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.
“That’s it my pet, lick my cunt good,” she ordered.
Being called pet had my own vagina getting wet and I eagerly continued pleasing the most beautiful girl I knew in school. I swirled my tongue around her clit, I sucked it in my mouth. I was addicted to her unique taste and never wanted to have this moment end.
Suddenly her hand on my head, she demanded, “Fuck you lezzie-slut, suck my cunt, make me cum.” She pulled my head roughly deeper into her vagina and began moving her body on my face. Always being a people pleaser, I became a pussy-pleaser, eagerly licking and sucking as I penetrated her vagina with my tongue.
Her moans increased and I was soon rewarded with the sweetest taste God had created as her juices flooded out of her onto my tongue, lips and face. I continued to quench my unquenchable thirst wanting more and more as I drowned in my submission and in her perfection.
Once her orgasm had run its course, she looked down at me and ordered, “Get undressed.”
I stood up and obeyed, hands trembling and began to unbutton my blouse.
“Hurry up, slut,” she snapped impatiently.
I again obeyed, a mixture of anticipation and trepidation colliding in my mind. Once naked, I never felt more vulnerable as she looked me over. She commented, “Why do you hide such a beautiful body with such unflattering clothes.”
My face flushed again at a compliment from the girl I had fantasized about forever, the girl that made me reconsider my sexuality. “I-I-I don’t know.”
“You don’t know how sexy you are, do you?” she asked, moving towards me.
“Um, I,” babbled unable to complete a full thought, drowning in the compliments and in the desire to be touched.
Reaching me, she asked, her finger slowly moving between my breasts, “Do you want me to eat your cunt?”
“Yes,” I whispered, almost inaudible.
“Pardon,” she asked, her finger slowly gliding to my erect right nipple.
“Yes, please,” I whimpered at her touch.
“Yes, what?” she asked, her fingers pinching my nipple.
“Aaaaah, please lick my vagina,” I moaned, giving myself to her.
“Vagina,” she laughed softly, her fingers meandering to my other nipple. “What else can you call that sweet box of yours?”
I paused, I almost never swore, but her fingers pinching my nipple had me distracted and horny. “My pussy,” I moaned again, a mixture of pleasure and pain.
“What else?” she asked, her finger now slowly travelling south.
Wanting her to touch me there, to lick me, I answered, “My cunt, please touch my cunt.”
“Good girl,” she moaned, leaning forward and taking my breast in her mouth as her finger traced my wet pussy lips.
I quivered and let out an uncontrollable moan.
She pushed me onto the bench and moved between my trembling legs. Looking up at me, she asked, “Tell me what you want, my pet.”
“Eat my cunt,” I demanded. “I need to come so baaaaaad.”
“Tell me you are a lezzie-slut,” she demanded back, flicking my clit with her tongue.
My whole body quaked with one touch and I declared my sexuality without hesitation. “I’m a lezzie-slut. I love licking your beautiful pussy and will be your lezzie-slave who drops to her knees anytime, anywhere to get just a taste of your perfection.”
“Fuck, that is hot,” she purred, burying her face between my legs. As her tongue did slow paintbrush strokes on my pussy my breathing got heavy. Usually, it takes a while to come, but in a couple of minutes I could feel the volcano eruption of lust bubbling inside.
“Oh god, fuck my cunt is burning,” I moaned, as she slid a finger inside me.
She hooked her finger inside my inferno and began tapping on my g-spot.
I had spasm after spasm like an epileptic as the volcano, dormant since the beginning of time, bubbled over. I felt fireworks in my head, chills to my entire body and a euphoria I didn’t know possible as my orgasm hit.
“Aaaaaaaaaaaaaaaaaaah, fuck, fuck, fuck, fuck, fuck,” I screamed, babbling incoherently as my brain went blank and sexual enlightenment poured through me.
She pulled her fingers out of me as the never-ending orgasm continued through my body. She leaned in and kissed me. I could taste my own juices on her lips; it was so naughty, so sweet and so natural.
Sadly, all good things must come to an end and she broke the kiss. Looking into my eyes, she smiled and said, “You understand you are now my property. You will be our little cheerleader pussy pleaser. Do you understand?”
