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fetishfairytales2 · 16 hours

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Happy Birthday Sissy! Pt. 3

Heather and Brandon are original characters created by @wittlesissyb4by in his fantastic series “Besties”, which this blog expands on. Please support him through his Tumblr and his SubscribeStar. ——————————————

I had finished most of Brandi’s makeup while she was cuffed to the chair in front of the vanity. “Just a few more touches girly,” I said into the mirror giggling. I pulled the paci gag from Brandi’s quivering lips and slicked on the bold red lipstick on. "This shade is called 'Fuck Me Red', how perfect!" I sneered, After a few hard slaps and some threatening to let Daddy handle her temper tantrum, the fight had drained out of her and she stopped resisting me. "Oh, and make sure you don't ruin that mascara with your sad little tears, Sissy. Or whatever else will be dripping down your face later!" I teased.

"Oh Brandi, honey. I can see the excitement in your eyes for your special celebration!” I cooed, staring into her eyes; “Everyone is just dying to see the sissy birthday girl! But before we go over the guest list, I have to give you a little heads up." I crawled into her lap, getting cozy and teasingly rubbing my ass against her caged and diapered cock. I pulled her face close to mine, looking stern and deathly serious. "Just remember, sweetie, if you mess up AT ALL today, don’t do exactly what I ask or don’t behave like the perfect little sissy, I promise I'll make your life even more miserable than it already is. And trust me, I have some creative ways to do thatâ€¦"

I flashed my sweet Mommy smile and spoke in my sing-song voice again. "Now, let's think about all the friends coming to see Sissy Brandi today, shall we?" I raised all ten fingers in front of her and continued, "Mommy and Daddy Conner will be there, of course." I lowered one finger. "And let's not forget about my sister Maddie,” I put down another finger. “Oh, and Kylie, she just loves seeing Sissy Brandi." I dropped yet another finger. "And her handsome boyfriend, Brad, will probably be joining us too." I pinched her cheeks and cooed. "There's also Ms. Lyndsey, and she's bringing her boyfriend Marcus. Remember him?" I booped Brandi's nose as I lowered another finger. "You weren't very nice to him last time when you got drunk and screamed all those mean things at him. But that was old Brandon, not my sweet mincing Brandi."

"Oh, and how could I forget to mention my girlfriends Rachel and Kelsey?" I cooed, taking out my phone and showing Sissy a photo of the three of us on my Instagram. "They'll be joining us for your little party, too! And don't worry, they know all about your new lifestyle. I made sure to invite their boyfriends as well."

I scrolled through my phone again, finding a shirtless photo of a man with a sculpted body. "Guess who it is?” I laughed; “I promise, you're going to hate this," I giggled with delight. Without waiting for a response, I zoomed out on the photo. "Remember Mark? The one you were oh so jealous of when he was my personal trainer? Oh, the silly sissy thought I would cheat on him! No I would never...until you were in diapers, of course. Then I fucked Jermaine and every other man I could! So yeah, he’ll be here too!"

“And him of course,” I smiled wickedly, watching Brandi struggle against the cuffs as I held up my phone in front of her face. "Shh, shh,” I teased. “Don't worry, it was twiceâ€¦in one night. Oh, and then another two nights after that! He's just too hot, isn't he?" I giggled while scrolling through naked photos of my coworker Grant and I in the same bed I used to share with my cuckold. I reminded her of how jealous she was when she met him at my job’s Christmas party, saying, "I told you not to worry about him then. Nothing would of happened! But no, you just had to go and cheat on me with that slut Sophie..."

I paused, giving a flirty wink and revealing a screenshot I took from someone else's Instagram. "This is her, right?" I teased, showing a picture of the attractive young blonde who worked as Brandi's intern and her colleague, Chloe. The sissy was practically knocked over with shock. "Oooh! Surprised that I found her? I did some digging sweetie. Of course I found the woman you thought was worth throwing our whole relationship away for! And want to know something even more fun? She's coming too! And so is Chloe! But shhh, they think it's just a regular old birthday party. Oh, the fun surprise they're in for! I bet work is going to be interesting on Monday, huh?”

"Oh and sweets? That's not all of the invites for today," I whispered into her ear, removing her handcuffs and helping her up from the chair. "But don't worry, that's a surprise for later!" I grabbed her hand and spun her toward the door, causing her comically short skirt to puff out even more. "Now let's go say hello to our guests," I giggled, giving her a playful spank.

#humili sissi

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fetishfairytales2 · 3 days

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Front Row Seat

I was practically skipping with excitement as I pranced through the dimly lit playroom and flicked on the lights, instantly illuminating that poor unsuspecting sissy. “I tried to do it the easy way Brandi,” I giggled, sauntering up to her from the front, loving how she shook with fear listening to my heels echo against walls. “But I guess naughty sissies only understand the hard way, huh?” With her head trapped between her legs like that, she had no clue what was about to happen. It was so fucking delicious watching her start to cry before I even laid a hand on her. “Oh, and let me tell you, Daddy is definitely going to be giving it to you later...in a really hard way.” I couldn't resist teasing her as I stroked her bare back, watching those little goosebumps pop up all over her body. Poor little thing never stood a chance.

"Aww, is the sissy crying already?" I cooed, standing above her and making sure she couldn't see me yet. "Don't worry, sweetie, Daddy isn't even home from work yet!" The tears started pouring even harder, the sound of her pathetic sobs muffled by the pacifier gag in her mouth. "Let it all out, baby, Daddy Connor is going to give you a real reason to cry soon enough. But first, I'm here to help you get ready for him!"

I got down on my knees and playfully kissed her on the cheek. “Well, you certainly aren’t a brave little girl, but that’s okay,” I teased, patting her on the bottom; “Mommy thinks it’s cuter when you cry anyway!” I reached behind my back, revealing a pair of scissors. “Oh relax you drama queen!” I laughed when Brandi flinched as much as she could in her binds; “they’re for your diapee!” Without another word, I swiftly snipped a hole in the back of the pathetic sissy’s diaper. "There, there," I taunted as I inserted my finger into the new opening, catching her off guard. "Oh, did that surprise you?" I smirked as she jumped.

"Can you guess what the hole in your diaper is for Sissy?" I taunted, tracing the hole with one perfectly manicured fingernail. "Well, I'll give you a hint: it's definitely not for you to make messies." With a dramatic pause, I reached behind my back and revealed the giant pink butt plug, just waiting to stretch and fill up that sissy hole. "Open up, you little slut," I commanded, snatching her pacifier and replacing it with the plug. "Get it nice and wet for Mommy."

I gave her cute, tear streaked cheek a little squeeze as Brandi bawled her eyes out; “Hush, hush sweetie,” I cooed in my mommy voice; “you'll be thanking me later, you know how much bigger Daddy is than your plugs.” She stared up at me, crying harder again. “But we can't have you getting too loose can we? That’s why we stick with a smaller plug! Now take a deep breath..." I chuckled, removing the plug from her mouth. She tried to compose herself but couldn't stop crying. I smirked and waited just an extra second before jamming the plug home. I had to really twist it in when it stopped halfway, laughing as Sissy moaned and bucked her hips. “The anticipation just makes it so much more satisfying, don't you think?” I asked with a firm spank to her new tormentor once it was all the way in.

"Now listen here, sweetie," I hissed in her ear, "hold onto that while I go get myself prepped. This is gonna be soooo much fun," I cackled and grabbed onto her hips, looking down at her begging eyes. "Normally, you'd be too busy eating my amazing pussy while Daddy has his fun with you. But tonight, you get a front row seat to watch the whole show. Lucky girl, huh?"

#humili sissi

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fetishfairytales2 · 4 days

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Besties 9 (Story)

This was originally written as a continuation of a story by @wittlesissyb4by called Besties. Check out all their fantastic stories on Tumblr and SubscribeStar.

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I wiped my cum-covered finger across his nose and the bit of his lips that were poking out from the gag. "There you go, sissy, enjoy!" I said with a chuckle, wiping the rest of the cum off on his hair. "Looks like you were super desperate to get off, huh sissy?" My eyes widened and I nodded excitedly, "Yeah, I bet you were just dying to cum, right?" I laughed as his face turns bright red with humiliation.

“Remember,” I rubbed his head gently and ran my nails down his skin. I smirked as his hips begin to move faster in response to the vibrator. “I told you not to make any messies! But you just couldn’t listen could you?” I mocked, pressing the vibrator closer to his cock. “By the the time I’m done with you Brandi, you’ll be begging for your chastity cage back.

I couldn't contain my laughter as I saw the fear in his eyes. I enjoyed watching him squirm as I silenced him with the pacifier between my fingers. "Oh, you love sucking on that little dick, don't you, sissy? I mean, Daddy Conner's twice as big and Mommy can't get enough of it!" As I lightly tickled his thighs, I could feel myself getting turned on all over again. Seeing him struggle against the vibrating Hitachi was a major turn on for me.

He moaned in pain as his body fought against the increasing intensity of another orgasm. I leaned in closely, my hair brushing against his thighs. I playfully giggled, letting my breath graze his naked balls. "Aww, does little sissy feel extra sensitive?" I taunted, putting on a baby voice. "Is Mr. Buzz Buzz being a meanie to you? Poor thing!"

