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Meeting Rachel

"Would a work retreat turn into something more?"

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Author's Notes

"Names have been changed to protect the depraved"

Work sucks, let's be honest.

That's not to say I'm not lucky. My current job is the best I've ever had, but it's never going to be my passion. I won't ever be one of those rare people who wake up each morning full of beans and excited about going to work. Or at least so I thought.

Let me introduce myself. I'm Jason, a man in my mid-forties, Irish, 5' 11' tall, and I'd describe myself as rocking a full dad-bod and salt and pepper hair. I'm not fat, but I'm a long way from toned too, and I'm not ashamed of it. I live a comfortable, settled life with my wife and two teenage kids. If I'm not in as good shape as I used to be that's because I spend too much time at my desk working to pay for this comfortable life.

Given the chance, I'm actually quite an outdoorsy person. Hiking, wild camping, kayaking, and boating are all activities I wish I could do more of. But alas as I said at the outset, work sucks and my schedule doesn't leave me much time to indulge these passions.

My life is almost perfect in every way so I really shouldn't complain. The only thing that casts a shadow over my otherwise enviable existence is my sex life or lack thereof. Nineteen years of marriage, and nineteen years of a dead bedroom. Despite having "the talk" many times over the years, nothing has ever changed much. Brief improvements for a few months at a time occasionally got my hopes up, but nothing ever lasted long. It has been a huge source of frustration for me over the years, but I'd always held out hope that it was in my power to change. If I just worked hard enough I could do something to fix it, or so I believed.

I'd even made a plan. I started by listing all the things that my wife told me triggered her stress and affected her libido, removing them from her life one at a time. Financial stability - check. Owning our own home with no debt - check. Therapy to help her cope with anxiety - check. No need for her to work - check. This and a hundred other small things I systematically worked on. Each time hoping beyond hope that I could magically revive my wife's libido. If I just got the next thing checked off the list and made her that little bit happier, things might change. Spoiler alert, nothing ever worked. Her extremely unenthusiastic participation once a month (at best) never improved regardless of my efforts.

They say that hope is a drug and it really is true. Now I'm weaning myself off my hopium addiction and realizing that I've checked off everything on my list. I've wasted many years doing it, and it hasn't made the slightest bit of difference. I feel like a fool that it took me so long to admit defeat. I'm not someone who suffers from depression at all, but when the realization hit that it was NEVER going to get better, the downer was severe and lasted longer than it should have. I've got kids so I'm not going to leave, as tempting as that might sound. Working on acceptance was my plan, and as hard as that was I did make a small bit of progress. I focused on leaving behind anger and animosity. I was just left with disappointment and a feeling of emptiness. I didn't expect this to ever change.

It was about this time that Rachel joined the company.

The company I work for doesn't have offices. Everyone is a remote worker and this suited me down to the ground. Flexible hours, working in my pajamas, no one looking over my shoulder. It's not exciting work, but I have to admit it has some perks.

The weekly team meeting on Zoom was a low point though. It mostly consisted of my boss droning on about the latest performance figures, going through each one at a snail's pace. It was the pure embodiment of "this meeting could have been an email". I made excuses whenever I could, but being a team leader meant that I couldn't get out of this hour of boredom very often. I learned to scroll Reddit just out of view of my webcam hoping no one would notice my attention was elsewhere. The entire team sat silently apart from a few words to say that their projects were "on track", and that was it. A pure waste of oxygen. Until Rachel arrived.

Rachel is American and a little bit of a cliché. Her petite 5' 3" frame and naturally blonde hair are complemented by an enticing hourglass figure. She was a high school cheerleader, and at forty-four years of age still retains that overly-cheerful attitude that initially I found a little annoying. Being naturally a little grumpy and cantankerous, I had a hard time believing it wasn't fake. No one could really be that chirpy, could they?

As time went on I got to see that her oddly positive outlook on life was genuine and she was a truly happy person. She'd had a tough life in recent years, beaten cancer, lost a parent suddenly, gone through a messy divorce, and sent two of her daughters off to distant colleges. She'd found herself alone in the house for the first time in many years, which has got to be tough.

Rachel brightened up those dull Zoom meetings. Somehow she managed to get conversations started. People began telling jokes, and our bosses decided to introduce company "fun Friday" events at her request. Those efforts at remote team-building were more than a little cringe, but oddly I found myself looking forward to them more and more each week.

