Fun with the Boss

Long time reader and I thought I would share this with you all. It's as close as I can recall to the event (yes it's a true story) so I hope you all enjoy it as much as I did.

My boss Vivienne (not her real name) but is commonly known by all as Viv had booked us (me Danny) into a week-long conference in Vegas and as it commenced mid morning on Monday we decided to fly in on Sunday night. The flight saw us arrive early in the evening and we then proceeded to our hotel booking.

Unfortunately there had been a mix up at the hotel and we were double booked so the best they could offer for the first two nights was a two bedroom suite and they agreed to only charge for a single room rate. We accepted and, as we are used to closely working together sharing a two bedroom suite would be no problem at all.

Viv swiped the card to open the door and we were greeted by a huge room with full length windows around two thirds of the room. To the left was a hallway and three doors. Left and right were the two bedrooms and the middle was the bathroom.

I dropped my case into the bedroom on the right and Viv the same on the left. I entered the end door to see a well laid out and classy bathroom with a huge spa bath and walk in shower but it was the only bathroom meaning we would be sharing it.

Wow this is going to be awkward I thought, sharing a bathroom with my boss, Viv.

Viv smiled and said "Hey let's just make the best of it, it's only a few nights."

"Sure," I replied, "We can just let each other know when the bathroom is being occupied."

Viv smiled and nodded in agreement.

I wandered into the lounge area and checked out the night time view over the city, lights of every colour lit up the evening sky. Viv joined me and asked if I wanted to crack open the complimentary bottle of red and have a glass.

"Absolutely." was my response and she poured out a couple of glasses.

We sat in some very comfy lounges looking out at the view and sipping on the wine and chatted with some work talk for about five minutes before Viv got up and said she needed to use the bathroom. I watched as she walked off and admired her tight butt wiggle as she walked. I had always been attracted to Viv but since she was my boss I knew there were boundaries.

I was divorced and Viv was in an on again off again relationship with her partner. I guess you could say they had a steady but casual relationship.

Viv was just shy of 50 years old, slight in stature and small in the breast department, B cups I would guess. She was a redhead growing up but over the years her red locks have become more blonde. She never wears skirts so my imagination has always been needed when I assessed her legs. Her ass by contrast is tight and some of her pants over the years have allowed her butt to shine in them.

I am short with a stocky build and just a few years older than Viv. My cock isn't huge at around five inches in length but where I beat most is its girth. I can't close my hand properly around the shaft let alone the knob. I have never actually measured it but guess it's about five inches in circumference. I struggle to find girls that can take me easily and my wife took sometime before she was able to take me with ease.

Viv returned and we sat down and talked whilst we polished off the bottle of wine. When that was done and approaching midnight Viv announced it was time to retire for the night. We exchanged farewells and she left for her room. I flicked through a few TV channels and after ten minutes decided I too would turn in.

After the wine I was feeling a little horny so laid down on my bed and grabbed my phone to surf some porn and after scrolling through a few porn vids my hand found my cock and a few tugs saw it at full attention. I began browsing and then found one who was a splitting image of Viv all be it a few years younger. I was several minutes into the video and just getting a bit of rhythm going when I heard a noise that grabbed my attention. I could hear someone moaning.

Thinking something was up with Viv I quickly pulled my boxers on and looked out into the hallway to see what was up. A light was coming from the ajar door to Viv's room and so too the moaning.

I was a little curious so I just stood there in the dark listening to her moan then something that surprised me was when I heard her softly call my name.

"Mmm...ahhhh...yes...yes, Danny."

Damn I thought, is Viv really in her room masterbating and thinking of me. Could this be true that the lady I have been working alongside and lusting for over many years was pleasuring herself at the thought of me?

I had to know so I tried peeking in the gap of the ajar door but couldn't see anything except the head of the bed and a lamp glowing. My curiosity got the better of me so I carefully and slowly pushed the door open a little more to see if I could get a look at what was going on. I could just make out Viv's top half and her naked breasts were visible along with some very pronounced nipples.

A hand played with one nipple and I could see her arm moving to what I imagined was some pussy rubbing action.

