Sissy School, Part 3: Finale (Story)
"Ooh, this is gonna be fun!" I giggled to my girls as we watched the bouncer finally cum down Brandi's throat. But then, the live stream cut out, leaving us hanging! My phone rang, and it was Huggies. "Hello?" I answered, very excited. It was Staci, all too happy to explain that the Huggies staff usually like Mommies to see their sissy's first detention in person! "Well, I'd love to!" I laughed, feeling tipsy from the wine but still able to drive. "Can I bring friends?" I asked, seeing Lyndsey and Kylie's eager smiles.
We rushed across town to the seedy strip mall, just in time to find Brandi tied up and gagged in the nursery, alone and waiting for us. "Well, well, well, Princess Pampers," I giggled, standing before Brandi with my hands on my hips. "what did you do this time, hmm?" I asked, tapping my foot like a disappointed mother. My poor sissy looked up at me from the oversized mechanical baby bouncer, her eyes full of tears. "Are those tears because of detention or because they left the butt plug in?" I teased, squeezing Brandi's tear-streaked face.
"Probably both," a stunning woman I hadn't met before said with a smile as she entered the nursery. Wow, everyone that worked here was hot! She was a bit older than Staci and Becky, maybe in her early 30s, with almost black hair, amazing boobs, and a perfect ass. I would know, right? Because her whole outfit was just a skin-tight leather bodysuit! It was showing off more than it covered! The other girls wore short shorts and crop tops to do their thing, but this woman's outfit was the size of a one-piece bikini, and tight! "Ms. Penny," she introduced herself, very confidently. I could see why! “Staci and Becky are the teachers here at Huggies, I’m more like the Dean of Dicipline. I hand out detentions!”
I stood there, staring at how ridiculously gorgeous this woman was, as she crouched next to Brandi, still bouncing in the bouncer. "Three demerits on your first day, huh? Y’know, that’s a record. You're either a very naughty girl, or Ms. Staci really doesn't like you," Penny said, stroking Brandi's cheek. Brandi tried to argue behind her gag and got slapped for it. "I don't really care why you have them," Penny said plainly. "You have them, so I'm here. And it doesn't look like anyone's going to stop me, right?" Brandi and Penny both turned to me, Brandi begging with her eyes, and Penny raising her eyebrows, almost asking permission.
"Well, that's that," Penny winked at me when I didn’t stop her. "Wanna know something fun?" She leaned in, almost whispering to Brandi. "All the rooms you've seen so far? That's not all the fun we have for you little girl! There's a whole basement, where the really naughty girls go! It’s a lot more, uh…intense than the regular Detention Room! It's even soundproof, so no one hears the naughty sissies cry when we punish them!" She smiled up at me, her eyes sparkling. "And it shares a wall with the men's bathroom at the club next door. I’m sure you ladies see where this is going, right?” Oh God, this was going to be really fun to watch! “Shall we head downstairs?" She giggled
Without a word, two muscular men entered the room, their eyes fixed on Brandi. "It's a bit on the nose," Penny laughed, gesturing to the men's Chippendales-style bow ties and shirt cuffs. "But who cares? Look at those arms!" She wasn't kidding; they were ripped! "I love watching them manhandle losers," Penny said, sounding like she was turned on! "Downstairs, boys!" she ordered, and the men lifted Brandi out of the bouncer, her cries and pleas muffled by the gag. We followed behind Penny, listening to Brandi's sobs as the strippers dragged her down the hall.
"Here we are," Penny said as we reached the bottom of the stairs. The basement of Huggies was nothing like I'd expected. There was no fuzzy white rugs or pink walls. It was just exposed stone walls, a few light bulbs, a couple of doors and one way mirrors on one wall, and some wild ass bondage gear in the corners of the room. It felt more like a dungeon than a nursery! "The Box," Penny smiled, pointing out a gigantic plexiglass box on wheels, almost like a coffin with a few holes lined in rubber. It was bizarre. "And over there," she pointed across the room, "is the Bench."
The Bench was even more weird! It was some huge black metal frame that was padded in hot pink velvet, with fuzzy cuffs at all four ends. It was also sitting on some giant turntable. Kylie looked like she was freaked out too, Lyndsey looked like she was going to cum just looking at the place. Penny smiled at Brandi, who looked absolutely terrified, her legs kicking as the men held her in the air. I'm sure her Pampers were soaked by now! "Would you like to choose, or should I?" Penny asked the trembling sissy.