“Isn’t this what you wanted Brandi?” I laughed over the buzzing of the wand. “How about a little distraction? Your mommy sent me something special just for you. And trust me, I know you'll love it!” I snuggled up to the loaning sissy and held my phone in front of his face. “Here, take a look at this,” I giggled, forcing it into his face. “Oh, and don't even think about resisting, Brandi. You know you want to cum again and again. I pressed the vibrator even firmer against his cock. “And you're not getting off this bed until you've drained every last drop from those pathetic little balls of yours. So pay attention, cucky!”

I clicked on the video Heather sent earlier and grabbed Brandi by the hair, forcing her to watch the screen. Watching her immediately start crying was literally the most hilarious thing I've ever seen. Poor Brandi’s freaking priceless. He was being forced to cum watching the love of his life be a total whore! The video was so hot too! Conner was recording Heather being a total slut and begging for him. She's on her knees, naked and looks like a total hottie. Her nipples were rock hard, and her tits were bouncing around while she looked like a total pornstar on her knees playing with herself. And then she looked up at the camera with these desperate, horny eyes and said "please, sir, can I taste your cock?" Wow she was really going all out for him!

“Fuck this is hot,” Conner was mosnjng, gripping his hard cock and stroking it on camera as Heather willingly humiliated herself. "Mm," he moaned with satisfaction, "tell me why you're such a desperate little whore, darling." Heather shuddered and started moving her hands faster, clearly getting closer to an orfasm. "Because my loser of a boyfriend has a tiny, useless dick. Now he’s a fucking sissy and I need a real man like you! Please, sir!" She begged, moaning and twisting her nipples as Conner watched and laughed.

The camera was showing Heather, her hair being gripped by Connor as he pulled her towards his massive dick. She delightfully licked and kissed every inch of his hard cock, taking it deep into her mouth and licking all around. With a smile right into the camera, she exclaimed, "Mmm, I love your cock so much, babe." "It's way bigger than his little sissy clitty." I could literally watch Brandi dying inside. It was so much fun.

“Fuuuckâ€¦” Connor moaned as Heather pleased him. She was really going to town on him, holy shit! She even licked his balls, sucking them one by one before going back to his dick. She was throwing herself at him! Connor’s groans were getting louder as Heather worked to make him cum. "Oh yeah, that's it, baby," Connor commanded, pulling her closer by her hair. "Take it all the way in! Shit, you're such a filthy slut..."

For Brandi, watching his girlfriend get railed by another dude was too much for him. And then adding the vibrator? Oh my god, he was crumbling right before my eyes. This is the ultimate revenge on such a fucking loser. Watching the woman who controlled him get controlled by someone he hates. It was amazing!

“Pretty hot, huh?” I smirked wickedly as I brought the toy even closer to the tip of his pathetic little dick. "Let's go, sissy," I taunted, playfully stroking the head of his cock. "Cumfor me like a good little cuckold, picturing your girlfriend begging for another man's cock. And every time you try to look away from the delicious video Heather sent you, I'll make you cum again. Got it?"

He nodded through his pathetic moans and tears, his eyes practically bulging with desperation and need. I knew at this point I had complete control over him. His breaths started coming faster and his moaning grew more urgent as I squeezed my grip on the toy even tighter. I watched his body shudder and shake, knowing he was on the brink of another forced and painful orgasm.

"Cum for me, cucky," I taunted, blowing in his ear and rubbing his convulsing chest. His breathing grew heavier and heavier until finally he let out a loud moan, his body quivering. His orgasm washed over him, causing him to shoot his load into the diaper below him again. I grinned triumphantly; “that one looked like it hurt sweetie!”

I kept stroking Brandi’s sensitive dick and snuggled back into his chest, playing the video again while he trashed in his bonds. Heather had Conner's hard cock out of her mouth and started to stroke it with her hands. She smirked and licked up his entire shaft, moaning seductively. I made sure to hold onto Brandi's head tightly, making sure he didn't miss a single second of the show. "You see, Sissy?" Heather teased, glancing at the camera with a smile. "This is what I do with any man who isn't you!"

"You better watch close, you diaper cuck," Heather laughed with a wink into the camera again, while Conner continued to run his fingers through her hair. "Daddy and I have decided that you’re going to be our sissy fluffer!" Grinning, she eagerly took Connor’s impressive shaft deep into her mouth, making sure to make a show out of deep throating him. "And let me tell you, if you don't suck Daddy’s cock like a little sissy porn star, you'll be in for a world of punishment! So you better make sure you know how to do it right!" With a seductive wink at the camera, she went back to work sucking like a slut.

Heather gave Conner a sly smile as she felt him begin to shake, knowing he was on the edge of orgasm. She skillfully used her tongue and mouth to please him, tracing along his shaft and then taking his balls into her mouth. She then moved down even further, teasingly licking around the base of his cock. "Oh yeah, baby," Heather moaned, muffled by his dick. "Just let it all go, cum all over my face!"

Heather was all over him, still stroking and working him over like her life depended on it. When he started moaning louder, she begged again; “please cum for me Daddy!” And boy, did Connor deliver. He shoved her face deep on his cock and held her there by the hair for what seemed like forever. Heather eagerly takes it all in, not wasting a single drop. So fucking thirsty. She even made sure the camera got a good shot of his load in her mouth. What a kinky bitch!

“We’re not done yet,” Connor grunted, grabbing Heather by the hair and holding her there. “Keep going,” he moaned, ordering her to stay still and keep stroking. Heather eagerly did as she was told, her eyes filled with arousal and anticipation as she continued to jerk him off. "Check it out, sissy!" Heather exclaimed, looking up at the camera with excitement. "See how much a real man can cum?"

Heather closed her eyes and let out a satisfied moan, the ropes of cum coating her face and lips. Kissing the tip of his dick, Heather looked up at Conner with a submissive expression. "Thank you, sir," she beamed, before glancing at the camera with an evil smile. "When I come home later and give you a big kiss, remember: you're tasting a real man's cum, sissy!"

Editor’s note: We are getting towards the end of this story, different stories staring the same characters will follow!

#humili sissi

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fetishfairytales2 · 5 days

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Happy Birthday Sissy! Pt. 2

"Oh God babe, I love seeing you handle Brandi like that! It just gets me so wet," I giggled, sashaying over to the closet. "I just love seeing Brandi being treated like the submissive bitch she is." I gathered Brandi’s party outfit from her wardrobe as Connor pulled down the side of the crib and dragged Brandi to the carpet. "Don't you dare move, you little bitch!" Connor growled, pinning her arms above her head. "And you, lucky girl," I cooed, kneeling back in between the diapered sissy’s legs and tickling her exposed belly, "you've got quite the view, don't you?" With Connor kneeling above Brandi's head, she was helpless to do anything but stare up at massive bulge of the man fucking his girlfriend.

I continued taunting Brandi as I untapped the sides of her humiliating diaper. “Oh, is someone craving Daddy's binky?" I couldn't contain my laughter as I pulled the soiled Pamper out from under her bottom and grabbed a wipe. “Babe?” I smirked at Connor, “the birthday girl is practically begging for it!” I tickled Brandi’s little sissy marbles and laughed as she started moaning behind her pacifier. “See? I think she’s really sorry that she didn't take care of Daddy last night….” As I wiped her clean, I just couldn't resist teasing the head of Brandi's dainty little pink plastic chastity cage with my perfectly manicured fingernails. I could see the desperation in her eyes as I slowly traced in between the bars.

“Shhh,” I giggled, Brandi was moaning like a true sissy slut now, it was obvious I hadn’t touched her clitty in days. "Don’t worry, sweetie, Mommy will have a special treat for you tonight if you behave like a good girl at your party. But for now, maybe Daddy will let you suck on something else..." I smirked at Connor and nodded towards him. "Open wide, sissy, don't be shy," Connor taunted, squeezing Brandi's cheeks before pulling out her pacifier. “Here comes Daddy…”

Connor, still in just his boxers, laughed cruelly and pulled his cock over his waistband, flopping it on Brandi’s face. “Kiss it slut,” he laughed, “nice and gentle for Daddy.” I shook my head, giggling as I watched my former boyfriend be further degraded. "Ugh, you sissy slut! Eyes up here, lips down there, don’t get too distracted!" I playfully scowled as I firmly spanked Brandi and taped her into a clean diaper. "I can't wait to show you your outfit for the party!" I said, rummaging through the pile of clothes next to me.

"First up, to go with your fresh diapee of yours, of course we have plastic panties!” I squealed excitedly, dangling the ridiculous things in the air. I was trying not to laugh, watching as Brandi craned her neck to catch a glimpse. The poor thing could barely see past Daddy’s massive cock resting on her lips and his balls smacking her on the forehead! “Look how adorable these panties are, Brandi! They're white and frilly, with the cutest pink trim. They're absolutely perfect for a pretty princess like you!”

I couldn’t help but giggle as her eyes went wide and she shook her head violently. “Aww, did you notice all the details? Yes you lucky little girl, those are little pink dicks embroidered on them! How cute is that? They're just begging for a sissy like you to wear them!” I flipped the panties around, making sure Brandi could see the humiliating design. She was trying to beg now; “p…please Mommy, pleas-“ Connor quieted her down by pushing his balls in her mouth. "Do you want to know why these are called 'Worry-Free Panties'?" I taunted with a smirk. Brandi immediately started crying and trying to escape when she saw it. It was so cute listening to her try to scream and gargle on Connor’s nuts. Not only was there a convenient hole in the back for easy access to her bottom, but above it, in bright pink lace, it read “Sissy Pussy”.

