Double Anal Story

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Double Anal Story
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I 'go public' after having lived as a Woman for months.
Was I fucked by my Son in a masked gangbang filming.
A visitor comes to town. But how human is she...
Rachel goes on a date with the devil.
Son catches mom getting gangbanged by a bunch of BBCs.
I found out my daughter is a pornstar.
Son finds out mom is a filthy escort.
Mom meets the boys while Iris gets worked out!
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Brief story of a couples attempt at double anal.
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All night I had been teased. Pics of her masturbating, fingering her sweet pussy. Penetrating herself with the dildo and, finally, the mirror pictures, with the large fleshy dildo buried in her tight ass.
I'd been ready to blow five, six hours ago, even before those pictures, but they took me to a whole new level of turned on.
The pictures alone would've ensured a raging hardon for hours, but she accompanied them with constant updates, telling me how good it felt, to have her ass penetrated deep and wide, gently pressing those spots that I've hit before, only much harder.
After hours of this torture I drive home, distracted by the thoughts hurtling through my head. In the last hour we've discussed my long held fantasy to have two dicks in her ass, stretching her wider than ever.
We've tried in the past, of course, but its never worked, but now, with her sexdrive in overdrive, she seemed keen too.
Arriving home I rush up the stairs, erection straining against my uniform trousers, desperate to get my hands on her. She lays on the bed, reclined, naked, soft skin a temptation to my lips.
Running my eyes over her voluptuous figure, I notice the lack of a dildo. Climbing onto the bed I tell her that I had hoped to give double anal a try.
Smiling, she tells me we'll try and fetches the dildo, thick and veined, and the lube and begins working it into her tight hole as I strip frantically.
She lays on her side, legs curled, dildo buried deep in her ass, waiting for me. Coming up behind her, I stroke her shoulder, her back, reassuring her that I wouldn't hurt her, that I'll be gentle. She reaches back and smears cold lube onto my now solid, throbbing cock.
Moving forward I rest the head against her skin, tight against the dildo, ready to push into her. Slowly I drive my hips forward, the glans pressing against the tight ring of muscle. She breathes deeply, trying to relax.
My cockhead slides ever so slightly into her ass when, suddenly, she clamps down and grunts. Worried about hurting her, I pull back, asking her if she's ok. She tells me she's fine, but the stretching pushed her over the edge into orgasm. We try again, getting a little further before her muscles squeeze the tip of my cock into the side of the dildo.
Withdrawing, I line up again, pressing firmly against her ass, once again feeling her body shudder as climax rips through her.
Four or five attempts later, the glans is inside, but only barely. Reluctantly we agree to try with a longer but thinner dildo. After a few moments, she's penetrated once more, this time with a plasticky cock.
Lining up beside it, we start again, almost instantly pushing her into climax again. Panting, she tells me not to stop next time and see where we get to.
Pushing again, I feel her muscles stretching to accomodate my cock alongside the dildo, before her body tenses and she groans, the stretching triggering yet another orgasm. I keep pushing, getting half my thick cock into her ass, all the while orgasms shattering through her body, causing her to shake violently.
I stop, holding my hips in place, allowing her to calm down. After a moment she tells me she's ready and I start thrusting slowly, working a little more of my shaft into her ass each time until I'm ¾ of the length into her ass.
The friction against the dildo is not particularly pleasant, but the knowledge of her ass being stretched so blocks out the discomfort from the dildo pressing against the underside of my cock.
As my foreskin pulls back, the hypersensitive part of the glans is exposed to the friction of the dildo, causing my own orgasm to approach rapidly.
"I cant hold off much longer", I tell her, causing her body to lunge into another series of wracking orgasms as my cock works gently in her ass before, three or four thrusts later, my cock swells and I hit the plateau, my entire body tense, breathing almost stopped before, almost painfully, the convulsive spasms start, pushing my seed into her ass.
We lay together for a moment, neither of us moving before, reluctantly, I withdraw from her. She pulls the dildo out, its pink surface coated in lube and my cum.
Nice start, hope there's more, only disappointment was that it was a dildo and not another cock.
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Anal The Double Anal Weekend Ch. 01
She's trained so hard but can she really do double anal?
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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.
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 t
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