Mommy's sissy gets a new name

Continued from: Summer is a Natural

I felt like I missed her already, I didn't want her to leave...

"How long will you be gone Summer?" 

I innocently asked her, sounding almost submissive in my tone. It was an easy role to find myself slipping into, as I admired the beauty and sexuality of her work attire and her high heels, while I remained barefoot. 

"I have to do YYZ to Vancouver first, then down to San Francisco, over to Atlanta, then back home Mistress. Three days in total".

She poured me a coffee and joined me at the table while we chatted. 

Summer started to giggle. "You have Andrew to keep you company until I'm back Mistress, no?"

 "You must mean Tiffany?" I replied, also giggling. 

I had given Andrew the sissy slave name of Tiffany from now on, when he is in the presence of Summer or I. Even after his workout session with Summer there was no orgasm permitted and he remained frustrated, in his chastity cage. His level of desperation for release, should have him willing to do just about anything for me. 

"That's a fun and girly name!" Summer said, holding back more giggles.

"Come huni, I'll walk you to the door so I can say goodbye properly", I seductively said to Summer as I helped her with her luggage.

"I'm going to miss you Ma'am", Summer caringly spoke, flashing her doe eyes at me. 

I pulled her onto my lap like she was a little girl and kissed her goodbye. I felt it immediately between my legs, a current of arousal that shocked my entire body.

"I'll make sure to save you some sissy, for when you get back little one". I whispered into her ear. 

"Mmmmm, thank you Mistress. Take lots of pictures for me". 

I giggled and purred into her neck, making sure to transfer some of her perfume onto my nose. I'll do a lot better than just taking pictures! I thought to myself with a mischievous grin.

And with that, she was off.

"Mommy"...had to start getting ready for sissy Tiffany.

When clients attend my facility for a session, they are first directed into a stark, clinical feeling, locker room. They are instructed to place their phone on silent, remove every stitch of clothing and along with purses, wallets or car keys, they are to place everything into a locker and shut the door. The locker units lock upon being closed and my clients do not have access to a key. I find this adds to their vulnerability and psychological feelings of helplessness, being physically separated from their clothing and belongings.  

I have future plans to ensure there are multiple clients stripping naked together in this locker room before their sessions. Male and male, female and female, male and females together. All to add to their humiliation. All of my male clients are kept in chastity cages they cannot remove, so I certainly don't need to worry about any hanky-panky between male and female clients. 

When they emerge from the locker room, ashamed and bare naked, they will be invited into the waiting area where they will be gagged and bound to the chairs provided. Legs forced open so their full genitalia is on display to the room.

I'll have a receptionist watching over them and assisting with the binds. Having a young, pretty receptionist will, as always, FURTHER add to their shame and humiliation while they wait for their spankings. 

This is all a nod to one of my all-time favourite, Literotica stories. "The Facility Part 1"

I have never been able to read this story without my face flushing red, without masturbating or having my heart pound out of my chest. It was the inspiration for setting up a facility of my own in Willow Creek, for the kinky and lovely people of this community. 

Speaking of which. Tiffany just emerged from the locker room, bare naked, looking very sheepish and wearing only her clitty cage. Although I would like her in the waiting room to reflect upon and anticipate what's coming, Mommy has to give her a sissy makeover. This should allow her the same amount of time to anticipate what's coming. 

I picked out a beautiful 1950's pin-up dress with nude Mary-Jane heels. I added pearls, deep red lips and wore vintage lingerie and seamed stockings underneath the dress. Lastly, I made it clear to Tiffany that I was to be addressed as "Mommy", until the session was over and that he was going to be spanked until he was crying like a little girl. 

I took Tiffany over to the floor mirror so she could see her entire transformation, right from her lace ankle socks and gingham heels, to her eye liner and wig. Andrew was so dreadfully humiliated that I could see he was on the verge of tears. He looked ridiculous in his pink satin, organza dress.

He turned back around and began to plead with me not to spank him. I had to remind him to say it properly and to use a wispier voice. 

"Please Mommy, don't punish me. I'll be a good little girl I promise". He recited out, his voice cracking as he did. 

"Ohhh I know you will Tiffany, are you going to take cock for me like a good girl?"

"Yes please Mommy, please let me suck cock!"

Andrew continued to degrade himself. What a mindfuck for a heterosexual, once alpha male, to be reduced to a sniveling sissy slave, begging for cock. God I love the effects of long term chastity! 

 

I left his frilly panties up and ushered him across my strict lap, raising my dress just enough so my stocking tops and garters would be exposed. The camera was recording, I was all ready to administer a long, hard spanking. 

I used my hand over his panties first, before selecting a rubber-soled slipper of mine. The loud thuds from the slipper sole would definitely be heard from the sidewalk outside. 

I used a riding crop to target his smooth, hairless thighs, before moving to the loveseat for some OTK.

I finished up his warm up, reminding him that his spanking was certainly not over. Tiffany collapsed down into a kneel, fighting off tears. I extended my high heel and told the sissy to thank me properly. 

Tiffany spent the next little while, gently cradling my foot while kissing and licking my high heels. 

Just to fuck with his mind a little more, I gave the sissy a predicament option. I asked if my naughty little girl would like diapers, or cock. 

I watched Tiffany look over to the dreadful nursery area and shudder. I have tormented him in this space before. A bondage crib, a little girl potty and high-chair, diapers and enema kits. It was a tough decision for a desperate sissy. 

At least when I fuck Tiffany in his sissy pussy, he gets some pleasure via his prostate, and he usually dribbles out some built-up cum from his chastity cage.

"I'd like to take some cock please Mommy", she wisped out, with her bottom lip trembling. 

"That's a good choice my sissy doll", I teased. "We'll get you into those crinkly diapers after you've taken some cock".

When I said this he hung his head in defeat. As if he didn't know I'd be giving him both! I just wanted him to choose, to further humiliate him. 

"Yes Tiffany, you'll be spending the night bound inside your crib, trying your hardest not to wet your diaper before morning. Because what does Mommy have to do then young lady?"

"I get punished Mommy". Andrew was now in tears. 

"That's right young lady. If Mommy has to change your wet diaper, you'll be getting Mommy's ebony hairbrush on your backside”. 

I shackled Tiffany to the bed and padlocked a ballgag in place, leaving the video camera rolling. I told him to take some time to reflect on his predicament and finish up his crying. 

I needed to get out of my dress and into my strap-on anyway. It's gonna be a LONG night for this sissy slut!

 

Mistress Andrea

xoxo

Continued in: Sissy is fucked and diapered