A Helping Hand

Here's how I imagine things played out from Candi’s perspective. She enjoyed a few more days of normal college life, and then received a distressing call from home. While leaving the store one night, her mother had been the victim of a violent mugging. The three perpetrators broke both her arms, used her debit card to empty her bank account, and raped her repeatedly before fleeing. For the record, I only paid for the broken arms and the theft. Candi must have gotten her looks from Mom, because apparently they just couldn't help themselves. Not that I was complaining.

With her mother unable to work, her family was in dire straits, and Candi wasn’t the kind of girl who could just leave them to fend for themselves. She applied for some jobs, but was uniformly turned down. At some point, she realized something was off, maybe noticed a sly glance from a prospective employer, and tried looking up her own name.

I'm no expert at webpages, but they mostly make themselves at this point. Any search of Candi’s real name would bring up a bright, colorful site all about “the new best stripper in the world! <3”. Her dancing looked much less stilted as a series of still photos, and I'd even been lucky enough to capture that bare chest with a good shot. All it took after that was just a touch of Photoshop to put some smiles on her face, and voila.

This wasn't an insurmountable problem, of course. I'm sure Candi knew she could contact the hosting site and convince them to take the site down. She also knew there were people out there who wouldn't turn down a potential employee over some lewd pictures. But these were solutions that required time, and poor Candi didn't have much of that at all.

She knew of one place that would still hire her, though. And I was there waiting when Candi made her encore at the club.

She actually did better this time. It was still pretty awful, but need is always a good motivator. She even managed a few tips from some generous patrons. But not much, and not enough.

I was already waiting for her at the bus stop this time. From her grimace, and the distance she stayed at, she definitely remembered me. I just gave her a friendly smile and patted the empty spot next to me on the bench. She didn't sit, but she reluctantly moved a few steps closer. “Not the most well paying job,” I observed neutrally. She barked a short humorless laugh.

“And you'd pay me so much better?” she asked wryly.

“Of course,” I told her.

She sighed, and then looked at me squarely for the first time. “I told you before, I'm not a whore.” She waved her hand in the direction of the club. “If you’re really looking to dish out money, I’m sure there are plenty of women over there who would be happy to show you a good time. So please just go talk to them and leave me alone. I’m tired and I’m hungry and I really don’t want to deal with this right now.”

“There's that word again. It's not entirely accurate, you know. If you were a prostitute, you would be sleeping with multiple men for money. That's not what I'm proposing at all.”

“So you're not trying to convince me to have sex for money?” she asked skeptically.

“Well, yes,” I admitted. “But not with multiple men. Just with me.”

Candi is a kind girl at heart, so she tried not to show just how revolting she found me. It was a familiar reaction, and not unjustified. I’m a lot closer to my fifties than my thirties, carrying around a couple hundred extra pounds, and the nicest thing I can say about my face is that it’s got all the usual pieces and in roughly the right spots. I’m not anyone’s Prince Charming.

I could see her trying to come up with a polite way to tell me that she’d rather die than let me touch her, when she was saved by the bus appearing up the street. I didn’t know if there was anything that could get her to try that strip club a third time, so if I wanted to do this, it was now or never. I dug out my wallet and produced a wad of cash held together by a rubber band. “Five hundred for a blowjob. Take it or leave it.”

She looked at the bills in my hand doubtfully, but I could see her considering it. That much money could go a long way for her family. I tossed the bundle at her, and she nervously caught it. “I, I didn’t say I was going to do it!” she complained.

“Then hand it back and get on the bus,” I told her, as it pulled up to the stop and the doors opened. Candi half turned towards it, then looked down at the cash in her hand. It was one thing to just say no to potential money, and quite another to have to actively give it back.

“Just a blowjob?” she said, half question, half request. I nodded. “Where? I’m not going to follow you somewhere, and I’m not taking you back to my house.”

Her house? What an adorable lie. She shared a dorm room with two other girls, whose info I already had just in case. No sense in calling her out on it, though. Instead, I just raised my hands and indicated the general city around us. “There’s plenty of motels around here. You pick whichever one you want. I’ll pay for the room, in addition to the five hundred.”

