Episode 20: My Boss And The Babysitter

My place of work was ‘Movie Bin’, an independent video shop that was owned and run by 37 year old Leanne Brown and I was her only employee, not that I was complaining as you will soon find out why. The store, which was situated in the local high-street, was located a short 10 minute walk away from my house. It was 1/3 of the way down the precinct between Mr. Henri’s Hair Salon and Cuppa-Con coffee shop. As I walked into the video-store, I was pleased to see my boss was already there; it meant that I did not have open the store. “You’re right on time” Leanne said, smiling at me “In fact, you might be a little early today”. I nodded and said that “As I’m feeling better, I decided to get out of bed and back into the swing of things”.

As I went into the backroom to hang up my coat and bag, I noticed Leanne checking out my ass as I walked by. Leanne Brown was a middle-aged woman of 36 who had the kind of body that teenage boys, including myself, fantasized about and wanked over as she was a MILF. I knew that she might’ve had a thing for me from the moment I started working at the store. There had been a handful of other people who had interviewed for the job but she had given me the job as she said I was cute. Once Id put my coat and bag in the backroom, I sat behind the counter and my workday began. Some mornings can be a bit slow which they were this morning, so I spent most of it reading a Star Trek novel and drinking coffee.

About 45 minutes after I got to work, Leanne joined me behind the counter and sat next to me. “So, seen any good movies lately?” Leanne asked with a smile. We both laughed as the quietness that had descended on the store was broken. “Nothing to write home about” I replied, “How about you?”. She replied with “Same as you really, nothing of note”. We made small talk for a few minutes then as she got up to serve a customer, she did something that I was not expecting her to do: she put her hand on my crotch and gave it a quick squeeze. She looked back at me, winked then went on to serve the customer. My cock was already hard when I went to work and after the crotch-grab it felt like it wanted to get even harder.

Once the customer had been served and left the store, Leanne came back behind the counter and sat next to me once again. As Leanne rested her head on my shoulder, she slipped an arm around my waist and said “So, you are pleased to see me”. I nodded and replied that “When you’re a good a boss as you are, of course I’d be pleased to see you”. She rubbed my leg then slid her hand back onto my crotch and gave it another squeeze. I decided not to tell her about Ariadne, but I suspected that she knew about Ariadne already. As I sat there with her, I realized that to some people it might look like I was cheating on Ariadne, but how can I cheat on her if all I am doing is letting my boss rest her head on my shoulder and squeeze my crotch.

I would indeed cheat on Ariadne but sooner than I’d thought. For the rest of the day, Leanne did nothing more than grab my crotch and tell me she liked me. When she said this, I always replied that I liked her, and much to my annoyance that is as far as we went. When it came time to close for the day, and as I was about to leave, Leanne said to me “Next time, we’ll do more than just grope”. She also patted me on the bum as I left the store which felt good. As I walked home, I knew that next time I went to work that I’d end up doing something with Leanne. And that gave me reason to want to get to work early the next time. When I got home, I was surprised to see that Ariadne’s car was not in the driveway.

It was not parked outside on the street, which I found odd. When I stepped in the back door, my first words to my mother were “Where’s Ariadne?”. My mother told me that she’s not here and that she has a shift to cover at work for a sick friend. She then told me something that I had not expected her to tell me. “I’ve arranged for a babysitter to come over” she said, “She should be here soon”. I did not let my mother know just how angry I was, though I was more than sure that she could tell. “Why do I need a babysitter?” I asked, “Why can’t Ariadne stay and keep an eye on me?”. My mother picked up her bag and told me “Because she has to stay at her own home tonight as she has to be at home to receive an important phone call”.