I nodded yes, knowing I would do anything to taste her again, to feel that feeling of utopia I just experienced.
“Tomorrow, you are going to become the cheerleading team’s personal pussy-pleaser,” she promised.
“Yes, Mistress Karen,” I replied.
I was impressed. She had written a fantasy that was Literotica worthy and had given me a plethora of insight into her young, submissive mind.
That night she was on MSN clearly stressed about what she had sent me.
Jenny78ph: Are you there?
Jenny78ph: That story was so embarrassing; I can’t believe I sent it. I have been stressed about it all day thinking about what you must think of me.
I waited a few minutes before responding, not wanting to look to eager myself.
DrMeg: Hi, my dear. There is no reason to be ashamed. Fantasy is natural and a great way to relieve stress.
DrMeg: Of course. I fantasize too.
DrMeg: Many things. Your fantasy turned me on a lot and told me so much about you. I enjoyed how real the fantasy was, you could probably write for Literotica with that nasty mind of yours.
Jenny78ph: Really? OMG, I am SO embarrassed.
DrMeg: Yes really. But do not be embarrassed, be proud. By writing your fantasy, you have allowed your pent up frustrations to be released and your true sexual desire to come alive. I assume you got off last night after writing it?
DrMeg: So I learned a lot from your fantasy, by the way.
Jenny78ph: Like what???
DrMeg: You are very smart, yet insecure.
Jenny78ph: True and true.
DrMeg: You stress easily and have no real outlet to release your stress, so I assume you either read or watch a lot of porn online.
Jenny78ph: OMG! <blushing>
DrMeg: Am I wrong?
Jenny78ph: No, I read a lot online.
DrMeg: A lot of what?
Jenny78ph: Porn, mostly lesbian porn.
DrMeg: And I am guessing it is lesbian porn where one person seduces another.
Jenny78ph: Yes <blushing>
DrMeg: and I am also guessing it is one where one woman dominates and controls another.
Jenny78ph: Am I that transparent?
DrMeg: And you are the submissive one, because after being high strung and stressed at school or work, you want to just let go and be told what to do.
Jenny78ph: OMG, yes! <mortified blushing>
DrMeg: Finger yourself for me, my dear.
Jenny78ph: Yes, ma’am.
DrMeg: Good girl. It’s now time for the next step in your treatment. Do you want an online Mistress to guide you as you attempt to discover your true sexuality?
DrMeg: And you will obey my instructions without hesitation?
Jenny78ph: yes, ma’am.
DrMeg: Didn’t you call that cheerleader Mistress?
Jenny78ph: Sorry, yes Mistress, I will obey ALL instructions.
DrMeg: Now slide two fingers in that sweet cunt of yours and come for Mistress Megan.
DrMeg: Come now, my pet.
Jenny78ph: Kkkkkkk, Comiiiiiiiiiiing!!!!
At that exact moment I picked up the phone called her cell number. Surprisingly, she picked it up on the forth ring. Her breathing was stilted and it was obvious she had obeyed my instruction.
“Hi, Ms. Cameron,” she said, her voice raspy.
“You ok?” I asked, although I knew exactly why she was breathing like she was.
“Sorry, just finished working out,” she covered impressively.
“I hate to ask last minute, but I desperately need a babysitter tonight,” I said, adding, “any chance you can be a dear and come over?” I shook my head when I realized I had used the word ‘dear’. Luckily she didn’t make the correlation that her next door neighbor Megan and the online Mistress were one and the same.
By her hesitation, I could tell she didn’t want to, she wanted to keep chatting with cyber me. So I sent a quick message.
DrMeg: Sorry, but I have to get going. We will continue our conversation tomorrow, is that clear, my dear?
On the phone, I pleaded, “Sorry, Jenny, but I am so desperate, please I will pay you double.”
“Sure, sure,” Jenny said, her usual can’t say no, people pleaser self, always sacrificing her time to help others.
“You are a life-savor,” I said thankfully. “Can you be here in an hour?”
“Sure, Ms. Cameron,” she agreed.