Then we got chatting. At first, it was work-related DMs on Slack, and simple pleasantries asking how each other's day was going. Asking questions about each other progressed to becoming friends quite quickly and we started chatting daily. We clicked. It wasn't mountains of sexual tension from day one, but there was definitely a connection that quickly grew. Without any intention or planning, the messages began to get a little flirtatious, occasionally even slightly sexual in a joking kind of way. She knew I was married. I myself was not looking for anything. But she was on the other side of the planet and I was never going to meet her, so what harm could a little flirting do?

The flirting intensified as the weeks went on. Nothing blatant, but compliments flowed both ways. She mentioned her disastrous dating efforts in recent months and I may have worked my Irish charm and let her know what a date with me would be like. Rachel made me smile - truly smile - for the first time in a long time. I began to realize just how devoid of joy my life had been and how deeply my self-worth had been affected by my dead bedroom. It felt wrong to go looking for affirmation in the flirtations of another woman, but it also felt like healing had begun. After almost two decades of putting someone else's happiness first, I got the tiniest taste of how it felt to follow my own joy, and it was addictive.

I never intended to take it any further. I couldn't take it any further since she lived 6000 miles away, and that helped me rationalize my part in the flirting. Rachel occupied my thoughts and occasional fantasies too, but I was content to leave it there. Real-life and fantasies rarely work well together.

But then it happened. I opened my email one rainy Tuesday morning to find an invitation to the first-ever company team-building retreat.

It was to be an all-expenses-paid trip to a luxury villa in Italy, complete with a private pool, its own cinema, a private chef, and days filled with fun activities in the sun. How could I say no to that? The thought that I would also get to meet Rachel in person actually made the decision harder. How would online flirting translate to real life? What if she didn't like me? If I didn't have a few seconds to think before typing a witty response maybe she wouldn't find me funny anymore? Maybe I should stay away and just maintain the status quo? In the end, the decision was made for me when another team leader couldn't get a travel visa in time. I was now the only leader from our section attending so I couldn't cancel.

In the weeks running up to the trip, I was more than a little nervous. I wanted to look my best so I made sure I had a fresh haircut, bought some new clothes and new shoes, spent far too long choosing a pair of sunglasses, and even started slapping on a little moisturizer on occasion. I'm not a vain man normally, but I was desperate to make a good first impression.

It turns out I didn't need to worry. Stepping through the arrival doors in the airport, jetlagged and dishevelled I had expected to get an Uber to the villa but was surprised to see Rachels's face contorted in laughter above a comically oversized sign with "Welcome back from jail Jason" scrawled on it. I have to admit it was funny and I'll do the same to one of my friends one day, but it broke the ice immediately and from the very first moment, there was no awkwardness between us. I gave her a huge bear hug and a peck on the cheek, proclaiming how good it was to finally meet her in real life.

She looked stunning in a way that suggested she didn't try too hard but just woke up looking this good. I noticed a little lip gloss and eyeliner, maybe a light touch of mascara, but very minimal makeup. Not that she needed it. Her skin was flawless, her eyes sparkled, and her full lips were more inviting than I could have imagined. The physical attraction I'd felt via chats and video calls immediately transferred to real life, multiplying fivefold in the process. Clad in a loose cotton summer dress that hung to mid-thigh in a green and white print, surrounded by a thin white fabric belt. She completed the simple outfit with green strappy sandals and long blonde hair in a loose braid.

After holding the hug just a fraction longer than necessary, I raised my head and looked around for my other colleagues but couldn't see anyone. "Is it just you?" I asked, trying to keep my tone as neutral as possible.

"It's your lucky day," Rachel said. "Dinner was late so everyone else stayed at the villa. I volunteered to come to pick you up. I do hope you are going to make it up to me?"

I grinned like a school kid at the thought of a thirty-minute drive back to the villa with Rachel all to myself. "I'm sure I can find a way," I said with a theatrical wink that drew a quick laugh from her. "Let's get out of this hell hole of an airport and I'll see what I can come up with".

