The Double Anal Weekend Ch. 02

Stepping away a little, you peek back at the phone to make sure you're still in frame. As your ass tips down, your right hand comes through your legs and hovers a few inches under your massive, beautiful forced gape. The remains of my cum mixed with lube and ass juice begin trickling out, flowing over the lip of the plug and into your palm. A big, sloppy glob plops onto your fingers with enough force I convince myself I could hear its impact. Faint moans escape your throat as you clench and then push, expelling more cum with each repetition. The fingers on your left hand spread across the top of your ass, holding onto the rim of the toy lest it fly out and clatter across the tile floor alerting everyone to the depths of your depravity. Eventually the flow our mixed secretions slows until only the occasional viscous drop forms, hangs briefly, then falls into your cupped hand.

You spin around and lean down so your face is nearer the phone. Turning your head sideways, you hold your hand a little higher than your lips to let the fluid remains of our morning lovemaking cascade into your mouth. You let half of it cover your tongue, showing it off for the camera before swallowing deliberately and licking your lips with a wide, satisfied smile. Next you proceed to lap up every droplet of ass juice from your palm, flicking at the viscous globs of nectar with the tip of your tongue, wanting only to put on the best show you can for me. "Jesus, it almost tastes better now after a couple hours inside me than it does when I swallow it right after we're done!" you think to yourself. "What sort of a slut am I turning into?"

As if to answer your own question, you tilt your head up towards the ceiling in profile to the camera and hold your hand above your mouth, nonchalantly letting a pointed finger descend past your lips until the tip tickles your uvula. Pursed lips assure it's fully clean as you retract it only to point another finger towards what I've told you many times is your second-most important orifice and repeat the process. After your pinky has finished its trip to the back of your throat, you squeeze all four fingers together and hold them above your wide open mouth.

The dark red lipstick you chose this morning smears along the tops of your fingers as more and more of your hand fills your mouth, only stopping as the impossible width of your knuckles knocks against your front teeth. I can see your tongue pulsing outward and lapping the inside of your palm as you strain to push your digits even further down your throat, causing yourself to silently gag once, then twice, then three or four more times. Thick spit mixed with a healthy amount of the combined essence you just forced yourself to regurgitate now coats your fingers, requiring that you to lick them clean once again.

Next, you turn back around and steady yourself with one foot on the floor and the other up on the toilet paper dispenser, pushing your perfect bottom toward the camera to show me the glinting silver and soft, pale pink insides of your tunnel toy. As you pull, the skin of your anus once again stretches impossibly taut, holding the toy as if it'll never let it go. The widest part finally reveals itself only for you to hesitate long enough to bask in the mind fuck of being such a total slut only minutes before you have to go to a meeting.

As soon as it comes out you whip back around and lean in close, swirling your tongue around the inside of both ends, savoring every last drop. Letting your lips rest against the flange, you hold it all the way in your mouth with your tongue pushed through the center, posing innocently with your eyes pointed up and to the left. You then remove it and silently giggle at yourself, inspecting the inside and noticing that a faint remnant of our residue still clings to the inside. A finger assures that every morsel has been retrieved and enjoyed. After you take the last lick, you lean in close to the phone and whisper "Mmmm, yummy!" and the video ends. I watch it four more times before I look up from my phone, momentarily panicked that someone must have noticed my bulging erection through my pants and how intently I was watching your performance or that they've somehow been able to see the filth you sent me.

I back the video up one last time and pause at the point where you're holding the plug in your mouth and take a screenshot, saving it as the contact picture for you in my phone. I save the video to my secure app and immediately reply. "My god, that was hotter than I ever could've imagined! I can't walk anywhere for a few minutes right now - too hard!" A few minutes later you tell me you're back at your desk and you can't believe how naughty you feel. And how good I taste. I reply by telling you that this may be the most shocked I've ever been by something you've done. Your response comes only in emoji: gushing water, eggplant, hole, shocked face. Followed by three thumbs up and a tongue.

