Bedding the Babysitter Ch. 06

Summary: Cheerleader Jenny goes on her first lesbian date.

A summary of the first five parts (although if you haven't read them, I highly suggest you do...especially Part 3 for this one)

Part 1: Eighteen-year-old Jenny is a shy, curious babysitter who is pulled into the lesbian lifestyle by her pretty, seductive neighbor and employer, Megan.

Part 2: Jenny is taken out for a makeover where she meets her high school crush (cheerleader Karen) and ends up at a lesbian club (Le Château Club) where she accepts unconditionally that she's a submissive lesbian.

Part 3: Jenny, now also a sub to cheerleading captain Karen, ends up becoming popular at school, sets new fashions, starts seducing a female teacher and serves as the pet for a group of cheerleaders at a retreat where she becomes attracted to cheerleader Ashley.

Part 4: Jenny completes her seduction of her pretty teacher.

Part 5: Returning home, Jenny walks in on her Mom in flagrante having submitted to Karen. Shocked, Jenny hears how her mother became a sub just like her.

Note 1: As always, a great thanks to Estragon for his copy-editing of my work. His countless hours editing my and other writers' work is critical to the quality of the work available on this website. Another thanks to LaRascasse for his thoughtful suggestions. A new edit in May 2018 was made to update the story.

Note 2: A special thanks for the patience of my readers as this series has been a labour of love for me. And although I spend a lot of time on all my stories, this series is one that's particularly close to my heart and thus I don't release a chapter until I'm completely satisfied with it. Thus the story you are about to read is draft seven and substantially different from draft one. So I'm again sorry for the lengthy delays between chapters and I hope you enjoy.

BEDDING THE BABYSITTER CH 6

Hi, this is Jenny. Once Karen and I reached my bedroom, I tried to erase the shocking scene I had just witnessed from my mind. I simply couldn't believe my Mother had sexually submitted to one of my friends, even though Karen had... not just warned me but bragged to me... over and over again she was going to do it.

Karen, pretty much naked, was still bragging, "I told you I could get her to submit."

"So you did," I gave her, unsure how I was possibly going to deal with talking to my Mom (or even facing my Mom) now that each of our naughty secrets had been exploded in each others' faces in such embarrassing ways. I was mortified by how abruptly my Mother had been informed of my sexual identity and my emotions were numb from hearing her own story of submitting to Karen. And now I hadn't had any time to process all this information before I had to get ready for my first date ever! I pictured myself arriving for my date with this wonderful girl I had such high hopes for a delightful relationship with and greeting her hollowly with, "I need to tell you what just happened to my Mom," as I looked like death warmed over. I'd need to pull it together and do far better than that!

"She was even easier than I thought she'd be," Karen gloated with a smile.

Trying to change the subject, not wanting to talk about my Mother's sex life especially the humiliation part, I reminded her, "I finished my seduction of Miss Morgan."

"I can't fucking believe it," Karen responded, happy for me, happy I'd done what she'd ordered and clearly surprised by my success even though all last week she'd been the voice of rah rah encouragement. "Do tell."

I retold the whole afternoon-long saga from the initial rejection ordeal, to the hands of fate bringing us back together, to the inevitable climax (actually several wonderful climaxes for each of us) when I went back to her place.

"Wow," Karen said, impressed, "now you're both the hunter and the prey!"

I shrugged.

"The question is, which of those roles will you be playing tonight?" Karen questioned.

I reflected on the question. It was a good one. In every other sexual encounter it had been crystal clear I was the submissive, other than my seduction of Miss Morgan, I suppose. But with Ashley it was different. "I don't know."

Karen's phone rang and it was her Mom. "I'm at Jenny's. What? I was? Fine, I'm on my way." Karen hung up. "I was supposed to babysit my little brother, like ten minutes ago. I have to go. I guess I'd better go and untie your Mom."

"Good call," I agreed with her understatement, shaking my head at the absurdity of my brand-new universe.

She left and I, in a tizzy over what to wear, how to act, and scared even to look at my Mom, decided to go to Megan, the capable Mistress (but also trusted mentor) who had started it all, and ask her for advice.