I grunted in annoyance when I realized there was nothing that I could do about it; but that did not mean that I had to like it. “I do not need a babysitter that is not Ariadne” I told my mother “So unless she is going to come back, I’ll be in my room”. Without saying another word, I grabbed a Dr. Pepper from the fridge and headed to my room. Thankfully my mother did not follow me, and I was able to relax and slowly calm down and drink my soda in peace. As I laid on my bed, my thoughts began to wonder as to why Ariadne could not have taken the phone call here instead of at her home. After thinking about that for a few moments, I shifted my thoughts to my bedroom as I realized that Ariadne must have tidied up while I was at work.

All my stuff was there, but it had been neatly put away. “She did a good job” I said as I looked around “She did a better job than I did last time I cleaned my room”. While my room was not a shit-hole, it was comfortably at odds with the other rooms in the house. I was surprised at how good my room looked. I sat at my desk and plugged my IPad in, I did not have any emails that needed an immediate response which was a relief for once. I decided to log onto a game for a while, deciding on a game called “Earth War”. After a couple of hours hurling abuse at the game, I logged off and checked my e-mail again. I fired off a few emails to some friends then I turned the IPad off but left it on charge.

I checked where a few of my things were and were surprised to find Ariadne had put them away safely. I downed the last of my Dr. Pepper and laid back down on my bed and soon dozed off. Sadly, my impromptu nap did not last as long as less than 10 minutes later, my mother woke me up. “JAY, THE BABYSITTER IS HERE” My mother yelled from the bottom of the stairs “GET DOWN HERE AND SAY HELLO”. Initially, I just wanted to tell my mother to ‘Get stuffed’ as I had no interest in meeting the babysitter than was not Ariadne. But try as I might, I could not just ignore her as when she shouted about anything, my mother had one of those voices that you can’t ignore; and believe me, I’ve tried.

Her voice was a combination of nails down a chalkboard and the sensation you get when you have a filling, and you bite into a lump of tinfoil. I was annoyed beyond belief with my mother for having got a babysitter in that wasn’t Ariadne. At that moment, I had no idea why my gym-teacher girlfriend could not look after me. I decided to ignore my mother but her voice, once again sounding like nails on a chalkboard, called out “JONJO, GET DOWN HERE AS THE BABYSITTER IS HERE”. I contemplated ignoring here, but I knew that she’d just keep shouting until I came down. “Hold on, I’ll be there in a few moments” I shouted down “I’m just getting changed”. This was a lie of course as I was already changed.

I just said that as I wanted to hold off on actually meeting the babysitter for as long as I possibly could. Finally, after a few moments, I got up off my bed, straightened my clothes and went downstairs to say a perfunctory ‘Hello’ to the babysitter who was not Ariadne. When I went into the living room, I tried my best not to stare to obviously at the blond-haired girl sat in the armchair. “Jay, this is Brook” my mother said, introducing me to the girl “Brook, this is my son Jay”. I shook Brook’s outstretched hand and while smiling politely I said “Hello”. Brook smiled back at me and replied, “Hello Jay, it’s nice to meet you”. Although I did my best not to get caught staring, Brook caught me stealing a prolonged glance at her tits.

“I have to go now” my mother said to Brook “If he is a little twat, smack him upside the head”. I grunted and said to my mother “Safe journey to work mother, don’t drive over any landmines or such”. Now despite how it sounded, my mother knew I was joking. Once she had left, I sat down on the couch as Brook said to me “So, you going to cause me any trouble?”. I shook my head and replied, “I’ll be spending all of my time up in my room, so no”. Brook nodded and said, “That’s fine, that will make my job easier” As I got up to go to my room, Brook asked me “Would you mind just waiting for a few moments, I’d like to get to know you before you exile yourself to your room”. I sighed; I really did not want to be there.

I decided that as I was in no mood to argue, I might as well sit downstairs a while longer. “Fair enough” I replied, “I’ll have a Coke”. Brook nodded and replied, “I’ll be right back” and as she got up off the armchair, I did my best not to make it to obvious I was staring at her bum. Brook was wearing black trainers, stonewashed jeans that were just the right amount of tight around her ass. She was wearing a purple T-shirt which showed off the swell of her impressive looking cleavage. She kept her long strawberry blond hair tied back in a tight bun on the back of her head. While I thought Brook looked and was indeed hot, I was not in the mood for any kind of sexual goings on with Brook.

