The sadist and the sissy

I probably could’ve been in a better mood when I arrived at Sounder’s house and knocked on his door.

He opened it, purposely staying behind it, out of sight, as I walked in.  I figured he was wearing his lingerie, or maybe his wig, or something equally cute to surprise me.

When I saw him step out as he closed the door, I couldn’t stop the smile from spreading across my face as all the shit that had been clinging to me instantly just fell away.  I gasped, and I think I might have even squealed.  I know I squealed inside my head, I can’t remember if that was out loud or not.

He was fully dressed, head to toe, with his wig, makeup done, wearing one of his amazingly sexy outfits, a black blouse with incredibly sexy, figure-hugging, super-tight white jeans that hugged his butt in that seriously sexy way.  He was even wearing his adorable, strappy sandals.

I hurried to put my things down and turned back to him, holding my hands out to him.  “Come here, let me see you!”

I looked him up and down, appraising his makeup, and was wholly impressed.  “You look amazing!”

“I think it’s a disaster,” he replied.

“Why?”

“This took like two hours.”

I giggled (shut up, I can giggle and still be super severe and intimidating and all that).  “You’ll get faster with practice.”

And seriously, I felt like an idiot, I couldn’t look at him without smiling.  And it occurred to me that I didn’t care if I looked like an idiot.  Fucking hell, but he is one goddamn sexy sissy.

It didn’t take long for my lust to get the better of me, and I walked behind him, cupping his perfect, perky ass through those deliciously tight jeans and reaching further down, between his legs, to rub against the hole I was planning on annihilating later.

A moment later, I reached my hand down his pants, grabbing his ass and groping him like a horny teenage boy.  It didn’t take me long to get his pants undone and down around his ankles, along with the white, lacy panties he wore underneath.

I pressed the tip of a slick finger against him, then pushed it in, a chill going down my spine at the sound of his adorable little gasp at being penetrated.

Seriously, like holy fucking shit, this little girl is hot.

“Take your pants off,” I told him.  Then, after just a second’s hesitation, “The shirt and wig, too.”

Because as good as he looked with it on, I wanted to be rough with him, and didn’t want to mess it up, or have it get in my way.

Once he was naked, I stood behind him, grabbed him around his shoulders, and yanked him back against me, completely off balance, and the way he just yielded to it was even hotter.

For a moment, I kissed and teased his ear, then turned him, without letting him regain his balance, flipping him over and lowering him down to his hands and knees.  I kept it mostly mild, we were still in the living room, and he has windows.  But I couldn’t resist a little slap here, or a little spank there.

I had a specific plan for him, and due to the logistics of it, we decided that his downstairs bathroom would be the place for it.  I wasn’t going to do that quite yet, though, so we went to the downstairs guest room instead.

Once we were there, I buckled a sturdy leather collar around his neck, pulled out a new dildo and shoved it unceremoniously in his mouth, slapping him around a bit.

I kept it mild with the slapping though.  He doesn’t dislike being slapped (and was surprisingly eager and enthusiastic about it when I first broached the subject), but I have to be careful about leaving marks on his face, and he’s prone to migraines, and causing one from hitting him too hard wasn’t all that high on my list of things to do that night.

That’s one of those things we’ll have to be super careful, and super slow, about raising the intensity.  And since that wasn’t the primary focus of the night, I preferred to err on the side of caution.  We’ll work on figuring out how hard I can safely slap him soon, though.  Hitting him is ten kinds of fucking amazing.

And really, he was so fucking cute, gagging on the cock in his mouth, and choking when I shoved it in deep.

I was impressed, though.  I figured out that, when he’s given the chance to control it, he actually has some really good deepthroating skills.  There was one moment in particular when he, eager to please me, pushed forward hard against my hand, taking the cock as far as it would go, and holding it there, pushing even harder, until I felt that unique change in pressure as it slid far past the point that should’ve stimulated his gag reflex, and down his throat.

He pushed himself to take it farther, to keep it there longer, until, coughing and sputtering, he pulled back, lowering his head as he gagged.

In the next moment, he took a deep breath, lifting his head back up, his lips parted as he waited for me to push the cock back into his mouth.

He really is an excellent cocksucker when he’s given the freedom to do it on his own.  When I fuck his mouth, however, he has a little bit more trouble suppressing his gag reflex.

Which is something I’m going to have a ridiculous amount of fun breaking him of.  I want more than him sucking cock.  I want his face thoroughly and relentlessly fucked by men who will further degrade and objectify him, reducing him to nothing but a pair of holes to take their pleasure from.

Before long, his eyes started watering, smearing his makeup in that particular way that happens when women (or sissies) are made to choke on cock.  And it only made him hotter.

I was relentless with him, forcing it into his mouth, down his throat, grinning when his eyes watered and tears fell, his body convulsing as he tried hard not to throw up, and calmly and quietly enduring every slap that landed on his face.

