I tapped the crop against my boot lightly – tap, tap, tap – as I contemplated what to do next to his ass. Tap, tap, tap. I stared out the window stroking my fingers over his cheeks, his balls, pressing a slender finger gently and just barely in and out – in and out of his tight asshole. The movement soothed me and the muffled sounds of the moans he was trying not to make were relaxing.
I wanted a sip of my Old Fashioned but I only had two hands. Which to give up? I decided on the crop, delivering two more stinging slaps to his already red cheeks. I might have been inclined to feel sorry for him as his body bucked, but in truth we both loved this.
With my drink in one hand, long lean legs clad in black leather over-the-knee boots, I stretched out in the chair I’d placed next to the couch… the couch where he was currently bent over the arm, legs spread in wide stance, blindfolded and ball gagged. For good measure his hands were bound behind his back. It was a beautiful sight. I rested my glass on my flat stomach and appreciated the contrast of the amber liquid against my pale skin and the lacy, black boy short panties I wore. I dipped a finger into the icy cocktail and drew it slowly over his asshole, watching a few drops of cold liquid trickle toward his balls. This suddenly seemed like an excellent game to me. I did it again and again until he was squirming and the first drop of liquid fell from his balls onto the floor. Bingo.
I got up and moved to crouch behind him, ducking my head down to suck the bourbon off his balls, trailing my tongue upwards to his asshole. I finished what was left of my drink and tucked the remaining ice cube in my cheek. I took both hands and slowly spread his ass, blowing a tiny breath over his wet hole and watching his body’s involuntary reaction to the changing sensations. Placing my mouth on him, I teased him with my tongue, round and round over that most sensitive skin. I held him still, hushing him, then thrust my cold tongue as deep into his asshole as I could. He let loose a string of muffled cries and curses, as intoxicating as my Old Fashioned, while I penetrated him repeatedly. I fucking loved tonguing his hole. Once I got started I didn’t want to stop until my tongue was tired. I needed more.
I could tell he was in heaven, but I didn’t want him getting too comfortable. I pulled back to his groaning objections and gave us both a moment to catch our breath. Standing up, I gazed down at his now very wet hole and watched him control the shaking in his body. So many choices of what to do next.
I didn’t want to rush this. I was having too much fun torturing him. I stepped away and spotted his drink still halfway full on the desk. I helped myself to it and returned to my chair, stroking his ass, his balls, his cock. I had promised to punish him for something that had slipped my mind at the moment, and that drove my decision. I calmly explained the situation as I popped open the container of lube right by his ear. I knew he could hear it, could hear how much I was squeezing into my hand. He once teased me that I held the lube in my palm as though it were something precious. I thought of that as I swirled the fingertips of my other hand in it then placed the first one against his hole.
Relaxing in my chair, my legs kicked up on the couch near his head, I knew he could sense – could smell from the leather of the boots – that I was getting comfy. This could only mean I was settling in for lengthy play. I slid each finger in quick succession over his hole, in the way one might drum their fingers on a desk. Over and over, getting him used to the rhythm. Then abruptly I slid the tip of my first finger into his hole, deeper than I had at first, but only just past the first ring of muscle. In and out. In and out. Switching fingers I played like this, drinking his cocktail and watched him react. As I knew he would, he started pushing against my hand for something more, something deeper.
On the next finger I slid in, I stopped and just barely moved it side to side. He was pushing his ass against my hand in a greedy way. I stilled for a moment then ever so slowly pressed forward, deeper until I was up against his second muscle where I stopped for a beat. I saw him holding his breath. A second later I pushed further and breached the second ring, watching his entire body seem to exhale. Lovely.
I drew my finger back into the space between then pressed forward again. Then I slid it all the way out and back in again. I played this game with each of my fingers as I finished his drink, loving the way his ass kept trying to fuck my hand. Realizing I was ready to take things up a notch, I stood up to set down his glass and grab what I would need next.
I stepped away and asked if he was doing ok. He nodded and said what sounded like a yes but came out like a moan of pleasure. I unzipped the go bag and pulled out my harness and 2 dildos – one medium and one large. I slid off my panties and draped them over his face, knowing the smell of my arousal would drive him crazy. I was right. Although muffled there was no doubt he was asking to taste me. I ignored him and stepped into the harness, securing it in place with the smaller of the two dildos.
Seizing my last chance, I knelt and tongue-fucked his asshole over and over, and over and over again. When I was finally satisfied I had enough, I bit each cheek hard enough to leave a mark as he cried out in surprise and possibly a little pain. I lubed up the dildo, dribbled a bit more down his crack, then coated 2 fingers and my thumb from tip to palm. I checked that the camera was on and hit record.
I could see his beautiful ass filling the screen and I told him I was rolling. Reaching out, I pushed my thumb against his asshole slowly all the way in as deep as I could go. He began to moan. I withdrew my thumb then placed both fingers against his hole. He was saying something that sounded like oh fuck as I slid them both in and began to slowly scissor them, stretching him and getting lots of lube in there. When I could feel his muscles begin to relax, I pulled back my fingers and stepped forward to press the end of the lubed up dildo against his slippery hole. Ever so slowly, I slipped the head of the dildo inside him.
He began pressing against me for more. I grabbed his hips and stopped his movement. I asked him if he wanted me to fuck him. He said yes. I asked if he was going to beg but he was silent. I slid the dildo smoothly in until my hips were pressed up against his ass. I gave him a couple of micro thrusts then pulled almost all the way out, leaving just the tip in him. I asked if he wanted more and got yes in reply. I gently fucked him for a bit then pulled out and turned off the camera. Time to take it up a notch.
I grabbed the large dildo and lubed it up. Using one hand to spread his hole, I slid the big dildo in about two inches. His body tensed and he kept saying fuck, fuck, fuck. I twisted it slowly left and right. Laying down more lube on the shaft, I pressed it in a bit further and let his body get accustomed to it. Then I slid it out and heard him curse. I asked if he was ready to beg now and saw him nod. With an evil grin, I slipped the bigger dildo into my harness.
Coating my hands with lube, I began stroking his cock and balls. His breathing was getting heavier. I lined up the large dildo and slowly, deliberately pushed until it was buried fully in his ass. He was making feral sounds and I unbound his hands. Threading my fingers between his, I lifted his hands over his head as I lay my bare chest and stomach onto his back, pressing my breasts against him. And like this, I began to fuck him. Small, short movements and long deep strokes. Both of us finding nothing but blissful escape in the act. Letting go of his hands, I slipped one arm under his chest and reached my hand down to stroke his cock. He wasn’t going to last much longer.
As I listened to his moaning and faster breathing, I knew I had the right rhythm and angle. I kept fucking him and stroking his cock, pressing down on his back to prevent his hands from stopping the intensity. His body began to tense. I leaned down to nip his ear and told him to cum. With that, I felt his body shake as his warm cum flowed over my hand.
I stroked him until he was trying to shake his head, begging me to stop. I went still except to unbuckle and remove the gag, then pull down the blindfold. As he blinked and tried to get accustomed to the light, I slid out of his ass to a string of fucks. I removed the harness and stepped into his line of sight naked but for the boots. Once he could focus, I crouched down in front of him with my knees spread so he could see how wet I was. And with an evil grin, I licked his delicious cum off my hand.
Source: reddit.com/r/eroticliterature/comments/kswp88/fun_playing_with_hism_ass