Samantha From My Past Pt. 01: The Bike

This story is a fantasy featuring mostly heterosexual female on male sexual encounters, mostly older participants. Any similarities to real persons is unintentional. All characters are of age and consenting. This is a long read, not a quickie. Slow build to, hopefully, a good payoff. Reflects the author's preferences and proclivities. Not for everyone. Enjoy. If not, thanks for giving me a try; there are many other great stories and authors to enjoy here.

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The sun was already high in the sky, even though it was only late spring. It was warm, in the low 70's, but it would be much hotter later. The road I was on led away from the edge of town, out into the countryside. It felt good to be back riding my road bike. Seemed like I hadn't ridden a bicycle in weeks. Months maybe? It was easy to lose track of time these days.

This part of Washington State, where we'd found the lakeview property, was set with rolling hills, blanketed with old apple orchards and new vineyards. We loved it here. The perfect getaway from Seattle. Just about a four hour drive, if we stopped at our favorite greasy spoon along the Yakima River for lunch. I loved riding along the quiet country roads, where I rarely encountered traffic. And if I did, the cars and farm trucks of the locals gave me a wide berth and a friendly wave as they drove slowly by.

Our house was located on the edge of the small town, about one block up a short hill from the lake. It had afforded us a spectacular view of most of the lake, without the high cost and annoyances of a waterfront property. Which is what we told ourselves whenever we looked longingly down at our neighbors lounging on their wharves at the water's edge. We'd built the house to our specifications, and it was -- by all accounts -- quite spectacular. Not large by modern standards, but with clean lines, a couple of guest bedrooms, and a private pool located in a sundrenched patio out back. A good tech-exit for me when I left a major software company, and my wife's long successful career as a corporate counsel -- also in tech - left us with a comfortable nest egg upon our early retirement. We kept our modest home in Seattle's Magnolia neighborhood, and built this "retirement cottage" for us to spend our holidays and long weekends while maintaining our city lifestyle and friends when we wanted it. Lake, pool, sunshine, wine, new friends: we loved the country lifestyle after two decades in the city.

Of course, that was all before the diagnosis, the shock, the tears, the long decline, the hope, the letdown, the pain and suffering and final (mercifully) peaceful death of my wife. Together for more than thirty years, our marriage had ended in sadness and personal tragedy that so many couples go through. Perhaps fortunately, we'd had no children. No kids or grandkids to comfort and console. It left me somewhat alone in the world. I was born an only child, and both my parents (and hers) passed long before my wife was taken. Thankfully, an extensive network of friends and extended family members on both sides had offered me loving and unending support during the first eighteen months of my grieving process. I don't think that I would ever get over the loss of my wife, but with almost two years since her passing I had transitioned from sorrow into practical numbness tinged with some rare hope for my future. I was getting by day-to-day, and without a job to go to, I was starting to look for distractions to fill my time. I had recently joined a pickle-ball club for fun, on the recommendation of one of my senior neighbors here at the lake. I bought an electric piano and took some online lessons. Kind of half-heartedly if I'm honest. But it was a great learning curve and I was enjoying tinkling amateurishly along with the instruction videos. Then I got my older roadbike out of storage and refurbished it. And now I was out enjoying the mid-June sunshine. It was helping, too. I needed the workout. I'd put on a ton of weight after my wife passed. I wallowed in self-pity. Got no exercise. Drank too much. Ate more. Grew a paunch that my slender frame had rarely exhibited before. But the cycling, and frequent jogs had helped to take care of that. Now, my waistline was within an inch of what it was when I got married. I was very far from ripped, but for a man in his fifties, I was passably fit. The gray hair at my temples, and plenty of salt mixed in with the pepper in my ever-present stubble, pegged my age for anyone that noticed. I wasn't bad looking, although had never considered myself handsome. Some friends once said that I could pass for the actor John Cusack in my prime, and his. But I'd say that was extremely generous.