“You can call me Megan,” I said, dropping another hint of my double identity.
Jenny said, “OK, Megan, I will be there at eight.”
“Eight is great,” I quipped, before adding, “See you then.”
I hung up and saw Jenny had continued our cyber conversation.
Jenny78ph: That is ok, I have to go babysit for my neighbor in an hour.
DrMeg: Fun. I am going out right away. I have a date with my girlfriend.
Jenny78ph: Like a friend who is a girl or a ‘girlfriend’.
DrMeg: Truthfully, she is a slave of mine. I have a few women who service me sexually.
DrMeg: Just kidding.
DrMeg: Actually, do you want to know a secret of mine.
DrMeg: I wasn’t kidding. I have a woman coming over tonight who I am going to use to release my stress. When you are ready and more confident you will be able to release your stress through sex too.
Jenny78ph: Not sure I will ever be that confident.
DrMeg: I promise we will find your happy place. You have already begun the transition.
DrMeg: I want you to do something for me.
Jenny78ph: Of course.
DrMeg: When you go to babysit, I want you to wear the shortest skirt you have, and thigh highs that match.
Jenny78ph: To babysit?
DrMeg: Yes. Are you going to do as I say?
Jenny78ph: Yes, sorry for questioning you.
DrMeg: It’s ok. I have to go and shave for tonight. Do you shave your special place?
Jenny78ph: I trim it.
DrMeg: Be sure it is nice and trimmed before you go out tonight.
DrMeg: I must get going. I will talk to you later tomorrow.
Jenny78ph: Ok, thank you…Bye.
I got ready for my fake date. I would go out for an hour or so for my plan to kick into action. I was dressed in a black leather skirt, beige stockings and a red blouse. Jenny arrived dressed in one of her plaid school skirts, mocha thigh highs, and her white school blouse. You could clearly see she was wearing thigh highs.
“Wow, you look very adorable, Jenny,” I complimented her. “Do you have a late night date?”
“Thanks Miss Cameron. You look pretty too and no I was just trying something new and didn’t have time to change.”
“Well it really works,” I said, gently squeezing her shoulder. “I’ve got a hot date. Max is already asleep, so you can watch a DVD if you want. I think you will like the DVD in the machine it is a great movie.”
“Ok, have fun,” she said her usual bubbly self.
“Oh, I will,” I said ever-so-coyly.
After I left, I drove to a nearby adult store and picked up a new smaller strap-on I hoped to use on my cute, babysitter later tonight. After grabbing a quick bite to eat, I drove home and snuck in the back door quiet as a mouse.
From the kitchen, I checked in on my babysitter.
She was on the couch, her legs open and her hand assumedly pleasuring herself as she watched a scene of me fucking the pussy of a pretty 21 year old coed I seduced a while ago. The girl, a sweet submissive volleyball player named Allison, was screaming “Yes mistress, fuck me, bang my tight pussy.” I allowed the scene to go on for a couple of minutes and long enough to hear Jenny’s soft moans before I decided it was time for me to ‘return home.’ I snuck back out the back door and came in the front door. I closed it silently to avoid startling my in the throes of self-pleasure babysitter. The sounds of the DVD echoed through the house, “Yes mistress, pound me, I’m coming.” When I entered, Jenny scrambled to cover herself, but could not in time.
I looked at the TV, a sly smile on my face and said faking surprise, “Oops, that was not the movie you were supposed to see.”
She stammered, apologized and begged me “I-I-I am s-s-so sorry, Miss Cameron. P-p-p-please don’t tell my mother.”
Her red cheeks were both undeniable guilt of what she was doing and yet also the shame that went with being caught in such a compromising position. “It is ok, my dear, masturbation is natural.”
“I-I-I am so, so, so sorry,” Jenny continued, her embarrassment so cute to me.
“Actually, the fact that you are masturbating to a video of me and my submissive Allison is quite flattering,” I mused. “What turned you on?”
“I-I-I don’t know,” she replied, clearly overwhelmed by the conversation.
“Was it me with a strap-on?” I asked, moving closer. “Or was it Allison being fucked?” I asked, swearing in front of her for the first time. As I reached her, my hand took hers in mine and I pulled her up and asked, “Or did you wish that was you on all fours getting fucked by my big strap-on cock?”
