The Double Anal Weekend Ch. 02

A half hour later I'm back in your apartment. I busy myself triple checking the details for tonight by sending a few texts to Eddie and making sure the correct presents are packed in my bag. While I'm reorganizing the toys displayed on your dresser and add the tunnel plug to your already impressive collection, my phone buzzes. I hop onto the bed and sit cross legged, opening your text to inspect how good you've been. It's a picture, this time in the private bathroom. You're bent over with your new panties pulled down just below cheek level, spreading your ass towards the camera with your hands. The black plug sits snugly in its rightful place, and your pussy peeks out from between your legs. On the picture you've written "Completely useless!" off to the side, and drawn an arrow to your vagina.

"Well, not *completely* useless," I think, but I appreciate the sentiment enough not to correct you. I reply with "Perfect. Keep your plug in if you find it comfortable and I will see you at five." A moment later, I receive one last reply.

"I will stay plugged until you leave, Daddy. I'd never forgive myself if I had to fail that challenge and take a break. You were so gracious to take a whole weekend out of your normal life to come train and use me so thoroughly. It's the least I can do."

A contented smile fills my face as I re-read it. You have no idea how hard I'm going to use that ass by the time the weekend is over.

Right at 5, I pull up to find you already waiting. You're still in the white blouse which means you made it through the whole day without changing. I lean over from the driver's seat to swing the passenger's door open and you bend low so you can see me. "Where'd you get this thing from?" you ask.

"It's a Zipcar! I had to wait an hour and a half for the last person to drop it off. Some people are so inconsiderate." You slide into the passenger's seat and I pull out. As soon as I get into the street, I see you hike your skirt up and pull your panties aside out of the corner of my eye.

"Daddy, I need you to touch this useless thing." Although you've gone long periods wearing various toys from your collection in the past, this weekend is the first time you've tried to wear one constantly and I can tell how horny it's making you. With my left hand on the wheel, my right gently traces the path from your knee up your thigh to your crotch. I feel the wetness before I even get to your pussy. As I touch what others might call your holiest of holies, my fingers are instantaneously soaked. I wriggle three fingers in as far as I can and hold them there as we slow for a stoplight. Your eyes close as you clench and grind on me, obviously craving a release. "I've been like this all afternoon, Daddy. I even left a little wet spot on my chair! What should I do?"

"The first thing you should do is clean my fingers off," I say. You willingly grab my wrist and pull my fingers to your mouth, deep throating them in front of the pedestrians crossing in front of us. "Other than that, for now you are to stay soaked and not touch yourself. That river in your pants is not my problem," I say while keeping my attention more on the road than on you. You frown and pout a little, craving an immediate release even though deep down you know Daddy knows better.

We talk about how the rest of your afternoon went. You mention that you're sure you caught one of the interns staring at your tits during a meeting in which you'd forgotten to keep your blazer buttoned. As we talk I can tell you're fishing for details, trying to figure out what I have planned. Instead of tipping my hand, I divert your attention to the next challenge. "Why don't you reach back and get your next present from the back seat?" Grabbing what you can instantly tell is another toy, you rip off the wrapping paper. As the box opens, you see a black oblong shape with a narrow flexible hose attached to a small bulb-shaped plug. "This is your first inflatable."

"Oohhhh!" you reply as your face lights up. "Now I get why you have the car. For some privacy!" Before I can say anything your panties are off and your ass is tilted to the side to let the plug you've worn so well all day finally escape. It slides out and you bring it to your lips, flicking your tongue to taste your ass essence. The plug ends up in the present's box and you toss it into the back seat. Fishing around in your purse, you produce a bottle of travel lube and apply more than enough to the inflatable. As your hand slathers the toy, you ask "what shall I do with this one?"

There isn't time for me to reply as it disappears forthwith between your legs and underneath you. A satisfied moan signals that it has popped in with ease. "It feels so small right now! I think I can fix that. Let's see, now I just do this?" Your hand clenches tight around the bulb. "Oh! Hi there!" you squeal. You give it three more pumps, exclaiming "Aahhh, Ahhh, Ahhh!" with each one.