She hesitated, caught between going with me and getting on the bus. Her hand squeezed the dollar bills, and I saw her reach a decision. “Fine. But just this once, and just the blowjob.” She gave me a steely look. “And if you try anything, I will kick your balls up into your stomach.”

She could, too. Teenage Candi had won some high school karate thing a few years ago, and it was clear that she still kept in shape. I had a big weight advantage, but it was all fat. I wasn’t going to be physically coercing her into anything.

Not that I’d need to.

The motel she chose was pretty rundown, but it would do. She picked the room, and I noted she chose the one closest to the manager’s office, probably in case she had to run or call for help. Smart.

Once we got in the room, I didn’t waste any time, shucking my pants and underwear to the floor, and sitting on the bed. “Dig in,” I told her cheerfully. I couldn’t help feeling a little proud as she stared at my prick in trepidation. I wasn’t porn star sized, but I had nothing to complain about. She awkwardly knelt in front of the bed, tucked some stray hair behind her ears, and reached out with a trembling hand.

I don’t like girls cheating with their hands when they’re supposed to be giving head, but I let it go this time. She pumped my shaft slowly, then licked the head a few times.

I’d love to say I received the best blowjob of my life from beautiful Candi that night, but she was even worse at blowjobs than stripping. She couldn’t keep to any consistent rhythm with her hand, and she was just sort of poking me with her tongue. I never even made it into her mouth.

The entire mediocre affair lasted less than three minutes. If my head hadn’t been bursting with fantasies of what I’d do with her later, I doubt even three hours would have been long enough to cum from her poor performance, but mind triumphed over matter. As soon as she felt my shaft pulse, she backed away, leaving my load to spurt onto the floor instead of her face. What a shame.

Candi could barely bring herself to look at me after I finished. “Would you like to go get something to eat?” I asked her as I shrugged my clothes back on. “I think there’s a diner up the block that’s still open this late.” She shook her head without saying anything. “Really? You were saying earlier how hungry you were.”

“I lost my appetite,” she muttered.

My cock twitched happily at the idea of her stomach empty of anything but my sweat and precum, but I wasn’t going to get anywhere with her like that. “Sorry to hear that,” I said instead with feigned sympathy, and pulled a bit more cash from my pocket. “Here, then. For when it comes back.”

Candi reminded me of a skittish wild animal as she warily extended her hand towards the money like she expected it to try and bite her. Once she’d seized it, she quickly snapped her hand back, holding the cash to her chest protectively. Only then did she look down at the sixty or seventy dollars she’d grabbed. “I… I don’t need all of this,” she said quietly. She separated out a five dollar bill and offered me everything else. “Five dollars is enough for a meal. You can have the rest back.”

God, she was fucking adorable. I shook my head. “Keep it. You look like you could use a few extra meals.” She blushed, but didn’t argue.

I dialed her an Uber, and we waited in silence until it arrived. Just before she left, I handed her a scrap of paper with my phone number on it. “In case you ever need some cash again,” I told her.

She looked at me doubtfully, but she took the paper.

*

It took another couple weeks for her to text me again. It may have had something to do with an unfortunate fire at her parents’ house that destroyed pretty much all of their possessions. But who’s to say?

Regardless, her text was short and to the point: “8pm, same motel”. She was waiting for me outside, dressed in much more conservative clothes than she’d worn to the strip club, though they were as worn out as everything else I’d ever seen her in. She also looked even more nervous now than she had the first time. That had been largely a spur-of-the-moment decision, while this was probably something she’d agonized about for days, and been dreading since the moment she sent the text.

She crossed her arms when I approached, and I caught her tapping her foot a little. “Cash first,” she declared. She was trying to sound tough and no nonsense, but her eyes betrayed her anxiety. She was afraid that I was going to try and take advantage of her. And I absolutely was, but not with something as crude as trying to skip out without paying.

