Episode 23: Banging My Boss

After a few minutes of driving in silence, Leanne turned to me and asked “Do you have a girlfriend?”. I smiled and replied “No, but I suspect I might have one soon”. Leanne smiled and replied “I think that is a distinct possibility”. I was suddenly nervous upon hearing her last words, this would not be the last time that I would be nervous as you will read about later on. As we turned a corner, Leanne stole a glance at my crotch and the erection that was bulging in my pants. “I see that you’re all ready to go” Leanne says, reaching down and giving my crotch a squeeze “I cant wait to see this and the rest of you in all your naked glory”. I nodded and replied “And I cant wait to see you in your naked glory as well”.

After a further 10 minutes of rather aggressive driving, we arrived at Leanne’s house. “OK, here we are” Leanne said with a smile as we got out of her car. She grabbed me by the hand and led me into her house, closing the door behind her. Once we were in the hallway, we wrapped our arms around each other and kissed passionately; safe in the knowledge that we would not get caught. “So, would you like a drink?” Leanne asked as she broke the kiss “Or shall we go straight to bed?”. I smiled and replied “Why not get a drink and take it to bed”. Leanne smiled and said “Now that is a good idea”. She went into the kitchen and got hold of a bottle of scotch, to glasses and two cans of coke and said “OK, let’s go”. I could not agree quicker when I said “Lead the way”.

As we went upstairs, I could not help but steal a prolonged glance at my boss’ ass and even through her jeans, it looked good. “Enjoying the view?” Leanne asked, to which I replied “It is a fine view, so yes I am”. When we got upstairs, Leanne guided us into her bedroom where we wrapped our arms around each other and kissed passionately. As our tongues swirled around in each others mouths, I put my hands on her bum and squeezed it gently. If my cock could have gotten any harder then it would have done. “I’m so glad you could come over” Leanne said as she broke the kiss. “I’m glad to” I replied with a smile. I looked into her soft brown eyes and judging from the way they gazed at me lovingly, I knew that this was going to be one hell of a night.

“Lets get undressed” Leanne said “Then we can get in bed”. I nodded and replied “As if I would go to bed with you while I’m still fully clothed”. Leanne smiled and took a step back and began to undress, and within a few moments she was standing in front of me totally naked. “Oh wow...” was all I said as she put her hands on her hips and asked “So, do you like what you see?”. I smiled and relied “You look like perfection”. She turned her back to me and glanced over her shoulder at me and asked me “And what do you think of my bum?”. I sighed happily and said that “Your bum looks just peachy”. She smiled then told me “Now its your turn”. I wasted no more time and pulled my clothes off quickly and was soon naked with my cock standing straight out in front of me.

I was not as nervous as I could have been as I’d been naked in front of girls before, being naked in front of Leanne felt no different. The only things that was different was Leanne was my 37 year old boss and we were stood naked before each other in her bedroom. “You look just perfect” Leanne said as we laid down on her bed “Just perfect”. I smiled and replied “Thank-you; and you look just as perfect to”. She cuddled up next to me and draped her right leg over mine as she gently stroked my dick. “You do not know just how much I’ve wanted this” Leanne said with a smile “Or how long I’ve wanted this”. As we lay in bed together, the only sound that filled the room was the sound of the rain that had started to pour down heavily.

As I laid next to Leanne, I began to feel like we were like a typical boyfriend & girlfriend couple, albeit one with that had a bit of an age difference. Now as I’ve mentioned before, I do enjoy a spot of naked cuddling but this usually happens after I’ve fucked the girl/woman but not before. I must admit that just cuddling someone naked is something that I always enjoy after sex but now I’ve discovered just how much I enjoy naked cuddling before sex to. It was something that I was going to have to do more of, be it with Brook, Leanne or any other girl/woman that I end up in bed with. I was not complaining about naked cuddling with Leanne, I was just used to doing it after sex. We just laid there in silence for a few more minutes before Leanne asked “Want me to get on you?”.

I nodded and replied “I want nothing more than you to be on top of me”, which at that very moment was the truth. We kissed passionately for a few seconds before Leanne broke the kiss and straddled my waist. She reached down and gently took hold of my fully erect cock and fisted it to her cunt-hole. “Do you want me to wear protection?” I asked her, to which she replied “No, I want to feel you inside me, not some piece of rubber”. We just looked each other in the eyes for a few moments, neither of us saying anything. “Oh wow...” was all I said as she slid down my cock, taking it all all the way inside her in one swift motion. When it was all the way inside her, she looked down at me as she took my hands and placed them on her slim waist.

