Man of Integrity

Butterfly kisses on her neck brought the tension back, but she didn't clamp her neck down or shrink away. I looked over to where I'd put my phone down on the bed and tapped one of the saved phrases.

"This can feel good if you relax and let it."

I felt her relax slightly. Then as my kisses on her neck got longer and more intentional, she relaxed some more. My roving hand "missed" her cleavage more and started rubbing around her breast, finding the softer, more pliable rises around the edges.

Rory's mouth opened. Her breathing got deeper and a bit faster.

There was no guarantee how sensitive her breasts would be, but a few studies I knew of said that smaller breasts tended to be more sensitive. There was also the mental aspect to it; so many of the ignorant boys her age probably ignored or even put down the small rises on her chest. If she'd had sex, the guys most likely skipped right over them; what was the point for them if there wasn't enough to grip onto or slide their cock between?

I began to worship them. I took the risk of moving faster, sliding my hands down so they traced around the edges of her breasts. My mouth moved down her collarbone and sternum. We both knew where it was going. I felt her tense up again as my mouth got closer, but I let myself hope it might be anticipation rather than fear.

By now Rory's nipples were hard points on the small cones and my fingers had brushed over the rubbery nubs a few times. When I licked around one I got my first gasp from her. I got another when I moved to the other nub. When I took one between my lips and sucked, she actually moaned.

I spent a long time moving back and forth, massaging with my hand where my mouth wasn't present. Rory responded faster and more intensely than she probably meant to, but I could tell I was getting through to her. First her clenched legs relaxed, then they actually opened a bit. Her back arched to push her tits out so I had better access. Then she scooted forward on the bed and her legs spread more. Her hips shifted in movements that might actually be thrusting. Then, finally, one of her dainty teenage hands came up and pressed my head against her chest.

She'd let out moans regularly by then. Now she said her first word in passion.

"Please."

I didn't know what she was asking for, but I could guess. I'd kept one hand on her hip as I rubbed with the other. I moved it around, over her thigh, and down between her legs. I didn't move to slip beneath her panties yet, but when I got to the gusset there was undeniable heat, and a hint of wetness.

I sucked hard on her nipple as I let my hand drift closer and make actual contact with Rory down there. Again, her response might have been all but unconscious, but she definitely pressed against my hand and ground her crotch on the knuckle of my thumb I positioned for her benefit. Soon my little teenage student had a hand on my head, pressing me into her sensitive tit-flesh while she thrust her crotch into my hand. For the moment, it seemed, any hesitation, nervousness, or questions were abandoned in the name of chasing her orgasm.

The chase ended suddenly and intensely, surprising both of us, I think. Her arms suddenly wrapped around my head hard enough that I had to turn it or get my nose crushed. I could feel her legs trembling and quivering on either side of me, and my thumb got a lot damper than it had been even after her rubbing.

"Oh god, oh fuck it's....fuck...why did that feel so good?" she asked.

The first hurdle was crossed. Now to see how she reacted. In my experience one of three things were about to happen. Option one was her getting overwhelmed in shame, running away, and me having to do a bunch of quick cleanup. The next possibility was that she'd remain curious, encouraged by her first pleasant orgasm, and be willing to keep experimenting. The third possibility, but very unlikely, was that she was a closet nymphomaniac and I'd just unleashed her.

When she let go of my head I got my phone and quickly typed out a response to her question.

"The mystery? The little bit of fear? Adrenaline can make sex even better; that's why so many people try things like doing it in public."

"That felt good. I didn't even want it to at first but..." Rory trailed off. She was probably remembering all the details of the little arrangement.

"You still want to fuck my ass don't you?" she asked, quieter.

The fact that she was more vulgar about it actually encouraged me; it suggested she was more at ease.

"Don't worry about that right now," I said through her phone, "Would you like to feel good again?"

"What would I have to do?" she asked.

"Let me take off your panties."

She pulled her legs together again, but only for a moment. She sat still for a while afterward, then she nodded.

I'd stayed kneeling, but now I pushed myself upright so I could reach her hips. I rubbed my hands over her tits again gently to remind her of the pleasure she'd just experienced. That helped relax her more.

When I slid my hands down through the elastic of her panties and pulled, she wriggled to help me get them free. Another positive sign.

A waft of girl sex aroma came out as the panties moved away, and her bald slid came into view. It was small and tight, barely parted to reveal the pink inner labia. I bet before she was aroused it closed like a mouth, letting nothing peek out. I admired the sight for a moment, then sent another message.

"Roll over onto your front, but up on your knees."

I gave subtle pushes with my hands to help her along, but after a few seconds I had to just sit back and admire my favorite view in the world; a young, thin girl, bent over and displaying herself, her pussy wet with arousal. Her thin ass formed two rounded peaks as the flesh was pulled tight over the bones, and her build meant there wasn't enough flesh to hide anything. Instead a sloping valley formed, with her crinkled brown starfish down at the bottom of it, sitting just above the short expanse of skin that led down to her pussy. Every time I saw this view I had to resist the urge to take a picture, but it would take too long and create another piece of incriminating evidence. After today, I'd have to be content with my memory.