“Of course,” I said pleasantly. “But first we’ll have to decide what you’re doing and how much I’ll be paying for it.”

“The same as before,” she said, fidgeting. “The, the blowjob. For five hundred.”

I gave her an apologetic look. “Sweetie, I’m never going to lie to you,” I lied. “What you did last time wasn’t worth five hundred. I’m not sure it was even worth five. That’s not your fault; I’m the one who made the offer, and the one who said five hundred. You earned that money fair and square, and I’m not going to ask for any of it back, but I’m not going to pay five hundred for more of the same either.”

Candi wore a hurt and humiliated expression, though she was trying not to show it. I doubt she wanted to admit even to herself that she felt bad about not doing a better job sucking a stranger’s cock in a motel room. “Then why give me your number and meet me tonight?” she accused. “Just so you could tell me how awful I was?”

“Sweetie-”

“Candi.”

I smiled, as though her stripper name was any less insulting. “Candi, I’m not here to waste your time or make you feel bad. Like I just said, we haven’t decided yet what you’re doing or for how much. I would be more than happy to pay you another five hundred dollars tonight. We just need to figure out what for.”

“Like what?” she asked skeptically. Then she added quickly, “I’m not going to have sex with you. Vaginal sex, I mean. Or, or anal. Not for any amount of money.”

I doubted that very much, but this was hardly the time to push back on that. “Then I’ll never ask you to,” I said smoothly. “We’ll make that a ground rule. But that wasn’t what I had in mind at all anyway…”

A few minutes later, I was sitting on the same bed in the same motel room, with Candi kneeling before me, but this time my cock was in a place even warmer and cozier than her mouth. My new project’s tits were as soft and smooth to the touch as they’d looked at the club, and though her technique with them was as awkward as her dancing and sucking, they were more than good enough to make up for it. I itched to smack them, maybe give them a good bite or two to make her squirm, but I restrained myself. For now.

Candi wore an expression somewhere between boredom and nausea as she mechanically pushed her breasts up and down over my shaft, making no real attempt to please me. Her eyes were screwed shut, and I got the impression that she was trying to pretend that she was anywhere else doing anything else. That was no fun at all.

I gave it about twenty minutes before I sighed and told her to stop. “Sorry, Candi,” I told her. “You clearly don’t want to be doing this, and that’s a real turn off for me.” If I’d still been wearing pants, they might’ve caught on fire from a lie that big.

“I did what you wanted,” she said defensively. I was pleased to see fresh hurt in her expression; part of her was ashamed about her poor performance, and not just because she needed the money. She was a girl used to overachieving, not under. “I’m not giving it back.”

“That’s fair,” I agreed. “But... I don’t think we should meet up like this again.” I was taking a risk here by pushing her away, but it was a calculated one. Now that she knew I was a potentially recurring source of cash, could she really justify letting me slip away?

The gamble paid off. “Wait!” she protested with just a hint of panic. “Isn’t there... I mean, I’m trying, I really am, I’ve just never done this before.”

“Yes, that much is obvious,” I agreed, and enjoyed the little flinch that produced. “There is something that would make this better for me, but I already know you’ll hate it, so suggesting it wouldn’t do anything but make you angry. I don’t want you to think I’m some kind of thoughtless jerk or evil predator.”

“Wh-what is it?” Candi asked uncertainly, and I could see desperation in those gorgeous blue eyes. “I won’t get angry if you just say it, as long as you’re not going to... to try and force me.” Her resolve was already crumbling, and despite her earlier declaration, I knew that with the right words, I could have her on her back with her legs wrapped around me tonight.

But I wasn’t feeling that kind.

“I have... a sort of fetish,” I told her, acting embarrassed. “I find it really sexy when it’s being recorded. But like I said, I know you won’t be okay with that, so it’s fine, really.”

I watched her mentally weighing her options. There was no way she’d agree to make a sex tape, but that didn’t make it feel okay to miss out on the money. She wanted to be okay with my suggestion, but it was far too much for her. Which meant a little push and...

