The Double Anal Weekend Ch. 01

A jolt of adrenaline shoots down your spine as your phone vibrates signaling a text you feel like you've waited forever to receive. "I've landed" is all it reads, but the message is clear. All of the preparation and teasing that's gone on over the last few weeks is now prologue. Equal parts fear and excitement prove that it's true; sometime over this weekend, you're going to try double anal.

There's probably an hour until I arrive, but you still rush to the bedroom as if walking would somehow disappoint me even though I'm on the other side of the city retrieving my luggage. You sort through both drawers of sex toys to find one that fits my instructions from earlier in the week: whatever you can handle comfortably that will stretch you the widest. You grasp the glass plug you've been wearing since you woke up and pull firmly. Even with more than two weeks of daily training, you're always amazed at how solid your grip is after wearing one for a few hours. You pause as it reaches maximum width to savor the stretch. It's been days since there was anything close to pain, and you love how easily you can open up now. You're proud of yourself and can't wait to show Daddy how far you've come. It pops out, and immediately your other hand pushes a much larger glass plug up and inside without hesitation. You let out a long groan, knowing it's the last time you'll have to do it yourself for the whole weekend.

After cleaning the smaller one, it's straight to the closet. Knee-high green socks, a tight black lace corset that leaves your pert little breasts exposed and snaps open underneath for easy access, garters, fingerless lace gloves, and my favorite necklace that sort of looks like jewelry and sort of looks like a collar. Your hair is already up, done exactly as I had requested. You put the finishing touches on your makeup and hurry to the living room. The floor length mirror near the entryway helps you snap picture after picture of yourself, changing the lighting and your pose until you're happy with three or four of them. You then bend over and make sure the looped end of the glass plug is obviously visible as it pushes out from under the corset, and take one last picture. I smile in my Uber as I hear the tone of an incoming text because I already know what's waiting for me.

You busy yourself as you wait by making sure the bedroom is perfect: new sheets, candles everywhere, all of your toys out on display, clean towel, fresh bottles of lube, lavender essential oil in the diffuser, perfect low lighting, and a tripod that can hold either of our phones. One of my rules is "If there isn't proof on my phone, it didn't happen". At first you were so hesitant about it but by now, you've climaxed watching yourself get sodomized so many times that you don't even remember it was something you originally resisted. The video of your first DP session is by far the one you've watched the most, and it just happens to be the night that the seed was planted for what eventually became this weekend.

The videos of that night are long and in multiple parts, and you've watched one part more than any other. We had been switching between your holes for what felt like hours and you were sure that we were ready to finally mount you at the same time. You were riding our friend who had completed the threesome and felt lube drizzling down your ass crack. I came up behind you and before you knew what was happening, my cock was buried halfway into your pussy alongside his. You cried out and swung your head around, exclaiming "Baby! Wrong hole!!" I chuckled with devious satisfaction seeing how shocked you were as we both started pumping in and out of your pussy simultaneously.

"No. It's. Not," I had replied, matching each word with a thrust into your savagely tight cunt. "Someday you're going to do all three kinds of DP for me. Tonight, you're getting both double vaginal AND the thing you've begged me for. Good old DP". As I said the last few words, I slipped out and buried my pussy-soaked cock deep in your ass. That's the moment that always makes you cum when you watch it.

Since that night, you've known that eventually you were going to take two cocks in your ass at the same time. Sometimes when we found ourselves talking dirty about it, you were confident you'd be able to take us both. Other times, I could tell you were timid and were questioning whether you could do it or not. The training you'd done over the last couple of weeks built confidence but every time you really thought about what it was going to feel like having two men inside your backdoor, there was more than a little fear deep down inside you. As you're daydreaming about all of this, the buzzer goes off for the front door and you snap back to the present. "Too late to back out now" you think to yourself. "What have I gotten myself into?"

You hit the button to let me into your apartment building, only to get a text a moment later. "I need you to come down and get the door for me. I have two suitcases after all." You catch a glimpse of yourself in the mirror: nipples exposed above the fancy lace of the corset, an obvious bulge poking out between your ass cheeks, and an overall outfit that screams "fuck me!"

