Mistress Stretched My Hole and Rearranged My Insides
The jeweled plug came out with relative ease, leaving me unbearable empty. She slapped each of my cheeks a few times, making me cry out in pain and frustration. She was surprisingly strong for her frame.
She tightened the silky black blindfold just under my ponytail. I had pretty long, straight hair that I usually wore down, but she insisted that I looked irresistible with a tight high-top ponytail.
In total darkness, I tried to trace her steps as she moved around me. The cold air from a cracked open window sizzled on my still-damp with sweat skin. I arched my back a little more, hoping to look sexier; being on all fours made me feel a little less graceful than I’d like.
My head was pushed down rather harshly and I face-planted between her legs and into her pussy. Still so wet… I knew what to do and I immediately got down to it. Her scent filled my mind. Immersed in the process, I was encouraged by her hands gently petting my head, occasionally grabbing my hair to direct my efforts better.
She reached over past my plugged-up butt, tapping on it twice before moving lower and slipping something small into my aching hole, meeting no resistance. The other end of the toy extended up, covering my clit. She leaned back, grabbed my hair, and pushed me further down from her pussy. More than eager to please her, I plunged my tongue into her ass, aided by her hand pressing me into her. With my mouth occupied, I could only moan as the toy began to vibrate.
“I want you to tell me if you feel close, ok?”
“Yes,” I purred, briefly interrupted from my task.
Time always seems to stop in moments like this but I licked her sweet puckered hole for what seemed like minutes. Her moans, the buzzing in my cunt, the cold breeze on my skin, everything was just perfect. Soon I felt a wave of an orgasm forming in my belly.
“I’m about to cum.”
Suddenly the buzzing stopped.
“Hey!” I laughed. “Please?”
“You know I like to come first, angel. Don’t be selfish,” she teased, guiding my face back to where it belonged.
From that point on, time no longer stood still, it stretched, endlessly. The vibrator over my clit would occasionally come back to life, but never for long enough. The ever-building edge filled me to the brim, pushing out the last of my thoughts. I licked with desperation, ignoring the aching muscles of my tongue, muscles I’d never even considered I had until then.
I was turned on my back now, flat against the floor. She sat on my face, facing my breasts, using my erect nipples as handles to better grind on my face. Any time I’d thought I felt her swell up, ready for release, she’d slide down. I figured she must’ve wanted to cum with my tongue in her ass, so I went at it, pushing my tongue past her ring and deep into her rectal canal. It never seemed to be enough though. I wondered what stopped her from reaching the peak, worried I wasn’t good enough for her.
She walked around me and pulled the teasing vibrator out of my cunt. I held my breath in anticipation of her lips, but all that followed was some less-than-gentle tugging on the plug. I had almost forgotten about it, used to the filling sensation.
This went on for so long that eventually, I found myself begging her for my orgasm.
“Shh, angel,” she whispered as my mouth got stuffed with some kind of a rubber ball.
The straps snapped shut, then tightened behind me. She resumed playing with my jeweled plug while I listened to my own muffled whimpers. The soft stretching of my anus felt like a gift from heaven. The few times I let some overly insistent boyfriend take my tight hole were nothing like that. I had no idea how intoxicatingly sweet the ass could ache for an orgasm, or how it felt to be stuffed into one, at the mercy of a woman whom I was no longer certain I knew. To be fair, I recognized myself even less.
All sensations came to a halt when she got up, suddenly, as if called by something, leaving me cold and panting.
Were we done? Have I failed? She’s never taken this long to orgasm with me before…
Suddenly her warm mouth enveloped my nipple and I lost myself to moaning again. She traced her way up my neck and to my ear.
“Baby, the way your greedy little asshole stretches around that plug… God! You’re driving me crazy.”
Limited in my response, I moaned, trying to sound grateful. I felt a little lighter, reassured of her desire for me.
“I’m going to make your ass mine, do you understand?”
I nodded eagerly. She could have anything she wanted.
“Yeah… that’s what you want, isn’t it? To get your ass fucked? Can you even handle that?”
I consented as strongly as my position allowed me. The only thing I was certain I couldn’t handle anymore was my throbbing, abandoned pussy.
