Bedding the Babysitter Ch. 01

"Jenny, I know exactly what you need," I told her gently, "even if you don't. You are submissive and a people pleaser, as your naughty story clearly demonstrates. You want to explore your sexuality but don't even know where to start. I'm here to help and guide you, honey."

Jenny looked directly into my eyes. I smiled. She looked tentative, yet I knew she had already made up her mind.

"If you wish me to Jenny, I will teach you how to be a good submissive pet and thus how to pleasure a woman properly and in return be pleasured thoroughly yourself," I continued, my finger now deep inside her, just lingering in her warmth.

"Please," she whispered.

"Please what?" I asked, my mouth close to her ear.

"Please, don't stop," she again whispered, such words difficult for her to say.

"Please don't stop what?" I pressured, pushing her deeper into admitting her desires and needs. I encouraged further responses by moving my finger ever so slowly inside her.

"P-p-please, don't stop fingering me," she elaborated, her breathing getting heavier.

"Do you want to come?" I asked, nibbling on her earlobe.

"God, yes," she moaned.

"Then I need to make something very clear, my dear," I whispered, my tongue darting in and out of her ear.

"Whaaaat?" she asked, distracted by my finger in her pussy and my tongue in her ear.

"If you wish, we will make love today. I will take you to levels of euphoria you have so far 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 her, "Jenny, are you a virgin?"

"Yes," she admitted, as if such a declaration was admitting something shameful.

"It's ok, Jenny," I soothed. "That's nothing to be ashamed of. You're uncertain about your sexuality, and tonight I will help you discover and confirm your true sexuality."

"Kkkkkk," she whimpered, my finger causing her great pleasure but also great need, a constant teasing distraction, but also a goad.

"But I need to warn you: if you submit to me tonight, I will expect you to become my permanent submissive. If you surrender to me, you must henceforward obey every order I give without hesitation, and I do not tolerate disobedience. I know what you need and how to provide what you crave, but in return I expect unconditional loyalty," I explained, my finger touching, ever so briefly, her g-spot. Her legs trembled and I added, knowing her true submissive nature was taking over, "If you do not wish 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 double for tonight as promised and you will be free to continue to babysit Max if you're comfortable doing so knowing what you now know."

Her mind was clearly processing all my terms 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 brief one.

Going for broke, confident I was reading her correctly, I released her and backed up a few feet to say, "My dear sweet Jenny, it is time for you to decide. If you wish for me to become your Mistress, you simply need to undress for me."

Jenny's eyes never left mine as she began to obey my order instantly by reaching for a button and slowly beginning to unbutton her blouse. Her hands were trembling slightly as she tossed the blouse on the floor. Her small, perky breasts peeked out from her white lace bra.

"You are very beautiful, Jenny," I encouraged. "Please remove the skirt."

Jenny obeyed, sliding the skirt down her stocking-clad legs. She was then standing in front of me in her bra, white panties and mocha thigh highs. I looked down and saw her toenails were painted purple while her lipstick was light pink... but never mind fashion nuances for now. Overall, she looked so adorable, and good enough to eat!

I stepped back to her and as my hands grasped her shoulders, she was shivering. She looked pleadingly into my eyes, silently begging for me to pleasure her. I moved in for a soft kiss, just brushing her tender lips. I then moved to an ear. I nibbled on her earlobe, my hot breath flowing into her ear. She quivered and let out a soft moan. I then whispered, "Jenny..."

She whispered back, almost inaudibly, "Yes?"

"...are you ready?"

"Yes."

I moved down her neck, trailing gentle soft kisses. When my kisses reached her breasts, I unhooked her bra, allowing it to fall to the carpet. I licked, nibbled and sucked on her perky, firm breasts. I teased her nipples; I splattered her with butterfly kisses. Her breathing again increased from her desire. My tongue slid down her belly. I reached her panties and slowly, seductively, drew them down until they fell around her ankles. Requiring no urging, she stepped out of them. The ripe young lesbian-to-be now stood before me naked except for a pair of thigh-high stockings. Kneeling, I gave her one gentle lick across her freshly trimmed pussy and allowed my tongue to roam down her left leg. I lifted her foot to my mouth and through the transparent silky fabric of her stocking, took each delicate toe into my mouth. Her breathing became heavier, more laboured. I moved back up to her delicious pussy and gave her one more long, wide lick, before gliding down her right leg and replicating my toe-sucking on that foot. I moved up, kissing behind her knee, her mid-thigh, around to her clit, up her belly and then to her lips. She eagerly kissed me back, moaning into my mouth with a new, determined hunger.

