Bedding the Babysitter Ch. 09

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Summary: Ashley and Jenny deal with the complexities of love and lust.

A summary of the first eight parts:

Part 1: 18-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 school crush (cheerleader Karen) and ends up at the lesbian club (La Château) where she accepts unconditionally that she is a submissive lesbian.

Part 3: Jenny, now a sub to cheerleading captain Karen, ends up becoming popular, sets new fashions with her thigh high stockings fetish, starts seducing a female teacher and ends up as the pet for a group of cheerleaders at a retreat.

Part 4: Jenny attempts to complete her seduction of her pretty teacher.

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

Part 6: Jenny goes on her first lesbian date with Ashley, another cheerleader…who unlike Karen, is not a Domme.

Part 7: Jenny flashes backs to the first night with Governor Greene; Karen puts Jenny in compromising positions; Ashley protects Jenny at all costs. The chapter ends in a strange triangle between Ashley, Karen and Jenny.

Part 8: Jenny and Ashley go to see Mistress Megan and clear up the confusion of the submissive hierarchy… although Jenny is surprised by Mistress Megan’s response. Jenny and Ashley then go to a secret gala for Governor Greene where they serve as maids and later become participants in an all-out lesbian orgy.

Note 1: As always a great thanks to Tex Beethoven, Robert, and Wayne for editing this chapter.

Note 2: Of course, all participants are at least eighteen years old.

Note 3: Thanks to Paul for the plot suggestions for this chapter.


In the limo, Ashley asked, still looking bewildered, “Did all that really just happen?”

I laughed. “Pretty surreal.”

Ashley hugged the bag holding her new shoes as she nodded, “And I got new shoes.”

I laughed, “I’m not sure which made you happier: meeting Governor Greene, or meeting her shoe closet.”

“Is it bad that I can’t choose one over the other?” Ashley replied with her trademark cute smile.

“You’re a very bad feminist,” I teased.

“But you love the materialistic me anyway,” she smiled, leaning in and kissing me.

When we broke the kiss a minute later, I nodded, looking into her eyes, and responded seriously, “Yes Ashley, I do love you.”

Ashley looked back into my eyes and said, “I love you too, Jenny, but this relationship is getting pretty complex.”

I felt my stomach knot. Was Ashley going to break up with me already? “I know, and we have to try and clear up some of the complexities.”

Ashley agreed, “Yes we do, but I also understand that you have Mistresses and that you want to keep them.”

I nodded, thankful that she understood: as much as I already loved her, I knew I couldn’t break away from my submissive roles with Mistress Megan and Mistress Karen. As strange as it sounds, the two different roles of submissive sex and romantic sex created an equilibrium for me that I felt would crumble without both.

“So here was what I was thinking,” Ashley began.

I was worried. I didn’t think she was planning to break up with me anymore, but I also had no idea what her next words were going to be.

“When you have sex with any of your Mistresses, or when we have sex with anyone together it is just that… sex, fucking, kinky pussy eating orgies, etc. But when we’re alone it is making love.”

A chill went up my spine, a sigh came out of my mouth as I nodded, “First, I love when you talk like a nasty slut.”

“You do, do you my sexy, cunt munching, fist fucking lez?” she wickedly listed.

“You had me at ‘cunt munching’,” I smiled.

“And what was two, my twat tickler?” Ashley questioned, using a phrase I had never heard before.

“Well, you fist cumming slut,” I smiled back, “your idea is brilliant. We are lovers.”

“Passionate lovers,” Ashley nodded, as we leaned into each other simultaneously and kissed each other until the Greene limo dropped me off.

I smiled and said again, “I know this is crazy, but I love you Ashley.”

“I love you too, Jenny,” she replied.

I reluctantly got out of the limo, sad that the wild, but life changing, night was over.

The next morning, I woke up surprisingly refreshed from a night lacking of sleep as I recalled the crazy night, the wild sex, the wilder action, the spontaneous decision to enter the auction, being bought by Brittany Banes for one million dollars (which was unbelievably surreal), Ashley’s understanding and the sudden clarity of our very complex relationship.

I rolled over and checked Ümraniye Escort my phone. I had three messages.

The first was from Ashley about 15 minutes after I had gone to sleep:

From Ashley:




The second was from Karen:

I am again sorry for what happened yesterday.

Mistress Megan was right.

I behaved inappropriately.

Mistress Karen

PS: I will be picking you up for school tomorrow to talk.