“Shh, shh,” I tried in vain to calm Brandi, honestly loving every minute of how much she hated this. “They’re called the ‘Worry Free’ panties because now no one has to worry about fussing with undressing you before they use that sissy behind of yours!” Connor had a firm grip of Brandi’s long hair. “Shut the fuck up and listen to her!” He screamed, working his cock as far down the sissy’s throat as he could, pinning her to the ground and shutting her up once and for all. I could only hear a little “mmph!” as he thrusted in and out of her mouth. “Thank you Daddy,” I winked; “sometimes naughty little sissies need to be put in their place!”

I held the panties up again, though I’m sure Brandi couldn’t really see anything but Connor’s ball sack now. Tears were still rushing down the poor darling’s face. “Now Brandi, you can be a good girl and dress however the fuck I want you to dress, or you can be a naughty girl and Daddy is going to get nice and comfy on your fucking face while you rim his asshole with your tongue, do you understand?!” I squeezed her sissy nuts as hard as I could and heard the fantiest of muffled screams. “If you’re ready to be a good girl for Mommy, moan like a good little sissy porn star around Daddy’s cock!”

“Oh, she’s definitely ready to be a good girl,” Connor smirked, beginning to fuck Brandi’s face faster now. “You better not make me cum you little slut,” he warned with a growl, slapping her across the cheek. “Good!” I smiled happily and slid the panties up Brandi’s legs. "Now for your cute little party skirt!” I taunt as I reach for the outfit beside me. "I know you're too busy right now to be able to see it, but let me describe it to you, just for my little sissy. Connor, could you lift her up for me." My alpha roughly pulled Brandi up by his scrawny body, his cock still down her throat, while I laid out the skirt, unzipped and ready for my sissy to wear.

I pulled Brandi’s arms to her side; “keep them there you fucking loser or Daddy is going to start getting meanâ€¦” Connor warned with a growl. "I couldn't resist a smirk as I began zipping up the dress on the poor cocksucker in front of me. “This is called the ‘Suffering Sissy’ dress! It's quite the name, isn't it? I found your whole outfit today on a special site that sells the cutest sissy clothes! Trust me, it’s named that for good reason. Not only is it scandalously short to flaunt those cute panties of yours, but it also has some...special features."

I couldn't resist snickering as I finished dressing Brandi. "Oh darling, you’ll notice this dress doesn't have sleeves. But no worries, I've got you covered with these adorable built-in cuffs! That way, when I zip you up, you'll be secured and trapped inside. That way you won’t be able to stop Mommy, Daddy, and all our friends fromâ€¦having fun with you! You’ll truly be a ‘Suffering Sissy’! Can you believe how freaking cute that is?"

"Daddy, could you stand up your pathetic little sissy girl for me, please? I need to doll her up before the party." Connor grunted, pulling his cock out of Brandi's mouth and roughly yanking her to her feet. Brandi was a sight to behold; her cute panties exposed under her skirt, her face covered in slobber and tears, her cheeks puffy and eyes bloodshot after being ruthless throat fucked by my boyfriend . "This way," Connor barked, dragging her over to the adorable pink vanity across and forcing her into the matching chair, gripping her shoulders to keep her still. I popped her pacifier back in her mouth for the time being, tying it around her head with the attached ribbon.

“What do you think girlie?” I asked with a giggle. Brandi's eyes welled up with fresh tears as she took in her outfit. The skirt matched the pattern and details of her humiliating panties, complete with little pink embroidered dicks. “Did you notice the theme? I laughed at her embarrassment. And to top it off, there was a pink ruffled "Sissy Cocksucker" across her chest, making her crumble even more. “There it is,” I patted her on the shoulder and whispered; "That’s all you’ll ever be. Forever and ever. Of course, all of this is a birthday gift from Daddy, so you better remember to thank him later. But first, let's show him just how much you love your final gift before he leaves you with Mommy to finish your makeup!"

I held the tiara up for Brandi to see in the mirror. She cried even harder as I placed it on her head. "As if you didn’t already know" I sneered in her ear, amused at her reaction. It was truly precious to see her crumble at the sight of such a simple little thing. The tiara was fitting for our little birthday girl, adorned with fake diamonds and silver. In the center, the words "Daddy's Girl" sparkled in faux diamonds. I couldn't resist winking and teasing Brandi, reminding her; “Don’t worry sweets, we both love Daddy and I don’t mind sharing."

“Why don’t you go shower and get ready?” I turned to Connor, “we’re going to have some Mommy-Daughter time while I finish getting her ready for her guests. They’ll be here soon and she doesn’t even know who’s coming yet!”

#humili sissi

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fetishfairytales2 · 10 days

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Happy Birthday Sissy! (Story)

"Oh my God today is going the BEST day ever!” I squealed as Connor and I snuck into the dark nursery. My poor, long suffering Brandi was all cute and cozy in her tiny crib-cage. “Just look at those footie pajamas!” I giggled. They were pink of course, with ruffles. They even have “Sissy Princess” across the front! “They’re too perfect for her!” Connor just shook his head; “looks more like a girl every day…”

I nodded excitedly as we leaned over the sleeping sissy. “I know right? And can we talk about her hair? It’s gotten so long! I totally braided it last night. We had a fun little girls night! I did her nails and her hair while I made her watch another of those videos you and I made,” I nudged Connor with a playful wink.

"Leave her alone, though,” I teased, “she's our precious little baby girl after all. Just look at her all trapped in her little cage. So adorbs!" I slowly opened the cage and gently called out to Brandi, but she was out cold. Ugh, typical. "Okay, Daddy," I pouted, giving Connor a pleading look. "Looks like you get to wake up our sissy princess."

Brandi was so cute, twitching in her sleep. She was probably dreaming of being a real man again.. “Mmm, such a strong Daddy!” I purred playfully, loving how Connor, all big and strong, just reached in and grabbed Brandi under her arms. He pulled her up to her sissy feet in the crib like a child. "Good morning, sissy-poo!" I taunted, knowing it would make Brandi cringe.

I loved how humiliated she always was, it was so much fun watching her squirm. But of course, Brandi had to try and ruin my princess fun, grumbling behind her pacifier gag, trying to resist as Connor picked her up like a doll. “No, no, no Little Ms. Priss,” I quickly shut her down. “It's a special day and you better behave or else you’ll end up over Daddy's knee!” I warned, wagging my finger in her face.

"Ew, he smells," Connor grunted, tightening his grip on his former bully. "She smells," I corrected him with a sassy wink. "And she smells because she refused to give Daddy a special 'good night kiss' last night So I didn’t change her!” I giggled. “Aww,” I cooed, “look at her, still struggling. Are you going to be a good girl now and earn your diapee change, Brandi, or do you want to spend another day in your messy Pampers?” I loved how after all this time, the poor sissy still thought she had a choice, an opinion, or any shred of dignity left. “Is diaper rash really worse than sucking Connor's dick for the millionth time?” I asked sweetly, booping her on the nose.

I quietly spun my finger in a circle while smiling at Brandi, gesturing for Connor to turn the helpless sissy around. "Bend over, girlie," I commanded in my mommy voice, pushing Brandi's head down. "Do you know what day it is, little one?" I asked, unzipping the back of her PJs and pulling them down to her ankles. She struggled as Connor pressed his hand against the small of her back, her head shaking in confusion. "Daddy?" I asked with a wink at Connor. "Can you help our sweet girl remember what happened a whole year ago today?"

"Wow, can you believe it's been a whole year?" Connor teased as he slowly removed Brandi's plastic panties. My bull, with his hand wrapped tightly around Brandi's braided ponytail, forced her head back to meet his gaze. "Since. I. Started. Fucking. Your. Girlfriend." With each word, he punctuated it with a firm spank on Brandi's diapered bottom. Poor Brandi was squirming and struggling even harder now, tears were even welling in her eyes! "Wow, Daddy spanks hard doesn’t he? Thank goodness I double diapered you!" I laughed, "otherwise, poor Brandi would be making a huge mess all over her crib!"

Connor couldn't get enough of spanking his pathetic little sissy cuckold, aiming right for her exposed thighs. That means it's been a year now since I made you my bitch! And all those years you thought you were better me? Now look at you! You fucking sissy!" Poor Brandi was crying and begging behind her gag with each smack, sobbing now. "Mmmmph! Mmmmph!"

Connor was getting rougher and rougher, reveling in her humiliation. "I can't understand you, loser!" He laughed, yanking her up by her hair again. I didn't want to tire her out before the real fun even started! "But to celebrate,” I intervened, rubbing Connor's strong back, calming him down, “Daddy and I have planned your Sissy First Birthday! We've even invited all our friends, some of your coworkers, and a few special guests! Oh, and of course, we decorated the backyard for your special party!"

“Let’s get her ready!” I laughed, tugging Brandi toward me by her hair. “I’ll change your diapee now and you can give Daddy that special kiss you owe him later when all your friends arrive!” I turned to Connor; “Babe, could you hold her down for me? She’s probably going to be a squirmy little sissy when she sees her special outfit…”

#humili sissi

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fetishfairytales2 · 12 days

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Daddy’s Girl

"Ugh, will you just stop squirming, loser?” I sighed, trying to hide my giggles. Poor Brandi looked ridiculous in his outfit. Look how far this loser had fallen. From my boyfriend to a sissy cuck in less than a year. “Now sweetie, Daddy will be home soon and I need to get you ready for him, okay?”

