I'd been messaging Kelly on and off for a little while through Craig's List, but we never quite managed to find the time to meet. Eventually, after some back and forth, I found myself home alone and suggested that tonight might be a good time, and I sent her my number. My phone buzzed almost immediately. I answered, and the voice on the other end sounded confused.
"Chris? Is that you?" she asked, a hint of disbelief in her tone.
"Yeah...?" I replied, matching her confusion.
Kelly let out a laugh, the pieces clicking into place on her end. "I thought I recognised the number. We've met before!" she said, still giggling.
It took me a moment to catch up. "Wait, seriously?" I asked.
She explained how, after saving my number, something felt oddly familiar. The moment she called, she realised exactly who I was. As it turned out, we'd met once for coffee at a Pret just off Oxford Street a couple of weeks before. It had been a casual meetup, nothing more than a friendly chat about a naughty project I'd been working on at the time.
"Well, now I know what you really use Craig's List for," she teased, her voice full of amusement. Kelly was replying to an ad I'd posted about being a willing guinea pig for women who wished to try their hand at dominating a submissive man.
I laughed along with her, caught somewhere between surprise and excitement because I already knew how attractive Kelly was, having met her in the flesh already. "So... how about tonight?" I asked, letting the question hang between us. "Absolutely," she said. We arranged a time for later that night. I hung up and excitedly waited.
Kelly was striking - tall, slim, and athletic, with a presence that naturally drew attention. Her smooth, dark skin contrasted with the sleek, straight cut of her short hair, framing her face perfectly. When she arrived at my flat, she didn't waste any time.
"Okay," she said casually, her voice taking on a soft but authoritative tone. "Can you get undressed for me?"
I nodded without hesitation and began stripping down, following her lead. Kelly made herself comfortable, settling against the headboard of my bed as she watched with quiet amusement. There was a mischievous glint in her eye, her gaze steady and assessing. She wore tight black jeans that hugged her frame and a thick black jumper, the fur trim on the shoulders giving her an effortlessly stylish edge.
As I stood before her, completely bare, Kelly's eyes slowly roamed over me, taking her time as if she were weighing her options. Her lips curled into a smile. "Alright," she said, still relaxed against the pillows. "I'm just working out what to do." She chuckled softly, acknowledging the newness of the experience for her.
The anticipation hung between us, and I could feel the excitement in the air. Despite her inexperience in the role, there was a natural confidence about Kelly that made the moment feel electric.
I was already hard, but when she shifted forward and began tugging at the waistband of her jeans, my cock twitched in response. Her movements were slow and deliberate, her hips lifting slightly as she peeled the denim down over her legs. As she wriggled the tight material past her thighs, she glanced up at me, catching my eye with a teasing grin.
"Are you going to go down on me?" she asked, her tone light but laced with expectation.
"Yes, miss," I replied, my voice barely above a whisper as I waited for her to free herself from the tangled denim around her ankles.
It took a moment - tight jeans were clearly not the easiest to remove gracefully - but eventually, Kelly kicked them off, leaving her in just the thick black jumper and woolly socks. She lay back against the mattress, swinging her legs up and spreading them effortlessly.
I needed no further instruction. Without hesitation, I crawled between her thighs, the warmth of her skin beneath my hands as I began to follow the unspoken cues she offered.
I pressed my lips to her, trailing soft kisses along her folds before drawing her clit gently into my mouth. My tongue worked in slow, deliberate strokes, shifting between teasing flicks and deeper licks, as I leaned into the familiar rhythm. I let my hands rest on her hips, steadying her as I lavished her with attention - gentle but eager, using every trick I knew to draw out her pleasure.
But barely thirty seconds had passed before Kelly suddenly sat up, her body shifting away from me. "Wait," she said, her voice firm but playful. "On your back."
