The Dare Pt. 02

You didn't know when it would come, though you obsessed about it every day since you found yourself on your knees in front of a gloryhole. Every time your phone went off, signalling a text, you grabbed for it, looking for those three little words again.

Four weeks later, you were about to break my rule and reach out before it was time. How and when I decided it was time was a mystery to you but one thing was evident, I enjoyed making you suffer. Days blended into nights, leaving you with only the memory of a warm, flesh and blood cock in your mouth and the promise of what was to come.

Lying in bed at night, you found yourself restless, often bringing up the email, as though to prove to yourself that you didn't imagine the whole thing up. The correspondence existed of a short exchange between you and the mystery man on the other side of the wall.

ME: Thank you for using my slut mouth and making me cum all over the wall. The next time we meet here, I want you to breed my ass and make me shoot my load all over the toilet like a nasty fuckslut.

HIM: Well, that's a hell of an invite after generously giving me the use of your very hungry mouth.

ME: What can I say...I'm a giver when properly motivated?

HIM: Ahah. Well, she was very insistent I agree to the gloryhole, so I understand that.

ME: So, I take it you've already agreed to another meet up?

HIM: I'll be there.

Your heart stutters at the thought. Fuck. Could you go through with it? Sucking a cock was one thing, letting a man...a stranger...fuck your ass, was another. There were moments over the last few weeks where you wanted it and, in those moments, knew you could go through with it. What if, when the time came, you couldn't do it?

God help you. The waiting was going to kill you.

******

The sound of a text message pulls you from your sleep and you almost ignore it, determine to sleep in on your Saturday off.

You last less than a minute before a hand shoots out to grab your phone off the night table. You were too deep in it at this point to pretend ignoring it was even an option.

Wiping the sleep from your eyes, you squint, heart stopping at the words finally appearing on the screen.

HER: I dare you.

"Shit!" Heart jack-hammering in your chest, you sit up in bed and switch to email, scanning for my message.

Our D/S relationship was a strange one, consisting of the exchange of deep, dark secrets and a series of dares that I challenged you with. It had started out small. Sucking a dildo, wearing a butt plug to work, messaging men online; all to push your boundaries. My rules were simple. Complete my dare and there'd be another one to follow. Reach out before I was ready or fail to complete a dare and game over. Things got serious on the last dare and this one was no different.

"Rise and shine, Nate! It's go-time. 1pm. Same place as before. Same code word as before. It's time to see if all that anal training has paid off, slut! I've either driven you mad with waiting or let things cool enough for you to chicken out. Text me when you're in the bathroom...no hand holding this time."

You cringe at "hand holding", recalling when you were moments away from high-tailing it from the meeting spot before I called and helped convince you to enter the building. You feel almost paralyzed at the thought of getting up to that washroom under your own volition. A month with no communication from me and only your own thoughts and doubts to keep you company was actually really brutal.

But then that was the point of all this, wasn't it? Pushing yourself out of your comfort zone to explore the things you wanted sexually...being submissive to a Domme. Failure was not an option at this point. Failure meant the end of this wild rabbit hole you'd been in and at the end of it was me...at least, you hoped.

You throw your phone to the bed and head off to the bathroom to get ready for what will undoubtedly be another life-changing experience.

******

You pull up to the building, the same one you've driven by a dozen times in the last four weeks, wanting to relive the thrill of the last dare, and park between a motorcycle and a non-descript white van, wondering if one of them belonged to your mystery man.

"Fuck...please don't be a man in his mid-life crisis or a child stalker," you whisper out loud, trying to calm your nerves.

Once inside the building you make your way up to Jeff's place and knock loudly, wishing like hell you could hear my comforting voice in your ear like last time.

Still as good looking as you remember; Jeff answers the door with a lazy smile. "Code word?"

You clear your throat before saying, "BBGL."

"Follow me," he turns to lead the way.

Every footstep draws you closer to that room, four walls that held your biggest, most secret craving until I unleashed it.

You could do this.

You HAD to do this.

Jeff pauses at the entrance to the bathroom, leaning against the door frame. "My money was on you chickening out."

That pulls you from your internal pep talk and you bark out a shocked laugh. "You in the loop too?"

A shit-eating grin pulls at the corners of his mouth. "Your lady friend is something else." He straightens up, pushing the door open and nodding toward it. "She never doubted you though so make her proud."

You walk into the bathroom with a renewed sense of confidence, closing the door and pulling your phone out of your back pocket before dropping down to sit on the closed toilet seat. You eye the darken gloryhole and feel your cock stiffen immediately in a Pavlovian response.

After a deep, steadying breath, you fire me out a short message and wait.

