Difficult Pleasures

by Upper Hand

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© Copyright 2013 - Upper Hand - Used by permission

Storycodes: F/m; femdom; strip; shave; bond; rope; fem; nylon; gag; tape; cbt; tease; torment; denial; sex; climax; fpov; cons/reluct; XX

I loved having him tied up. He had always been so reluctant when I mentioned bondage to him, but he truly loved me - and oh God, he made a fantastic slave. So he put up with my kinky tendencies, letting me seduce him over and over into situations he always regretted. But there was something so totally empowering in knowing that I could have him at my beck and call whenever I wanted, doing whatever I asked him to make me feel like a goddess.

I’d always been fascinated with feminization. Maybe it was growing up behind the shadow of two brothers, wishing I could show them how difficult it was to walk in my shoes as a woman (especially if they were high heels), or maybe it was just my own dominant tendencies but there was something so gratifying in making my man my woman. To know that he hated it (in our less kinky moments, he was brutally truthful with me) but did it. For my sake. And even when he was bound and sick with himself for how low he had once again gone for me, I could bring him to orgasm … even if he whimpered and mewled and begged through his gag for me to stop bringing him to the edge, over … and over … and over.

Today was no different. I invited him to my flat, thinking about all the toys I was going to use on him today (my father had left me far too much money for me to simply sit on it in a bank account) and led him in. Idle talk gave way to impatience. I wanted him as mine, now, with no further delay.

First I stood up, walking behind him, touching and drifting my hand over his hair and shoulders, letting him wait for the moment. As I bent down to bite his ear, I put a hand down to pull up his shirt. He begged me to not do anything too extreme. Once more I remanded him for thinking he had any say.

Before he knew it, he was naked before me, and I handed him a razor and shaving cream. He didn’t even need to ask, he simply walked to the bathroom - I had trained him well, and he had failed to properly prepare like I told him. He tried to mumble something before about how he didn’t want to have to wear pants for the next two months, but our play sessions after had been one of the more painful, so I doubt he missed the lesson.

He promptly returned. I attached a leash to him, but it wasn’t going to his neck, it was firmly around a protrusion that was much more … responsive, shall we say. He knew much better than to not follow obediently. Tugs, short and quick, were things he wished to avoid. I led him up the stairs (he did well, I only needed to yank twice) to my bed upstairs, fastening his hands to the posts above before I undid his leash. I told him to wait there and not breathe.

I came back with all my supplies, hearing (with pleasure) his deep exhale when I returned. I admired his handiwork on his legs - his legs were smooth to the touch, and I commended him for a depilation well done. I watched with elation as I saw an erection grow as I slid nude pantyhose over his legs, feeling the entire garment mesh and mold to his curves, running my hand up and down his legs. I loved this feeling, watching him smile (and almost in a way looking like he was trying to hide the fact that he was experiencing pleasure from this tactile moment) and knowing that I had him in my total control.

Next, I put fishnets on him, making his lower half into a smorgasbord of fabric touches. I must have spent ten minutes simply stroking him, putting one hand on his body and one hand on my own. I moved on to his face, making sure that all of my weight was firmly planted where it made it hardest for him to breathe. This part was always the most concentrated of our play sessions. There was something almost meditative in painting his face with makeup, making his face my canvas, letting him experience the soft strokes of brushes and pencils, concentrating sensation on his lovely, lovely face.

Now I got dressed - putting on tights myself. My nylon fetish was non-negotiable. It was so utterly strong that it had been with me since I was four, and I used some form of nylon in every one of our play sessions. This time, I didn’t just put powder blue tights on my legs - I drew a pair over my arms as well, a hole cut in the crotch so I could draw my head through. A final blue stocking went over my head. I could see him watching me. As much as I know he was vanilla, he still loved my body. I smiled to myself, knowing he was still staring at my bosom.

