Ole Betsy the Wingman

Authors note: This is a Summer Lovin' 2021 entry. Please read and vote for this (and all the stories.) Comments are appreciated too. And special thanks to Winsome Web for her proofreading and editing help.

"Hi Jack. Can we, Umm, borrow Ole Betsy?" It was Julie from across the street, and Heidi from three houses down. And as usual, they were looking good.

Ole Betsy was a tractor. Technically, it wasn't really a tractor, it was a riding lawnmower. But that's just splitting hairs. If it had been just a little older and a little more expensive, it might be an antique. To me, it was just old. But I had a picture of my dad riding it when he was about ten years old with my grandfather standing next to him, and I had been about ten the first time I was allowed to ride it. Legend had it that she was named after a cow on the farm that my grandfather grew up on, and he used to joke that Ole Betsy the cow could go faster than Ole Betsy the tractor. And having inherited caretaker status for this heirloom (or was it junk?) Ole Betsy was now mine.

"Oh, sure. Anytime, let me get the keys to the shed." It was a hot summer's day. And I was now thoroughly thrilled at my decision to buy this house in a neighborhood of homes, all on three-quarter of an acre lots. Sure, the water bill was hell, but I remember seeing Julie for the first time the day I was moving in and thinking that just getting to look at her made it all worth it.

I'm also reasonably handy, and especially in this day of watching "how-to" videos online, fixing things was even easier. And this mower ran flawlessly. Better than new, actually, because modern-day spare parts are simply made out of stronger and more durable plastic than the original parts, so it wasn't the guaranteed broken-down puddle of oil that it would have been under other circumstances.

Except for the shaking, that is. It was still sixty years old, it was still just a one-cylinder gas engine, and the sixty-year-old technology meant it probably shook just as much brand new as it did today. After a few minutes on this thing, your fingertips were numb. A few more minutes your toes. Then your ass. But it was free. It worked. It mowed the lawn, and every time I used it, it made me remember my dad.

# # # # #

I was happy to let Julie borrow the mower. She had borrowed it last week, and I knew just from the few minutes it took to explain the quirks of starting sixty-year-old technology, that she had an aptitude for this sort of thing.

She was a sexy tomboy type. Drop-dead gorgeous, even in her typical casual outfit of shorts, T-Shirts, and flip flops most days I saw her. I had to admit, I felt something strange in the pit of my stomach every time I saw her. She made it hard to breathe. Hard to think. Hard even to speak. But in a good way.

In this odd little enclave of a neighborhood, with affluent residents, she and I were outliers, me who mows my own lawn, and Julie, a single professional on a street full of trophy wives. And for the past year, she and I were interacting more and more, even if it was always under the guise of house-related chores. Julie was more skilled at keeping plants alive, whereas I mainly lifted heavy things for her. In reality, I did anything that led me to spend time around her. She did seem to like me, but I never felt I was viewed the way I wished I was viewed by her. And where the Stepford-wives like neighbors might have endlessly tried to fix her and I up together, there was that deal-breaker. Because (gasp) as I mentioned; I mow my own lawn. The Stepford's though, as I had nicknamed them, tended to also be easy on the eyes.

I was glad that I hadn't thrown out the original steel seat it came with when I bought one of those obnoxious yellow plastic replacement seats. These were the large seats, that almost looked like one-quarter of a Sombrero, a Saddle style seat I think they called it. The vibrations from the steel seat were absolutely unbearable. With the plastic seat, at least I could finish mowing the lawn before all my fillings fell out.

I remembered the week before, she did a nice job driving it, she knew just how to make sure it didn't stall, and she did a very nice job mowing her lawn.

That day, I had stuck around the barn cleaning up a bit, but also listening off in the distance, because I knew it occasionally wouldn't start very easily if you turned it off while the engine was hot. I did notice something odd at one point, and I peeked out to look. She was sitting still, in the seat parked next to her house, but stayed there, just parked, for about five minutes, in a strangely upright position. Then she turned off the engine, hopped off, and practically ran into her house, and didn't appear again for about twenty minutes.

I made sure my phone ringer was on loud, in case she ended up calling me to tell me it had broken down. But I didn't want to be too obvious that I had been watching either. I went back to the cleaning up around the barn, and maybe twenty minutes later, I heard the engine start back up.