I finished styling his hair into pigtails and pulled on them gently. “You know what real men daddies like Connor need after a day at their high stress jobs? They need playtime with their sissies! And you're going to be Daddy's good girl tonight, aren't you, Brandi?"

“Aww, Brandi,” I laughed, not being able to stand how scared she looked anymore. “I can't even with how precious and innocent you look! You're just a trapped little sissy, huh?” I asked, stroking her cheek. "That cute little penis pacifier won't be the only thing going in your mouth tonight..." I snickered, inspecting the ropes holding Brandi to what I lovingly called her "Sucky Stool." She hated it, but it was another one of Connor's fun ideas.

Leave it to him to find new ways to humiliate Brandi. He built a sissy pink princess throne with Brandi's name, hearts, and flowers all over it. The seat was perfect, putting Brandi right at waist level for whoever's standing in front of her. It was also made of a nice firm wood, ensuring that everything in her diaper, or even *ahem* inside her, gets all nice and squished.

“Oh my god, your sweet little Daddy's Girl outfit is seriously the cutest thing ever, Brandi! We can't have anything messing it up while you're playing with Daddy, right? You know how upset I get when you make messies! Let's slap on a bib, okay?” I ask with a giggle.

I hold up the final new piece of Sissy’s wardrobe. “Brandi, check out this adorable little bib I found you! It’s your favorite color; pink! It’s even got cute hearts and look, it says ‘I <3 Cum!’ So you!” I put it around her neck, give my cucky a peck on the cheek, and seeing that panic in those eyes just warms my heart and my panties!

“I'm leaving you here as a cute little surprise for Daddy!” I laugh, making my way toward the door. “I already sent him a pic of you in your outfit, with a cute little message. ‘Your Sissy wants to help you unwind from work today, sir!’ If you're a good girl and really make Daddy feel special, maybe I'll think about changing your diaper at bedtime... maybe!” Sissy groaned as she watched my flip off the lights and shut the door behind me.

I love being a little brat to daddies 😈🧸

#humili sissi

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fetishfairytales2 · 12 days

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Besties 8 (Story)

This was originally written as a continuation of a story by @wittlesissyb4by called Besties. Check out all their fantastic stories on Tumblr and SubscribeStar.

—————

"Ain't happening, piglet!" I scoffed, as I pressed the vibrator against the super sensitive head of his pathetic clitty. His eyes shot back in his skull, groaning and wailing in a combination of ecstasy and torment, wrestling with the restraints as sweat dripped down his flushed face. "But don't stress, Brandi, darling, we're just revving up!"

Preparing to step up his torment, I dipped my hand back into the bedside secret stash. "Well, well, well..." I whispered, charging the air with delicious dread. "Seems Mommy likes it when Daddy plays dirty, huh?" I plucked out the bondage tape, holding it in one hand while maintaining the vibrator's relentless assault. I tore a couple of strips and got to work, wrapping them secure tightly around his twitching, helpless sissy twig and the relentless vibrator.

I took a hot minute to soak in the pathetic sight of him. He was twitching all over, that sissy dick bouncing up and down as if begging for attention. The sheer desperation in his whimpers was just golden. "Aw, what's the matter, Brandon?" I spit out, smirking at his sissy ass. "Lost control, huh? Ugh, such a weakling."

Back at it with the toy, pressing it against his stiff cock. "So, are you picturing Heather and Conner together now, huh?" I could see a look of dread and excitement in that sorry excuse for a man's eyes. "Unlike your sorry ass, Conner's showing Heather what a real fuck feels like!" His humiliation grew as I laughed at him. "That's why you're stuck here in diapers and he gets to fuck your girlfriend!"

I wagged my finger in his face, watching him moan deeper. “I swear, Brandi, if you dare to spill even a smidge of pre-cum, I'll fucking lose it on you." I put on my best bitchy face, smirking down at him. "You better behave if you ever want a chance to make ‘cummies’ again," I chuckled, mocking him with air quotes. "Got it, princess?"

As Brandi there squirmed like a worm on a hook, I made myself comfy on the bed, resting my head on his pathetic chest. While he moaned and groaned in his pleasure/pain bubble, I geared up for some reading. "Heather's message time, sissy boy," I reminded him, winking.

"Damn, Heathers been a busy bee," I couldn't help but gawk at the flood of texts on my screen. Poor Brandi choked on his gag, wishing he was in Conor’s shows. The level of details in the texts I’m sure pinched him a little more. Boy, I was having a ball.

“Let’s see what Mommy says,” I winked and cleared my throat, doing my best impression of Heather. “‘Connor just loves how I’m a little cum slut for him. And the kinky shit he enjoys, oh my God girl! Like when I swallow his dick all the way to his balls," I paused, hooking Brandi with a wicked grin. “Apparently they’re trying new things tooâ€¦” I stopped for a minute to build the anticipation in Brandi’s eyes "...anal. She says he drools over her tight ass, he just can’t get enough of it.” I tried to get as dirty as possible, wanting to tear apart Brandi’s heart and still swell his cock in it’s cage. “She wants you to know that while she would never, EVER, lower herself to let you fuck her ass, 'Daddy Conner can plow her backdoor anytime he pleases'!" I sniggered, empathy or pity miles away from my mind. Brandon's humiliation thrilled me no end as Heather's texts added fuel to the fire.

"Got it, Brandi? This is what your sweet innocent girlfriend does with real studs." I flaunted the phone in my hands, detailing the fun sissy Brandi was losing out on. "She says she loves to be on her knees, worshiping his massive cocks. Her lips explore every inch, she says she would even rim his ass if he wanted. She says he's the alpha male, that she loves when he puts her on her knees, grabs her by the hair, and forces her to deep throat his massive cock. It turns her on so much when such a strong man is making her plead for him to jizz all over her face and tits.”

There I was, staring down at Brandon’s gross, ugly, sissy face. He had a disgusting mix of enjoyment tangled up with a last ditch effort to hold on to his long-lost manhood. "Seriously Brandi,” I rolled my eyes. You really thought you ever deserved Heather? Pathetic." This just about did it. I could see him getting as rigid as might be possible, his hands clawing white-knuckled at the bedspread. Poor sissy bitch was going to cum hearing about his girlfriend fucking another guy!

"Aww, relax, Brandi," I added in the very same sweet voice, holding his gaze like he was on a leash. "Guess what? Your sexy ass girlfriend has gotten lucky. She’s on to bigger and better things! Now she’s Conner's fucktoy.” I laughed; No shit sissy, how great is that? A serious improvement from the nightmare of your worthless ass humping on top of her for 30 seconds before spooging your sissy goo on her belly. She gets off every single time with him, can you believe that? Heather told me that you had never given her a single orgasm.” I leaned in, licking a tear from his cheek, loving how destroyed he looked. “She had nothing but lousy, fake moans for you every single time! You can't hold a candle to a real man like Conner, can you?" My lips curled in a wild smirk, and I could sense his orgasm coming quickly. "Heather owns you, but guess what? Conner fucking owns her. Guess that means you’re both his bitches!”

God, the loser was quaking like a leaf and his pitiful excuse for a dick was throbbing pathetically. "Got a problem, sissy Brandi?" I teased. The poor thing nearly creamed his Pampers hearing about how Heather had turned him into a cuck. I pressed up against him, my chest smothering his face while my hand held that buzzing toy against his sad little sissy clit.

He was like a puppet on my string, his body jerked on the brink of the sissygasm. The loser's eyes were bugging out of his skull - a hilarious sight as he suffered. "Come on, what’s the issue sissy?" I taunted, close enough to feel his pathetic panting against my skin. My own arousal was spiking as I got more wicked by the second. Licking his ear, my other hand sneaked into my panties, feeling extra naughty. Humiliating Brandon was pure ecstasy, sending thrilling shivers straight down to my swollen clit. I wanted to overpower him completely, make him crumble entirely.

“Mmm,” I moaned as I played with my clit, taking my hand out of my panties, my fingers slick with my own arasal. I ran my wet fingers over Brandon’s face and through his hair. “That’s it Sissy!” I cooed. "Cum for me, Brandi-Baby, let it all go," My voice was sugar sweet as I coaxed it out of him. Hah! As if that pathetic fool could ever cum like a real man. He was so close to losing it, his pleasure-painted face teetering on the edge of orgasm. "Show me what a tough guy you are, cum for your sweet cuckysitter!” I taunted, the thought of him caving to my demands making me even hotter. Turns out, there's nothing quite as amazing as taking a cocky jerk and grinding him down into a subservient, simping, and squirming sissy

"Ugh, Brandon, you pathetic loser!" I sneered down at him, watching his spunk settle in his nappy - still trickling out from his puny pecker. "Really, Brandi? Getting your sick kicks from hearing stories about your gal getting down with a real man?" I hopped off his chest, plonking myself beside the shrunken sissy. I dipped a finger in his loser puddle, taunting him with the evidence. "Aw, look! You're just a sick, messed up little cucky, aren't ya, girlie?" My sadistic grin was unshakeable as I saw the panic flash of humiliation across his face. "Ahh, sweetie, you're going to have to be punished now," I chuckled, his dread washing over his face. "Should've listened to Ms. Lyndsey when she told you not to spunk everywhere, ya helpless slut!"

