Bedding the Babysitter Ch. 01

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 drooling over me and had to wipe your chin."

Her touch had me rattled and I couldn't even complete a rational sentence. "Um, I, I mean, I...."

She gently but firmly pushed down on my shoulders and my legs gave away as I was 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're you staring at, Jenny?" she asked, her tone saying 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 invited in a way where 'no' wasn't an option, "My vagina needs to be cleaned, why don't you clean it for me?"

I feigned reluctance, "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 'invited' into my first act of lesbian activity. I extended my tongue and made contact with her vagina.

She moaned, "Does nerdy 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 savour her unique and addictive taste. After a couple of minutes, I concentrated on her clit which made her legs tremble as she let out a loud moan.

"That's it my pet, lick my cunt good," she ordered.

Being called a 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 orgasm." She roughly pulled my head deeper into her vagina and began moving her body on my face. Always being a people-pleaser, I became a pussy-pleaser too, eagerly licking and sucking as I penetrated her vagina with my tongue.

Her moans got louder 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 asked, "Why do you hide such a beautiful body with such unflattering clothes?"

My face flushed again at getting 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," I babbled unable to complete a full thought, drowning in the compliments and in the desire to be touched.

Reaching for 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 around my erect right nipple.

"Yes, please," I whimpered at her touch.

"Yes, please, what?" she kept asking, 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, feeling a mixture of pleasure and pain.

"What else?" she asked, her finger now travelling slowly south.

Wanting her to touch me down 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 vagina lips.

I quivered and let out an uncontrolled 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 clitoris 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 all over 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 person as the volcano, dormant since the beginning of time, bubbled over. I felt fireworks in my head, chills through 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 energy 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 agree and 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 squad'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 we met 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. It was bad, wasn't it, and you were shocked?

I waited a few minutes before responding, not wanting to look too eager. I was portraying the voice of knowledgeable reason, dontcha know!

DrMeg: Hi, my dear. There is no reason to be ashamed and it certainly wasn't shocking or bad. Fantasy is natural and a great way to relieve stress.

Jenny78ph: Really? You're not mad?

DrMeg: Of course not. I fantasize too.

Jenny78ph: About?

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. You think I have a nasty mind?

DrMeg: Yes, you really do. But do not be embarrassed, be proud. By writing down your fantasy and then sending it to someone who understands you, 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?

Jenny78ph: Yes...twice.

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 experienced person seduces an inexperienced one.

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: Not to everyone, but I can also tell 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: I want you to 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 learn your true sexuality?

Jenny78ph: Yes!!!!!!!!!

DrMeg: And you will obey my instructions without hesitation?

Jenny78ph: yes, ma'am.

DrMeg: Didn't you call that cheerleader Mistress? You may address me in that fashion if you wish.

Jenny78ph: Sorry, yes Mistress, I will obey ALL your instructions.

DrMeg: Now slide two fingers in that sweet cunt of yours and come for your Mistress Megan.

DrMeg: Come now, my pet.

DrMeg: Now!!!

Jenny78ph: Kkkkkkk, Comiiiiiiiiiiing!!!!

Choosing that exact moment, I picked up the phone and called her cell number. Surprisingly, she picked it up on the fourth 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 her online Mistress Megan were one and the same.

From her hesitation, I could tell she didn't want to come over, she wanted to keep chatting with the cyber me. So I sent her 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'll pay you double."

"Sure, sure I'll do it," Jenny said, her usual can't-say-no, people-pleaser self, always sacrificing her own time to help others.

"You're a life-saver," I gushed 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, thanks, Megan, I'll 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.

Jenny78ph: ???

DrMeg: Just kidding.

Jenny78ph: Oh.

DrMeg: Actually, do you want to know a secret?

Jenny78ph: Yes.

DrMeg: I wasn't kidding. I have a woman coming over tonight I am going to use to release my stress. When you are 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.

Jenny78ph: Ok.

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. You always want to look attractive down there, even if you're the only one who knows.

Jenny78ph: OK.

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, giving Jenny enough time 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 that she must have first worn back when her legs were shorter, mocha thigh highs, and her white school blouse. You could clearly see her nylons were thigh highs.

"Wow, you look adorable, Jenny," I complimented her. "Do you have a late-night date?"

"Thanks Ms. Cameron. You look pretty too and no, I was just trying something new and didn't have time to change."

"Well it really works for you," 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'll like the one in the machine, it's a fun 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 dark 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 had 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, long enough to savour 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 couldn't do so in time.

I looked at the TV, a sly smile on my face and gasped, faking surprise, "Oops, that wasn't the movie you were supposed to see!"

She stammered, apologized and begged me "I-I-I am s-s-so sorry, Ms. Cameron. P-p-p-please don't tell my mother!"

Her red cheeks expressed both guilt from what she was doing and also the shame that came from being caught in such a compromising position. "It's ok, my dear, masturbation is natural."

"I-I-I am so, so, so sorry," Jenny continued; I found her embarrassment so cute!

"Actually, the fact that you were masturbating to a video of me and my submissive Allison is quite flattering," I mused. "What turned you on the most?"

"I-I-I don't know," she replied, clearly overwhelmed just that we were talking about such things.

"Did you find seeing me with a strap-on exciting?" I asked, moving closer. "Or was it Allison being fucked?" swearing in front of her for the first time. As I reached her, my hand grasped hers and I pulled her up and asked, "Or did you wish that you were the one on all fours getting fucked by my big strap-on cock?"

Her mouth dropped open and she froze in place, speechless. Her mouth opened and closed several times and faint sounds emerged, but no words came out. Adding to her confusion, I then leaned in and kissed her. At first it was gentle and sweet, but once she responded, tentatively at first, I used my tongue to part her lips. She responded more actively and our tongues danced inside each other's mouths. The urgency of the kiss increased as my hands slid down past her waist and beneath her skirt. The background noise of Allison coming on my strap-on enhanced the intensity of our kiss.

I finally broke away and asked, "What does my Jenny78ph want?"

"Pardon?" she asked, the significance of the words not immediately registering.

My hand traced her pussy lips through her 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 causing her so much distraction she couldn't make the obvious correlation.

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 brightened to astonishment. She asked, her words coming out stunted as my finger continued putting pressure on her clit, "Oh, um, wait, oh my God, are you Dr. Meg?"

"The one and only," I purred, as my finger slipped past her soiled panties.

"I-I can't believe it," she gasped, astonished by my revelation.

"Yes, my dear, and I am now about to relieve all your stress and satisfy all your curiosity," I promised, my finger now between but not inside her wet pussy lips.

"But how?" she asked, overwhelmed as she began seeing further implications that could stem from this sudden new level of our friendship. I had baked cookies for her when she was fifteen, and now I was touching her twat!

"I've always thought you were sexy... shy but sexy. When I overhauled your computer I searched for clues and found which sites you usually frequent," I explained, before adding with a playful smile, "By the way, for future reference you need to erase your daily history if you don't wish people like your Mom, or conniving neighbors like me, to learn all your secrets."

"Aaaaaaah," she gasped as my finger took the plunge and slowly penetrated her fevered pussy.

"Jenny, it's all right. You're a lesbian and submissive; I am a lesbian and dominant," I explained.

Jenny, still trying to get the whole picture straight in her mind with one less player now on the field, stood there in a sexual trance. Her mind was trying to process the bizarre reality currently happening around her while within, her body was begging for the attention it had long craved.