tagLesbian SexBedding the Babysitter Ch. 01

Bedding the Babysitter Ch. 01

bysilkstockingslover©

Summary: A lesbian neighbor uses the internet to seduce her innocent babysitter.

Note 1: Although originally released in September of 2010, this story was completely re-written in October of 2012, and re-polished yet again in April 2018.

Note 2: Thanks to MAB7991 (2010), LaRacasse (2012) and Tex Beethoven (2018) for editing.

BEDDING THE BABYSITTER

My name is Megan. I am a 35-year-old single woman with a two-year-old son.

My neighbor Jenny had always been my perfect sitter. She attended a private school and almost always could be found wearing its uniform plaid skirt, crisp white blouse and knee-high nylons. (I found it interesting that she wore knee-high nylons and not white socks like most girls.) She always wore her dark brown hair in pigtails or a single braid, and her glasses made her look like a nerd or a geek, whichever term you prefer. Jenny was a senior in high school and had turned 18 a couple months ago, which is when I first began noticing she was frequently checking out my long legs and large breasts. Her constant glances had me wondering if she could be a lesbian, or at least curious, and I decided to find out.

Now I should note I am a computer technician by trade, so a seduction plan practically fell into my lap. Jenny had mentioned after babysitting one evening that her computer was running slow and asked if I could look at it for her; I told her I would, but she would need to do without it for a few days.

A couple days later after doing some routine computer maintenance, I had her computer zipping along as fast as when it was new. Curious about what she did online, I checked her search history and learned she loved a site called Literotica, an erotica story site. Drilling down into her history, I could tell that she read mostly lesbian porn, and her selections mostly followed the format of young being seduced by older, with young being submissive. My suspicions were right: she was at the very least curious about being with a woman but was probably way too shy ever to do anything about it. Since I am a dominant personality, dozens of naughty ideas began bouncing around my head. I installed a tracking app (which I fondly called my 'Snoop') that would send me reports on all her internet browsing to help me plan her seduction before returning the computer to her.

I called Jenny to tell her I had fixed her computer. Atypically she came over dressed in a cute flower sundress. I asked her a couple of questions, but first I complimented her.

"Jenny, you look absolutely adorable," I complimented, placing a hand on her bare shoulder.

"Thanks," she whispered timidly, not used to being admired. Although she was very pretty, she didn't seem to know it. Her fashion sense, or lack thereof, plus her self-confidence, or lack thereof, were hiding her true natural beauty.

"Do you have a boyfriend?" I asked, moving my hand away. A successful seduction requires reading the prey and deciding whether to go fast or slow, and I decided hers would definitely not be a wham-bam-thank-you-ma'am seduction.

"No," she said, unable to look me in the eye.

"Really!" I said, acting surprised. "You're such a beautiful young woman, Jenny. I can't believe the boys aren't lining up to date you."

"I've never even had a date," she admitted.

I can't believe that," I objected, "you're way too pretty not to have had three or four boyfriends already."

"Well, I'm not sure I even want to date."

"Well, they can be exhausting," I joked.

She giggled, "That's what I hear."

"So even though you're gorgeous, you've never had a boyfriend. How about a girlfriend?" I asked, opening the door for the plan already formulating in my head.

Jenny's face went flaming red: she was either not used to receiving such compliments or, as I was hoping, was embarrassed because of her secret attraction to women. She stammered, "W-w-what? N-n-no, I...."

"I was just kidding, Jenny," I reassured her, my hand again going to her arm fleetingly. "Although there's nothing wrong with liking girls." After a long pause I added, again building on the complex web of seduction I was creating, "I certainly do."

"You do what?" Jenny asked, her eyes suddenly big.

"I only date women now," I admitted, then adding, "after that asshole of an ex-husband left Max and me I decided to swing the other way, and it's been a very satisfying decision."

"Y-y-you are a lesbian?" Jenny stammered, clearly flummoxed by this startling piece of information.

"You didn't know?" I asked.

"N-n-no," she said, her face the darkest red possible.

"I'm sorry if that makes you uncomfortable," I said.

"No, no, it's fine," she replied, "I just found it surprising, is all."

"I find," I said, hoping to enhance her curiosity, "that only women can understand what women need." After another pause I joked, as I handed her computer to her, "Well, that's probably in the way-too-much-information-for-you category. Here's your computer; it's now working as well as the day you bought it."

"Thank you," she said, her mind clearly elsewhere. "What do I owe you?"

"How about free babysitting one day soon?" I asked.

"Sure, any time, Ms. Cameron," she said.

Once she was gone, I smiled at our conversation and at the potential.

