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My Mom's Best Friend

"Jace wants his mom's best friend. A strange old man has a ring that might help."

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4.2k words 4.2k words

Author's Notes

"This was a fun little idea I had that very quickly turned into a story. As always, thanks for the likes, favorites, and comments!"

“Well, hurry up,” the old man barked as we stood there in the cold, dirty alley. “Are you gonna take it or not?”

I stared at the ring resting in the palm of his outstretched, shriveled-up hand. If what the strange old man had said was true, it would change my life. If it wasn’t, I’d be out $237. Taking a deep breath, I looked the man in his weathered gray eyes before letting out a sigh. Despite my better judgment, I reached out to take the ring and placed it in my front left pocket. Fishing my wallet out of my back pocket, I produced the money he’d requested and placed it into his hand where the ring had lain. The man quickly pocketed the cash, giving me a dark smile.

“Pleasure doin’ business,” he cackled. “Have fun with your new ring, young man.” With that, he turned and walked off. I just stood there, watching him hobble off until he’d rounded the corner and slipped out of sight.

As soon as I lost sight of the man, realization hit me. What had I just done? For a homeless guy, that dude was a master con man who knew exactly how to press my buttons. I let my hormones get the best of me, and now I was broke, with nothing to show for it other than some stupid, tarnished old ring. My face burned red with embarrassment in the cold December air as I trudged back to my car to make my way home.

I’ve had a crush on Kim from the moment I was old enough to notice girls. She’s the living, breathing definition of a walking wet dream. Between her golden blonde hair that always smells like flowers, her ass with its perfect curves, and her absolutely massive tits that she loves showing off, I’m pretty sure there’s not a guy out there who wouldn’t want her.

So why don’t I do something about my feelings? Why don’t I just approach Kim, tell her how I feel, and see how things go? Well, there’s a problem. Kim is my mom’s best friend. They’ve known each other since long before I was born, and they’re so close that I’ve always referred to her as Aunt Kim despite the fact that she and my mom aren’t really related. There’s no way on earth I could ever approach her.

That’s where the creepy homeless guy comes into the picture.

It’s a slow Saturday without much going on, so my mom suggested I get out of the house and knock out my Christmas shopping. I thought that was a fantastic idea, so I grabbed my car keys and headed downtown. After striking out at the first couple of stores I visited, I decided to cut through the alley to the other side of the block.

About halfway down the alley, I couldn’t help but notice a pile of cardboard boxes stacked against one of the alley’s weathered brick walls. Someone had assembled the boxes into a ramshackle shelter, but it did little to protect its inhabitants from the cold air.

Inside the improvised structure, a man was lying down on a pile of newspapers. He was extremely old and haggard, with tattered clothes and a long, unkempt beard that starkly contrasted his bald head. As far as I could tell, he must have lived on the streets for a very long time.

The old man looked up as I passed. For the briefest second, my eyes met his, and I couldn’t help but notice a smile cross his lips. I quickly turned my head down and kept walking down the alley, but my ears picked up a rustling noise, and shortly afterwards I heard a raspy shout from behind me.

The old man exclaimed, "Excuse me, young man!" with all his strength. I found my legs coming to a stop, and I slowly turned to watch the old man ambling down the alley to where I stood. Stopping directly in front of me, the old man started talking once more, the unmistakable smell of alcohol on his breath.

“Young man,” he began, “I was wondering, could you spare a few bucks so I could do some Christmas shopping?”

I scrutinized the man thoroughly. He looked harmless enough, so I grabbed my wallet, pulled out two dollars, and held it out to him while I put it back. “Here you go,” I offered, “Happy Holidays.”

The man looked at the money, then turned his eyes to meet mine. He was doing his best to scowl at me, but something about his expression gave me the impression that he was actually amused.

“Two bucks?” He questioned. “I can’t buy a snow globe for two bucks. Come on, Jace, I’m sure you can do better than that.”

My eyes went wide at his response. “What did you call me?” I asked.

“Jace,” the old man replied, a tone of amusement now seeping into his voice. “That’s your name, ain’t it? Jason Andew Matthews, but your friends all call you Jace. What, you want me to call you Jason or something?”

I stepped backwards. “How, um, how do you know my name?” I asked, my confusion growing.

“Oh, there’s lots I know about ya, Jace,” the homeless man began. “Like, I know how you came down here in that beat-up old Pontiac that you hate, looking to get a little Christmas shopping done. I know how you got $237 in your wallet, mostly tips from that server job of yours at McGinny’s. I even know that you’re turning 19 in February. Oh, and most importantly, I know how you feel ‘bout that Auntie Kim of yours. She’s a real piece of ass, that one. You've got it bad for her, don't you?”

