Category: Mature Stories

Teardrop Tonya

by SecondCircle©

I had been best friends with Mark all of my life. So when he asked me to house sit for him it was a no brainer. He would be out of town for two weeks on vacation with his family and wanted me to stay at his house, feed the fish, keep his pool clean, keep his two dogs fed, mow his yard... basically live in his house and keep it up for the time that they were away. He'd been planning this trip to Florida with his wife and two kids for a long time, and I didn't wanna leave him high and dry.

Not that I needed any convincing to do this for him. I lived by myself in a small one bedroom apartment and worked nights usually. Whatever time I didn't spend at my place playing video games I spent at Mark's house anyway. Mark always laughed at me and told me I needed to get out more and meet people, but I never met a girl that didn't end up being a bitch in the end anyway, and I wasn't looking for much more than the occasional one night fling with someone anyway. Besides I wasn't much of a lady's man. I was skinny, and kept myself well groomed, but I was a bit shy and nervous as hell around women, even unattractive women.

I decided to take time off from work and just chill out at Mark's house. I asked off for the first week that he would be gone, and decided to stay at his place for that week. He told me that I could have their guest bedroom to myself and do whatever I wanted as long as I didn't go into their bedroom or mess anything up in the house. I assured him that I wouldn't have any friends over or girls or anything like that. In the heat of the summertime, I was more interested in swimming in his pool than anything else.

I saw them off the Monday they left, with Mark's wife Debbie frantically dashing through the house getting last minute items to pack while Mark made sure I had all of the emergency contact numbers and such. We were standing in the driveway watching Debbie get their kids situated in their SUV when we spotted Mark's neighbor across the street walking down her concrete driveway to check the mail.

I felt Mark nudge me on the arm and nod his head towards his neighbor, though I had already spotted her.

"Check it out Todd," he said. "There's Teardrop Tonya."

I smiled and nodded. Tonya had lived across the way as long as Mark had lived in this house. She had been the center of many of our conversations in the past. Even the teenagers that lived on this street swapped stories about her. The women of the neighborhood, including Mark's wife, would sneer anytime they saw her, and would gossip and spread nasty rumors about her. They made sure that she was out of earshot when they talked, however, for none of the suburban housewives wanted any sort of altercation with her.

We both watched as she strutted down her driveway. Tonya was an older woman, somewhere in her mid forties. She had quite the reputation with the locals, due to her wild and troubled history. We knew that she had been a young bartender at one time, working at a rowdy bar on the outskirts of town. She married the owner, who owned several such establishments, when she was in her twenties. The owner was about fifty years old or so. They had two children that few have ever seen before.

To hear Mark tell it, things went well for them for a couple years, but Tonya played him like a fiddle apparently. He had bought her the house and a flashy new car, giving her everything she could ever want, until they had a huge falling out. She divorced the guy and kept everything he had given her, and probably much more. The guy had taken the kids with him and moved out of state.

Tonya quit her job at the bar then, and almost immediately began seeing and old Vietnam war vet that rode a motorcycle, and dressed in denim vests and had tattoos and such. This new man, another cradle robber, married Tonya and lived with her for several years. They were supposedly real wild together, a really great couple when they got along, but screaming at each other in the yard and fighting each other constantly.

Her new husband was notorious for doing lots of illegal stuff, from drugs to stealing cars. His friend was said to have owned a body shop that was actually a front for a chop shop that would disassemble cars and build new ones illegally. He eventually was caught, and is still currently serving time in the penitentiary. True to her style, Tonya divorced him shortly after his incarceration, even getting to keep the guy's motorcycle.

By this time Tonya was in her thirties, and according to the soccer moms of the neighborhood, sleeping with numerous men, all wealthy, married, and in one way or another, powerful figures. When she overheard that one women had been spreading these rumors around, she ran into her at a supermarket and assaulted her, beating her senseless. She served a little bit of time for that.

When she got out of jail, Tonya once again married, this time to a really wealthy elderly man. He was smitten with her, and to hear it told, she changed her life around after they got together. She started going to a local church (the same one that Mark and Debbie still attend), and occasionally, one could spot her now fully grown sons coming to town for a visit. It wasn't long before the Tonya's elderly husband died of a heart attack, and everything he had began to fill her coffers even more.

