Note : this is a sequel to “Helping Out a Barista”, and builds on the characters and scenario there.

Also this story has a bit of a dominant / cruel female with humiliation and findom (nothing too extreme) so if that’s not your thing maybe move on; if I write a third chapter I’ll make it more traditional again.

———————

After my tryst with Kristina, I followed through on my promise and paid to have her car fixed. Easiest money I ever spent. I felt 20 years younger, and every time I even looked at my hot tub I got at least a semi thinking about that stacked 20-year old with her legs wrapped around me.

It had been about a week, and I had been busy as hell so I hadn’t been by the coffee shop at all, but Kristina had shown up as promised to deal with the dogs and do numerous chores for some extra money. She was friendly with me, but there was no hint that there would be an encore to our hot tub shenanigans now that she had her car fixed and didn’t need anything from me (at least, nothing she couldn’t get by just playing with my dogs for 10 minutes a day) But I didn’t mind, the money was nothing and even if she wasn’t flirting with me she was still a beautiful 20-year old hanging out at my otherwise empty house, refreshing the details for the glorious mental video that played in my head pretty much 24/7.

A couple of weeks later things finally slowed down for me and I got back into my old routine, including going by Kristina’s coffee shop. She wasn’t there when I walked in, but one of the girls said “Heyyy Miiike” in a weird way when I walked in, so I’m guessing she told them SOMETHING. I mean, I know girls talk and the younger generations were getting more and more open with their sexuality, but I just couldn’t imagine a 20-year old girl telling her friends that she fucked a 40-year old nerdy customer for a couple grand to fix her car. But as I watched a few of the girls talking conspiratorially and trying to suppress their giggles, I was finding it harder to believe that Kristina HADN’T told them everything.

Not that I was complaining. I wondered it was a pretty big feather in my cap.

I ordered my coffee and stood off to the side waiting. The girls had already forgotten about me and moved on, which was just as well. Although one girl, Carly, was standing at the counter staring at me. Carly was one of the more interesting girls working at the shop. She had the body and face of a perky school sorority girl, but the demeanor of someone who was confident she could snap you in half if she wanted to. She rarely said much to me but when she did she all the time had that confident undertone that was just so rare to see and hear in a younger person.

Being the letch I am, I found her irresistible, if a little scary.

“Hey Mike.” I guess today would be one of the days she acknowledged my existence. She spoke loud enough for anyone to hear, without a care in the world who was listening. ” I heard you, uh, helped Katrina out.” She smirked and glanced at my crotch before glancing back up at me. That pretty much confirmed my suspicions.

“We came to mutually beneficial business arrangement, yeah” I replied, trying to sound like it wasn’t the greatest night of my life as a man.

She rolled her eyes, seeing through my casual bravado in an instant. “I’m sure you did, Casanova. Look, I just spent every dime I have on fucking tuition, and I’m a month behind on my rent. I was hoping you could help me out.”

“Uh, sure, what did you have in mind? Because Kristina is already doing stuff around the house and taking care of my dogs, I’m not sure what I can offer you.” I of course knew exactly what I could offer her, but I didn’t want to be the first one to say it.

She scoffed right in my face. “Mike, have you looked in a fucking mirror in the last five years? You think having a couple bucks in your pocket and using it to get some desperate bimbo to spread her legs for you makes you God’s gift?”

My own confidence deflated quickly. I wasn’t used to really having confidence with women so as soon as she went on the offensive I quickly reverted to feeling like a 10th grader. “No, no no Carly, not that at all, I wasn’t trying to insinuate.. um…. you know, I just… “

She smirked at my discomfort. “Look. I’ll make it simple for you. I’ll give you the same deal Kristina did, minus the bonus she decided to give out like a desperate slut. You can touch me anywhere you want, hands only. Except for me it’s $5000. Have the cash at your house tonight and I’ll see you at 8.” Then she just walked away.

What the fuck? I gave Kristina like 1800 bucks and she let me fuck her. Raw, no less. Where the fuck does this bitch get off thinking I’ll give her five grand to grab a boob? I just laughed to myself and shook my head as I picked up my coffee and left. Five grand. Pff.