He really is such a good boy, and he works so hard to please me.  A boy that good deserves a reward.

Finally, I released him, telling him “Stay,” tossing the dildo on the bed and rummaging through my bag again, looking for something specific.

One of my favorite toys to use on any boy is a long, slender prostate massager, a kind that’s surprisingly cheap and common to find literally anywhere, which makes how effective it is even more amazing.  Most people would say it’s the most basic kind of massager out there, but sometimes the most basic kind is the best kind.

I lubed it up and sat on the edge of the bed, while he knelt on all fours in front of me, his ass to me.

“This is a fantastic view,” I told him, sliding the massager smoothly into him, using the angled bulb at the end to put pressure on his prostate.

He gave a low, shuddering moan and eased back, urging the massager deeper into him.  I grinned.  My darling, eager slut.  He loves it deep, and hard, and fast.

I kept the pressure steady, thrusting it smoothly in and out of him, until his moans intensified and I knew he’d had his first orgasm.

Oh, one of many, I thought, grinning, as I kept the pressure up, fucking him through his orgasm.

The second (or maybe the third) orgasm, he fell forward, the massager momentarily falling out of him.  I didn’t hesitate, pushing it immediately back in, keeping that intensity up.

Relentlessly, I fucked him with it, as orgasm after orgasm wracked his body.  More than once, he felt the carpet beneath him, expecting to feel his cum there.

But no, he cums like a girl now.  Not a man.

The sounds coming from him grew increasingly desperate as he was more and more overwhelmed.  And still, I didn’t stop.

After the tenth-ish (I think), I twisted the bottom of the massager, turning on the vibration.  He gasped and moaned with the unexpected sensation, and his orgasms started coming faster and harder.  I almost didn’t even have to move it.  All I had to do was keep that vibrating bulb against his prostate.

He lowered his head, whimpering, still subconsciously moving forward, trying to get away.  I just moved with him, eventually rising up off the bed and standing beside him, keeping that pressure there.

It was getting harder and harder for him to stay still, and he buried his face in the carpet, his hands gripping his ankles in what I assume was an attempt to keep from squirming away, his adorable cries getting louder, longer, and higher as he lost himself in the sensation.

I didn’t speak much during any of this, allowing him the freedom to lose himself in his head, to focus only on the pleasure rolling through him, free from distraction.  And really, he gave me such a lovely show.

He wasn’t pushing back against me anymore, trying to fuck himself on whatever was inside him, like he usually did.  Pinned against the wall, he couldn’t squirm any farther forward, could do nothing but whimper and whine and moan while I thoroughly, relentlessly fucked him.

Finally, after his…. Oh hell, I don’t even know.  20th, maybe?… orgasm, his body finally went slack, and he slid to the side, collapsing onto his stomach, panting and gasping.

I grinned, momentarily considering moving with him and continuing my use of his hole, but decided against it.  This was supposed to be a reward, after all.

I knelt down next to him, running my hands soothingly along his body as he rolled over, completely spent, onto his back.

“Feel good?” I asked, smiling.

“Holy fuck,” he replied, still squirming involuntarily, just a bit.

After a moment, he deliberately moved his leg across the area of the carpet he’d been kneeling over.

I laughed.  “You thought you squirted?”

“I could’ve sworn I did,” he replied.  “I swear at one point I looked back and saw a stream.”

“I think that was precum,” I told him.  “You were dripping quite a bit.”

He nodded, taking a deep, steadying breath.  I was still smiling.

“You do know I’m not done with you yet, right?”

“I know.”

“Then roll over.”

He obediently rolled onto his stomach, and I pulled a paddle out of the bag, hitting him hard with it.  Shortly after, I switched to my hand, spanking his ass, thoroughly reddening it, and mixing that with a few long strokes of raking my nails painfully down his back.

But then, I rose to my feet and told him to stand up, too.  I walked into the bathroom, surveying the tub, and quickly figured out the logistics.

I turned to him.

“I need the tub filled with cool water, I need something soft on the floor that you can kneel on, that you don’t mind getting wet, and I need an extra towel.  And wash all your makeup off.”

He nodded, hurrying to fulfill my commands.  By the time he was done, I sat on the toilet seat beside the tub, two lengths of rope in my hands.

I told him to come stand in front of me, positioned him the way I wanted him, and began tying the rope around his thighs, binding his wrists to them.

Once I was satisfied it would hold him, but wouldn’t be too tight, I had him kneel down, facing the tub, and stood behind him.

“How’s your ass?” I asked.  “Is it sore?”

He shrugged, shaking his head.  “Not really.”

“Oh good.”  I bent him over and slid a lubed plug into his ass.  Judging by his grunts as I pushed it in, I guessed he was maybe a little more sore than he thought.

The tub was full, so I turned off the water, then grabbed him by the leash attached to his collar, pulling him back against me.