"Well?" Penny asked, trying to hold back a smile while she waited for Brandi's response. Of course, with the penis-shaped pacifier gag jammed down her throat, Brandi couldn't say a word. Even without it, I doubt she'd be able to speak. I'd never seen her so terrified; she was shaking like a leaf! "Don't worry, princess," Penny cooed, walking over to the sissy and stroking her cheek. "There's plenty of time to play with all my toys. Now that the secret's out, I can tell you the good news! Remember how Ms. Staci said your Mommy paid for a year's tuition? Well, surprise! She paid for you to be down here with me every day! I have so many more games for you to enjoy!"
Penny walked over to the intimidating thing and lifted the lid. "The Box it is!" When the dominatrix opened it, I noticed the box had a very serious looking steel shackle attached to chains at each corner. I guess Brandi wouldn’t be going anywhere any time soon! There were also four pink rubber pads in the center, spaced out, I had an idea of why. "In you go, sissy," she clapped, and the two beefy strippers carried Brandi toward the Box, still not saying anything. "Mmm! Mmm! Mmmmmm!" Brandi squealed as they lifted her high in the air, her body stiff with fear. I couldn't look away as they roughly placed her in the Box, belly first, her cries growing louder. One man wrapped his arm around her neck, forcing her to her knees.
"Make sure she's snug, boys!" Penny laughed, and Lyndsey giggled wickedly as we watched the men cuff Brandi into the Box, her limbs stretched by the shackles. One of them untied the pacifier gag, removing it before quickly forcing an o-ring gag into her mouth. "There you go, princess," Penny said, looking down at Brandi's sobbing form. "Now your mouth is wide open!" She shrugged, not concerned with Brandi's protests.
Penny closed the lid, trapping Brandi inside, her cries immediately quiet. "Sound proof," she smiled at me. "Nothing gets out, only in," she continued, and then pressed a button I couldn’t see somewhere on the Box. A weird hiss sound started coming from the thing. "Sealed in, nice and tight!" Penny explained, patting the lid. Brandi was absolutely freaking out, her body thrashing against the shackles, but I couldn’t hear a thing! Mm, something like this would be fun for home!
"For my next fun trick," Penny stuck her tongue out at us, then turned to the strippers. "Make sure she's even more snuggly, boys!" All three of us gasped when the guys started to push on either side of the Box. Holy shit, it was getting smaller! Penny laughed. "It expands to lock sissies in, then it collapses nice and tight! Isn’t it so fun? No loser is too big or small for The Box!" I just stared, mouth wide, as Brandi struggled, her face and ass squished against the plexiglass. The guys somehow locked it in place, and Brandi's face and ass were literally flattened against the Box's sides. "Don't worry," Penny said with a cruel smile, "she can still breathe...for now."
Penny just kind of stood therefor a minute, watching as Brandi struggled. I swear, she was playing with herself over her bodysuit! "Mmm," she moaned, throwing her head back, closing her eyes. "I love that look when they realize they're trapped..." She was just standing there, running her hands up her body! This girl was fucking wild! After her little moment, she snaps back and goes, "alright, boys, test her out!" One of the strippers opened some door at the front of the Box, and Brandi’s gagged little mouth popped out!
“Mmm, what's this for, you think?” I giggle, Kylie and Lyndsey following me as I walked to the back of this box. There's a smaller hole in the back, right where Brandi's ass was, but it's too small to fit anything fun. Then I spotted a few others lining the whole thing. I had no idea what the Box was for, but I was excited to find out! "Oh, look at that!" I squealed with laughter, seeing Brandi’s ass for the first time today. Before putting the poor thing in her bouncer upstairs, it looked like they had cut a hole in her diapee and then filled her up with a hollow buttplug! It was massive and it left her sissy pussy wide open.
The girls and I were having a blast watching my little sissy Brandi squirm in there, all chained up and helpless. And then, we find out what Penny meant when she said ‘test her out’. One of the hot-as-fuck strippers pulls down his pants and, like, wow. This guy had a cock that belonged in porn, and his body was to die for. I could totally ride that all night, but right now, I think it was for my lucky little girl!