#humili sissi

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fetishfairytales2 · 17 days

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Brandi’s Just Horsing Around (Heather)

Concept originally borrowed from a long-lost story that used to be a favorite of mine.

———————————————

“Brandi, listen up! Mommy's got a new toy just for you! Daddy Connor has been soooo creative lately, just to help me torment our adorable little sissy, and he's outdone himself this time! He made you this super cute rocking horse, isn’t that sweet? It’s all sissy pink – totally your color! But, girlie, the real surprise? There’s no saddle, just a long groove down the middle. Hmm, I wonder what could fit there?

Don’t get too bouncy yet, sissy, there's more! See these fierce black leather boots? They attach right to the side of the horsey to keep you stuck on it – but that’s not all. These booties are deep enough to hold you when you're all folded up trying to straddle it. Yup, it's designed to keep those sissy legs of yours spread super wide.

And OMG, this adorable little rubber mask with pigtails! It's the cutest, and guess what? It comes with a built-in gag to keep you oh-so-quiet. No more whining or begging, sissy. You’re going to be all smiles, permanently! On the outside at least!

Mommy has also prepared the cutest little riding get-up for you! You’ve got this totally adorbs white frilly baby doll dress with a flared skirt just perfect for letting your sissy bottom peek out. But, babe, those arms on your dress? They are, like, no ordinary sleeves! They're super stiff and stick out all funny because, this actually wraps around your chest backwards! Look, there’s internal sleeves! Aren’t you so excited? You’ll be locked in the cutest little sissy straitjacket ever!

And those doll-like hands on the sleeves? They’re not totally useless, unlike you! Once we zip up the back of your dress nice and tight, those hands get clipped onto the handles next to the horsey's head.

From the outside, you’ll look like just the happiest little sissy cowgirl enjoying her new toy!

Of course, there’s this amazing pink 8” ribbed dildo I’ve got for you. It will slide right here into the groove, just waiting for you on your horsey's saddle. But, cause I’m not, like, the meanest Mommy ever, I’ll just let you hover that helpless sissy booty right above it. I know it can be scary seeing such a big cock for the first time!

But Brandi, you better clench those sissy thighs tight or you might just gobble up that entire thing with your sissy pussy! You're gonna be so exhausted trying to ride your little horsey without slipping! If you slack and lean back, who knows where it’ll end up! And here's the best part, sissy— I asked Daddy to rig the saddle with springs! Every rock back and forth is going to slide that dildo deeper, fucking you like the little sissy slut you are!”

#humili sissi

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fetishfairytales2 · 30 days

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Always Here for You (Kylie)

Oh, look at you, trapped in your little sissy cage while your girlfriend is having the time of her life. Can you hear her moaning? Of course you can sissy! She sounds like a porn star! This has got to be the first time you’ve heard that before. I know she’s never moaned that loud with a loser like you - not even when she was faking it! That's what it sounds like when a real man takes care of a woman. Not like the pathetic whimpers you make when you prematurely ooze your loser goo.

Aww, are you a sad sissy? Why baby girl? You know you would never be able to satisfy her like he can. You're just a little sissy cuck, meant to be locked away and forgotten while she enjoys a real dick. Don't worry though you sweet little Pampered Princess! Your Mommy might have left you behind but Cuckysitter Kylie will always be here for you! I'll make sure to tease you, and spank you, and to remind you of how much of a worthless sissy you are every chance I get! Then I’ll put you down in your cage and turn up your baby monitor so you can fall asleep to the sound of your Mommy being ravished by your new Daddy! Aren’t I thoughtful?

Eww Brandi, is that your diaper I smell? Ugh, you’re so gross! You always cry ‘No! No! I’m a man, not a little girl!” But, here you are, wearing a dirty diaper like a little baby. And you know what's even more humiliating? That you’re going to be sitting in it for quite a while! That’s right sissy! I won't change it until Mommy and Daddy are done. I think it’s only fair. You used to make her suffer through your pathetic attempts at being a real man, now you should suffer through her getting the sex she deserves!

Uh-oh sissy! Did you hear what Mommy just said? She asked Daddy to save all the used condoms. What do you think she’s going to do with those, Brandi? And what does she mean “I think next time Sissy should get it from the source?” I bet that’s not good Brandi…for you at least!

#humili sissi

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fetishfairytales2 · 1 month

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You’ll Just Have to Deal (Heather)

“Aw, is the little sissy grumpy because she needs a change? Don't worry, Mommy has got you covered.” Heather laughed and held up the crinkly pull-up. “You’ll just have to deal, Princess! When Daddy leaves in a day or two, we’ll get you some new Pampers. No need to pout, Brandi. I know it’s not fair, Mommy promised, I know, life’s not always fair is it, sissy? Daddy Connor convinced me that he and I needed alone time, and you know I can't say no to him. That’s why Mommy needs to get you into a new diapee before she leaves you in your crib for the next few hours, Daddy and Mommy are going to have so play time! Don’t worry, you’ll be able to hear all of it on the monitor!”

“Don't worry, Brandi, I saved your pissy Pamper just for you.” She smirked and placed the used diaper down on the changing pad. “And before I put you back in it, let's get you all powdered up. We wouldn't want you getting a rash, now would we? Too bad I ran out of baby powder too…” Mommy Heather left the nursery and came back with an evil smile and a clear plastic bag of white powder. “But don't fret my poor sissy, I found this Ground Rose Hip stuff online. Sounds so cute and innocent, doesn’t it Brandi? I think it's actually itching powder though. Oh well, let's just spread it all over your little bottom and clitty cage and see what happens, hmm?”

#humili sissi

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fetishfairytales2 · 1 month

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Besties 7

This was originally written as a continuation of a story by @wittlesissyb4by called Besties. Check out all their fantastic stories on Tumblr and SubscribeStar.

—————

“I am going to have a blast destroying you in every way imaginable - mentally, physically, and emotionally. I'm going to break you…" I couldn't even finish that sentence before Brandon ran for the door. This was getting too entertaining. I stuck my head out the door and saw Brandon stumbling down the hallway. "Cruciex,"I sang out with a wicked grin.

I cracked up as Brandon froze and spun towards the corner of the hallway. He just stood there, like a statue, while I sauntered over. Giggling, I brushed my fingers against his face and purred in his ear, "You're just too much fun to fuck with. Give in, you precious little sissy, save yourself the struggle.”

I gripped Brandi's ear tightly and yanked him back into the bedroom. His eyes couldn't even meet mine as I berated him, "Do as I say, you stupid little sissy. Your diaper-clad ass belongs to me!" I couldn't resist squeezing harder, causing him to wince in pain as I dragged him to the bed.

"Go lay on the bed, Brandi." I laughed, shoving him onto the mattress and easily restrained his left wrist. Smugly, I taunted the tied up loser; "aww, such a helpless, weak little diapered baby. Can't even stop a girl from beating you up!" I used the handcuffs to secure his right wrist next. "Tsk, tsk," I shook my head; "you should have behaved like a good little girl…"

I pulled Brandi into a seated position by on the bed by his hair. "Make yourself comfortable, loser. This is going to be a long night," I taunted as I settled in next to him, resting my head on his chest. Grabbing my phone, I saw three messages from Heather.

"Hmm, let's see…" I said, scrolling through the texts on my phone. I playfully ruffled his hair and continued, "Looks like Mommy is having a great time with Daddy Connor. She's sharing all the juicy details with me. But don't worry, I'll save them for story time later." I sat up and laughed at one text in particular. "Make sure Brandi is punished severely if she cums.

Brandon side-eyed me nervously from behind his pacifier gag, clearly clueless as to why I was cracking up. "Relax, sissy," I sneered as I loomed over his powerless frame. "You'll figure it out soon enough! Heather specifically asked me to tell you that she and Daddy Conner love you." I could see the bewilderment in his gaze; "my bad," I chuckled while rechecking the message. "They love tormenting you. Whoops, guess that's a little different…"

I whispered gently into Brandi’s ear as I peered down at the helpless and terrified loser. "Listen up, sissy. Keep those eyes locked on Ms. Lyndsey and all my beauty. Don’t let your mind wander. I want you fully focused on your gorgeous cuckysitter…" With a flirty wink, I bent down and placed the lingerie and vibrator on his lap. "Would you mind holding these for me, sweetie?" I asked with a mischievous tone.

My hands glided down my chest as I gave Brandon a sexy gaze, raising one eyebrow and letting out a quiet sigh. God I was going to tease him until those blue balls exploded! "You know what, maybe I need to change my outfit. What do you say, Brandi?" I began unbuttoning my jeans, slowly sliding them down and swaying my hips. I paused as I hooked my thumbs into the hem of my shirt.

I locked eyes with Brandon and slowly started to lift my shirt. "Normally, I wouldn't feel comfortable stripping for a man," I quipped, tossing my shirt aside. "But you're not a man, are you? You're a pathetic little sissy." I flirtatiously twirled the shirt around my finger as I advanced towards him, still staring him deep in the eyes. "A silly little sissy with a locked up clit," I chuckled, letting the shirt fall to the ground.

Brandon squirmed in his cage, his desperate eyes couldn't seem to look away from the sight of me slowly undressing. "Aw, does Baby Brandi want to make cummies?" I teased, laughing at his obvious arousal. I slipped out of my jeans, revealing my black thong and giving him a good look at my ass. Spinning around, I could practically feel Brandon's poor clitty throbbing in its cage. "Does your little dick hurt, Baby Brandi? It must be so tough being denied your sissy squirties," I said, relishing in his humiliation.

