Bedding the Babysitterbysilkstockingslover©
Summary: A lesbian neighbor uses the internet to seduce her innocent babysitter.
Note: Although released in September of 2010, this story was completely re-written in October of 2012.
Note 2: Thanks to MAB7991 and LaRacasse for editing.
BEDDING THE BABYSITTER
My name is Megan. I am a 35 year old single woman with a two year old child.
Jenny was the perfect sitter. She goes to a private school and always wears 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 wears 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 a senior in high school and had turned 18 a couple months ago when I started noticing that she was often checking out my long legs and large breasts. Her constant glances had me wondering if she may be a lesbian or at least curious and decided to find out.
Now I should note I am a computer technician and a seduction plan practically fell in my lap. Jenny mentioned while babysitting one evening that her computer was running slow. Jenny asked if I would look at it for her; I told her I would but it would take a few days.
A couple of days later, after doing some routine computer maintenance I had her computer running as fast as when it was new. Curious of what she did online, I searched her search history and learned she loved a site called Literotica, an erotica story site. Going deeper into her history, I could tell that she read mostly lesbian porn and they mostly followed a similar format of young being seduced by older, of young being submissive. My suspicions were right; she was at the very least curious about being with a woman, but way too shy to do anything about it. Being a dominant personality, dozens of naughty ideas bounced around my head. I installed a tracking system that gave me access to all her internet browsing before returning the computer to her a few days later.
I called Jenny to tell her I had fixed her computer. She came over dressed in an adorable flower sundress and I was still planning her seduction. I asked her a couple of questions, but first I complimented her.
"Jenny, you look absolutely adorable," I complimented, putting my hand on her bare shoulder.
"Thanks," she whispered, clearly not used to being noticed. Although she was very pretty, she didn't know it. Her style, or lack thereof, was hiding her true natural beauty.
"Do you have a boyfriend?" I asked, moving my hand away. A successful seduction requires reading the prey and knowing whether to go fast or slow and this was definitely not a wham-bam-thank-you-ma'am type of seduction.
"No," she said, unable to look me in the eye.
"Really!" I said acting surprised. "You are such a beautiful young woman, Jenny. I can't believe the boys are not lining up to date you."
"I have never even had a date," she admitted.
I can't believe that," I said, "you are way too pretty to have had three or four boyfriends already."
"Well, I am not sure I even want to date."
"Well, they are exhausting," I joked.
She giggled, "That is what I hear."
"So you have never had a boyfriend. What about a girlfriend?" I asked, opening the door for the plan already formulating in my head.
Jenny's face was flaming red; she was either not used to such compliments or, as I was hoping. embarrassed because of her attraction to women. She stammered, "W-w-what? N-n-no, I...."
"I was just kidding, Jenny," I saved her, my hand again going to her arm fleetingly. "Although there is nothing wrong with liking girls," after a long pause, I added, again building on the complex web of seduction I was creating, "I do."
"You do what?" Jenny asked, her eyes suddenly big.
"I only date women now," I admitted, adding, "after that asshole of an ex-husband left me and Max, I decided to swing the other way and it has been a very good decision."
"Y-y-you are a lesbian?" Jenny stammered, her eyes clearly bewildered by this piece of information.
"You didn't know?" I asked.
"N-n-no," she said, her face the darkest red possible.
"Sorry, if that makes you uncomfortable," I said.
"No, no, it is fine," she replied.
"I find," I said hoping to enhance her curiosity, "that only women understand what women need." After a pause, I joked, as I handed her computer to her, "Well, that is probably in the way too much information for you category. Here is your computer it is as working as good 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?" 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 I learned a lot about her. She always went to a music website and played tunes online as she surfed. Next she always checked her e-mail and had her MSN chat program on. She then would go to a teen advice site, read all the new questions and often gave advice to them or just comment. After that it varied looking up author sites, doing research for homework, etc. But she always ended the night by going to www.literotica.com and reading sex stories. She always started on the newest stories and then would search lesbian sex stories. Sometimes she clicked on titles, other times she would use the search engine searching words such as: submission, submissive, obey, school girl, etc. Some of the titles she 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 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 have lots of experience at helping people to release stress. I should advice you that my treatment 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? Love Jenny.
My e-mail back tried to dig deeper and build trust:
What things stress you out?
Her response didn't come back 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 she was not unlike most teenagers:
Those are very common teenage stresses. Do any of them cause excess stress?
It was only seconds before she responded:
It is just hard to be yourself in high school, I guess.
Having built a brief relationship with her I tried to set her up for my plan:
"If you want I can help you, but I need to know more about you."
