61. Theo Fairview #2
“Spread your legs,” she ordered softly, and I did as I was told, shuffling my feet until they were shoulder-width apart to give her access to where I knew she wanted to go.
She made eye contact with me as she slipped her hand down under the hard dildo, before tracing a finger over the seam of my pussy through the fabric of the strap.
“Oh yeah, this is going to fit perfectly against your clit, isn’t it, Theodora?” she hummed, and I bit back another pathetic whine as she slipped the vibrator into the pocket meant exactly for this purpose.
She pinched the toy firmly and rocked it back and forth until it settled neatly into my crease, finding its final resting place against my clit.
I was breathing so fucking hard. I couldn’t look away from her face as she reached into her bra and tugged out the remote.
“On your knees,” she ordered, and I groaned as I dropped to the floor.
My knees hit the carpet, and I found myself suddenly eye level with her perfect, exposed pussy.
My mouth watered, and I leaned forward, instinctively wanting to lick up the slit between her legs.
Suddenly, she was gripping me firmly by the hair, and I hissed in surprise as she jerked my head back and away from her.
“Did I tell you that you could touch?”
She tsked me with her tongue, and I swallowed, shaking my head.
I couldn’t move much with how hard she was gripping my hair, but the rough tug on my scalp sent delicious sparks of pain through my body, and my nipples hardened as wetness flooded between my legs.
“Bad girl,” she chided me, and my head swam with desire as she looked down at me with a deliciously condescending look of disapproval.
“If you want to fuck me, Theodora, you’re going to have to be good and earn it,” she whispered, and I swallowed.
“O-okay. Yes. Please, Cass. Tell me how to earn it. I’ll do anything.”
She let out a dark laugh, and my skin sheeted with goosebumps.
“Mmmm. It’s more about what you’re not going to do.” She smiled at me, then, without warning, she clicked the button on the remote and the small but powerful vibrator rumbled to life.
“Oh fuck…”
I gasped as the low, steady vibrations immediately caused my clit to pulse with need.
My hips jerked involuntarily as she clicked it up a notch, and my breath caught in my throat.
“If you come before I tell you to, I won’t let you fuck me.” She smirked, and my eyes widened, even as I struggled to fight off the slow, creeping build of an impending orgasm.
“Cass…” I panted, rocking my hips slightly in an attempt to dislodge the vibrator from where she’d firmly settled it against my clit. “I c-can’t… I’m not gonna be able to help it, baby…”
“You can and you will. If you get too close, tell me, and I’ll let you take a break. But I want you to try for me. Fight it off, sweet girl. I know you can.”
“O-okay…” I agreed quietly, and she smiled before tucking the remote back into her bra.
“Good girl, now open your mouth,” she demanded, and like the desperate, possessed woman I was, I obediently opened for her.
Before I knew what was happening, she dropped a long, thick line of saliva directly on my tongue, and my eyes bulged in surprise.
She smirked and squeezed my cheeks firmly between her fingers as I struggled to process the fact that she’d just spit in my mouth.
It was so fucking degrading and dirty and exactly what I didn’t even know I needed. Literal tears pooled in my eyes as she squeezed my face harder before leaning in to whisper in my ear.
“Swallow it.”
The order poured over me, and my breath caught in my chest as I did what I was told. My thighs shook, and I gasped out a sharp bark of pain as she abruptly slapped me across the face hard enough that my head snapped to the side.
“Good fucking girl, Theodora,” she purred, and the pain of the slap went directly to my already overstimulated clit.
Oh shit.
I was gonna fucking come!
“Cass… fuck… I’m gonna… baby, fuck I’m gonna–”
Suddenly, the vibrations stopped, and the orgasm that had been barrelling toward its peak immediately halted, and I groaned with the sudden loss.
“Take a break. Breathe baby… You’re doing so well.”
“Cass… please… I want to… let me touch you? Please?” I begged, but she just smiled and shook her head.
“Not yet, baby. I’m not done playing with you yet.”
She left me kneeling there again. I was shaking now and covered in a cold, thin film of sweat as she made her way back to my box of toys.
“You have so many fun things in here…” she mused, and I quivered in anticipation as I waited to see what she would choose to torture me with next.
I had a wide range of toys in there, and I knew she was cataloging each thing and using my collection to draw her own conclusions on what it was that I typically wanted during sex.
The thing was, I hadn’t used most of it in practice.