She came back in a few minutes later with a Coke for me and a coffee for her, and after handing me the Coke, she sat back down in the armchair. “I know you didn’t want a babysitter” Brook said, taking a sip of her coffee “Your mother told me that your girlfriend was supposed to be here”. For a moment I froze as I thought my mother had told Brook about Ariadne, but it turns out my fears were unfounded. “Your mother told me your girlfriend was supposed to stay here tonight” Brook told me “I know I’m not her but hopefully we can still get along”. I had never intended to make trouble for the babysitter, but now I felt slightly guilty for wanting to send my time in my room. “So, what do you want to do?” I asked, sipping my Coke.

“There is something you can do for me” Brook relied “I need an objective opinion”. I nodded and asked, “I think that I can give you that, what is it?”. Brook put her coffee down and got up and told me “This morning I bought an item of clothing and haven’t tried it on yet”. I nodded and asked, “And you want me to give you my opinion?”. Brook nodded and replied that “That is it, yes”. Seeing as I had nothing else to do, I took a sip of my coke and replied “OK, I’ll give you my best opinion”. Brook smiled and said, “Stay here, I’ll be right back”. She quickly left the room, closing the door behind her. I sat back and wondered just what piece of clothing that Brook wanted my opinion on.

I was not really interested in fashion and suspected that she wanted me to tell her if the item of clothing suited her or not. If I was being honest, I did not fuck care about fashion or whatever Brook wanted my opinion on. I just wanted to give her my opinion then go to my room and hurl abuse at a few videogames. But if giving her my opinion got her off my back and gave me some peace and quiet, then so be it. As I sipped my Coke, I hoped that the item of clothing she wanted my opinion on just required a simple answer. One thing that I liked as much as getting laid, perhaps even a bit more than getting laid was peace and quiet. There would be many times where I would like nothing more than to sit or lay in total silence.

When I was at Bretford Court, it was harder to get peace and quiet but since the school had closed down, it was easier to get peace and quiet at home. And therein lay the only problem I could see in my relationship with Ariadne. Even though we’d only spent one night together, I could easily foresee a situation where I wanted some peace and quiet but where she did not. I was sort-of thankful that she had not been able to spend the night for as I was going to be able to enjoy the silence that came from sleeping alone. My peace and quiet was interrupted when Brook called out “I’m ready but you have to close your eyes”. I frowned and asked “Why?” to which she replied, “Just do it please”.

I was annoyed with her now but the sooner this was over the sooner I could go and lay videogames. “OK, they’re closed” I said, sitting back with my eyes closed. I heard the door open and Brook step in, and as I took a sip of my Coke, Brook said “OK, you can now open your eyes”. I did and I almost choked on my Coke when I saw Brook standing in front of me wearing a bright red bikini. She smiled at me and asked “So, do you think this bikini suits me?”. I stammered and managed to only further stammer gibberish. In truth, the red bikini looked totally amazing on her and was responsible for the massive hard-on I was trying to hide and doing a piss-poor job of it. “I can tell that you do think it looks good” Brook said.

She indicated the massive hard-on that was tenting my tracksuit bottoms and said with a smile “That likes my bikini”. I tried to reply but all I could do was stammer gibberish. “So, what do you think?” She asked, putting her hands on her hips. I had to resist the overwhelming urge to tell her just how unbelievably fucking hot she looked, but my rock-hard erection might have given me away. “That bathing suit really suits you” I say to her “If I said otherwise, I’d be lying”. With a smile, Brook turned her back to me and looked over her shoulder and asked, “Does my bum look big in this?”. I could not help myself, I sighed and said, “You have a really nice bum”. Brook turned back to face me and asked, “You really think so?”.

