Sweet cheerleader Jenny goes on her first lesbian date.
BEDDING THE BABYSITTER CHAPTER 6
Summary: Cheerleader Jenny goes on her first lesbian date.
A summary of the first five parts (although if you have not read them, I highly suggest you do...especially part 3 for this one)
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 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, 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 submitted to Karen. Shocked, Jenny listens to 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 mine and other writers’ work is critical to the quality work available on this website. Another thanks to LaRascasse for his thoughtful suggestions.
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 the one closest to my heart and thus I don’t release a chapter until I am completely satisfied with it (Although I cringe when I read Chapter 1 and think about all the changes I would make now). Thus the story you are about to read is draft six and is substantially different from draft one. So I’m again sorry for the lengthy delay between chapters and I hope you enjoy.
BEDDING THE BABYSITTER CH 6
Once in my room, 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 hinted at it over and over again.
Karen, still pretty much naked, said smugly, "I told you I could get her to submit."
"So you did," I replied, unsure how I was possibly going to deal with talking to my Mom now that both of our naughty secrets had been spilt in such a revealing way. I was mortified by how my Mother had found out about my sexual identity and I was stunned by her own story of submission. I hadn't really had time to process all this information before I had to get ready for my first date ever.
"She was even easier than I thought she would be," Karen said with a smile.
Trying to change the subject, not wanting to talk about my Mother’s sex life, I reminded her, "I finished my seduction of Miss Morgan."
"I can’t fucking believe it," Karen responded, clearly surprised by my success. "Do tell."
I retold the whole ordeal from the initial rejection, to the hands of fate bringing us back together, to the inevitable climax when I went back to her place.
"Wow," Karen said, impressed, "you are both the hunter and the prey."
"The question is which of those are you tonight?" Karen questioned.
I reflected on the question. In every other sexual encounter it was clear that I was the submissive, other than my seduction of Miss Morgan, I suppose. But this 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 am on my way." Karen hung up. "Apparently I was supposed to babysit my little brother ten minutes ago. I have to go. I guess I better go and untie your Mom."
"Good call," I replied, shaking my head at the obvious absurdity of my Karen’s last sentence.
She left and I in a tizzy over what to wear, how to act, and scared to deal with my Mom, decided to go to Megan, the person who started it all, for advice.
I knocked on her door and was thankful when she answered. Her genuine smile told me she was happy to see me. "Well, hi Jenny. Max is going to freak out."
A second later that prediction came true when Megan's son Max attacked my legs screaming, "Wenny," It took fifteen minutes of playing before he calmed down and I promised, "I will come back and play in a bit, 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.
Megan had poured iced tea for us and asked, "What is bothering you, Jenny?"
“How do you know something is bothering me?” I asked.
“Am I wrong?” she asked, her hand falling on my knee.
I unloaded all the sordid details of my life, the good and the bad and the preposterous and my fear of how to deal with my Mom after what I witnessed and she learned about me and my upcoming date.
Megan listened without interruption before responding. "Well, that is a lot for any eighteen-year-old to deal with. But I am more concerned about Susan."
"My Mom? Why?" I asked.
"Well, sure your Mom found out you are a lesbian, but she was just humiliated in front of her only daughter, who has since left the house without talking to her. I can only imagine how emotionally unstrung she must feel right now," Megan pointed out.
"I am such a bad daughter." I sighed, tears beginning to form.
"No, you are an amazing young lady who is finally coming to grips with who she is sexually. But you are lucky you found out when you were eighteen; Susan is just learning now. You followed your natural instinct when crisis or upheaval comes unexpectedly....fight or flight, and you chose flight."
"I need to go," I acknowledged.
"Yes you do. But remember she is probably very fragile right now. Although she is the adult, right now it is your turn to be there for her. Talk to her. Listen to her. Let her help you with our date," Megan instructed me, her maternal side flowing out of her...no evidence of the sexy seductress she was.
"Ok," I agreed, standing up, although still scared for the conversation I had to have.
"Jenny, I am always here for you. I am a friend first, a Mistress second, although I wouldn't mind seeing you soon for the latter," she smiled, implying she missed the intimacy we shared.
"I would like that," I agreed and Megan wrapped her arms around me for a warm embrace of security.
"Thanks," I said, when the long embrace ended.
"You are welcome, Jenny. I will always be here for you."
I left and returned home. I paused at my front door, still unsure what to say. Taking a deep breath, I opened the door to have 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 was as yesterday was her usual cleaning day. I don't think she even heard me come in until I said, "Hi, Mom."
