Man of Integrity

Story Info
An older man ensares a young student.
7.1k words
4.52
20.5k
21
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

This is another deviation from my normal fare (at least, I think so; some would disagree). Please pay attention to the category the story is in because the story caters to it; those looking for characters or situations more like my long series will be disappointed. That said, this one isn't as harsh as "Post-Nuptial agreement".

Hopefully some readers will enjoy this.

========================================

I'm a dirty old man. The worst of the worst. Society looks down on me in almost every way, and many consider me worse than murderers and violent racists. Worse than pedophiles, even; at least they own up to their desires.

What they really mean is they can be arrested for them, because what they're doing is actually illegal. Me, I'm just immoral. A-moral, maybe, too.

But I still have integrity.

"Old" is debatable, but given the perspective of the people involved, 46 is definitely old. I have, however, taken pains to make sure I don't look it as much as possible. When my hair started greying, got rid of it. when my eyesight faded, got contacts, then laser surgery when I could afford it. I figured out in college that while many women might talk about guy's personalities and getting to know them, having limited body fat, good grooming, and decent muscle definition got many of them naked more reliably than anything else except chemicals. With that knowledge, I made sure to exercise and eat in a way that kept my physique better than average for men of my age.

Eventually I attracted a particular woman who stuck around longer than average, and I didn't mind as much. We got married, had a couple of kids, got a house, but things didn't work out. It was my fault, one hundred percent. I didn't even contest it in the divorce.

My first problem was that I liked my work more than I liked my wife or kids. Where the kids were concerned, I made the effort to show up at the appropriate events and functions, and I made sure Christmases and birthdays were acknowledged, but my heart wasn't in it. I was going through the motions, and everyone could tell. My wife was fully devoted to my kids, and she tried to pay attention to me too, but gradually my lack of interest in my children began overshadowing her interest in me. That dovetailed with my other problem.

I figured out a long time ago I like thin women, in all respects. Curves don't do it for me. As soon as the measurements between a girl's hips and waist differ by more than 10, I lose interest, ditto if any number involved is above a 35. And if they have to wear a bra I'm out. Forget a handful; I'm one of those odd guys who actually likes it if a girl raises her arms and her boobs vanish.

I also don't like wrinkles, which is where things fell apart with my wife and I cemented my legacy as a dirty old man. It's hard for women over a certain age to stay thin and keep their skin perfectly smooth. There's a billion dollar industry of creams, injections, and surgeries built around that fact.

You really only find it in teenage girls.

That's why I'm sitting up in a hotel room, pouring a glass of sweet Riesling on a side table while swirling a bit of bourbon in my rocks glass, and waiting.

Downstairs and across a connecting corridor or two are several thousand chairs being set up in a ballroom, and milling around between the two buildings and all sites around are somewhere between one and two thousand teenagers with maybe three to four hundred chaperones trying to keep them from getting into trouble. It's a state-wide science competition for the students, competing for scholarship awards. Day one of the competition is complete. I was one of the judges.

I work as a chemical engineer for a pharmaceutical company and have a masters in chemical engineering and a minor in computer science. Judging is volunteer work, unpaid (though the organization usually likes to throw some five to ten dollar swag at the judges as a thank you, and pays for some food). You spend a few hours watching the kids give presentations on their efforts to revolutionize the world of science. Most of it is mundane, though some of the groups show real innovation and understanding beyond what you'd expect at their level. A lot of them are fully invested too; many of the kids are the high-flying types, desperate to maintain a GPA that gets them into Ivy schools, and looking for any accolades that might boost that hallowed transcript.

Despite what anyone might think, I judge the projects objectively, based on the merits of the science. Maybe I only tell myself that, but my track record shows I have no problem giving high marks to a bunch of pimply, glasses-wearing, shabby guys who seem allergic to bright light, just like I won't hesitate to sink the scores of a group of bubbly bimbos who can't even bother to stay consistent in using the metric system. I am, as I said, a man of integrity.

But I also keep my own notes. I mark the teams with senior girls. And I have my own scoring system. It's usually based on body weight, height, hip/waist ratio, and cup size.