Chuckling at your reply, I remind you that I'll be by at 12:30 to take you to lunch. I also let you know that I expect you to be wearing the tunnel plug when I show up. "Yes, Daddy. Gtg. Meeting," is all I get back. I spend the rest of the morning stopping by a bodega, a clothing store, and a sex shop that really should have a better selection for being in the heart of a big city. I get back to the old movie theater 15 minutes before they open, right as an employee shows up.

The man unlocking the door is the kind of colorful character you only find in big cities. He's wearing a ragged velvet jacket with frills lining both the sleeves as well as lining where the zipper should be, thick black John Lennon glasses, a Snidley Whiplash mustache, leather pants with buckles all over them, combat boots with flowers painted along both sides of the heels, and an anachronistic, jaunty hat. "Do I know you? No, I don't know you. Sorry, we're not open yet, and you have to be a member anyway," he says. I introduce myself and explain that I've been emailing the manager over the last few weeks with a proposal.

"Oh! Shit yeah! That's me! I'm Eddie!" he says. "Come in, come in!" He leads me into the lobby so we can finalize some details.

Eddie is a talker. "A talker and a lover," as he mentioned at least four times during our conversation. Regardless of what he is, he's made me late. I finally get back out onto the street only five minutes before I'm supposed to be back to pick you up. Dumb luck favors me this time as a taxi crawls to a stop in traffic right in front of me. I jump in and he takes the next right, en route back to your work.

I see you from a block away, purse over your shoulder and a some paperwork held across your chest in a manilla folder. I wonder to myself if the folder is necessary, or if it's hiding what's written on your new bra. We pull up and I jump out, running around the back of the car to get your door for you. You step purposefully off the curb down to the street. Only I know why you're being so deliberate. As your ass swings into the car with your right hand bracing against the door to lower yourself to the seat, you look back over your shoulder and say accusingly "You, are late". I close the door for you and get in the other side.

"Hey, some of the best things in life take time," I say, flashing my 'aww shucks, me?' grin. The driver pulls out and heads to the restaurant I told him was our final destination earlier.

"It's ok. It's Friday, after all. I can take an hour if I want." It's a short drive to the place I've picked for lunch, but there's just enough time for me to sneak my hand up your skirt and let a finger wander past your panties, around the cusp of the plug, and up the metal walls confirming you've done as I ask. You bite your lower lip and don't make a sound as I swirl the tip of my finger a few times, exploring the warmth of your depths.

After I pull out, you glance at the driver quickly with a devilish grin making sure he isn't watching, then turn to me and open your mouth. Your eagerness morphs into shock as I take the finger and put it in my own mouth, licking it clean. Noticing your surprise, I stop with my finger between my teeth and shrug my shoulders as if I'm completely innocent. Nonchalantly shaking your head, you purse your lips. "What am I going to do with you?"

In a flash we're there and I pay the driver. I hurry around to the other side of the car to get your door and you stand, stepping up onto the curb with tiny halted steps. As the cab pulls away, you declare "This thing is CRAZY!" I hold the door for you, watching you move as if you're walking in heels for the first time.

"Well, come tell me all about it." I follow you in, immensely enjoying watching the way you're moving.

The restaurant I've chosen is a lunch-only place called "Wrap It Up" that has a sign in the shape of the box of the same name from that one episode of Chapelle's Show. They even have a functional "wrap it up" box that the employees hit every time an order is ready. We walk up to the counter and stand behind an older businessman who just finished his order. He shuffles down along the glass-enclosed food prep area and stands next to the box.

"Hi! What can we make you?" the twentyish man behind the counter asks us. I can't tell if he's a grungy looking college kid or a cleaner-than-average skater punk. He's wearing a flat brimmed hat he's obviously never washed overtop of black hair that was poorly dyed blond months ago, a black shirt with a black design on it which makes it impossible to see, and has a septum piercing. His arms are dotted with tattoos of various quality in seemingly random places.

I make a judgement call that he'll do and decide it's time to spring one of my more devious ideas on you; if a weekend like this is worth doing, it's worth going all in. I pull a piece of paper that already has my handwriting on it out of the back of my notebook and scribble a couple extra sentences at the bottom. You know that notebook. Before you even read a word your heart starts racing. What has he dreamt up for me here?