Rachel led the way as we strolled through the crowded terminal, always walking close. She held my arm as we passed through a crowded area, guiding me in the right direction. Her touch seemed to linger, as did her eyes. As much as I wanted to play it cool I just couldn't look away from her either. At the elevator, I subconsciously placed my hand on the small of her back guiding her in beside me. There, crowded behind nine strangers in a tiny metal box she leaned into me and placed her head on my shoulder. My hand slipped around her waist pulling her closer to me as we took the short three-floor ride down to the parking lot level. Electricity crackled between us and I barely dared to breathe in those precious few seconds. It just felt right. She fit against me perfectly, completing me.

When the elevator stopped and the doors slid open I must have done a double-take, shaking myself out of a daze. I caught Rachel grinning at me in a knowing way, mischief written all over her face. "The car is a long way off, sorry," she said in her soft Utah accent. "The parking is so confusing here I didn't realize how far from the terminal I ended up. The silver lining is that they said I could hire anything I wanted, so I may have taken advantage a little."

She wasn't joking. A tall sign with the letter C was outside the door we exited from, and I could see A and B on signs behind us as we walked away from the terminal. After almost ten minutes of walking, in the far corner of a quiet parking lot, near a big sign proudly proclaiming that this was parking section T, we approached a brand new Range Rover that glistened in the amber light of the street lamps. Sleek white exterior, heavily tinted windows, plush cream leather interior, it was a huge step up from the Ford sedan I was used to at home.

"Wow! Sweet ride," I exclaimed. After the briefest pause, I lowered my voice and added, "and the car isn't bad either". It was a corny line I know, and I instantly kicked myself, but while Rachel was blushing furiously she wasn't looking away. A grin spread across her beautiful face. She took a step toward me, reached out, and placed a hand on my chest. "Why thank you. You're looking pretty tempting yourself you know," she said softly, eliciting an immediate response inside my shorts.

I turned, a little embarrassed at my own forwardness, and quickly stowed my suitcase in the trunk. A moment later as I slid into the passenger seat, I got a chance to properly check out the car as Rachel pointed out some of the features and gadgets. Looking around I glanced behind. "Big back seat too," I said with a raised eyebrow.

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"More space for activities," replied Rachel, quoting her favorite Will Ferrell comedy movie "Step Brothers" and laughing. The laugh quickly subsided as she turned back to face me, moving closer. Her lips we suddenly only a few inches away from mine and I could see the desire in her eyes. "Maybe we should try it out?" she whispered, suddenly looking a little shy, and leaving no doubt in my mind that she was serious.

I'd fantasized about this moment for weeks, but now that it was here I froze. I wanted to say something charming, to profess my desire, to pull her close and feel her melt into my arms. Instead, I sat there like an idiot, mouth hanging open, unable to form a coherent sentence. The perfect moment and my social ineptitude threatened to ruin everything.

"It's Ok," whispered Rachel, eyes now cast downwards and her smile fading to obvious disappointment. "I understand."

Her words snapped me out of it and my mind kicked into gear again. I reached out and gently touched her hand, wrapping her slender fingers around mine. She raised her chin, her eyes meeting mine again. Lips still tantalizingly close.

"I want you, Rachel," I whispered. "I don't know how to do this. I've not even kissed another woman for two decades, so I'm nervous as hell, but I can't deny how I feel about you."

I leaned forward, taking in every small detail. The stray whisp of hair glowing in the cabin light, the warmth of her hand in mine, the sweet coconut smell of her shampoo, and then her soft lips as they met mine.

Time stopped as our bodies met. I pulled her in closer to me, kissing her slowly, gently, lovingly. Her tongue danced playfully against mine, and her hand reached up to my hair, grasping the back of my head, holding the embrace tight. The kissing became mutually deeper, more passionate, more urgent. My hand on the small of her back slipped a little lower, cupping her ass and giving it a squeeze. It felt even better than it looked, firm and toned, with only the thin protection of her cotton dress keeping my hand from her smooth skin.

Rachel came up for air, breathing heavily and I took the opportunity to move my lips to her neck. She shivered with a sharp intake of breath as I found the right spot, raising another hand to my hair and pulling me in closer. My lips chased down her neck and along her collar bone, my right hand reaching up to tug the neckline of her dress out of the way, and then moving to cup a breast as my lips moved further. Her breathing deepened as I reached the limits of skin I could kiss without tearing the dress from her body.