“Do you know what I’m going to do to you?” I asked, gently caressing his neck, shoulders, and chest.

“No.”

“Are you nervous?”

“A little.”

I grinned.  Only a little?

I had the dildo nearby, along with a long, thin cane, but I wasn’t going to use those quite yet.

I pushed him down until his chest was resting on the edge of the tub, his face over the water.  And then, with a firm hand on the back of his neck, I pushed down further, until his face was submerged.

For a moment, he was still, obeying the unspoken command that was the pressure of my hand on his neck.

And then, once his lungs began burning, he began struggling, pushing up against me.  I held him down only a second longer before releasing him, letting him up.  I gave him a moment to catch his breath, then pushed him under again.

This time, I held him down a fraction of a second longer before letting him up, pulling him upright by his collar, his head against my chest, and shoved the cock in his mouth, gagging him.  When he coughed and sputtered, I slapped him and pushed him back down into the water.

The longer this went on, the longer I held him down once he started struggling, the harder I made him push back against me before releasing him and shoving the cock back down his throat.

At one point, I bent him back over, but didn’t push him under, instead turning my attention to the cane, and his reddened, spanked ass.

It didn’t take long before his grunts of pain told me he was reaching his pain threshold, and I grinned, setting the cane down.  I knew each sting of the cane would cause him to clench his sore, raw muscles on the plug in him.

And just to prove my point, I reached down and tugged on the plug, loving the sounds he makes when he’s in pain.

The longer I went on, the more tired and worn out he seemed to get (what a shock).  Finally, he said, “Okay, I need this taken out.”

I kept him bent over, resting his weight on the edge of the tub, and hooked my fingers firmly around the plug.  It wasn’t overly big, but he was already sore, and his skin was already irritated to the point that just having it in had become unbearable.

It was going to hurt coming out.

“Are you ready?” I asked him, one hand on the small of his back to steady him.

“Yeah,” he said through gritted teeth.

With one smooth, quick motion, I pulled it all the way out.  And his scream was every kind of delicious.

Exhausted and in pain, he fell to the side, leaning against the tub, resting his head on the edge, trembling and panting.  I put a reassuring hand on his shoulder, giving him the time he needed to recover.

After a few moments, he sighed and straightened up, and I pulled him back against me, gently this time, and again ran my fingers along his body.  I quickly untied his hands and stepped back as he staggered to his feet, bent over, his hands on his knees.

I took the opportunity to remove his collar, and the relief of having that tension gone was audible in his voice.

When he straightened up, I smiled at him.  “How do you feel?” I asked him.

He gestured with his hands, a movement I translated as “shaky,” so I said, “Come on, come lie down.”

We went back to the bed, and he sat down on the edge, sighing and panting as he tried to get his head right again.

After a few minutes, he sighed and said, “Was that shorter than you wanted?”

“No,” I told him quickly, rubbing his shoulder.  I was sitting behind him, so he didn’t see me smile.

He’d just been pushed to the point of screaming in pain, barely able to stand upright, and five minutes later, he was asking if I was happy with him, or if he’d somehow disappointed me.

That’s where his head was.  That’s what was important to him in that moment.

My sweet, darling, obedient little sissy.

I pulled him back to lie down on the bed, grabbed the lube, and began stroking his cock.  I knew it wouldn’t make him cum (and I doubted he’d be up for another orgasm at that point, even if he could), but I wanted something that would feel mostly good to him.

I mean, of course I worked it once he got sensitive, making him squirm.  I couldn’t be too nice to him.

But I didn’t torture him too much, or for too long.  He’d had a long evening.

I told him to get up and get dressed, and I got all my things together and put them back in my bag.  We went back into the living room, where he poured us both glasses of water, and we sat down on the couch.

I pulled him to me immediately, and we sat for a few moments, watching TV.  Then, I kissed the top of his head and pushed him up.

“I’m going to head out,” I told him.  The poor boy needed to rest, after what I’d put him through.  And I actually didn’t keep him up later than he was used to staying up, for a change.  He needed sleep.

He walked me to my car, hugged me, and I drove off.

It definitely gave me plenty of awesome memories to help get me through the next few days of dealing with my psychotic mother.

10 thoughts on “The sadist and the sissy

  1. How is his body changes going? More noticeable now?

    • Domina Jen says:

      They would be, if my doctor wasn’t such a worthless cunt who can’t go a whole week without canceling appointments. As it is I have to try and find a new doctor while I’m out of town and hope they can see me asap when I get back in 2 weeks. But he’s out of pills now, so he won’t be able to take more until I get back.

      But at least the new ones will be a stronger dose, so it’ll Jumpstart the changes again.

  2. Cari says:

    Very hot! What a LUCKY sissy and pain slut he is. 💜

  3. I’ve said it before and I’ll say it again. What a lucky boy.

  4. Chris says:

    He is, he is, definitely… *lol*… and *crave*

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