Even though they don't get their final numeric scores until well after the competition, the teams get access to written comments from the judges as soon as they're done scoring. That's where I let my computer science degree work for me.

The security on the system that records and reports the scores is laughable. It was built for a group run by public and private school teachers; they may not have gotten the lowest bidder to do it, but whoever it was definitely bid in the bottom tier. It's not as bad as it could be, but security was not their primary concern, and it hasn't had a real overhaul or update on the software in at least 5 years. So slipping a little virus in there is child's play, at least for me.

My person of interest this time is Rory. Budding materials scientist who, along with her partners, tried to design a more efficient soldering torch based on the melting points of modern solder materials. Their presentation was good, but they suffered because their prototype failed in their demonstration when their power cord broke. It would be an easy fix, but without a demonstration their score suffered.

Today had been round one. The best performers of today's rounds compete tomorrow, and that was where you could win real money; scholarships, grants, that kind of thing. Their team might get there; some of the other projects were truly abysmal. But a higher score would help.

So when Rory logged in to check on the comments from me (by phone, of course, because all of the kids used their phones), my virus grabbed her cell number. And then it sent her a text.

"If you want to guarantee you make it to the next round, go to room 1712 at 5:30 tonight. You'll find a keycard behind the planter just outside the elevator. Yes, this is for exactly what you think it is. Except your ass is what I'm interested in. I promise if you let yourself, you'll enjoy it."

I'm good at sex. I've had several women tell me that over the years, and before things fell apart my wife definitely shared my bed more often than was necessary just to have kids. And I either got them off or all the women I was with were really good at faking muscle spasms and Kegel contractions. Either way, I'd bet any amount of money I had that I knew more and was more skilled at sex than any of the boys these girls might have been with.

The insistence on anal? That's just sensible. These kids think they're invincible. Sure the girls might be on birth control, but are they always remembering their pills? Are they remembering not to also take something or eat something that might counteract the effects? And one broken condom screws up things for everyone; even a mil of precum leaking in the vagina means pregnancy chances are no longer zero.

I'm a dirty old man, but I'm not an idiot. Mostly.

After leaving the glass of wine and a few other things, I take the stairs up four floors to my actual hotel room and open my laptop. In a small window in one corner is the webcam feed from room 1712. In the other is output from the texting client I set up.

As I said, I'm not an idiot. The students are often desperate for grades and recognition, but not all of them have the right mix of personality issues and competitive nature that make them willing to take me up on the offer. No less than ten girls got texts from my anonymous virus bot with similar invites. Two of the girls didn't even look at the messages, four more deleted them shortly after reading, and two others wrote back fairly aggressive and inventive replies questioning my gender, sexual orientation, hygiene, fashion, and housing status.

Rory and one other girl named Nadia were the only ones that had read them and not replied, but also hadn't deleted them. The texts self-deleted after 5 minutes to erase evidence that could be shown to administrators or chaperones. And, of course, I wasn't actually in the room they were invited to. If they dragged a bunch of other people there to show them what was going on, there was vanishingly little evidence for them to find.

Maybe they'd just ignored them, but in my experience when the messages were read and not deleted or replied to it meant the girls were thinking about it. It remained to be seen whether thought would turn into action.

5:30 passed with no activity through the camera. I sat in sweatpants, Crocs, and a loose sweatshirt, waiting. The anticipation and my mental memory of the girl, half dressed up in slacks and a navy blue blouse, were enough to make me half hard. I resisted the urge to start playing with myself; if things went well I wouldn't need to bother with that.

At 5:38, as I was starting to think I might have to give up on Rory's charms, I heard scraping at the door through the webcam's mic. Then there was the whirr-click of the lock disengaging.

The door opened and she shuffled in quickly, nervously. She let the door close behind her and she jumped as it closed. Then she looked around.