“Oh!” I blurted out, as if the idea had just occurred to me, “What if we used your phone for it? You could delete everything as soon as we were done.”

“And you’d be okay with that?” Candi asked, rightfully suspicious.

“Of course!” I assured her. “It’s just the act of recording that does it for me. I don’t have any interest in holding on to it.”

She didn’t look convinced, but she was having a hard time saying no. She reluctantly pulled her phone out of her back pocket. “If you try to email or text this or whatever to someone, I’ll make you eat this phone, understand?”

I nodded. “Loud and clear. Tell you what: you start it recording, and then just hand it over. You catch me so much as touching the screen at any point and the whole thing is off.” She still looked suspicious, but she wasn’t going to get a better deal than that and she knew it.

Not everything I say is a lie. Watching Candi’s hardworking tits through the phone screen made the experience much better. And the best part, which I doubt she’d considered before agreeing, was that there were no more closed eyes for her, not if she wanted to keep track of what I was doing. I kept the phone held up to my face, forcing my new pet to look right up at me while she worked, wary of any attempt to pull anything.

Those anxious baby blues and soft tits were too much, and I barely made it another five minutes before I popped. And when I did, I received an unexpected surprise: Candi was so focused on her phone that she didn’t notice me about to cum. So instead of pulling away when I was about to finish, like I’m sure she’d planned to do, she kept right on massaging me until I spurted all over her chin. Her shock and disgust were better than the orgasm.

Just as promised, I handed over the phone without doing anything to it. After all, I had other cameras already discreetly recording this for my later enjoyment (I’d been pretty certain she would choose to return to this familiar spot). In particular, those startled eyes when the first drops of spunk hit her flesh, the way she flinched... I was going to masturbate to the gif I made of that quite a few times. Right now, the goal was just to push those limits of hers, little by little. Call it foreplay.

It may have just been my imagination, but she already seemed slightly more compliant as she got dressed. It could have been embarrassment over her slip-up, or her own poor performance, maybe even a touch of guilt that she’d doubted poor old me. I did my part to help things along by offering her another handful of twenties before she left.

She looked at them warily, but she did so after accepting them from me. “What’s this for?” she asked, and I caught her eyeing my cock, which was already regaining its heft as I thought about her future.

“For letting me film you,” I said, as though I was surprised she had to ask. “I’m not going to ask you to do me a favor for free. A twenty percent bonus felt like the right thing to do.”

“But, we already agreed to the five hundred,” she said doubtfully. The sweet thing was worried about overcharging me.

“Five hundred for some time with those lovely breasts of yours, yes. That was before the phone became part of it, so there you go.” I gave her my best smile. “I’m not going to cheat you out of your money just because you didn’t know any better.”

“Th-thanks,” she mumbled, pocketing the extra cash. Then she hurried out of the motel room.

We were back there just a few days later so that she could give me a handjob. And less than 48 hours later, she was there tasting my balls. Both sessions were recorded with her own phone, and she was increasingly comfortable each time. The two grand she’d now earned from me was the only thing keeping her world intact. If her cash flow dried up, she’d have to drop out of college and dedicate her time to finding work, and she was smart enough to know that it would mean getting caught in a downward spiral. Her degree was her only chance to save her family, and I was her only chance of saving her degree.

It was about a month after our first meeting at the strip club when I cinched the noose a bit tighter. “You’re a nice girl,” I told her on our fifth meet. “But this isn’t really working out.”

We were already in our usual motel room at that point. I was naked from the waist down, while Candi stood opposite me fully clothed, trying like usual not to look at my prick. She trusted me enough by now that she was willing to come inside with me first, and then decide what it was we were doing. I think the fear that someone might recognize her while she was standing outside a seedy motel discussing sex acts with an older man played a part too.

The blonde bit her lip in an adorable way. “If you need me to go further, I...” She looked down and fidgeted uncomfortably.