“Go for it baby!” I cheered on Mr. Hot Stripper as he walked up to the Box, with his hard cock in his hand. He lines up that thick shaft with the hole right in front of Brandi's gagged mouth, and I notice the hole was lined with something all soft and velvety! Holy shit, Penny had turned my sissy into a fucking fleshlight! The stripper shoved his cock through, and Brandi's eyes went wide as it stretched her throat. The poor sissy slut started crying, trying to beg for mercy, but all that comes out are muffled whimpers. This guy didn’t give a shit; he just starts throat-fucking my little princess like its a porno!
I could see his face turning red as he went deeper, he was not holding back! “Take it you fucking slut!” He was grunting, thrusting his hips and making poor Brandi’s eyes bulging. He's using her mouth like he owned it, God he was hot. “I want to hear you gagging bitch,” he screamed when Brandi tried to pull away, “you stop when I tell you to stop!” He must have been at it for at least five minutes straight, not stopping once. He would pull out just far enough for the sissy to catch her breath, and then go right back to it. I could see his cock bulging in her throat!
"Enough whore," the stud commands, stepping back after going at Brandi’s throat as long as he wanted. We all clapped, loving every second of it. He made the poor thing gag, choke, she even spit up at one point! Staci was so right, I loved watching Brandi suffer in detention! But this hunk wasn't finished with my little sissy. He warned her with a growl; "you’ve got 30 seconds, bitch. I'm gonna fuck your mouth and fill your throat!" The poor thing started crying harder of course and just stood there stroking his cock watching her. Fuck he looked all dominant and powerful.
He didn’t even warn her, he just walked up and shoved his dick back into her mouth. Mmm, maybe he’d do me next. This time, he was going faster and harder, he wasn’t stopping again, not so this little bitch could breathe! I could hear his hips thrusting into the plexiglass he was fucking Brandi’s mouth so hard! I watched the trapped Sissy’s eyes go wide and her body convulsing as she tried to take his length. She tried to wiggle away but the Box was not letting her escape.”Fuuuuck!” He grunted finally. My sissy's eyes bulged, working overtime as she swallowed his hot load. She was crying, choking on his cum, but he didn't stop until he emptied every last drop down her throat.
“Aww, crying already?” Penny laughed at Brandi, “that was just one dick though! There’s so many more!” She gently pushed the naked stripper out of the way and grabbed the handle of The Box. She easily moved the thing across the room. “Wheels of course,” she explained, “helps get the little loses to some fun places!” I watched as she rolled Brandi to a stop and opened a door in the basement wall. “Lots and lots of fun places,” she winked, pointing out a plexiglass panel on the other side of the door. This one had a hole too, a hole that looked a lot like the one Brandi’s mouth was hanging out of!
Penny spun the Box, bringing Brandi's terrified face in line with the hole. "This," she explained, "is the bathroom at Hunks next door. There's gonna be a lot of strippers and customers who'd love to use our little sissy’s mouth tonight. And some of them might be rougher than what you just saw!" She raised her voice so Brandi could hear. "So, I hope she don't cry every time a real man fucks her throat! No one wants to hear a sissy whine! Oh, a few more things,” she said, and walked across the room to a closet. She brought back a whole cart of tubes and something that looked like an oxygen tank! What the fuck?
“Watch,” Penny smiled at my confused look and began screwing tubes into the holes in the plexiglass coffin. "Those pipes here," she pointed at a bunch of pipes on the wall next to us, "are for the toilets there! And these," she pointed to tubes, “connect to those pipes!” I started giggling as I watched her finish connecting the last pipe, “which means poor Brandi’s little box will very slowly fill up all night!" Lyndsey, Kylie, and I burst out laughing. "She'll have to hold her breath when someone fucks her face if gets too high though!" Penny laughed,
Penny hung the tank by a hook and winked, holding up a small dildo attached to a plastic tube. "And this," she said, jamming the dildo-shaped nozzle into Brandi's ass, "goes right here." I swear I heard Brandi scream behind her gag as the laughing dominatrix invaded her defenseless asshole. Penny connected the tube to the tank, tapping it with her sharp, red-painted nail.
"In here is a special sissy enema! Warm water, itching powder, caffeine pills, and, as a special treat for Brandi, viagra! It'll keep our sweet girl awake and horny in her chastity cage all night. She'll be uncomfortable, but at least she'll be alert while sucking cock! The club's open 24/7, so she'll have plenty of 'friends' to keep her busy till you pick her up. Tomorrow night.”
I was disappointed that I wasn’t going to be able to watch every one of Brandi’s detentions in person. But I did know that Huggies was the best money that I had ever spent!