I casually slipped off my bra and let it fall to the floor, making sure to keep one arm across my chest, just to deny him even that for the moment. Brandon's eyes bulged as he watched me, and I couldn't resist teasing him a bit more. "Oh baby, this is just the beginning. You just go ahead enjoy it…while you can," I taunted, strutting over to him and grinding my tits against his face. "Don't worry, there's plenty more where this came from," I whispered seductively in his ear as I turned around and showed off my ass. Slowly, I teased him as I slid my thong down, slipping it down my legs. “Aren’t they pretty?” I asked sweetly, holding up the black thong in front of Brandon. He nodded, unsure of what was happening now.

"Got a present for ya, loser!" I purred, holding it closer his face with a smirk. "Just breathe it in, babe," I cooed making sure to slide the panties over his nose and face, enjoying the way he shuddered at the scent of me. "Not used to being so close to pussy anymore, are ya?" I teased, my body pressed against his as I circled around him. "Now, are you ready for what's next, sweetie? I can't wait to see you squirm."

I began swaying my hips as I straddled his lap now. My fingers traced along his inner thighs, causing him to moan in frustration. Pressing my body against his, I could feel him trembling underneath me. "You're enjoying this, ain't ya?" I teased, pulling away once again. His gaze never left mine. "You're just a helpless sissy, even with your little dick locked up you still crave me, huh? It must be so frustrating!"

I strutted around, my hands playfully pressed against his chest as I got closer and closer. “It must be so hard for you sissy. It’s probably been months since Mommy drained those little sissy balls…” Each little sway of my hips elicited a muffled moan from his stuffed mouth. The way his cheeks turned pink and his eyes widened only made me want to push him further. “Poor Baby Brandi is never going to cum again, is he?” I leaned in and placed my lips against his neck, feeling his skin run hot as I kissed and licked him.

"Looks like it's time for the main event," I purred, stepping back and picking up the lingerie strewn on the floor. I stood over his body, looking down at him with a smile. "You must have loved watching me undress earlier, little sissy. But I have a feeling you'll enjoy seeing me get dressed even more!"

Turning around, I shot a flirty look over my shoulder and gave my back a nice arch, showing off my ass. I could practically feel his eyes on me as I reached down and grabbed hold of my delicate, black g-string. With a cute little sway of my hips, I leisurely pulled it up my legs, feeling the soft fabric against my skin. "Mmm," I moaned; "imagine being the lucky guy that gets to take this off of me…"

I was feeling myself in that moment, I looked killer. I stood up tall giving him the full view of my naked bod. Poor sissy was mesmerized. I purred, "looks like you're getting the VIP view, huh?" I couldn't resist throwing a little wink and booty shake; "wait til I turn around… I said, spinning to face him, finally showing him my tits up close.

“Aw, what's wrong, Brandi?” I teased, batting my eyelashes innocently as I ran my fingers over the silky fabric. I could practically feel Brandon drooling over me, but we all know he's locked up tight in that little pink cage. I held up the sexy black bra and smirked down at him, hand on my hip. "I mean, I get it, I'm hot," I joked, "but you can't ogle me like that!" I playfully smacked his crotch, "I better get dressed and out of your reach, you horny little sissy. You don't want to get in trouble, right?" I slipped on the bra and pouted; “aww, poor sissy couldn’t control himself and now he doesn’t get to see any more boobs. How sad for you!”

I got down on my knees, straddling Brandi. His eyes were filled with fear as he looked up at me, trembling ever so slightly. In a low voice, I asked him, "It's been a hot minute since you've been this close to a cute girl, huh?" I gave him a wink and a smirk. "You better pray I don't spill the beans to my man about this. He might be the next one to teach you a lesson!" I couldn't help but giggle as I slowly licked along his earlobe and he whimpered.

"Remember, Brandi, when I shared with you how I used to drive my college boyfriend crazy? Eventually, he stopped letting me tie him up! I pouted and snuggled closer to my sissy, resting my head on his shoulder. I whispered in his ear, my breath teasing him. I moved my thong away from his nose and took out his paci, sliding my tongue around his lips making him moan louder. "No, no," I laughed as he tried to beg. “I don’t want to hear a word…” I quickly shoved the penis gag back into his mouth and secured it with my panties.

"Ugh, he said I was too mean," I said, crossing my arms and mimicking a temper tantrum. "I would tease him for hours, but then of course, I would let his poor pent up cock explode inside me," I began, running my nails teasingly along Brandon's thigh, as he hung onto every word of my story. "But then he had to go and get all sensitive on me, just because I ignored his safe word for a few hours, like three or four times. What a buzzkill!" I exclaimed, looking down at the helpless, bound and gagged sissy with excitement. "But you, my little doll, won't give me that kind of attitude, will you? You're all mine to play with however I want. Even if sometimes I play with my toys a little rough, right? I mean, they are my toys! I'm the one who gets to break them."

Trailing my fingertips along the edges of Brandon's skirt, I made my way to his thighs and the crotch of his diaper. "Poor little Brandi, is your diaper all wet?" I teased, faking sympathy. I lightly explored the outside of his diaper before brushing my fingers against the head of his chastity cage. As my hands continued their journey up his legs, goosebumps formed in their path.

"Do you need a diaper change already?" I teased, watching as his breath quickened with anticipation. I slipped my fingers under the waistband of his diaper and undid the tapes on each side, leaving the diaper still under him. I couldn't resist chuckling at the sight of his little pink micro chastity cage. "Aww, look at your poor caged clitty," I grinned, flicking it lightly. “How pathetic.”

I retrieved the small key from the chain around my neck. I just couldn't resist playing with Brandon. "Hmmm, should I use this cute little key and release you from your cage?" I tease, holding the key in front of his eyes. His anticipation was obvious, and I couldn't help but laugh and dangle the key just out of reach. "But only if you behave, Brandi dear. Can you do that for your evil, yet oh-so-lovable Ms. Lyndsey? I promise it will be worth it."

I reached forward, gently stroking the front of Brandon's face with the key. "Poor sissy sweetie, you don't have a say in the matter, do you?" I cooed. "All I want you to think about is the incredible feeling of the real orgasm you’ll never have again and how badly you want it. No matter how mean I may be, and no matter how much I torment you, just focus on those sissy squirties, got it?"

Deliberately, I unlocked the chastity cage, twisting the key in the tiny padlock toying with Brandon's emotions. I could feel his hips thrusting in the air as he squirmed in his spot. I couldn't resist dragging out the moment, enjoying every second of it. I was living to ruin him. I wanted his mind to melt before the end of the night.

Finally, I unlocked the cage and slid it off, exposing his tiny, shrunken dick. "Oh my god, it's so small!" I giggled, playfully tracing my index finger around the tip. I could feel him squirming with excitement, his arousal was pouring from him. It was time to push just a little more.

“Okay, you little sissy, it's time for your punishment," I purred into his ear. "Close those pretty little eyes and don't you dare open them," I commanded, keeping my finger lightly pressed around his clitty. With a devilish grin, I reached for the wand vibrator I had placed on the bed earlier, flipping it on and feeling the strong vibration travel up my arm. Brandon couldn't help but squirm at the sensation, trying to escape my grasp. But I was ready and grabbed the base of his cock, holding it firmly in place.

I delicately trailed the vibrator along the underside of his shaft, feeling his muscles tense and relax at the sensation. His eyes were filled with desire as he watched me, silently begging for me to stop. I could hear the muffled whimpers behind his gag and see the drops of sweat forming on his forehead as he writhed and squirmed against his restraints. "Oh no, silly sissy," I chuckled, responding to his wordless pleas. "This isn't for your pleasure, it's a punishment. You've been begging to be let out of your cage for so long, and now you're getting exactly what you wanted. Don't even think about cumming though, sissy! Not yet…"

I put the wand right against the tip of his cock, giggling as he writhed under me, feeling every vibration pulsing through him. His muffled screams through the gag only made it more amusing. "Oh honey, did you really think we were gonna take things slow?" I taunted, switching the vibrator to its highest setting. His body contorted and he struggled even more as I traced the toy along his shaft. I could feel his resistance in his tense shoulders, but I just laughed and enjoyed his suffering.

#humili sissi

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fetishfairytales2 · 1 month

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Besties 6 (Story)

This was originally written as a continuation of a story by @wittlesissyb4by called Besties. Check out all their fantastic stories on Tumblr and SubscribeStar.

—————

Besties 6: Alone with Ms. Lyndsey

“Heather, seriously?” I laughed; “is Connor really cool with all of this? Cause I know he’s not, y’know…” Heather laughed in response, walking out of the nursery, back to her bedroom. "No, he’s too much of a real man to give a shit about that," she snickered, pointing to Brandon, "Brandi just has a tight little ass that could milk a big dick and Connor likes to fuck it occasionally!"

Heather went back into the bathroom to wrap things up, leaving me alone with Brandi. "Connor gets it," she called out. "Sometimes I just want him to tear into Brandi’s ass because I get off on seeing it." There was a moment of silence. "Other times, Daddy Connor just wants to show her who the real man is in this household."