“See, this is exactly what I’m talking about,” I told her. “I want a woman who’s into it. If I just wanted sex with a stranger, Candi, I could walk down the street and find it for a fraction of the price, and with someone who, well...” I let my voice trail off, forcing her to fill in the blank herself. Someone who was actually good at it.

“I hardly even know you,” she retorted weakly. “You’re at least twice my age and... how could any woman really be into it in circumstances like this?”

“I don’t need you to be REALLY into it,” I said. “Just to act like you are. No offense, Candi, but how am I supposed to enjoy my time properly with a girl who can barely bring herself to look at me? You act like I’m this horrible monster taking advantage of you, even though YOU have been calling ME here every time.”

Oh, if only I could bottle that look of guilt on her face. My future cocksleeve really was such an innocent girl. “…You’re right,” she admitted. “I’m sorry, it’s just, I don’t know you, and I have to be careful, but I’m sorry. I, I think I could fake it, if that’s really okay.”

I pretended to consider the offer. “I’d have to lay down some ground rules,” I told her. “I don’t want to surprise you with something while we’re in the middle. I want you to know exactly what you’d be getting into before we agree to give it a try.” She nodded gratefully. Yep, I’m a real saint.

“First rule is to make this a little more fair. I’m still going to pay you in advance, but I don’t want to pay you and then get nothing more than a quick smile or something. I want to know I’ll get my money’s worth. So here’s what I propose: I pay you double -“ I saw her eyes light up at the prospect of a thousand dollars just for an evening with me -“but every time we agree that you broke a rule, I take one hundred off the top. That means you can mess up five times and still be back where you started.”

“What if I mess up more than ten times?” Candi asked, looking a little nervous at the idea.

I waved my hand. “Then we’ll roll it over into the next time. I’m never going to demand that you pay me anything. BUT, this does mean you might have times when you’re not getting paid at all for a session. I need to know right now that you’ll be okay with that, and that you’ll still do the job you were being paid for. If you’re going to mess up a bunch and then just walk out, we might as well part ways here.”

Candi considered the idea. “What are the other rules?” she asked. Smart girl.

I ticked them off on my fingers. “First, that you smile the entire time. That’s from the moment I hand over the money, to the moment we’re all done. Second, that you address me respectfully and as ‘sir’. Every statement you make without ‘sir’ in it counts as a penalty, and so does any rudeness or hostility. Third, that you answer every question I ask you. Don’t consider anything rhetorical. Fourth, after I finish, I want you to thank me for my semen and tell me that you love me.”

Her disgust at the rules was plain on her face, but she didn’t reject them. “I... think I could handle that,” she said quietly.

“Don’t say yes just yet,” I warned her. “Last rule: no clothing.” She instinctively recoiled from the idea. “I’m literally baring myself to you every time we do this,” I explained. “Nothing makes me feel more unwanted than a partner who refuses to reciprocate. At the start of every session, we’ll both strip. If you decide at any time that you want to put something back on, you can, but that’s a thousand dollar penalty right there.”

She hesitated, and I saw her eyes roam across my body. I think she was just as anxious about seeing the rest of my naked body as she was about showing me hers. But not anxious enough to turn me down, so she eventually swallowed and nodded. “Okay. I accept.”

Candi undressed far faster and with less theatrics than she had at the strip club, but it was a thousand times sexier. Her fingers trembled as she unclasped her bra, and she wore an expression of such shame on her face when she slid her panties down her legs that I could’ve cum right then and there.

She tucked the thousand dollars into her discarded pants, making sure to put them far away from me, and then smiled. It wasn’t a very strong smile; she looked on the verge of tears, and her eyes were full of terror. It was perfect.

She knelt in front of me, trying not to stare at my pudgy belly or flabby legs. Meanwhile I soaked up her beautiful curves and imagined how wonderful they would feel squirming beneath me. From the way my blonde nymph aggressively attacked my cockhead with her tongue, she wanted to get this over with before she could do something wrong, but I wasn’t about to let her get away that easily.

“Have you learned to love the taste of me by now, sweetheart?” I asked. I nudged my clock away from her so I could rub it against her lips instead, turning them slick with precum.