I went over to my beautiful, beautiful toy, letting my fingers travel all over his body. I drew out a gag. I heard him gulp, saw his body flinch. I shushed him, watching his erection flinch with pleasure as I put a finger to his lips (I think he did love that moment, every single time) and pushing the gag sharply into his mouth. It filled his mouth with a sac I could inflate to my pleasure (too much pressure meant a deliciously sore jaw for him). It had a harness attached, so I fastened the gag all the way around his head. I locked the harness on just for fair measure.

His eyes locked onto mine as I kneeled above him. I lowered my pussy onto his sealed mouth, letting his nose rub against and pleasure my clit, feeling the warm spreadings of sexual pleasure running up and down my spine - and placing one hand covering his nostrils. I started grinding back and forth, letting my orgasm quickly and decisively take its course. When I let go of his nose, his eyes rolled back from his head - I might have gone a bit too long. His breath soon regained its previous sharp rhythm.

Next I grabbed his feet, shoving them to either side and strapping them firmly to each corner in leather. Also, because I didn’t want his erection getting too happy (I never let him come. He had to wait till he went home for that) I brought the tights encasing his legs below his midsection - he knew what was coming. He flinched at the sound of the duct tape being taken off the roll. One piece at the start being placed directly on the head of his penis. (It would take him forever to take the tape off - sometimes it took a small amount of skin with it, but I didn’t particularly care. My toy always take some wear and tear.) One long piece wound down his shaft, making his cock now my silver dildo. Before I taped his balls, I wound a shoestring around the base and strictly around each ball - for some reason, every time I wound it tighter, the groan it elicited from him made me instantly want to fuck myself silly (whether it be on his cock or his face.) Now, I watched as his entire package was silver, occasionally twitching from the sheer severity of its restraint.

Now, I really couldn’t wait to finish myself. He was just too perfect. Completely emasculated, made pretty and soft, his penis encased as thickly as his mouth was gagged - it drove me mad just thinking about it. This was what I craved, the power to imprison someone in my own fantasies, to enact my reality on them even when it caused pain and discomfort. And it always surprised me, for no matter how severe I made his restraints, no matter how many times I wreaked havoc on his identity, he always came back for more. No matter how many times he did told me he didn’t enjoy it but simply wanted to fulfill what role I needed to make myself happy, he always came back when I asked. The power was intoxicating. It was a brew that only made me grow thirstier the more I drank.

I wrapped my hand around his cock. I could feel the material crinkling beneath my hand, the fabric surrounding my fingers stretching and rubbing, certain folds in the tape crimping and causing him to whimper from the pain. I could find no spot along his penis, that when squeezed, didn’t bring a fair amount of pain to my toy. But I wanted it. I wanted my toy’s cock.

I brought out a condom, sliding it over the creases and folds of my toy’s tape-encased penis. As soon as it was on, I couldn’t help myself. I swung my legs over my gorgeous, gorgeous toy, mounting him through the hole in my hose, feeling him violently twist and buck beneath me. He was in agony; I was turned on more than ever.

Because I had already brought myself to orgasm before, I had a bit better control over myself this time - slowly rocking back and forth, letting the tension build, placing my hand behind me to stroke his nylon’ed legs, or forward to twist his nipples, or even lay out in front of me and feel him squirm as I deprived him of oxygen once more. I always finished while suffocating him, and today was no different. As one powerful, wrenching orgasm rocked me, he pulled with all his might, trying to break free of his bonds. But I kept going, letting him breathe for a small portion, then grabbing his nose this time. A second orgasm came and flowed through me, a powerful wave sliding back out to sea. This time I didn’t let go. I fucked him with an even more furious rhythm, feeling his penis strain from the bombardment of pain, feeling his head try to get free to sweet air, and finally the final orgasm came, and I came and came. I decided to kindly let my toy continue to live, letting him breathe freely once more.

As I got off the bed, now slightly bored with the scene, I sat down on the love seat, looking at my toy. He turned his head to meet my gaze. He pulled at his restraints, clearly desiring the chance to rub his tortured member and soothe its pain, his muffled cries cutting through the air.

“No, my lovely toy. I haven’t even started with you yet.”

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