The third was sent only five minutes ago from Megan:

Pet Jenny,

Could you please stop by before you go to school? I would like to talk with you briefly.

Mistress Megan

I quickly showered, still smelling of sex, got dressed, wearing my red pantyhose and pom pom outfit and headed straight over to Mistress Megan’s.

I knocked on Megan’s door while eating a muffin.

Megan called out with a loud moan, “Come in, Jenny.”

I opened the door and went into the lounge room to find Megan sitting in her regular chair but with a naked woman between her legs lapping away at Mistress Megan’s pussy perfection.

“Hang on,” Megan said with one hand up in the air, the other on the back of the woman’s head as she was about to come.

I watched Mistress Megan come, she somehow looked even more beautiful when she came, sexy and surprisingly vulnerable.

Once she was done coming, Megan let go of the back of the woman’s head and said, “You may go upstairs and shower now.”

“Yes, Mistress,” the woman said, standing up and walking right past me.

I vaguely recognized the woman, but couldn’t figure out from where… she was beautiful, definitely in her forties and looked like a professional woman… a lawyer or a CEO.

“I met her at the auction party last night and brought her home,” Megan shrugged.

“Of course, Mistress,” I smiled, now remembering her from last night’s party.

“Did you have fun last night?” Mistress Megan asked, her legs still open.

“It was wild,” I nodded.

“The Governor’s parties always are,” Mistress Megan nodded.

“I can’t believe Ashley and I were bought for a million dollars,” I said.

“Me either,” Mistress Megan agreed. “That got out of hand.”

“Tell me about it,” I nodded, before asking, knowing Karen would be over in ten or fifteen minutes, “What can I do for you, Mistress?”

Mistress closed her legs and said, “I wanted to talk to you one on one about Karen.”

“Okay,” I nodded, having thought that was cleared up yesterday.

“You’re a very smart girl and I want to know why you think Karen did what she did yesterday,” Megan told me.

“Honestly, I think she did what she did because she was upset and angry and was trying wrongly to get back what she thought she had lost,” I answered, after thinking about it for a moment. I added, “She’s used to being in control, being on top.”

Mistress Megan looked at me inquiringly, “Really? Oh… and what did she lose?”

“Well, she is head cheerleader and used to being in a position of power, power that was increased when she got me as a submissive. Things were going well and then unexpectedly her power was usurped,” I explained.

“How so?” Mistress Megan asked.

“Sunday night she tried to get hold of me but I was on my date, then yesterday Ashley and I told her we wanted to be girlfriends, so maybe she thought she was going to lose me. I then got that call from Governor Greene that I had to keep secret, then Ashley confronted her about Sabrina and then the whole Miss Morgan thing got ugly,” I said.

“Oh,” Mistress Megan nodded.

“Put on top of that her first turn, my mother, was taken away by you as well and suddenly all her power was appropriated,” I finished.

“Appropriated,” Megan repeated with a laugh. “An SAT word.”

“No,” I shrugged, “I’m just a geek.”

I then added, “And she obviously doesn’t know about me and Ashley getting auctioned to Brittany Barnes yet either, and that I will have to go to LA for a few days.”

“Okay, hmmm, don’t worry about that, I’ll have a talk with her about my actions,” Mistress Megan said.

“Okay,” I said.

“Now get going, I need to think by myself,” Mistress Megan said.

I nodded, “Um, okay.”

Mistress Megan smiled, as she stood up, “Even a seasoned Mistress like myself can make mistakes.”

I left and had just gotten to my house when I heard a car honk from the curb. It was Karen.

“Hi Jenny! You ready?” Karen called out.

“Sure Mistress,” I said, quickly going into my house to grab my school bag.

As we drove, Karen asked, “So are we okay?”

I quickly tried to quell her concerns with my answer. “Yes, Mistress. And I’m sorry too. This entire Mistress thing, cheerleader thing, dating thing has been overwhelming and confusing.”

“I Ümraniye Escort Bayan guess it is a lot for someone who was a bit of a wallflower two weeks ago,” she laughed.

“I was a lot of a wallflower,” I corrected.

“Well, now you’re a popular cheerleader and known by the entire school,” Karen pointed out.

“That’s a reality I’m still trying to get used to,” I said, finding it just as surreal to be popular as it was that I was bought by Brittany Bane.

“Well, my bitch,” Karen said, squeezing my leg. “Get used to it. You’re living the good life now.”