"That's four," I say, keeping count. "You may stop when you get to ten. No fewer." The next two are no real challenge, though I notice the seventh one becomes slower and more deliberate. As we enter onto the freeway, moans and sighs become your only communication. After the seventh, you can't help but pause to shift on a new kind of fullness, one that expands to fill every crevice and contour of your magical opening.

As you start to squeeze the eighth time you exclaim "Ooohhh shit! Daddy, I'm already stretched so tight!" You shift in your seat, attempting to find just the right position but the feeling is relentless. It takes a couple minutes but you are a determined girl and eventually you're able to complete one more pump of the bulb. The way you writhe in your seat gives away the distress you find yourself in. "Two more??" you gasp with equal parts panic and disbelief in your voice.

"Yes. Two more. I'll drive around in circles if I have to. I need two more before I can drop you off." Your eyes close as you revert to your training, remembering how you worked so hard to please me last week when I demanded a video in which two medium-sized vibrators had to be completely inserted simultaneously. It had taken a half hour and a half-dozen positions, but you succeeded in stretching your delicate bottom further than you ever had before.

You suspire laboriously, pulling the plug out a bit to stretch your inner sphincter, and then pushing in as far as you can while rhythmically clenching and releasing until almost all hint of pain and discomfort is gone. I hear the whooshing sound of another pump as you purr "Mmmm, there's nine." It's obvious you're trying to act like it's not a struggle but every bit of body language proves to me how arduous your effort is.

As I turn off of the main road onto your apartment's side street I remind you where we are. "Three blocks. Can you do it?"

You take it as a challenge and bite both lips together as you hold in another deep breath. I watch as you push down hard, trying to squish the bulb in your hand one last time, but you balk and wince. "Goddamn it, so full. So full!" you say as your body lurches forward, slamming a hand onto the dashboard to steady yourself, your whole abdomen contracting. With one block left you close your eyes again and enjoy a few seconds of zen, then try one last time. The bulb empties, bringing you to maximum size. Guttural moans combined with fingertips furiously manipulating your clit tell me all I need to know about how you feel. "TEN!" you exclaim.

"Mmmmm. Good girls stretch their asses further than they ever thought they could," I remind you as we pull up to the apartment. You flash a weak smile that does nothing to hide how close you've come to tapping out but still shows how proud you are to have completed your task. I see your hand move from clit to the metal valve and gradually twist it to decrease the pressure in your anal cavity. My hand bolts into your lap and I place my thumb over the escaping air.

"Close it," I command. Your fingers twist it shut. I grab the bulb and re-inflate once. "You are not allowed to ever open that valve without permission."

Biting your lower lip even harder you stare straight ahead, realizing the challenge isn't over. "When can I deflate, Daddy?" is all you say in a whimpering voice. In your mind, you're begging to be able to release the pressure as soon as you get inside. The hand on the dash starts shaking as I hear pitiful little cries begin to accompany each breath. Your eyes well up from the intensity and it takes everything I have inside me not to take pity on you. I didn't fly all the way here and plan out 72 hours of anal-focused slavery just to be the one who buckles and ends up throwing in the towel.

"You will open the valve as soon as you're inside your apartment," I state matter-of-factly. Your only resistance comes in the form of a loud, misery-filled moan. I get out and walk around to open your door but you've already swung it wide. You shift your legs out and have to grab my arm in order to stand, arms still shaking as you rise from the seat. The first step onto the sidewalk is a challenge. Your left arm links with my right and I feel your weight on me as you walk up the steps to the front door. A tear rolls down each cheek, proving in yet another way the depths of the agony and anguish you'll willingly endure to prove your worth to me. As you fumble with your keys, your legs begin to shake as well. You're barely in control as you try in vain to open the lock but the key clatters off the escutcheon over and over, unable to find the keyhole.

"Fuuuuuuckkkk, Daddy! I don't know if I can do this! I'm sorry! I'm sorry!" The timber of your voice is unmistakable. The only time I've ever heard you say something that way is when you're on the edge of saying the safe word, a word you've never had to use. I grab your keys and help you through the vestibule into the lobby, then walk you directly to a couch where you collapse on your side in a heaving, moaning pile.

I twist the valve open and let the plug deflate about halfway, then shut it again. "Ohgodthankyoudaddy! Ohgodthankyou!", you repeat over and over. I bend down and kneel on one knee, observing the relief on your face but saying nothing. It's only now I notice beads of sweat on your forehead. I give you a minute to collect yourself after which you start to stand.

"Stay here. This is only a temporary reprieve," I say coldly, pushing you back on the couch. "You will wait here for me while I park the car and then you will re-inflate." I turn and leave without waiting for a reply, pausing only to look back and see the hose and bulb peeking out from under your skirt as if you don't notice or don't care that you could be exposed as the slut you are to anyone who walks by.

I park the car three blocks away in the designated stall, returning it for the next user. When I get back to the apartment's lobby a few minutes later I'm pleasantly surprised you're not alone. Your neighbor from down the hall, Marcus, is standing next to the couch chatting with you. I can tell you've at least partially recovered, having fixed your mascara and tucked the hose and bulb up under yourself too. As I open the door, I hear you laugh in response to something he just said.

"Marcus, you remember my boyfriend from last night," you say, reintroducing the two of us. We exchange pleasantries and you continue "Marcus was just complimenting me on my outfit from last night. I told him it was all your idea." A mischievous look crosses your face as you look him up and down, admiring his darker complexion and chiseled body. "I mean, you should have seen what was underneath my jacket, Marcus." His smile grows wider as his eyebrows arch with interest and approval.

You've obviously regained your composure in the time I've been gone so I double down on your flirting. "If you ask me, there was a very, very naughty girl underneath that jacket. You'd be shocked if you really knew."

He looks right at me, understanding the permission I just gave him and then turns to you. "Well, maybe you should tell me." He sits down next to you on the couch as you move over just far enough to give him room.

You sit back against the armrest opposite him, tingling with excitement and a tinge of fear at the possibility of getting caught. You slowly pull your skirt up until the bulb you've kept hidden from sight flops back out between your knees. He can't tell what it's attached to and gives you a puzzled look that rapidly changes to excitement as you pull his hand forward and place the bulb in it. "Squeeze it twice, please" you say. The 'pffft, pfft' sound of the pressure increasing is audible in the room, along with the briefest moaning sighs as you welcome the stretch.

"So, um, whats this thing connected to?" he asks. Eyes still locked on his, you pull his hand under your skirt and swing your legs open. His fingers wander, inspecting your soaking pussy and as he does, he realizes it's empty. The look on his face is priceless.

"Guess again." His fingers tentatively move south, until he feels the lip of the plug and the hose it's connected to. I've stepped back to the opposite wall, watching the excitement on both of your faces build. You feel like such an unapologetic whore and my silent approval only spurs you on further. You lean forward a little as if you're about to kiss him as you say "If I had to guess, I'd say you like what you see."

Just as you're about to ask him for one more, we hear voices in the hall. His hand jerks back and your legs close, catching the bulb between your knees. A middle age couple comes around the corner and completely ignores us as they leave the building. As the door closes, we both break out laughing at Marcus's expression, his eyes wide as saucers and his hands tucked behind his back as if that would somehow prove his innocence. It takes a few seconds but eventually he relaxes and sighs deeply, shaking his head.

"Watch the hall," you say to me. I stand and watch with one eye on the stairs and one eye on the two of you as you turn around and get on your knees, elbows on the arm rest of the couch, ass pointed towards him. I watch with approval and delight as you pull your skirt all the way up to reveal your panties.

"Oh damn! Anal only? Really?" he says. You look back over your shoulder at him as you slip a finger into your mouth and bite it.

"I am this weekend. Maybe longer. Now give me two more, please." I watch over his shoulder as he reaches forward and slowly squeezes once, then twice. You let out a yelp and your whole body shudders with the second one as you near the stretch you suffered through while walking to the door a few minutes ago. A moment later your skirt falls down and you get up gingerly, walking around him and over to me with the bulb swinging between your legs. Leaning down behind him you whisper in his ear to him in a slow, sultry voice. "Thank you."

He stands up. "Any time, and I mean that. *Any* time," he says.

Before you can reply I say "Ok. If you hear any concerning sounds coming from her apartment, don't be afraid to knock and make sure she doesn't need any . . . help. Especially tomorrow night. Understand?"

He flashes you another big smile."I'll do that. I love to be helpful." As he leaves, I turn back to see you biting your finger again.

"Christ, I've been wanting to fuck him since the day he moved in," you say.

"Something tells me you're going to get your chance!" I catch myself daydreaming for a moment about all the newfound possibilities. I nod in approval as you start walking towards the stairs, bulb dangling between your legs. I catch up to you as fast as I can and grab your shoulders to stop you as your foot hits the first stair.

"You owe me one more. I know you're not completely full." You sigh and reluctantly grab the hand rail as I grasp the bulb and squeeze until it's totally empty. I'm shocked at how hard I have to work to empty it. Your knees begin to shake again as you start back up the stairs, hauling yourself up each one by the railing. You barely notice me pull my phone out and video your effort. It takes you a minute or so to finally reach the third floor landing where you pause and shift from leg to leg while pushing your ass back towards me, trying to make more room in an asshole that has no room to give. As you start down the hall, you have to keep one hand on the wall as you walk. I continue recording, in awe of your effort and determination. I grab your keys from my pocket and quickly fling the door open and you fall into the apartment on to all fours in the entryway.

As soon as the door clicks behind us you scream "PLEEEAAASSSEE. DAAAADDDYYYY!" I kneel down and twist the valve in my hand, opening it wide. It hisses as you feel the unbearable pressure finally relent. The volume of the hissing air increases and falls as you contract on the plug, forcing it to return to its original size. You're so stretched out that it hasn't finished deflating when it pops out, still hissing as it's held against your asshole by your panties. I pull it out and hold it in front of your face. It's an effort for you even to raise your head to stare at it. "Only beautiful, determined, incredible anal sluts could do what you just did. You make Daddy so happy when you show how much you can take and how hard you're willing to push your limits."

You stay on all fours for a minute as you revel in the empty feeling. Eventually you start to crawl towards the bathroom and I follow you. Once there, you can't help but haul yourself up onto the commode. Just as you're about to give into the unbearable urge to push, I grab your chin and pull your head up to look at me. "Stop. You need your cleaning for tonight, don't you?" You nod and whimper wanting nothing more than to void, but you comply. My pants are off in a flurry, revealing the rock-hard cock your performance left me with. I sit on the toilet first, holding my engorged phallus straight up. "A truly good girl would sit all the way down and let Daddy help you with that."

"Yes sir," you reply reluctantly in a thin, feeble voice, turning and inching backwards, gape aimed at the tip of my cock. You're still shaking a little from the effort, and the shaking amplifies as I grab your hips and lower you until I'm balls deep in your well-stretched rectum. Moans that betray your discomfort echo across the bathroom tile but no matter how hard I'm pushing you, you know you'd never say no right now; this is one of the things you've fantasized about forever and never done. Now it makes sense to you why I was carrying around such a big bottle of water when I picked you up.

The warm gushing feeling of my piss starts as a trickle, then turns to a flood as it expands your insides and works its way deeper than my cock or your toys ever could. "Oh goddamn it!" you curse as the warmth works its way from where the immense pressure started up the left side of your abdomen. It feels like I'll never stop but eventually, every last drop is inside you.

"Clench as tight as you can," I command as I clamp my hands on your hips and begin thrusting. You can barely feel the length of my cock pulsating. Instead, you feel the golden fluid being sloshed around deep inside as I get off on the unique sensation of having only your anus gripping me as I fuck you. After a minute, I slow my rhythm and then stop. "Now grip hard as I pull out."

As the head of my cock falls out I stand up and push you down on the seat. "You may express now." Before I even say the last word, simultaneous whooshing sounds and the labored moans of your relief fill the room as I lean in and turn the shower on. I strip what's left of my clothes off and step in, telling you to join me. After you enter I hand you a small vial of greasy lube and you take some to prepare yourself for what's next. Without having to be told, you turn around and put your hands on the wall opposite the shower head as I unholster the enema attachment I installed for you last month and gradually insert it.