was quite spiteful. Comments like "Mrs. Wicks is a complete bitch" or "Did you see what Sara wore today, it made her look 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 store in town) and based on her status she was working right now.
All this time, Jenny kept slowly licking my pussy, nibbling ever so gently on my pussy lips. I moaned and said, "Good girl my little teenage pussy pleaser. Slide a finger in your mistress's pussy and finger fuck me as you lick me." She obeyed and I just leaned back and enjoyed the oral stimulation. When I was close, I grabbed her face and pushed it into my pussy and just held her pretty face in my pussy as I quavered a small, but intense orgasm. As I regained my senses, Jenny still between my legs, I noticed that Karen had responded to my questions. I pulled Jenny up and said, "Let's read how your little dream cheerleader responded to my questions:
This survey is completely confidential and just part of an article I am writing for a national magazine about cheerleaders in America (Please answer all questions honestly as it is integral to the validity of this article and the role cheerleaders play our schools):
Name: Karen Pepper
Cheerleader Role: Captain
Years as Cheerleader: 4
Do you do hazing among the cheerleaders? 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, going to gym class without any bra or panties, flirting with a teacher, stealing an item at the mall, and we always finish with having the new cheerleaders make out with each other.
What is the greatest perk to being a cheerleader? I can't choose only one, because there so many perks. I already have a scholarship for next year, I can have any hot boy I want, I get to wear my outfit any wear I want and I am treated like royalty by most of my peers and teachers.
Do you think you get breaks from your teachers
because you are a cheerleader? Sure. All I ever have to do for the male teachers is give my puppy-dog look or showcase my legs a little extra and I get what I want usually...actually make that always. The female teaches are a bit tougher, but again, very few want to mess with us cheerleaders as we have a reputation of being quite powerful.
How do you choose your squad? It is based on look, fitness and social status. This may sound rude, but if you are not attractive and thin, you probably should not be a cheerleader. Now on occasion we take on a girl who is not in great social standing if we think we can train her, but usually it is not worth the effort as they never really fit in to our social circle. I know it is shallow, but it is true.
Some schools are cancelling cheerleading programs because of the rise of teenage pregnancies, has that been a concern among 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, as our past captains have too.
Last question, is there any lesbian activity among your squad? Um...yes. Between cheerleading camp, nighs in hotels during competitions and post-game celebrations there is a fair amount of lezbo action. Plus, as girls dating incompetent teenage boys, although mine is in college, sometimes the only way to really get of is by a woman's touch.
Any other comments: Please send me a copy of your final article. Kisses.
Thanks for participating in this survey!!!
"Well Jenny, I think it is time to go shopping," I said as I got dressed. She followed and we headed to the mall. I could see Jenny getting nervous as we drove to our first stop...a beauty salon. We went inside and I had Jenny get the full treatment. She had a leg wax, a manicure, a pedicure, a tanning session, facial and finally she got a new hair-do, followed by having her make-up done.
When Jenny looked in the mirror, now dressed back in her school girl outfit, she looked like a confident college girl on the prowl. She smiled, but said, "How can I ever repay you for this?"
"Don't worry, this will not cost either of us any money," I responded slyly.
"Really," Jenny asked confused, her pure innocence still so charmingly adorable.
"Really" I responded. "Actually I think it is time to pay for your makeover." I paused, grabbed her hand and led her to the backroom. As we reached the office, I walked in and greeted the owner, my best friend since college, Krystal, and gave her a hug and a tender kiss.
Krystal, at almost 6 feet, towered over Jenny as we walked over to her and said, "So, this is your new recruit. She is very pretty."
Jenny stuttered, "T-t-thanks." Her hands slightly trembled as she fidgeted with her newly manicured hands.
Krystal put her hand on Jenny's chin and lifted her face up so they were looking eye to eye. "Jenny," she started, "Every girl who works here is a submissive slave of mine, does that surprise you?"
Jenny looked to be attempting to process this information when Krystal continued, "For example, your manicure and pedicure were done by Carley and Jen. Those two were high school best friends who 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, she is a 4th year med student originally from Japan and easily one of the prettiest girls in the entire world, although she does not believe it. She is also the most obedient little slave I have ever had. I picked her up in a move theatre for some arts film I went to one day. Half way through the film, I simply moved seats to sit beside her, there were maybe 6 people in the theatre, and I put my hand on her leg. When she did not react negatively to my move, I simply whispered in her ear 'Open your legs honey.' She did without hesitation and I simply fingered her to orgasm in the theatre. She came quickly and shockingly loudly, so loud the few other people there looked back to see this Japanese girl cum on my fingers. I then sucked her juices from my finger and whispered, 'You are the most beautiful girl I have ever seen. I want to see you again. If you do too, here is my card, be at my salon tomorrow at 6.' I kissed her, handed her my card and left. Of course, she showed up the next day and has now become a great little cunt pleaser.
