Annie Brings a Friend

"Loud enough so I can hear," I coaxed her.

In the silence I could hear the soft click of Annie's lips opening. But she didn't, or couldn't, speak.

"If you don't tell him I'll make you stand up and show him," I prodded.

"I'm not even sure that's worse." said Annie. But she didn't move to stand. Instead she sucked in a big slow breath through her nose. "She's got her fingers in my ass," she finally said in one quick exhale.

"Was that so hard?" I teased. Annie didn't answer, but the brilliant red flush that lit up the back of her neck and ears was evidence enough.

I watched with interest as Jasper tried to hide his surprise. He did an alright job, but a slight flaring of his nose and bounce of his eyelids gave away that things were moving faster than he'd expected.

"Just one finger." I clarified, letting Jasper see my evil smile. "Got to work her up to the second one."

The process of loosening Annie was one I quite enjoyed. Slow and stately I pushed into her and then pulled out, applying a rubbing sideways pressure against her stubborn ring as I did so. The key with Annie's ass, I had learned, was to keep the pace consistent. Like my finger was a piston, an inevitable machine that could not be fought, only succumbed to.

The three of us stayed in silence for a few minutes. The barely audible background of my wet ministrations and Annie's labored breathing no doubt painting wild pictures in Jasper's mind.

Then, right as I was getting ready to chide her for fighting me, I felt Annie's ring relax another iota. Which was all I needed to poke another fingertip past. Annie groaned a long combination of defeat and discomfort the whole way as I celebrated my victory by pushing into the second knuckle.

"That sounded like two fingers," Jasper said. Prompting a new groan from Annie.

With two of my fingers inside of her now. Annie was starting to struggle. She breathed out in long thin streams through tight lips. And all the while her hips wriggled, trying to escape the insistent fucking. But there was no escape for her. Not with Jasper's arms around her. In fact, I was interested to see the muscles in Jasper's forearms casually tight. He seemed to be doing his best to hold her in place.

"How does she feel squirming against you there Jasper?" I asked him.

Jasper really seemed to be relaxing into the experience now. I wondered if the wine or the arousal was to blame. "It's pretty great actually," he admitted.

Annie and Jasper were pressed too close together for me to really see what was going on between them. But the mental image of Annie's sex grinding against the bulge in Jasper's jeans was driving me wild. It was getting hard to focus on keeping a steady rhythm.

"Should I fuck her harder then? Really make her move for you?" I asked.

"She seems like she's barely taking it as it is," Jasper started kindly. But he quickly changed his tune when I shot him a nasty look over Annie's shoulder. "Well, maybe you could turn it up one more gear."

"You guys suck," came the whimper from behind Annie's mess of hair.

As Jasper laughed I turned it up at least two gears. Before, with a single finger, I had spread Annie with patience and a smooth consistent flow. But now that I wasn't trying to sneak any more fingers into her, I no longer required Annie's cooperation. I started to vary my tempo, pulling back sharply until I was almost out of her. This enticed Annie's sphincter to clench of its own volition, trying to shut the open door. But the tips of my fingers would always be there, to keep her open.

I savored the sensation each time I rebuffed Annie's ring, like a grasping hand it squeezed me so hard it almost hurt. But tricking Annie's body into a battle she couldn't win was only half of the torment I had for her. Because every time I felt her trying to push me out I would also counter by pushing back in. Bullying my way into Annie at the same moment her spasming muscles were fighting me.

Each time I pressed into her this procedure produced from Annie a whimpering moan. It was the undignified sound of an animal in distress and, to me, it was the most beautiful sound in the world. With Jasper holding her in place I played Annie like an instrument. I varied my tempo, my angle, my depth, determined to produce every possible variation of her sound. Like a conductor I stripped away any notes I recognized as Annie's conscious affectations; until she sang along with me raw and without decorum, unable even to care what Jasper might think. The poor girl's arms wrapped tight around his neck, her fingers tying themselves into his short blond hair as she tried, on instinct, to curl herself into a ball around him.

I knew in this moment that I had irrevocably changed Annie and Jasper's friendship. Had I taken a different course, maybe just let Jasper see his naked friend endure a spanking, forced Annie to masturbate for him, or any number of other options I had considered, their friendship might have survived in its current form. Sure, Annie would struggle to look him in the eyes at first. But over time, their night of naughty fun would have become a wonderful secret they shared. An inside joke. A wink across the table.