I obeyed without hesitation, rolling onto my back as she moved with quiet confidence. Kelly wasted no time, straddling me and lowering herself onto my face. Her thighs framed my vision as she pressed her pussy to my mouth, beginning to grind against me with slow, deliberate movements. My tongue met her in kind, flicking and probing as she rode my face with an easy rhythm, taking what she wanted from the moment.
A couple of minutes passed, the warm weight of her body against me as I focused entirely on pleasing her. Then, without warning, I felt a sudden sting at the tip of my cock. I flinched beneath her, letting out a muffled moan of surprise as the sensation shot through me.
Kelly had spun around and casually flicked the head of my erection as it stood upright. Seemingly pleased with my reaction, she did it again - and again, each flick sharp enough to draw another muted groan from me, but I didn't let it distract me from the task at hand. I stayed focused, my tongue continuing to worship her as she tested the limits of my attention.
From my vantage point beneath her, I caught glimpses of Kelly as she shifted. I watched as she reached down and tugged the jumper over her head, revealing a black crop top underneath that clung tightly to her athletic frame. Her flat stomach was visible beneath the fabric, her small but perfectly shaped breasts peeking from the edges.
She flicked me three more times in quick succession, each one catching me off guard. The stinging bursts of sensation left me gasping softly against her, unable to see what she was doing behind her back but feeling every sharp touch.
Then, just as I was adjusting to her game, Kelly escalated. No longer content with playful flicks, she shifted slightly and brought her hand down hard against my balls. The slap landed with a jarring sting, and I flinched beneath her, letting out an involuntary grunt against her wet skin.
Her hips rolled against my mouth as if nothing had happened, but the sharp contrast between pleasure and pain left me breathless, fully immersed in the intensity of the moment.
Yet, despite the growing heat between us, Kelly suddenly shifted. Just as I was losing myself in her rhythm, she moved off me, her weight lifting as she knelt beside me. "Stand up," she instructed, the command clear and unwavering.
I did as I was told, curious about what she had planned next. I stood at the foot of the bed, still catching my breath as Kelly shifted into a seated position, facing me. She leaned back slightly, her eyes locking onto mine as she tilted her head with a curious smile. "Did you enjoy that?" she asked, her voice soft but expectant.
"Yes, miss. Very much," I replied, my tone sincere. Despite being slightly disappointed by the abrupt shift, I wished she had let me continue.
Kelly's smile lingered as she lifted her crop top over her head, revealing more of her toned, athletic frame. It was no surprise that the bra she was wearing beneath it was also black. "Wank for me," she said casually, settling comfortably against the pillows as she watched me.
I wrapped my hand around my cock, slowly beginning to stroke as her eyes remained fixed on me. Kelly shifted slightly, drawing her knees up and parting her legs just enough to reveal herself fully. Her pussy was neatly trimmed, the hair soft but well kept. I admired every detail - from her slender waist to the curve of her hips - and the quiet intensity in her gaze.
"You're very beautiful," I told her, the words escaping almost involuntarily.
Her expression didn't shift. "Thank you," she replied, her voice flat and emotionless, as if acknowledging a fact rather than accepting a compliment. Without warning, she raised her right foot and kicked me lightly between the legs, the thick wool of her sock brushing against my skin as her toes made contact with my balls.
The sensation was sharp but brief, catching me off guard. Before I could react, she did it again. Another quick, precise kick that sent a dull ache radiating through me.
I tensed but remained standing, keeping my composure as she watched carefully, her eyes scanning for any sign of weakness. Her gaze lingered on mine, testing me silently.
Satisfied, she raised her foot once more and kicked harder this time, the force of it enough to make me sway slightly. I gritted my teeth, feeling the intensity spread through me, but I steadied myself and stayed upright, meeting her eyes with quiet resolve. Kelly's lips curled slightly, the faintest flicker of amusement crossing her face.
Kelly didn't hesitate. She kicked me three more times, each one landing with the same measured precision, before her voice cut through the moment. "Stop," she ordered.
