Bedding the Babysitter Ch. 03

I shook my head as I said, "No, I don't think so. She didn't look at me the whole time she was at her desk."

"True, because by then she knew I was watching her," Karen explained.

"How do you figure?" I asked curiously.

"She caught me smirking at her the couple of times she'd clearly checked you out earlier in the class. After that I was smirking because of all her struggles not to check you out. "

"Really?" I said, unbelieving.

"Really," she replied, "It's only a matter of time before you get lucky."

We arrived at my place and as soon as she parked, she shut the car off and took her keys out. I looked at her with a confused look. She smiled, flipped open her phone and pressed a button. Her free hand moved to my leg as she waited a few seconds before saying, "Hi, Mom. I'm going to stay for supper at Jenny's house." A brief pause ensued before she said, "That's right, the new PomPom. I'm going to stay here tonight and help her work on the dance routines." After another brief quiet period Karen finished, "I will, but I won't be home until ten, we have a lot to practice. Bye Mom, love you." She flipped her phone closed and said, "Well, no point driving home if we're going to see Mistress Megan tonight."

"I suppose," I responded nervously.

"What's the matter?" Karen queried. "Afraid I'm going to dominate you right in front of your mother?"

I blushed. "Not until now," I said with a concerned look on my face.

She smiled with a soft laugh, "I'm kidding. We really will work on your dance routines, until seven at least." She then opened her door and got out. She went into her trunk and grabbed a package of stockings before following me into my house.

Mom wasn't home so we went upstairs to my room. The first thing Karen did was order, "Take my stockings off, my slave."

I was slightly surprised by this; two days of friendship and no real sexual demands had relaxed me a bit. So I went to Karen, who was sitting on the edge of my bed, and deciding to be a tease, I took off her heels, and then slid my hands all the way up her left leg, slowly, ever so slowly, as Karen uttered a soft moan. I reached the top of her beige thigh high stocking and began to slide it down her leg. But I went gently, with tender care, slowly sliding the stocking off. What could have easily been done in a second took me thirty. When I looked up, Karen had her eyes closed and a pleasant smile. I moved to her right leg and massaged her foot while it was still encased in its stocking. She moaned again, and I surprised her by taking her silk-stocking-covered foot in my mouth. I sucked each toe into my mouth, savouring the salty sweat of her foot. I then slid my tongue up the side of her calf and continued up the back of her leg. My tongue never lost contact with her leg as it slid upwards until I reached the elastic top of the thigh high.

Karen spoke for the first time in several minutes saying, "Fuck, Jenny, you have me soaking wet."

"Sorry," I said coyly and with total insincerity.

Karen looked at the clock, it was 5:15. "Fuck, it's at least a couple more hours until I can cum," she said, sexually frustrated, as was I. But my own fault, since I'd been the one doing the teasing!

I slid off the second stocking with as much deliberation and care as I had the first. I then grabbed the stocking package and opened it. I took one red thigh high stocking and slowly draped it onto my beautiful mistress. As the top of the stocking reached its destination near the top of her leg, I then moved my head to her white panty-covered pussy. I stopped just millimetres from her pussy, her sexual aroma escaping through the sheer underwear. I moved my mouth onto her panties for just a second before moving away to reach for the second stocking.

"You are such a tease, you heartless slut," Karen accused, her breathing a bit heavy.

I smiled but remained silent as I slid a red thigh high up her other leg. I finished and was just moving in for another tease when we heard the front door close downstairs. Startled, I jumped up with lightning speed. Karen just sat there smiling vaguely before eventually standing up. "Think I could seduce your mother?" she asked casually.

"What?" I asked incredibly surprised.

"You heard me," she said and then repeated, "Do you think I can get your mother between my legs?"

"No way," I said confidently.

"Want to bet?"

"No," I said; that would only encourage her to try.

Mom knocked on my door, she always respected my privacy, and I called, "Come in, Mom."

Mom entered, dressed in her usual business suit, jacket and all, and greeted, "Hi girls. Good to see you again, um..."

"Karen," Karen said, and walked over to my Mom and gave her a kiss on the cheek before hugging her. My Mom blushed but hugged her back awkwardly. Karen broke the hug and said, "I hope you don't mind Mrs. Wyatt, but I invited myself for supper so your daughter and I can work on our dance routines before we go to an extra practice at seven."

"No, not at all," my mother said and then added, "but I was only going to order pizza, if that's ok with you ladies."