And there she was now.

"Damn man, she wears that shit on purpose, you know?" Mark said, shaking his head.

Tonya definitely stood out here in the suburbs. She was tall, maybe five foot ten when she wasn't wearing the leather heels she loved so much. She had very long and very full jet black hair, which she would always fix a different way or touch up with different colors. Today it was blonde streaks that patterned her dark hair. She always wore large earings, her favorite seeming to be ones that had feathers in them. Tonya had large dark brown eyes that seemingly always were bordered with great looking makeup, the kind that Debbie said was too slutty for a woman her age.

Tonya earned the name "Teardrop Tonya" because of her tattoos. Supposedly, she got them when she was married to the war vet. Her right arm was a full sleeve, depicting a feminine skull wearing a Native American headdress that flowed down to her elbow. From its hollow eyes, large highly detailed trails of tears ran down Tonya's arm. It was the only tattoo large enough for me to make out from a distance, the rest were just a jumble of colorful pictures and stars. Her left arm was tattooed as well though not quite as much. There was an obnoxious guy that Mark knew, who claimed to have slept with Tonya, that said she had tattoos of all of her ex husbands' names in a list somewhere in her sleeve.

The woman's tits were amazing, and were the cause of a lot of jealous talk from most of the other women that lived here. Tonya's tits were almost unbelievably large, and it was rumored that they were either bought for her by her first husband or medically enhanced. When I first saw her, I thought maybe it was some sort of special bra she might have worn, but after seeing her in a bikini top one time I knew this wasn't the case. Today she was wearing a strapless top, her cleavage exposed to the hot sun. Tonya also had on a pair of cutoff blue jeans that stopped at her upper thighs, displaying her long well tanned legs.

"Damn, Todd, that woman ages well," Mark stated as he watched her.

Tonya retrieved her mail, and after briefly looking it over, gave a glance our way. I pretended to watch Debbie at that moment, and noticed Mark use the same tactic. Debbie looked up then and asked Mark if he was all set. She glanced over in Tonya's direction, and made sure to turn around before rolling her eyes with a disgusted look on her face. I couldn't help but watch Tonya stroll back up to her front porch, her hips swaying seductively as those long legs climbed her steps.

Mark and Debbie left a few moments later, with kids yelling and laughing in the back seat as they waved goodbye. The rest of the day was pretty uneventful. I took a dip in Mark's pool and cleaned it out for most of the evening. I made myself something to eat and eventually crashed out on the sofa watching movies that night. The week pretty much dragged on like that, with me swimming and playing online games on Mark's 72" flat screen.

Mark had no shortage of cool stuff to do. With his wife working at the hospital and him raking in money as an accountant downtown, they lived pretty comfortable. I had always been quite the opposite, working the graveyard shift at the local industrial park and keeping to myself. I made enough to get by, but usually when it cane time to have real fun I was hanging with Mark. I even felt a dirty temptation itching within me, and discovered Mark's personal little porn collection in his closet and watched several discs on his enormous TV.

Thursday rolled around and I noticed the yard was in need of a trimming. I fired up the mower in their garage and got to work. I wanted to wait until late in the evening to mow but Mark had a pretty sizeable acre and a half that would take several hours to finish. I threw on my swimming trunks and a tank top and started on the backyard. Just as I thought, the July sun had me burning hot and dripping with sweat by the time I finished the back. I cut the mower off and took a quick dip in the pool before going inside to grab a bite to eat.

After I took my break, I began mowing the front yard. The heat was still intense, and I cranked the mower into high gear trying to finish as fast as possible.

Until I saw Tonya, that is.

I spotted the sultry older woman walking from around her house to her front porch, carrying two potted flower plants. Today she was wearing a tight grey tanktop that again showcased those enormous tits. She had on her favorite shorts again, those cutoff jeans that were frayed at the ends. Her long black hair was tied up behind her head at the moment. She must have had on ten different bracelets on her tattooed arms, and had adorned her ears with black and white feather earrings.

