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."
