I'd been pestering her for what felt like an eternity. We've always enjoyed the kinkier side of things and there's not much left for us to try, which made this all the more alluring, more enticing, exciting... enthralling. But there's a lesson to be learned in earnest here - be careful what you wish for.
Truthfully things had dragged on for so long that it seemed little more than an elusive fantasy, never quite materialising into tantalising tangibility. That's why when she told me to prepare myself for a night like no other, I foolishly dismissed her warning as hyperbolic. But boy was I wrong.
She'd given me her forewarning of a night beyond the ordinary earlier in the day and - after a frantic Friday finalising some projects at work - I'd largely forgotten about it. And then the first message came:
"For the remainder of the weekend, you belong to me. You're nothing more than my personal fuck-toy, to be used abused for my amusement. When you get home, venture upstairs to the bedroom. You'll find further instructions waiting."
Nothing especially unusual about this; we both enjoy Female Domination from time to time, and she always likes to start things off on the right footing from a submissive mindset perspective. Nevertheless I was excited to see what lay in store, and rushed home - eager to learn more.
When I stepped through the door, kicking off my shoes at the threshold, my mind began to race with thoughts and deductions as to what the weekend would hold. Rushing up the stairs and into the bedroom, my heart began to race as quickly as my mind - she'd never done anything like this before.
On the bed laid an outfit. Not a man's outfit. There was a matching bra and thong set - a red and black lacy number - and beside that a large glass butt plug and small bottle of lube. As promised, there were instructions on the nightstand:
"My little slut. Don't you think it's important to dress the part, if you've any hope of playing it? Lube up your filthy hole, insert the plug, and dress in the pretty little outfit I've laid out for you. Naturally I want to see a picture when you're looking a little more delicious. Don't rush - I want you to feel like the sexy little whore you are".
We've dabbled in a little crossdressing before, having been forced to wear ladies underwear beneath my clothes when we're out in public, but never a matching set with a bra, and I'd never been brave enough to take pictures before.
Lubing up one finger and slowly tracing my index finger around my asshole felt incredible, and my manhood responded in kind - leaking precum in a way it hadn't leaked for ages. After what felt like an eternity, I slid my finger inside and let out an involuntary moan. No sooner had I inserted one finger than I found myself aching for the feeling of fullness I'd only ever encountered during our pegging sessions. Quickly I slid in a second finger, and then a third, working the lube inside my asshole in anticipation of taking the large plug.
Regretfully I stopped playing with my ass, applied lube to the glass plug, and began inserting it into my now-loosened hole. The cold of the glass pressing against my ass felt sensational, but this was a plug larger than any I'd inserted before, and I struggled to get it past the widest point. After a little persuasion, my greedy ass eagerly swallowed the remainder of the plug, with the base resting firmly against the entrance to my slutty hole. I took a picture to send to Mistress before I proceeded to dress in the prescribed attire - quite the sight, having the inside of my asshole exposed through the glass. This did nothing to alleviate the aforementioned leaking.
Slowly sliding the panties up my legs my little cock began to twitch and grow, making it impossible to deny how much being made to dress in women's slutty clothing was turning me on. Finally the soft fabric rubbed against the head of my cock, making it twitch violently. There's really nothing that can make a man feel sluttier than the fabric of a thong being pulled tight into your ass. It's not something most men often experience, and it's a constant reminder of your submission. Snap - another picture for Mistress.
Now for the bra - something I'd never put on before. Fortunately it was already fastened, and I hastily wrapped the straps around my arms and up over my shoulders, hoping to minimise the shame and embarrassment that I was feeling. After straightening the straps, I begrudgingly took another picture for Mistress, but oddly this time, I felt like taking more - putting on a show even. Pushing my peachy ass out and my chest forwards, I took a picture of the panties from the back, making my ass look as tempting as possible, and a similar picture from the front, with the most sultry look I could muster. I was certainly dressed like a slut, and beginning to feel like it, too.
After sending the pictures as requested, I was flooded with a sense of shame and regret; those pictures were permanent evidence of who I really am.
"Mmm, you filthy fucking slut" she rapidly replied. "Don't worry, there's plenty more in store for you yet. We're heading out tonight, so get dolled up - don't worry, you can pretend you're a real man and wear jeans and a nice shirt. I'll be home soon".
Waiting for Mistress to return felt like an eternity. What on earth could we be getting dressed up for? Well, fortunately my wait eventually came to an end. Surprisingly, when Mistress entered the house she was already dressed for the evening - clearly she's in a rush to get wherever it is that we're going.
"I'd imagine by now you're desperate to know where we're going? Well don't worry, this is the least desperate you'll feel tonight; we're going to the swinger's club - they're having a very special night tonight" she said with a telling smirk. "You're forever hassling me to test your limits, and tonight we'll be doing just that. I sincerely hope you're ready". And with that, she ushered me into the taxi waiting outside, and off we went - venturing into new territory.
When we arrived at the club, I noticed that a lot of people had already dressed down, and in particular the men. Once again my heart began to race, worrying that I'd be asked to strip down to reveal my slutty layer beneath.
"Let's get a drink at the bar" she suggested, as casually as she might suggest ordering pizza, as if this situation were in any way ordinary.
One drink quickly turned into two, to three, and then four. We'd been talking with a few couples, and a couple of single guys, which led to my forgetting about the whorish outfit beneath my clothes. I may have been nervous about what was coming, but at least the people we'd been chatting to seemed nice.
"So you're probably wondering what the 'special night' I mentioned is all about, aren't you my little slut? Well, tonight is the night you finally get your wish granted. You'll have your fill and then some. All those times you begged me to find you a cock to suck, to force your head down on it, to be made to take a guy's load. Well, slut, tonight's the night".
And with that, she whisked me off into a large private room, and slowly closed the door behind her.
"This is your last chance to back out. After this, I will make all your dreams and fantasies come true. Those limits of yours wont be pushed - they'll be obliterated. You'll never be the same again". There was a seriousness to her that I'd never seen before - she really wasn't joking. She was finally going to make me suck another man's dick for her.
"I'm so nervous... I... I didn't expect this to ever happen... but I want to experience it... so badly" I stammered. "I want to be your filthy cock sucking slut".
"Don't play coy with me, you dirty little whore, that was just the tip of the iceberg. I've seen the porn you watch. I know which subreddits you follow. Tonight we're playing cum-dump catchup. All that time wasted. All those loads never swallowed. You're in for the ride of your life" she stated suggestively.
Before I'd even had a chance to process what she'd said, there was a knock at the door.
"Here, you'll be needing this" she said absent-mindedly, as she retrieved a piece of fabric from the band at the top of her stockings. Tossing it over to me, she gestured for me to use the fabric - a blindfold, as it turned out - whilst she headed towards the door. "Strip into your sexy underwear, put on the blindfold, and get onto the bed. Face down, ass up, like only a true slut knows to do".
Doing as instructed, a cocktail of thoughts and emotions overcame me. Was it excitement I felt? Shame? Maybe simply nerves? All I know for sure is that it was a rush - I huge rush like I'd never felt before.
The door opened, and I could hear whispered exchanges between Mistress and strangers. Perhaps it was one of the couples from earlier. Was I about to put on a show for a complete stranger whilst satisfying her husband?
Finally the door closed, and all that was left was a lingering, nerve-wrecking silence. Clearly whomever was in the room with us took equal delight in my panicked writhing. And then I heard the footsteps approach the bed.
"Open your mouth, whore. You've got work to do" Mistress demanded sternly.
Doing as instructed, my cock began to twitch and dribble precum even more than it had previously, soaking the front of the thong and creating a very visible wet patch.
"Haha, the dirty little slut can't wait to suck a hard cock" I heard a stranger say. It must've been the male half of the couple, but before I had a chance to process further, I felt it. The hard-yet-soft, warm head of another man's cock pushing it's way past my lips, and into my waiting mouth. And that's where he left it, letting me savour the taste and the feeling of dick in my mouth. My own cock twitched again in my panties.
Mistress giggled "see, I told you he was a natural born cock sucker - look how much it makes his pathetic little dick twitch". She'd never been mean about my cock before, and I knew it was an okay size, but I was shocked to find my little cock twitching even more in reply. "Fuck his face - let him feel a real cock for once", Mistress ordered. It didn't take much encouragement for the stranger to get to work. Slowly at first, rocking his hips back and forth giving me ever more of his marvellous manhood to savour. Before too long, he had found the back of my throat with his powerful phallus, and showed no signs of stopping - I had no idea if I'd be able to take it any further, but damn if I didn't feel slutty enough to try. To my surprise, I found myself pushing my head down onto his cock willingly, and it slid down my throat with relative ease - maybe I really am a born cock sucker I thought, as tears began to form at the corners of my eyes. Almost as if the owner of this delicious dick could sense my enjoyment, his pace quickened and he began to fuck my face with vigour, extracting not just tears from my eyes, but drool from deep within my throat as well which clung to his cock as eagerly as I was.
This went on for longer than I thought I could manage, and yet not nearly long enough, before I heard Mistress say "shove your cock down his throat, and hold his head there until I tell you otherwise".
With that he withdrew almost all the way out of my mouth, allowing me only a fraction of a second to gasp for air as he quickly and forcefully returned his cock to its rightful place deep in my throat.
"One" Mistress chimed.
"Two".
"Three".
Does she know I didn't manage to take in much oxygen before he gagged me with his cock, I wondered.
"Four".
"Five".
I could hardly breathe and had involuntarily began to push away from him, only to be forced back further, taking his cock to the hilt so that I could feel his balls against my chin.
"Six".
"Seven".
"Eight".
The edges of my vision began to blur, and I could feel my body sinking ever further into his, so that he was supporting much of my weight. Bizarrely my panic had subsided somewhat, giving way to what can only be described as a send of euphoria.
"Nine".
"Ten. Okay, let the slut breathe".
Withdrawing his cock from my throat caused me not only to gasp, splutter, and clamour for air, but also to long for the feeling of fullness, and of ultimate submission that I'd just endured... or rather enjoyed.
"One hole down, one to go. Let's see which is the greediest" I heard Mistress declare as I felt hands spreading my ass and another pulling at the plug. Almost as if in fear, my ass clung to the plug as it was being withdrawn from within me, and whomever was withdrawing it seemed to be in no hurry, letting my asshole stretch around the widest point for several seconds before removing it entirely.
I'd watched hours and hours of bisexual porn of different flavours - from forced bi to cuckolding to straight gay sex and until tonight had no idea that Mistress was aware of it, but I'd never really considered that I'd actually take anything other than her strapon. At least I'd had practice I thought sarcastically.
Things escalated quickly from here. Clearly my face-fucking which had left my chin covered with drool, dripping onto the bed, was only the warmup for the evening's festivities.
"Fuck his ass" were the only words spoken by Mistress to green-light taking my anal virginity. It was nonchalantly uttered, with perhaps even a hint of callousness in her voice.
Peeling my panties to the side, I felt the head of his cock at the entrance to my asshole, slightly agape from where the plug had stretched my out for the past several hours. It must've looked inviting because he wasted no time in applying pressure, threatening to enter my slutty hole with the head of his cock.
Fear of what was about to happen lead me to open my mouth in protest, but no sooner had I begun to utter words pleading for mercy than I felt a familiar-but-not-the-same feeling against my lips. It was another cock. But Mistress only let in a couple, didn't she? How did I miss this? He'd been silent this entire time, watching me get face fucked and abused, getting harder with each thrust he witnessed. Who was in the room now?
I had no time to dwell on it - they weren't being gentle any more; that time had passed. Almost in perfect unison, I felt the head of one cock push past the resistance of my well-loosened ass as the other stifled my cries (or were they moans? I was cock-d*unk and couldn't tell).
For every inch of cock I took in my ass, an inch was fed down my throat. If you'd told me that this was somehow one person wielding both members I'd have believed you, because they fucked me with the precision of a philharmonic orchestra, and I knew precisely who the corrupted conductor was. Being airtight for the very first time was by far the sluttiest and most submissive I'd ever felt, completely at the mercy of two strangers that I could nether see nor protest against.
"Look at his little cock wiggling around as he's fucked by two studs" Mistress sniggered. The two guys laughed. My heart sank. I was nothing more than a piece of meat to be used; their plaything. "Pick up the pace boys - this filthy whore has a busy night ahead".
Clearly they knew something I didn't, as simply hinting at what else was coming was enough to, well, get the guys coming. There was an unmistakable hastening to the thrusts from the guy in my ass, accompanied by an intensifying of his animalistic grunts; I knew he was about to cum, and I just wished that I was able to speak so I could beg him for his load.
A few seconds after he went from fucking my ass to pounding it, he let out a long, deep groan followed by a series of expletives as he unloaded inside me. Honestly I didn't believe I'd actually be able to feel his cum, but the warmth and extra sense of fullness was unmistakable. That was it. That was the moment Mistress was talking about when she said I'd never be the same. I've become nothing more than a cumdump - and I loved it.
Savouring the sensation of a hard cock pulsating in my asshole, emptying the last of his superior seed inside of me, I became aware of the fact that my mouth was now empty, and in between my moaning and panting, I was also speaking. "Thank you, thank you for fucking my ass, thank you for filling me with your cu..." I was cut off mid-sentence as I felt a strange tapping at the blindfold, and then another. Just as my mind had ascertained the origins of the sensation, my lips confirmed it: warm, salty cum splashed across my face, on my cheek, my lips, and into my open mouth. Instinctively I closed my mouth to keep this strange liquid out, but this instinct quickly gave way to a far deeper, more carnal one and I opened wide and extended my tongue, catching as much of my well-earned (and delicious) reward as I could.
It seemed I'd caught the majority of it on my face, as disappointingly little found it's way into my waiting orifice, forcing me to lick widely around my lips to collect as much of his seed as possible.
"Don't worry, you cum-hungry cock whore, there's plenty more to come" reassured Mistress, "you'll have a belly full of spunk in no time".
Had I not endured enough I wondered? Having gone from never experiencing a cock in my mouth, to being airtight, to taking a hot load of sticky cum at both ends. Apparently not, as I heard the door open and Mistress beckon in the next wave. I couldn't quite make out what the men said to each other, but it was enough to elicit a hearty laugh from each of them, and they couldn't leave without saying goodbye. One of them grabbed my balls and squeezed hard whilst leaning in to whisper "you don't need these any more, slut", and the other collected the precum from my leaking sissy clit before rubbing it across my lips and teasing "is this what you were after, you fucking whore?", as if I hadn't been degraded enough.
At least the worst was over. I'd taken cock and cum in both my holes. I'd gagged on cock. My ass was stretched, and I could feel cum slowly sliding down from my ass and onto my worthless balls. Whatever happened next, I'd experienced it before already. Or so I thought.
"Well I think it's safe to say that you really are a born sissy cock-sleeve, aren't you?" pondered Mistress. "You might as well just embrace it. You're going to please the next two fine gentleman, aren't you, slut" she quizzed.
"Y... yes Mistress" I replied meekly.
"Good, I'll be back soon; I need a drink after all this excitement" she exclaimed as she left me alone with two more strangers.
As the door clicked shut, one of the men spanked my right ass cheek hard, and I couldn't help but yelp in pain. "You're ours now" one of them warned.
Before I had a chance to reply, I felt skin pressing against my face, but couldn't make out what was happening. There was a feint musky aroma, and a slight prickle of fine hair. No. No it can't be. Was this guy forcing me to lick his asshole? To rim him? This is too degrading, it's too much. As I went to protest against this latest insult, I felt another sharp smack on my ass.
"Lick his fucking ass, get in there deep or I'll spank you until you do" admonished the other man.
And so I got to work - reluctantly at first, but as with everything else I'd experienced so far, the more I did it the more I enjoyed it, and the more I craved it. Soon I'd gotten so engrossed in eating this alpha's ass and listening to his moans that I'd all but forgotten about the other guy. That is until I felt his cock at the entrance to my ass, and it was far thicker than the guy who'd fucked me before. At first I didn't think it'd fit, but he was relentless - adamant that I was to take him to the hilt, and his persistence paid off. With a painful thrust, I felt my greedy hole engulf the first couple of inches that he had to offer, simultaneously backing up onto him to take even more. The recipient of my rimming did not take kindly to my distraction, spun around, and spat directly in my face before thrusting his cock straight to the back of my throat in a single, aggressive thrust.
Again it began. Less synchronised than the last two - this was primal, animalistic, rough fucking, the kind that leaves you dizzy and breathless. Fortunately they didn't last as long either, which was a blessing considering the burning sensation in my ass. Quickly the cock in my ass exploded, adding to the load left there earlier, and soon after the man who's asshole I had become all too familiar with grabbed my head and forced me down to the base of his cock, ejaculating directly down my throat and into my stomach.
Withdrawing their still-hard cocks from my battered holes, all three of us were panting in ecstasy. Cum was still attached to the cock I'd just been sucking, which I simply couldn't resist lapping up from the head, sporadically running my tongue down his shaft and back up to the tip. The sensation must've been too much because he bucked and pulled away, having his place taken quickly - and to my horror - by the man who'd just ravaged my asshole. By this point I'd accepted my fate. A slutty cum receptacle for superior men to use as they wished. I opened my mouth to swallow his cock and taste my sissy pussy, which evidently turned him on immensely as he grew harder in my mouth. Sucking relentlessly, channeling everything I'd ever learned from watching women suck dick in porn, it didn't take long before he was exploding again - this time filling my mouth. As he withdrew for the final time, cum spilled out of my mouth and down my chin, which he kindly scooped back up for me to savour. With the action over, I regained some awareness of my surroundings. When we first came into the room there was silence. A silence which terrified me. Now there was the incredibly sexual and unmistakable sounds of climax from the room next door. I bet they aren't being degraded like me, I thought.