I knocked on her door and was so thankful when she answered. Her genuine smile told me she was happy to see me too, just not desperate. "Well hi, Jenny. Max is going to freak out!"

A second later that prediction came true as Megan's two-year-old son Max attacked my legs screaming, "Wenny!" It took fifteen minutes of playing before he calmed down a bit and I promised, "I'll come back and play if I can, but I need to talk to your Mommy, ok?"

"Ok, Wenny," he agreed, watching some kid TV show I no longer was cool enough to recognize.

"Kay, Wenny," he agreed, plopping down to watch some kid TV show I was no longer cool enough to recognize.

Megan had poured iced tea for us and thanked me, "Thanks for doing that for Max, you're so good with him! But it looks like now I need to try to do some good for you: what's bothering you, dear?"

"How do you know something is bothering me?" I asked.

"Am I wrong?" she asked, her hand falling to my knee.

I sighed, "No, my dear perceptive Mistress, you're not wrong at all." I unloaded all the sordid details of my recent life, the good and the bad and the preposterous and my fear of how to deal with my Mom after what I'd witnessed and what she'd learned about me and... and... my wonderful but terrifying upcoming date.

Megan listened without interruption before responding. "Well, that's a lot for any eighteen-year-old to deal with. But my strongest concern is about Amy."

"My Mom? Why?" I asked.

"Well, sure your Mom just had it confirmed you're a lesbian, but foremost in her own mind must be that she was just now totally humiliated in front of her only daughter, who said nothing supportive to her at the time except you didn't want to be her Mistress. I'm sure that came as good news to her, but in her fragile state could also be seen as a rejection. Then you walked out of the room without a word or even a glance... yes? Right. So to her that was even worse, and then once Karen finally untied her she would have found you'd left the house without even talking to her. I can easily understand why you felt compelled to do that, but to her it could only have looked like further rejection: you must have left because you were disgusted with her! I can only imagine how emotionally unstrung and abandoned she must feel right now," Megan pointed out.

"Darn, you're right! I am such a bad daughter!" I sighed, tears beginning to form.

"No, what you are is an amazing young lady who is finally coming to grips with who she is sexually. But you're lucky enough that you found out what you are when you were eighteen; Amy is just learning right now. You followed your natural instincts when crisis or upheaval comes unexpectedly... fight or flight, and you chose flight."

"But I really need to go to her," I acknowledged. "She needs me."

"Yes you do and yes she does. But a word: first and foremost, remember she'll be very fragile right now. Although she's the adult, right now it needs to be your turn to be there for her. If she wants to talk about what she did, just let her do that and love her. Talk to her. Listen to her. If she wants to talk about you, then open up to her, tell her as much as she wants to know and trust her. Let her feel less like an unforgiveable slut and more like a nurturing mother by helping you with your life and your date, " Megan instructed me, her maternal side flowing out of her... showing no sign of the sexy seductress she also was.

"Ok," I agreed, standing up, although still scared of the conversation I was about to face.

"Jenny, I am always here for you. I am your friend first and your Mistress second, although I wouldn't mind seeing you again soon for the latter," she smiled, implying she was already missing the intimacy we had shared only last Tuesday.

"I would like that, Mistress," I agreed and Megan wrapped her arms around me for a warm embrace of security.

"Thanks, I can do this...I hope," I said, when our long embrace ended.

"You're welcome, Jenny, and yes you can do this. I will always be here for you."

I left and returned next door to my house and my Mom. I paused at my front door, still with no idea of what to say. Taking a deep breath nevertheless, I opened the door to face a conversation I never in a million years thought I would have.

Mom was vacuuming, which shouldn't have been a surprise. When she is stressed, she cleans, even if the house is already spotless, which it already was since yesterday was her usual cleaning day. I don't think she even heard me come in until I said timidly, "Hi, Mom."

She turned around and the terror in her eyes broke my heart. I had recently been petrified to tell my Mom about my recently discovered true sexual identity, and now it was my Mom who had to woman up to a similar daunting conversation with me. Her first words were, not surprisingly, a tearful apology. "Jenny, I am so, so, sorry you had to witness what you did!"

I replied, rushing towards her, "I'm sorry too, Mom! I'm the one who unleashed Karen on you. This is all my fault!" Not surprisingly, there were tears flooding down my face, too.