Her mouth dropped open and she was speechless. Her mouth went to speak, but no words came out. Adding to her confusion, I leaned in and kissed her. At first, it was gentle and sweet, but once she responded, tentative at first, I used my tongue to part her lips. She again responded and our tongues danced inside each other’s mouth. The urgency of the kiss increased as my hands slid down her waist and underneath her skirt. The background noise of Allison coming enhanced the intensity of our kiss.
I finally broke the kiss and asked, “What does my Jenny78ph want?”
“Pardon?” she asked, the words not immediately connecting with the reality.
My hand traced her pussy lips on top of her very wet panties. “Hmmmm, you are very wet, Jenny78 pantyhose.”
She let out a soft moan from my touch. “H-h-how do you know my MSN name?”
“Oh, Jenny, Jenny, Jenny. Have you not figured it out?” I smiled, my finger tapping her protruding clit.
Her breathing increased, and my finger was clearly causing her to be so distracted she could not make the obvious correlation.
Finally, I asked, “What is my first name, Jenny?”
“M-M-Megan,” she moaned. I watched her face and her lips as she moaned with desire. It was so adorably cute as the light bulb came on and her face went to astonishment. She asked, her words came out stunted as my finger continued putting pressure on her clit, “Oh, um, wait, oh my God, are you DrMeg?”
“The one and only,” I purred, as my finger slipped underneath her soiled panties.
“I-I can’t believe it,” she said, still clearly bewildered by my revelation.
“Yes, my dear and I am about to relive all your stress and confirm all your curiosities,” I confirmed, my finger now between, but not in, her wet pussy lips.
“But how?” she asked, clearly overwhelmed by this new knowledge.
“I always thought you were sexy, shy but sexy. When I fixed your computer I searched for clues and saw the sites you usually frequent,” I explained, before adding with a playful smile. “By the way, for future reference you should erase your daily history so people like your Mom or conniving neighbors don’t learn all your secrets.”
“Aaaaaaah,” she gasped as my finger slowly penetrated her fevered pussy.
“Jenny it is all right. You are a lesbian and submissive; I am a lesbian and dominant,” I explained.
Jenny still trying to get the whole ordeal straight in her mind stood there in a sexual trance. Her mind trying to process the bizarre reality that was currently happening while her body begged for the attention it had long craved.
“Jenny, I know exactly what you need.”I said gently, “even if you don’t. You are submissive and a people pleaser, as your naughty story clearly showed. You want to explore your sexuality but don’t know how to even start. I am here to help you, Jenny.”
Jenny looked me directly in my eyes. I smiled. She looked tentative, yet I knew she had already made up her mind.
“If you want Jenny, I will teach you how to be a good submissive pet and how to pleasure a woman properly and in return be pleasured,” I continued, my finger now deep in her just lingering inside her warmth.
“Please,” she whispered.
“Please what?” I asked, my mouth leaning into her ear.
“Please, don’t stop,” she again whispered, such words difficult for her to say.
“Please don’t stop what?” I questioned, pushing her deeper into admitting her desires and needs. I responded by moving my finger ever so slowly in her.
“P-p-please, don’t stop fingering me,” she admitted, her breathing getting heavier.
“Do you want to come?” I asked, nibbling on her ear.
“God, yes,” she moaned.
“I do need to make something very clear, my dear,” I whispered, my tongue darting in and out of her ear.
“Whaaaat?” she asked, clearly distracted by my finger in her pussy and my tongue in her ear.
“If you want we will make love today. I will take you to new levels of euphoria you have only imagined. You will taste your first pussy and I will fuck you,” I explained. Suddenly I wondered if she was a virgin. I asked, “Jenny, are you a virgin?”
“Yes,” she admitted, as if such a declaration was something to be ashamed of.
“It’s ok, Jenny,” I soothed. “It is nothing to be ashamed of. You are confused about your sexuality, and tonight I will help you discover your true sexuality.”
“Kkkkkk,” she whimpered, my finger causing her great pleasure, a constant teasing distraction.