Whenever I rode, it gave me time to let my mind wander. It was probably the closest I came to mindfulness. Although I liked to think of it as mindlessness. Cranking hard up one of the steep hills, or idling lazily down the other side, I enjoyed the freedom that it brought to my brain cells. It also felt good for my muscles. And I felt fit, even though I knew I was "healthy" rather than truly fit. I had even broken down and bought proper riding shoes that clipped into my pedals, tight lycra shorts (that I wouldn't wear around polite company), a tight riding jersey, gloves and a good helmet. The outfit made me feel more capable than I truly was. But it was better than the worn out board shorts and cotton t-shirts that I'd worn before, which flapped in the wind and didn't breathe when I started to sweat.

And now I was sweating as I came up a short steep hill that hid a blind curve to a downhill run. Just as I came over the crest, and was keenly anticipating the long gentle downward slope on the other side, I rode past a cyclist stopped on the side of the road. As I passed on the way down, I could see something was wrong. The rider was standing beside the bike. The bicycle was resting upside down on its handlebars, and clearly the rider was bent over working on the rear wheel. I braked hard as I passed. Turned and rode back up. I had a decent toolkit in my seat bag and -- hey -- you always stop to help a fellow rider. Maybe a flat tire. I had a CO2 pump with me.

As I rode up to the rider, I noticed it was a woman.

"Hey, need some help?" I asked, dismounting my bike and laying it on its side in the weeds bounding the orchard beside the road.

"Hey", she said, looking up at me. "Mayyyybe?" and laughed.

I noticed she was a little older, probably my age or so. Short. Slim and trim. Still had her helmet and sunglasses on. Dressed like me, in riding gear. Smear of black grease across her cheek where she'd adjusted her glasses or wiped a bug off her face.

"I was in the wrong gear coming up that hill and geared-down part way up. Like an idiot." She shook her head at herself. "Gear changer gave that ratchet-y noise and drove the chain right off the ring."

I looked down at her pedal crankset and saw that, indeed, the chain was driven deep behind the large front sprocket. Usually it goes off at the small ring on the rear wheel. Not this time.

"Oh yeah, that happens," I said. "Been there". Hoping to make her feel better.

I paused and looked up at her face.

"I've got some tools. Would you like me to have a go?" I took off my sunglasses as I spoke. Looking at her through her shades.

"Oh, that would be awesome," she sighed. "If you don't mind. I've been at it for forever. Can't budge it."

She took off her sunglasses and extended a greasy right hand. "I'm Samantha by the way. Sam." She looked down at her grease-covered hand and retracted it with a light laugh. "Whoops," and gave me a small wave instead.

I looked at her, a little recognition.

"Uh, Samantha?.... Sam? Is that you?"

She looked at me vacantly for a second, and then her smile crept back.

"Oh my God, are you kidding me? Chris? What...?" She laughed. Looked around like she didn't know where she was. "What are the chances? I mean... what are you doing here?"

I laughed and smiled back at her.

"Unreal. We've.... I've had a place up here for years now. Spend almost all my time here."

A truck drove slowly past us as we stared at each other. The driver slowed to a stop and leaned out his window. "You folks alright?"

We turned to him.

"Yeah, we're good thanks. Just some roadside repairs I guess," Samantha said to him, waving her greasy hand at him. He smiled, gave a small salute to his ball hat, and pulled away.

She turned back to me. I gulped and my stomach did a small flip.

Samantha.

---

Years ago, probably ten now, my wife and I had been invited to a wedding. Friends of ours -- their son had got married at a waterfront venue on the Olympic peninsula -- the Pacific coast of Washington State. We'd all driven up and stayed at this nice beachfront resort. It was rainy, but we'd had a great weekend and met tons of people. Amongst the friends of friends, we'd been introduced to Samantha and her husband Brian. The ceremony, reception and dinner were held out on the front patio of the resort overlooking the ocean. It was still raining slightly during the ceremony, but we were under a giant marquee, and it was warm enough to be enjoyable and comfortable in our various wedding attire. We ended up sat at a table together with Samantha and Brian, and we'd gotten along just fine while we sipped cocktails and laughed at the speeches. After the speeches, while we waited for the dinner prep, we talked some more with the couple. Brian was a senior executive at a tech company that I'd heard of. He and I spoke at length while our wives chatted. They were both in the law profession and spoke amiably about work and family life. Brian and I got along ok, but I found him to be a bit of a bore. He talked more about himself and didn't ask me any questions about me or my wife. But not in an unpleasant way. Just full of himself and his success. That kind of guy.

