Writing the Story

I still felt a sort of embarrassment remembering the first time Alex had seen me naked. It was far more awkward than I'd imagined, partly because I was kneeling at attention while Alex looked me over, and partly because Alex couldn't stop laughing.

I still recalled vividly the frightening feeling of Alex slipping the chastity device over my cock, then locking it in place, knowing that only she had the key.

It still surprised me how I could feel even more naked wearing the slave skirt than when I'm actually naked.

I was so hopeful, lying naked on the table. I needed this so bad. Alex had hinted, when she'd given me my orders, that it might be today.

"If I'm in a good mood, you might squirt tomorrow."

It had been so long. Seven full weeks. I'd never imagined how hard this would be. Over the summer, I'd worn a couple of the chastity devices for 3 days each, and it had been torture, even for that long. I'd thought having Alex directly in control would make it easier. I can't imagine why I thought so. It made it so much worse. Being in her presence every day made me so damn horny, made me want it so bad, but she hadn't yet allowed it. My god, it was every kind of awful.

What would it be like? How would she let me do it? I remembered one of Alex's journal entries. She never described in specifics the professor having an orgasm, but she hinted at the student's philosophy.

"She assured her professor that he would never experience an orgasm again that could in any way be thought of as 'normal.' She was in charge, and it was her responsibility to make sure he always felt, even in his pleasure, the humiliation of being owned by his student. She promised him that any time she allowed sexual pleasure, it would always be weird and embarrassing."

Weird. Embarrassing. I wondered what Alex had in mind.

The door opened behind me. Oh my fucking god. I sure hoped this was Alex. I mean, her boyfriend hung out here all the time. Can you even imagine Travis walking in on me lying naked on the kitchen table. It'd be mortifying. I held my breath.

A long moment later, Alex appeared beside the table. She looked breathtaking. Wearing a yellow hoodie, she smiled down at me, a big, beautiful smile, then laughed.

"Ohmygod, look at YOU, slaveboy."

"Hello, Miss Alex."

"You know this will be nothing like before, right. Those days are over for you. I mean, like, it's gonna be...just different."

"I understand, Miss Alex."

"OK then. Let's get you secured in place."

Alex walked to a kitchen droor, and pulled out a roll of plastic cling wrap. Smoothing the end of the roll against the edge of the table near my side, she guided it over my body. Plastic wrap covered my pelvis, just above my enclosed cock. Alex continued weapping, passing the plastic wrap under the table, then over me again. Around and around, Alex wrapped my midsection to the table with cling wrap. My arms were pinned to my side with my fists still balled beneath my ass. My pelvis and abdomen were covered in clear stretchy plastic. Finally, Alex tore off the end of the strip and smoothed it against the plastic covering me.

"Good. Now spread your legs."

I wondered what this was all about.

"Yes, Miss Alex."

Keeping my fists under my ass, I started spreading my legs, until my dangling feet were slightly farther apart than shoulder width. My knees slid around the curved end of the table. Alex grabbed the insides of both my upper thighs, then gave the left one a very hard smack. I winced, gasping out loud.

"Seriously, slaveboy? Wider than that. I mean, come on. As wide as you can spread 'em."

"Yes, Miss Alex."

I was surprised at the whine in my voice. My thigh hurt, but the real issue was Alex's disappointment in me. It had shocked me just how ashamed I felt, a deep, aching sorrow, any time I didn't meet Alex's expectations. As soon as I'd kissed her foot that day in my office, as soon as all this had become explicit, made real, a deep-seated terror of letting Alex down had taken hold. It was one of the most surprising parts of this new life.

I spread my legs wider, then wider, a cramping feeling taking hold in my upper thighs as soon as my legs felt as if they were nearly perpendicular to my trunk. I strained to hold them there, thigh muscles aching as I teetered on the verge of muscle spasms. My legs hung off the sides of the table, and its edge now pressed into the back of my mid-thigh. I took a deep breath.

Alex let go of my thighs, then walked across the room. She returned carrying a little combination safe, the device that held the key to my chastity cage. Alex pressed six digits, and opened the door. She dangled the key in front of my face, then pressed it against my lips. Taking the hint, I kissed it. Alex laughed.

"Oh god slaveboy!"

Alex took my cock cage in her hand. God it felt exciting, even though I could feel nothing through the hard plexiglass. Jinglng the key, she looked straight down at my face.

"Look straight up at the ceiling, and nowhere else, Chris. Does this penis belong to you?"