"Does Brandi like it?" I couldn't help but ask even though I already knew the answer. Heather emerged from the bathroom, rocking a killer outfit with her tight trench coat and those red heels, looking like a total babe. She had the biggest grin on her face. "The real question is," she giggled, "does she even have a choice? Now, Brandi, I'm heading out. You better behave for Ms. Lyndsey, be a good girl. Don't forget, if I hear any complaints, Daddy will find out!"

She turned and gave me a wicked grin. "He'll be getting punished either way, good girl or not. But if she acts up, let me know. I'll send you all the deets and instructions. Don’t forget, her dinner's in the fridge. Oh and do me a solid, share all the pics and vids I send you tonight with Brandi. She loves seeing Mommy's naughty side during my date nights!" She hugged me and lightly tapped Brandi's butt before strutting out of the room with a smirk.

I couldn't help but smirk as I saw Brandon, the man who was once so full of himself, reduced to nothing but a pathetic little sissy in a frilly dress and diaper, forced to face the consequences of his asshole behavior. I loved that my best friend had made it all happen. She took away his power, his pleasure, his whole life. I bet she wasn't done yet either. "Oh, look how far Brandi has fallen," I taunted as I grabbed his hair and pulled his head up to meet my gaze. "But don't worry, we can make you sink even further."

"You, like, have noooo idea how much shit I'm about to put you through, baby bitch," I cackled, eyeing Sissy Brandi's pathetic little frame. I pivoted, checking myself out in the mirror. This situation called for a whole different vibe. I came dressed down to Heather's place, but now it's time to bring out the big guns. I rummaged through her drawers until I found the perfect thing: a sexy black lingerie set.

Turning to Brandi, I couldn't resist poking fun at his sorry excuse for masculinity. "Heather and I have been swapping clothes and men since college," I said with a sly smile, knowing how much that would hurt his fragile ego. "All of them way better than you, of course." I held up the lingerie set and let him squirm in embarrassment. "But hey, some things never change, right?" I could practically hear him whimpering under that gag, clueless to what was happening behind him. Tossing the lingerie onto the bed, I couldn't wait to see his reaction.

I ran my perfectly manicured nails through Brandi's hair, feeling him tremble as I whispered, "Relax sweetheart, we have all night to play. No need to get too worked up just yet." A sharp slap on his ass made him squirm with anticipation as I continued my search, this time in the nightstand.

I pretended to be all innocent, asking with a sly smirk on my face, "Hm, I wonder if your mommy has any fun toys hiding in here?" I couldn't help but laugh as I found the handcuffs and the Hitachi wand, more evidence of Heather's kinky side. I turned again to Brandon with a smug look, ready to ruin his night.

"Anti-crucio!" I yelled, watching as Brandi immediately spun around to face me. My grin couldn't get any bigger as I twirled the handcuffs on my finger. "You have 12 seconds of freedom, just to hear how screwed you are, Brandi," I gloated, poking my finger into his chest.

#humili sissi

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fetishfairytales2 · 2 months

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Ask Princess (Heather)

Hey all you perverted ladies and losers! Looks like you're all enjoying seeing me put little Sissy Brandi in her place. The requests for more are piling up faster than I can humiliate the poor thing. So with all this attention, it’s time for another round of questions for yours truly. It’s time to Ask Princess Heather!

Today's question comes from Jessica, a fierce and bad ass babe who finally wants her sissy to meet the man that rocks her world. Jessica asks;

"Princess Heather, my boyfriend is such a hot stud who knows how to please me in bed. But I can't help but fantasize about him dominating my pathetic husband. I've already got the loser in diapers, but he needs a strong Daddy to really put him in his place. How can I bring up the idea to my man without scaring him off?"

Babes, don't waste your time worrying about just good dick. What you really need is a man who can understand and cater to your needs. Connor knows that and that's why I allow him to use me as he pleases, as long as he continues to torment the person he despises the most. I mean, let's be real, who wouldn't want to have their cock sucked on demand? But sometimes life gets busy and I'm not always available. That's where our little sissy comes in handy.

Connor and Brandi have been in each other's lives for years, and let's just say Brandi has always been quite the troublemaker. But what can I say, Connor loves spending "quality time" with our sissy. He gets a thrill out of punishing and dominating her. In fact, he's even gotten creative with it, building all sorts of toys and furniture for her, like a crib, changing table, and even a special rocking horse. You guys have got to remind me to tell you that story later

Girl, let me tell you, it's a sight to see when my alpha boyfriend grabs Brandi by the neck, throws her over his lap, and spanks her with his big strong hands. Connor would probably tell you it makes him feel even more like a man to take control of such a loser.

As if Brandi doesn't already feel like enough of a loser being spanked by my lover while she cries and begs Daddy to stop, she has to beg to suck his dick just to make him stop. It's like Connor gets off on humiliating her and using her as foreplay before he fucks me. Sissies like Brandi are just there to be our little playthings, fluffing your man and getting him ready for you. The hottest thing I ever told Connor was that I owned Brandi but Connor owned us both. He fucked me so good that night I gave him the key to Sissy’s chastity cage just to prove that she was our toy now.

Listen up, ladies. If you've got a sissy who can give you a foot rub and then get your orgasam on with your real man, you're living the dream. But be honest with your boyfriend because, sometimes, you just need your sissy to get facefucked while you watch.

#humili sissi

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fetishfairytales2 · 2 months

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Besties 5 (Story)

This was originally written as a continuation of a story by @wittlesissyb4by called Besties. Check out all their fantastic stories on Tumblr and SubscribeStar.

————— Besties 5: Nursery Naughtiness

God, Brandon was being such a little bitch, dragging his sissy self into his former bedroom with tears in his eyes. Honestly, this just proves how clueless men are. He knows we're going to do whatever we wanted to him and he'd still try to resist. What a dumb ass. But my irritation melted away as Heather strutted out of the closet, looking hot as hell. She was wearing nothing but a smile and some red heels!

"So, what do ya think?" Heather asked, flashing a wicked smile. Damn, she was killing it! Heather was practically glowing. Her tits were on point, and her waist? Like, whoa, so tiny and smokin'. She did a little spin to show off her tight little ass and playfully stuck her tongue out. "Mhmm, check you out!" I playfully joked.

Even Brandon couldn't resist taking a peek Heather, and that's saying something considering his itty bitty caged clitty! His face was a mix of humiliation and pain, and I couldn't hold back my laughter at his torture. Heather and I exchanged a knowing smirk, loving her complete control over him. "Oh, it looks like daddy's in for an goid night," I taunted, playfully messing up Brandon's hair. "Does someone else like what they see too, Sissy?"

Oh my god, Connor is going to be drooling when he sees you, Heather!" I playfully nudged her and let out a squeal. She was staring at her suffering sissy and I could see the pure joy in Heather's eyes as she started to mess with him again. "Don't worry, babe," she said with a smirk, strutting towards him. She took his face in her hands and stared into his eyes. "I'm sure Ms. Lyndsey will keep you entertained while I'm gone..." She taunted with a slow, seductive grin, before finally releasing him.

"Aww, is the little sissy baby blushing? How pathetic!" I couldn't help but laugh at Brandi’s embarrassment. "And don't think I'm gonna show off my goodies to just anyone," Heather added, disappearing in her closet. She sashayed out a few seconds later, wearing a tiny black trench coat that barely covered her butt. "So don’t be jealous sweetie!” She giggled, blowing Brandon a kiss. “Only Connor whenever he wants and you when I let you"

While Heather pranced off to fix her makeup, she suddenly perked up. "OMG!" she squealed. "Cruciex!" Just like that, Brandon became stiff as a board and started walking towards us. "What's that one do?" I asked, watching the little sissy make his way across the room. "Oh, it's like, totally genius. It puts him into corner time! He has to stand in the nearest corner with his nose against the wall and keep his mouth shut, no matter what's happening.” All I could do was just stare in amazement at him, all tucked away in the corner like a good little sissy. “This is SO awesome!”

Sorry, I don't have time to give you all our little loser's sissy trigger words and show you around the house," Heather sighed with a disappointed look at her phone's clock. "But don't worry, Brandi will be excited to show you her playroom! If she isn't, we can make her excited about it'" she chuckled, "Oh, and I'll text you the whole list of words to use. And let me tell you, there are so many toys in his nursery. Daddy Connor helped build both the nursery and the playroom, by the way, for our lucky sissy!"

I couldn't help but laugh, while Heather slapped her forehead in that overdramatic way she does. "Duh!" she exclaimed. She started to unclasp the key to Brandi's chastity cage from her neck and handed it to me. "Here, you take this. I have more than enough dick to handle tonight!" Heather couldn't contain her laughter as she adjusted the key, making sure it was nestled between my boobs. "I love wearing it like this, it's a constant reminder to her of what she can see but not touch!"

"Come on," Heather gestured towards the door. "She won't get into any trouble, Brandi's practically a doll at this point!" We walked down the hallway to what I remembered as the guest bedroom door, but now it was painted a soft pink with white accents. I had to smile when I saw the foam letters on the door that spelled out "Sissy's Nursery." Heather just shrugged. "The only people who come over are either people I want to hook up with, people who are here to help me humiliate Princess Pampers, or both!" Always one for dramatic flair, Heather paused for suspense. "Ready?", she swung open the door. "Ta-da!"