A couple of strange things happened that night. The first came when it was our table's turn to make our way through the dinner buffet line. As we all rose to male our way to the buffet, Brian stayed at the table and Samantha went to get his food. She went through the whole long buffet line, picked out his food, served him, and then she went back through the line again to get her own food. It was strange, but it just seemed like she was used to it. He wasn't unpleasant to her. Just kind of expected her to feed him.

Although my eye very seldom wandered through my entire marriage, and I'd never even considered an affair, I will say that Samantha caught my eye that night. Her and Brian were about ten years older than my wife and I. Yet despite her age, which I guessed to be in her fifties, Samantha was slim and very attractive. Her graying hair was dyed dirty blond, but kept short and pulled back in a small bouncy pony tail, with bangs softly framed above her eyes. She had a pretty, pixie-ish face. Big blue eyes, a pert nose and soft lips. Just hint of lines around her mouth and eyes, and a little on her neck that gave her age away. Her figure was trim and fit. She wore a short white dress that night which showed off her incredibly firm and muscular thighs and calves. I knew, even then, that she must work out. Her waist was trim and she carried small breasts high and tight on her chest, with just a hint of small cleavage showing above a relatively demure neckline. She had a small belly pouch, but just a hint. It was when she had brought Brian his plate and turned to leave that I surreptitiously snuck a glance at her behind. Just a quick glimpse. As she walked away I noticed her very cute and round butt, nestled at the top of her tanned legs, swaying under her white dress.

As the night wore on, we enjoyed their company a little more, and then circulated throughout the crowd talking to the people we knew, and meeting some more new people as well.

Later that night when the wedding party was in full swing, both my wife and Samantha's husband Brian -- along with many of the other guests of our age - had turned in early. There were a few of us enjoying the drinks and music, and I found myself chatting with Samantha for a while. Mainly about our lives in Seattle, her grown kids, and the venue where we were staying. Nothing intimate. And I would say there was no spark between us of any kind. Just friendly conversation. We talked for maybe thirty minutes until the late hour and drinks finally caught up with me. I made my round of good byes and good nights to everyone and paid respects to the happy couple, when... well... something happened. Just a small thing, I guess. But it stuck with me. As I walked across the outside patio where we were all sitting, towards the resort entrance, I walked past Samantha, standing at the bar with some other guests. As I walked by, she turned to me and reached out and gently adjusted my necktie. I glanced at her in slight surprise and she smiled and briefly placed the palm of her hand on my chest. "Good night," she smiled at me. It was a gentle and soft gesture. I don't think anyone else noticed. But it did give me that momentary 'huh' feeling inside. A bit of a stomach flip. I mean, I did think she was attractive, but I also found my wife very attractive and was very much in love. Samantha didn't seem inebriated at all, and there had been no previous indication of any kind of flirting between us. But, anyway, yeah. Just gave me a 'huh, how about that' feeling.

Over the following years, we ran into Brian and Samantha at a handful of events. She was always bright and cordial with my wife and I. And although she never repeated anything like that intimate little gesture from the wedding, she always seemed to look at me with a sparkle in her eye.

My wife and I were both on facebook, like the older GenXers that we were, and ended up connected as friends with Samantha and Brian on that platform. We saw their various posts online, and could see that they both enjoyed outdoor activities including hiking, cycling, kayaking and jogging. Samantha always looked very trim and fit in her pictures, and I saw several of her in beach attire that proved she had an amazing body for someone in her early sixties. Some sagging here and there. A little cellulite. But all that was to be expected and I never felt it detracted from a woman's beauty -- inner or outer. Fitness was obviously a priority for her.

In recent years, however, we heard that her marriage with Brian ultimately failed. He disappeared from the social media platform, but her profile and online-life continued. And periodically we'd see pictures of her and her adult kids online, still enjoying life.

And now here she was, at the side of the road, with a bicycle in need of repair.

----

Samantha held her arms out to her sides. "Oh my God, come here." And I leant in for a hug. She was careful not to put her greasy hands on my jersey but wrapped her arms around my back and gave me a quick squeeze with her forearms. I briefly felt her breasts pressed against me, before our helmets clunked together and we pulled away, laughing.

"I can't believe I ran into you here," she said.