I laughed, “They should make a Disney movie about me.”

“A pornographic Disney movie about you,” Karen joked.

“Mickey Mouse wouldn’t approve,” I joked back, as we got to school.

Once in school, Karen said, “I need to go and apologize to Miss Morgan.”

“You’re full of repentance today,” I smiled.

“You have some repentance to do yet today too, my pet,” Karen reminded me.

“Of course, Mistress,” I nodded, actually looking forward to whatever punishment she had in store for me.

“God, you’re cute when you’re submissive,” Karen said, before we entered Miss Morgan’s classroom. Karen asked, “Miss Morgan, may we talk?”

“Oh God, what do you want now?” Miss Morgan asked, clearly not happy to see us, or at the very least, Karen.

Karen closed the door and pleaded, as she held up her hands, “Please, Miss Morgan. I’ve come to apologize for yesterday. I was totally out of line to make Jenny here do what she did to you. It was wrong and I’m sorry, really, really sorry.”

“Oh,” Miss Morgan said, clearly surprised.

Karen continued, “So I have also come to promise you that I will never tell anybody about you and Jenny. Your job is safe. Also, please don’t let yesterday ruin what a great sexual adventure you and Jenny can have together in the future. I hope that you and Jenny can continue what you started. You deserve it, Miss Morgan.”

Miss Morgan looked stunned. “I don’t know what to say.”

“Don’t say anything. Think about what you want. What you really, really want. If you want Jenny, like she told me you wanted her Sunday, please do that. Don’t stop unless you really want to, and maybe if you can forgive me and I can prove my trustworthiness, you will willingly submit to me. But, if that doesn’t happen that is fine as well. Just don’t close yourself off to what you’ve just awoken, please,” Karen continued, suddenly sounding much wiser than her age… sounding like a real Mistress… like Mistress Megan.

Miss Morgan looked at me as she said, “I don’t know.”

Karen continued, “I will never again do anything in your class to make you feel unsafe. You have my word.”

Karen surprised me again as she then turned and walked out, leaving Miss Morgan and me alone.

“I think she means it, Miss Morgan,” I said.

“Thank God,” she said. “I really was stressed out about what she may do today and, of course, that I was going to lose my job.”

“Well, our Mistress had a talk with her and she seems to have seen the light,” I said, just as the bell rang.

“We will talk more later, Jenny,” Miss Morgan promised.

“I understand,” I nodded, and headed out.

At break, I saw Troy and knew I had to cancel our date for the Valentine’s Day dance. If I was going, which I wasn’t sure I was, I had to go with my girlfriend… I had to go with Ashley.

I went to him and said, “Troy, can I talk to you for a moment?”

“Sure,” he nodded.

“Alone,” I said.

“Oh, okay,” he agreed, his smile fading, as if sensing my tone meant bad news.

“Um, there is no easy way to say this but, I can’t go to the Valentine’s Day dance with you,” I blurted out before I could change my mind. Almost every girl in the school would die to go with him and here I was breaking up with him before we even had a chance to date. And although I was still a bit confused by the complex relationships I was currently entangled in, I knew I was a lesbian and sure didn’t need to make my complicated life any more complex.

The look of shock on his face made me feel even worse. He asked concerned, “What? Why? Did I do something wrong?”

His concern only made me feel worse. I answered, “Oh no, no no, not at all. You’re great. It’s me. I just started seeing someone and I need to take them instead. I’m so sorry.”

He still looked shocked as he said, “Oh, um, okay, that sucks. I was looking forward to it.”

I apologized again, before I went to look for Ashley.

Suddenly, she was right in front of me.

“Hi,” I asked, suddenly feeling strange as if everyone was watching us, even though I knew that was ridiculous.

“Hi,” Ashley said back.

“So, I cancelled my date with Troy for Friday,” I said.

“Now you’re dateless?” Ashley said with mock concern. “That is terrible.”

“I know,” I replied, playing along. “And I sure can’t go to the dance alone.”

“Yes, that would kill your sudden popularity,” Ashley teased.

“And Escort Ümraniye I can’t have that,” I said. After a pause, I asked, “So, what are you doing this Friday night?”

“Going to the Valentine’s Dance with a beautiful girl,” Ashley answered with a smile.

“Do I know this girl?” I asked, playfully.

Ashley laughed, “So are we going as friends or as a couple?”

“I think that would be the perfect time to announce it,” I said.

“Agreed,” Ashley nodded, before adding, “I so want to kiss you right now.”