Karen answered, the double entendre dripping between each word, "That sounds delicious."

Mom missed the flirtatious tone and asked, "What kind do you like, Karen?"

"Oh, I like all kinds," Karen said, still trying to flirt, but somewhat missing the mark.

"OK," my Mom said and added, "I'll get a Hawaiian and a double pepperoni."

"Sounds great," I said, trying to break the awkwardness of the situation.

My Mom left, and as soon as the door closed, Karen appraised, "She'll be easy to seduce."

"How do you figure?" I asked, not seeing it at all.

"Trust me, it will be easy," Karen said confidently. "Let's go practise in the living room."

"Why?" I asked.

"We need more space and I want to make sure your mom gets lots of chances to watch," Karen said.

"She isn't, she won't," I tried to articulate.

Karen smiled and said, "What? She isn't a dyke like her daughter? When was the last time she had a man in here?"

I contemplated this and admitted, "Not since Dad died."

Karen instantly changed her tone from aggressive to caring as she said, "Sorry, I didn't..."

"No, it's ok," I said, "It was five years ago. A car accident. We're fine now."

"Oh, sorry," Karen said, giving me a gentle friendly hug. She held me for what seemed like an eternity. I felt so safe and comfortable within her arms my heart began beating faster. Finally she let go and said, "I'm still going to try and seduce your Mom."

I don't know why, but I kinda gave her permission, though she didn't need it, "OK."

"I'm going to have her between my legs very soon," she said confidently.

I doubted she was right, but a part of me, the perverted me that I hadn't ever even met until last weekend, was curious. Besides, after everything that had begun happening last weekend, I was now happier than I'd ever been in my life, so where's the harm? "Go for it," I egged her on.

Karen grinned, grabbed my hand and led me downstairs. We practised a couple dance routines, my mom in and out of the room, until the pizza arrived. We ate as Mom asked Karen a bunch of typical mother questions: What do you want to do when you graduate? Do you have a job? What do you do for fun? Etc., etc... When dinner was finished, I grabbed the dishes as Mom and Karen went into the living room to watch the news. My Mom always watches the news. I put the few dishes in the dishwasher, grabbed a glass of water and returned to the living room. I suppressed a gasp, barely, as Karen was giving my Mom a foot massage.

Karen smiled up at me, still massaging my Mom's stocking foot and said, "Mrs. Mom had a long day, so I asked if she needed a foot massage."

My Mom gave me a slightly awkward smile as she said, "And Karen was so nice to offer!"

I sat down on a chair and watched the news, sometimes taking a glimpse at the couch. Karen switched feet and kept massaging. Finally after fifteen minutes, the time now 6:45, Karen said, "Sorry to stop, Mrs. Wyatt, but we've got to get going."

My Mom responded as she stood up, "No problem. I have to go shower anyway." She paused as she stretched, her large breasts clearly visible through her white blouse since she'd removed the jacket right after getting home, "and please call me Amy."

Karen smiled, "Ok Amy, thanks for supper." She then kissed my Mom on the cheek again and gave her another hug, her hand resting half on my Mom's butt. I shook my head in awe as Karen looked me in the eye and winked. Karen lingered longer than normal hug etiquette allowed, before giving my mother one last kiss on the cheek.

Mom's cheeks were red as I gave her my own kiss on the cheek and said, "I'll be home by curfew, Mom."

"No problem," My Mom said, "Just give me a call if you're running late."

"OK," I said and Karen and I headed out.

As soon as the door was closed Karen asked me, "So... still think your Mom can't be seduced?"

I no longer was sure of anything, but minimised, "That was all harmless."

Karen shook her head in disagreement as she said, "You'll see. I'll have her eating out of my pussy in a week; two, tops."

"I doubt it," I said, although I no longer really did doubt it.

We got in the car and drove around the block so my mother would think we'd left the neighborhood as we'd said and parked around the corner. We then walked up to Mistress Megan's. We knocked on the door at 6:55, five minutes early, dressed in our identical cheerleading outfits.

We waited until Mistress Megan opened the door. She appeared wearing a black leather skirt, black stockings, black 'fuck me' boots and a red blouse. She smiled and said, "Welcome ladies, come on in."

We obediently and rather eagerly walked in and followed Megan into her living room. She poured us each a glass of wine and asked, "So how are things going, Jenny?" she asked.

"Good," I said.