"She'll order for both of us," I say. You grab the piece of paper and start reading. The first half of the order is for me, and is pretty mundane. A chicken wrap with some of this and some of that but definitely none of those. As soon as you read the second part your eyes jump up from the paper to the guy behind the counter, then over to me. It's a look of disbelief that promptly gives way to a chuckle and an exasperated sigh. You glance behind us, desperately relieved there's no one else there. As you lean in closer, the puzzled employee looks at me as if asking permission but then does the same. Right as you take a deep breath to gather your courage, I clear my throat.

"Ahemmm hmmm mmhm!" Both of you turn and look at me simultaneously, your heads only a foot apart. Pursing my lips and arching my eyebrows as high as they'll go, I hold my hand out flicking all four fingers at the same time as if to shoo the employee back to his side of the counter. As he stands back, you sigh again and stand up straight. I smile and nod as you re-prepare yourself to ask the question. I've seen you do this before. Leaning on your college theater experience, you think to yourself "act like a girl who quit her job and is surviving only off her onlyfans content."

"So, what would you recommend I order . . . if I'm planning to do a LOT of anal later?"

You say it in a confident, sultry tone, hanging on every word. There's more than an uncomfortable amount of silence as his eyes dart around and he shifts from foot to foot that's finally broken by the employee. "Um, did I . . .uh . . . did I hear you right?"

You lean in closer which I allow this time, and continue. "I mean, if I'm going to be getting fucked in the ass most of the night, what would you recommend I go with?" He fumbles with his words and shifts from one side to the other, eyes darting between you and the menu. His mouth opens and closes a couple times as he tries to form an answer, then second guesses himself. And then, he floors both of us.

"Well, let's see. Probably nothing too heavy. Stay away from the beans for sure. No steak, I'd think." We both turn to each other and exchange impressed glances as he continues. "I'm gonna say probably one of the soups. Nothing cream based though. And maybe a smoothie on the side? Whadaya think?" he asks, a big smirk proving how proud of himself he is for his answer.

You can't help but burst out laughing. "Oh-my-god, that's just perfect! Any soup. You pick. And a banana and strawberry smoothie with coconut water." You giggle a little more as he shrugs his shoulders and rings us up, both of you smiling the whole time.

"Thanks for playing along. That was pretty good," I say as I pay and put a twenty in the tip jar.

"Thanks!" he replies. "It's not the craziest thing to ever happen in here!"

I wonder what is but instead of asking I just grab our receipt and we find a table. The Wrap It Up box buzzes a few minutes later and I grab our food and divide it between the two of us. "So, tell me all about the plug. Kinda crazy, you said?"

"God, where to start! First off, you see how I'm walking. This this is seriously huge! I've never walked around with anything that stretches my sphincter so wide and leaves me so open like this." I give a huge grin, loving that you use proper terminology, and loving even more that you're using it in public. "Next, I can feel every whoosh of air that blows up my skirt inside of me. And, I mean, I'm wide open! Anything could, uh, happen at any moment! Kinda scary. Oh, and you putting your finger in was so, SO strange; there was that tickley feeling of having someone's finger deep in your ass without any feeling of it pushing in." You stop and sigh, hunching your shoulders forward. "How long do I need to keep this in to be a Good Girl??"

"You can give it back to me as soon as lunch is done. Or I can take it back when we're done. Either or." I see you shimmy your ass so the plug is in contact with the seat, holding the sides of the chair with both hands as you bounce a few times as if to show your approval instead of voicing it. I hear a muffled - tap tap tap - as the edge of the plug strikes the seat.

"Ok Daddy. I can do that," you say batting your eyelashes at me before taking another slurp of smoothie.

The conversation turns to the kind of small talk that reminds us that it's not just sex between us all the time. We talk about how yet again, half the office took the day off because it's Friday. We talk about how perfect the weather is and about maybe going for a hike tomorrow. You fill me in on the latest drama with your sister.

Mid-sentence, you freeze and your eyes go wide. "Napkin!" you say forcefully through clenched teeth, trying not to let anyone else hear. I hand you one and you crouch down next to the table pretending to fix your shoe but I can't see what else you're doing. When you're done, you sit back down and I hear the tap of the plug against the seat again. Looking straight at me with half closed eyes, you explain "The last of your cum just leaked out of me while we were talking." I get a good laugh out of that one.