“Yes sir,” she said automatically, though her smile became gruesomely forced. The word ‘sir’ came out awkward and forced; I could tell it wasn’t a term she used very often.

“Mmm hmm, I can tell. And I bet you’re looking forward to swallowing a load of hot cum too, aren’t you?”

Her expression immediately twisted into disgust. “That wasn’t what we agreed!” she accused, backing away from my crotch.

I sighed. “That’s three, Candi. No smile, no sir, and I don’t appreciate that tone of voice. And I wasn’t telling you to do anything. We’re doing some role playing, remember? If I expected you to actually swallow, I would’ve discussed it with you beforehand.”

To say she looked unhappy about losing three hundred dollars thanks to a single outburst would be underselling it, but she was smart enough to see that arguing wasn’t going to get her anywhere. I’d blatantly provoked her, but mildly enough that she could tell herself that it was her own fault for being unprepared. “You’re right,” she conceded. “I’m sorry, I’ll start over.”

She switched her smile back on and leaned her head in to get back to work, but I gently put a hand between us to stop her. “That was another statement without ‘sir’”, I said apologetically. “Are you sure you can really do this? If you keep making mistakes, neither one of us will be very happy by the end of this.” I clicked my tongue at the look of humiliation that passed across her features. “And there’s five. Your money is already half gone, Candi. Why don’t we just call it a night? You can keep the remaining five hundred.”

I was playing with fire here. She wanted to quit. She wanted it bad. Most girls would jump at the chance I was offering. They’d regret it later, but in the moment they’d just want to put their clothes back on and go home with the money in their pocket. But I was betting that Candi wasn’t most girls.

My gamble was rewarded as she forced herself to smile again. “Please give me another chance, sir,” she pleaded, and this time the title came out so naturally. “I know I’m not very good at this yet, but I’m willing to try, sir.”

I let myself be convinced, and sat back while her tongue returned to where it belonged. “Are you hungry?” I asked her.

“Mmm, a little, sir,” she said as she slurped on me.

“Then I’d better be a gentleman and fill that belly. How does a mouthful of cocksnot sound for dinner?”

Candi hesitated, her smile faltering slightly, but this time she maintained her composure. “It sounds wonderful, sir,” she said. “Th-thank you for treating me to a meal.”

“Very good,” I said approvingly, and scratched her head like the good pet she was on the road to becoming. “It sounds like I underestimated you. Maybe you can pull this off after all.”

“Thank you sir,” she replied, and her gratitude sounded perfectly sincere.

“So what’s your favorite part of sucking on my cock?” I asked her.

That one got her. “I, uh, I don’t know...” I held up six fingers and she begrudgingly nodded her agreement. “I don’t know, sir,” she corrected.

“Let’s think about it then,” I teased. “Do you like that warm, musky smell?”

“Yes, sir,” she said, and though she didn’t lose her smile, her nose crinkled in distaste at the reminder.

“It’s gotten stronger over the last couple weeks because I’ve stopped washing down there,” I told her gleefully. “For the last few weeks I’ve been getting by solely from your tongue baths.”

That actually got her to retch slightly. “I’ll have to call that two,” I told her. “No smile, and very rude.” She gave me a miserable, pleading look, but offered no argument. ‘Do you know what MY favorite part of you sucking my cock is?” Candi shook her head as she switched the smile back on. “It’s knowing that right now, it’s all about me. This isn’t a mutual act of pleasure, no matter what some whores might pretend. I have a beautiful blonde college student naked and on her knees in front of me, wholly focused on convincing my dick to spurt.”

It was on the verge of doing just that by now. Candi was a quick learner, and her tongue was much better now than it had been when we started. But before I let myself finish, I had a little more work to do. So I nudged myself away from her, enjoying the adorable sight of her tongue chasing after me before she realized what was going on and leaned back.