I peeked out, and oddly, she was in a different outfit, still shorts and a T-shirt and the flip flops that showed off her sexy ankles and toes, but definitely different. She had a few final passes to do before she finished her lawn, then I heard her driving up. And driving right into the barn, perfectly centered left to right and front to back, and hopped off.

"That thing's got some shake to it, doesn't it? Now gimme that gas can, I'll fill it up and bring it back."

"Oh gosh, no don't worry about that," I tried to resist. Except she insisted and wouldn't take no for an answer. What a hot tomboy, I thought to myself. She was taking the gas can and would refill it, even though it was a five-gallon gas tank. For a brief moment, I thought it might be too heavy for her after she filled it up, then I remembered who I was talking to.

# # # # #

Back to the present, with Julie and Heidi at my front door, Julie said, "I'm going to show Heidi how to use it too, if you don't mind? She needs a trim too. Her lawn. I mean her lawn needs a trim too." Julie stumbled over her words.

Heidi laughed out loud. "C'mon, it's not THAT thick. Just a little sculpting is all it needs." I pretended not to notice how much innuendo was contained in that comment. But it also made my little man-brain go into overdrive. If Julie was teasing Heidi about having a lot of pubic hair, did it mean Julie didn't? Could Julie be bald? My head was going to explode.

"Oh, no problem," I said as I got the keys and we all walked around the front of the house to the shed.

I sat back, knowing the Julie knew exactly what to do. She showed Heidi the controls, told her all the tricks about getting it started, keeping it running, and they were off.

I peeped out the window as I watched them drive off. Julie got off after backing the tractor out and driving down the driveway, and I saw her get off and Heidi got on. I couldn't hear what they were saying of course, but Heidi said something and they both laughed.

I had also, of course, noticed their outfits when they first came up, but I tried to keep my jaw in place and not to stare. They were both were in yoga pants and tank tops, Julie in her usual flip flops, and Heidi in running shoes, both of them in baseball caps for a bit of shade. But Heidi's yoga pants were highlighting the outline of her vulva, a spectacular camel-toe. And Julie's were hugging the shape of her ass cheeks. It was only 10:30, but already hot. So for me at least, a man who thinks sweat is a little sexy, it was even sexier.

I only had a partial view of the front of Heidi's house from where I was. I laughed at myself as I went into the house, ruffled through the hall closet for my binoculars, and went upstairs to the guest bathroom, stood carefully on the counter to get high enough to see Heidi's entire front yard, side, and part of the back. I of course turned off the lights and closed the doors, to make sure I couldn't be seen, watching the two beautiful women using my old riding lawnmower.

The one curious thing, was the flip-flopping drivers, always with lots of laughing as they traded spots. Finally, and this was just about the sexiest thing I had ever seen in my life, Heidi sat in Julie's lap, and they went down and back up, still laughing. I noticed that Heidi wasn't really in Julie's lap, exactly. Julie pushed herself to the very back of the seat and splayed her legs apart awkwardly to make room for Heidi, who was perched directly on the hump at the front of the seat. Knowing how that mower shook and vibrated, I couldn't imagine them enjoying the experience. But clearly, Heidi was very eagerly leaning forward, almost enthusiastically. Rocking back and forth a bit, even.

"Nah, it can't be," I concluded to myself. "But what if?" The little gears in my head were spinning, causing the hydraulic pumps in my loins to start spinning too. "She's humping the chair. She's using it to make herself have an orgasm. And that's what Julie did when she went into her house last week!" was the internal dialogue in my head. The practical and sensible part of me tried to be sensible and talk myself out of such a wild theory. The analytical part of me kept staring through the binoculars, and pointed out how the evidence seemed quite convincing. And another part of me was fully erect imagining. And now, Heidi was leaning forward, almost visibly humping the rise of the seat. Could I be right? I remembered years back, I had an unusual online chatting friendship with a 'biker-chick', and she had told me how sitting on the back of a biker's Harley Davidson would make her have an orgasm. Well, if that were the case, I could only imagine what Ole Betsy would have done to her, because Ole Betsy would make a Harley seem like sitting on a cloud. A cloud covered with pillows. A cloud, covered with pillows, while sitting in a Lexus.