—

After lunch I was still thinking about Carly and her “offer.” Where does she get off? I mean… sure, I’d love to just SEE her tight body in front of me, let alone be able to touch it. Where Kristina was more of a voluptuous goddess, Carly had the type of body I discover it hard to describe without sounding extra weird. Nubile? Gross…. but accurate. I was a boob guy, and she couldn’t have more than a large B, but on her tiny frame they were truly perfectly proportioned. No matter the season she would all the time have on either pants or shorts that weren’t, like, scandalous or slutty but still managed to mold to her tight young body, leaving so little to the imagination but at the same time so, so much.

But really her most striking feature when you saw her in person were her eyes. They just seemed to look directly through your skull. It’s odd to give too much power to someone’s eyes but she really did give the impression that she was five steps ahead of you intellectually. And from me that’s saying something, because while I was all the time shy around women, I at least all the time felt like I could keep up with most people in the brains department. But it’s not like she was gonna try and best me as a Mathlete, it was more a cunning intelligence. She knew what you were gonna say or do before you did, and knew exactly how she would respond to get her way. It was unnerving.

I snapped out of my daydreaming about Carly to realize I had unconsciously been driving towards my bank. My subconscious had just been spending the entire morning convincing me that five grand was nothing, girls on OnlyFans make like 50 grand a month or something, and they’re just showing off for the camera. Some vixen wants to show off to me in PERSON and all it’ll cost me is 5k?

FIve grand isn’t exactly nothing. I’d been strutting my stuff like I was unimaginably wealthy, but in reality I was just “comfortable.” And some renovations on my house had really run over, and the contractor agreed to give me a deal if I paid the overrun in cash. I was at the bank to get 40 grand — honestly that was pretty close to draining the last of my cash savings. And now I was gonna get an extra 5k for Carly? And I was gonna get another 5k on top of that in case any of the home improvement costs bumped up even more, so this 50k was literally all I had that wasn’t tied up in investments. I need to stop throwing money around every time some young girl flashed her tits at me. And yet….

The teller was a little argumentative at first, saying they don’t like to give that much cash out, was I sure I didn’t want a bank check instead, it would be safer. But eventually they relented and started counting out 100s.

‘Five grand is nothing’ I wondered as the piles stacked up.

———-

It was 8:41 and I had basically decided that Carly was gonna stand me up. I laughed at myself for even thinking she wasn’t fucking with me in the first place. Probably just wanted to see if I would really pay five THOUSAND dollars to just touch her. I was disappointed, but also relieved, having that money in my profile would give me a bit of a cushion back.

I was resigned to watch an hour of TV or so and go to bed early when I heard a car pull up my drive. Son of a bitch, was she really here?

I watched through the front window of my house as she hopped out of her small SUV and walked up to my front door. She had barely finished her second knock when I reached the door and opened it for her. She just smirked as she walked by me, just knowing that I had been waiting for her, and that she had given me the maximum amount of anxiety about it.

“Cool place.” She threw her bag on my kitchen island and looked around. “I guess you really are loaded.”

I just shrugged. “I guess.”

She was dressed casually. A pair of “nicer” yoga pants (hugging to her legs and tight ass as usual), and a looser top that while she stood there just hung maybe an inch above the waist of her pants, just giving the smallest glimpse of her tight midriff peaking out from underneath. It was one of those shirts where if she raised her hands over her head the bottoms of her breasts would probably JUST be–

“You got anything to drink? I like bourbon.” I looked at her dumbly; I think I had been just staring at her navel for the past 30 seconds, lost in wondered. “Rocks, please.”

Right.

“Sure thing.” I made her a glass of one of my nicer bourbons, and one for myself, and gestured to the couch. She sat right in the middle, leaned back, and put her feet — still wearing her sneakers — right up on my coffee table as she took a sip of her glass.

“Look, Mike, it’s not that I don’t trust you or anything, but if we’re gonna do this I’m gonna need to see some cash up front.” She seemed almost bored by this whole thing. I was sort of hoping for some sort of seductive routine if she really wanted me to pay her this much cash. But at the same time I almost spilled my drink jumping up to go open my safe and get a pile of cash for her.

I was back a minute later and handed her an envelope of fresh 100’s adding up to five grand. She grabbed it and just sort of sat there looking at it, seeming contemplative but in retrospect I’m sure she basically had this scripted before she walked in the door, and was just toying with me for her own enjoyment. Lazily flipping through the stack of hundreds, taking an occasional sip of scotch, not saying a word to me.

Finally, after what felt like 10 minutes of awkward silence and me standing in front of her, she spoke. “It doesn’t look like that much, does it?”

“What’s that?”