But now Annie pressed herself into Jasper, practically sobbing her suffering into the crook of his neck. And I knew I had revealed to Jasper a part of Annie that could not be reconciled with the image of a bubbly coed looking for some fun. From this point on when he looked at her, this is the Annie he would see. And for her part, Annie would know the same. She'd see the distant stare when he looked at her, and know he was looking back and through her, at the girl who was broken in his arms, but never begged for it to stop.

-----

I let Annie down gently. First, I stopped fighting her body's natural rhythms and instead tried my best to sync my penetrations with them. Then, gradually, I slowed my pace until we were still. The only movement was the rise and fall of Annie's back as if trying to catch her breath after a long run.

Surprisingly, it was Annie who spoke first. "Hey Jasper. It's kind of wet."

Silence.

"Did you cum?" Annie asked.

"Yeah. Sorry." Jasper said. Very much sounding like he'd been caught stealing cookies.

I knew it was wrong to delight in the power I'd chosen to wield over Annie and Jasper's relationship. But I found that I couldn't help myself but to pile on, "How does that feel Annie, knowing your friend was getting off watching you take a punishment?"

Now it was Jasper's turn to blush. Though his tan did good work to hide it.

"I dunno. It's fine I guess." said Annie in a tone that made it clear she wasn't particularly interested in engaging with the idea right now.

Any guilt I was feeling instantly evaporated. Annie's dissociation annoyed me. I wondered if later a clearer headed Annie would realize that she'd just earned herself one more punishment.

I slid my hand around Annie's hip, finding the space where her and Jasper pressed together. Then I explored downward. Jasper watched me curiously as I found the belt loop of his jeans before probing further where, indeed, the denim had taken on a damp, tacky, feeling.

"Messy boy." I teased Jasper. Enjoying that he seemed unable to meet my eyes now. "But don't worry. I have a solution."

I slid my hand back up by Jasper's belt loop. But instead of fiddling with his zipper, as his shifting hips suggested he expected, I instead flipped my hand around and started pressing against Annie's lower belly. When she tried to pull away, I curled my fingers in her asshole, holding her in place.

"Professor?" Annie asked. Understanding what I was after but still shocked by it.

"Tell him." was all I had to say to her.

When Annie didn't immediately comply, Jasper spoke up. "Tell me what?"

Annie sighed like a petulant child who just wanted to be left alone. "She's trying to get me to pee on you."

Sometimes, when she was really itching for a punishment, Annie gave me attitude to goad me into it. But in this instance, I assumed her bratty behavior stemmed more from emotional exhaustion. Not that it mattered, my response would be the same.

I took my hand away from kneading Annie's bladder and bundled up her long hair. With the makeshift ponytail I pulled her back towards me until she was only connected to Jasper by her hips, and her hands around the back of his neck. "Not trying. Doing," I growled in her ear. Making a real show of it for Jasper's benefit. "Now pee, or I'll fuck that poor little ass of yours again."

"Yes Professor," Annie said meekly.

"Good girl. And you two look each other in the eyes. I want you to see his reaction when you go."

Apparently cowed by my sudden strictness, my two victims locked eyes. Annie's nose wrinkled in an expression I recognized as concentration. So I resolved to give her a little time before making good on my threat.

Eventually Annie said, "I can't go with your fingers in me." Which was promptly followed by a little squeak as said fingers popped out of her.

Jasper watched with obvious bemusement as Annie's face contorted through a number of poses on her way to convincing her bladder into action. A few times I had to take her head in my hands and remind her to keep eye contact with him.

When she finally started to go I didn't even hear it. But I knew it was happening because Jasper's eyebrows jumped in surprise. To his credit, he recovered gracefully and tried to give Annie a reassuring smile. But by that point Annie had completely failed the test and her eyes were scrunched so tight that I wasn't sure if the vibrant redness was a blush, or if she was just losing circulation.

"Oh god." Annie whimpered her embarrassment without opening her eyes when a rhythmic dripping sound started up.

With genuine curiosity I asked, "How are you doing Jasper?"

"Pretty warm now," he quipped.

"You guys are the worst," Annie said. Finally letting go of Jasper so she could hide her face in her hands.

"Oh hush," I chided her. But it was clear that Annie had reached her tolerance for this whole ordeal. I gave her a little slap on her ass. "Go get yourself cleaned up. Don't dawdle."

Annie started to stand. For a moment it looked like her modesty concerns from earlier had been forgotten, or maybe rendered moot by recent activities. But before she swung her legs for the dismount she swiftly covered Jasper's eyes with her palms. Jasper just stuck his tongue out at her, but I caught him eyeing her perky butt as it fled the room.