I broke the kiss, took her hand and without a word from either of us, led her to my bedroom as she followed pliantly. I lay her on my bed and kissed her again. Our tongues twisted and turned, danced and twirled. I moved back down to her special place and asked, "Does my dear pet want her pussy licked?"

"Yes please," she moaned.

"Tell me what you want, my pet," I purred, my breath hot 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 quickly as her moans told me she was already close to a major stress release. I licked her with long, wide strokes and her moaning increased. I could tell her orgasm was imminent so I grasped her swollen clit between my lips and sucked it in.

She screamed, "Oooooooo myyyyyyyyyy gaawwd!"

Her orgasm quaked through her and the shy, reserved babysitter came sexually alive. As she writhed and screamed from her first intense orgasm, I continued pleasing her, already attempting to build a second orgasm in my new pet even as the first hadn't 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 was screaming, "Oh my god, don't stop, yes, yes, it feels so good!"

I continued to heat her up, getting her revved for more, stoking her need for another climax, but after a few more minutes of licking and fingering, I suddenly stood up, abandoning her to her unreleased urges.

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 even though she was desperate to come again.

I went downstairs and pulled out the new strap-on I'd bought for this very occasion and returned to my hungry, newly insatiable teenager.

Once back in the bedroom, I slipped out of my clothing while my babysitter looked on impatiently, but without complaint. I was soon as naked as she was except for our stockings. I asked, "Does my pet babysitter want to get fucked?"

"So bad," she finally felt at liberty to say, staring at the cock in my hand.

I fastened the harness in place and sauntered up to her. "Has Pet Jenny ever sucked a cock?"

"No," she said, shaking her head.

"Does she want to suck mine?" I asked, my anatomically correct 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 truly do, Mistress Megan."

"Good girl," I purred, knowing that a true submissive lives and breathes for approval. "Now suck my cock, my pet."

She leaned forward and took my plastic cock in her mouth. Watching my cute, shy, sweet teenaged babysitter slowly bobbing up and down on my cock was one of the hottest moments of my life. Anytime I turn a straight girl or pull a bi-curious girl into the world of lesbian submission, I experience a joy and a sense of accomplishment I cannot explain. I don't do it just for the personal pleasure (although that is certainly one reward), I do it primarily to liberate young women from the sexual stereotypes that hold them back. Jenny wanted to be a lesbian, Jenny was submissive, and I had just pushed her over the edge to discovering her true nature, to accepting her true sexuality. Jenny had begun slowly, but soon began moving faster and I briefly imagined she could become a great cock sucker if she were ever to try playing 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 badly," she begged, the combination of her unexpected foul language coupled with her customary proper grammar absolutely delicious!

I moved her to all fours and joined her on the bed, placing myself behind her. I rubbed my cock up and down her pussy lips and was again surprised when she leaned back abruptly and forecefully, taking my cock inside her.

"You naughty little slut," I quipped playfully.

"Oh God, yes I am," she moaned, "Please fuck me, Mistress."

Never one to deny such a request, I put my hands on her hips and slowly began to slide my cock in and out of her sweet pussy.

She was so drenched my cock easily filled her completely, and as I started pumping in and out she began to get animated. The shy, reserved nerd begged, "Fuck me, harder, even 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 also got involved and she began meeting my thrusts, attempting to get my cock deeper inside her.

As her moans increased I demanded, "Your pussy is called a cunt, my slut. Beg for me to fuck your tight cunt."

"Oh God, Mistress, please pound my dirty cunt with your cock, it feels sooooo good," she moaned.

We continued fucking for a few more minutes, sweat pouring off both of us as over and over our bodies crashed together and became one.

Finally, her breathing had become urgent panting 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 was continuing through quiver after quiver of pleasure as I slowed my fucking and watched her, my cock still buried deep inside my no-longer-virgin babysitter.