My tastes clearly leaned into mild degradation and sometimes crossed into light BDSM, but that was something you didn’t typically explore with a partner unless you trusted them.
Most of my partners assumed because I was masc that I was dominant, and I often did nothing to counter that assumption because I didn’t trust most people to tie me up or hurt me the way I so desperately craved.
But Cass had just… known. It was like she instinctively knew what I needed, and she was more than happy to give it to me. She’d just naturally fallen into the dominant role, and for the first time in my adult sex life, I trusted someone enough to lean into it.
So, when she pulled out a pair of handcuffs, only to immediately shake her head and put them back in the box, my heart sank in disappointment.
She must have seen the look on my face because she gave me a dark smirk.
“Not today, baby. Today, I want you to be good and listen because I tell you to, not because you have to. It’s going to be hard, but I know you can do it.”
“A-alright…” I stammered, and the disappointment I’d felt about her disinterest in the cuffs vanished as she pulled out a pair of fucking nipple clamps.
They weren’t exactly beginner clamps, either. They were lined with rounded teeth and connected by a thin silver chain that sparkled between her fingers as she carefully examined them.
“Perfect,” she murmured before making her way back over to me with that sinister little smirk back on her face.
“Let’s get these on you, then we’ll see how long you can last for your next round. How does that sound, baby?”
“Good… That sounds… So fucking good…” I panted, and she beamed at me before reaching out to gently cup my right breast so she could pinch my already aching nipple between the teeth of the unforgiving clamp.
The pain sparked and fizzed through me, and I arched my back involuntarily as the cold metal cinched down on my sensitive peak.
Another rush of wetness flooded my thighs, and Cass chuckled at my inability to hold still as she moved on to my other breast.
The dildo bumped against her legs as I ground my hips into nothing. The vibrator wasn’t even on, and my clit was throbbing so hard I didn’t know how I was going to make it through the next round of edging I knew she was going to put me through.
The second clamp bit into my other breast, and I cried out as the delicious pain tore through me, and my brain went temporarily blank.
Oh my god… Holy fuccckkkkk… That hurt so. Fucking. Good.
The chain of the clamps brushed against my sternum as I continued to mindlessly thrust my hips in an attempt to get some friction from the strap against my clit, but all movement stopped when Cass wrapped her hand firmly around the dildo and used it to hold me in place.
“Shhh. You’re alright. Stop moving. I want you to be still for me. Can you do that, baby?”
I nodded, even though I wasn’t sure if I actually could.
My entire body was a live wire, and the intoxicating mix of pain and pleasure kicked up a notch as she hit the button on the remote again.
My spine locked up in response to the intense burn of pure need that exploded from my core, and I let out a low, desperate moan as I fought the almost immediate urge to come.
Using the dildo as leverage, Cass forced the vibrator harder against my clit, and my hands flew to her hips in an effort to steady myself.
“No. Hands behind your back. Be still,” she reminded me, and my lust-drunk mind suddenly understood why her sadistic ass hadn’t wanted to use the cuffs.
The look of bored amusement she had on her face said it all as she calmly watched me struggle to do what she said for no other reason than she’d told me to do it.
I was gasping and moaning helplessly now as I gripped my left wrist with my right hand at the small of my back. Kneeling helplessly before Cass, I sniffled as she gently rocked the base of the dildo against the relentlessly buzzing vibrator.
“Mmm, such a needy little slut for me. Look at you. You fucking love this, don’t you?” she purred, and I whimpered and nodded.
I couldn’t use my words to answer. Speaking would take too much effort, and I needed every ounce of brain power I had to keep myself from coming before Cass told me I could.
“Are you my needy little slut, Theodora?” she hummed, and before I could try to even formulate a response, she tugged lightly on the chain between the clamps, and I screamed.
Laughing softly, she bounced her finger lightly on the chain over and over again, causing several intense, rolling waves of agony to explode through the abused tips of my swollen nipples.
The pain mixed with the unrelenting vibrations between my thighs and sent me shooting towards climax so quickly that I sobbed.
“Cass! I’m gonna come! Fuck, I can’t help it, please!”
I was desperate for her to take pity on me. I didn’t want to disobey her, but I was so close. There was nothing I could do to stop it from happening, so when the vibrations abruptly stopped again, I choked on a relieved sob, even though my entire body was screaming for some form of release.
Cass let out a deliciously condescending chuckle before brushing my now-damp hair back from my face.