“You know what would be REALLY sexy?” I mused innocently, letting her take in the sight of my precum running down my throbbing shaft. “If you begged for it. If I heard your sweet voice pleading for me to shoot off, I might just explode on the spot. Gosh, even if you weren’t licking me at all, hearing that would be worth the hundred dollars.”

“Two hundred,” she said immediately. “Sir.”

“One hundred,” I corrected. “It WAS two, and then someone forgot that I don’t ask rhetorical questions, didn’t she? ......And now it just became gratis.” It was pure joy to watch it sink in that she wasn’t going to be paid a single cent for this blowjob that she hadn’t even completed.

Candi kept at it, but by the time I relented and let my cum spatter the floor, I was already looking at a six hundred dollar discount on the next one too. “Th-thank you for your cum, sir,” she said in a tired, defeated voice. “I love you.”

My fledgling cocksucker was quite surprised when I handed back half of the thousand dollars she’d returned me. “You’ll still begin down six hundred next time,” I explained, “but you came here tonight expecting five, and I wouldn’t feel right sending you home with any less. I know you were trying your best today.”

I kid you not, fair readers, there were tears of happiness in her eyes and warm gratitude in her tone when she thanked me. And why not? From her perspective, I was becoming one of the most kind, honest, and generous people in her life.

For the next few sessions, I worked on getting Candi to adapt to the new normal. Every time she submitted to me, it became a little easier for her. A little more natural. And she was eager to become good at this. That first session wasn’t the only one that ended up being on the house. I made sure not to be TOO rough on her. It was very important that she accept that her failures were her own fault, caused by a lack of discipline and self control, not mine. It also wouldn’t do to keep making her work for free. If she stopped seeing me as a source of money, she’d have no reason to keep coming back.

So sweet, hardworking Candi was still going home with a few hundred dollars most nights. Sometimes she was even good enough to finish with more than her starting five hundred. But far more often it was less, and always because she wasn’t a good enough whore.

Our meetings became much more frequent, until it was rare for a single day to go by without her mouth around my cock. The poor thing actually accepted the impression that she was the one imposing on me, that I was doing her a favor by finding the time to meet with her whenever she asked. She was fucking me more, getting paid less, and increasingly convinced that I was her greatest ally.

I had the time of my life playing along. Before and after our sessions I would make small talk, or joke around with her. The next time I offered to buy her a meal, she accepted, and I made sure to send her home with plenty of leftovers. At some point, we started meeting for lunch a few times a week, and I’d usually take the opportunity to spoil her with gifts, like bringing her to a department store and letting her pick out some new outfits to wear.

When I talk about our relationship like that, it almost sounds like she was the one taking advantage of me, and I’m sure that from time to time she worried that she was doing just that. But even if I hadn’t been planning to fuck her into the ground one day, I would have considered all our interactions time and money well spent. Candi was always a delight to be around, especially as she relaxed more and more around me. If I’d been twenty years younger and not a sadistic sociopath, I think I would’ve genuinely fallen for her. She was charming, clever, kind… I had an enormous amount of respect for her character, and I mean that.

If I hadn’t, it wouldn’t have been half as fun to ruin her.

As time went on and she began to trust me, she opened about her school experiences, her life back at home, and even discussed the terrible things that had happened to her parents in the last few months. I was nothing but sympathetic, of course, and insisted on giving her two thousand dollars to pass along to them anonymously.

I’m not trying to claim that I was some suave sweet talker that won her over with my charm. The truth is, all of her family and close friends were hundreds of miles away, and she hadn’t made much in the way of friends at school. The poor thing was starved for affection, and I offered it freely. Before long, I think she genuinely considered me to be one of her closest friends, in or out of Princeton.

And when we were having sex, I trained her like the good natured bitch she was. I taught her all the right ways to lick my cock, to suck on it, to tease and play with and excite it. She was as quick a learner here as she was in any of her classes, and soon she was a champion cocksucker. Deepthroating was the most fun lesson by far, because her gag reflex didn’t care about her smarts or her good intentions. She’d gurgle and choke as she tried to swallow my shaft, and I’d add insult to injury by constantly asking if she was alright, forcing her to smile around my prick and assure me of how much she enjoyed gagging on my fat cock.