“And I so want to bury my face in your pussy,” I replied, loving to talk dirty with Ashley.

“You haven’t had lunch yet?” Ashley teased.

“Actually, I’m starving,” I said, already thinking we should go to the cheerleader’s room for some alone time.

Suddenly Karen called out, “Ladies, over here.”

“Rain check?” Ashley asked.

“An infinity of rain checks,” I smiled.

We headed to Karen who said firmly, “Cheerleader’s room now.”

Ashley and I both nodded and followed Karen to the private room.

Once inside, we saw that Sabrina was there too.

Karen said, “Now I think I have a solution to our complex situation.”

“What is it?” Ashley asked, taking control just like she had yesterday.

“Well, I need to be a better Mistress and Jenny needs to be a better pet,” Karen began. “Of course, this also involves the two of you.”

Sabrina was surprisingly quiet.

Ashley asked, not angry, but curious, “And what is your plan?”

“Things go back to the way they were,” Karen said. “Although with less of a dominant hierarchy… but a hierarchy none-the-less.”

“Jenny and I are a couple,” Ashley stressed.

“And I’m fine with that,” Karen said. “I even think it’s pretty awesome. But, as Mistress Megan said, there needs to be respect and structure. So it’s important for each of us to know our place.”

“Which is?” Ashley asked.

“You two are a couple, but Jenny is also my pet when I need her,” Karen said.

“But not when she is already with me,” Ashley clarified.

“As long as you don’t hog her,” Karen said jokingly.

“At school, you are in charge,” Ashley said.

“And outside of school, everyone makes their own decisions,” Karen agreed.

“What about me?” Sabrina asked.

“You’re still second in command,” Karen said.

“Third,” Ashley corrected, as she walked over to Sabrina and pointed to the floor.

Karen and I watched as the power play for second in command was played live. Sabrina looked at Karen, but I think she was as curious as I was.

Sabrina went to speak, but then lowered herself to her knees in front of Ashley. Ashley smiled, lifted up her skirt and ordered, “Get licking.”

Sabrina looked at Karen one more time, as if pleading for help or permission, before turning and burying her face in Ashley’s cunt.

Karen sat down on the bench and said, “Jenny, you still have to do your task from yesterday and please Sabrina.”

I glanced at Ashley, who yesterday had erupted in this very room over this issue. When she didn’t say anything, I replied, “Yes, Mistress.” I then smiled and added, “although she looks rather busy at the moment.”

Karen laughed, as she spread her legs, “That she is. Then I guess you’d better please your Mistress.”

I lowered myself to my knees and eagerly buried my face in her already wet pussy. And there it was… everything somehow making sense.

I was eating Karen’s pussy while my girlfriend watched and she was pleasured by another girl.

She wasn’t jealous.

I wasn’t jealous.

This was just sex.

What we had was so much more.

Ashley moaned, “Eat my cunt, you submissive slut.”

Karen laughed, “I like the new Ashley.”

“I do too,” I added, between licks.

“Focus on my cunt, slut,” Karen ordered, grabbing the back of my head and shoving it deep into her pussy.

I did focus on her cunt and got her off in a few minutes, as Sabrina did to Ashley.

Once done, Karen said, “You still owe Sabrina an orgasm.”

“Yes, Mistress,” I nodded, crawling over to Sabrina, pushing her onto her back on the floor and burying my face in her cunt too.

“At least I’m not the bottom bitch,” Sabrina moaned, seeming happy to have at least someone below her.

I quipped, between licks, “Not to worry, I love being the bottom bitch.”

I got her off in a couple of minutes, just as the bell rang.

I said, “I’m always here to serve, Sabrina.”

Ashley said, “As is Sabrina,” as she pulled me up and kissed me.

The rest of the school day was fine and as we headed back to Ashley’s she surprised me again. “I need to tell my parents the truth.”

“What truth?” I asked, actually not having a clue.

“That I prefer cunt to cock,” she smiled.

“I wouldn’t start with that statement,” I suggested with a playful smile.

“Yeah, I probably should break it to them a little gentler.”

“Good call,” I agreed.

At her house, we let go of each other’s hands as we entered.

Ashley surprised me when she said, “No time like the present.”

My eyes went wide. “You’re not doing it now?” I asked.

Ashley’s answer was a quick kiss on my lips as she called out, “Mom, are you home?”

“In the kitchen, Sweetheart,” her mother called back.

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