Immediately upon seeing Tonya, I dropped the mower into a slower gear, and adjusted my sunglasses to make sure she couldn't see me looking. But I was looking. Tonya's back was to me when she set the two plants in the grass in front of her porch and squatted down to mess with them. Debbie had always talked about how Tonya wore clothes that were made for younger girls or styles that didn't fit her age. Her grey tank slid up her back, exposing more tan tattooed skin. I couldn't make out the markings from this distance, the sight of the flesh was enough.

I had to remember to turn the mower before I drove over Mark's driveway. As I made another long pass across his yard, I tried not to appear too obvious as I continued to glance Tonya's way. She was standing now, but bent over the pots, the bottoms of her dark ass cheeks showing as her tight shorts wedged up in between them. She stood and circled back around the house.

The next time she came around she was carrying two more plants. This time, as almost an answer to my prayers, Tonya was leaned over facing my direction, sticking flowers in the pots and watering them. I could see from a distance the dark slit of her cleavage and the round tops of her breasts wobbling as she worked. I realized my dick was pushing into the waistband of my trunks. I adjusted myself to a more comfortable position, glancing back to see Tonya looking up at me.

I tried to act normal and continue my mowing pattern, but I had butterflies inside, worried she might have seen me repositioning my boner. After a few minutes when I turned the mower heading towards her house, and saw Tonya disappear around to her back yard. She returned again with two more plants, and this time I tried to keep my eyes averted.

After another half hour or so at about midday, I finished mowing the front yard. I pulled the mower back into the garage and walked back outside, wiping the sweat from my brow with my shirt. The sun beamed down relentlessly, and I was glad to be done with the yard. That's when I saw Tonya standing about midway in her front yard looking directly towards me. She had one hand on her hip and another shielding her eyes from the sun.

"Hey, excuse me!" She called over.

I almost froze where I was at the sound of her voice.

"Uh, hey!" I shouted in return nervously.

In the same pose, she yelled, "Could you lend a girl a hand for a minute?" It was almost spoken like a demand.

My chest went cold as I stammered out a reply. "Y-yeah, sure."

Tonya didn't wait to see if I was coming. She turned and began strutting back towards her porch. Almost in a trance, I headed in her direction. Absolute nervousness overwhelmed me then, enough to almost make me bolt back into Mark's house. I had to try to play this cool. I had to calm down.

I made my way across the street and into her yard. The trip to her porch gave me a feeling akin to meeting a famous celebrity. I would finally see her up close. It was exciting and terrifying at the same time. I just knew I'd come off as a dork, but I tried to act as normal as I could.

Tonya looked amazing. The first thing I noticed safely from behind my sunglasses were those huge tits. The tan skin of her cleavage was riddled with small freckling age spots, but somehow seemed to add to their appeal. The skin at the top of her cleavage had begun to draw subtle lines, but wasn't at all repulsing. I realized that she wasnt wearing a bra. The sight made my dick stir in my trunks as i could see the natural droop of her bra-less chest, as well as the shape of what i thought were her nipples through the thin grey fabric of her tank top.

Her tight angular face was showing the same barely noticeable signs of age that were expected of a woman in her forties, with small tired looking bags beginning to form under her eyes and crow's feet at their corners. Her full lips had the slightest lines in them, and her mouth in general looked as though Tonya had worn a frown her whole life. She carried a small tummy on her midsection, but not big enough to make her look unsightly.

Overall, Tonya had the slightest bit of age on her, but she looked like a goddess. There was a tired look about her, bit she also had an air of superior sexiness and confidence. I had heard the words "cougar" and "milf" thrown around alot, but there simply was no way to describe this woman. Tonya was simply a bad ass mature woman that could still show her stuff.

As I came up to the porch, Tonya was lighting a cigarette. As she inhaled the first drag, she reached behind her and let her hair fall down her shoulders. Her piercing dark eyes were fixed on me, and made me a nervous wreck inside.

"What's your name, kid?" She asked, letting out a long plume of smoke.

"Todd," I managed to say without stuttering.

"Well, nice to meet 'cha, Todd." Tonya's voice was a low tone and smooth as caramel. "You think you could put these up for me?"