“I dunno, I just thought, five THOUSAND dollars, it would look like this huge stack of money.” She shrugged and just sort of tossed it apart like it was nothing. I was giving her thousands of dollars for almost nothing in return and suddenly I was the one that felt cheap.

“I… I could get it in 20’s if you want to feel a larger stack or something?” Why was I offering to do things for her, she had literally given me nothing and didn’t seem like she was gonna any time soon.

She rolled her eyes at me. “It’s fine. Did you want to do this here then?” Her complete disinterest in this whole thing was sort of killing it for me. With Kristina, I was under no illusion that she was with me for anything but my money, but at least she was nervous and excited by the whole thing. Hell, she got so excited that she actually let me fuck her when all I paid for was access to be able to touch and kiss her body. For less than half what I was paying Carly here….

I again realized I had been in my own head for a few seconds when she stood up in front of me, grabbed my chin and pointed my face right at hers. Those eyes suddenly took on a mischievous depth. “Maybe you should start.” Her voice was quiet and soft, but she wasn’t asking.

Finally, I wondered, and reached out to the bottom of her shirt. She slapped my hand away. “Not on me. You start on you.” And she sat back down and crossed her legs, and crossed her arms across her chest, never taking her eyes off mine.

“You want… me to get undressed?”

“It only seems fair.” I mean, I guess it was only fair, if she had to be so did I? I mean, I was paying for this, but I didn’t want her to feel uncomfortable.

She sat there as if she had at all times in the world as I dumbly convinced myself to obey her, and took off my shirt. I had gotten a little pudgy as I entered my 40’s, and hadn’t been to the gym since… well, ever, really. Does high college gym class count? I saw the slightest hint of a smile in the corner of her mouth as I threw my shirt to the side, and then she nodded her head down, silently telling me to keep going.

I had been walking around the house with a raging hard-on for the past two hours, but the awkwardness I had been feeling for the last several minutes had had the opposite effect. My dick felt like it was trying to crawl back inside me, as if the room were ice cold. I unbuckled my belt and slid my jeans down, awkwardly realizing as they hit my ankles that I still had my shoes on. So I spent the next 30 seconds awkwardly trying to kick my shoes off, with my jeans around my ankles and my boxer briefs the only thing saving me from the humiliation of my shriveled shy cock. I heard Carly audibly laugh at me as I finally kicked my pants apart, my socks still on. I had never felt more vulnerable in my life. It didn’t make sense. I outweighed this girl by 50 pounds, we were in MY house, I was the one paying… and yet there was no doubt she was completely in charge.

“That’s it?” she asked, leaning forward. I dreaded that she was gonna tell me to strip off my underwear. I just knew I was not at my best by any stretch. I’m more of a grower than a shower anyway — a perfectly average cock on any day, thank you very much — but right now what I was showing would be utterly humiliating. Luckily she just shrugged. “Fair enough.”

She put her drink down, and stood up, standing just a few inches in front of where I was standing, her eyes never leaving mine. She yawned, slowly stretching her hands up above her head, and I could see her little shirt rise up, just as I had imagined it when she first walked in. Her belly button showed itself, just as cute and tight and perfect as the rest of her body, and then more of her almost impossibly smooth belly. Her hands clasped together over her head as she reached up even higher, exaggerating her yawn as I watched the slightest hint of the bottom of a breast show under her shirt. It instantly became apparent she wasn’t wearing a bra, that shirt floating over her torso the only thing keeping me from seeing her completely topless mere inches in front of me.

I finally felt my cock stir, my arousal finally overcoming my awkwardness and embarrassment. Her smell — just a slight whiff of a shampoo from her hair, but undoubtedly feminine — hit my nose and my excitement spiked. I remembered why we were here, and what I was paying for. Not only would I be seeing her, I’d be touching her, all of her. I started to smile. She lowered her arms and put a finger on my chest, our first physical contact… well, ever. She stroked her finger through my light chest hair, and looked down at my crotch, which was at probably half mast by now and growing quickly. “Good to see you have something going on down there, I was worried you were tucking it or something.” Her cruelty made my erection hesitate, but her closeness and her finger still on my chest won out. “Let’s see what you got going on then.” She stepped back, grabbed my underwear, and just pulled them to the floor as if she were pantsing me for a prank. Not a slow, erotic undressing but a shocking reveal. I didn’t feel like I was being seduced but rather exposed and toyed with. I had instant flashbacks of bullies in middle college gym — almost 30 years ago! — and the blood instantly drained from my modest manhood. You could visibly see it deflate. She held her hand to her mouth to stifle the giggle. “OK then” was all she said, stepping back and taking in my entire body, which must have looked so pathetic at that moment that I honestly couldn’t imagine anyone ever fucking me again. How had this night gone this badly already? How had I already paid for what was already the most humiliating experience I could remember, and it had literally been like 15 minutes.