With the same look of unbridled love on her face that I had seen earlier on and the previous day, Leanne said “I love you Jay, even though you’re only 14 I really do love you” to which I found myself replying rather swiftly that “I love you to”. Even though I uttered the words, I found it hard to believe that I told Leanne that I loved her. Even though I’d known her for 2 years since I was 12 and despite the fact I was inside her, I found it hard to believe that I said I loved her. It still felt a bit disloyal to Brook what I was doing with my boss. As I looked up at Leanne, it suddenly dawned on me that the reason that I told her that I loved her was because I really did love her more than any other girl or woman I had been with at that point in my life.

I found myself rationalizing this as I did not say that I loved Brook until I was actually inside her. And as I have previously stated, I did not love Brook. I was shaken out of my reverie by Leanne as she gently groaned as she used her leg muscles to raise herself up my cock before lowering herself down again. She waited a few moments before raising up then lowering down again; she wanted to take things slow which was just fine with me. “Hold me” Leanne said gently “Hold onto me”. I did as she said and gently held her slim waist as she slowly bounced up and down on my dick. As I held her, I could not help but try and think just why she liked me so much. It was obvious why I would like her as she was a total MILF and was fucking amazing in bed.

As I have mentioned previously, Leanne was the type of woman teen boys would fantasize about and then think of when they’re tossing off. Thankfully I did not have to do that as I had the real thing. I was shaken out of my reverie by Leanne taking my hands and moving them off her waist and putting them on her tits. “This is just what I need” Leanne said, groaning in pleasure “You are just what I need”. I smile and reply “This is the best feeling ever”. What I said was technically true; fucking WAS the best feeling ever, plus the hotness of who I was fucking made it feel better, and lets not forget that the illicit nature of what I was doing with my 37 year old boss made the fuck even better than it normally would have been.

A few minutes later, Leanne took my hands off her tits and held them gently then looked down at me and said “I really do love you”. And before I could say anything else she let go of my hands, leaned down and kissed me passionately. And as our tongues swirled about in each others mouths, she kept sliding up and down my cock. And as Leanne kissed me, she wraps her arms around me. We continued like this for a few moments before Leanne sat back up and placed my hands on her slim waist once again. For the rest of the fuck neither of us said a word. It was not much longer until she started bouncing up and down on my cock faster and faster, telling me that “I’m almost there” and a few seconds later she told me “I’m going to cum” which she did a few moments later.

I held off cumming myself for as long as I could, but Leanne’s accompanying groans of pleasure as she came was to much for me and I could no longer hold back. “I’m cumming” I groaned out in pleasure “I’M CUMMING”. I gritted my teeth and groaned out in pleasure and said “HERE I CUM...”. Using her cunt muscles, Leanne griped my cock as it unloaded its full load of cum into her flat middle-aged belly. I thrust upwards to meet her bounce as the last drop of my cum was deposited in my boss’ pussy. We stayed like that for a few moments to make sure the last drop of my cum was inside Leanne’s belly. Once when we’d both come down from the pleasure of the orgasm, she climbed off me and collapsed on the bed next to me.

We just laid there in naked silence for a few minutes, gently holding hands. After a few minutes had passed, Leanne turned to me, sighed and said “That was just right, just what I needed”. I wrapped my arm around her waist and replied “You were the best”. What I said to Leanne was technically true though heavily edited, so to speak. When I said that she was the best, she WAS the best as in the best I’d had today. I just did not tell her that last art nor did I tell her about Brook or Ariadne as I wanted to keep seeing both of them. For the next few minutes, we just laid in each others arms in silence. I felt good after fucking my boss as Id always had a thing for her which was now a physical thing. “Would you like a drink?” she asked as she sat up and got the scotch and glasses.