“But if you submit to me tonight, I will expect you to be my submissive. If you agree, you must obey every order I give without hesitation. I do not tolerate disobedience. I know what you need and crave, but I expect unconditional loyalty in return.”I explained, my finger touching, ever so briefly, her g-spot. Her legs trembled and I added, assuming her true submissive nature would take over, “If you do not want to submit to me, if you are not ready to agree to my terms, you may leave. We will pretend this never happened, I will still pay you for the night and you will be free to continue to babysit Max if you are comfortable with knowing what you now know.”
Her mind was clearly processing all my terms, all my words and all the things I was doing to her body. If there was an internal struggle between good girl Jenny and sexually curious Jenny it was a short one.
Going for broke, confident I had read her right, I said, backing up a few feet to admire her, “My sweet dear Jenny, it is time. If you are want me to become your mistress you simply need to undress for me.”
Jenny’s eyes never left mine as she obeyed my order instantly and started to unbutton her blouse. Her hands trembled slightly, but slowly she tossed her blouse on the floor. Her small, perky breasts peaked out from her white lace bra.
“You are very beautiful Jenny,” I encouraged. “Please take off the skirt.”
Jenny obeyed sliding the skirt down her stocking clad legs. She was now in front of me in her bra, white panties and mocha thigh highs. I looked down and saw her toenails were painted purple. She looked so adorable and good enough to eat.
I walked back to her and as my hand touched her skin she shivered. She looked pleadingly into my eyes, secretly begging for me to please her. I moved in for a kiss so soft, just brushing her tender lips. I then moved to her ear. I nibbled on her ear lobe, my hot breath flowing into her ear. She quivered and let out a soft moan. I then whispered, “Jenny.”
She whispered back, almost inaudible, “Yes.”
“Are you ready?”
I moved down her neck, giving gentle soft kisses. I got to her breasts and unhooked her bra. I licked, nibbled and sucked on her perky firm breasts. I teased her nipples; I splattered her with butterfly kisses. Her breathing again increased in desire. My tongue slid down her belly. I reached her panties and slowly, seductively, slid them off. Without instructions she lifted her foot to allow them to fall to the floor. The ripe young lesbian-to-be stood before me naked, except for a pair of thigh high stockings. I gave her one gentle lick on her newly trimmed pussy and allowed my tongue to roam down her left leg. I lifted her foot to my mouth and took each delicate toe into my mouth. Her breathing got heavier. I moved back up to her delicious pussy and gave her one more long, wide lick, before sliding down her right leg and replicated the toe sucking. I moved up, kissing behind her knee, her mid thigh, her clit, up her belly and then her lips. She eagerly kissed me back, moaning in my mouth with a new determined hunger.
I broke the kiss, reached for her hand and led her to my bedroom. I laid her on my bed and kissed her again. Our tongues twisted and turned, danced and twirled. I moved back down and asked, “Does my dear want her pussy licked?”
“Yes,” she moaned.
“Tell me what you want, my pet,” I purred, my hot breath on her pussy.
“I want you to lick me,” she moaned.
“Where?” I asked, again pushing her to say the words.
“My pussy, please lick my pussy Megan,” she pleaded, an intense desperation in her voice which was adorably sexy.
“Good girl,” I purred and leaned forward to lick her virgin pussy. Her nectar was so sweet and she was already dripping wet. I knew her first orgasm would come quick as her moans implied she was already close to climatic bliss. I licked her with long, wide strokes and her moaning increased. I could tell her orgasm was imminent as I took her swollen clit in my mouth and sucked it in.
She screamed, “Oooooooo myyyyyyyyyy god.”
Her orgasm quaked through her and the shy, reserved babysitter came sexually alive. As she writhed and screamed from her first real sexual orgasm, I continued pleasing her, already attempting to build a second orgasm in my new pet even as the first one had not yet subsided. I continued licking, sucking and nibbling her clit, while I slid a finger inside her warm hole and pumped it in and out. Jenny screamed, “Oh my god, don’t stop, yes, yes, it feels so good.”
I continued to heat her up, get her revved for more and after a few more minutes of licking and fingering, I suddenly stood up.