"Here you are. Damsel in distress." I smiled back at her. "What are you doing here?"

"I'm staying over at the resort across the lake." She gestured behind her toward the glistening water, just visible across a sloping orchard. "I'm up here for my friend's sixtieth. Girl's long weekend. Starting day after tomorrow, and all that. I thought I'd come up early and do some riding since the weather is..." She gestured to the empty blue sky, "...SO amazing!"

"That's great. It's a nice resort. We used to stay there before we built the place." I pointed back over the crest of the hill. "Our... my place is just that way a little bit".

A shadow crossed her face. "Oh yes. I'm so sorry about Jean. I heard she'd... passed." She looked quickly down at her riding shoes. "She seemed great. That must have been very hard".

"Thank you." I turned and looked toward the lake. "It's been quite a journey. We had thirty years."

"How long has it been?"

"Almost... uh... two years I guess." I looked back at her. "But I'm coming along. Doing fine, day to day, you know."

To change the subject, I looked down at her bike. It was a nice newer model. Not the highest end bike, but a full carbon frame. White.

"Let me see about this chain of yours".

While I retrieved my toolkit from my seatbag, Samantha took her helmet off, and pulled her water bottle off the upside-down frame of her bike, taking a long drink. I glanced at her out of the corner of my eye. As she tilted her head back to drink from the bottle, her white shiny jersey pulled tight across her chest. Tiny belly pouch above the waistband of her shorts. The sun was behind her, and I could just see her white sports bra behind her thin shirt fabric. The jersey was unzipped slightly. Her chest was tanned and freckled above her cleavage. Some gentle lines on her neck as she drank. Her brindle-gray lycra cycling shorts hugged her small tight round buttocks. Her phone was outlined at her thigh, in what must be a slim pocket. Her calves were muscular. Tanned and smooth. My stomach gave another tiny flip. I turned my eyes away.

I knelt beside her bike in the hot grass. She came over and stood close behind me. Bent over to watch what I was doing.

I could see that the chain was wedged tightly. With my cycling gloves on, I tried to work it loose, but could barely move it. I loosened the spindle axle on her rear wheel, then released her brake caliper. I gently disengaged the rear wheel from the frame of the bike, and out of the way of the chain, setting the wheel on the ground.

"You made short work of that," Samantha laughed, standing behind me.

"Let me see if that helps me get better leverage at all. It might not."

Although it gave me more leverage on the chain itself, I still couldn't budge the chain and I couldn't budge the crankset or turn her pedals in any direction. I tried with my tire levers but they were too flimsy. With my limited set of allen keys and other tools, I knew that I could get the crank arms and pedals off, but I wouldn't be able to get the chain ring off. I would need a better tool set.

"It's really jammed in there." I sighed. "I think I can fix this for you, but I'm going to need some more stuff."

I turned toward her and realized her face was right next to mine as she bent over to see. I could smell the soap on her. She smelled good. She stood up straight and backed away as I got up from my knees, brushing off the dirt

"I've got all the tools I need at my garage. If you'll walk with me, it's only about twenty minutes..." I asked. Question in my voice.

She looked down the hill, toward the direction we'd both been headed, away from my place. The road was smooth and quiet between the orchards and fields. Very inviting.

She sighed.

"Yeah I guess I'm not riding anywhere until this is fixed." She looked back at me, her blue eyes clear. "If you really don't mind..."

"Not at all." I looked down at her bike, with its back wheel lying in the grass. "I'll just carry yours if you don't mind walking my bike for me. Saves me putting your back wheel on."

She looked down at her bike and then at mine. "Awesome. Thank you so much."

I walked over and picked up my bike and brought it to her. As I walked back toward her, I caught her take a quick look at my crotch, where the tight black fabric was stretched over the outline of my soft penis laying sideways in my shorts. She looked away and put her sunglasses back on. I wasn't used to being around people wearing this spandex and lycra riding gear. I usually avoided it.

She took my bike by the handlebars and stood with it. I took my greasy cycling gloves off, which were covered in chain oil. I folded them as best I could and tucked them into my jersey's back pocket. I picked up her bike and threw the frame over my right shoulder. It was really light. The chain dangled down behind me but didn't touch my jersey. Then I bent down and picked up her back wheel. It was also light.