“Sure” I replied. I had not had very much alcohol at this point in my life and so Scotch was something new to me. She poured scotch into the two glasses and handed me one and said “Bottoms up”. I downed the scotch in one shot and it almost chocked me. Leanne smiled as she sipped her drink and asked “So, smooth was it?”. I coughed a few times and replied “Oh yeah, smooth as ice”. Leanne downed the last of her scotch and said with a smile “I should have warned you that the scotch can have a kick”. I must say that I enjoyed my first taste of scotch and as I tried to out the empty glass on the bedside table, I almost fell out of bed. “I think one glass is enough for you” Leanne said with a barley suppressed giggle.

“I agree” I replied as I got back into bed “Though the drink was not without its charms”. As Leanne cuddled up to me, I asked her “So, what shall we do for the rest of the day?”. For a moment, Leanne smiled at me and said “What ever we want to do”. Seeing the faintest hint of a smile forming on my face, Leanne asked “You have something in mind you want to try, don’t you?”. I feigned ignorance and replied “I have no idea what you are talking about”. She kissed me on the cheek and asked “Oh come on, you can tell me; what is it?”. I smiled and said “It involves sticky-tape, the living room and the ottoman”. She looked at me with a confused expression on her face and asked “And just what does all that involve?”. I chuckled and replied with “Hey, you asked me to tell you”.

She rolled over and straddled my waist and replied “I’m not complaining, I’m just curious as to what you’ll need that stuff for”. I held her slim waist gently and asked “Do you really want to know?”, she nodded and replied “Of course”. She then frowned and asked “Does it involve me bent over the ottoman? And possibly tied up with the tape?”. At that point I was sure that she would turn me down and say what I had in mind was ‘perverted’ or ‘disgusting’ but I was wrong. “Let’s give it a try” Leanne said with a smile “As your girlfriend, I want to know what turns you on and how to keep you happy”. She climbed off of me and got out of bed. “Well, what are you waiting for?” She asked with a cheeky smile “There is sticky-tape in the living room”.

I smiled and got out of bed, Leanne took me by the hand and as we headed downstairs the most annoying that that could happen actually happened; someone knocked on the front door. “Just a second” Leanne called out. She turned to me and said “Go back upstairs”. I nodded and ran back upstairs, I watched from the bedroom doorway as Leanne quickly put on a pair of shorts and a dressing gown to answer the door. Knowing that I’d not been seen, I went back into the bedroom. For the next few moments, I waited nervously to see if we’d been caught or that the person at the front door had seen me. As I waited, I got the can of coke, opened it and took a sip and it dawned on me just what Leanne said to me a few moments ago; ‘As your girlfriend’.

For some reason, her having said that made me feel very nervous yet I do not know why. I tried to understand my irrational fear but it did no good, I was still oddly nervous at the thought of having Leanne as my girlfriend. It did not bother me this much when Ariadne or Brook said they were my girlfriend so why did it make me so nervous when my boss said it. The more I thought about it the more I began to wonder if I could just get dressed and run, but when I remembered that my mother thought I was spending the night here, that idea quickly fell away. I took a sip of the Coke and took a deep breath; on reflection the idea of just running away made zero sense, but then again neither did my fear of Leanne as my girlfriend.

This would be the first time that I had a fear of someone as my girlfriend but it would in no way be the last. I was shaken from my thoughts when Leanne called from the bottom of the stairs “IT’S ALL CLEAR NOW”. I grabbed the bottle of scotch and went to the top of the stairs and asked “Is it really clear?”. She stood at the bottom of the stairs, removed the dressing gown and shorts then stood naked she asked “Does this answer your question?”. I went downstairs where Leanne led me into the living room. I handed her the scotch and just stared at her body in all its naked glory and sighed. “You like what you see?” she asked, to which I replied “Oh yes, nothing could look better”. For a moment I just stared at Leanne’s naked form happily.

I found myself still hard to believe that a beautiful woman like her would be interested in a scrawny 14 year old like me. “So, what do you want me to do?” Leanne asked, shaking me out of my reverie. “Forget what I wanted to do” I replied “I just want to be with you”. Leanne smiled and told me that “You’re so loving; now where do you want me and the tape is in the drawer”. I smiled and asked “Are you sure?” Leanne nodded and replied “Of course, now where do you want me?”. Even though she had said she was OK with it, I still felt a little guilty about indulging in a fantasy of mine. “Would you bend over the ottoman?” I asked slightly nervously “But I think we can forgo the sticky tape”. Leanne maneuvered the ottoman to the middle of the living room floor.