I immediately obeyed, letting go of my cock and dropping my hands to my sides. As the ache lingered, I glanced at her, noticing a slight shift in her expression, something coy, almost curious.
"Did you say you had a strap-on?" she asked. It was something we'd discussed in our messages, a suggestion I'd made in passing, wondering if she might be interested in trying it.
"Yes," I replied.
"Get it," she instructed, leaning back slightly against the headboard, watching me retrieve the bright pink silicone strap-on from the drawer where I kept my collection of secret things. As I attached the dildo to the harness, Kelly's eyes followed my movements with interest. I handed it to her, showing her how to slip into the straps and adjust them.
"Is that okay?" I asked, tugging at the buckles to tighten the harness around her waist.
She glanced down at herself, testing the fit before nodding. "Yeah," she said simply. Then, with that same cool authority, she added, "Bend over on the bed."
I climbed onto the mattress and positioned myself on all fours, lowering my chest while keeping my ass raised in the air, completely exposed for her. I heard the faint squirt of lube as Kelly prepared the toy, the cold sensation making me flinch when the tip pressed between my cheeks.
Kelly placed her hands firmly on my lower back, steadying herself as she bent her knees slightly and began to push the silicone shaft inside me. Her movements were careful at first, testing the angle, but she gradually found a rhythm, her hips rocking steadily as she drove the toy deeper.
"It's not very big," she remarked, a teasing note in her voice.
She wasn't wrong. Despite being nearly twice the size of my own cock, the strap-on was relatively small as far as these things go. But I didn't have much experience with this kind of play. Most of the women who had tried it with me before seemed to struggle with the motion, finding the angle awkward and unnatural. Kelly appeared to be encountering the same issue.
"Lift your ass more," she instructed, adjusting her stance. I complied, shifting slightly to give her a better angle.
But after another minute of thrusting, Kelly let out a frustrated sigh. "This is really shit," she said bluntly. Without hesitation, she unbuckled the harness, letting the strap-on fall limp as she abandoned the effort entirely.
Kelly climbed back onto the bed, stretching out and spreading her legs without a word. The invitation was clear. I didn't need to be told twice. I crawled between her thighs, lowering myself as I resumed my worship, letting my tongue explore her with renewed enthusiasm.
For a while, the room was filled only with the sounds of our breathing and the faint rustle of the sheets. Her hand found its way to the top of my head, her fingers curling lightly into my hair as she held me in place.
After about a minute, Kelly's voice cut through the silence. "Put some effort into it," she said, the calm authority in her tone unmistakable.
I hesitated for just a moment. I wasn't sure if she was simply leaning into the role of the demanding dominatrix or if she genuinely thought my performance lacked something. Either way, the comment hit harder than I expected. I'd always taken pride in my ability to satisfy women this way. If there was one thing I thought I could do without fail, it was this.
Swallowing the flicker of doubt, I pushed the thought aside and redoubled my efforts, letting my focus zero in on her clit as I worked with greater intensity. I adjusted my pace, trying to find the rhythm she wanted.
Thirty seconds later, her hand still pressing firmly against me, Kelly spoke again. "I'm not getting any pleasure from this at all," she said, her voice matter-of-fact. The words stung more than I cared to admit.
I paused briefly, but she didn't let me linger in my disappointment. "Move your tongue faster," she instructed.
I obeyed, increasing the speed, my tongue moving in quick, deliberate flicks. Still, she remained unresponsive - no subtle shift in her breathing, no change in the way her body moved beneath me. I tried to stay focused, but it was difficult to ignore the mounting frustration simmering beneath the surface.
"Move your face closer," she added, her tone carrying a hint of impatience. I complied, pressing myself against her, though I wasn't entirely sure how I could possibly get any closer than I already was.
A couple of minutes later, Kelly shifted slightly, her voice breaking the steady rhythm we'd settled into. "Do you want my ass?" she asked, her tone teasing yet matter-of-fact. As she spoke, she lifted her legs, granting me full access to the perfect curve of her backside.
