Pain & Pleasure

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Mistress tests Rory, pushing her further than ever before.
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RoryRouge
RoryRouge
615 Followers

This is a new focus for me. I've always been interested in pain, and the pleasure and dynamics it can provide, but personally it isn't something I have experienced much of. A lot of these stories are fantasies I experience through Rory, but I realise this is a part of BDSM that is a fine balance. I hope you like it :)

I squirmed as I waited for Mistress to finish fussing with my outfit. She seemed extra persistent tonight, straightening my garters until she was satisfied, re-aligning the bows on the back of my light pink stockings, and ensuring my corset was sufficiently tight. Feeling that constant constriction, bondage built into my outfit, always brought a girly giggle to my lips.

My squirming was brought to an end as I whimpered under her glare, the stern expression leaving no room for misinterpretation. Mistress always had a way of silencing me with a simple look, phrase, or touch. She didn't need a collar to make me feel owned, although the heart shaped pink one tightly wrapped around my throat certainly helped! The subtle touch around my throat, a gentle and yet elegant reminder that I was her good girl.

Kneeling in front of her, she put the final touches on my evening outfit. A matching pink bow firmly clipped in my hair, enjoying how much it made me blush. Mistress took her time straightening it, drinking in my reddening face, feeling it on my head. She enjoyed the humiliation I felt at her hands, even more so when she got to show me off to friends. As much as I protested, I enjoyed those moments thoroughly, knowing how proud Mistress was of her little sissy.

Satisfied with the bow, she sat me on the edge of her bed, sliding pink heels onto my feet. I giggled as I stared down, heels a matching pink to the rest of my ensemble, with bows that mimicked the one in my hair adorning the toe and heel of each shoe. It was a girly sissy night, feeling pretty and little, a pink vulnerable sissy for my Mistress. I felt myself falling under her spell, craving her control. My eyes wide, excited and vulnerable, I knew I was ready for whatever my Mistress had in store.

I blushed as she drank me in, her doll finished for her to play with. Smiling, Mistress ran her hands over my stockings, drawing tiny little moans out of her sissy. Playfully, she gently ran one finger over my caged clit, making it twitch with frustration and need. My noises continued, her smile growing as she saw the aching desperation beginning to grow inside of me. I whimpered as her hands left me, phone clicking away as she took picture after picture.

Directed into different poses, blushing and shaking with excitement, I giggled after each click of her camera. Mistress enjoyed capturing her little slut, holding my clit in her hands as she snapped pictures and videos of her favourite toy. Spreading my cheeks to show off my clit and plug, legs in the air while I bit my lip, sucking on my finger with wide eyes, on my knees while I stared up at her, mouth open and ready. Mistress took her time putting me through all kinds of different humiliating and exciting positions, slowly watching the hunger in my eyes grow.

Clit beginning to throb and leak, her sissy properly dressed for the evening she had planned, Mistress smirked as she left, exploring her closet of toys. Whimpering, not sure what to expect from that slightly evil smirk she left implanted in my mind, I kept my heels and legs together, patiently sitting on the edge of the bed. Drumming my painted nails on my stockings, trying to not shake with excitement, I waited. Waited for what was planned for me. Waited to be her good girl.

I tried to see what was in her arms, but she scolded my eagerness, commanding me to stare at my feet. With a blush, I did as I was told, taking in the sight of my adorable shoes. I listened as Mistress placed some items on the bed, climbing up behind me, feeling her breath on my neck. Moaning, slowly sinking into her touch, I leaned back as she kissed my neck, asking if I was ready to be her good girl. My voice stolen by my excitement, I could only nod, so desperate to do as I was told. To be her sissy.

Hands brought behind me, holding each respective arm, she quickly tied a harness around my chest. Already feeling tight from the corset, I softly whimpered as the rope began to dig into me, falling further under her control. Content I no longer has the use of my upper body, Mistress playfully pulled me back onto the bed, climbing on top of her sissy. Hands on either side of my face, brushing the wig out of my eyes, she simply stared, those big beautiful eyes captivating me, drawing me in. With a slight smile, she gently kissed me forehead, telling me to be her good girl.