“Look at you, so desperate to get stuffed. But you just love to play hard to get, don’t you? Such a sexy little unavailable girl… Except, I see you, baby. I see what you want. I can feel it.”
The warmth of her voice gushing over my earlobe pushed me to the verge of tears.
“Such a sweet, dirty slut… look at you, you’re shaking like a leaf. That little plug is not enough anymore, huh? You need more,” she said as she released one of the straps, letting the blindfold slip down.
My eyes were fixed on her, biting my lower lip, begging for release.
“You want to cum on a fat dildo, like the good little anal slut you are?” she asked, slowly pulling the plug out until halfway.
I moaned and nodded my approval.
“Then beg, angel. Beg for release.”
She unlocked the strap of the ball gag, freeing my mouth. I was flooded with emotions.
“Please, please, yes…” I whimpered through my stiff jaw. “Please fuck my ass.”
“Oh, so it’s not gross anymore?”
“No! I’m sorry, I was being stupid. Please, just let me cum….”
“Mistress. You can call me that since you’re already begging like a slave.”
“Please, Mistress.”
The word felt strange in my mouth.
“Please let me cum, Mistress. I’m begging you… I really need to.”
“I knew you were a slut, angel… but here’s the thing… from now on, you’re gonna be my slut only, you understand? Only for me.”
“Yes, Mistress. I’ll be your slut if that’s what you want.”
“No,” her hand wrapped around my throat, pressing lightly. “It’s not what I want. It’s who you are. Time to own that, since you want to be fucked like one so much.”
“Please… You’re right…” I wasn’t holding back the tears or the sobbing anymore, nor questioning where they came from. “I’m such a slut. Please, I just really need this right now, please fuck me. Please use my ass, Mistress. It’s yours. I’m yours.”
“Such a needy slut,” she said, fixing the blindfold back on.
I felt Mistress move away from me and to the other end of the room.
“Get back on all fours, slut,” she commanded.
I did just that, arching my back in anticipation.
The plug came out with relative ease, leaving me unbearable empty. She slapped each of my cheeks a few times, making me cry out in pain and frustration. She was surprisingly strong for her frame.
“You’re dripping, baby.”
Dripping? I was flooding. I could feel the juices on my inner thighs, thin strings stretching down from my swollen pussy. Then I felt something pressing into me. Emboldened by my success with the plug I felt confident when I said I could handle it. But the tip pressing against my anus felt ominously large.
“I see you tightening up,” she said, her tone growing colder. “Doesn’t look like you want it much.”
“No, please! I swear I do.”
“Yeah? Well, you can fuck yourself then.”
She reached over and pulled my ponytail back.
“I want to see your ass swallow the whole thing, do you understand?”
“Yes, Mistress.”
“Good girl. If you can’t handle it, your safe word is “gross”. Say it once and we’re done, we stop immediately. Got it?”
“Yes,” I said, knowing full well that I couldn’t risk her disappointment.
She could grow so cold, so fast sometimes.
“Now, slut. Push yourself on it.”
I pressed back cautiously. The discomfort grew alarmingly quickly, and without making much progress I seemed to reach my limit. My anus tightened in protest, the tip only barely inside me, nowhere near its full girth. This was way too large, she couldn’t be serious, could she?
“Oh, so you’re all talk and no action, huh? Go ahead, use your escape word baby. I’ll have you on your way back to your pitiful life. Tap out any time, my little slut wannabe. I’m only interested in the real deal.”
I pressed back on the dildo even harder. The silicone moved just a fraction when the pain began to really form.
“Please, Mistress. It’s too big.”
“What is it they say? Go big or go home?”
“Could we just switch to a smaller one for now, please? It’s gonna hurt…”
“I won’t. This is what you asked for, remember?”
Beads of sweat formed on my skin, mixing with tears somewhere along the way. My already impossibly stretched ass was on fire. I had hoped most of the tip was inside, but the girth kept increasing. I was honestly worried it’d tear my ass open if I pushed more.
“You’ll be fine, angel,” she cut my complaints off, squirting some more lube over me.
“I’m scared,” I said through tears and attempted to move again, giving up almost immediately.
The pain was moments from completely unbearable. I couldn’t hold back the crying anymore. Her fingers dug into my hips as she leaned a little closer to my ear.