She whimpered, “Noooooo.”
“Get on all fours,” I ordered, adding, “And don’t you dare touch your cunt, is that understood?”
“Kkkk,” she moaned, obeying the order and clearly desperate to come again.
I went downstairs; pulled out the new strap-on I had bought for this very occasion and returned to a hungry suddenly insatiable teenager.
Once back in the room, I slipped out of my outfit, while my babysitter watched on with bated breath. Like Jenny, I was soon naked except for my stockings. I asked, “Does my pet babysitter want to get fucked?”
“So bad,” she answered, staring at the cock in my hand.
I put the harness on and sauntered over to her. “Has Jenny ever sucked a cock?”
“No,” she said, shaking her head.
“Does she want to suck mine?” I asked, my cock now directly in front of her.
“Yes, ma’am,” she answered.
“When we are alone, I am your Mistress, Jenny. Is that understood? You do want a Mistress, don’t you?” I asked.
The hesitation was brief before she responded as expected, “Yes, I understand, Mistress Megan.”
“Good girl,” I purred, knowing that a true submissive lives and breathes for compliments. “Now suck my cock, my pet.”
She leaned forward and took my plastic cock in her mouth. Watching my cute, shy, sweet teenage babysitter slowly bobbing up and down on my cock was one of the hottest moments of my life. Anytime I have turned a straight girl, or pulled a bi-curious girl into the world of lesbian submission I get a joy and sense of accomplishment I cannot explain. I don’t do it just for the personal pleasure (although that is very rewarding too), I do it to liberate young woman from the sexual expectations that hold them back. Jenny wanted to be a lesbian, Jenny is submissive and I just pushed her over the edge to discover her true nature, to accept her true sexuality. Jenny started slow, but soon was moving faster and I briefly imagined she would be a great cocksucker if she was ever to try to play the straight card.
Finally, I pulled my cock out of her perfect mouth and asked, “Jenny, my pet, are you ready for your mistress to fuck you.”
She looked me straight in the eye and surprised me for the first time. “Please, fuck me mistress. I need your cock in me so fucking bad,” she begged, her foul language so out of character.
I joined her on the bed and moved behind her. I rubbed my cock up and down her pussy lips and was again surprised when she moved back taking my cock inside her.
“You naughty little slut,” I quipped playfully.
“Oh God,” she moaned, “Please fuck me Mistress.”
Never one to deny such a request, I put my hands on her hips and began to slowly slide my cock in and out of her sweet pussy.
She was so drenched, my cock filled her completely and as I started pumping in and out she began to get animated. The shy, reserved nerd, begged, “Fuck me, harder, harder. Fill my pussy completely. Make me your whore.”
Watching her complete transformation was so hot and I again obliged my body thrusting into her. Her body got involved too and she began meeting my thrusts, attempting to get my cock deeper inside her.
As her moans increased, I demanded, “Your pussy is a cunt, my slut. Beg for me to fuck your tight cunt.”
“Oh God, Mistress, pound my cunt with your cock, it feels sooooo good,” she moaned.
We continued fucking for a few more minutes, sweat pouring off of both of us as our bodies collided and became one.
Finally, her breathing was undeniable and she screamed, “I’m coming again, Mistress, oh my God, oh my God, yes, yes, fuuuuuuuuck.”
She collapsed forward and I continued pumping her pussy from a new deeper angle. Her orgasm clearly was giving quiver after quiver of pleasure as I slowed my fucking and watched her, my cock buried deep inside my no longer a virgin babysitter.
Finally, I pulled out of her beautiful cunt, took my shiny with her juice cock off and went and got a couple of glasses of water. I returned and she had not moved an inch. I handed my exhausted pet a glass of water and sitting up she downed the whole glass. She looked me straight in the eye and said, “Let me please you. I want to please you.”
Joining her on my bed, I smiled and promised, “Jenny. You will be pleasing me many, many times. Now crawl between my legs and please your Mistress.”
Eagerly, Jenny repositioned herself and crawled between my stocking-clad legs. She looked at my completely shaved pussy, my pussy lips slightly wet and my swollen clit with the awe of an innocent virgin.