Today, though, I had the genuine article in front of me.

I started in the middle of her thighs, planting kisses on them and moving slowly upward. My palms settled on those bony peaks at the top of her legs, my fingers gathering the flesh that formed her rounded ass whenever she stood. I felt her tense up again as I gripped her, but I didn't care anymore; I knew I had her. Once they let me get their panties off it was all but a sure thing.

Her breathing was hot and heavy as my mouth got closer and closer to her sex. Assuming she'd been telling the truth about not being a virgin, I was willing to bet money I'd already spent more time on foreplay and her pleasure than any of her other lovers. When you add in how much more aware the adrenaline made her from the anticipation and anxiety of the scenario, and she was feeling everything twice as much.

Case in point, I blew air across her pussy and she shivered with a moan. I saw the little tunnel of her sex clench as I moved in. Soon my tongue trailed up and down the swollen lips of her pussy while my hands kept lovingly squeezing and kneading around my ultimate prize.

"Fuck...fuck...I've never..." Rory mumbled. I could only hear a few of the words, but the girl kept up a running commentary to herself as my tongue went deeper, splitting the labia around her tunnel and tasting the spicy nectar within. I probed in and around the hole for a while, tasting her love juice wherever I found it and feeling her muscles contract as I hit a sensitive spot. Eventually I felt more pressure as she pushed back against me. It pressed my nose into her ass and she flinched a bit when I touched her hole, but then she ignored it in the effort to get my tongue deeper.

Eventually she was almost fucking herself on my tongue. After letting her do that for a moment, I shifted down and quickly fluttered my tongue back and forth on her clit like a vibrator. A few seconds later she screamed.

Her pussy soaked itself in juice again, desperate to make itself ready for a penetration that would never come. Rory tried to curl up into a ball, but I held her there and used her orgasmic throes as a distraction.

My tongue pressed in and around her asshole, teasing the sensitive and unyielding muscle as I kept her cheeks spread. She only noticed after the aftershocks of her orgasm waned.

"What...fuck that feels...weird. Ohhhhhh."

The moan at the end came from my insertion of two fingers into her sopping wet pussy. The heat and the wetness was incredible, and she was tight enough that even two fingers was a snug fit. At that point she didn't care what I was doing to her ass or, if I was lucky, it was merging in with the pleasure of having her sex plundered by my digits.

Now she really did start fucking herself on me, rocking back and forth on my hand and slipping my fingers in and out. I didn't stop her; why would I? I did use the opportunity to press harder with my tongue, and in a short while the ring finally gave way. It wasn't on purpose from her point of view; I just took advantage when she relaxed from a frission of pleasure. But now that it was in there, my tongue wasn't coming out.

I licked and pressed against her ring, moving around like I was questing for hidden treasure in her anus. She slowed down her thrusting as she felt it, but I took up the slack on my end, moving my fingers in and out of her pussy to keep up the pleasure. I also upped the ante by curling them to find her G-spot, rubbing the soft ridges of that pleasure spot with each thrust in and out.

As much as I loved dining at that particular venue, I had another goal. With my unoccupied hand, I popped the top on some lube and coated the hand with it. I pulled back from my licking and watched the hole between her cheeks wink closed. Then I twisted around so I looked up at her pussy from below.

"Ohh what?" Rory moaned, sounding out of it. Sweat now mixed in with the aroma of her love juices.

I pulled down with my fingers and she willingly spread herself and lowered her pussy. I swiped at her clit with my tongue and she let out a deep, throaty moan as I gave the love button the attention it had no doubt been craving since that first orgasm.

After a few licks, I slipped a finger in her backdoor.

She pushed herself up on her hands immediately at the intrusion, but I kept up everything I'd been doing. Between prepping her with my tongue and the lube on the digit it slipped in very easily.

"Fuck...fuck, that...uggggh," Rory moaned out.

Like everything else I'd done, she gradually accepted it, more concerned about the pleasure from her pussy and my treatment there than she was about whatever she felt from her ass. If it had genuinely hurt she would have had a worse reaction. At worst, she probably just felt uncomfortable. At best, she was one of those women with a particularly sensitive ass, and the feelings from it merged with the other penetration.

My fingers felt clenching around them and Rory's moans got more frantic, her words less coherent. I'd only been with this girl a little while and already I was learning the signs of her impending cum. I teased her a bit, slowing my thrusts and licking, forcing her to ride the edge as much as I could. But she could still move, and soon she was nearly breaking my nose looking for the last little bit of stimulation. That also meant she was thrusting back on the finger in her ass, which was exactly what I wanted. Eventually when she pulled away, I moved two other fingers into position.

She speared her ass on three of my fingers and howled into the bed, but the tight, velvety grip on my fingers told me she was cumming. I kept pumping, my fingers forcing her to ride out the double penetration of her holes as they contributed to her third orgasm.