Enthralled by my Mistress, wanting to follow her every whim, I shivered as she draped me over her lap. Settling in, turning my face to rest comfortably on the bed so I could see her, I squealed as she playfully spanked my exposed ass. Taking more rope, Mistress tied my thighs, knees, and ankles together, ensuring I was truly immobilised. I squirmed, testing out my new bonds, wriggling back and forth. Smiling at my pathetic attempts, she put an end to it with a few playful spanks, giggles escaping through the smile on my face.

Those giggles began to turn into moans as her hands began to rub and squeeze, exploring the vulnerable sissy before her. My clitty was trapped between my legs, exposed and held in place from my bondage, on display for Mistress to play with. I felt her begin to rub oil all over my ass and clit, squeezing and rubbing it into me. I moaned under her touch, enjoying being the center of her attention, the focus of her hands. When she took careful consideration to rub oil over my balls, I felt like I could cum then and there.

But of course Mistress had other plans, moving to another toy she had retrieved from the closet. Still lost in a fog of arousal from her massage, I barely felt her remove my plug, nearly screaming in lust as she began to push the dildo inside of me. Stretching my eager hole, I pushed hard against the assailant currently working its way inside of me. Gently, wanting to ease me into it, she moved just the tip in and out of me, slowly getting the eager sissy across her lap worked up. The mix of being fucked with her occasional firm spanks had me in a state of frustration and lust.

The handheld cock was pushed deeper and deeper inside of me, almost forcing moans out of my painted lips. That familiar tingle instantly began to build inside of my clit, that eagerness to cum. I felt the cock pushing in and out of me slowly, causing me to whimper, plead, and beg to cum. Mistress answered my frustrations with a few light taps on my full, denied balls, making me flinch and whine. A firm spank on my ass brought me back down, reminding me to be her good girl.

Again the cock began to work its way inside of me, rubbing right against my g-spot. My involuntary moans continued, lost to the feeling of being fucked. Yet like before, as I got close to cumming, as that familiar feeling crept back into my clit, Mistress pulled back, leaving her cock inside of me, and spanked my poor balls, held almost on display from my bondage and cage, stretched tight and exposed. I cried out, tears starting to form in my eyes, as her soft hands tapped and spanked with a bit more force.

Back and forth she went, edging me with her cock, only to spank my balls harder and harder, chasing away the orgasm trapped in my clit. Tears openly flowed from me as she told me to be her good girl, her good sissy, her good toy. I whimpered and whined as I felt my balls ache, sore from the assault she was putting them through. Breaking to rub them every so often, or moving to spank my ass, I breathed heavily as she gave me reprieve, knowing that it would be short lived.

Leaving the cock inside of me, she brought a vibrator to my clit and balls, tender from being punished yet so eager to cum. Yet, as I once again got close, as my moans grew louder, voice caught in my throat, Mistress returned to her punishment, spanking harder and harder on her favourite toy. Tears streaming down my face, mascara running, I cried as she didn't relent, my mind confused and torn between the pain and pleasure of what was happening to me.

All the while Mistress soothed me over with her voice, her calming assurance. Bringing her hand down on my balls, stretched and vulnerable, she called me her good girl again and again, telling me how happy I was making her. In pain and tears, I focused on her voice, finding strength in hearing her comforting support. Each time she called me her good girl, that familiar warmth coursed through me, wanting to do anything to hear it again and again.

Mistress returned the vibrator to my aching balls, asking me if I was her sissy. I cried yes, desperately trying to push as hard as I could into her wand. A firm hand on my lower back, forcing me back down, she asked if I was ready to suffer to be her good little sissy. Whimpering, I begged to be her toy, to be her good girl. I knew what was coming, yet I was enslaved to that feeling coursing through my clit, that ever present need to cum. But once again it was stolen from me, replaced by the sting of her hand on my balls, painfully spanking my orgasm away.

Unable to contain it anymore, I openly wept as she brushed back my hair, watching the torment her sissy was going through. Comforting words from my Mistress as she again pushed the dildo in and out of me, telling her good girl to suffer for her just a bit longer. Moving her cock up and down, intermittently spanking my balls hard while she fucked me. So confused, not sure how to feel, I simply submitted to her control, to her will. Balls aching, my asshole clenching onto her cock for support, I knew I only had to be her good girl.