Jasper looked down at the dark blue sodden mess that was his lower half. Gingerly he shifted his weight to one side. For one horrific moment I thought he was fixing to fart. Which would have really ruined the pleasant image I was building of him. But, I was eternally grateful to see, he was just fishing his cell phone out of a damp pocket. He pressed a button on the side and the screen blinked to life.

"That's good," he said brightly. "So, did I pass the test?"

From his sitting position Jasper wasn't even that much shorter than me. But I still got a thrill seeing those bright green eyes shining up at me. The urge to take Annie's vacant seat, albeit with a much more commanding demeanor, almost overwhelmed me. But the thought of all that pee, now cooling in the open air, was the metaphorical bucket of ice water I needed to play the long game.

"This wasn't a test. But you were wonderful anyway my dear. Now I need to take care of Annie though. Which means it's time for you to go."

"You're not going to offer me a clean pair of pants, are you?" Jasper said ruefully.

I winked at him. "You do catch on fast."

-----

Just outside my door, his jeans looking much baggier than when he arrived in them, Jasper turned back toward me. "So, if I want to get in touch, do I talk to Annie? Or can I call you?"

I tried to hide my smile. I didn't want to seem disinterested. But it wouldn't do to come off overeager either. "Give yourself a few days to think about it. But then, if you want, my office hours are easy to find. Goodnight love." I let the door swing closed and then turned to follow the wet trail back to my dining room.

Once again I rounded the corner from the kitchen to the dining room to find Annie kneeling naked on the wood floor. But a few departures from the earlier scene saved me from succumbing to any déjà vu. For one, Annie wasn't really kneeling in the middle of the room this time. That spot was taken up by a slowly widening puddle, which she'd given a wide berth. Annie herself had also been transformed over the course of the night. Her hair was mussed, the little makeup she wore had been rubbed off one side of her face, and though I couldn't see any signs of tears, her cheeks had a tell tale puff to them. She even knelt differently; slouched, tired.

Careful to avoid the puddle I crouched in front of my bedraggled submissive. Taking her by the back of the neck I pulled her forward, cradling her against my chest. "How are you doing sweetie?" I cooed.

"Alright I think. Still processing," Annie said.

"So you had fun?" I pressed, knowing the answer.

"No, it was awful," sniffed Annie.

"So I did good then?"

Annie leaned into me a little more and wrapped me in a hug. "You always do good, Professor."

It was kind of an uncomfortable position we were in. But it felt right to just hold Annie like that until she spoke again.

"I think Jasper had fun." she mused.

"He better have. You literally made him cream his pants!" I said, prompting a little giggle from Annie.

"I guess that was kind of my fault wasn't it?"

"It sure was. Were you doing it on purpose?"

I was amused that Annie seemed to have to give the question some real thought. "I don't think so? At first I was, you know, trying to get a little something for me. But that stupid zipper really hurt!"

I laughed and tousled Annie's already ruined hair.

"So are you going to play with him again?" Annie asked. She was trying to sound nonchalant. But I could tell she was invested in the answer.

"Aw sweetie. I would like to. But only if you give it the go ahead." I said.

Annie pulled back just enough so that she could look up at me. Her deep dark eyes flickered their way about my face, searching for something. "Really? I thought you'd just decide."

"I did decide. I decided to ask you. Don't get used to it though." I tried to sound stern, suddenly worried my gesture of goodwill might somehow weaken my power over Annie. But it was hard to look mean with those loving eyes pouring themselves into me.

"So, should we see him again?" I prompted.

Annie spun herself around, and my body moved automatically to take her into my lap. "It's going to be weird tomorrow." she mused. "With you. It's like I come here and I'm a different person. I don't have to think about it when I'm just living my life. Well, unless I've had a spanking recently. But I've got a class with Jasper tomorrow. It's going to be weird. I don't know if I want that."

A sudden urge to apologize bubbled up from within me. But like bile I choked it down.

"But I guess that can't be helped now." Annie continued. "And I know you want him. So I guess I'm OK with it."

I kissed the top of her head. Pressed my lips to her scalp and squeezed her while I held them there.

"Will we play together? Or will you play with him alone?" Annie wanted to know.

"I haven't decided." I answered honestly.

"Oh. I don't get a say in that?"

"You, my dear. Don't get a say in anything else for at least the next six months."

Annie nodded. Like a child absorbing some new piece of information about the world. "Hey Professor," she said.

"Yes?"

"We should clean this up before it stains your floor."