She was in the same outfit from the competition. The slacks were tight on her slim legs. When she stood still her thighs had almost a two inch gap between them. Her ass was a perfect oval, curving around and up to her back but not pushing out or protruding. Her blouse was loose, but it hung evenly all over, no bulging mammaries pushing out the material. Her head was an inverted teardrop, with her chin so narrow it almost seemed to come to a sharp point. Her face was a little flat, but her cheeks popped out under her oval eyes. Her long hair was light brown with blonde highlights and ruler straight, falling down to her mid back and framing her face in a square with her bangs.

My groin surged in anticipation.

I clicked a few buttons and her phone rang. That also startled her and she studied the phone for a while as it rang at her. I wasn't sure if she was hesitant or just confused; half the kids forgot that their phones were actually capable of real-time voice communication, and they only knew what their ringtone sounded like because they'd heard it used as a sound effect on a show. She finally clicked to answer.

I typed, and the words came through her phone by hijacking its onboard assistant voice program. Siri was about to get naughty.

"Hello Rory. Thank you for coming. There's some wine on the table if you'd like."

Rory stared at her phone in shock for a while, but then glanced up and saw the wine. "I'm...I'm not old enough..."

"Nobody will know, and it'll help relax you," I sent through her phone again.

Hesitantly, she made her way over. I chose Reisling because it was sweet enough to ease in the kids used to soda or flavored water. It was still wine, and there was no hiding the alcohol, but I wasn't trying to trick them into getting drunk; I'm a man of integrity. The only thing I kept from them was my identity.

"So you know why you're here, right? You know what's going to happen?" I sent through the phone after she'd taken some sips of the wine.

"I'm...you're...you're going to have...um...anal sex..." Rory stammered, and the last was more of a mumble.

"Rory, if you don't want to do this, you should leave," I said.

"No! I...you said you could get me...get us to the next round, right? Guaranteed?" she said.

"I can," I said, "But you aren't guaranteed to win. It just gets you there."

That seemed to stiffen her resolve; she stood a little straighter. "I'm doing this then," she said, then she took a bigger gulp of the wine and winced a little. Then her resolve seemed to waver a bit. "I...I haven't done it before," she muttered.

"Anal? Or sex at all?" I asked.

"I've had sex! I'm not a virgin," she insisted, and it sounded like she'd had to defend that claim a few times, "I just...I've never done it back there."

"Well I promise it won't be as bad as you're thinking. The key is to relax, and to prepare. Now here's what's going to happen. If you go into the bathroom there will be a shopping bag in the vanity, tucked behind the cleaning bucket. Inside is a cleaning kit with instructions on it. Use it and the wipes inside."

Rory nodded as if it was a simple enough task, but I knew that attitude would change when she actually opened the bag. Seeing an enema kit seemed to be the first "real" moment for most of these girls, when even the transcript and grade-hungry ones started re-thinking what they were doing. But the last little push always came because of the money. Top prize in the competition at this level was a thousand dollar scholarship for each member of the team. A pittance, in the grand scheme of things, but to most of the kids a thousand dollars was a small fortune.

"There's also some tanning goggles and medical tape in there. After you're all cleaned up, you're going to take off your clothes but leave your panties on. Then put the tanning goggles over your eyes, and use the tape to tape them on. I'd recommend going over the lens and then to the side toward your ears. And tuck your hair out of the way. Then come out and stand in front of the bathroom door until I get there."

The mention of taking off her clothes made Rory nervous, I could tell. She stared at the phone, her wine, and the bathroom a few more times.

"Rory, if you want to leave at any point just say 'terminate'. But you don't get guaranteed the spot unless we go all the way. And I'm not going to rush right in and start. But I promise if you relax and go with it, you'll enjoy this."

She took some more deep breaths as she cradled the wine glass.

I'm a man of integrity; I wasn't lying to her. I wasn't going to go in there, bend her over the bed, and ass fuck her dry. That's only fun if you like hurting people and get off on the power trip. I actually like the feeling of anal, and it feels a lot better with lube and a relaxed partner who might actually be into it. And I knew all sorts of nice ways to get girls to relax. Usually it involved gentle rubbing, and a lot of work with the mouth.

Finally Rory made a decision, at least about the first part of things. She set the wine glass down and made her way to the bathroom. The camera let me see the bathroom door, but not inside the room; I'm not a pervert like that.