She turned round and the sheer fear in her eyes broke my heart. I was originally petrified to tell my Mom my true sexual identity and now it was Mom worried about having a similar conversation with me. Her first words were, not surprisingly, an apology. "Jenny, I am so, so, sorry you had to witness what you did."
I replied, moving towards her, "I am sorry too. I unleashed her on you. I am to blame."
"Oh honey, you are not to blame for my weakness and my loneliness," she replied, tears already beginning to stream down her face.
Smiling, I officially came out to my Mother. "Well Mom, in case you had any lingering doubts. I like girls."
"Yes, only girls. I have accepted that I am a lesbian, but was too scared to tell you," I admitted.
"I just thought you are already a single Mother trying to raise a child on your own, the last thing you needed was to learn I was a lesbian."
"Honey, I love everything about you. You know that, right?" Mom asked, her tone heartfelt, and concerned.
"Oh Mom, I know. It was a silly insecurity, but I have only explored my curiosity very recently," I explained.
"I understand," she said, before adding with a sad smile attempting to lighten the heavy mood, "I too have only recently explored my curiosity."
"Touché," I quipped back, before adding, "It is ok, Mom. You are allowed to have sex.”
"With my daughter's friend?" Mom asked, mortified by her actions.
"Well, it is not the most orthodox choice, but you really had no choice. Karen is utterly irresistible," I comforted her with saying the truth.
"And to be treated like a, like a, like a...." Mom couldn't even finish the sentence.
"It's ok, Mom. I am a sub too."
"But I am your Mother!" she exclaimed, trying to cover herself with even guilt for her actions.
"I know. But I am an adult too," I pointed out.
"I try to forget that." Mom smiled. "It's tough seeing you grow up and not need me anymore."
"Oh Mom," I said, giving her a hug, "I will always need you."
After a silence, Mom asked, "Well, now what?"
"Well, no more secrets," I suggested.
"Agreed," Mom concurred.
"Can I suggest something?"
"You should go talk to Megan," I suggested.
"Yes, my real Mistress," I said and told Mom everything that had transpired the past few weeks.
Once I had finished, Mom was silent before she finally said, "I don't even know what to say."
"You don't have to say anything, Mom, you just have to support me."
"Of course, honey," she softly replied, "it's just this has been a lot to digest in one day. Both my predicament as well as learning my daughter is gay."
"I know, Mom," I replied. Looking at the clock, I freaked out. "Shoot, I am suppose 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.
"When the day started if someone would have told me I would be driving my daughter on a date 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...."
"I know Mom." I smiled."I know." I gave her a quick hug and kiss on the cheek, before I hurried to my room and rifled through my closet. What to wear on my date? If it was a date? Was it a date? Or was it two friends going to a movie? Time being my enemy, I didn’t have time to analyze what it was or wasn’t and focused on what to wear. I decided to stick to my more provocative style I had worn since my transformation. A long plaid skirt, thigh high stockings and a white blouse. My hair wasn't perfect, but it would have to do.
I quickly texted 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 I.
Megan texted back while I was in the car with my Mom:
Oh my... she knows. How is she taking it?
I typed back:
Fine...I think. I just think she needs an adult to talk to.
Will do, sexy.
We drove in silence to the theatre while I texted. Once I put my phone away, Mom asked, “Who 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 have heard or said that word today.”
“Tell me about it,” I joked, before warning “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 seduced you,” Mom pointed out.
“She opened the door to who I am,” I corrected. After a brief pause, I added, “Plus, although she is a Mistress, she is above all a compassionate woman. Promise me you will talk to her if she comes over or invites you over.”
“Ok,” she reluctantly agreed.
At the theatre, Mom smiled. "Call me if you need me to pick you up."
"Will do," I smiled and have her a quick hug, like I had always done.
I watched her pull away and my anxiety instantly grew. Considering all I had done the past couple of weeks, and the fact that Ashley and I had already had sex, albeit under strange circumstances, I was incredibly nervous. I entered the theatre and saw Ashley already there. She too had on a plaid skirt, black stockings and a pink blouse. She looked so adorable, so sweet and yet so sexy. I felt a chill go up my spine just looking at her. I could tell though, that 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 me my ticket.
"Good call," I replied, before adding wittily, "two great minds think alike."
"What?" she asked, confused.
"We could be fashion twins," I joked.
"I wanted to try to pull off what you have been lately," her tone implying flattery.
"Well, that you did," I confirmed, "you look adorable."
"As do you," she returned the compliment.
"Well, it's settled. We both look adorable."
"Agreed," she laughed, her smile so radiant. "We are two hotties."
"Damn right," I laughed. "Now let's go get some snacks."
We waited in line and talked about cheerleading and the upcoming competition in three weeks. Ashley flattered me. "I can't believe how quickly you learned all our routines."