"No, Miss Alex."

"No it doesn't. Who owns it?"

"You own it, Miss Alex."

"Good boy. Are you ever allowed to see it outside of its tube?"

"No Miss Alex, I'm not."

"No you're not. That's right. So no peeking."

I promised myself I'd keep my gaze facing upward. I wanted no part of being disobedient. I remembered the single time Alex had spanked me. Yes, it had been excruciating, but I'd continued crying long after the pain subsided to something bearable. I'd sobbed all night. The thought that I'd let Alex down, that I'd disobeyed her, that I was a bad slave, it was unbearable. It felt shameful.

The fact wasn't lost on me that I was naked, on a table, legs spread wide, being ordered around and humiliated by this girl. It was weird, and yes, it was sort of embarrassing, and if I thought about it too long a pervasive sense of humiliation set in. But deep down, I wasn't ashamed to be exactly where I was, experiencing Alex's degrading control over me. What brought me a sense of shame was not being the best slave for her I could possibly be.

I felt Alex's hand turning the key in the lock, springing it open, then sliding the clear tube off my cock. Oh god this felt weird. My cock was exposed, free for the first time in all these weeks, the first time since Alex had slid that tube over it and locked it in place. It seemed like it didn't know what to do. Excited as I was, my cock just hung there, mostly limp. I groaned in pain as Alex fitfully worked the ring it had attached to off of me, out from behind my cock and balls.

I took a very deep breath. I heard a clack as Alex set the cock cage down on the end of the table, near where my knees had been before I'd spead them. Suddenly, Alex appeared beside me, on my left. With her right hand, she flipped my cock up and over so that it was pointed toward my face, hanging over my plastic-wrap-covered pelvis. The sight of her beautiful face, and the feeling of her soft hand, fleetingly on my dick, did something to me. I inhaled sharply, and felt my cock grow into a full erection, its first in weeks. It felt so odd. My dick just kept growing, rather than being stopped suddenly by its enclosure. Oh my fucking god it felt nice.

Alex smiled at me. Reaching down with her left hand, she grabbed the center of my exposed ass. Spreading my cheeks with her thumb and forefinger on one side, her ring and pinky finger on the other side, Alex pressed her left middle finger between my ass cheeks, all the way up against my asshole, where she let the tip of it linger.

"Ready, slaveboy?"

"Miss Alex?"

I could hear a note of panic in my voice.

"It's time."

Alex pressed her middle finger harder, and I felt it penetrate my asshole, up to her first knuckle. I gasped. She paused, briefly, then pushed harder, firmer, penetrating me even deeper. I yelped as her unlubricated bare finger started hurting, just a bit. She wiggled it a little, then pressed further, then even further. My god this felt weird, and sort of awful, and totally degrading. I whined a bit more.

"Quiet!"

"Yes, Miss Alex."

She slowly worked her middle finger in a little further, then a little more, sometimes retracting it then plunging deeper, sometimes flexing or wiggling it slightly as she forced it in, until Alex's left middle finger was buried all the way in my ass.

Oh my god, the pressure. I just couldn't get used to it. The pain was mostly subsiding but there was this weird pressure that my ass didn't know what to do with. I'd never had anything up my asshole before. It just - I kept feeing my muscles contract around Alex's finger, squeezing it, then trying to relax, then squezing again. It felt beyond invasive. Alex smiled at me and brushed her dark hair from her face with her right hand.

It wasn't like her hands were small, I thought, as I watched her right hand near her face. Alex was tall, and strong, and sort of athletic, and her fingers, they weren't huge but they weren't exactly dainty either, they were a little thick, at least for a woman. At least her nails were cut short.

"So Chris. Get used to this. Any time the penis is ever out of its cage, my finger will be up your ass. Always. I mean obviously."

I wondered what was so obvious about this rule. Nevertheless, I was starting to get used to the feeling, humiliating as it was.

"Ok then. Now this is what happens for good little slaveboys whenever I decide to be nice."

Alex held out her right hand, flat, palm down. She let it approach my throbbing erect cock, and I gasped as I sensed her hand so close to it, so near. I was ready, despite the weird unpleasant feeling of Alex's finger up my ass. I was ready to be pleasured. My dick felt like it was sticking up and toward me at some sort of angle. I was waiting for the feeling of Alex's soft hand, waiting and ready.