Now I am not sure if it was the wine or what but in my excitement I stumbled a fraction and my head bumped the door enough to make a small noise.

"Fuck!" Viv exclaimed as her eyes darted in my direction and I thought fuck I'm done for now.

I turned to head back to my room but Viv called out "Stop!"

I did and slowly turned around to see Viv now approaching the doorway. Her body was amazing, pert little breasts with some slight sag and very errect nipples. A liitle bump of a belly sat abive a triangle of hair, however she had an annoyed look on her face.

The next thing I felt a hand grab my hard cock through my boxers.

I looked into her eyes and her look had changed to one of lust as her tounge flicked up over her top lip.

"Hmm," she said as she gave me a gentle squeeze through my boxers before I felt her breath on the side of my face.

My cock responded to her touch by jolting a couple of times. I heard her gasp when she felt its girth and her breathing quickened.

My response was to push my boxers down so her hand could feel me without any material in between. No words were spoken, Viv just explored my cock along its length and around its girth with first one, then both hands.

After what was probably only 30 seconds Viv pulled me by my cock into her room and she sat on the edge of the bed. My cock was now around chest height on her and I felt her breath on my cock as her hands continued to explore my cock. She gasped.

My mind was going a million miles an hour at what was happening then I watched her lips press against the head of my cock. Her tongue gently flicked across my knob as she caressed its full length along the underside with her hands.

"No way," I heard her say as she continued to explore my cock with her lips and tongue. "You have the thickest cock I have ever seen and I don't know how you hide that thing but I am going to have some fun tonight."

"You will be right, I softly uttered. I haven't met anyone yet that can't take me, it's just going to take you a few minutes to get used to it."

"Gee, I don't know, its thicker than my arm, you are going to need to go easy on me or I won't be walking tomorrow."

A smile came across my face at thought of her struggling to walk tomorrow and the reason for it.

I could feel her lips now trying to stretch over my knob and eventually felt her lips close over it before releasing it and gasping for air. She has never been one to give into a fight and won most of our arguments over the years so I knew she wouldn't be letting this beat her.

I watched her mouth stretch over my knob again and take the first couple of inches into her mouth and she began to bob back and forth whilst her tongue flicked around my knob.

The warmth of her mouth now fully around my cock was immense, I placed one of my hands on the back of her head and grabbed a handful of her blonde hair to grip on tight as she continued to suck my cock and lube it up with her saliva.

"Viv, you have no idea how good that feels, I could let you do this all night but it's time to lay down before my knees collapse.''

She drew back off my cock and said, "Just wait a minute, I'm the boss, you just stand there and do as you're told!"

Well, who am I to argue I thought as her mouth took my cock into it once more. One of her hands was jerking me into her mouth as the other now cupped my ball sack and massaged it.

"Yes boss," was my reply.

A minute went by, and I could now feel my balls start to come to life as they began to twitch as my cum began to build up. I let the handful of hair go and placed my hands on her shoulders before easing her back onto the bed and my cock plopped free from her warm mouth.

"My turn," I said as I climbed onto the bed next to her and began to kiss her passionately whilst my hands explored her body.

I had for years wanted to explore her shapely legs and figure and now here I was. I couldn't believe this was happening, my boss, a woman I had been so attracted to for years, was lying on the bed next to me engaging in some passionate kissing as my hands explored every part of her body.

I cupped her left breast with one hand and toyed with the nipple between my fingers. A groan came out of her mouth in response to my groping her breast.

"Ohh, Danny...dont stop, please!"

My other hand worked its way down her body to her triangle patch of hair and I softly grasped that area for a second before headed down further and I then felt her wetness. Her lovely little clit awaited my searching fingers which then rubbed up and down along the opening before a gentle amount of pressure had my finger enter her pussy for the first time.

"Mmmhhh," Viv moaned at my fingers entering her pussy.

The heat coming out of her pussy was amazing, my wife used to emit an amount of heat out of her, but this was next level.

I broke off the kissing and slid down the bed so my tongue could explore this amazing pussy. I swung my legs around so I was lying next to her and my cock was now back near her upper body.