“Go ahead, my pet,” I purred, “Lick Mistress’s cunt.”
She actually smiled and again surprised me. “I have wanted to do this for a long time.”
“Do what, lick pussy?” I asked.
“No, lick your pussy, Mistress,” she answered, admitting, “I have fantasized about you for forever.”
It was my turn to be surprised. “Really?” I asked, suddenly not completely in control.
“Really, really,” she smiled, leaning forward and extending her tongue. I moaned on contact, my pretty babysitter between my legs licking me so sexy. For a pussy licking rookie, she was very good. She licked, she sucked, she probed with her finger. She was like an explorer trying to taste, search and learn about every aspect of my cunt.
After a few minutes of her eager tongue, I was close and moaned, “I’m close, my pet slut, sooooo close.”
She took my clit in her mouth and put intense pressure on it and began shaking her head from left to right. This was something I had never experienced and I began breathing heavy, my own orgasm now imminent. “Oh, yes, Jenny, fuck that is so good, more, more.”
Out of the blue, she surprised me yet again as she slid a finger in my ass. It triggered the explosion of my orgasm and I flooded my juices all over my adorable cute babysitter’s face. “Oh fuck, you nasty sluuuuuuut, I’m comiiiiiing.”
She continued teasing my ass, sucking on my clit and fingering my pussy while my orgasm waved through me. The intensity of the orgasm more powerful than usual, I finally had to push her away. “Fuck, that was amazing, my pet,” I whimpered, as I closed my legs and allowed the last of the orgasm to pulse through.
She moved up and leaned beside me smiling like a kid on Christmas morning. “I read that last move in a story online.”
I laughed. “Well, keep reading that was amazing.”
She asked, her smile fading to serious, “Does it always feel this amazing?”
“It can. Although you should understand, that I was very gentle with you tonight. I won’t always be,“ I warned.
“I understand. I want you to dominate me. I want you to treat me like a slut,” she answered, the words out of her sweet lips seeming so sinfully delicious. “All my fantasies are of being treated like a slut. Being forced to do things I would never do on my own.”
“You are going to make a great slave,” I comforted back, kissing her again. Once the tender kiss was broken, I look at the clock and realize it has been almost two hours. I kiss her again and said, “You understand that I will share you with friends. I will take you to places you have not even imagined.”
Her eyes went big, but she replied like a good submissive. “I understand and eagerly await what you have in store for me.”
I got on all fours and said, deciding to test her utter loyalty, “Lick my asshole.”
“Yes mistress,” she replied, crawling behind my ass. She pulled my ass cheeks apart and after a brief hesitation leaned forward and began licking my dark dime. Such an eager submissive, she worked hard to slip her tongue deep inside my ass. Her eagerness to please was so fucking adorable and sexy.
Her submission keeping me horny, I ordered, “On your back, my pussy pleaser.”
She again obeyed and I straddled her face. Without instruction, she licked my pussy and time stood still as my new pet pleasured me. Finally, a second orgasm was building and I began rubbing my pussy all over her sweet face until I came, flooding her face again with my cum.
Getting off of her, I smiled and said, “You look absolutely adorable with your face shiny with cunt cum.”
“Thanks, Mistress,” she replied, like a good girl.
“Wait here,” I ordered and returned a minute later with my camera. “Let’s take a picture to remember this special day.”
I thought she may balk on this suggestion, but instead sat up and posed. I snapped a few pictures of her cunt cum covered face, her make-up smeared.
Putting the camera down, I came over to the bed and said, “It is getting late.”
She looked at the clock and sighed. “I suppose it is.”
“Are you free tomorrow?” I asked.
Excited, like a girl being asked out by a boy she was crushing on, she said, “Yes, yes.”
“Well, I am going to take you out for a makeover tomorrow,” I smiled.
“Where?” she asked.
I just shrugged and said, “You’ll see, but wear the same thing you did today.”
“Yes mistress, “she said, standing up.
She got dressed, I kissed her one last time and she went home.
My head spinning with naughty possibilities, I smiled to myself. ‘Tomorrow was going to be fun’….