Some lessons were more subtle than others. It took a little while for her to realize that I was much more lenient with her while she was directly servicing my cock. I was normally merciless about enforcing our rules, but in the rare occasions I did forgive small infractions or pretend not to notice mistakes, it was always when she was in the middle of pleasing my dick. It might seem like a simple and obvious lesson that the best way to keep me happy was to keep my dick happy, but it would eventually be the most important rule of her life. I knew she’d taken it to heart when she stopped pulling back to answer my questions, instead letting my prick remain in her warm and pleasant mouth while she spoke. Soon, there was barely a moment in her blowjobs where my dick wasn’t between her lips or being caressed by her tongue.

About the only skill she didn’t pick up was swallowing my cum. She could tolerate precum, but she had an aversion to semen that bordered on a phobia. I had plans for how to deal with that, but for now I didn’t press. Besides, I managed to convince the sweetheart that I always felt embarrassed to see my cum splatter on the floor when I finished. After that, she started letting me spray my thick loads over her gorgeous face and hair every time, and seeing her cringe when it hit was almost as good as making her gulp it all down.

Six or seven weeks passed like that before the perfect opportunity arrived to take our relationship to the next level. It was our first session in a few days because she’d been busy studying for exams. So not only was she hurting for cash more than usual after the drought, she was mentally exhausted and prone to making mistakes. And I made her pay for it. I hammered her for error after error, until she was actually apologizing to me for doing such an awful job.

By the time I spurted, poor Candi was on the verge of tears. She hadn’t just ended up sucking my cock for free; she was down almost three thousand dollars. At her current rate, it was likely going to take her at least two weeks straight of better performances before she even began to see cash again.

A less patient man would have jumped in with suggestions at that point, but I held my tongue. It was important she do this herself.

Candi cleared her throat nervously as she got dressed, and I didn’t miss that her fingers were shaking a little. “How much, um… for… for more?” she asked quietly.

“More?” I repeated, as though I had no idea what she was asking.

She bit her lip. “If I did more, I mean. With you, sir. More than just my mouth.” She’d been calling me ‘sir’ more and more, which I had no complaints about. I think it was easier for her to get into the habit of saying it too often and risking embarrassment than losing money by saying it too little. She used to blush every time afterward, but either it didn’t bother her as much anymore, or she just didn’t notice it most of the time.

“That could mean a lot of different things, Candi,” I reminded her. “And I don’t want to make a bad assumption and hurt your feelings. What specifically are you asking about?”

Her face flushed. “…Sex,” she said finally. “How much if we had actual sex…?”

“Well, that depends on a lot of factors,” I said casually. “If we were talking just plain missionary, then I can’t see myself paying more than a couple hundred.” It was a struggle not to laugh at her look of profound disappointment.

“But you’re willing to pay more for blowjobs,” she protested.

“Because I like having my dick sucked, especially by lovely girls like you. If we’re talking boring, regular sex with no extras attached, even two hundred is being generous, honestly. I could have nearly as a good time by myself with my hand.”

“…Extras?” Her tone was curious, with more than a little morbid fascination behind it.

“You know me pretty well by now, Candi, you know I like things done a certain way. When it comes to sex, my rules are even more stringent, and I’m less tolerant of failure. And before you say something, this isn’t a question of skill. Honestly, my tastes are… niche. And extreme. The sort of stuff I really want in bed, what I would be willing to pay good money for, is also stuff that most girls don’t enjoy at all, and I can’t blame them for it.”

“Like what, sir?” she asked nervously.

I shook my head. “I’d rather not even talk about it. The last thing I want is for you to think I’m trying to get you to do that sort of thing. I like you, Candi. You’re a good girl, and I have a lot of respect for you. I don’t want to treat you like… like I prefer to treat my sexual partners. You deserve better than that. I think it would be best if we didn’t bring this back up again.”

And before she could argue, I left.