I was momentarily disappointed when she moved my hand, but that turned to delight when I realized that I'd simply been in her way. She began undoing the small white buttons that ran all the way down the front of her dress. I moved my hand around again, repositioning it back on her breast but in a way where she could still reach the buttons. Even through the dress and bra, I could feel an erect nipple under my thumb as I unconsciously stroked it across her perfect curves.

With buttons undone to the waist, I didn't hesitate to pull open the fabric folds exposing a lacy white bra. Even though I didn't have much dating experience as a teenager, one trick I did learn was undoing a bra clasp even through a dress. As my lips moved down to worship Rachel's intoxicating assets, my left hand slid around her back feeling for that telltale bra catch. I found nothing. Again I slid my hand across and just found a smooth band with no clasp or seam. A third time my hand moved along the fabric. Had I really lost all of my skills in the intervening years? It seems my attempts we more obvious than I thought as Rachel giggled under my lips. "Here, let me," she said in an amused whisper. "It's a front fastener."

I lifted my head as she reached to clasp the underside of the lace bra cups, sheer and unpadded. In one deft movement, the clasp fell open and exposed the objects of my desire. At least C cups, full and round, and incredibly pert for a forty-four-year-old, with a hint of a bikini tan line and dark areolas. Nipples like bullets standing half-inch proud took my breath away.

"Dayum!" was all I could muster. "You look amazing!"

My lips went back to her mouth, drinking in the taste of her as my hands explored her body, caressing every inch of skin I could reach. I felt her hand reaching for my belt as her urgency increased struggling with the buckle. "My turn to help," I growled, undoing it with a flick of my wrist and smiling.

"I think I need to switch positions," Rachel moaned in my ear as she lifted herself up and stepped over the center console, folding herself into my lap. I reached down and fumbled with the seat, adjusting it back as far as it would go noticing how steamy the car windows were getting. "That's much better," she said. "The front seats are quite roomy too," as she shrugged her shoulders out of the dress completely. Throwing the bra to one side she sat above me, nude from the waist up. Soft skin glowing in the semi-darkness, and a look of true joy on her face. It took my breath away. She was the most beautiful woman I had ever seen. How did I ever get this lucky?

Her hands reached down to my shorts, popping the button and unzipping me. My cock straining at the thin fabric of my boxers. "Mmmmm, what have we here?" she asked as she stroked her fingers softly up my shaft. "It seems you are wearing a lot more clothes than me. It's time for you to catch up."

I reached up and started undoing the top button on my shirt, but Rachel slapped my hands away. "Oh no, you don't! I want to unwrap you myself," she said with a grin.

Fingers still tracing my rock-hard cock with one hand, she raised the other to my chest and kissed my neck. She made short work of the buttons, moving lower with each that popped open. As her lips passed below my pecks she slipped off my lap onto her knees on the floor, moving her lips lower at a tantalizingly slow pace. My hands ran through her hair, but I was otherwise unmoving, pinned in place by thoughts of the approaching ecstasy. The last button came undone and she opened my shirt wide. Kissing just below my belly button, but looking up, her eyes fixed on mine.

Without breaking eye contact she caught the waistband of my shorts and boxers together and began to pull them down. I shifted in my seat, raising up a little to allow her to remove them, but this also pushed my cock closer to her face.

"Well isn't someone eager?" she said, teasing. Her lips touched the tip of my cock as it strained at the fabric. "I best not keep you waiting." A swift tug and my clothes were gone, falling around my ankles and my manhood sprang free. Barely an inch from her face I could see precum already glistening on the tip of my average-lengthed but girthy member. Rachel paused a moment just looking.

"You do have a very pretty dick," she said. "I'm going to enjoy this."

She wrapped one hand around the base of my shaft and gave a couple of gentle pumps, her breasts swaying in the half-light as she moved. Then she leaned forward and licking her lips moved in. First a kiss on the head, then another a little deeper. Then came her tongue. Short and playful at first just licking the tip, and then moving to the full length of the shaft. Teasing and playing as I moaned with desire. A hand cupped my balls as she continued and my eyes closed. A feeling of warmth enveloped me as she took me deep into her mouth, bobbing up and down. Deeper with each repetition. She moved with eagerness and grace, and very quickly my neatly trimmed pubes were tickling her nose as she took every inch of me down her throat.