"Well, Ms Hopkins scares me. She is a drill sergeant."
"True, but she has a heart of gold underneath that intense exterior," Ashley pointed out.
I 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."
Suddenly there was silence as I carelessly made the first move 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. Before I had time to consider this, the cashier called next and I let go off her warm hand and smiled, "What would you like?"
The moment passed, we ordered a big tub of popcorn to share and a couple of drinks. Once in the theatre and seated, we both had time to consider our feelings. We each grabbed some popcorn and ate as a way to avoid the awkward conversation that we both were obviously insecure about. Suddenly my phone rang and it was a text from Karen.
Karen: Have u fucked her yet?
I went instantly red.
Ashley asked, "You ok?"
"Yes," I replied, putting my phone on vibrate.
"Are you really going to the prom with Troy?" Ashley asked.
I shrugged. "It happened so quick. One moment I am a shy, nerdy outcast, the next a popular cheerleader. I never really had a chance to catch my breath. We have not even talked other than at school."
"Do you want to?" she asked, her facial expression so insecure.
"I don't know. I have never had a boy interested in me, but now that I do I realized something,” I admitted, after a brief consideration.
“What is that?” Ashley asked, anticipating my every word.
“I am not really interested in boys. “I threw the hint out there, scared to declare my confirmed lesbian status, yet hinting at it in a way to say I was available to her. After a brief silence, I asked, "Are you going with anyone?"
"I was supposed to go with Dixon, but we broke up last night," she revealed, seemingly opening the door for me the same way I had for her.
"Oh," I replied, "how did that go over?"
She smiled, clearly not heartbroken by the ending of the relationship. "He told me I was a cock-tease, a bitch and that I would regret dumping him."
"You dumped him?"
This time her hand went to mine and she revealed, "I have fallen for someone else."
My face flushed again and I was briefly speechless. After a lingering silence where the silence spoke wonders, I asked, tentatively, even though every sign screamed yes, "Me?"
"Yes, you, Jenny," she admitted, playfully slapping my shoulder. "I always questioned my sexuality, and the fact that I never remotely wanted to have sex with Dixon only enhanced my doubt of my true sexuality. Dixon and I never had intercourse. I gave him head a few times, but that was it and I can't say that was even remotely appealing.” After a pause she added, "Other than the odd fooling around with the girls in hotels at cheerleading competitions, I am rather inexperienced."
"I was too, until very recently," I admitted, hoping to make her less insecure about her lack of experience.
"Jenny, I like you, I mean I like-like you," she admitted nervously, putting her heart on her sleeve, her cheeks ruby red.
I didn't hesitate when I repeated her words, "I like-like you too, Ashley."
Her eyes lit up, her cautious smile broke wide open and ignoring the quickly filling theatre, she leaned in and kissed me. The kiss was soft and tender; cautious and sweet. It only lasted a few seconds, five maybe, before we broke it realizing the setting for such intimacy was not ideal.
Our feelings now out in the open, we had a full movie to silently consider the repercussions of our declarations to each other. I assume Ashley pondered how her very Christian family would take the news, while my worries went in a completely opposite direction. Even though Karen already approved Ashley's and my relationship, I pondered how to deal with having two Mistresses and a girlfriend? Did I actually have a girlfriend? Just a couple of weeks ago I was a virgin and unsure of my sexuality and now I was very confident of who I was. The lights dimmed, the first of many trailers began and I suddenly was nervous to reach for popcorn. I wanted to just hold her hand, but even after our declarations and our kiss, I was nervous.
After the first trailer, which I could tell you nothing about as my head ping-ponged inside over my insecurity and excitement, Ashley, sensing my anxiety asked, as she purposely dropped a couple of pieces of popcorn down her very nice cleavage, "Do you want some popcorn?"
I blushed like I had so many times this past several months. "I would love some."
I glanced around slyly, nervous of others seeing before I leaned over and retrieved the popcorn pieces that were lingering on the top of her small but well-showcased breasts. I returned to my upright position as Ashley pointed out, unbuttoning one, then two, buttons on her blouse, "Jenny, you missed a piece."
My mouth dropped open slightly before I quickly leaned over and retrieved the lost popcorn piece from right between her breasts in her white lace bra. I felt a rush, as I sat back up and chewed thoroughly the lucky piece of popcorn. Ashley didn't fix her blouse as she offered me popcorn the traditional way and returned to watching the movie with a sexy smile on her face. I took some popcorn and, suddenly relaxed, I watched the trailers.
A few minutes into the movie, Ashley put the popcorn bag down and entwined her fingers between mine. A chill electrified my spine and a sweet warmth filled my body.