*****

During the next three days my snoop app taught me a lot about her. She always went first to a music website and loaded some tunes to play in the background as she surfed. Next, she frequently checked her email and switched on her MSN chat program. She then would frequently go to a teen advice site, read all the new questions and often offer pertinent advice or just make sympathetic comments. After that it varied: looking up author sites, doing research for school, etc. But she always ended her evening by going to www.literotica.com and reading lesbian sex stories. She would begin with the newest stories and then search through the overall collection of lesbian stories. Sometimes she just clicked on titles that caught her eye, other times she would use the search engine, filtering by tags such as: submission, submissive, obey, schoolgirl, etc. Some of the titles she had read included: "Suburban Submission", "Cynthia's Submission", "The Professor's New Toy", "Bashful Betty" and most interesting, "Seducing the Babysitter". It became clear to me that whether she knew it or not, she was a submissive looking for someone to take charge of her. I decided to message her about some input she had given on the question of releasing stress. The question was, "How do you release stress?" She had responded, "All girls are different. And although I can comfortably advise on almost any academic topic, I have never been able to release my own stress."

I sent her an email that stated:

Hi, I beg your pardon for emailing you personally, behind the scenes as it were. But after reading your response about stress, I thought I could best respond to you in private. I have much experience in helping people to release/relieve their stress and perhaps I may be of service to you. I should advise you up front that my treatment methods are very unorthodox and you must be completely honest with me if you wish to obtain any lasting release. Love Megan.

15 minutes later, Jenny replied:

Thanks Megan, for the email, I really appreciate it. I am very curious to learn more about your methods. What do I do next? Love Jenny.

My next email tried to dig deeper and begin building her trust:

What kinds of things stress you out?

Her response didn't appear for almost an hour:

Lots of things. I guess the usual high school things: being popular, getting good grades, scholarship writing and relationships, I guess.

Trying to dig deeper, I asked a question while reassuring her she was not unlike most teenagers:

Those are very common teenage stresses. Does one of them cause you particular stress?

It was only seconds before she responded:

It is just hard to be yourself in high school, I guess.

Having begun an initial relationship with her, I tried to set her up for my plan:

"If you wish I can help you, but I need to know more about you. About what makes you tick."

Her response was immediate, and clearly she was waiting at her email:

"What do you need to know?"

I replied with a warning, setting up my web of seduction, hoping she would take the bait:

I will send you a questionnaire, but be warned that I ask some potentially uncomfortable questions. Only if you respond with complete honesty will I be able to assist you with more than superficial advice like you can find on that teen site.

As I expected, she replied almost immediately:

Please send me the survey and I promise to answer it honestly.

I told her I would send the questionnaire soon, and since I was winging it, I spent an hour composing the pertinent questions. A seduction is a temperamental thing, and I could either coax her in or scare her off. Finally happy with my questions, I wrote her:

"Dear sweet Jenny, if you are seriously interested, you must answer the following questions. You must be completely honest for my treatment to be effective. If I learn you have lied to me, I will halt your treatment instantly."

After double-checking my questions, I sent her the email. She responded in minutes.

Name: Jenny

Age: 18

Eye Color: Brown

Hair Color: Brown

Favorite Movie: A Walk to Remember

Favorite Band: Tegan & Sara

Three passions: Reading, writing, movies

Your biggest stress: Getting into Harvard.

How you deal with stress: Music, reading

How often you masturbate: At least once a day, it too releases stress

When you last masturbated: Last night.

What you masturbated about: This is embarrassing, but I was fantasizing about being told what to do by a cheerleader at my school. She doesn't even acknowledge I exist and she is a bitch to everyone beneath her, yet I can't help but fantasize about being dominated by her.

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 ideal boy and/or girl: A woman who is older, assertive, understanding.

What you are wearing right now: I am in a pair of pink pajamas.

Last item: One secret that no one knows about you: I like to masturbate while wearing pantyhose and no underwear as I love the silky feelings on my legs and vagina. I guess I have a nylon fetish.

Jenny's responses had answered all my questions and I knew she would be easy prey. My next email was as follows:

Dear Jenny:

Thank you for answering all my questions so frankly. Such honesty will lead to a complete cure to your stress problems. We will start the program immediately. My msn tag is DrMeg. Please message 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. Your answers to my questions make it clear you lack self-confidence. Would you agree that is true?

Jenny78ph: I suppose, I am average-looking and considered to be a nerd by most of my classmates. I'm also pretty much a loner.

DrMeg: I see. Confidence begins by loving yourself. Therefore I believe how you present yourself and what you wear (both of which greatly influence others' perception of your looks) can build your self-confidence.

Jeny78ph: Really???

DrMeg: Yes. For example, I am wearing a garter and stockings right now, under a skirt and a tight sweater. These build my confidence as I get many admiring looks from other 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 but not pantyhose. Do you have any stockings or thigh high nylons?