A second later, the pad of Alex's right middle finger rested on the facing-up underside of my cock, just below the head. She pushed it down, just slightly, so that it was parallel with my body. I looked straight up, not daring to look at it, waiting for more, waiting to be stroked. Another second, then a few more, and still, I could only feel the pad at the end of one of Alex's fingers, just resting, unmoving, on my cock.

Alex smiled at me.

"Is this nice?"

"Y-yes, Miss Alex."

"Good."

"Is this - is this all, Miss Alex?"

"Shhhh. We'll be waiting here awhile."

"Oh. How long, Miss Alex?"

"Until something happens."

Oh my god this was bizarre. The pad of Alex's middle finger felt nice just under the head of my cock, it felt amazing, but it made me want so much more. I tried to move my body, to stroke along Alex's finger, but I was held down by the plastic wrap, and when I managed to move just a little bit, Alex just moved her finger to compensate, keeping it exactly on the same spot. Oh fuck this was frustrating.

I needed some sort of friction. I absolutely needed Alex to grip my cock and stroke it, or at least rub it. I gasped, then swallowed. This felt all kinds of wrong. Alex's finger remained just resting lightly on the same spot below my glans.

"M-m-miss Alll-l-lex? Are you going to... I mean am I allowed to feel you stroke it, Miss Alex?"

She moved her face so that it was directly over mine, and smiled down at me. Alex's hair hung partly in her face.

"No, Chris." She smiled again, sweetly. "No. You're not allowed to feel that. You gave that up when you became a slave."

"B-b-but..."

"Shhhh. Just relax. This is going to take a long time. Don't try to rush it."

Alex leaned in closer, her pretty face just inches from mine. As she did, she gripped my ass cheeks even tighter in her grasp, and pressed her middle finger even harder up my butt. I winced. Alex spoke very softly.

"I want you to enjoy this, slaveboy. I really do. You can learn to like this."

I could feel her breath on my lips. Alex stood up straighter, leaving me to deal with this odd, infuriating sensation.

Queasy. The word that came to mind was queasy. The feeling of being slightly nauseous, just a little bit sick to your stomach, that's how this felt. But in my cock. In the base of it, and just below the base of it, back further somehow, and in my balls, and even, somehow, in my pelvis and the inner upper thighs, and in my perineum. All of these parts felt sick with sensation, felt more noticeable than they ever had. Every impulse told me to stroke, to rub, to plunge my dick into something or against something. Oh my god. Oh holy fucking fuck. I noticed my breathing become shaky. A very slight stinging sensation spread up the length of my shaft.

I closed my eyes. Alex applied just enough pressure that her finger was very very noticeable on that most sensitive spot, but no more. It just stayed there, and I absorbed the feeings, tried to breathe, and just deal with this. My muscles contracted again around Alex's finger, then spasmed a little as they tried to relax.

I opened my eyes and looked slightly to the side at Alex, her beautiful face just watching me. This also seemed wrong. Normally, I knew better than to ever keep her waiting. I waited for Alex, not the other way around. Her time is more important than my time. It had been drilled into me. The fact that Alex was spending so much of her own time just giving me this experience, it made it seem so much more valuable. It was expensive, so to speak. And yet it was difficult to learn to enjoy it. The sensation was the height of frustration.

I waited longer and longer, just dealing with this whole experience, wondering how long it had been. An hour? Probably not, but it seemed like it. The feeling didn't let up. It just got weirder, more frustrating. The stinging in my cock intensified. I glanced at Alex, and again closed my eyes.

Suddenly, the door opened. The amorphous, free floating humiliation I'd been feeling suddenly sharpened into an acute sense of exposure, of genuine embarrassment. Oh my god.

"Hi Travis!" Alex spoke up, brightly.

"Oh my fucking god."

Hearing the boyfriend's voice sent my embarrasment into overdrive.

"My slave is getting his little treat."

"Yeah, I mean, good for him, I guess."

"It's gonna take awhile. You're welcome to stay and watch if you want. Or, you know, this might be a good time to get something else done."

"Yeah, I'll be at the gym for awhile."

"See ya! Love you!"

"Love you."

I kept my eyes closed for a long time. Shit that had been awkward. Oh god. Eventually I opened my eyes again and looked up at Alex looking down at me. The frustrating weirdness in my cock, my balls, my ass intensified. The queasy, edge-of-frustration lost sensation was back and it was growing. My urethra stung worse than ever.

