Bedding the Babysitter Ch. 01

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 trabzon escort 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..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