Her body was lean and toned, but her ass was soft and shapely, a tight, round contrast that seemed designed to tempt. I didn't hesitate. I pressed my face between her cheeks, letting my tongue trace along the sensitive skin as I slowly began to tease her ass hole.
Moments later, Kelly rolled over and pushed herself onto all fours. The sight alone was enough to send a fresh surge of excitement through me - her arched back, the subtle sway of her hips, and the inviting curve of her ass being presented so boldly. I craned my neck, drawn irresistibly to her, and pressed my face between her cheeks once more, resuming my worship with renewed enthusiasm.
She responded with a soft shake of her hips, the movement playful as she ground herself against me, causing my head to shift slightly with each roll of her body. My tongue circled her ass hole, teasing and exploring as she encouraged me wordlessly with the way she moved.
Her hand found its way to the back of my head again, her fingers curling into my hair as she pulled me harder against her. The pressure of her palm guided me, pressing my face firmly into her until I could feel the full weight of her body against me.
Then, with the same effortless dominance she had shown throughout the evening, Kelly's grip tightened on a tuft of hair at the top of my head. She tugged me back just enough to pull my face away, holding me in place with a silent but commanding authority. With that same control, she guided my head downward, tilting it until my nose was nestled directly between her cheeks.
Before I had time to process the shift, a sudden, sharp fart escaped her. short and unapologetic. It wasn't something I had expected, but neither was it something that was going to stop me from worshipping her ass. I allowed my tongue to dart straight back in.
"Faster," Kelly ordered, her voice low but firm.
I obeyed immediately, increasing the speed of my tongue as it flicked and circled, tracing along the edges of her tight hole and dipping inside with every motion.
After a while, Kelly shifted her weight and gave a simple command. "Get underneath." Lifting one of her legs, she gave me just enough room to roll over, settling back into position beneath her. She lowered herself onto me, pressing her pussy firmly against my mouth once again. My tongue found her instantly, tracing her wet slit without hesitation.
"Wank yourself while you lick me," Kelly instructed, her voice calm but expectant.
I reached down, wrapping my hand around my cock, already hard and throbbing. As I began stroking, I tried to keep my focus entirely on her, determined not to let the sensation distract me from making her cum.
Moments later, Kelly leaned back slightly, lifting herself just enough to bring her palm down in a sharp, flat slap against my balls. A groan escaped me at the sudden burst of pain, but she didn't pause. A second strike landed seconds later, intensifying the ache that spread through me.
"Slower," she said, her tone firm but measured. It took me a moment to process - was she referring to my tongue or the speed of my hand? Before I could adjust, she clarified. "I said wank slower," she repeated, punctuating the order with another hard smack to my balls.
I immediately complied, adjusting the rhythm of my strokes while keeping my mouth locked to her. Kelly's hips began to grind harder against me, her movements pressing into my face as her breathing grew more ragged.
I was so focused on her that I didn't realise my hand had slowed to a stop entirely. Kelly, however, noticed immediately. Her palm connected with me once again, the sharp sting sending a fresh wave of sensation through my body.
"I didn't say stop," she said coolly, her grip tightening in my hair as she held me against her.
I resumed at once, my strokes deliberate but steady as I fell back into the rhythm she demanded. Each slap, each order, only heightened the intensity of the moment, leaving me fully absorbed in the task of pleasing her while keeping my own pleasure carefully in check.
"Keep going," Kelly instructed as she climbed off my face, her voice calm but unwavering.
I obeyed without question, continuing to stroke myself as she moved around the bed. Now at the foot of the bed, without warning, her hand came down hard against my balls, sending a sharp jolt of pain through me. I gasped but kept my strokes steady, knowing better than to falter.
Kneeling at the edge of the mattress, Kelly reached for the discarded dildo from the strap-on, her fingers wrapping around the cool silicone. When I felt the cold tip against between my ass cheeks, I obediently arched my back slightly, lifting my hips to grant her better access.