They drove up behind Heidi's house. They got off, said something to one another, laughed some more, and went into Heidi's house through the back door. I couldn't figure out what was going on, and other than seeing a little movement through a window one time, nothing happened for about twenty minutes. And every time I said to myself that I was being ridiculous, I would also wait one more minute to see if something happened. Then ten "one-more-minutes" later, I saw the back door open again.

Oddly enough, both of them had changed clothes, just like Julie had the week before. What was going on? They were still in old yardwork clothes, this time shorts and T-shirts, doubtlessly one of Heidi's shorts that Julie was borrowing. But why had they changed?

The next thing that happened made me realize how smart they were. Heidi had something in her hand, and put it to her mouth. It was a small round inflatable pool float, donut-shaped. Why are they so smart, and why hadn't I thought of that? But more to the point, why had they changed clothes?

The pool float inflated, and this time Heidi sat on the seat, now cushioned by the floatie, and Julie sat on the back steps watching, as Heidi made short work of the rest of the lawn.

As Heidi wrapped up mowing, she threw the pool floatie off by the side of her house, then they headed back to my house. Instead of hopping on and sitting in Heidi's lap, which I secretly was hoping for, Julie just walked alongside the tractor, as Heidi drove toward my house.

I practically tripped and fell on my face, but I did manage to get downstairs and come out my door just as they were driving up. This worked well, it made it seem like I wasn't some sort of pervert watching them with binoculars by standing on an upstairs bathroom counter. I laughed at myself.

Heidi jumped off and said, "You park it" to Julie. Julie hopped on and eased the old tractor into the shed. "How'd it go?"

"Fantastic!" They both said.

"No troubles?"

"No, no, not at all. I mean, the vib... I mean the shaking just got to us," Heidi said. She was more outgoing and boisterous, but Julie was still my dream girl.

"Oh god, I know. I should have warned you; it'll make your fingertips tingle."

I noticed a smirk on Heidi's face. "Fingertips. Yeah" she said with a laugh.

"Mine too," Julie was nodding. "Everywhere tingles."

"We did have to take a little break. The seat really did get to us, we needed a cigarette afterwards." As a boy, with a dirty mind, I obviously wondered if she was being dirty, but I pretended not to notice. I also knew Julie at least, wouldn't smoke a cigarette in a million years. I was instead in my mind asking myself, is it wrong that I want to sniff the seat?

"Ok, well feel free to borrow any time. It's summer and rainy, this time of year you almost have to mow at least once a week. "

"Thanks!" Julie smiled her dazzling smile, as Heidi nodded.

"Also, help yourself to it even if I'm not home, but just you two." I happened to have two keys on the key ring that fit the padlock. I gave one to Julie.

"Ok. Actually, I think Jillian down the street is going to want to try this out too. Do you mind?" Yet another of the reasons I had such a crush on Julie. She was always thinking of others.

"No, not at all. I just hope the lawn guy won't get mad at me!" I joked.

"Oh, he'll be ok. He does the edging and pruning too, his job is safe. We're making it easier, in fact," Julie said.

"Yep. Especially with how you keep everything trimmed," Heidi joked. Another pubic hair reference? my imagination went wild. Julie shrugged, as I noticed she tended to do whenever Heidi said something outrageous.

They started walking home. I had turned to make sure the padlock had clicked, but I had also started walking behind them, without their knowing that I was in earshot.

"I'm still tingling!" Heidi quipped to Julie.

"I told you!" Julie said with emphasis.

"Round two?" Julie nodded to Heidi's question.

What were they talking about? And what was Round one? They kept walking away, and I went back to my window. I watched them reach Julie's front door, except I saw Heidi hold Julie's hand and squeeze as they walked in. The door clicked shut, and I knew I might be there for hours with the binoculars. This time around, it was about twenty minutes later. Heidi walked out, looked around to see if anyone was out, and turned around and kissed Julie on the lips. It wasn't a peck. They held hands, lingered a bit not wanting to let go, then Heidi turned around and left.

I admit it. I went straight to my room and pumped my cock, imagining how they might have kissed if they hadn't been outside.

# # # # #

The next day, I needed to mow my lawn. I had meant to do it the day before, but I had wisely chosen to let Heidi and Julie borrow it. And I had meant to do it earlier before the day got too hot, but it was about three in the afternoon now.

