Sinful Playtime
A Fictional Story by Outsider1505.
Her voice cuts through the silence of the bedroom as she slips inside, your eyes focused on the floor. You know not to look until she says so, much as a part of you is ever so desperate to gaze upon her beauty once again.
But you wait just as you have ever since she told you to come over.
That was three hours ago. And you’ve been kneeling on her bedroom floor stark naked the whole time.
Her footsteps move from the doorway into the room, heavy and clunky. She’s wearing boots- something she knows drives you wild. Your eyes want nothing more than to move towards the sound, to catch a glimpse of whatever pair she’s wearing today. But you refrain; the agony of waiting is nothing compared to what she’ll unleash if you disobey.
The sound gets close, then passes you, and you catch a small glimpse of black and red out of the corner of your eye, but nothing more. Only when she stops in front of you, and you have no choice but to notice the toes of her favorite pair of knee-high black and red leather boots, do you dare drink in the sight of them.
“Look up, sweetie… Mistress has a surprise for you.”
You do as she commands, your eyes slowly moving from the floor to her boots, up her strong, black fishnet-covered legs, only to stop before you have a chance to look up at the rest of her. Your eyes focus on what she’s wearing around her crotch—something you haven’t seen in quite some time.
A strap-on.
But not just any,
Her biggest and thickest one.
The massive purple phallus is at least twelve inches long, three inches thick at minimum—more than enough to really and truly wreck your ass- as she has in the past. Yet usually, such a thing is a punishment- and as far as you know, you’ve been good. Or as good as one can be.
“You remember this, don’t you, Trinket?” She asks with a giggle, and you look up at her beautiful face, her makeup suitably demonic and her red lips pursed together in a grin. “I thought it was time to dust it off again. We wouldn’t want you to get lazy now, would we?”
“No, Mistress Syn,” you whisper, and realize it’s not punishment. At least not active. Just your beloved Mistress’s idea of fun. For her. Not for you.
The knowledge must be painted all over your face, seeing as she pouts. “Aww, are you afraid, Trinket? Don’t be…. I made sure that you’ll enjoy this just as much as I will.”
Without another word, she picks something off the bed, and your eyes widen when you realize what she’s holding. Something you love as much as her boots, if not more.
Rubber gloves.
You could count on one hand the number of times she’s deemed you worthy enough to experience your most favorite fetish, and it appears today is one such time.
And as expected, it’s not without its costs.
Mistress Syn opens the package and slips the first glove on, snapping the cuff and smiling as you involuntarily jump at the noise. “My dirty little Trinket loves when Mistress wears these gloves, doesn’t he?”
You nod. “Yes, Mistress Syn.”
The second glove follows, and your cock joins you in jumping at the sound of the snap. You were already hard the moment she walked in, but with the addition of the gloves? She could make you cum in an instant if she so chose.
But that isn’t how Mistress Syn plays, and you know it.
A rubber-gloved finger beckons you closer, and you crawl towards her, as well as the massive purple cock hanging off her. It moves back and forth in front of your eyes like a pendulum, stopping only when a yellow-gloved hand wraps around it and steadies it in front of your mouth.
No words need to be said, no commands need to be made. But she does so anyway, just to remind you who is in charge.
“Open wide, Trinket.”
You do as she says, opening your mouth as wide as you can, unsure as you always are if you can manage to take the rubber phallus in.
Mistress Syn guides the tip of it past your lips, slowly moving her strap-on into your mouth a little bit at a time. She stops about a third of the way, then lets go and grabs hold of your head with her gloved hands. The feeling of the rubber as well as her strong grip is enough to send shivers down your spine, and that’s before she begins to move your head forward, forcing her cock deeper into your mouth.
“Suck it, Trinket,” she whispers, her words enough to drive you wild even without the gloves or strap, “make Mistress’s cock as nice and wet and pretty… Because that’s the only lube you’re getting today.”
You groan, and begin to suck her strap-on in earnest, the thick, vein-covered purple dick moving in and out a little bit at a time. You know she could shove the whole thing in if she wanted to- and has, but today she seems intent on going slowly. Making sure you both can ‘enjoy’ the experience.
Your tongue slides along as much of the strap as possible, given how much of your mouth it fills, but you do your best to get it wet, the saliva coating it getting thicker and thicker as she continues to move your head back and forth. Her gloved grip never wavers, and she keeps a good, steady rhythm as she slowly and methodically fucks your mouth for all that it’s worth.