My jaw hung open as I stared at the smirking old man. How could he have known all that, especially the part about Kim? I’d never told another soul about my feelings for her. Despite that, somehow this homeless guy seemed to know everything about me. I was still staring at him like an idiot when he spoke again.

“I know, I know. You want to know how I know what I know. Well, that, young man, is a secret I can’t tell you. But here’s a secret I can tell ya. I got something here that could give ya everything ya want, including that Miss Kim.” As the man spoke, he reached into a tattered pocket, producing a simple, tarnished gold ring, holding it out in front of me.

“You wouldn’t believe it, but this thing is magic. All you gotta do is put it on your finger. When you do, it’ll give you powers. If you ask someone to remember something, they’ll do it, just like you told ‘em. It’s that simple. If you ask your Aunt Kim to remember that she loves bouncing on your cock, you’ll be balls deep in a minute flat. There’s only one limit—it’ll only work on the same person twice in a day. Still, it’ll give ya Godlike power, and it could be all yours for, uh, how about $237?”

The old man watched me closely. I eyed the ring he held out. Could it really do what he claimed? I mean, this guy seemed to know more about me than anyone else. He must have some sort of special ability, right? Maybe the whole homeless thing is just a ruse to get people to lower their guard. At the same time, here he was, asking for all my tip money that was supposed to go toward buying gifts for my family. I couldn’t do that, could I?

“Well, hurry up,” the old man barked as we stood there in the cold, dirty alley. “Are you gonna take it or not?”

And the rest, as they say, is history. I can still hear the old man cackling as he hobbled off, looking like he’d just won the lottery. And more than likely, he did. The more I thought about it, the more I decided that I was swindled. The homeless guy likely saw me at my serving job, which could account for most of the information he knew about me. He probably had some way of figuring out the rest, and the ring was probably something he found somewhere.

I was still burning with shame as I climbed into my car. Part of me just wanted to go home, to tell my mom what an idiot I was, and to see if she’d spot me some money so I could buy gifts for everyone. I knew if I did that, though, I’d never live it down.

Another part of me wondered if there was anything to what the man had said. I fished the ring out of my pocket, looking it over carefully. It really didn’t look like anything special. By outer appearance, it was simply a well-worn gold band. I tried slipping it on my ring finger. Surprisingly, it was a perfect fit. I noticed that I didn’t feel any different after slipping it on, which wasn’t surprising at that point. Clearly, a homeless guy had just conned me.

I was still sitting there inspecting the ring on my finger when my phone started ringing. My mom’s name popped onto the screen. “Hey, kiddo,” came her voice after I’d answered her call. “How’s shopping going?”

“Um, I guess I haven’t found anything yet.” I said, trying to mask my humiliation. “What’s up?”

"Oh, I just got off the phone with Aunt Kim. She said she’s baking some cookies for us. Will you pop by her place on your way home to pick them up?”

“Sure,” I replied. “Anything else?”

“That’s all,” she chirped. “Have fun shopping, Jace. See you in a couple of hours!” With that, my mom ended the call, and I was left alone with my $237 secondhand gold ring.

As I sat there, my thoughts drifted to my Aunt Kim. If the ring really worked… I imagined telling Kim to remember that she was my personal slut. Telling her to forget her husband and remember that she belonged to me. My cock twitched at the idea.

Realizing how stupid I was for even entertaining the thoughts, I started up my car, backing out of the parking spot. I might not be able to control Kim, but I could definitely go see her, I realized. If nothing else, that would serve as fuel for tonight’s jerk-off session. With my money gone, I didn’t really have anything better to do, so I decided to head straight over to her place.

“Mark? Aunt Kim?” I hollered as I opened the front door of their home. “It’s Jace. My mom said you wanted me to pick up some cookies.”

“Hey, Jace!” Aunt Kim’s voice shouted back from the kitchen. “I’m back here!” I followed Kim’s voice to the kitchen, where I found her piling cookies onto a tray.

Kim looked up from her task, smiling brightly at me, and I couldn’t help but smile back as my eyes drank in the vision before me. All I could think as the blood rushed out of my brain was, "Fuck, this woman is gorgeous." She was wearing a pair of tight, weathered jeans, the kind that did nothing to hide the sexy flare of her hips. Along with that, she had on this low-cut beige argyle sweater that hugged her big tits perfectly. It was plainly obvious from her prominent nipples that she’d chosen not to wear a bra today. It took every ounce of my willpower to train my eyes on hers.

“You’re here early,” Kim smiled. “Your mom told me you were going to come by after you finished your Christmas shopping. I figured it would take you a couple of hours.”

“Oh, well, I was in the neighborhood,” I lied, desperately trying not to stare at her tits while doing everything I could to keep my slowly stiffening cock at bay. “I hope it’s okay that I came by a little early.”