She smiled and asked “Why forgo the tape? If you want to use the tape then so do I”. I got the tape from the drawer and asked “Would you bend over the ottoman and allow me to tape your hands and feet to it?”. Leanne smiled and said “Of course, this is getting interesting”. I watched as she knelt in front of the ottoman and bent over it. If it were possible for my cock to have gotten any harder at this point than it would have done. I stepped up to Leanne and as I was about to tape her hands and feet to the ottoman, I stopped. “I can’t go through with this” I told her “It just seems so seedy”. She got up and turned to face me and said “If it’s something you want to do, then there’s nothing wrong with that”.

I knew she was right, but I could not help feeling that it felt to seedy and perverted. “It sounded like a good idea” I told Leanne “But it does not feel right”. She smiled and stroked my face gently and said “You’re so loving; never change”. She leaned forward and we kissed gently for a few moments, before Leanne broke the kiss and asked “Is there anything else you want to try?”. I hesitated, a fact Leanne immediately picked up on. “There is nothing wrong with having fantasies” she told me “Everyone has them, even me”. Seeing the frown on my face, Leanne asked me “You’re surprised I have fantasies?”. I nodded and replied “Yes, sort of...”. Leanne smiled and asked “Do you want to know my fantasy?”. I nodded and she told me “My fantasy ... is you”.

She leaned forward, kissed me and said “My fantasy was to have you all to myself; to take you to bed and make you my boyfriend”. Her fantasy had come true, which I was more than happy to have been a part of. “I was your fantasy?” I asked “That is really cool”. I must admit that at that moment in time, I felt honored to have been able to fulfill Leanne’s fantasy and was more than a little turned on by it. “So you see everyone has fantasies” she tells me “There is no need to be ashamed of them”. I smiled and replied “But my fantasy seems seedy and slimy”. Leanne hugged me gently and asked “Your fantasy, is it something you really want to do?”. I nodded and replied “Yes, but it feels icky”. Leanne smiled at me lovingly.

She then asked “Would you feel better about it if I said I would do it willingly?”. Again I nodded and replied “Yes, but I’d still feel slimy and seedy”. Leanne then said “Then as your girlfriend, I want to help you with your fantasy...”. She turned around and bent over the ottoman once again and said “Now, use the tape”. I still felt slimy about this but she did say she was willing to take part so I felt less slimy. “I’m going to tie your hands together” I told Leanne as I knelt in front of her then using the tape, I tied her hands together. “What next?” Leanne asked. “I tie your feet together” I replied as I knelt behind her and used the tape to tie her ankles together. “This feels kinky” Leanne smiled “I’m looking forward to what you do to me”.

I then wrapped the tape around her, fastening her to the ottoman and rendering her unable to move or get up from it. I knelt behind her and if it were at all possible, then my cock would have got even harder than it already was. “Are you ready?” I asked. “Indeed I am” Leanne told me “Take me; take me from behind”. I knelt behind her, fisted my cock to her cunt-hole and placed my hands on her slim hips. I then slid all the way inside her, not stopping until every inch of my dick was inside my boss. “Oh yes” Leanne groaned as I settled into a gentle sawing motion “Fuck me big boy, fuck me and fill me with your cum”. After my initial hesitation I must admit that it felt good to be able to act out one of my fantasies, especially one with my boss.

Maybe later on we would be able to try out other fantasies of ours. I moved my hands from her slim waist and slid them up her body then reached underneath and grabbed her tits and squeezed them gently. For the next few moments, neither of us said anything with the only sound coming from our mutual grunts and groans of pleasure. It was not until a bird landed on the window ledge outside that we realized that we’d left the living room curtains open; anyone might see us fucking. “Shut the curtains” Leanne told me “Hurry up, someone might catch us”. I pulled out of my boss and got up; racing towards the curtains. I used the cord to pull the curtains closed, enshrouding the living room in darkness and keeping us hidden.