Alex leaned her head to the left and smiled. She shook her shoulders a little. God damn she was gorgeous. Animated as her face was, her left middle finger was rock solid and still inside my ass. Her right middle finger was perfectly unmoving on the same spot on my cock. Oh god. I tried, involuntarily, pushing my body up against her finger, but she lifted it just slightly, compensating, keeping the pressure the same.

I took a very deep breath and let it out in shallow, ragged little pants. I bit both my lips. Oh my word this was awful, but somehow sort of wonderful, the only sexual sensation I'd been allowed since that fateful afternoon, and my god it was driving me insane.

I felt a chill across my entire naked body. I shivered a little. Still, I waited. My cock, rock hard erect and held motionless by Alex's single middle finger, suddenly twitched, just a little, almost imperceptibly. Immediately, Alex lifted her finger, letting my cock spring upward just a bit. It trembled a little, then settled down. The stinging was even worse now. It felt as if my cock was full, my urethra irritated by what it couldn't spasm out.

I felt painfully aware all over again of Alex's finger up my ass. Oh so fucking weird. She flexed it just a bit, I felt it wiggle, and I closed my eyes and sighed. My cock was still again, firm and motionless, and Alex again let her middle finger descend, resting on the exact same spot just below the head, and pressed down slightly. Again, we waited.

Every part of my body between my thighs and my abdomen tingled in awkward suspension. I could feel my soles, hanging free off the sides of the table, becoming sweaty. My balled fists, trapped beneath my ass, sweated as well. I took a very deep breath again, let it out slowly, and inhaled once more. Alex smiled at me.

"You're being a very good boy."

"It's so weird, Miss Alex, so frustrating."

"I know, slaveboy. I know."

It must be getting dark outside, I thought. I was opening my eyes between bouts of squeezing them shut. Everything tingled in frustrated anticipation. I bit my lips, hard. I waited. I squeezed my fists tighter. I waited.

Suddenly, a little spasm. My cock twitched, just a tiny bit.

Just like before, Alex immediately lifted her finger, leaving my cock untouched, allowing it to spring back up. This time, it was more twitchy. It seemed to move on its own, spasming and twitching against nothing, Alex letting her finger hover inches above it, and the urge, the need, the instinct to stroke against something, in something, was just too much, and I groaned pathetically out loud, then groaned again, and my cock kept up its sort of twitching, something was happening, something wrong, the feeling of having to cum, to spurt, to ejaculate overwhelming everything, and unable to do anything about it, the stinging unbearable now, and suddenly, I could distinctly feel just a little dribble of semen dripping out of my cock, just a thin thread of it, it had already been draining, pooling on the cling wrap on my abdomen, then I felt a little pulse, a little twitching, and a sort of glob of semen kind of oozed out of the penis, I could tell, though I wasn't allowed to look, and everything still felt so awful and frustrating and confusing, somehow better, somehow a relief, but in some way much much worse. My ass contracted hard around Alex's finger and I was somehow thankful for it there all of a sudden. The oozing kept up. The penis just sort of slowly drained, almost, leaving me with a feeling of all kinds of semen still in there somewhere, in my balls, in my cock, waiting to come out but with no rubbing or stroking or thrusting to make it come out, and I groaned loudly, and Alex laughed.

"Oh my god your face!"

Alex laughed again. I was too lost, too trapped in this strangely trippy frustration, this not-even-close-to-orgasmic feeling still throbbing in waves through my ass, my cock, my gut, my thighs. Oh wow. Oh holy hell this was just - I couldn't even begin to describe it.

"So Chris. You're still gonna be here awhile. Until your cock settles down, there's going to be absolutely no touching it. I can't risk letting you, you know, orgasm. But while we wait, there's something we need to take care of, something you have to do every time I let you dribble."

The ache in my thighs suddenly became noticeable again. I hoped I wouldn't start cramping. This was so fucking weird. I'd released, sort of, kind of, but not really, not exactly, and the absence of anything even close to orgasmic left me in a very weird, sort of relieved but still very submissive funk. I tried to deal with all of these thoughts and emotions as Alex pressed the middle finger of her right hand against my pelvis, against the plastic cling wrap, and wiped just a little of my semen from it. She held it up to my lips.

"Open up, slaveboy. If you release, you swallow. No exceptions."

Oh Christ. I made a weird face. I suddenly remembered a subplot in one of Alex's parts of the stories in which the professor had to swallow his cum any time he was allowed to spurt. I hadn't thought much about it. Oh my god. The stuff smelled so bad.