"Oh honey, you aren't the one to blame for my weakness and my loneliness," she replied, tears already beginning to drip off the bottom of her face.

Smiling through my tears and only able to see her as a blur, I officially came out to my Mother. "Well Mom, in case you had any lingering doubts. I like girls too."

"Only girls?" Mom asked, clearly digging deeper without obviously digging deeper.

"Yes, only girls. I've accepted that I'm a lesbian, have been one for over a week now, but I was too scared to tell you," I admitted.

"Why? Not the lesbian part, of course that's okay with me, but the scared part."

"I just thought you were already a single Mother having to raise a problem child on your own, so the last thing you needed was to learn your innocent daughter was a lesbian."

"Honey, I love everything about you. You know that, right?" Mom asked, her tone both heartfelt and concerned.

"Oh Mom, I know you do! I know you love me and it was a silly insecurity, but I only learned who I am very recently, and all I really know so far is that I don't know anything at all," I explained.

"I understand, dear," she said, before adding with a sad smile, attempting to lighten the heavy mood, "I too have only recently learned something basic about myself and I don't know anything either."

"Touché," I quipped back, before adding, "It's ok, Mom. If you need your daughter's permission to do anything at all, I'll make official. You are hereby allowed to have sex with men or women or anyone you want." I waved my right arm around vaguely in some sort of blessing.

"With my daughter's friend?" Mom asked, mortified by her recent actions.

"Well, that's not the most orthodox choice, but you really had no choice. Karen is utterly irresistible, and you can take that from me," I comforted her with the truth.

"And to be treated like a, like a, like a...." Mom couldn't even finish the sentence.

"It's ok, Mom. I'm a sub, too. If anyone can understand your doing that, I can."

"But I'm your Mother!" she exclaimed, still trying to cover herself with guilt for her unmotherly actions.

"I know. But I'm an adult," I pointed out.

"I do my best to forget that." Mom smiled. "It's tough seeing you grow up and not need me anymore."

"Oh Mom," I said, giving her a close hug, "I'll always need you."

After a silence, Mom asked, "Well, now what?"

"Well, first of all, no more secrets for either of us," I suggested. "Please?"

"Agreed," Mom concurred.

"Can I suggest something?"

"Sure, honey."

"You should go talk to Megan," I suggested.

"Ms. Cameron?"

"Yes, my first Mistress, my real Mistress," I said and took a while to tell Mom everything that had transpired the past week and a half.

Once I had finished, Mom was silent before she finally said, "I don't even know what to say, sweetheart."

"You don't have to say anything, Mom, you just have to support me. I just need to know you're on my side."

"Of course, honey," she softly replied, "it's just this has been a lot to digest in one day. Both my own predicament as well as learning my daughter is gay."

"I know, Mom," I replied. Looking at the clock, I freaked out. "Shoot, I'm supposed to meet Ashley in twenty minutes and I haven't even started getting ready!"

"Well, what can I do?"

"Drive me?" I asked.

"Of course, honey," she chuckled.

"Huh? What could be ha ha funny about any of this?"

"When the day started if someone would have told me I'd be driving my daughter on a date tonight that would have surprised me. That it was a date with another girl would have surprised me even more. Yet, after all that has happened today...why the heck not? How can anything be a problem now? Except... sweetheart, do you really forgive me? You don't hate me? You looked so cold..."

"I'm so sorry for that, Mom, you're right, I must have. I was just so shocked to see you like that and hear your story, and especially so ashamed for my part for doing that to you I just didn't know what to say! I didn't want to get blamed for it but I knew I deserved to! But I never stopped loving you, even if I couldn't show it, and I do love you, Mom! The question is, can you ever forgive me?"

By now both of us were in tears again and back in each other's arms. After a little while she pushed me away, but only far enough to look into my face with a tender smile. "Yes, my darling girl, I do forgive you for whatever unintentional part you played in all this. I hope by now you know I'm always here for you?"

I nodded and she continued, "Well now I know you're always here for me too! After all this, what could ever drive us apart?"

I nodded in agreement and smiled, "You're right, mother, nothing ever can."