You text back in disbelief "in this outfit, Daddy??"

"Yes, but I'll allow you to wear that short leather jacket you like. Hurry." I reply. You grab it off the hook next to the mirror and tie the belt around your waist feeling the rough inner lining against your nipples. You try with both hands to pull it down and make it longer and immediately realize how stupid that was. It's leather, after all. It's just long enough to hide your butt, but no longer. Unless your posture is completely perfect your plug will still betray you but you have no choice. You take a deep breath and exhale hard enough that your hair poofs up for a moment. Then you close your eyes, open the door, peek out to see an empty hallway, and rush to the stairwell as fast as you can manage with your huge glass plug in.

There's no one in the stairs as you enter but just a few steps later you hear the ground floor door open. You inhale sharply as a roster of neighbors you hope it isn't flash through your mind. On the second floor landing you pass two women from a cleaning service who you've seen around the building before. The first one ignores you and keeps walking but the second one immediately notices how out of place you seem. As you pass, she takes a long look from your hair down to the tips of your green socks and back to your eyes. She smirks and cocks her head to one side as she giggles a little, then continues up the stairs. You try to put it out of your mind as you rush down to the front door.

I'm already waiting in the lobby, a room the size of a small studio apartment with overstuffed chairs on both sides of a main walkway that connects the entrance vestibule with the hall that goes to the stairs and the first floor apartments. The cleaning ladies let me in. All of your anxiousness and apprehension melt away as you wrap your arms around my neck and I lift you up for a kiss. "Hey Daddy!" you say in your flirtiest voice.

"Well, don't you look marvelous today!" As you kiss me again, I lower you until your feet touch the floor and slip my fingers into your jacket, pulling it open just far enough that I can see your naked breasts within. My other hand reaches around to inspect whether my instructions were followed and I quickly find that they were. I grab the glass ring at the end of the plug and pull until I feel it slip out, then back in and out again. You close your eyes and concentrate on the feeling of being so brazenly invaded and so exposed, putting your fears of being seen aside as much as you can. After a few strokes I pop it back in and hold you at arms length. "Daddy's so lucky to have such a giving and obedient girl in his life." I say. You blush and courtesy.

"Now, grab that suitcase and lead the way. It's full of things for you so it's only fair that you're the one who carries it." I follow you to the stairs and watch intently as you struggle a little with the bulkiness of my case. From below you on the stairs I watch the outline of the plug beneath the bottom of the corset twitch and pulse, slipping out a little as you relax and then snapping to attention as you flex just the right muscle. I can tell you're putting on a show for me, shifting your weight from leg to leg on each stair for maximum effect. At the third floor landing, I lean forward and grab the door, smacking your ass as you go by which elicits a giggly little yelp. Neither of us notice the drop-dead beautiful man in the hallway who just saw that.

"Oh, um, ah . . . Hi Marcus," you say, suddenly remembering how you look. You hold the suitcase up a bit in front of you trying to hide behind it, making sure your ass is pointed directly away from him. "This is my Da . . . ah, my boyfriend".

"Nice to meet you", he says stumbling over his words in an unidentifiable South-American accent. He glances at me for only a fraction of a second, returning his stare to you and your provocative outfit. "Lucky guy!" he says back to you as he passes us and starts descending the stairs.

"A friend?" I ask as we walk to your door.

"He lives down at the end of the hallway. And I think he thinks I'm a slut now!" you say in an exasperated tone as we reach your apartment. You put the suitcase down but before you can get the key in the lock to open the door I grab your hair and push you up against it. My breath is hot on your neck as you feel my weight pushing against your back, pinning you in place.

"Well, would he be wrong in thinking that?"

"No Daddy! He wouldn't!" you reply as if admitting a secret. I can feel the end of the plug grind against my groin as you savor being restrained. Your free hand finishes with the lock and I push you into the apartment, locking the door behind me.

"I do apologize for being so late. Feels like that flight is always delayed. I think I can make it up to you though if you'll take that suitcase to the bedroom and open it." You walk down the hallway immediately to your left that connects the combined area that serves as kitchen, dining space, and living room with your bedroom and plop it down on a footstool in the corner. To your surprise and delight, it's packed full with presents. Your mouth drops open as a huge smile grows, turning your head towards me.