I slipped out from beneath her when it felt like her orgasm faded. I quickly looked and saw a bit of a gape in her asshole as my fingers withdrew. I dropped my pants and stood then. I adjusted the condom I'd slipped on before leaving the hotel room (I hadn't really gone soft in that time) and then coated it with lube. Then I grabbed my phone.

It was the one part of my hobby where I allowed myself to be unnecessarily selfish. I knew if I wanted, I could probably step forward and start sliding in and she wouldn't really stop me. But I wanted more.

"See? It can make you feel good," I sent through her phone.

"God...fuck...that was too much," Rory said.

"We still have the last step to go," I reminded her.

"Oh fuck," she said, but it wasn't totally fearful or angry. "What do I do?"

I smiled and asked for that little bit more.

"Ask me to do it," I sent.

"What?"

"Ask me to do it."

"Can't you just-"

"Ask me to do it."

There was a pause. It was definitely pushing her limits. A lot of girls with more experience, self-respect, or other options would tell me to go fuck myself. But Rory didn't have those, and I had a lot of faith in the sunk cost fallacy; she was in this deep, what was a little deeper?

After another moment's hesitation, she bent over and arched her back more.

"Please fuck my ass," she said.

I didn't wait. I moved forward and lined myself up. I also hit one of the stored messages.

"Push out as I'm going in."

It took two or three pushes, of course; it always did. A cock at your ass feels like a baseball bat, even though mine was average sized (and yes, I had tried it myself. With a dildo anyway. Not my thing. Yes I'm a hypocrite.)

Eventually the head popped through the ring. I kept a solid grip on Rory's hips as she yelped and moaned at the intrusion, then waited for her to get used to the pressure, the burn, and possibly the pleasure. I drizzled more lube on my cock.

When she seemed to get over the initial shock, I started thrusting. Short, shallow thrusts to work her open. She tensed and groaned, but at that point the clenching just helped my own sensations. Soon half my cock sawed in and out of her ass, the red ring gripping the pole tightly on its way out.

Rory let out more f-bombs than a Tarantino film as I sodomized her. Then I paused and reached over for my phone to hit another message.

"Rub yourself."

Her hand immediately shot back between her legs, and I saw her shoulder shake as she worked her soaked cunt with her fingers. The pleasure must have distracted her more, because soon I pushed forward and ended up feeling those wonderfully padded bones pushing against my hips. I was all the way in.

I took full advantage. I stopped caring if she liked it at that point and just ass fucked her. My hips slapped against her ass and my cock plowed into her anus. I didn't jackhammer thrust, but they were deep, powerful, and regular, just like I would do a girl if I was inside her sex. She grunted at each impact and from the slight brushing I felt against my balls her hand was a blur on her pussy.

The reality of these encounters is they were always too short. Spending the time eating the girl's pussy and ass, then working my way inside her, meant I was always too stimulated for more than a quick fuck once I was in her ass. Some of the girls probably thought it was a blessing.

I pressed myself deep against her, imagining I was pumping the cum from my balls deeply into her intestine even though it was all being caught by the condom. I felt her asshole twitch and I deluded myself that maybe she'd cum when I did.

I pulled out and admired the sight. Rory bent over on the bed, her ass gape closing and glistening with lube, her pussy inflamed and covered in juice, her hair splayed around, her body covered in sweat from the three orgasms she'd had and the ass fuck I'd just given her. I sent a last message to her phone.

"Prep for the competition tomorrow. Remember you're in, but you still have to win it with your project."

I actually sent the message as I headed out the door. I swiped the webcam from the room's desk when I left. In twenty seconds I was in the stairwell, but my eyes were on my phone. The last part of the virus on her phone let me remote activate the camera. It was pointing at the ceiling of course, but I heard her scramble off the bed and, soon after, the door latch. She wouldn't run out into the hall; she was still naked. But I knew she'd hoped to catch sight of me. She returned to the bed and I saw her face, un-goggled, come into view. Her eyes were red with tears and her hair plastered to her face from sweat. Then the feed cut as my virus self-deleted.

I sighed. It was the ultimate disappointment of these encounters. For all I knew I'd just awakened a newfound desire in Rory to take it up the ass. If I hung around long enough to get hard again, she might have let me properly sodomize her, maybe even with her on top, dropping down onto my cock as I cupped her ass.

Experience told me it wasn't worth it. If any of the girls got a newfound desire for anal out of this, they weren't likely to want to pursue it with me. The first few times I'd tried to linger after the deed, but it always ended with the girl even more scared, angry, or both; I told them I would fuck their ass, and I had. Deal done.

I was on the final judging committee, but I would only see Rory from a distance of a few dozen feet as she gave her final presentation. The only way I would see that ass again was contained in slacks or in my memories. All that was left between us was for me to go in and update her team's scores so she was seventh or sixth out of the fifteen finalists. It would give her a boost, but I was true to my word; they would have to win the final competition on the merits of their project.

I had integrity, after all.