Finally I pulled out of her beautiful cunt, removed my shiny-with-her-juices cock and went for a couple of glasses of water. I returned and she hadn't moved an inch. I handed my exhausted pet a glass of water and after sitting down on the edge of my bed, she downed the whole glass. She looked me straight in the eye and said, "Allow me to please you, Mistress; I want to pleasure your cunt."

Joining her on the bed and lying back, I smiled up at her and promised, "Jenny, you will be pleasuring my cunt many, many times. Now crawl between my legs and begin to please your Mistress."

Eagerly, Jenny crawled between my stocking-clad legs. She looked at my completely shaved pussy, my slightly wet pussy lips, and my swollen clit with the awe of an innocent virgin.

"Go ahead, my pet," I purred, "Lick your Mistress's cunt."

She smiled and again surprised me. "I've wanted to do this for a long time."

"Do what, lick someone's pussy?" I asked.

"No, lick your pussy, Mistress," she answered, admitting, "I've fantasized about you for like, 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 sexily. For a pussy-licking rookie, she was very good. She licked, she sucked, she probed me with her fingers. She was like an explorer breaking into new territory, wishing to taste, search and learn about every aspect of my special place.

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 into her mouth and put intense pressure on it and began shaking her head from left to right. This was a technique I had never experienced and I began breathing heavily, my own orgasm now imminent. "Oh, yes, Jenny, fuck, that is so good, more, more!"

Out of the blue she surprised me yet again by sliding a finger in my ass! It triggered the explosion of my orgasm and I flooded my juices all over my adorably 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 surged through me. The intensity of the orgasm was so much more powerful than usual that I finally had to push her away. "Fuck, that was amazing, my pet," I whimpered, as I drew my legs together and allowed the last of the orgasm to subside.

She moved up and lay beside me, smiling like a kid on Christmas morning. "I read about 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. But please don't hold back from doing whatever you wish with me: I want you to dominate me. I need you to treat me like a filthy slut, I know that now," she answered, the unhesitant words flowing past her sweet lips sounding so sinfully delicious. "All my fantasies have always been of being treated like a slut, being forced to do kinky things I would never dare to do on my own."

"You're going to make a great slave," I promised her, kissing her again. But once the tender kiss was broken, I looked at the clock and realized it had been almost two hours. I kissed her again and told her, "You must also understand that I will share you with my friends. I will take you to places you have never even imagined, and this time I mean physical places and sometimes people you've never met."

Her eyes went big, but she pledged me like a good submissive. "I understand Mistress, and eagerly await whatever you have in store for me."

I faced away from her, got on all fours and suddenly ordered, deciding to test her utter obedience, "Then lick my asshole, my pet."

"Yes Mistress," she replied without hesitation, crawling up to my ass. She pulled my ass-cheeks apart, and after a brief pause to admire the view, she leaned forward and began licking my dark dime. Such an eager submissive, she worked hard to poke her rigid tongue deep inside. 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 requiring any instruction, she again licked my pussy and time stood still as my new pet pleasured me. Finally my second orgasm was building and I began rubbing my pussy all over her sweet face until I came, flooding her face once again with my cum.

Climbing off her, I smiled and said, "Your sweet face looks absolutely adorable, all shiny with my cunt cum."

"Thanks, Mistress," she chirped companionably, like a good girl. She was being appropriately deferential insofar as she was abiding by all the submissive forms, and she was eagerly obedient to whatever I might demand of her, but she wasn't remotely intimidated or fearful. It was as if I had just introduced her to a whole new world, but one where she felt immediately at home. Interesting!

"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 might balk at this potentially risky suggestion, that she might still have an unrevealed trust issue, but instead, she sat up and happily posed for me. I snapped a few pictures of her cunt-cum-covered face, her make-up totally ruined.

Setting the camera down, I came over to the bed and mentioned, "It's 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 answered, "Yes, yes I am!"

"Then tomorrow I am taking you out for a makeover," I smiled.

"Where?" she asked.

I just shrugged and said, "You'll see, but wear the same outfit you wore today when you went shopping."

"Yes Mistress, "she said, standing up.

She got dressed, we kissed one last time and she went home.

My head spinning with naughty possibilities, I smiled to myself. Tomorrow was going to be fun...

THE END... of Chapter 1.... Jenny's journey to lesbian submission continues in Bedding the Babysitter Chapter 2.