"Care to expand?" she asked, taking a sip from her wine.

"Well, I've become more popular, that's for sure," I explained and added, "and I'm beginning to get more comfortable with my new look."

"I see," Megan said before asking, "And Karen, Jenny has been a good girl?"

"Very," Karen answered, "she's been a perfect little slave."

"Neither of you has had an orgasm, have you?"

"No," we both said in unison.

Megan gave us an odd look before asking, "Karen, you're not lying to me, are you?"

"No," she replied, avoiding eye contact.

Megan walked over to her and said, "I think you are, and I don't appreciate being lied to. I will only ask you one you more time. Did you have a forbidden orgasm?"

"Yes," Karen whispered, "I'm so sorry Mistress, but Jenny's submission to me had me so hot that I masturbated myself to sleep last night."

"I see," Megan said and then just gazed at Karen for a long time. Think hypnotic cobra. Think terrified, paralyzed rat. Finally she said, in a subdued, deadly tone I'd never heard her use before, "Don't you ever lie to me again."

"No, Mistress Megan," Karen said, thoroughly cowed.

Our Mistress then ordered us both, "Follow me." We did and I found myself in the bedroom where I'd lost my virginity just last Friday. A warmth in my body and especially my privates filled me as I reminisced about what had happened in this room so recently. Had it really been less than a week ago? It seemed so long ago, like a distant memory, yet it was indeed only four nights ago.

Megan left the room briefly and then returned carrying a kitchen chair. She set it down, looked balefully at Karen and said with authority, "Sit."

Karen obeyed and Mistress Megan grabbed her arms and tied them together behind the chair. She then tied each leg to the chair. She then explained, "Karen, your punishment is to watch while I give our slave great pleasure, pleasure you would have experienced yourself if you hadn't disobeyed me; pleasure that is beyond what you can yet imagine, but you will see." Megan then grabbed a vibrator, turned it on low and wedged it under Karen's bum. She then ordered sternly, "Don't you dare cum."

"No, Mistress Megan," Karen replied fearfully.

Mistress Megan slid off her skirt and grabbed a strap-on. "Jenny..." she said sincerely, her sweet tender voice back, "...you are so beautiful."

"Thank you," I responded, flattered.

"Have you ever sucked a cock?"

"No, Mistress," I said.

Megan looked back at Karen and asked, "Have you?"

"Yes, Mistress Megan."

Now wearing the strap-on, Megan walked up to her and ordered, "Show our Jenny how to suck a cock." She stood there, her black cock directly in Karen's face. Karen opened her mouth and leaned forward to suck it. She rocked back and forth, taking in a couple of inches and then trying for more. This continued for a couple of minutes until Megan asked, "Jenny, do you think you can do that?"

"Yes, Mistress Megan," I said, eager to try.

She turned and walked over to where I was sitting on her bed so I, without instruction, dropped to my knees and took the cock in my hand. I kissed it before opening my mouth. I took the toy into my mouth and, like Karen, moved my head back and forth. With each stroke I attempted to take a little more in. I gagged a couple of times, but eventually got into a decent rhythm, sometimes even getting it into my throat.

Megan said, "Good girl," as she pulled me up and kissed me, the stiff cock poking my groin just above my damp vagina. The kiss was tender and passionate. Her tongue darting in and out of my mouth getting me more excited all the time until she finally asked, "Do you want me to fuck you?"

"Desperately," I responded.

She led me to the bed, assisted me out of my panties but still wearing my cheerleader's uniform. She then assisted me onto the bed and had me kneel on all fours, facing Karen. She knee-walked around behind me and said, "Watch closely, Karen. This could have been you getting fucked by your Mistress while your slave laid beneath you licking and sucking your clit. The double pleasure would have taken you to a level of pleasure that you've never experienced nor even imagined. Are you imagining that, Karen?"

"Yes, Mistress Megan, I am, and it's soooo frustrating!" Karen groaned.

"Good. Now keep watching."

I moaned as Mistress Megan's fake cock slid into my very ready pussy.

Megan placed her hands on my hips as she slowly started fucking me with the seven-inch cock. She asked, "Slave Jenny, how does it feel?"

"Soooo good, Mistress Megan," I moaned sincerely.

Megan began to move faster and I began to push back to meet her thrusts. "That's it my little lez, bounce back on my cock."