"All for me?" you exclaim giddily. You grab for the nearest one but before you can start opening it, a hard, crisp smack rings out across the room as I strike your ass with an open hand. You freeze, afraid to disobey me again.

"There's an order to things. Don't get ahead of yourself." I say sternly. You stand rigid at attention from the unexpected pain and obediently set the present down. "Each one is numbered. Please pull out numbers one through three and sit on the bed." You find number one, a rectangular box a bit bigger than a TV remote. Number two is nearly identical and number three is obviously a clothing item of some sort. You half-sit on the edge of the bed, leaning to one side to give the end of the plug enough room, trying not to show your excitement in seeing what I've brought you. You rip open the first to find a set of seven smallish anal beads connected by a thin nylon cord.

"Ooooh!" you exclaim. You can guess what's in the second box, and you're right. Same beads, but four of them that are almost twice the size. "Mmmmm" you growl with a devious grin on your face. You put a finger through the ring on the end of each one and hold them up, inspecting them and dreaming for a moment about how the big one will feel.

"Leave the third present on your nightstand, take everything but your stockings off, and get on all fours on the bed with your ass pointing towards me." I command. I make sure to set up the tripod and phone in a good spot as you position yourself. We always seem to forget to worry about it once we get down to business. I start recording.

I walk to your dresser where all of your toys are displayed and grab a flogger. I slowly approach you from behind, flopping it into my open hand a few times so you can hear the muffled sound of leather against leather. Two sharp strikes echo through the room, one for each cheek. I alternate between left and right, sometimes quickly bouncing between the two and sometimes hovering for what feels like an eternity, watching you wiggle your bottom in anticipation of the next impact. Only after you've turned a bright shade of pink do I grab your plug and gently start to remove it. "Are you ready for this weekend? Do you really think you're a big enough slut to do this?" You release your grip and the plug pops out as I say the final word.

"Yes Daddy! Yes I am!" you reply.

I force the plug back in much more quickly than I extracted it, eliciting a deep groan. "Sorry, that's not enough." Two more sharp smacks ring out, each cheek receiving its due with my open hand. "Make me believe it." I grab the plug again and start fucking you, awaiting your reply.

You look back over your shoulder at me and we lock eyes. Your voice lowers, taking a serious and determined tone. "Daddy, I will be the best anal slut you've ever seen. You're going to be shocked at how nasty I can be!" Both hands reach back as you spread yourself even further open. "I'll take anything you want in that whore ass. Treat me how you always say I deserve to be treated. I'm ready to be your double anal slut!" I choose not to reply with words and instead pull the glass plug all the way out and toss it on the towel. I grab the bigger set of beads in one hand and tell you to sit on the edge of the bed and undress me. You zealously strip my pants, underwear, and socks off and almost get your lips around the head of my cock before I grab one shoulder and force you back.

"Legs straight up!" I bark. You obediently grab your legs behind your knees and pull yourself back, presenting your most private of places. Your asshole shows the use it's seen during the last few weeks of training and looks absolutely perfect, a trickle of lube dripping from a slight gape cultivated by your daily workouts of a noticeably altered, muscular hole, all framed by a perfectly round, pink ass. I admire the fruits of that training for a few moments, knowing that you've taken to heart the many pictures I've sent as examples of an ideal you should work towards. Those pictures are always of beautiful women posing nude with nether regions that obviously show their training and use, be it an effortless gape or a clearly swollen and protruding ring of muscle, or the darker shade of skin that surrounds a well-trained sphincter. "This is what a real woman looks like back there," I would repeat. Now I can see you've truly taken my words to heart.

Lube in hand, I press the first ball against your well-exercised hole which eagerly swallows it. The second one goes in just as easily, so I immediately push with the third. Your back arches as you feel the first two being forced deeper into your anal cavity. I pause at the widest point to watch you squirm and hear to your reactions. You shimmy yourself side to side briefly to make room and in a moment it disappears. A satisfied moan escapes your lips and lingers for a moment. "Is that three already?" I nod as I play inside with a finger, penetrating your anus in order to push the third one slightly deeper.