The next hour and half, give or take, was the simplest and most amazing of my life. Everything just made sense. We watched the movie, both of us content to just be together with our declarations and the indescribable warmth that goes with it. Neither of us ever touched the popcorn again, neither of us willing to let go to the security that went with just holding hands.
As the credits inevitably ended, I felt a wave of disappointment, not because the movie was done, but because our first date, this small ripple of perfect time was ending. Real life was so much more complicated than any one small moment of bliss that always ended. Instantly, even as we both sat quietly as the credits rolled, I wondered: now what?
Eventually, we were the only two left in the theatre when Ashley finally spoke, breaking the lengthy awkward silence, "So I guess we didn't eat much of the popcorn."
The words came out of my mouth without thinking, "That wasn't what I was hungry for."
A second later, when I realized what I had just said, I apologized. "I am so sorry, I don't know why...."
My apology was stopped mid-sentence by Ashley's soft lips.
Her tongue parted between my lips and we were soon in a tender, passionate kiss like nothing I had ever experienced. I imagined the fireworks above my head exploding like in the movies as yet another chill of pleasure slid up my spine. The kiss lasted only a fraction of a minute before the lights began to flicker. Ashley asked, "Do you want to come over to my house for a bit?"
"Sure," I eagerly agreed, my loins on fire even though I assumed there was no way we would be able to do what I was craving.
Ashley took my hand, entwined our fingers again and led me out of the theatre. A couple of people noticed, but I didn't care. I was a lesbian and I no longer wanted to pretend otherwise. In a move totally unlike the old me, I even blew a kiss to a guy who was watching us.
In the car, we drove in silence, both of us content with what we had shared and admitted, although I was nervous and excited at the possibilities of a relationship. It was hard to believe that this day started with me attempting, failing and then succeeding in seducing Ms Morgan, was followed by me walking in on my Mother being dommed by Karen and now I was potentially in a real relationship. It was all so surreal, the kind of stuff you read on Literotica, not the stuff that actually happens...yet it all had happened and this crazy day was not yet over.
Pulling into her driveway, Ashley announced news that instantly sparked a fire down below, her tone implying she was thinking the same thing I was. "My parents are at some charity event and won't be home till late."
In the house, she suddenly was nervous and unsure what to do. I tried to help by asking, not so subtlety, "So, where is your room?"
Her face went red, but it seemed to be the tiny push she needed. She grabbed my hand and led me up the stairs and into her room. On the wall were posters of various eighties bands. She apologized, "Sorry, I love the eighties."
"Me too," I said, and began singing, "Wake me up before you go-go, don't leave...."
She joined in and we danced and goofed off, allowing the awkward tension to fade.
Exhausted and giggly, I fell on her bed. She looked at me. I smiled and teased, "Come over here Ashley, I don't bite...hard."
She laughed nervously, but joined me. I looked into her eyes and she mine and I leaned in for the kiss. She closed her eyes and our lips touched. When we first had sex at the cheerleader's retreat it was amazing and somewhat intimate, considering the circumstances and my position at the time as a submissive for Karen. But now, just the two of us, it was different. We kissed with tenderness, exploring each other's mouths. Her hands began to unbutton my shirt, and the anticipation of more tingled all over. Not wearing a bra, a chill went up my back as my blouse was opened. Once she had my breasts uncovered, I returned the favour, pulling, unbuttoning her blouse button by button. Her lace push-up bra showcased her small sculpted breasts. I reached around and unclasped her bra and allowed it to fall between us. I smiled, “We have almost identical breasts."
"Small, but perky," she shivered, feeling the same cold breeze.
"Let's warm you up," I offered, pushing her onto the bed. She pulled me down with her and our breasts drew together, and we returned to kissing. The heat picked up as the kissing became more raw and needy, each of us melting into the other, until there was no more ‘other’...two becoming one.
Wanting to please her, I pushed her onto her back and moved to her breasts. I spattered kisses all over her breasts, before teasing each nipple with my teeth, not hard bites, but nibbles that made her breathing increase. I slid my tongue down her toned belly, past her cute belly button, before reaching her sweetness. I was greeted by a slight gleam on her shaved pussy and a sweet aroma that I wanted to die in. I extended my tongue and began licking, savoring each lick. Her moans increased quickly and after only a couple of minutes of pleasure she begged, "Finger me, Jenny, please."
I slid two fingers inside her hot pussy and her moans increased exponentially. Shy, conservative Ashley left the room and was replaced by horny animated Ashley. As I pumped my fingers in and out of her, she got animated. "Oh fuck Jenny, harder, fuck my cunt harder."