But needing to dash, I eyebrowed her a question, she gave me a nod of permission and I gave her another quick hug and kiss on the cheek before I hurried up to my room and rifled through my closet, all my attention suddenly on my... what to call it... evening? Date?

I tried to find something to wear that didn't suck. What to wear on my date? If it even was a date. Was it a date? Or was it just two friends going to a movie?

Time being my enemy, I didn't have time right now to analyze what it was or wasn't and focused on what to wear. I decided to stick to the more provocative style I'd been wearing since my transformation. A short tight plaid skirt that hugged my ass, dark beige thigh high stockings and a white blouse. My hair wasn't perfect, but a quick brush and it would have to do.

I quickly texted Megan:

Mistress Megan,

I talked to Mom. I think we are cool if that is possible after today. Could you please check on her. She knows about you and me.

Pet Jenny

Megan texted back while I was in the car with my Mom:

Pet Jenny,

Oh my... she knows. How is she taking it?

Meg

I typed back:

Mistress Megan,

Fine...I think. I just think she needs an adult to talk to. An adult who understands all this stuff.

Pet Jenny

She responded:

Will do, sexy.

Meg

We drove in silence to the theatre while I texted. Once I put my phone away, Mom asked, "Who were you texting?"

"Mistress Megan," I admitted.

"Mistress," she repeated, still attempting to come to grips with what she had done, "I can't believe how many times I've heard or said that word today."

"Tell me about it!" I joked, before warning her, "I asked Mistress to check on you."

"You did?" she asked, instantly going red.

"Yes, she can help you sort out all your feelings like she did for me," I explained.

"But she's the one who seduced you," Mom pointed out. "She started all this."

"What she did was open the door to who I am," I corrected. After a brief pause I added, "Plus, although she is a Mistress and my Mistress, she is first and foremost a wise and compassionate woman. Promise me you will talk to her if she comes over or invites you over. Believe me, you'll thank me for it."

"Ok," she agreed reluctantly.

At the theatre, Mom smiled. "Call me if you need me to pick you up."

"Will do," I smiled and gave her a quick hug, like I'd always done. "I love you, Mom."

"Love you, too."

I watched her pull away and as my attention went from my Mom to seeing Ashley in a minute my anxiety grew. Considering all I had done the past little while, plus the fact that Ashley and I had already had sex, albeit under strange circumstances, I was incredibly nervous. I entered the theatre and saw she was already there. She too had on a short plaid skirt, hers with black stockings and a pink blouse. She looked so adorable, so sweet and yet so sexy. I could never get over how tall she was even though that was one of the things I liked about her. I felt a chill go up my spine just looking up at her. I could tell though, that just like me she was nervous.

I walked over to her and she handed me a ticket. "I got here early to make sure we got tickets," she said, handing it to me.

"Good call," I replied, before adding wittily, "great minds think alike."

"What? How?" she asked, confused.

"We could be fashion twins," I joked.

"I wanted to try to pull off what you've been doing lately," her words and even her tone flattering.

"Well, that you did," I confirmed, "you look adorable."

"As do you," she returned the compliment.

"Then it's settled. We both look adorable. You're a fashion horse and I'm a fashion pony."

"Agreed," she laughed, her smile so radiant. "We're two hotties."

"Damn right," I laughed. "Now let's go get some snacks."

I realized that conversation had been trivial, even trite start to finish, but it had broken the ice: neither one of us was nervous any more.

We waited in line and talked about cheerleading and the upcoming State competition in three weeks. Ashley flattered me, "I can't believe how quickly you learned all our routines."

"Well, Miss Hopkins scares me. She's a drill sergeant."

"True, but she has a heart of gold underneath that bulldog exterior," Ashley pointed out.

I wasn't so sure about that, but if Ashley said so I could wait and see. So I just complimented her back. "And you are the silent leader of the group."

"Not really," she said, uncomfortable with getting praise.

I grabbed her hand and squeezed it. "Seriously, this group would be lost without you. You're the loving mom of the squad."

Suddenly there was silence as on a daring whim I made the first move by grabbing her hand almost by accident and in case I had any doubts if this was potentially more than a date it became obvious by the nervous awkwardness of the moment. We were both really tense.