These guys had been considerably less polite. Far from the gentlemen Mistress had referred to them as. She re-entered the room as they left it, closing the door behind them. Revelling in the sight of cum all over my face and dripping out of my now-gaping asshole, she laughed coyly. "Well, how was it my pretty little cum-glazed sissy?" she asked with a devilish expectancy in her voice.
"Thank you Mistress. You gave me everything I ever wanted and more."
"You're welcome. And you've been incredibly well-behaved - I think you deserve a reward" she praised. "I'll tell you what, I'll let you cum if you agree to eat my pussy".
Eagerly I agreed, and flipped over onto my back (which only hastened the steady flow of cum leaking from my asshole) ready to uphold my end of the bargain.
"Well" she said, "thinking about all the filthy things I've seen you doing for me got me very wet. Would you like to see for yourself?" she enquired as she headed over to the bed.
"Yes! Yes please Mistress" I blurted out. She removed the blindfold, lowered her panties, and positioned herself above my face, just out of reach.
"Good, I'm glad because I'm very, very messy down there" she replied.
She wasn't lying. Her pussy was swollen, glistening in the dim red lighting of the room. Those gorgeous lips encasing her delicious pussy were coated thickly with grool, a strand of which was dripping towards my waiting mouth. Hungrily I raised my head to catch the strand of grool as it fell, letting it fall into the back of my well-stretched throat, before burying my face entirely in her soaking wet pussy, licking with a yearning like I'd never felt before.
"Haha. You really are a filthy boy aren't you?" she cackled.
Unable to reply with my face smothered by her womanhood, I delved my tongue ever deeper. Her grool was thick, sticky, and delicious. It was a familiar taste which I loved.
"Don't you recognise the taste, honey? My pussy is so wet because I've just been fucked by a real man in the room next door when I went out for a drink. All this got me so worked up that I just couldn't resist" she confessed. "Thing is, I just couldn't let you have all the fun and dragged in the guy who came all over your face" she continued. "You were so eager to taste more of his cum that I figured you deserved a second helping, so I let him fill up my pussy for you; how does it taste, slut?" she asked gleefully.
There's no point in lying. Even if I wanted to, the fact that my cock was now rock hard belied any words of protest I could utter, and she'd seen the effect it had on me.
"Oh my, you're getting hard at the thought of me being fucked and filled by another man?"
It's true. I was. I relished the thought of her being pounded next door whilst I was being used by two strangers. She lifted herself off of my face, and I caught a glimpse of the wide grin spreading across her face; she was loving this.
"Well, a deal is a deal - I'll let you cum".
With that, she pulled my legs over and above my head, and began furiously jerking my rock-hard cock. Unsurprisingly, I lasted a whopping 17 seconds before I was begging her not to stop. I didn't even care that I was about to cum all over my own face - it was covered in another man's cum already after all.
Just as I was about to explode, she stopped playing with my cock and instead further doubled my legs over my head to point my cock directly into my mouth. Without even thinking, I opened wide as the ejaculate from my ruined orgasm spurted directly down my throat, slightly coating my lips and face. It was agonising not to have the release of orgasm - especially after all I'd done for Mistress - but at least I was cleaning up my own pathetic mess, and boy was there a lot of mess to clean. Twelve long, thick ropes of cum filled my mouth causing me to cough and splutter, choking on my own cum. Like a good little cumslut I gulped it down with delight.
"What do we say?" Mistress prompted.
"Thank you, Mistress" I replied, voice coarse from the abuse my throat had taken.
"Good. Slide your panties back into place and get dressed. You deserve a drink".
After doing as requested, we headed back out to the bar - my face still covered in cum, and the last of the seed in my ass soaking into the dark fabric of the panties. As we left the room, we were greeted by a sizable crowd of people, cheering and clapping at us. But what were they cheering for? The room wasn't big enough for more than the four of us at any one time, and Mistress couldn't possibly have told them all - especially whilst she was busy being filled with cum in the room next door.
And that's when I saw. The room on the opposite side to where my Mistress had been fucked hard was filled with tiered bench-style seating... and a window. Fuck. Shit. Half the club had been watching the show Mistress had me put on for them, and I hadn't even noticed the two-way glass. All I wanted to do was leave. Not just the club but the country. I'd never felt so ashamed and humiliated. I felt like they could all see through my clothes to the cum-stained lingerie beneath.
Now I definitely needed that drink. Be careful what you wish for.
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