I did, thrusting my fingers in and out as quickly as I could, but it wasn't enough.
"Another finger," she begged and I allowed my three middle fingers to fuck her.
"More," she moaned, "another, please."
I couldn't fathom another finger fitting into her pussy, but I added my pinkie, which her cunt surprisingly easily allowed.
"Aaaah," she screamed, and I was thankful her parents were not home.
A minute later, Ashley clearly on the brink of orgasm, she surprised me when she begged, "Fist-fuck me Jenny."
"Really?" I asked, not able to fathom my hand, although petite as hands go, fitting inside her.
"Fucking do it!" she demanded, "fist-fuck my cunt now."
Her urgency startled me, but with trepidation I did, scared I would hurt her. But like the four fingers, my fist slid inside her wet pussy rather easily. Once in, she began bucking her hips on my fist, literally fucking herself. I watched in amazed awe at how Ashley had transformed from a sweet timid girl to a raging slut so quickly, before realizing I had done the exact same thing in the past month.
Seeing her sweat, desperate to come, I leaned forward and sucked her swollen clit into my mouth. That was the pebble that broke the dam, as Ashley's legs wrapped around my head and she screamed, loud enough I was worried the neighbor's would think she was being murdered, "Fuuuuuuuuuuuuuuuck!"
She collapsed onto the bed as her cum sprayed out of her, like a broken water fountain. I eagerly tried to catch all her sweet nectar, as all the while I continued to fist-fuck my beautiful girlfriend. Her whimpers continued for a long time, as did her orgasm. Finally she begged, "Please stop, I have to pee."
I pulled my fist out, which was surprisingly harder than putting it in, and Ashley scurried to the bathroom. As I lay in her bed, giddy with what had just occurred and hoping she was going to return the favor, my cunt tingling like there’s no tomorrow, I heard the front door open and close.
I quickly searched for my clothes, just as Ashley returned to her room freaking out. "Shit, shit, shit, my parents are home."
"It's ok," I said, trying to calm her down, "get dressed and they will never know." I tossed her her skirt and she quickly pulled it on, just as I finished dressing.
She quickly found her blouse and I made the bed, which was a complete disaster, just as there was a knock on her door.
Her mom announced, "We are home, sweetheart. Can I come in?"
Ashley, her face still just fucked red, looked at me as I jumped on the bed and opened a textbook, answered, "Sure."
Her mom came in, dressed in a beautiful red cocktail dress, looking like a twin to Ashley, not a mother. "Oh, you have company."
Ashley was paralyzed, clearly not used to lying to her mom or almost getting caught having lesbian sex. So I stood up and walked over to her. "Hi, Mrs. Swanson, I am Jenny."
"Hi, Jenny," she replied cordially, adding, "we have heard a lot about you."
"You have?" I questioned, playing all innocent. "I hope it was all good."
"Of course," she smiled, "well, I will leave you two alone. But it is getting late."
“I was just leaving,” I replied.
Once the door was closed, Ashley collapsed on the bed. "Oh my God, do you think she knows?"
"How would she?" I asked. "It looked like two girls studying."
"I suppose," she sighed, looking so cute in her insecurity.
"But I should be getting home," I said.
"I am so sorry I didn't get to...."
I returned to her bed and I put my finger on her lips. "I'll take a rain check." I kissed her, quickly wanting to remember her softness.
We went downstairs and after meeting her father and chatting shortly with her mother about cheerleading, it was decided her dad would drive me home, which was a disappointment as I wanted to spend more precious time with Ashley.
Generic chit-chat later and I was home. I noticed the light was still on at Megan's, but resisted the temptation to go over, even though my pussy was still begging for attention. I figured I would have to pleasure myself the old fashioned way...with my fingers.
Checking my phone before going in, I noticed three texts:
Karen: Answer me, slut!
Karen: I am going to punish you tomorrow, slut!!!
Ashley: Will you be my prom date?
My whole body warmed at Ashley’s six words. My hand trembled as I typed my response.
I would LOVE to be your date.
I sat on my doorstep, eagerly awaiting a response from Ashley that didn’t come. I considered texting Karen, but I didn’t even know where to begin so I figured I would worry about Karen and her threat tomorrow. Today was too perfect to ruin.
Ashley then texted me:
I can’t wait!!! I really LOVE spending time with you and YES you are MY girlfriend.
On cloud nine, I put my phone way and entered the house.
Once in the house, I went to the front room and was surprised for one last time today. For the second time today, I saw my mother in a compromising position...this time she was on her knees between the legs of Mistress Megan.
Megan looked up, smiled at me and asked casually, as if my Mother wasn't currently pleasing her, "How was your date?"