At first I was unsure of what she meant. Of course my eyes were darting repeatedly to her breasts, so that my first thought was sexual. I then saw the potted plants sitting on her porch behind the wood railing. I looked and saw the hooks above each one across her porch, which was a rather tall porch.

I nodded and said, "Oh, yeah, if course."

I had to walk over and come up the steps to begin. I could feel her watching me, standing there smoking with one hand on her hip. I focused and went to hang the first pot furthest away from her.

"You holdin' the fort down hun?" I heard her say.

"Uh, yeah. My buddy Mark and his family are on vacation. He asked me to look over everything."

Tonya gave a slight smirk as she blew out smoke. "Pretty good at that, huh."

I didn't know what to say back to that so I simply hung the pot and went on to the next one, but I didn't miss that slight pun about looking that she had added.

"Uh, sorry Ma'am, what did you say your name was?" I asked.

Tonya shot me a look and a roll of her eyes. "I'm sure you might have heard it by now. And don't call me Ma'am. I ain't that old honey."

I hung another pot and continued to the next. "It's Tonya, right?"

She sat in the rocking chair next to her and flicked her ashes beside her in a tray on a round patio table.

"That's right," she said sounding slightly amused.

I decided maybe not talking would be better as I hung another plant. She sat staring off on the distance as she smoked and I finished hanging the last plants. I was close enough to smell her strong cherry fragrance, and I could make out alot of her tattoos now. Most were Indian related, a wolf howling or a dreamcatcher that had a skull design in the web. They looked great on her tan skin.

"You look like you've been swimming, Todd," Tonya noted.

"Oh, yeah. Mark has a pool."

"Be nice to swim in this kinda heat," she said.

Thinking quickly, I said, "Well, you could come over and take a dip if you wanted sometime."

Tonya smothered her cigarette out in the ashtray on the table. She gave a small alluring smile. "That'd be nice. Of course, if his little twat ever found out she'd shit."

I was a little surprised. I had never heard a woman speak so bluntly before. "Debbie?" I said trying to sound skeptical.

"Yeah." Tonya gave me a look as I hung another pot. "Don't think I don't know that these little cunts whisper behind my back. I don't mind, but that doesn't mean I'm an idiot."

I gave a little laugh. "Uh, yeah, I guess they do talk."

I hung the last plant and Tonya waved me over to the chair beside her. "Come over here and stay a while, Todd."

My heart skipped a beat in my chest. She was asking me to stay. This was a moment I had fantasized about many times, to sit with the lovely and fierce Teardrop Tonya. Not wanting to seem rude, I took a seat in the chair beside her. The close proximity made the hairs on my arms and neck stand, even in this heat. Tonya was reaching behind her, and I realized she had a cooler there. She then produced two bottled beers. Tonya held one out for me, and I felt obligated to take it. She popped the top to her own and took a long, deep swig. I followed suit, trying to play it as cool as I could.

"So, what do they say about me nowadays?" Tonya asked me.

I licked my lips and shrugged, unsure of how I should handle this.

"Well, you could kinda guess what the women are saying."

She shook her head and her lips became a thin line. "Those little bitches will always talk. What can you do? I try to be friendly with them and all I can smell is jealousy and bigotry on them. They'll smile and act sweet and prissy to your face but as soon as you turn your back..."

Tonya took another swig of beer.

"What else do people say, Todd?" She said suddenly, locking her dark eyes on mine.

I shrugged. "They, uh... well, they call you a gold digger." I couldn't believe what I was telling her.

Her brow furrowed. "What?"

"I-I mean you have been married to all older men, that w-were pretty wealthy...."

Tonya studied me a moment with such a look I thought she might crack that beer bottle over my head.

"Is that not the same reason little miss sweet bush married your accountant buddy? And the reason I don't see you with a plus one? Nobody wants someone that ain't got the money, sweetheart."

Tonya's words hit home and stung a little. I had to give it to her though. No one was interested in a factory working shut in that played too many video games.

"So yeah," Tonya shrugged, "I guess I am a gold digger. It's got me what I have now, so fuck 'em."

She lit another cigarette and crossed her tan legs, which drew my attention to them. I couldn't help but picture them wrapped around my waist.

Category: Mature Stories