I spent a few minutes pulling up the camera feed on my phone and transferring the "text to speech" interface there too. I wasn't going to say anything; all my communication would still be through her phone. I could type pretty fast on the phone keyboard, but if my hands were busy I also had a few phrases programmed in that the app could transmit quickly.

I knew I had time; the recommended treatment with the kit was ten minutes, and I always added in another ten for the girl to work up her nerves. I also took the stairs down; if I ran into anyone I could always make the excuse that I was on my way back from the hotel gym. It was also a lot easier to hear if someone was approaching.

I checked my phone when I got to the correct floor and saw Rory hadn't come out of the bathroom yet. It was another decision point for the girls; the prep work for anal is a lot for some to deal with, and I know from talking to some women in other situations that some of them are perfectly fine with the idea of the sex, but doing all the preparation is what actually scares them off.

Finally I saw the door open tentatively and Rory slipped out. I sucked in a breath at the sight of her mostly naked.

Her legs were even thinner without pants, but they didn't have bulging muscles or bones on them; just thin stems of supple flesh supporting her. Her torso had the perfect shape; her ass protruding just enough to be round and even in her panties I could tell her pubis pulled back between her hips, which protruded slightly at the top of her legs. Her tummy was flat and there was the barest hint of her ribs showing as she sucked in a few deep breaths. Her breasts were little cones near the top of her chest with round pink nipples making little nubs at the ends of them. Her long hair draped around her thin neck like a curtain. Her face was ruined by necessity; nothing could make the goggles and tape look appealing, but the rest of her...

I had to resist the urge to bang the door open and dash out of the stairwell, but I definitely walked fast. I didn't want to leave her standing there to stew too long lest she think it was some kind of a prank or even that I'd lost my nerve.

I got the door open on the first try and stepped in. Rory stood no more than six feet away, the vision of her in person even more amazing than my view through the camera. Up close, she smelled flowery in the way teen perfumes do; I guessed she'd reapplied some just before coming out of the bathroom.

"Oh god, you're here," she said. Her voice had a mix of fear, surprise, and maybe, just maybe, a hint of anticipation. I literally saw her nipples harden. Nerves, or horniness? I'd find out very soon.

I tapped on my phone a few times. In the other part of the room, her phone said, "I'm going to touch you now."

"Okay," she said quietly.

I started with my hands at her shoulders. She jumped as almost anyone would when touched by someone they can't see. I let my hands run lightly over the silky skin, feeling the little bit of softness all women have regardless of size. I traced the contours of her shoulders, collarbones, and shoulder blades. It helped to relax her and tease me as I imagined what the softer, more supple areas of her body would feel like under my hands.

I slowly turned her so we weren't so close to the wall and she faced the bed and the window beyond. The window just looked out at the solid wall of another building, but that was good; I wouldn't have to worry about peeping Toms, Janes, or any other name.

I moved my caresses into a full-on shoulder rub. Not hard enough to be a deep tissue massage, but enough to maybe put her a little more at ease and get her used to my touch. I felt her relax a bit as I continued the gentle rubbing and squeezing, but I knew she'd tense up again as soon as something new happened. It was how this game played out in the minds of most of these women; they would get used to some activity or action and convince themselves it wasn't so bad. Until things escalated.

The key was to make sure each escalation was small enough.

I slowly moved her over to the bed. She tensed up when her legs hit it. In one move I spun her around and had her sit. Her legs were clamped together like a vice, crinkling the material of her panties. I didn't worry about it.

I quickly grabbed a pillow and tossed it on the floor next to the bed; I was going to be on my knees for a while, but not just yet.

I let one hand run through her hair and around her head while the fingertips of my other hand trailed around her stomach. My hand kept creeping up as I rubbed, until I was sliding my fingers up her sternum slowly and back down. Her breasts were too small to create any kind of cleavage, but the edges of my fingers rubbed the slight extra softness that marked their sides. She was relaxing again under my attentions, to the point where she even tipped her head back, exposing her neck. It was unconscious, I was sure, but I took the invitation anyway.

12