Saturday, January 7, 2023

Sissy Cucks and Sucks

Continued from: Bella's Pony Play

This is the lockable cage that sissy Tiffany (aka Andrew), will be spending some time in while I fuck his girlfriend Katrina. As described in the previous post, Katrina wanted to evolve her boyfriend's humiliation by not only continuing his forced feminization and chastity, but also to begin cuckolding him. 

The cage is located directly beside my bed and due to it's small size, Tiffany will likely be forced into a crouch position for the majority of my session with Katrina. Who knows, my receptionist Cassandra might even stop by and join in. 

The three of us were all sitting at the dining room table and working through the details of the session. 

Katrina brought Tiffany to the session, already dressed like a little girl and made-up for us. Cassandra, although she was not working at reception today, put him into the usual "waiting-room predicament" so the three of us could chat. 

It must have been dreadfully humiliating for the poor sissy, having to listen to us whisper and giggle from the dining room. We learned that Katrina didn't tell him why she booked him a session today. For all he knew, he was there to be spanked.

Cassie and I had the foundations of a plan for what we wanted to do with Katrina. We just needed her to fill in the blanks. She told us that she wanted to be poorly treated, called names, degraded and dominated sexually throughout this session. She wanted the illusion for her sissy to be, that she was just some "free-fuck" in a high-end hotel room, posting herself all over the internet for casual hook-ups. 

I nodded at Cassandra in agreement. The foundations of our original plan would track with this very well actually. I explained to Katrina that I would have a difficult time calling her degrading names like she wanted me to, but I understood how arousing it will be for her. 

"Just remember I'm playing a role Kat. I would never ever speak to you in a manner like this", I reassured her.  

"Ya, ditto." Cassie chimed in like a teenager, with that nugget of reassurance. 

I told Katrina that we're going to play around with gender roles a bit too, and told her to treat Cassie and I as though we are male. 

She looked excited. Her face and neck were flushing with arousal. 

"Alright Kat, take Tiffany upstairs and lock her in the cage while you get yourself dressed and ready. I'll text you when Cassie and I are good-to-go, then I want you to kneel and face the wall near the cage." 

"Simply tell Tiffany":

"My Master likes me to dress in lingerie and slutty heels, and wait for him like this on date nights." 

We all giggled together. This is gonna be hot!

Katrina had her sissy in shackles and stowed away while she got ready, then knelt down to likely tell him for the first time, that he's about to watch her get fucked. 

Cassie and I were ready, I text Katrina, who got herself into the requested position to wait for me. 


"There's my little hotel slut! Hello slut. Turn and face me, keep your hands on your head and stay on your knees". I ordered.

"Yes Master", she said right away. 

I had taken my hair extensions out and dressed up like a man. Tiffany could hear my voice and knew it was me, but what she couldn't see, was the giant bulge in my dress pants. 

I kept ordering Katrina around, while she continued to call me Master. I had her turn and face the wall again, while I sat and spoke to Tiffany in the cage. 


"So this is your girlfriend I understand? Isn't she everyone's girlfriend?" 

"Yes Mistress", Tiffany said, in a knee-jerk reaction. 

"It's yes Sir, sissy". I scolded. 

"I'm sorry Sir, yes Sir", he said. 

"Tonight, Katrina exists in this room for my pleasure, and anyone else who might pop by for a drink, isn't that right slut?" 

"Yes Master", Katrina instantly responded. 

"Hell, maybe I'll even post her juicy ass on some escort sites, she can make me some dough tonight". I followed up. 

Tiffany whimpered from the cage, as he now understood the overall "just" of the session that was about to occur.  

I pulled Katrina by her hair, over to the side of the cage. I claimed her pussy as mine, by grabbing it and rubbing her over her panties. 


"From what I understand, you don't get to have this do you sissy?" I asked Tiffany. 

"No Sir", he peeped. 

"It’s mine now isn't it?" I said as I continued to rub Katrina, while she moaned like a whore. 

"Yes Sir it is", he peeped-out again. 

"I'll tell you what else is mine, this whorish mouth! Get on your knees slut", I barked at her, while gearing my pants off. 



Tiffany's only vantage point was now my men's style dress socks and shoes, and his girlfriend's stockings while she knelt. A perfect illusion for him to see. 

"Get my dick hard, bitch!" And with that, I slapped her face. 

For the benefit of Tiffany listening, Katrina cried out with an "ouch", then she winked at me before proceeding with my cock. 


"That's my good little cock-whore, now into your mouth with it. Show Master how much you love sucking cock!" 

I kept the narrative going. I was saying as much as possible to remind poor Tiffany that his little cocklette is in an inescapable chastity device.

I took things over to the couch and began fucking Katrina, in full view of the cage. 


Katrina was definitely being extra vocal, for the benefit of sissy Tiffany. 

"Head down, ass up bitch!" I hissed, as I pinned her head down with my shoe and continued to pound her.


I grunted and moaned and simulated the sounds of cumming inside her pussy, then ordered her to get in a "down" position on the floor. 

I pulled out my phone, this was all scripted in advance of course, and called Cassandra who was downstairs. I created the illusion that I was calling some buddy. 


Here's what Tiffany would have heard from the cage and Katrina from her down position. 

"Hey Man, what you sayin'?"

"No just chillin tonight, I've got some random piece over".

"No not her, a different one". 

"Serious bro, I just busted right in her cunt, no condom". 

"Ya she wouldn't mind a DP. Seriously, you comin' over?"

"Alright see you shortly then".

"...yes I'll loosen up her ass". 

"ATM?...no that's cool, she'd totally be into that bro".

"Ya, ya...ya, just let yourself in". 

*bleep*

"Did you hear that slut? You get to take two cocks tonight!" 

"Thank you Master", Katrina spoke into the floor. 

"Come clean my dick off. I guess I need to use it again", I said to her.

Katrina sucked and gagged on my dildo for a bit, all while Tiffany watched on in desperation and humiliation. 

Cassandra gave us a few minutes, then rolled in, dressed like a dude. She gave me a "hey Man", as she approached. 

"Don't be shy bro, this bitch can't wait to get two cocks in her!" 


Cassandra got out of her pants and took a seat on the couch. Katrina silently mouthed the words, "I'm loving this", to me, while she once again knelt. 


She started sucking my dildo, while stroking Cassandra's. She was gagging and retching loudly, likely for the benefit once again, of her poor, caged sissy. 


Between laboured breaths, Katrina gasped out to Cassie, "I want your big, black cock Sir! Please fuck me."

"Up your ass?" Cassandra asked her, playing into her role.

"Anywhere you wish Sir", Katrina responded. 

During our initial planning meeting in the dining room, we hadn't planned on Katrina taking it up the ass tonight. She told us she has limited experience with anal and would need some training and stretching first. 

But we can certainly let Tiffany hear us pretending to fuck his girlfriend in the ass...


As Cassie entered her, Katrina cried out, "Ohhh gawd your cock is so huge Sir!" I think it turned her on, trying to speak coherently while my dildo was in her mouth. She was ready for her first of several orgasms that would follow.


Cassandra and I continued to spit-roast her, eventually moving to the floor to create a better view for Tiffany. His poor cock must be straining against the confines of his chastity cage by now. 


"Is Tiffany looking forward to being spit-roasted by two dudes, slut?" I asked Katrina. She didn't respond as my cock was down her throat. 

I yelled over to the floor cage. "Sissy, do you want to trade places with your girlfriend?" 

"No Sir", conflicted and embarrassed, he whispered out in shame. 

"I'm gonna let you taste her filthy cunt, sissy. But you'll be tasting it off my dick once I finish inside her again", I called out. 

"Thank you Sir", Tiffany replied. 


We eventually got Tiffany out of the cage and a little closer to the action. Katrina had orgasmed again, onto Cassandra's cock and another onto mine. We had fucked her all over that bedroom in a variety of positions, while Tiffany was bound and gagged, being forced to watch the ravaging of his girlfriend. 



I put my suit jacket back on to look more dude-ish, before we untied Tiffany for his final act of degrading humiliation. 

Katrina, now well spent and satisfied, relaxed on the bed and watched her boyfriend clean her pussy juices from my cock. 

All the while I was pestering him about being a pussy-free sissy. 

"This is the only way you get her pussy isn't it Tiffany? From sucking a cock that just finished inside your girlfriend?" I tormented. 


He held my dildo in his little satin glove and cleaned every inch of my dick, while Katrina watched on in vengeful delight. 

"Cassie huni, can you take this pathetic sissy down to the stage and put her in timeout. She can reflect on this session while I debrief with Kat", I said. 

"Yes Sir", Cassandra responded, as switched on as ever. She never misses a beat that girl! She maintained our fantasy roles perfectly. 


Katrina and I embraced on the bed and she thanked me for the wonderful session. She said it was an amazing experience. 

"Where did you find that Cassie girl?! My god she is a handful!" Katrina giggled. 


"My personal little stripper! Yes she's something else alright", I replied. 

"If we're slowly escalating with my sissy Ma'am, where should I take things next", Katrina asked me. 

I suggested that the next logical step might be to try Tiffany with a second sissy slave, to see what they'll do with each other, if it means their dicks will be unlocked. 

"But Andrew isn't gay, Mistress", Katrina injected. 

"You'd be surprised huni", I cooed to her. "Orgasm denial does amazing things to silly boys".

She giggled out loud in delight. 

I then suggested to her that a boyfriend or "bull" could be introduced to their dynamic, so she is not depraved of real cock and being fucked when she wants. 

"That sounds hot Mistress. Does my bull get to use Tiffany too?" She asked. 

"Time will tell sweetheart. We'll take it slowly and I'll help you, if that's your ultimate goal", I coached her. 

"Thank you Mistress. May I go down on you before I take Tiffany home Ma'am?"

"Of course you may!" I purred. 



Mistress Andrea


xoxo

Continued in: Summer gets caught













 



3 comments:

LouisaIsabella said...

Mmmm that was so hot. 🔥 Not sure who I would have liked to be more. 😈

Mistress Andrea said...

Difficult to pick a role, huh? Ha

SissyLenaFr said...

what a magnificent scene, Tiffanny was terribly humiliated to have to watch her girlfriend being manhandled by her 2 "men"
the hardest part must be cleaning the toys

Christian Christmas?

Continued from:  The Season for Giving A Sarah Jane story With a final squeeze of Mistress's hand, I turned to hurry from the room, my h...