I turned the lights on and was once again able to see Leanne’s naked and bound form. I hurried back over to her, knelt back down and fisted my cock to her cunt hole then pushed it in slowly. I held her slim waist as I resumed the gentle sawing motion I had used before. As I gently sawed in an out of my boss, I could not help but think about Ariadne for a few seconds. It seemed odd to me that she would suddenly go to jail for benefit fraud; it was more than likely that someone squeezed on her. I was shaken from my thoughts about my former teacher/girlfriend when we once again heard the noise that we’d heard just a short time ago; someone knocking at the door. I froze instantly on the spot while still inside Leanne as we listened as the person knocked at the door.

“Who do you think it is?” I whispered. “Don’t know” Leanne replied “Lets just hope they fuck off quickly”. A few moments later, we heard something being out through the letterbox, I slowly pulled out of Leanne and went to check what had been put through the letterbox. “What was it?” Leanne called out. I picked up the letter and looked over it. “It’s a letter from the supplier for the store” I tell her as I head back into the living room. “I know what it’s about” Leanne said “Just put it aside and I’ll deal with it later”. I put the letter on the table then knelt back down behind Leanne. I fisted my cock to her cunt then pushed it all the way in. I held her hips and resumed the sawing motion and said to her that “I hope no one else knocks on the door”.

With a grunt, Leanne replied “If they do, they can fuck off; I’m not having anyone else interrupt our fuck”. I smiled at her last statement as it was the same sentiment that I had but she stated it before I could. After a few moments, I soon felt the familiar tingling in my cock that meant i would soon be cumming. “Don’t cum yet” Leanne groaned “Hold back as long as you can”. I grunted and answered with “I’ll do what I can”. I did what I could to not cum, but eventually I could not hold it back much longer. I began thrusting in and out of Leanne faster and faster, slamming into her harder with each thrust. Leanne grits her teeth and tries her best not to scream in pleasure as she says “Oh god Jay, I’m almost there...”.

She grunted for a few more moments then she cried out loudly “OH GOOD GOD, I’M CUMMING JAY, I’M CUMMING”, and a second later she did just that. When I felt her cum and heard her accompanying groans of pleasure, that was it I could no longer hold back. I gritted my teeth and told Leanne that “OH GOD, HERE IT COMES”. My cock spasms as the jets of cum squirted deep into her belly. Leanne’s cunt muscles clasped my rock-hard cock tightly as she made sure that every last drop of my cum was deposited up inside her. I groaned out loudly and slammed into her as hard as I could one last time then I collapsed on top of Leanne. For a moment, I just laid on top of her before I rolled off and laid on the floor next to the ottoman.

“Wow...” I sighed breathlessly “That was amazing...”. Leanne nodded and replied “Yeah it was...”. I waited for a few seconds as I got my breath back then I got up off the floor and stretched. I walked back to the drawer where the tape was and got a pair of scissors out and made my way back to the ottoman. “So, it was not slimy and seedy was it?” Leanne asked as I cut the tape. “No” I replied “It was really fun”. I stepped back after cutting the last piece of tape and watched as Leanne slowly stood up. “It wasn’t to uncomfortable for you was it?” I asked. She stretched and replied “It was just perfect”. It was way better than I thought it was going to be, which gave me the confidence to ask Leanne later on if we could try another fantasy of mine.

“So you see, fantasies are not all all dirty and seedy” Leanne said as she gently stroked my cock “Once we’ve had a chance to recharge, we’ll try one of mine, yes?”. I smiled and said “That sounds like fun; which one?”. She smiled and replied “How about we just have a standard fuck; outside at night”. I smiled and said “That sounds really good, a shame we can’t go now”. I opened the curtains then we both sat on the couch. Looking out of the window it was still mid morning which put the dampers on the outside fuck right at that moment. Plus we were both tired and needed to rest for a while before we had sex again. “So, what do we do now?” I asked Leanne. “For now the two of us need to rest” she replied “Plus it’s daytime so we can’t go outside yet”.

She was silent for a few moments, then she said “I have an idea, why don’t we just get to know each other”. I frowned and asked “What do you mean? We already know each other”. She cuddled up to me and said “We need to get to know each other better than we currently do”. She kissed me gently and said “In order for the relationship to work out, we need to know each other better”. In other words, she wanted us to make small talk so we could get to know each other better. “So, where do we start?” I asked “Who goes first?”. While it was a genuine question, Leanne found it funny. “What’s so funny?” I asked, to which she replied “You’re so cute”. She kissed me on the cheek and said “I’ll go first; pajamas or commando?”.