I eagerly obeyed, bouncing back harder and faster, taking all seven inches inside me. The pleasure felt so good and a couple days of going without orgasmic bliss had me near the brink in only a couple of minutes of fucking. I pleaded, "Mistress Megan, may I cum, I'm so close!"

Megan grabbed my hips, pulled me close and held me there, the cock going even deeper than I'd thought possible but not moving.

I whimpered ecstatically, the cock filling me so completely. She held me motionless for a long frustrating moment and then I felt a finger at my anal entrance. She whispered, "You may cum anytime you want, my pet, so long as you don't move."

I moaned, "Thank you, Mistress Megan," and held myself very still, which didn't help me cum but just increased my urgency as she slid a finger inside my anus. She kept pushing forward and soon she was finger-fucking my ass. The quick pace kept me excited and always near the brink of bliss, but never sending me over it. But suddenly just as my moaning was approaching a peak of urgency she backed off and gave me one brutal thrust with the cock, and I screamed in orgasmic surprise louder than I thought possible as I came instantly! My body trembled like I was having an epileptic seizure as the most intense orgasm I've ever experienced charged through my entire body! I kept repeating, "Yes-yes-yes-yes-yes," as the sexual explosion continued to pulse, engulfing me, drowning me!

Megan just held me tight, her finger still in my ass, the cock still buried to the hilt in my pussy, until my breathing slowed down and the last remnants of the orgasm had drained from my body. Finally she let go of me and I collapsed forward as her finger and the toy slid out of me.

She then surprised me again, flipping me over and kissing me hard. This time the kiss was heated and desperate like two lovers' last chance before the apocalypse. Her breasts and mine were squished together as we made out. Her tongue danced around inside my mouth, seeming to be searching for something as it explored every crevice. This hardcore kissing had chills rolling through my body like an electric current, and my pussy began to fire up again. She then broke the kiss and surprised me by burying her head between my legs. She did something to my clit I can't even explain as she sucked it into her mouth and rolled it around between her lips. A few seconds of this intense clitoral pleasure and I was writhing on the bed with a second intense orgasm quaking inside me. As my pussy juice flooded out of me, Mistress Megan kept my clit in her mouth, but also began pumping two fingers in and out of my pussy. This intense joy fulfilled me for minutes as my third, fourth and fifth orgasms exploded out of me in rapid machine guns, making me babble like a delirious person, which I'm not sure I wasn't! When I finally collapsed, perspiration dripping down my forehead, Megan raised herself from between my legs and looked down at me. Her face glistened, completely soaked with her slave's love cum.

She silently leaned down to my face one last time. There was a twinkle in her eyes and a sweet sexy smile on her face as her tongue entwined with mine, our lips barely touching. She teased me with her tongue and her lips until finally she pressed in and kissed me gently. This time our kissing was soft and gentle as if we had all night just to drown inside each other's mouths. When she finally broke away, I was disappointed that this eternity had ended.

Mistress Megan then stood up and unstrapped her cock before sliding off her panties and sitting on the edge of the bed. Megan stared directly at Karen, whom I had forgotten about completely, and spread her legs. I looked at the clock, it was 8:12, and I couldn't believe it. Over an hour had flown by already; it had felt like seconds. Megan began to rub her clit slowly and teasingly as she asked, "Did you find that hot, you disobedient slut?"

"Yes, Mistress Megan, so hot!" responded Karen, whose face was red and desperately horny from an hour of the toy buzzing underneath her while she witnessed my sexual bliss.

"Do you want to eat your Mistress' pussy?"

"Very badly, Mistress Megan," she answered.

"What will you do to make you worthy of such a treat?" Megan asked coyly.

"Anything," Karen said desperately.

"Anything?" Megan asked. "Such as...? Make me an offer."

Karen then offered, "I can offer you Jenny's Mom as a slave for you."

It was Megan's turn to be surprised as she doubted the possibility of that, "Excuse me?"

"I will seduce Mrs. Wyatt and bring her over to your house as a gift to you," Karen offered confidently.

Megan looked back at me and asked, "What do you think, Jenny? Is that even possible?"

I explained, "Karen keeps saying my Mom is a lez and she can seduce her. Mom really got into it while Karen was giving her a foot massage earlier. I'm not sure she can't do what she's saying."

Megan mulled this over for a while before she said, "An interesting proposal, Karen my little disobedient slut, a very interesting offer indeed."

Karen, getting some of her confidence back, added, "I will have that woman begging to eat me out within a week."