My jaw dropped. "Oh my gosh, girl! This is insane!" The nursery walls were painted a soft pink with white accents, and a plush white rug covered the floor. In the corner sat a big toy chest, painted to match the rest of the room, with "Sissy's Toy Box" written on the front. Heather grinned and patted it. "Connor custom-made this for our little sissy 'daughter'," she said, winking at me. "It only took a blowjob from Brandi!" The toy box was packed with all sorts of sissy playthings, including butt plugs, vibrators, rope, and handcuffs! "Oh my gosh, Brandi is so lucky! I didn't get my first vibrator until I was 16! He must have, like, five different dildos!" I cackled, nodding towards the toy chest.

Heather shrugged with a smile, "She have a total of 10, and none of them are under 6 inches for my little slut." As she searched through the toy box, I couldn't help but stare at her backside peeking out from under her coat. Conner was definitely a lucky man. "She's even given each of them a name," she called out, still rummaging. "There's Pinkie, Mr. Biggs, and Mr. Peter, who you've already met..." Then, she popped back up with three massive dildos in her hands. Two were different skin tones and easily over 9 inches in size. "And these two," she stifled a giggle, "are Mr. John and Mr. Jason!"

With a flourish, she presented the third - a black dildo covered with plastic studs. "This is Mr. Charles," she announced, unable to contain her laughter. It was clear that she had just a little too much wine. I caught on quickly and joined in her laughter. "Wait a minute... aren't John and Jason your exes?" Heather confirmed my suspicions with a nod, barely able to keep it together now. "Yes, girl! Every time I get my bitch boy a new toy," she gestured towards the box of sex toys, "I make him name it after one of my past lovers! He has to look at their dick pics, rate their cocks, and tell me which of my ex-boyfriends he would want to fuck him! Then he had to moan their name every time he fucks himself with ‘their cock’!"

This was seriously the best day of my life. I couldn't stop laughing. Finally, this douche of a human was getting what was coming to him and my bestie had embraced her inner mean girl to dish out some much-needed punishment. "But who's Charles?" I inquired, nodding towards the black toy. "Ah, yes!" Heather giggled. "He's Brandi's hot boss. I've been threatening her that I'll sleep with him…again."

Heather flipped a switch on the dildo's base, causing it to vibrate and rotate. "See, that's why I chose this one. Studded and vibrating - messes with the sissy’s head and poor butthole!" I laughed as I watched the toy shake in Heather's hand. "I even make her practice deepthroating it while she moans Charles' name. Just for added fun, sometimes I'll send her off to work with it up her butt," she turned off the toy and proudly held it out for me to examine. "It's hilarious to think that the man whose name she was just moaning is bossing her around all day at the office!"

Heather put away the toys and strolled over to the center of the room where a massive crib sat. Brandon's crib was all pink and white, matching the rest of the room. But it was made out of sturdy wood and had a heavy metal gate on top that looked like it could be locked! "Connor made this one too," Heather said, pointing to the crib. "It's gotta lock to make sure we're not interrupted by a whiny sissy during our playtime!" She winked at me and demonstrated how to latch the metal lid over the top. "Connor insisted on it after Brandi barged into our room one night during 'adult time'. Let's just say he got a good spanking from an annoyed daddy and couldn't sit for a week. After that, Connor built this to keep her temper tantrums under control."

Wow, there was even a pink padlock to sissy in her crib! "Wow, boo, this is so wicked!" I lifted the hinged lid and took a peek. "Holy crap!" Inside were two pink and white pillows in the shape of cocks, stitched with the words 'Sissy Cuck' in sparkly gold! "Gift from my sister to constantly remind Brandi of her place" Heather explained. Next to them was a matching blanket, also embroidered; 'Sissy Cum Slut' in glittery letters. "Also a gift from my sis when I told her about Brandi's new lifestyle," Heather laughed as I picked it up. "Aaanddd...", Heather said with a grin, "just to mess with her a little more, Conner made the bed a tad too small. Brandi can never fully relax in her cute little bed."

I couldn't help but notice how tight and uncomfortable it was in there, and it would only get worse when it's completely shut. "Poor Princess must suffer so much when I lock her up in here with his dirty diapers, and Connor and I get too caught up to let him out. And it's usually for hours at a time! Oops, our bad!"

I was totally obsessed with the crib and didn't even notice when I accidentally knocked the baby monitor off the nightstand. "Whoops, my bad..." I said, glancing down at the monitor. "Wait, isn't this supposed to be on the other end?" I asked, showing it to Heather. "Oh, you wait, girl," she laughed, taking the monitor from me to check to turn it on before handing it back. "Just give me a minute..."

Heather skipped out of the room and I could hear her voice coming through the baby monitor. "Anti-Cruciex... Princess, you gonna tell Mommy why there's a baby monitor in your room. It's not there for Mommy to hear from her sissy, right?" A long pause followed, probably while Brandon's face turned bright red with embarrassment. "N...no..." he stammered. "Then why's it there, silly Brandi? What exactly is Mommy monitoring?" Heather asked, pretending to be clueless. "M...mommy and daddy..." Brandon whined. "Mommy and Daddy, what, Princess?" Heather pressed, knowing the answer already. "What have you been hearing from your room about what Mommy and Daddy are doing? Use your big girl words," she commanded with a smile in her voice.

Brandon barely managed to mumble the word "f...fucking." before Heather cut him off. "Good girl, Cruciex," she ordered. "Back in the corner, Princess Piss Panties. Chop chop." Oh this was fucking perfect. I couldn't think of anyone more deserving of this humiliation than Brandon. Moments later, Heather returned to the room, winking at me. "Do you get it now?" she asked, giggling. "You make him listen to you having sex?" I sputtered, still shocked. "That's brutal, girl!"

Heather and I kept exploring the nursery. I couldn't help but notice the huge changing table with straps on all four corners. "Brandi can be a bit squirmish when it's time for a diaper change," Heather mentioned, casually gliding her fingers along the pink leather straps. "And when Connor's feeling extra playful, he likes to turn the changing table towards the crib, strap Brandi down, and make him watch us hook up over the side of the crib!" There was a second diaper pail conveniently attached to the changing table, labeled "extra soiled diapers." Gross.

Heather seemed to know exactly what I was thinking and let out a wicked laugh, saying, "That'e a special kind of punishment for when Brandi is a naughty sissy!" My eyes widened as she explained - she really was all into this. "You know, there are other places besides sissy behinds that a dirty diaper can be taped onto, y'know? Sometimes Brandi needs to 'face' her new life in diapers!" Heather chuckled. “Do you just…” I started to ask, he really did piss her off big time, huh?

“No,” Heather shook her head. “It definitely gets better…or worse I guess if you ask Brandi. Sometimes, when she's been really naughty, I like to take things up a notch. Instead of just making her wear the dirty diaper, I like to feed her the mess." Heather smiled, clearly enjoying explaining herself, proud of how far she’s pushed her loser ex. "Sometimes in life, I guess Brandi just has to eat shit and like it, y’know?” I was doubled over laughing now. I wasn’t sure I would make it through tonight. This was incredible!

As we walked through the tour, something caught my eye that I hadn't noticed before. Oh boy, was I taken aback! I expected all the art to be cutesy, babyish, and sweet. But what I saw in the pictures was anything but. My jaw dropped as I realized that each one was a different kind of kinky. In the biggest frame, poor Brandon was spending what looked like some "quality time with Daddy," if you know what I mean. Heather stood in the background, of the photo, smiling evily as she kept Brandon in place, preventing him from moving. Brandon was completely naked, his hands tied behind his back and a gag in his mouth. Behind him was Connor, holding onto his hips. Brandon's body was tense, and his face showed a mix of terror and humiliation. I could only imagine what Connor was doing to him. "Oh, that one is the night Brandi's sissy cherry got popped," Heather shared following my gaze to the picture.

"I have a whole baby album of Brandi bursting with pictures," Heather continued explaining. "Especially ones featuring her and Daddy, but this one is definitely my top pick! Over there," she gestured to a larger photo above the crib, perfectly placed for everyone in the room to see. In the photo, Heather was on top of Connor, riding him cowgirl-style. Her boobs were out for Brandon to stare at helplessly from his crib. Her body was glistening with sweat and her face was full of pleasure. She had a very obvious smile as she stared into the camera. "That was the first time I fucked Connor," Heather recalled with a gleam in her eye. "The night that little Brandi lost her sweet and submissive girlfriend forever. I want that image to be the first thing she lays eyes on in the morning and the last thing she sees before bedtime!" I couldn't help but notice other photos scattered around the room as I looked around too.

Above the changing table, hung a very candid photograph in a pale pink frame, decorated with images of teddy bears and baby blocks. The glittery letters at the top spelled out "Daddy's Girl." This picture was definitely my favorite so far. In it, Connor had Brandon pinned down over his knee, delivering a stern spanking as Brandon's pink princess pull-ups bunched around his ankles. His bottom was covered in angry red handprints, and drool dripped down his chin. If Brandon's face wasn't buried balls-deep on Connor's dick, I'm sure we would see the face of a very sorry sissy baby.

Heather exclaimed, pointing at the photo. "That's Connor's favorite method of spanking Brandi! He'll keep going until she can make him cum down her throat! It's hilarious when Connor makes her count each spank while his dick is buried deep in poor Brandi's mouth." She even mimicked the gagged blowjob, making sounds like "Unnn... Toww... Phreeeww..." She giggled, as if she had a mouthful herself!

#humili sissi

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