“It’s just fine,” she replied reassuringly. “I’m not quite done making all the cookies yet. You’re free to hang out here while I finish, though. Otherwise, you can come back later, too. It’s up to you.”

“I think if it’s alright with you, Aunt Kim,” I began, “I’ll just hang out here.”

Kim’s eyes went back to her work, and I took a seat at the kitchen table, trying not to make it too obvious that I was checking her out as she resumed stacking the completed cookies. We made small talk for a bit while her last batch of cookies baked in the oven.

A timer dinged a few minutes later, signaling the completion of the cookies. Kim grabbed her oven mitt and opened the stove. As she bent down to retrieve the cookie trays, I couldn’t help but stare. Between her shapely ass jutting out and the dangle of her breasts hanging freely in her sweater, I was in heaven. All I wanted to do was get up and take her right there.

It was then that I remembered the ring. My thoughts swirled as I watched my mom’s sexy friend retrieving the cookies from her oven. What if the ring really worked? What if I told Aunt Kim to remember how much she loves fucking me, just as the homeless guy suggested? Could I really take her, right here in the kitchen? The prospect of making her mine was almost irresistible.

Of course, another thought was playing in my head at the same time. What if I tried it, and it didn’t work? The fallout from such a brazen statement would be severe. Kim would probably kill me, and if she didn’t, my mom definitely would. There was still a good chance that the old man was full of shit, and the last thing I needed was to ruin a relationship because I’m a gullible idiot.

Weighing my options, I decided that I needed to test the waters. The old man said I could use the ring two times per person, per day. If I asked Kim to remember something relatively harmless, that would tell me if the ring worked, and then I could still use it again to get what I wanted. That seemed like the safest way to go.

I thought about what I could suggest that wouldn’t be too over the top as Kim set the cookie sheets on the counter and started scooping cookies onto a tray. By the time she was finished transferring the cookies, I’d come up with an idea.

“Well, that’s the last batch. Want to get one while they’re still warm?” Kim smiled and held the tray of cookies out to me.

“That would be great, Aunt Kim. Thanks,” I began, taking a cookie. “By the way, do you remember how you owed me fifty dollars, and you’d pay me back next time you saw me?”

Aunt Kim had never borrowed money from me in my life. Usually, I was the one asking her if she could spot me a few bucks. I fully expected her to ask me what on earth I was talking about. Instead, she tilted her head slightly, taking on a serious expression as her eyes fluttered. As quickly as that moment came, it passed, and Kim’s smile returned.

“Oh, right,” she stated apologetically. “How could I have let that slip my mind? Hang tight, kiddo. My purse is in the other room. I’ll be right back.”

I watched in shock as Kim put the cookie tray down and strutted off toward the living room in search of her purse. I held up my hand and stared at the ring in disbelief. I couldn’t believe it, but the ring did exactly what the old man said it did. This was incredible. My mind spun with the possibilities. I’d have to be careful so I didn’t get caught, but if I played my cards right, this thing could open the doors to anything I wanted. Anything, I realized as a grin spread across my face, including Aunt Kim.

I was busily planning out how to make the best use of the ring when Kim returned, fifty dollars in hand. I looked up at her, smiling broadly as she handed me the bills.

“There you go, Jace, fifty dollars. Thanks for loaning it to me!”

“No problem, Aunt Kim,” I replied, standing up to face her as I slipped the cash in my pocket. I’d worked out my plan, but first, I needed to make sure the coast was clear. “By the way, where’s Mark today?”

“Oh, he got called into work for an emergency. He’ll probably be gone for a couple of hours.”

Perfect. I found myself looking Kim up and down briefly before my eyes met hers. I was really going to do this. My heart was racing, desperately hoping that the first time wasn't a fluke, as the words began to form in my throat.

“That’s good,” I grinned wickedly, “because there’s something else you’re forgetting.”

“Oh, what’s that?” Kim asked, a slight tone of concern in her voice as she took a half step backward. I took a deep breath. This was it.

“Well, Aunt Kim, surely you remember that you’re a totally depraved slut for me, a sexual plaything who loves doing any dirty thing I ask of her?”

As I spoke, Kim’s eyes went wide with shock. At first she looked almost as if she was going to say something, to scold me for my illicit suggestion. But then, her face went slack and her eyes fluttered just as they had the first time. I watched for several seconds while she remained in this state. Finally, her eyes came back into focus, meeting mine as a devilish grin formed on her lips.

“Oh, Jace,” she purred in a sexy tone I’d never heard from her before as she brought her hand up to cradle my face. “How could I possibly forget how much fun we have together? You always get me so wet with the dirty little things you make me do. Now, should I box up those cookies for your mom, or was there something else you wanted to do first?”

It...

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