Bedding the Babysitter

Published February 23, 2024 tag category
Bedding the Babysitter

My name is Megan. I am a 35 year old single woman with a baby.

Jenny was the perfect sitter. She went to a private school and always wore the plaid skirt and knee high nylons (I found it interesting that she wore knee high nylons and not socks like most girls). She always wore her dark brown hair in pigtails or a braid and her glasses made her look like a nerd or a geek, whatever term you prefer. Anyways, Jenny was in grade 12 and had turned 18 a couple months ago when I started noticing that she was often checking out my long legs, which I always showcase, or my /breasts/large-breasts/">large breasts, which I also showcase. I started wondering if she was a dyke and decided to find out. I knew from conversations that she was always online and I decided to research what she does online. Now I should note I am computer technician and can easily find out what sites someone goes to. As I followed her online the next 3 days I learned a lot about her. She always went to a band website and played tunes online as she surfed.

Next she always checked her e-mail and had her msn on. She then would go to a teen advice site and read all the new questions and often gave advice to them or just commented. After that it varied looking up author sites, doing research for homework, etc. But she always ended the night by going to and reading sex stories. She always started on the newest stories and then would search /lesbian/lesbian-sex/">lesbian sex stories. Sometimes she clicked on titles, other times she would search using words including: submission, /submissive/">submissive, obey, school girl, etc. Some of the titles she read included: Suburban Submission, Cynthia Submission, The Professor New Toy, Bashful Betty and most interesting Seducing the Babysitter. It became clear to me that she was a submissive looking for someone to dominate her. I decided to message her about some advice she gave on the question of releasing pressure. The question was How do you release stress? She responded All girls are different. And although I can advise on almost any academic topic, I have never been able to release my stress.
I sent an email that stated: Hi, I am sorry for emailing you personally. But after reading your response, I thought I should personally respond to you. I am an expert at training people to release stress. I should note that my plan is very unorthodox and you must be very honest with me if you want true release. Love Megan.

15 minutes later Jenny replied Thanks for the e-mail. I really appreciate it. I am very curious to learn more about this. What do I do next? Jenny.
I waited until the next day to make her sweat and then emailed Dear /sweet/">sweet Jenny, if you are seriously interested, you must answer the following survey. You must be completely honest for your treatment to work. If I learn you lied to me, I will quit the treatment instantly. With that I sent the email. She responded in minutes.

Name: Jenny
Age: 18
Eye Color: Brown
Hair Color: Brown
Favourite Movie: A Walk to Remember
Favourite Band: Tegan & Sara
Three passions: Reading, writing, movies
What is your biggest stress: Getting into Harvard.
How do you deal with stress: Music, reading
How often do you masturbate: At least once a day, it too releases stress
When did you last masturbate: Last night.

What did you masturbate about: This is embarrassing but I was fantasizing about being told what to do by a cheerleader at my school. She doesnt even acknowledge I exist and she is a bitch to everyone below her, yet I cant help but think about being dominated by her.
What is your most constant fantasy: I also fantasize about being seduced by an older woman who teaches me how to please a woman completely.
Describe your sex life: My fingers, I am a virgin.
Describe your /perfect/perfect-boy/">perfect boy and/or girl: A woman who is older, powerful, understanding.
What are you wearing right now? I am in a pair of pink pajamas.

Last question: One secret that no one knows about you: I like to masturbate while wearing pantyhose and no underwear as I love the feel of silk on my legs and vagina. I guess I have a /fetish/nylon-fetish/">nylon fetish.
The survey answered all my questions and I knew she would be easy prey. My next e-mail was as follows:

Dear Jenny:
Thank you for answering the survey so thoroughly. Such honesty will lead to a complete cure to your stress problems. We will start the program today. My msn # is 456767. Please msn me as soon as you get this.
A few minutes later I got a beep.
Jen78ph: Hi. This is Jenny.
DrMeg: Hi Jenny. How are you?
Jenny78ph: Good.
DrMeg: What does 78ph mean?
Jenny78ph: 78 is a random number. Ph=pantyhose.
DrMeg: I see. Where do you live? I am an American living in Boston.
Jenny78ph: No way. I live in Boston too.
DrMeg: Very interesting. Maybe we will meet someday. Anyways, your survey made it clear you lack self-confidence. Would you say that is true?
Jenny78ph: I suppose, I am average looking and considered to be a nerd by most at my school.
DrMeg: I see. Confidence begins by looks and fashion. For example, I am wearing a garter and stockings right now, with a skirt and a tight sweater. These build my confidence as I get many looks from other /men/women-men/men-and-women/">men and women. What are you wearing?
Jenny78ph: Just jeans and a t-shirt.
DrMeg: Yet you like wearing nylons?
Jenny78ph: Yes.
DrMeg: Right now, I want you to change into nylons. Do you have any stockings or thigh high nylons.
Jenny78ph: I only have pantyhose. What are thigh highs?
DrMeg: They are stockings with an elastic top to hold them up by themselves around your thigh.
Jenny78ph: Oh, my mom has some.
DrMeg: Go put them on.
Jenny78ph: Um, ok. I will be back in a few.
About 4 minutes later.
Jenny78ph: I am back.
DrMeg: What are you wearing now?
Jenny78ph: Beige thigh highs, a long skirt and the same t-shirt.
DrMeg: Better. Now I want you to wear a skirt that is short enough for people to notice your thigh highs if you are sitting.
Jenny78ph: Ok.
A couple minutes later.
Jenny78ph: Im back and you can indeed see the top of these thing s with this skirt.
DrMeg: Good. It is all about your imagination.
Jenny78ph: I dont mean to be rude, but how will this help me relive my stress.
DrMeg: All in good time darling. Now I want you to look at yourself in the mirror. What do you see?
Jenny78ph: Um, still me, although I do look sexier.
DrMeg: Do you like the new look?
Jenny78ph: Yes.
DrMeg: Good. Now I want you to go to the mall and buy yourself your own pair of thigh highs. If possible get the following colors: black, white, pink and mocha.
Jenny78ph: Um ok. Then what?
DrMeg: While you are out pay attention if anyone notices the new you. Then msn me when you get back.
Jenny78ph: Will you be online?
DrMeg: Maybe. But keep online if you are home and we are bound to hook up.
Jenny78ph: Ok.
3 hours later.
Jenny78ph: Hi, I am back.
Jenny78ph: I got all the colors you requested and I also bought a red pair. They were on sale buy 6 get one free. So I got an extra black pair and one beige pair too.
DrMeg: Great to hear you did so well. How did you feel going out dressed like that?
Jenny78ph: Great actually. A few boys seemed to notice me and the saleslady was super nice complimenting me on my purchase.
DrMeg: I told you, how you dress is how you feel.
Jenny78ph: I did feel a little slutty though.
DrMeg: Dressing sexy does not make you slutty. Sleeping with a bunch of people makes you slutty. So I take it from your questionnaire you are a lesbian?
Jenny78ph: Um, my fantasies are about girls, but I am not groused out by boys.
DrMeg: Why older women?
Jenny78ph: I have no idea. I get excited by them more. They seem so sure of themselves. So powerful.
DrMeg: I see. Older women do have experience, unlike teen boys.
Jenny78ph: I stunning brunette hussy diana xxxxpv wouldnt know.
DrMeg: This cheerleader you fantasize about. Is she a lesbian?
Jenny78ph: No, she is dating a boy in college.
DrMeg: I see. I have a job for you tonight.
Jenny78ph: Ok.
DrMeg: Write a brief fantasy about you and the cheerleader and email it to me.
Jenny78ph: Um, I am not sure I can do that.
DrMeg: It doesnt have to be porn, just a white attractive slutty whore xxxxvie detailed fantasy. This will help me help you.
Jenny78ph: Ok, I will try.
DrMeg: I have to go help another patient. I will talk to you tomorrow.
Jenny78ph: Ok. ??
DrMeg: Goodnight.
Jenny78ph: Goodnight.

I then logged out and watched what she did online. She went instantly to literotica and searched stories. After about 20 minutes she logged out. She read a lengthy story called The Complete Submission which is an amazing story.
Next morning in my e-mail was an email from Jenny. She is more creative then I thought:

I was leaving school when I remembered I left by book I needed to finish reading in my gym looker. I walked into the gym and saw Karen naked just getting dressed. She smiled at me and said Hey Jenny, why dont you take a picture it lasts longer. I apologized and she said, Actually Jenny you can do me a favor. I say sure and she says Come here. I walk over and she kisses me. She then says, My vagina needs to be cleaned, why dont you clean it for me. I feign protest but I slowly drop to my knees and begin licking her vagina. I do it slowly, but she demands, Lezzie, suck my cunt, make me cum. She then grabs my head and shoves my face into her /wet/wet-vagina/">wet vagina. I suck on her vagina lips and try to shove my tongue inside her. She eventually has an orgasm. She then demands Get undressed. I quickly do. She then pushes me back onto the bench and devourers me. She licks me, fingers me, brings me to an intense orgasm. She then kisses me and I taste my own juices. She breaks the kiss and says, You are now my property. You will be our little /pussy/cheerleader-pussy/">cheerleader pussy pleaser. Do you understand? I nod yes. She then tells me to meet her hear again tomorrow to start my new role.