I was only about two minutes into it, when I thought I heard yelling. Then I knew I heard yelling. It was Julie and Heidi, except this time Jillian was with them also. they were dressed in beautiful sundresses, all three of them holding glasses of wine. They were a little tipsy, laughing up a storm.

"Get off, we wanna drive the mower." Julie giggled. I was amazed at how Julie got along with everyone. Even with her career, she was also great friends, and found common ground with the women living lives of luxury in our neighborhood.

"Yeah, get off. Some of us want to get off too! I mean, get on," Jillian said. The other two women burst out laughing.

I started to say, "Really? while you're dressed so nicely?" then I realized to just shut up. Why would I want to stop them? "Sure!" I smiled. "I'll hold your drinks! Wow, you're going to be the best-dressed lawn guys the world has ever seen!"

"Well, thank you!" Julie said.

"I'm already tingling," Jillian said with a smirk.

"Just you wait," Julie joked, then continued. "But actually, we should mow your lawn for you. We were interrupting," Julie said, again always thinking of others. I swear she had a halo around her, but maybe it was my imagination.

Julie proceeded to show Jillian how to ride it. It was a shorter lesson than usual, since it was just how to ride it, not to start it, get it out of the garage, etc. Jillian was also a good listener. Julie started Ole Betsy up, and backed out, then took one pass down and up. "Ready?" she said to Jillian.

"Ready!" Jillian climbed on, and made a bouncing motion as she sat on the seat. "And they're off!" she said. Julie and Heidi stood watching as Jillian made a lap. Jillian went down, then came back.

"How'd it go?" Julie asked as Jillian came within earshot.

"I need another lap," Jillian said. She didn't even stop, and turned around for a second run. I wasn't standing right by Julie and Heidi, since they seemed to be having their own conversation, but we were all watching Jillian go back and forth. She came back, and said, "No, no, not yet... Almost there!" And she made one more lap.

"She'll really be tingling by the time she comes back," Julie said to Heidi, but loud enough to include me in the conversation.

"I don't know how you mow your whole lawn, Jack."

"Well, I am going to borrow your pool floatie idea. That was brilliant! The seat is kind of hard."

Julie raised one eyebrow, and I knew in an instant that she noticed my slip-up, that I had inadvertently revealed that I had been watching. And it knows how to use it," she quipped.

"It's quite a massager, I have to say," Heidi said. "Definitely leaves you happy."

By now, Jillian was about back. I thought she'd wait around, but she climbed off, took her glass of wine, said "I'll be at the house." and made a beeline for Julie's house.

"I'm just a bit behind you," Heidi said as she got on the mower. Heidi however, seemed to be ever so slightly tipsier than Julie or Jillian, and she very obviously humped and ground her pelvis against the seat as she started moving off. Julie stayed by me. There was something about Julie, her quiet poise. This was where normally she'd have rolled her eyes at Heidi's outrageousness, but she avoided eye contact this time. I liked this woman more every single time I talked to her.

"You'll never get your lawn finished, with us interrupting you every time," she said.

"I'm having a blast watching you all. This beats mowing by a long shot. Besides, you're helping me mow," I said. But at the exact moment that I said that, Heidi misjudged her U-turn and mowed over about a quarter of the flower bed near the street. Then, she mowed diagonally across the nice symmetrical mow lines that had been established. We both died laughing, with Julie of course saying she'd help me fix it later.

"She may be mowing while intoxicated," I joked.

"We love that mower," Julie said. Then thoughtfully she said, "You're a bit too observant though, Mister Jack. Too observant," she trailed off mysteriously. I wondered what she meant. In my imaginary world, I thought that maybe Julie knew, that I knew, that the three lovely women were having orgasms due to the intense vibrations of my riding lawnmower.

Heidi came back, got off the mower, and stated flatly "I'm going to the house. Gimme my drink." She turned and started walking to Julie's house.

"I'll catch up," Julie said. "Let me finish that side of the lawn, Jack," and she pointed to the side that Heidi had partially wrecked.

She started off, and it took her about three back and forths to finish the side of the house they had been mowing.

She came back, her face flushed, and some delectable beads of sweat on her upper lip. "Hold on a sec," I said, stopping her before she turned it off. "Lemme show you something. Leave it in neutral." I was thinking to myself that maybe I was being too bold, but the moment had taken over.