Her response was immediate and clearly she was waiting at her e-mail:
"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 do ask some potentially uncomfortable questions. Only through complete honesty will I be able to really help you with more than superficial advice like you get on that teen site.
As 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 spent an hour thinking of the right things to ask. The potential seduction is a temperamental thing and could either pull 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 work. If I learn you lied to me, I will quit the treatment instantly."
After double checking my questions, I sent the email. She responded in minutes.
Eye Color: Brown
Hair Color: Brown
Favorite Movie: A Walk to Remember
Favorite 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 doesn't even acknowledge I exist and she is a bitch to everyone below her, yet I can't 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 ideal 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 silky feeling on my legs and vagina. I guess I have a nylon fetish.
Jenny's responses answered all my questions and I knew she would be easy prey. My next e-mail was as follows:
Thank you for answering all my questions so thoroughly. Such honesty will lead to a complete cure to your stress problems. We will start the program today. 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?
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 answers to my questions 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 of my classmates.
DrMeg: I see. Confidence begins by loving yourself. Therefore, I believe how you look and what you wear builds self-confidence.
DrMeg: Yes. 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 and women. What are you wearing?
Jenny78ph: Just jeans and a t-shirt.
DrMeg: Yet you like wearing nylons?
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: Can you get some from her room?
Jenny78ph: Yes, she is not home.
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. Now I want you to wear a skirt that is short enough for people to notice your thigh highs if you are sitting.
DrMeg: Yes, now, my dear.
A couple minutes later.
Jenny78ph: I'm back and OMG you can indeed see the top of these things with this skirt.
DrMeg: Good. It is all about your perception. You become to others how 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?
DrMeg: If you like yourself, everything else takes care of itself.
Jenny78ph: Is it that simple?
DrMeg: Yes, confidence is built through loving yourself first and being comfortable with who you are.
Jenny78ph: I suppose, I have always been insecure about how others see me.
DrMeg: Let's test my theory.
DrMeg: Do you trust me?
Jenny78ph: For some reason yes.
DrMeg: Good. So dressed in exactly what you are wearing now, I want you to go to the mall and buy yourself your own pairs of thigh highs. If possible get the following colors: black, white, pink and mocha.
Jenny78ph: Um, ok, but they will all see my stockings.
DrMeg: Yes they will. They will see the new Jenny.
Jenny78ph: That they will <giggles>
DrMeg: While you are out pay attention if anyone notices the new you. Then messge 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.
I looked out the window and watched; a few minutes later when she came out, dressed as instructed and hopped into her car. She was as obedient and submissive as I thought she would 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 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. At first I was really self-conscious, but after getting over the original anxiety, I felt a sudden rush. I felt sexy, something that usually doesn't correlate with my perception of myself. 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 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 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 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.
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 doesn't have to be porn, just a 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, my dear.
I 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 I read also, which was an amazing submission story.
Next morning I found an email from Jenny. She was WAY more creative than I thought:
I was leaving school when I remembered I left a 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 don't you take a picture it lasts longer."
I was shocked she 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 that she was conversing with me.
"Come here," she said, waving me over with a smile that I couldn't read.
I walked over and was stunned when she said, "You have been checking my body out all semester, haven't you, Jenny?"
My face ruby red now, I again stammered, trying to hide my guilt, "N-n-no, I have not."
"Don't lie," she smiled, putting her hand on my shoulder. "You have been literally been drooling over me."
Her touch had me rattled and I couldn't even complete a rational sentence. "Um, I, I mean, I...."
She gently, but firmly, pushed on my shoulders and my legs gave away as I lowered onto my knees. "It was really hot today, Jenny and cheerleading practice was exhausting. I feel so diiiiirty," she said, stressing the word dirty.
My face was directly in front of her vagina and I was staring at it lost in thought.
"What you starting at, Jenny?" she asked, her tone implying she knew exactly what I was staring at.
I forced myself away from her vagina and looked up past her large breasts and into her eyes.
Smiling knowingly, she instructed, "My vagina needs to be cleaned, why don't you clean it for me?"
I feigned protest, "Um, I-I-I am not a lesbian."
"Neither am I. I love fucking boys. But girls are way better at licking pussy," she smiled, reaching for my head and pulling me into her sweet sex.
I gave no resistance as I was led into my first act of lesbian activity. I extended my tongue and made contact with her vagina.
She moaned, "Does little Jenny like my pussy?"
I stammered, already addicted, "Y-y-yes."
I licked slowly up and down on her vagina pussy lips, trying to please her and savor her unique and addictive taste. After a couple of minutes, I concentrated on her clit which made her legs tremble and she let out a loud moan.