Viv again grasped my cock and began to give it a few tugs as my nose took in the scent of her hot and wet pussy.

My tongue gently flicked across her clit a couple of times as a finger explored inside her opening. Panting and incoherent groans came from Viv as I began to feast upon her pussy and tongue toyed with her clit.

It wasn't long before her hips started to gyrate and push against my face as my tongue explored its newly found wonderland.

"Fuck...fuck...FUCK!" screeched Viv in a moment of ecstasy.

A jet of liquid then exploded from her pussy and hit me right across my forehead. I didn't stop my licking though and began to lap up as much as I could and savored the sweet flavor that was Viv.

"For fuck's sake will you fuck me with this monster!" Viv screamed out.

I kept going with my tongue and in a few seconds another orgasm rippled through her body, and she writhed around in response to it.

I got up onto my knees and let my hand grasp her pussy as my ring and index fingers thrust in and out of her and Viv began to gyrate on them as her orgasm continued to ripple through her body.

Her grasp on my cock released and I moved down so I was now positioned between her legs which I gently lifted up and rested her calves on my shoulders. My hands now explored her amazing legs either side of my head.

"Please, please fuck me, I need it now," cried Viv.

I took my cock in my right hand and gave it a few quick tugs to use some of Viv's juices to assist my precum lube before pressing the knob against her wet and warm little opening.

Our eyes locked together and a mixture of fear and excitement were present in Viv's eyes. We were going down a path now that could not be reversed.

There was no resistance to the tip of my cock entering but I knew getting the knob in would need an element of gentleness as it took my wife and other lovers some time to adjust to the girth. Once I had half of the head in and judging by Viv's quick panting breaths I just let it sit there for a few moments before applying some gentle hip pressure to push a little more in.

"Arghhh...arghhh," and some wincing followed by a few nervous sharp breaths and I knew it was time for me to press a little harder until I had the head and maybe an inch inside.

The feeling of her pussy stretching over my knob and the first inch was incredible. I held it for a few seconds more before gently pushing into the hilt and paused to savour the tightness of her mature pussy.

"FUCK!" was all Viv could say as my thick cock throbbed inside her muscle clenching pussy.

It was clear from her wide eyes and other facial expressions she had never experienced something as thick as this previously. As I said earlier I am not that long but the girth is my weapon.

Seconds ticked by and I slowly withdrew a few inches before pressing in again. Over the next minute and amidst some gasping and grunts from Viv I began to introduce her to my cock and allow her to settle into its size.

I tried to be as gentle as possible but I was in a state of ecstasy myself, still questioning if this was real or if was going to wake up any second sweating but disappointed.

Reality is that is was no dream!

"Viv, your pussy is so tight, I'm going to fuck you now baby..."

Viv responded by pushing her hips toward me to indicate it was time to start to build some rhythm.

I did this over the next dozen or so strokes before I withdrew my entire cock so the knob made a squishy plop sound on exit then, after rubbing it up and down her pussy a couple of times a gentle press would see it enter again, then after a momentary pause it was pushed hard and to the hilt.

A few grunts and sharp breaths followed by "Holy fuck, that is amazing!" was her response and I smiled to myself.

Here I was, balls deep into my boss who for years I could only ever imagine in my wildest fantasy to be intimate with.

I repeated a number of times the process of a dozen or so gentle pumps before withdrawing and pushing in again until Viv took control rolling me over onto my back and still with my cock buried inside kissed me.

"Thank you," Viv said in a deep and strong voice before fastening her lips to mine and kissing me with an unrelenting passion. She began to really take control of the sex.

Viv began to vary the speed, force and depth of our sex. She would vary the amount in and speed of the thrusts whilst gyrating a little to stretch every internal part of her pussy she could. A full body shudder followed by some internal muscles spasms that gripped my cock even harder if possible, signalled another intense orgasm which again had Viv screeching my name out loud.

"DANNY!"

Viv leant back and took some deep breaths to compose herself as I fondled her pert little breasts and flicked her nipples in between my fingers.

Viv was now in total controll, her ass was slapping against my thighs and her pussy was massaging every vein in my cock. The feeling was incredible.

Viv shuddered and shook again.

My wife and other lovers never had these types and intense repeat orgasms that Viv was having. It was incredible as her muscles would just strangle my cock during her orgasms.

Viv continued to groan whilst riding me with great vigour and ferocity.

"Fuck you are amazing, I could let you ride me like this for hours babe," I replied as I lay back enjoying being riden by Viv.

After five or so minutes of the cowgirl position I rolled her over and ordered that she kneel before me and it was time for me to take charge.

On my knees, kneeling behind her and my cock positioned at the entrance to the little honey pot I saw her brace herself with two hands on the bed head.

I pushed forward in one firm movement until my cock was completely embedded into her tight wet pussy. Viv slid forward under the pressure of my thrust with her chest pressed firmly into the pillow but then using her arms pushed back so she was able to accept my thrusts.

Seconds later I felt her body convulse again as another orgasm took over her body. She shook and collapsed onto the bed. You're not getting away I thought and followed her down again burying myself inside her and pressing her hard into the bed.

"Arghhhh, dont fucking stop you big bastard!" was her response.

My balls were tingling hard, I could feel them swell and in one more hard thrust that resulted in a grunt from Viv I began to pump my cum into her pussy.

"Oh geez," was her response as bolt after bolt of cum filled her pussy.

I just laid on her back for a moment as my cock completed its task of emptying my ball sack, dribbling the last few drops into her warm hot and now squishy pussy.

I eventually withdrew my cock and rolled off her and onto my back as she was gasping for air.

"Christ, how much did you cum, its oozing out of me there was so much?"

"Sorry I guess its been a week or so since my last load left me and that coupled with finally fucking you, my dream fuck, I guess it was inevitable."

She reached over and just lay a hand on my cock and felt it twitch as it withdrew its swelling to its normal size.

"Look at that thing now its slack, it's still as big as any lover I have ever had." said Viv.

"Plenty more to come, you just name the time and date when you want it and I will book you in boss," I cheekily replied.

Viv chuckled and said "No sorry this is a one off, I am your boss Danny, we can't continue this beyond tonight."

"We will see," I said, "Once you have had this once nothing else comes close. Besides I haven't been in your butt yet."

"No way you're putting that in there," Viv replied.

"Again we will see," I responded as I kissed her and held her in my arms.

She kissed me and snuggled up to me as we drifted off to sleep.

I was awoken in the early hours of the morning with a soothing sensation and then realised Viv had my cock in her mouth, slobbering all over it as in order to lube it up so she could swallow it easier.

"Morning boss, you up for more already are you," I said.

"Mmhmm" was the muffled reply, she wasn't pulling that cock out of her mouth.

Her cock sucking action was awesome and she had now found a method of dealing with my size. I just lay there enjoying the attention I was receiving.

After a couple of minutes of this she withdrew my cock from her mouth, eased herself back up the bed and gave me a sloppy kiss.

"I'm off for a shower, it's just after seven and we have to be downstairs soon," she uttered as rolled out of bed and left the room.

I lay there for a second as I hear the water running in the bathroom which was the shower. I stumble out of bed with fully erect but wet cock jutting out in front of me and head to the bathroom.

Viv was under the running water, eyes closed and savouring the warm water as I entered the shower too.

My hands reached up and found her pert little breasts from behind and gave them a bit of a gentle cupping squeeze.

Viv asks "Hey sweetie, can you do my back please?"

I grab some soap and begin to lather up her back, enjoying the feel of her soft white as snow skin. Its daylight now and I am able to take in all her beauty. Her butt is perfect in shape all be it for a near fifty year old. Yes it has a slight sag but it makes my cock throb in response.

I press my erect cock against her but crack and feel the soft cheeks tense up in reaction. I then push into the depths of her sweet butt cheeks looking for the tight little but hole.

"Not in there today, I'm sorry babe, you are too big for me," Viv remarked.

I lift her left leg up so her foot is resting on the shower wall and feel with my left hand for her pussy opening. I give it a quick probe with my fingers before aiming my cock at the entrance. I feel Viv brace herself as I smoothly enter her from behind in one long slow movement.