A moment later, with ease, she slid it inside, working it in slowly before establishing a steady rhythm, thrusting the toy in and out of me with purposeful movements. Occasionally, she paused just long enough to land another sharp slap to my balls, the combination of pleasure and pain sending conflicting signals through my body.
"Slower," she said, her gaze fixed on me as she continued.
I immediately adjusted, reducing the speed of my strokes, but she wasn't satisfied. "Much slower," Kelly added, her tone dropping as she emphasised the words.
I complied, my hand barely moving as I teased myself with the lightest, most agonisingly slow motions. The desperation in my cock grew, each slow stroke leaving me aching for more. Meanwhile, Kelly maintained her rhythm, her grip firm on the dildo as she pushed it deeper, occasionally punctuating the moment with another slap to my balls.
Every so often, I felt my hand involuntarily pick up speed, the desire to finish overriding her instructions. Each time, Kelly's voice cut through the haze. "Slower," she reminded me, reinforcing the command with a quick, deliberate strike between my legs.
Eventually, she gave a new order. "Stop wanking," she said, her voice soft but final.
I released my cock immediately, though the throbbing ache persisted. My shaft twitched helplessly above my reddened, stinging balls as Kelly continued to fuck me with the dildo, showing no signs of stopping. Her palm met me again and again, each slap leaving a lingering heat behind.
Minutes passed, and finally, Kelly withdrew the dildo from my ass. "I want to pee on you," Kelly said, the words calm but deliberate. She added, "Do you need to put some towels down?"
"Yeah, I can put towels on the floor," I replied, my voice steady despite the quickening of my pulse. I crossed the room to retrieve a large beach towel from the drawer, folding it over several times before spreading it on the floor. Once it was in place, I lay down with my head resting in the centre.
Kelly stepped over me, squatting carefully above my face. There was always a mix of excitement and apprehension in moments like this. It's just about the most degrading thing Kelly could do to me, and a real test of my submission to her.
I tried to steady my breathing as she settled over me once more. For a while, she simply continued her playful torment, her palm finding my balls again with deliberate slaps. Each one made me twitch beneath her, a sharp reminder of the dynamic we were locked in.
Her body pressed down slightly, holding me in place as she moved with ease, shifting her weight just enough to assert dominance without a word.
Then I felt the first drops of her hot, bitter piss on my lips and did my best to wriggle into the correct position to take it in my mouth. It was slow and steady enough for me to swallow drop after drop, although the task was made hard by the smacks to the balls, each of which caused my body to jerk.
Without waiting for permission, the excitement overwhelmed me, and I let my hand drift down, stroking myself as the moment unfolded. Kelly didn't tell me to stop, so I continued to jerk off as I swallowed her hot piss and endured her stinging smacks to my balls.
In between jets of piss, Kelly bounced on my face, her wet pussy smothering me, covering my face with her piss, which was now running down my cheeks. I wanked furiously as Kelly force-fed me her hot nectar over the course of several minutes, jet after jet, drop after drop.
Eventually, her voice cut through the sounds of my ragged breaths and the wet heat between us. "Make yourself cum," she ordered, her tone soft but commanding. I responded instantly, my grip tightening as I stroked harder, chasing the inevitable release.
Kelly's movements also grew in intensity. She smacked my balls more and started bouncing and grinding more forcefully against my wet face, spreading her wet piss over my entire face.
As Kelly delivered her last few drops into my waiting mouth, I let out one final gasp, I let go, and finally shot my load up into the air. Kelly slowly climbed off, leaving me breathless on the towel beneath her.
Kelly stood over me for a moment, watching as I lay there, breathless and spent. Her eyes scanned my body, her gaze lingering briefly on the mess I had made across myself and the towel below. "You did well," she said eventually, her tone soft yet assured, as though offering a final verdict on the night's events.
I smiled faintly, still catching my breath. "Thank you, miss," I replied, the words instinctive.