I was in heaven, living a fantasy made real. Better even. I never could have imagined this. But years of lackluster sex meant that this carnal bliss was getting me much too close, much too fast. I didn't want this perfect moment to end prematurely.

"That's amazing," I whispered to Rachel between involuntary gasps. "But I'm not going to last much longer if you keep it up. Maybe we can swap places for a while?"

Rachel raised her eyebrows, then slowly lowered her mouth even deeper than before, her nose pressing hard against me. I could feel her throat spasm as she controlled her gag reflex, pushing her limits to the max and teasing me relentlessly. Blowjobs were incredibly rare for me, but I had never in my life experienced deepthroating like this. I instantly saw why it could become an obsession for some men. Coming up for air she wiped her mouth on the back of her arm and smiled. It seemed she was enjoying putting on the show almost as much as I was enjoying receiving it. "That does sound tempting," she said. "But I think I have a better idea."

Moving carefully up out of the footwell, she hooked her thumbs into her waistband as she rose. Her dress and panties fell forgotten to the floor as she slid up on top of me, kissing my chest and neck as she went. Pulling me to sit more upright on the seat, and prompting me to move forward a little, she hovered above me. She positioned herself kneeling, on leg each side of me.

"Don't worry, I'm on birth control," she whispered as she lowered herself down.

My cock touched skin and she shifted a little to get into position before continuing. I could feel myself pressing against the entrance to her pussy as she rocked her hips in small circles guiding me into place. Leaning in with her arms around my neck she kissed me hard and lowered herself down in one smooth movement. Our bodies melted together and we became one. Moving in a naturally synchronized rhythm, responding to each other's needs and touch. Breathing each other in, lost in our own universe. Just the two of us. Nothing else existed.

We moved together wordlessly, moans and whimpers expressing all we were and all we needed. Rocking gently, pulling closer, our souls joined. It may have lasted mere minutes, but it felt like an eternity. Her body and her touch hypnotized me.

Rachel leaned back resting a hand on the dashboard behind her, shifting her foot for better purchase, and started riding me faster. In the dim amber light from the street lamps, I could see her almost bare pussy with just a small landing strip as it grasped my cock with each stroke. Reaching down, I placed my fingers on her as she moved, positioning my thumb on her clit, and gently started circling. Her moans of pleasure increased in pitch. "That feels so good. Keep doing that, right there. YES!"

Her legs started to shake and her whole body shivered. Knowing how close she was to orgasm drove me closer and I knew she could feel it as my cock twitched deep inside her tight pussy.

"Fuck me, Jason, fuck me harder. I'm so close. I need your cum in me. Don't hold back!" she screamed.

I didn't need to be told twice. Increasing my pace, I moved with abandon thrusting faster and deeper, caressing her perfect tits as they bounced in sync with my movements. She shivered again, deeper this time, and again. I knew my own release was only moments away. The point of no return was long past.

Leaning forward I wrapped my arms around her, clawing at her back as I drew her in closer. Her skin against mine, her lips meeting mine. We locked together as waves of pleasure simultaneously overcame us. My cock sank deeper inside her wetness and spurt after spurt of pent-up cum filled her pussy as she squeezed and clamped down on my member as her own climax hit. The world dissolved into white and only we two remained. We collapsed into each other.

When my senses returned it must have been a few minutes later. Rachel was on top of me still, her incredible smile just inches from mine, and her warm body nestled into me. We were both still breathing heavily, flushed from exertion. Her skin touching mine tingled with electricity and she held me as tightly as I held her. Moving our heads together we kissed slowly and with a deep passion and connection that to this day I can't fully put into words. "Welcome to Italy Jason," she said with a quiet giggle.

Just then her phone started to ring. Seeing the caller ID from the corner of her eye, she sighed and snatched it up. Pressing the green button to accept the call. "Yes boss, he's here," a brief pause. "Just a small delay at the baggage claim but I found him. We're just heading out to the car now. Yep, see you in about thirty minutes."

"I guess we have to go then?" I said reluctantly.

"I guess so," Rachel whispered, her soft smile turning mischievous again. "But don't be too sad. It just so happens that your room in the villa is right next to mine."

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Written by corkguy40
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