******

I keep you waiting for two long minutes before my face appears on the screen, signalling a video chat.

"There's my slut," I say excitedly when you accept the call.

I see relief on your face and you immediately smile back. "I'm here."

"All by your little self too...I'm so FUCKING proud of you!" I bite my lip trying to contain the rush of adrenaline that's making me feel like my skin might burst.

"Four weeks was too long...I almost broke and contacted you." Your eyes communicate more than the words you whisper.

I nod, knowing the feeling all too well. The days were long and the night's longer, taking every bit of self-control I had to stay dark. "And yet you didn't. You're stronger than you think."

"I'm not sure if it's strength or infatuation," you admit with a resigned smile.

"It's strength. Infatuation wouldn't have gotten you into this bathroom again. That's why I waited so long...I needed to know this went deeper than trying to impress me," I say, certain.

You take that in before saying, "Please don't wait that long again."

"I won't," I say, solemnly.

Relief transforms your face and I wink back at you.

"So, how much time do I have... before he arrives?"

Looking at the time on my screen, I say, "About 15 minutes...I'm not rushing you through this."

You blow out a sigh. "Part of me is relieved and part of me wants to rush through this."

I smile knowingly. "What part of you wants to rush through it?"

"The part that needs you here with me to actually go through with it."

I stick my tongue out at you. "I AM here."

You roll your eyes on a laugh. "You know what I mean...HERE here."

"I don't want things to be that easy for you."

You nod and a slight frown forms on your face. "Nothing about YOU is easy," you confess. "You have this ability to make me want to be worthy despite that though."

I let my eyes dance over your face not saying anything at first. "I promise you...it will be worth it, Nate."

A hundred things are reflected in your eyes and I know you want more...NEED more from me but I don't let you put them to words. "Tell me...did you jerk off thinking about what would go down in this room next time you were here?"

"It was impossible to think of anything else," you answer truthfully.

"Good," I whisper, letting you hear how much that pleases me. "Now take your clothes off for me."

Getting up from the toilet, you set the phone up so I can watch and begin undressing.

My eyes wander over to a monitor in the corner of room I'm in while you are distracted and I catch a glimpse of the man I plan to have fuck you through a hole in the wall, work his cock over in preparation. Heart racing, I try and school my features and focus on the phone in front of me so I don't give my location away, two rooms over.

"God, you're fucking stunning, Nate."

Your body is lean and chiselled, with a plump cock and full ass that have me practically drooling on my phone. It feels surreal that I will be able to reach out and touch you after all this time. You stand before me, letting me look my fill.

"Turn around," I grit out, "show me you're prepped."

You do, spreading your cheeks apart to show me the plug nestled deep. "It's the largest one of the set I bought...I can take it easily now."

I enjoy the view for a second before saying, "Remove it for me."

I watch rapturously as you do, groaning a silent fuck me​ at the sight of the gaping hole left in its absence.

"Is it full of lube, Nate?" I practically purr, "or do you prefer to be fucked dry?"

That has you cursing and I watch as your ass tries to clench around an imaginary cock. "Dry..."

"Keep that hole open," I order and squeeze my thighs as the throb in my cunt flares into a full-blown ache. "Why dry?" I push, already knowing the answer.

"Because...I need it like that. Like a hate fuck. Like I'm dirty for craving it and need to be punished..."

Hearing the words out of your mouth again, I'm surprised how much they turn me on. My initial reaction to it as your Domme was curiosity not arousal. This was your rabbit hole I was leading you down but I was definitely ALL IN on the journey. Sucking cock clicked for you, no contrived context to get you onto your knees...apart from a dare from me...but cock in your ass was a whole other story.

"Good thing I told my friend to leave the lube at home then..."

And right on time, a cock appears through the hole in the wall.

******

You see it out of the corner of your eye. The object of your recent fantasies appearing from the hole as if summoned by pure NEED. Your initial instinct is to drop to your knees and take it in your mouth like before but you remain still, hands holding your ass apart, awaiting instruction.

"He's half hard...looks like you have some work to do, slut."

That's all the instruction you need, falling to your knees and swallowing him whole. The same taste that's been haunting your dreams for weeks hits your tongue and has you moaning, going deeper. Pubes tickle your lips and the smell of him triggers a response in you that's all-consuming. Inhaling more of it through your nose, you choke on him, insatiable, and hear a muttered shout through the wall. He's rock hard, stretching your jaw to capacity and you wish the wall wasn't between you so he could grab hold of your head and fuck you properly.

"That's enough Nate."

Still, you don't stop, sucking like your life depends on it.

"Nate," my voice is firmer, penetrating the fog in your head. "Nate, stop!"