The others have stories too my sweet, but you will learn them over time if you wish. Now I have a job opening here on weekends is you wish, as a sales clerk; you would work the till, do final clean-up and so forth. Are you interested?"
Jenny's face lit up a touch as she said, "That would be great."
Krystal went and sat on her desk, lifted up her skirt and said, "Are you ready for your on job training?"
I laughed, Jenny blushed, as she walked over to Krystal. Jenny moved and bent awkwardly to Krystal's completely shaved pussy. Jenny began pleasing her new boss as I watched. Part way through I went behind my little vixen and gently squeezed her ass and slowly slid a finger inside her, but not enough for her to get off. Jenny eventually brought Krystal to an orgasm and I pulled my finger out of her wet pussy.
Krystal said, "Well, I definitely think you are hired," she said as she stood up. Can you be here for training next Friday evening?"
"Yes," Jenny responded, her lips shiny with love juice.
"Great," said Krystal. "Be here at 5. We will train you till 9 and then you can come to our usual Friday night social which usually goes quite late," she paused for emphasis, "If you get my drift."
"Ok," said Jenny, slightly nervous.
Krystal gave a little chuckle as she said, "Alright go see Kirsten again and get your make-up toughed up. You look like you just ate pussy."
I laughed and chit chatted with Krystal as Jenny got a quick touch up. As I returned to the front, Jenny was just finishing getting redone and I heard the 40ish Kirsten telling Jenny, "I can't wait to eat that young pussy of yours Jenny."
I chuckled as I pulled a completely beautiful and red faced Jenny back to the car. In the car, I said, "Well Jenny, two pussies in two days, you are turning into quite a little lesbian slut aren't you?"
Jenny probably would have blushed more if she could, as she responded "I can't believe I just licked a complete stranger."
"Did you enjoy it?"
"Yes," Jenny responded. "I just wanted to make her happy. I hate every being a disappointment."
I sighed slightly. "Oh Jenny, we need to work on your self-esteem. You are a beautiful girl, a very smart girl and a very nice girl. Don't you know that? Krystal does not just hire anyone, she saw something in you. Just like I did."
"Thanks," Jenny responded, although her tone of voice implied she did not completely believe it.
"We are here," I announced as we arrived at our next stop, Mill's Boutique. Jenny, I assumed, had no idea who worked here.
"Mill's Boutique?" Jenny questioned as we arrived. "Isn't this place where the rich and famous go?"
"I suppose it is. Come on sweetie, I have a surprise for you."
We got out of the car and walked to the front door. I paused and said, "Before we go in I should stress that if we go in, there is probably no turning back."
"What do you mean?"
"Well you can continue coming over to my place, either way, and you have a job with Krystal so you can still have lots of opportunity to be submissive, but if you walk through these doors and I go through with my plan, you will almost for sure, 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, I don't understand."
"Do you know who works at this store?"
Jenny's face went white.
"If you go in there, I plan to treat you as my lesbian slave in front of her."
"Oh," Jenny whispered.
"Jenny, I don't want to do anything to you that you are not ready for. So if you say no, you will not hurt my feelings or disappoint me. But if you say yes, I am almost positive you will be eating Karen's pussy very, very soon ."
Jenny considered this, really considered it and finally said surprisingly upbeat, "I trust you mistress. I will never obey anything you ask of me and if you think this is a good idea, then I do too."
"Great Jenny," I responded, "Let's go have some fun."
I grabbed her hand and we walked into the Mill's Boutique. Now I should say that my divorce as well as my job keeps me financially well off, I am not a millionaire, but I live a very comfortable life, so I could afford the absurd prices this boutique charged. The shop itself was not that busy with only a couple people looking at clothing. One was a slightly overweight girl with what I assumed was her mother looking at wedding dresses; while the other was a clearly trophy wife looking at cocktail dresses and treating her saleswoman with obvious distain. I did not see Karen at first which worried me a bit, as we walked over to the cocktail dress section of the shop. As I looked around, we were fortunate to have Karen come over to assist us.
"Good afternoon maam, "Karen said, dressed in a very classy black skirt, pantyhose, 3 inch black boots and a white blouse. "Can I help you with anything?"