As she does, your own cock- barely even a quarter of the size of hers- gets harder and harder. There was a time you’d have never thought such a thing was possible- for you to get hard by being forced to suck cock, but just as with a great many other things, Mistress Syn has proven you wrong.
She knows you love it. And even if you didn’t once upon a time, you sure as hell do now.
Back and forth, she keeps moving, and after a few minutes, she lets go, denying you the touch of those rubber gloves you adore so much when they are on her strong hands, but that doesn’t stop anything. Even without her guiding you, you continue to follow her rhythm, moving your head over her cock again and again, taking more of it inside your mouth and coating it with your lustful saliva.
“Mmm, such a good little Trinket…. Sucking Mistress’s cock like the desperate little slut you are…”
You groan, her cock nearly touching the back of your throat as she thrusts, but you know she’s right. You are a slut. You are her slut. And you love that. You don’t want to be anything or anywhere else in this moment. And she knows it.
Her gloved fingers slide through your hair as she pushes you as close to her as possible, her purple cock practically going down your throat before she pulls it out, and you gasp both at its loss as well as the sensation of it slipping free from so deep inside your mouth.
For a moment, it hangs in front of you, shining in the light of the bedroom and slippery with your spit. It’s not much, but it’s better than nothing.
Mistress Syn steps back and points at the bed, and without a word you rise on weak, nearly numb legs, and plop back first onto the bed.
You tremble as her gloved hands carefully help move your feet into position, resting on the custom stirrups she’s placed there. The restraints are tied, and before you know it, you’ve assumed the position she likes you best in.
Prone, restrained, and completely at her mercy.
“Time for round two, Trinket,” she says with a smile, and you feel the tip of her strap on, wet with your saliva, slowly make its way past your ass cheeks and into your waiting ass. And though it’s a sensation you’ve felt countless times before, with this particular cock, it never seems to get any easier.
The massive purple cock begins to slip inside you, filling your ass just as easily as it did your mouth, and once it’s good and in there, Mistress Syn begins to move back and forth, finding the same rhythm as before and slowly starting to fuck your slutty ass for all that it’s worth.
A moan slips out- once more, something you never expected to enjoy but have grown to love thanks to Mistress Syn, and as her cock slides in and out of yours, yours begins to throb along with it actively. You can feel the precum dripping out the tip, but know that even if you wanted to, touching it is forbidden.
When you’re here, the only person allowed to touch your cock is her.
And she’s going to make you wait.
Mistress Syn’s cock slips deeper into your anus, so deep you’d swear she’s planning on prodding your prostate, but she slides it back out before going that far, only to try again and again. It’s a different kind of tease, one that reminds you just how much power she has here. She could practically impale you on her massive cock if she so desired, but that wouldn’t be nearly as fun.
“You like this, don’t you, Trinket? You love when I stick my big, thick cock inside you and just fuck your slutty ass like this?”
You moan- it’s answer enough for her. And she keeps at it, even as you wish she’d acknowledge your aching cock just once.
As you know, please be careful what you wish for.
Because you just might get it.
While her strap continues to have its way with your ass- barely even needing to struggle now as the rubber phallus just slides into your accepting anus- one of her gloved fingers begins to poke and prod at your throbbing erection. The sensation, brief as it is, feels so good, but you know what’s coming won’t feel as amazing.
“Aww, would you look at this… Your pathetic little dicklet is dripping for me and my big cock…I bet you want me to touch it… To play with your teeny wienie….”
A groan slips out that is more than enough to prove her right, but she wants more. She wants you to humiliate yourself for her.
“Say it, Trinket… I want to hear it from you. Now.”
You sigh. It’s the truth, and you both know it, but that never makes it any easier. Yet it’s what she wants, and you would never disobey your beloved Mistress.
“I want you to play with my teeny wienie Mistress Syn. Please touch my cock.”
She laughs, and though it shouldn’t, it makes you even harder. She has you so well-trained now, even her cruel laughter is enough to get you going. But she’s only getting started.
“What cock? You mean this tiny little nub?”
Her gloved hand wraps around it, your aching cock disappearing in the confines of the tight yellow rubber. It feels so good, her strong grip aided by the ridges along the palm of the glove, and you moan with pleasure even as her words hang in the air.
The other glove moves to her mouth, and her eyes widen in mock surprise. “Look at that Trinket, it’s all gone! Your tiny dicklet must be hiding… I wonder where it could be….”
A slow, deliberate stroke moves her gloved hand down your cock, sending shivers down your body. The tip can just barely be seen peeking out of her grip, but she acts as if she can’t see it. “Wow, your cock is really good at hide and seek, Trinket…”
She slips back up your shaft, then back down again, touching you just enough to drive you crazy but not enough to give you any pleasure, especially as she continues to tease you.
“Even with my cock so deep in your ass, I can still see it… It’s so big and thick there’s no hiding it… But yours is so small, it’s almost impossible for me to find it…”
You groan, a mixture of pleasure and despair, but you know she’s loving every second of this, and by extension, so are you. Especially once she decides to tighten her grip and stroke your cock in earnest, allowing more than just the tip top poke out with this pass.
Once again, her free hand moves to her mouth in mock surprise. “There it is! Silly little Trinket, your cock is so small I only need one hand to make it disappear…. I’d need at least four hands to do that to mine.”
Mistress Syn lets out a wicked laugh, her cock shaking inside your arse as she does. The vibrations mix with her slow, deliberate strokes, and though it feels good, the denial that comes hand in hand with such pleasure is almost more than you can take. She is in total control of you, and all you can do is go along for the ride.
Her free hand grabs hold of your leg to steady herself, and she begins to fuck your ass with greater frequency. Her strap-on moves in and out faster than before, and you can tell from the warm feeling on your bottom that she’s getting close. The wetness of Mistress Syn’s pussy is soaking through her harness, and even as her cock slams into you harder and harder, you can’t help but be pleased, knowing she’s getting off on your submission.
It’s the greatest feeling in the world, giving your Mistress pleasure. And Mistress Syn deserves all the pleasure you can provide.
Luckily, she gives as good as she gets, her gloved hand sliding up your shaft in time with her thrusts. Her grip is tight, the rubber engulfing your cock, and the faster she strokes, the closer you feel to cumming.
If she decides to let you.
You know from experience, Mistress Syn may simply stop once she finishes, but you’re so close, so desperate, you can only hope she’ll allow you the privilege of cumming for her today. She can clearly feel the throbbing of your cock, the warm precum dribbling out and down your shaft with every stroke.
The thrusts are even harder now, the harness practically slamming into your ass and leaving marks. The wetness is audible now, with every smack of the leather against you followed by a wet squish. Oh yes, she’s close, and as her hand grips you so hard it hurts, Mistress Syn begins to moan, then groan, then scream, and with a few more good thrusts into you, a burst of wetness flows free, dripping out from behind her harness and against your ass as her cock slides deeper inside you than ever before.
For a moment, you think it’s over. That she’ll simply pull out and leave you there aching, but her gloved hand doesn’t stop. If anything, it moves faster now without the distraction of her thrusts. You feel the slick rubber slide up and down again and again and again, your cock ready to explode in her fingers, yet she does not let up even the slightest.
Not until she moves her other hand off of your leg, and brings it right to the tip of your cock.
You know what’s coming, but in that moment, you don’t care. Because Mistress Syn’s hand moves from your full, aching balls, up your throbbing shaft, to your precum-drenched tip, and with the effortless skills of a true professional, she guides the orgasm you didn’t expect to get free from your cock.
Right into the palm of her other rubber-gloved hand.
Mistress Syn expertly milks you, squeezing out every drop, spurting it out from the tip into her waiting hand, draining you dry even as the pleasure continues to wash over you. It seems like forever that she granted you such a release, and as the euphoria takes hold, you lay there with the biggest smile on your face ever.
After a few seconds, the cum stops flowing, and Mistress Syn lets go of your spent shaft. You almost don’t notice her slide her strap-on out of you, nor her walk to the top of the bed where your head lies, face red with pleasure and eyes filled with tears of joy.
Without a word, she brings her gloved hands to your face, and with a smirk, mashes your cum all over your face, covering it with your juices and rubbing every last drop onto you until she’s certain it’s all gone.
You lay there, face drenched in sweat and semen, humiliated yet so overjoyed you barely even realize it. You even slide your tongue out to lick some stray droplets off of Mistress Syn’s gloves. All the while she watches you work with a grin, and carefully pulls the gloves off her hands before dropping them onto your face.
“Hope you liked that, Trinket,” she says with a smile, “because my cock and I aren’t through with you….”
With the gloves on your face, you can’t see her, but once the tip of her cock pokes into your ass again, you realize you don’t have to. You know exactly what she has in mind for you, and as her strap-on slides back inside, all you can do is groan into the sticky rubber resting on your face.
Here we go again.
The End.

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