I nodded and replied “Yeah, its really nice”. Brook smiled weakly and said “Thank-you for the compliment; shame the boyfriend doesn’t think like you”. I realized that with her tone of voice, she was fishing for a compliment, so I decided to give her one. “Your boyfriend doesn’t think you look good in a bikini?” I asked. “He thinks I look better in a one-piece” she replied, “He does not like me wearing bikinis”. I frowned and asked “Why?” To which Brook replied, “He says it makes me look ‘dumpy’...”. If what she was telling me was the truth, then her boyfriend was an ass, a fact that I told Brook. “If he says you look dumpy, then he’s an ass” I said to her “You look absolutely fucking amazing”.

Brook then did something that that I had not expected her to do, she cried. She did not cry as in a blubbering wreck; she cried as if she had just been given some heart-warming good news. She sat down next to me on the couch, put her head on my shoulder and hugged me gently. “Does he not treat you nicely?” I asked as I put my arm around her shoulder. “He says I’m dumpy” Brook tells me “He says my figure is to ‘straight’ and I don’t have enough curves”. After what she had just told me, it was evident that her boyfriend was indeed a total ass if he could say those things about/to her. “You deserve better than that ungrateful ass” I said to her, and almost right away Brook wiped away the tears from her eyes and looked directly at me.

“You’re nicer to me than my boyfriend is” Brook says “You’re just so...” She then leans in and kisses me gently. She breaks the kiss a few moments later and just looked at me, she still had tears in her eyes, but she looked really hot. “Are you sure about this?” I asked “You do have a boyfriend”. Brook wiped away a tear and replied “Of course I’m sure about it...”. She leans forward and kisses me gently then holds my hand and asks “Shall we go upstairs?”. I nodded and replied “I’d love to”. Hand in hand, we got up off the couch and went upstairs. As we walked up the stairs, I stole a few glances at Brook’s bikini-clad bum. “What do you want to do first?” I asked as we entered my room and lay down together.

“Let’s just kiss first” Brook replied; which is what we did. We wrapped our arms around each other and stuck our tongues down each others throats as far as we could get them. As we rolled around on the bed in the throws of kissing passion, I felt my cock ache to be inside Brook. As we kissed, I put my hand under her bikini top and gently squeezed her left tit; and let me tell you that her tit felt just as good as it looked. We broke the kiss and Brook looked at my hand on her tit and with a smile asked me “So, how does it feel?”. I sighed and told her “It feels just perfect”. I moved my hand across to her right tit and gently squeezed it. After a few moments of squeezing her tit, Brook asked “So, do you want to get in me now?”.

I smiled and said “I’d love to”. We kissed for a few more moments and then got off the bed. I ripped my clothes off as fast as I could, but Brook undressed quicker than me as she was just wearing a bikini. As she stood before me naked, I smiled and said “You look perfect...”. She smiled and relied “Thank-you; I’m sure you will as soon as you’re undressed”. Realizing that I had stopped undressing, I quickly removed the rest of my clothes and soon we were both naked in front of each other. Brook looked fantastic naked and I could not wait to get up inside her. She stepped up to me and gently stroked my erect cock for a few moments before she knelt down in front of me; my erect cock was directly facing her.

“You’ll enjoy this, it will get you in the mood” Brook said with a smile, to which I replied “I’m already in the mood...”. She winked at me as she pursed her lips, placed them at the tip of my rock hard cock and gently pressed her head forward, slowly taking the entirety of my cock into her mouth. I had to do my best to not allow my knees to buckle as Brook began her oral work. Now as you have already read, I’ve had blowjobs before and I can tell you that each one is different depending on the girl giving it. Due to the illicit nature of the blowjob I was getting from Brook, this particular oral attention was knee-wracking fantastic. I did my best to keep my knees from buckling, and Brook picked up on this.