We finish up soon afterwards and just as we're gathering our things, the guy from behind the counter walks out. He's been busy ever since we ordered with mostly grab-and-go customers but finally, it's just him and us. "Hey there," you say as he walks up.

"Hey, um, I didn't have time to ask earlier but haven't I seen you come in here a few times before?" he says nervously,

"Yeah, I do lunch here every couple weeks or so," you say without a hint of embarrassment.

A goofy smile crawls across his face as he nods over and over with his teeth exposed, saying nothing. After another long uncomfortable moment, he finally exclaims "Cool!" That's followed by another long pause and more nodding, after which he finally realizes how awkward he's being.

"Hey, well, uh, I just wanted to say that if I can ever help you out again with anything, you know where I'm at," he says, shifting eye contact between the two of us, slightly embarrassed at what he's implying.

"Hmmm, help out how?" I ask. My mind jumps between a dozen possibilities but before he can reply, you grab my hand.

"I have five minutes to get back to work." You turn to him and step so close that your bodies are nearly touching. "But I promise I'll stop by if I ever need any . . . help." As I hold the door for you, you pause in the doorway to look back at him. He's still staring right at you as you flip your skirt up, letting him read the words "Anal Only" across your panties. The toothy grin immediately disappears as his mouth pops open in shock as you pull the panties aside revealing the tunnel plug, then drop your skirt back down and confidently walk out to the street. I shrug my shoulders and follow you, leaving him slack jawed in the center of the store.

We walk the three blocks back to your building hand in hand, giggling and making jokes about the look on his face. As we wait for the crosswalk at the block before your work, I stand directly behind you and put my left hand in my jacket pocket. Holding it out around your left side gives us the most minuscule amount of privacy. With nothing on our right but cars, it's just enough privacy for you to let my right hand wander down, put my middle finger all the way in until I feel your warm, slippery insides, catch the tip of the plug, and start to pull. It comes slowly, just as it did in the video you sent. I can feel the resistance of your stretched asshole nearing the flared end when the light turns to WALK. Leaning forward, I whisper "well, start walking". I stand still and can feel you step out over the curb. Your foot hovers in mid-air briefly as I hold you back by only the plug, your whole body weight trying to free yourself. Your skirt falls back down as your muscles finally let go causing you to fall forward and stumble to catch yourself. I follow close behind watching your erratic gait, knowing your love tunnel is recoiling from the removal of such a big toy. By the other side of the street, you've regained your composure. To anyone else, it would've just looked like you tripped stepping off the curb.

I carry the plug using the two fingers that were inside when I pulled it out, leaving it exposed for all to see. It only takes a moment to jog the couple steps and sidle up alongside you. Tilting your head slightly toward me, all you can say is "Wow! I I can NOT believe we just did that. In fucking public!" When we arrive in front of your building you ask "so, any instructions for the rest of the afternoon?"

I hold the plug up with my two fingers. "You're done with this so I'll take it back to your apartment and put it with the others. For this afternoon, all I ask is that you send me a picture. What's in that picture is your choice but it needs to be something that illustrates to me that you've truly embraced your inner anal slut. I'll be here at five o'clock sharp to pick you up."

"Of course, Daddy. Watch your phone!" Then you lean in closer while opening the naughty side of your purse and pull the black plug out just enough for me to see. "But you can be sure I'm going to put this back in right away after I void. Good girls stay plugged all the time," you say in your sultriest voice.

Public play. Confidence instead of bashfulness when strangers realize how big of a slut you are. Using varied terminology for body parts during dirty talk. Going above and beyond what feel I can ask of you. Deep penetration and screaming anal orgasms. I can't believe how lucky I am.

"You are the best fucking woman in the world. Every time I see you take pleasure from fucking and toying and defiling your asshole, I know there has never been a better woman than you. You'd better be careful or you're going to end up fulfilling every deep dark perverted fantasy I have. And who knows what I would dream up then" I say as I pull you to me and kiss you. You smile a wide, contented smile and turn around without a word, walking towards your building and eventually disappearing through the rotary doors.