"It sure is. One more to go." I start with the fourth well-lubed ball and your moans increase in volume and urgency. Your hand slithers down across your abdomen to your clitoris, tracing soft slow circles around it that quickly hasten.

"Ohhhh, fill me up! I've missed this so much!" you moan, fully enjoying the first contact I've had with your ass in three weeks. Your hand slips further down and meets mine, both of our fingers pushing on the last ball. "I told you I'm a good anal slut, Daddy," you say as your ass devours it, driving the other three even deeper. Your head slumps back on the bed as your fingers return to your clit, the speed of your circles betraying how good it feels to be filled. As you play, I walk bottomless around the bed and climb up onto it, a knee on either side of your head. You're still on your back and when your eyes open you lunge for my engorged manhood, hovering only inches above your mouth. Sloppy, wet circles traced with your tongue around the tip begin to lube my cock, quickly followed by your lips slipping further down my shaft. I brace myself by putting a hand on the headboard and start pumping slowly, making love to your mouth. Savoring the feeling, I close my eyes and concentrate only on your willing tongue, flirting and flicking and flying across my shaft as I thrust deeper. After a couple minutes I open my eyes and reach out to catch the ring on the end of the beads with one finger.

"Keep your head back and your mouth open" I say. I lean forward, thrusting to the back of your mouth and down your throat while pulling one bead to the brink of popping out. As it escapes, I pull my cock back to let you take a breath. Another thrust pushes my cock even deeper and at the same time, the fourth bead pushes past the doorway and back inside. A too-brief moment to catch a breath is all that separates the last thrust from the next, each accompanied by the fourth bead popping in and out. I'm now so deep that my balls slap against your nose each time I push. Tears form in your tightly-shut eyes and roll up your forehead as you fight the urge to pull away.

You hear the instructions from my last visit in your ears. "When you gag hard, you get a break". Deep throat is something you've tolerated but never shown a talent for in the past but tonight, the combination of aching for my touch and the drive to fulfill every single one of my wishes gives you the mental strength to override your natural reflex. You feel the rough sensation of something so large and foreign uncomfortably stretching your throat while at the same time knowing you could cum just from the attention your ass is getting. The hand on your clit dips fingers past your labia and into your pussy, hitting your G spot causing your body to convulse as your first orgasm begins to crescendo. Right as your ass starts to contract around the beads, it all becomes too much and you gag on the full length of my cock. I don't move. Moments later I feel the spasm of a second, deeper gag reflex and I pull all the way out, cock covered in spit and throat lube. You gasp for air, coughing and swallowing, fingers still madly working your clit. Your lower half seemingly ignores how hard your upper half has been straining for breath as the crashing intensity of an orgasm nearly a month in the making overwhelms you. I hold the ring on the end of the beads, watching you writhe from the full force of your orgasm, involuntarily pulling two of them out of yourself in the process. As it ends, a tiny bit of squirt hits my hand and trickles down my fingers which makes slipping the beads back in even easier.

Thick spit covers my cock and most of your face as you finally catch your breath. I step back and grab the smaller beads, dangling them above you. "Need me to do that to you one more time or was that enough foreplay?" Your eyes are filled with frantic passion, your chest still heaving from the deepest throat job you've ever given.

"My ass needs you NOW!" you yell. You start to roll over but I push you back onto your back and walk around to the original side of the bed. "Count for me" I say. I pull the larger beads out as you moan each number.

"One, two, three, fooooourrrr," you say, hovering on the last one as I ever so slowly remove them. I set them to the side on the towel and rub the smaller ones around my cock, lubing them with your spit. They're a set of 7 beads, each about an inch wide. I pull your hips forward so your ass is nearly off the edge of the bed, push your legs back so you're holding them again, slip three balls in, and let the rest dangle. As I lean forward, cock in hand, you let out a half moan-half sigh that tells me all I need to know about how much you've missed this. I aim right at the center of your opening and slip in without resistance. "OOOhhhh yeeessss, Daaadddyyyy!" you moan.