I smiled and said, "Yes, you probably can. I am going to a special gala tonight for charity and I need an outfit for myself and my friend here.
The outfits must look sexy , but not slutty."
Karen asked for our sizes and left to grab some outfits. I looked at Jenny and asked, "Are you ready to begin Operation Karen?"
Jenny laughed, as this seemed to break the tension, although she said slightly hurt, "She did jot even notice me."
"Well you do look different. You went from your conservative unfaltering attire to a revealing sexy attire. Plus with make-up on, you easily could pass for 21, which we will try to do tonight," I said teasingly.
"What is tonight?"
"That is for me to know and you to find out," I responded coyly. At this moment I saw Karen coming back with a few dresses and said, "Operation Karen is under way."
Karen arrived to both of us laughing and said, "I choose a few dresses I think you will like. " I tried on three different dresses that were all good, 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 said, "I think I have just the thing."
Karen left again and I said to Jenny, "This is going to be easier than I thought."
"How so?" asked Jenny.
"Just watch. I do need to know if you want her to be your little slave or do you want to be hers?"
"I want to be her slave," she said shyly and without hesitation.
"I thought so," I confirmed just as Karen returned. She handed me a gold gown that was long enough to hide my thigh high stockings, but with a generous enough slit to allow glimpses of my stocking tops for anyone really paying attention. I gave her a kiss on the cheek and said, "This looks excellent." I grabbed it and went to the changeroom. After putting on the dress I came out and looked in the mirror. I spent a bit of time analyzing the outfit before saying, "These black stockings do not match this dress, Jenny can I try your dark colored stockings."
Jenny responded "Sure," and we both took off our stockings. As Jenny gave me her stockings, I sat down on a soft bench and demanded "Jenny dear, please put the stockings on for me."
I gave Jenny back her stockings and I lifted up my leg so Jenny could slowly slide on the thigh high mocha stocking. I looked at Karen and saw that she was watching vey intently. Jenny switched legs and put on the second stocking.
When she was done, I stood up and looked at myself in the mirror. I said, "Yes that is much better. " I looked at Karen and said, "Can you see my panties outline with this dress?"
Karen looked closely and said, "Well if you are really looking I suppose it is slightly noticeable."
I then said to Jenny, "Honey, come and take off my panties for me."
Jenny moved towards me as I lifted up my dress. Jenny ever so slowly slid my panties down my legs. Karen's eyes never looked away from the scene.
"So Karen what do you think? Do I look good enough to eat?"
Karen finally blushed as she responded, "You look radiant?"
"Thanks, but you never really answered my question."
"Um," she paused.
"Do I," I began as I walked closer. "Look good enough" I continued now right in front of her. "To eat," I finished seductively. I starred into her eyes waiting for an answer.
"Um yes, you look good enough to eat," she whimpered.
I leaned into her ear and whispered, "Thanks." I blew hot air into her ear and then went back to the mirror. "This is perfect," I said. "What do you have for my little Jenny?"
Karen having regained her senses responded, "Of course. I think that if you are going to wear gold, she should probably wear something red."
"Good call," I responded. "You know your fashion sweetie."
Karen left and I said to Jenny, "I have her horny as hell right now."
Jenny replied, "I know, my pussy got wet just watching you tease her."
"Wait until you see what I am going to get her to do next?" I teased as Karen returned with a gorgeous red little number. I grabbed it and said, "Jenny dear, why don't you go and try this one."
Jenny grabbed it and went to the change room. I asked Karen, "So I hate to be blunt, but I must ask, are you a lesbian?"
Karen shook her head no as she said, "No, no. I have a boyfriend in college."
"Oh," I said, "That is too bad, you are a very pretty woman and my little Jenny would love to be able to please you."
Before Karen could respond, Jenny came out looking radiant in a sleeveless cocktail dress that just reached her knees. I looked it over and said, "Well this dress clearly needs black stockings." I grabbed my stockings that were neatly folded on a stool and handed them to Karen. "Would you please put these on for her?"
Karen grabbed the stockings from my hand without question and somewhat awkwardly slid them onto my young slave's legs. When she was done, Jenny , showing some new found confidence, posed seductively, in the mirror. It was awkward and adorable. It was at this moment that Karen made a stunning revelation as she asked Jenny "Wait a minute, I know you. Don't you go to my school?"
Jenny, slightly embarrassed and nervous responded, "Yes, we have math together."
Karen continued, "I am failing that class, me and numbers don't really go well together." She paused before continuing, "You look really different all dressed up, I kind of thought of you more as a..."
Karen contemplated the right word choice when I stepped in and said, "Geek?"