“Look, if you’re not into this” — she gestured over her body — “it’s fine, I won’t judge.” She then stared at me as if I were some kind of child, obviously expecting a response.

“No, it’s not that, I’m just… shy, and expected to see you naked, not just be standing here….” I trailed off.

“Oh so it’s OK for you to just invite some young girl to your house and expect her to be naked but not you? Kind of creepy, Mike.”

Obviously the first wondered that came to my mind was “but I’m PAYING you!” but saying that out loud somehow felt MORE pathetic so I just stood there silently with my head down.

“Yeah, I just don’t know Mike, I don’t think I feel comfortable here right now. I… I think I’m gonna go.” She grabbed the envelope of money and her purse and turned towards the door.

“Wait, Carly.” I was still fully nude, standing in the middle of my living room, as she walked away from me. “I… I have a little more money… I’d love it if you stayed… and we could do what we had planned?”

She stopped. Without turning around she said “and what had we planned?” I could hear the cruel smile in her voice. She wanted me to say it out loud, standing here at my most vulnerable.

“That I’d… that I’d get to see you naked. And touch you.” That sounded so weak, and lame. I literally sounded like a child.

“Touch me? I don’t remember agreeing to that.” I could see her holding the envelope filled with hundreds that i had already given her. Her hand was loosely gripping it, hanging to her side, the swell of her ass standing proudly next to it. “But for another 5k I’ll take my top off for you.” She still hadn’t even looked at me.

“Deal.” WHY was I still negotiating?? I’d somehow doubled what I was paying her for less than half the reward. I quickly turned and shuffled back to my bedroom where the safe was. I keyed in the combo and as I opened the safe door I saw a shadow fall over me. Carly had followed me into my bedroom and was watching over my shoulder.

“You holding out on me Mikey?” No one had called me that since I was a kid.

“Holding out?” I asked stupidly.

“I see a lot more than five grand in there.”

“Oh, well, yeah, I mean, I took a bunch of my savings out in cash to pay some contractors….” Why was I even telling her this, like it was any of her company?

Her hand suddenly reached out and touched my hip and she stepped closer behind me. “Contractors?” she almost whispered, her mouth right next to my ear.

Her hand on my hip was now slowly rubbing forward. Inching closer to my cock, which had again reversed course and was quickly starting to stand at attention. She whispered again “because if you don’t have any plans for it, tonight seems as good a night as any to spend some of it.” Her finger just barely grazed my pubic hair, and I felt myself nodding along, grabbing another $5000 bundle along with the one I had already agreed to give her. Her hand retreated back a bit as she leaned forward, leaning fully against my back as her other hand reached into the safe next to mine. My thoughts were on the feeling of her breasts, still only covered by the thin fabric of her shirt, squishing into my back as my eyes watched her grab the remaining several bundles of bills and drop them into my hand. She kissed me on the cheek as she stood back away from me, lightly grabbing me by the arm and turning me around to face her.

She finally had the seductive smile on her face that I had been craving at the start of the night. I stood there naked in front of her, fully erect and at attention, holding 45 grand in my hands as if it were completely ordinary. My safe, empty apart from my passport, hung open behind me. Carly’s hands crossed in front of her and grabbed the bottom of her shirt, and she slowly pulled it up her torso, pausing as the bottom of her breasts again came into view. I briefly feared she was just fucking with me again, but she finally continued and pulled the shirt completely off, dropping it behind her on the bed. She reached her hands over her head, closed her eyes, and just swayed for a moment, letting me take in her topless body standing in front of me. Everything I could see seemed like it was Photoshopped. Her skin was smoother than I wondered skin could be in real life, without a trace of imperfection. Following the contour of her body from her hips, she truly had an hourglass shape, her taut stomach shrinking in and then growing again to her perfectly proportional breasts, which almost seemed to be floating off of her body. Her nipples just slightly erect, her body continuing to undulate in front of me, and all I could do was stare.