Jenny78ph: I only have pantyhose. What are thigh highs?

DrMeg: Stockings with an elastic top to hold them up by themselves around your thigh.

Jenny78ph: Oh, my mom has some.

DrMeg: Can you borrow a pair from her room?

Jenny78ph: Yes, she is not home and anyway she doesn't mind if I borrow her things.

DrMeg: Go put a pair on, my dear.

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. But now I want you to put on a skirt that is short enough for people to notice your nylons are thigh highs if you are sitting.

Jenny78ph: Now?

DrMeg: Yes, now, my dear.

Jenny78ph: Ok...BRB!

A couple minutes later:

Jenny78ph: I'm back and OMG you can indeed see the tops of these things with this skirt.

DrMeg: Good. This particular exercise is all about your own perceptions. You appear to others the way you see yourself.

Jenny78ph: I don't mean to be rude, but how will this help me relieve 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: If you like yourself, everything else follows.

Jenny78ph: Is it that simple?

DrMeg: Yes, confidence is built through loving yourself and being comfortable with who you are, both of which encourage you to understand that you deserve good things and are attractive.

Jenny78ph: I suppose, I have always been insecure about how others see me.

DrMeg: Let's test my theory.

Jenny78ph: How?

DrMeg: Do you trust me?

Jenny78ph: For some reason, yes.

DrMeg: Good. So dressed exactly as you are now, I want you to go to the mall and buy yourself your own collection of thigh highs. If possible, get the following colors: black, white, pink and mocha.

Jenny78ph: Um, ok, but everyone will see my entire stockings.

DrMeg: Yes, they will. They will see the new Jenny.

Jenny78ph: That they will! <giggles>

DrMeg: While you are out, pay attention to whether anyone notices the new you. Then message me when you get back.

Jenny78ph: Will you be online?

DrMeg: Maybe. But remain online while you are home and we are bound to hook up.

Jenny78ph: Ok.

I looked out the window and watched: a few minutes later she came out, dressed as instructed and hopped into her car. She was as obedient and submissive as I thought she'd be.

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 for buy six get one free. So I got an extra black pair and a beige pair too.

DrMeg: Great to hear you did so well. How did you feel going out dressed like that?

Jenny78ph: Great, actually. At first I was really self-conscious, but after getting over the original anxiety, I felt a rush. I felt sexy, something that usually doesn't correlate with my perception of myself. A few boys seemed to notice me, one even whistled, surprising me when I liked that, 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 answers to the questionnaire you are a lesbian?

Jenny78ph: Um...I don't know...my fantasies are about girls, but I am not grossed out by boys.

DrMeg: Why older women?

Jenny78ph: I have no idea. I get more excited by them. They seem so sure of themselves. So powerful.

DrMeg: I see. Older women do have experience, unlike teenage boys.

Jenny78ph: I wouldn't 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 task for you tonight.

Jenny78ph: Ok.

DrMeg: Write a brief fantasy about yourself and the cheerleader and email it to me.

Jenny78ph: Um, I am not sure I can do that.

DrMeg: It doesn't have to be porn, just a detailed fantasy and go wherever your imagination takes you. It will help me to help you.

Jenny78ph: Ok, I will try.

DrMeg: I have to go meet another patient. I will talk to you tomorrow.

Jenny78ph: Ok. : )

DrMeg: Goodnight, my dear.

Jenny78ph: Goodnight.

I logged out and watched what she did online. She went immediately to Literotica and browsed through some stories, all about girls submitting to dominant women and getting off on the experience, before selecting one. After about 20 minutes she logged out. She had read a lengthy story called "The Complete Submission" which I read also, which was an amazing submission story.

Next morning I found an email from Jenny. She was WAY more creative than I'd thought:

Dear Dr. Meg,

You said I didn't have to write porn, but you also said I should go wherever my imagination went and it kinda came out like porn. I hope it won't shock you too badly, but I want to do what you say. If this is bad, please say and I'm sorry and I'll try to do better.

I was leaving school when I remembered I left a book I needed to finish reading in my gym locker. I walked into the gym and saw Karen naked just getting dressed. She smiled at me and said, "Hey Jenny, why don't you take a picture, it lasts longer?"

I was shocked she even knew my name. I apologized with a stammer, my cheeks instantly turning red, "S-s-sorry."

She asked, "Actually Jenny, you can do me a favor."

"Sure," I asked, just excited she was conversing with me.

"Come here," she said, waving me over with a smile that I couldn't read.

Report Story

bysilkstockingslover© 86 comments/ 1058211 views/ 834 favorites

Share the love

Report a Bug

Next
3 Pages:123

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel