[MF] An Office Fling (a long story of cheating)

•Skip to line ‘Room 304’ for the “good stuff”•

•First time story writing too•

As all stories start off this was years ago. I was working for a new company. The company had just dipped their toes into this state and wanted to grow. So in just a few short months I was in charge of training just about everyone. I would either travel the state, which I loved to do, or new employees would come to my main office.

We had opened a new office across the state and a new employee was heading here to train for a few days. With the chaos of trying to grow a company in a new area, you’ll usually find things out at the last minute, which was the case here. When I came in my boss said “hey got a new one coming in from blah blah, she’ll be here in a couple of hours”.

“Perfect, no worries” as I set my stuff down. I logged on checked emails and was engrossed in whatever I could get done before my time was no longer solely mine.

A few hours later, very late morning, the door opens up.

“Hi”. The word clearly spoken behind the most genuine smile ever I’ve ever set my eyes on. A hypnotic smile as rare as identical waves on a beach. In walked an Italian lady I swear in her early 30s – later I’d find out she was in her late-late 40s. Shoulder length straight hair, deep deep brown in color. Slender – not skinny or even slim just slender. The perfect chest size I’d say a large C cup. Everything was proportional. She maybe stood at 5’6” so short in height.

Emma (we will call her) had an energy about her. Very out going, very friendly, one of those people who could get anyone to engage in conversation. all this energy bursts out from behind that unicorn smile that never seemed to diminish. We spent the next few days mostly training, some super light flirting ( this is an office full of professionals ), and your normal ‘get to know you QandAs. I found myself more engaged in the conversations with her than I had been with mostly anyone else. I mean dare I say we struck a friendship there in those three or fours days. Eventually our time ended and she went back across state to her office.

We talk everyday 6 days a week. Business picked up 200 percent in this time as word of mouth spread on our excellent quality service. We cranked in the work hours, some weeks were 70 hours. Everyone – at all the offices were doing this.

All of us were talking and seeing each other more than our own families. If we’re not talking in person while at the offices, we’re working from home late into the night texting.

Funny thing about texting on your personal cell phone, the walls, shields, barriers of professionalism seem to dwindle by minuscule amounts with each and every word sent and consequently received.

Soon Em and I are chatting about almost everything, even late into the night while we’re working from our homes. This kind of schedule put a strain on home lives and relationships. Some couples handle it better than others. Emma’s relationship not too well. They constantly fought and eventually decided to separate. Not divorce just separate. It was during this time she messaged me a lot about it. I listened and did what I could to offer advice, tell her she’s being stupid and so on. We got blunt with each after a while. At one point for a while, she stopped eating and got sickly thin looking. Time moves on and they reconnect and are eventually living together again. She starts to put on weight and one day says “the girls are almost back to them selves again”. My response is “what?”. I had been drinking that night so I was in no shape to comprehend the cryptic language of women. To which she replies “my tits… the ‘girls’ “.

“OH!! Got ya! Well I’ll be the judge of that.” *hit send*

“Wait.. did I just reply with that? Yep sure did. No response. Well this just got awkward. Luckily she’s on the other side of the state and I won’t have to see her tomorrow. After a day or two it will all be back to nor…. “ my thought was interrupted by the notification banner. ‘Em sent you a picture ‘ then another ‘Em sent you a picture ‘. I open the message. The first one labeled ‘before’ the second one ‘now’.

Omg she just sent me two pictures of her tits in all their full naked glory. I went erect immediately. These perfect C cups with little pink poking nipples and a slightly larger than a 50 cent piece, areoles that faded into the breast. When I say perfect. I mean amazingly perfect! No sag. They stayed right where the developed.

I stared forever lusting over every pixel. ‘Em sent you a message’ the banner popes up again. “Well. Judgement?”

“Um uh… Em they’re gorgeous! “ Now keep in mind I’m married, been that way for 10 years. This doesn’t happen to me. Yeah sure I watch porn but there’s something different about it being sent to me for my enjoyment. So my response was idiotic and typical.

“Thank you for the compliment, it’s the least I can do for all your help. You have fun with them but delete them don’t want your wife to see”.

This brought a whole new dynamic to our friendship over the months. It got to the point where she was sending morning pics/vids of her showering or right when she got into the office and I’d reciprocate. Showing her vids of me stroking and getting off to her. I’d write detailed stories of us having sex, some very raunchy and very detailed.

Along comes October.

It’s been over a year since all this started and Emma tells me they want to move over to my side of the state. To start a new and get away from where they’ve lived forever. Can you imagine what I’m thinking. “Oh and I’ll be there for a few days to scope out some places… alone” she follows up with.

*Room 304*

“Ok so do I do it? I mean we’re both married, at most I might get a blow job? Right? I mean a bj isn’t all that bad?” The self justification wheels churning in my head. Ding the elevator doors open. I take one last look around. Well there’s the line. That little space between the floor and the elevator – where you can see straight down . I hop in and cross the line, Push the button, and up I go. Ding doors open, i step out, stomach in knots, I look at the room directional signs. I think to my self “why am I walking so slower now?” Knock knock on the door. Well – more like the slightest lightest tap tap, trying to be inconspicuous.

The door opens almost all the way but she’s not standing there. I walk in and the door closes. Em’s behind the door pushing it closed. She’s wearing tight running/yoga type shorts with a tight form fitting super short sleeved shirt. Showing her amazing body’s figure. She immediately latches her hands onto my cheeks and kisses me. At which point I hold her by the waist right above/on her hips pulling her body into mine. Her arms fold on top of each other behind my head resting on my shoulders as I move to hold her closer, from behind. Pulling her body, firmly into mine. We have to longest most passionate first kiss. It did not end. Each kisses that morning was just a continuances from the very first moment we locked lips.

As we kiss, still standing in entryway, my hands wondered all over her back, and little ass. She had a bra on and some kind of panties. Which I thought was weird. Why put all that on if were just going to take them off to have sex? Still kissing ferociously we did the pseudo ‘kiss dance’ to the edge of bed. With one arm, my hand between her should blades, I leaned her back on the bed, supporting her body while she bends at the knees. Gently guiding my Emma the entire way down, always kissing her. Once firmly laying on her back, her toes dangling of the edge of the bed, Emma naturally opens her legs. My lower body a perfect fit. I pick her up a few inches to slide her all the way on the bed.

I kiss her lower lip and upper lip – I kiss her neck and ear lobes. I kiss across her neck collar. I pull her stretchy shirt off her shoulders and kissed those as well. Slow, methodical, a little nibble here and there. Then a smooch to relieve the bite pain. Her legs bent at the knees, toes pointed straight at the wall I can feel her heels on my cheeks pushing down forcing my throbbing cock into crotch. Her outstretched arms and fingertips pointed at the opposite wall. Clearly making herself vulnerable, opening up her entire body to me, as well as signaling ’pleasure me. Give me, my body, all the attention. ‘ Through my shorts I can feel the warmth of her pussy. I can’t help but to push my hips into her.

I kiss her all over, now removing her shirt then smooching, then kissing, tongue flicking, nibbling her stomach, ribs then back up to her neck. Randomizing everything. Never keeping a dedicated pattern. With her bra still on I slide my tongue under it. I flick over her nipples the best I can. It’s more of an attempt then the actual stimulation.

Her perfume is intoxicating. I’m engrossed in her body, the feel of her skin, the sight of all the perfect imperfections that make her gorgeous, her squirming, the feel of her fingers & nails running thru my hair, her racing heart beat.

Supporting myself by one hand and my hips rhythmically pressing into her. My other hand wonders up and down her thigh and calve. Emma’s legs were smooth. A pleasure to caress. With each pass up her thigh I inch closer to her inner thigh by wrapping my arm around her leg. My finger tips grazing the sensitive inner hips, where her panty line rest between her legs.

Emboldened now by her complete acceptance of continuous physical advances and the fact that her hands are now underneath my shirt, I slide my finger over her clothed lips. A slight brush that was followed by her with a very deep breath. She was soaked. I repeated. Pressing a bit more into her. It did not take long for her to speak up.

“You should actually feel how wet I am.”

There was no erotic tone, no seductive look. It was more like a demand as well as an assurance. Like “it’s ok. This is why we’re here” but it was all we needed.

I looked into her eyes as I adjusted over to make a bit more room and slide my finger under her panty line. Her creamy pussy was indeed soaked her lips almost suspended in her juices I could easily access everywhere. I tease her labia up and down for a bit only contacting her clit when I had to cross her slit to tease up and down her other side.

Her hips were moving instinctively. I swear she was trying to find my finger with her hole I slide off her, out from between legs. My finger followed though I stilled kissed her body. She had pulled off her bra and let her gorgeous tits free. I moved a little up to them immediately sucking on her nipples. As I was, I took note more time and slide my hand down into her shorts under her panties over her mound my finger tip reaching the very top of her slit and going straight for her clit.

I circled and circled. Her body tensed up. I sucked hard on her nipples. Almost trying to milk the them. I rose up to my knees at this point making minimum contact with her. Only my mouth and fingering hand touching her. She tensed up more and I slide my finger in. Her breathing quickened. Emma’s breath drawn deeper into her lungs and exhaled just as forcefully. Slight moans came out between breaths. Those deep moans from inside the depths of her throat.

She slides her shorts and panties off. She couldn’t get them off fast enough. The awe inspiring moment of having her there, in the most vulnerable of circumstances. I’m mean think about this for a moment. She’s completely naked, arms now out stretched grabbing at blankets sheets pillows- anything she hold on to for this ride of pleasure waves. Her legs spread open pussy completely exposed. Her womanhood, usually closed off protected by her thighs, legs, and clothing now openly inviting me in. This cannot be comfortable. I would think every instinct we have is to feel protected, safe, not vulnerable. Then I realized, in this momentary thought, she does. She does feel safe and protected and secure.

I slide off the bed. She tilts her head up to see what’s going on. I peel off my shirt and drop my shorts around my ankles. My cock pops out bouncing. A firm, cut, 6.5 inches. She looks a me smiling while sitting up. She grabs me by the shaft and circles her tongue around my defined solid helmet. Her hand moves to my shaven balls and while cupping them she licks up and down my shaft. Her moist mouth felt amazing, too amazing. I had to pull her off saying not yet. She laid back down spreading her legs, her lips glistening in the dim light. My animalistic instinct took control.

I immediately dove in. Lifting her legs up holding the together slightly pushing her ass up off the bed spreading her checks in the process I finally took my first lick. Starting from her ass up. Yes my very first oral move was bold, very forward, and obviously unexpected as Em clenched up – was well received too. “Oh my god!” She exclaimed. I tongue tipped her butt hole for a bit before moving to kiss her back thighs. Seeing her pussy sandwiched between her thighs I then licked up her slit. My tongue coated in her mature molasses. I would never forget her taste. It stayed with me all day. My face was covered by her juices as I made sure my face stayed buried deep between her legs. No area of Emma’s pussy was left undiscovered. It only took minutes of tongue fucking, clit sucking and swirling to get her to orgasm. The moans were intoxicating and leg quivering hypnotic.

I ate her out as long as she could take it eventually she pushed my head down and off. Half moaning and breath talking for me to stop. Her legs shaking and I guess a loss of strength they fall over my shoulders heels resting on my back.

As her legs drift off my body and fall to my sides I place the back of her knees in my folded arms almost catching them. I grab her by the upper thighs and pull her cute little freshly licked ass the the very edge of the hotel bed. I looked down into her eyes. Beautiful light blue almost a faded blue eyes. I’d like to say I had a little smirking smile but I’m honestly not sure.

Being a very visual person my eyes drifted down her body. Her neck, her upper chest, her tits, her flat tummy, her hips and hip bones, her pubic mound, to her vet shortly trimmed land strip and yes to her gorgeous labium. I wanted to lick again. I wanted to spend all day with my face between her legs. I wanted her to feel the heavens and my tongue to be the transport there, but just as those unconscious thoughts came through me. Something else peeked into view. My tip.

Just merely millimeters from her mature lips I could almost feel the energy from her. Probably just the heat emanating from her freshly eaten pussy, but it felt way more than just that. It definitely felt like an attraction of our bodies wanting to come together.

Still holding her legs up with my forearms behind her knees. I now had her spread wide open. A perfect view of her and I slide my helmet head up between her lips – followed by my shaft. Our first touching. I know all the other previous actions were, are bad but this was something on that ‘next level’. I slid up and down between her lips, making sure my head hit her sensitive clit, followed by my shaft dragging over it.

It was a beautiful sight. I watch as I did this a few times hearing her breaths turn into moans. At this point I looked back up at Em. Our eyes met again. Still humping her, essentially, she gave me that pleasure filled, corner mouth smile, and nodded her head while exhaling.

I slid down one last time arched my hips back further adjusting myself and while still holding her legs up I found her hole with my tip. I slowly slid in and out. Teasing her with my head. Though unintentional. It just felt so good on my head. With each motion I went deeper. I was treasuring each and every centimeter of her wrapping around squeezing a new part of my shaft until I was all the way in. Which didn’t take as long as this reads I’m not long. I’m about 6 1/2 inches.

Once I was all the way in and felt her relaxing I started thrusting and thrusting. In and out over and over. She grabbed at the sheets and was breathing heavily. At one point she grabbed a pillow and covered her face. Still going at it I watched her body. I watched her tits bounced in every direction. I watched my shaft penetrating her over and over. Once the pillow fell away I watch her expressions. I rubbed her clit as we fucked. I’d like to say we went at it for an hour or two. Non stop of relentless pounding. In reality I probably only lasted 15-20 minutes before I had to explode.

When I was close I asked where should I cum? She questioned me confused. Like she hadn’t been asked that in over a couple decades. The I guessed it dawned on her in that very same split second. She hadn’t been asked that because she and I are married. We have our ‘cum spots’ already figured out with our partners.

‘In me!! Cum in me please!!’ I only went a few more thrust before that rush of pleasure hit my tip. I didn’t question it. I pushed soooo deep and let go of control. I squeezed the top thighs, the sides of her hips any where I could as I sent thrust after thrust of cum in her as deep as I possibly could. I pulled her body into mine as I pushed my body as forcefully into hers as I could. I wanted my cum deep deep inside of her. I wanted it to leak out all day long.

After that breathing hard and actually sweaty from sex for the first time in years, I realized I had no choice but to cum inside her. At some point her legs were hers and she used them to wrap around me and was not letting go. She actually held me in place for a minute after we were done.

With her pussy filled and my cock plugging up her hole getting soft she pulled me to her and we made out for a bit. Eventually I fell out of her and could feel the cold ambient air of the room on my shaft and head. It wasn’t until we got up that I saw the mess. It was a soaking of juices on the sheets. I had never seen so much of it. The saturation fell down the side of the sheet at least down the top mattress.

We didn’t say much after that. The reality was coming back slowly. We did take a shower together. Nothing much happened. We kissed and washed each other. She made sure my cock was very clean and I made sure I touched every inch of her again.

Eventually I got dressed and had to leave the room. The rest of the day I had a hop skip and a jump to my steps.

Source: reddit.com/r/gonewildstories/comments/diopos/mf_an_office_fling_a_long_story_of_cheating