Only then do you pull off, shocked by your own display of hunger. Breath coming fast, you look down at your own hard cock in a daze and know one truth in that moment. "I want more, " you choke out.

"No...that's not what today is about, Nate."

You look over your shoulder at me and try and reel yourself in. "Tell me what to do...please."

My voice is steady, giving you simple orders. "Stand up. Ass against the hole. Hands braced on the toilet."

You do, watching as his cock disappears from the hole, allowing you press your ass against it, exposed and vulnerable. Bending over, your hands reach out on either side of the phone ensuring I have a killer view of your face and cock like I'm right there, crouched beneath you.

"Don't take your eyes off me Nate. I want to see is all...the discomfort and intensity...the self loathing...the inevitable pleasure."

You take a deep breath and a second later a sharp intake of breath as you're jolted forward under the force of the penetration. Teeth clenched at the burning intrusion you feel yourself immediately soften at the discomfort. He gives you no time to adjust before the sound of hips hitting the wall fills the room as he slams home again and again. Two sets of grunts, one pleasured and one pained as you endure being used like you've always craved deep down. You watch me watching you through it all, not able to make out if I'm enjoying it.

"Stroke yourself, Nate," my voice rings out.

You shake your head, still gritting your teeth, determined to suffer through it.

"You can pretend you hate this but I know that filthy ass of yours loves being violated and used. I know my cunt loves watching it..."

"Jesus FUCK!!" My words hit their mark and you feel your cock thicken, suddenly able to breathe through the intensity.

"Ughhhh!" You shout out as he changes the angle he's drilling into you, bumping your prostate.

Breaking down, you take your cock in hand and silently begin stroking yourself as the ache in your ass subsides and gives way to a weird kind of fullness that makes you feel owned.

You watch me, wishing like fuck I was sitting on the toilet with my mouth inches away.

"I know you're gritting your teeth to keep in the moans, whore, so let me fucking HEAR them! Let me hear how your body has betrayed your mind, turning you into a cock-loving fuckslut!"

Sweet fucking hell!​ Faint moans escape past your lips.

"LOUDER!" I order, not letting you off the hook.

That's when the dam breaks and you let loose, panting and grunting and moaning like a porn star, fist pounding down over your cock like a demon possessed.

"That's it, Nate," I encourage, "the moment you feel him explode and breed your ass, I want that load of yours shot all over the toilet like a filthy whore!"

His pace is frantic now with a string of filth spewing from his mouth and you know he's close to the edge. You find yourself eagerly fucking back on him as your own pleasure threatens to spill over. Your forehead creases and your eyes narrow into slits with the effort of trying to hold it at bay. Thats when you hear a shout and feel a series of pulses in your abused channel, and god help you, in that moment you wish he was fucking you bare.

Just the thought of being filled and bred with hot cum from an anonymous cock in a gloryhole has your balls drawing up tight and the pressure in your cock threatening to erupt. Standing up a bit you aim your cock at my face on the phone screen and bounce back on his still-hard cock and cum apart, roaring at the intensity and raining cum down on me.

A wave of light-headedness hits you and before you realize what's happening, your legs collapse, sending you to a pile on the floor.

******

Watching you reach your peak and embrace the pleasure in such a filthy act is exhilarating for me. Face flushed, cunt a wet throbbing mess, I'm seconds away from joining you when I see you fall to the ground, knocking the phone over in the process.

I'm on my feet before I realize what I'm doing and run down the hallway. Bursting into the bathroom, I find you sprawled out with a look of complete and utter shock on your face.

"Nate! Omg...are you okay?!" Rushing over to you, I crouch down and assess your face for what happened.

"Either I hit my head on the way down...or you're ACTUALLY HERE!?" The look on your face is adorable and has me smiling big enough to break my face.

"Surprise...!" I say, reaching out to touch you.

Your eyes close as my hands take your face in them, feeling a rush of adrenalin at actually being able to touch you. "Did we break you?" I ask, laughing through my concern.

Warm green eyes fix on mine and then dance down to my mouth as you shake your head. "No I...it was just..."

"Just what you needed?" I supply, recalling our conversation after the first gloryhole visit.

Leaning a bit closer you say, "Yes...that's exactly it."

Electricity flares to life between us and the distance closes as I pull your naked body to mine and find your mouth with months of passion and yearning between us. The kiss is intense and leaves us both shaking when we finally pull apart to catch our breaths.

Foreheads resting together you break the silence first. "You were right..."

"I was?" I whisper, wanting your mouth against me again.

Your hands find their way up to cup my face. "You were totally worth the wait."

My chest tightens and I tighten my hold on you. "Ditto, Nate."