I replied with “At home on my own, pajamas but with you it’s commando”. She replied with “Same with me on both accounts”. In all honesty I wore pajamas or tracksuit bottoms and a t-shirt when I was in bed at home. I was silent for a moment, then I asked “Left side or right side of the bed”. Leanne replied with “Right side as its next to my nightstand; you?”. My answer was “Either side is good for me”. I did not care at all what side of the bed I was sleeping on as long as I was in bed and asleep either on my own or next to someone. “Tea or coffee?” I asked. “Either is good for me, but coffee gets me going on a morning” Leanne replied “What about you?”. I replied with “Coffee all the way”. I practically lived on Coffee.

Both my mother and Matthew joking that if I ever needed a blood transfusion then it would have to be pure black coffee and not blood. As Leanne was about to ask another question, the god-dammed fucking phone rang which ticked me off somewhat. It seemed that there was always something that was seemingly determined to stop the two of us from having any peace and quiet. As Leanne sat up and leaned over to pick up the phone, I yawned and sat back on the couch and stretched. As Leanne talked on the phone, I could tell that there was something wrong judging by the way she was getting increasingly annoyed with who she was talking to. She got up off the couch and began to pace up and down while still talking on the phone.

I watched her as she paced up and down, my cock once again getting as hard as it could. I still found it hard to believe that I’d actually slept with my 37 year old boss and that she now considered me, an average 14 year old boy, to be her boyfriend. No matter the illegality of what we were doing, I was not going to do anything to disrupt it. I stared at Leanne’s bum as she paced up and down. I found myself wondering if I could actually get my cock up her ass. I made a quick mental note to ask her if I could try fucking her up her hot ass. It dawned on me that if she agreed to it then it would be the first time I ever fucked any girl/woman up the ass. This was something that I was looking forward to trying, along with a few other fantasies I had.

“God fucking DAMMIT” Leanne cursed. “What’s wrong?” I asked. “The supplier has sent a delivery to the store today, when I’m FUCKING closed” Leanne replied. I understood her frustration at having a delivery sent out when the shop is closed. It had happened a few times before but had always managed to be put on hold until the following working day. Today though, Leanne seemed especially annoyed at this, and I knew that it has to do with me being at her home. “So, what do we do now?” I asked. “WE do nothing, I have to go sort this out” Leanne replied “You stay here, I’ll try to be back as quick as I can”. I watched as she stormed out of the living room and went upstairs to get changed. For a moment, I just stood there in the living room in silence.

I was going to be left all alone in Leanne’s house while she had to go in to the store to sort out this delivery. This would not only give me some peace and quiet, it would also afford me the chance to poke around the house as I was curious. This would be the first time I would be left alone in the home of a girl/woman I was involved with and I wanted to take advantage of it by having a snoop around. A few minutes later, Leanne came back down into the living room having dressed for work. “I wish this hadn’t happened today” Leanne says as she kisses me gently “But I have to go sort this out”. I nod and reply “I’ll be right here waiting for you”. She kisses me again and gives my cock a quick squeeze and tells me “Feel free to help yourself to anything you need”.

I nod and reply “Thank you”. She kisses me once more before grabbing her keys and heading out the front door. Once I was alone in the house, I briefly considered going upstairs and getting dressed but I decided against it as I enjoyed being naked when I was on my own. I headed from the living room and into the kitchen where I got myself a glass of milk. As I sipped the milk, I began to wonder just what my life would be like if Leanne and myself were actually able to openly be boyfriend and girlfriend. Not that I’d ever planned for our relationship to go public, but I decided to keep it quiet. I finished my glass of milk and decided to have a poke around the house; this would give me the chance to see just what type of woman Leanne was.

I moved from the kitchen and went not to the living room but to the back room through the hallway. Leanne had obviously used turned the back room into into an office of sorts as it had been set-up to look like a home office. I sat down at the computer and looked around the room, the home office looked really good. It also looked like a good place for a decent fuck. As I turned to look at some of the pictures, my elbow clipped the mouse which woke the computer up. I turned to look at the monitor and the first thing I noticed was that the computer was not password locked, which struck me as strange. Why would Leanne not have a password on her computer? My curiosity got the better of me and I decided to have a look at what was on the computer.