“Now or never. Take it or get out, you spoiled slut.”
I sobbed even harder, feeling sorry for myself and my impossible situation. Her hand slipped around me, reaching my desperate clit. I groaned like a wild animal.
“Take it in, slut. I won’t ask again.”
I gathered the last of my dwindling resolve into one decisive thrust. The head of the dildo finally slipped in, tearing me apart. My screams filled the room, or, possibly, the entire building.
“Yes, angel!” she exclaimed, squeezing my hips and bending down “There you go… good, such a good girl…”
Gripped just on the edge of bearable, I sobbed and whimpered, terrified I’d hurt myself too much and the pain wouldn’t stop.
“That’s it, baby, just relax. The hardest part is in. If you could see how much your slutty ass loved swallowing that head cock…”
She was soft and sweet again, petting my back.
“Now ride it, baby. I want to cum watching you struggle for me.”
I’m not entirely sure why I didn’t leave. I wanted to cum, yes, but, I thought, the nearly paralyzing pain will have prevented me from that. I just knew I couldn’t go home. I was worried that would be the end of us.
For the next few minutes, I impaled myself further on her seemingly endless strap-on. A loud, wet, sweaty, snotty mess. I was convinced I lost my mind for a moment there.
Somewhere deep into this tortured trance, a nagging sweetness began to form, and the pain disappeared, transforming any sensation from my rectum into pleasure.
Her fingers abandoned my clit once again.
“I’m so close, please… let me cum, please touch me, Mistress,” I begged for her hand to return.
“You can cum when I do, but you don’t need help. This should be more than enough for you,” she slammed her hips into me. “Be grateful, baby. See how much I appreciate you?”
God, I was losing it. Maybe she was right.
“I don’t hear you thanking me, slut.”
“Sorry, thank you for using my ass, Mistress! It feels so… good…” I blabbered in pain as she thrust into me furiously. “Mistress, please!”
“Please what? You want more, huh?”
Another forceful thrust made me cry out again.
“I know it hurts, but you love it anyway don’t you? My sweet, needy little pain slut…”
“I love it,” I winced through the pain. “Thank you, Mistress…”
She landed a heavy, stinging slap right over my clitoris. I cried out again, but this time the rush of the nearing orgasm was just as strong as the burn.
“Ride it, slut! Show me how you love it.”
Another loud smack, this time on my ass, and I obediently picked up her rhythm, pushing my hips back, impaling myself again and again, fearing every thrust as the one to finally rip me apart.
“Yes, thank you… argh… fuck… thank you, Mistress…” I screamed, over and over.
“Fuck, angel, don’t stop. Don’t you dare stop, you hear me?”
The pitch of her moans reached its highest notes and God, did she sound gorgeous. Soon a tsunami of my own orgasm swept me off, taking the last of my composure with it. Every sensation of the night converged into one single point and exploded in the sweet release I begged for.
Still hazy, I was brought back into the present moment when the thick mushroom tip of the dildo pulled through my tight ring on its way out, stretching me for one last time. A wet mess, I collapsed on the floor, still sobbing, overwhelmed, and empty.
Unusually fragile, I was less distracted by my pulsating, burning asshole than by the feeling that I had done something wrong. I lost composure. The sound of my crazed squealing and pleading was still stuck in my ears.
After what she’d seen, I wondered if her eyes could ever look at me with the same playful reverence as that first night. I kept my head down, afraid to find out. In silence, she spread out in front of me and I closed my eyes, lapping up her sweet creamy cunt on autopilot. She pulled the tie off my hair and slipped her fingertips through, gently massaging the top of my head. The familiar by now practice soothed me. The micro spasms subdued, and the tension was gone. Arched down between her thighs, I dutifully cleaned every dip and fold, finally sucking the last few drops of nectar out of her. There was no sign for me to stop, so I didn’t.
Slowly, my worries faded away and I lost myself to the intimacy of the moment. After all the intensity of the night, I was overcome with a tenderness towards her. My mistress. My pussy licking turned into a loving make-out session with her labia, without me realizing.
“Touch yourself,” she half whispered. “I want to watch you shake like that again.”
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