I felt Mistress speed up her cock, fucking her sissy hard. Voice matching her intensity, she demanded if I was ready to cum. I screamed yes, so desperate to have the orgasm that had been stolen from me all evening. With a final thrust, shoving the dildo as far into me as it would go, Mistress began to spank my balls hard over and over, telling her sissy to cum for her. I cried, my emotions confused, not sure how my body felt, barely able to see through teary eyes as she brought her hand down again and again on my exposed balls.

But then it happened. How my Mistress knew I don't know, but as she spanked my balls and clit hard and fast, I felt my ass clench around the cock inside of me. I felt my clit strain in its cage, my balls beyond sore and aching. And I felt the orgasm that had been stolen from me all evening rip though my body. No vibrations, no motion from her cock, just the rhythmic spanking of her sissies balls, and I came. Crying, euphoric, quivering, shaking in her hands, I felt my orgasm explode out of me. Clitty streaming denied cum, spurting all over my nylon legs, Mistress never relenting from her assault on my balls.

Finishing cumming, my clit still leaking from the powerful and confusing orgasm I had been put through, Mistress soothed the quivering and whimpering sissy before her. I was quickly untied, brought to lie against her chest on the bed. I flinched and whined as she ever so gently rubbed soothing oil over my spent and bruised balls, all the while calling me her good girl. Her gentle, comforting touch in her arms making me sink into her, still able to feel the aching in my clit. Soft kisses adorned my forehead, her hands never leaving my balls.

Flipped on my back, pressing herself against my asshole as if I was going to be fucked, Mistress gently inspected my clit. Seeing my balls throb and ache, her eyes going wide with excitement and approval, she continued rubbing oil over them. Still tender and sore, even her subtle touch was enough to make me whimper. Leaning down, faces pressed right against one another, Mistress told me what a good girl I had been, how proud she was of her sissy. She said this wasn't the last time I would cum like this, that my balls and clit were hers to do with what she willed. Feeling the pulsing, throbbing, and aching feeling between my legs, I could only stare into the determined eyes of my Mistress. I could only accept that I was her toy. Her plaything. Her sissy.

Smiling, her intense stare captivating me, Mistress slowly flipped us around, her back resting comfortably on the bed. I could sense that familiar need in her as she placed a hand on my head, pushing me down into her pussy. My tongue went to work pleasing my Mistress, licking and sucking with a growing frenzy. Her moans flowing over me, the excitement of what she had done to me was evident. And as she came for the first time using me, I felt my still throbbing balls between my legs. Forced to give my Mistress an orgasm, while I had been put through so much to earn my own.

Her hands in my hair, thighs squeezing on either side of my face, she shook and moaned as she came all over my face. In that moment I felt what I was to her, what I wanted to be for her, what I needed to be for her. The good girl that she could praise, or punish. The sissy she could humiliate, or pleasure. The toy she could show off, or hurt. The little plaything that she used to fulfill her every whim. Hands running firmly through my hair, grinding herself on my tongue as she came down from her orgasm, I could feel the power and control she had over me radiating from her body.

Finished using my tongue for the night, she brought me back up against her, hands immediately holding my clit. Smiling, Mistress softly kissed my forehead, once again calling me her good girl. As she fell asleep, my throbbing balls still in her palm, I embraced the aching feeling spreading through my body. I knew I'd look forward to the next time she punished me so, forcing my orgasm out of me through pain. Through torment. Seeing the smile on her face as she slept, her gentle grip on the clit she had caged and controlled, I knew I'd do anything that made Mistress smile.

I knew I'd do anything to be her sissy.

RoryRouge
RoryRouge
615 Followers
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AnonymousAnonymousabout 2 years ago

Well, it is a nice loving story between a sissy and his/her mistress. She seems to care for her sissy and she even allows it to cum. It would be nicer if she actually caused him more distress if she punished him more. If she edged her sissy longer and then gave him a ruined orgasm it would be more fitting. She did not give him a lot of pain but it is assumed that the author is not into pain. Mistress does give it a lot of good aftercare which is often missed in such a relationship.

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