The elusive sissygasm

Continued from: Sissy Slave Fucked and Diapered

I had Tiffany straddle my strap-on cock while he was still wearing his puffy diaper. I encouraged him to look to his right and watch himself in the mirror as he rubbed-off on the dildo. I calmly explained that since his little peenie is locked up, he needs to learn how to cum like a girl, through rubbing or through being penetrated in his sissy "pussy".

Tiffany tried to transfer some stimulation to his chaste penis, by riding the shaft of my dildo, all while I coached him along and told him he was a good little girl. Alas, it was no use. He only became more aroused and frustrated, with no sign of release. 

We eventually got him out of the pink crinkly diaper and I suggested we try some thinner, adult baby pull-ups, with little animal print patterns. 

I had Tiffany straddle the Sybian machine and turned it to a medium setting. 

"It's ok if you make some cummies into your pull-ups for Mommy. Squirt like a girl for me from your chastity cage". 

I encouraged poor Tiffany to try and have an orgasm, with his little dicklette still locked up.

I watched and recorded the show, as he moaned like a whore whilst riding the device. The stimulation was reverberating all around his penis and anus. 

"I think I'm also there Mommy!" He cried out, as he continued to ride the Sybian. 

"You must be so wet for Mommy. Show me you can cum like a girl!" I continued to encourage. 

I wanted Tiffany to mentally associate his pleasure with taking cock, so I approached him and had him take my dildo into his mouth, while he enjoyed the vibrations of the machine.  

 I took another photo for Summer, with the dildo in his mouth, before I turned off the Sybian machine. 

"No cummies huh?" I used a discouraged voice. 

I saw his bottom lip quivering and tears roll down his cheeks from the frustration and humiliation. 

"No Mommy"....There was a long pause. He crawled over to my seated position by his make-up station. With his eyes down he meekly asked me:

"Could we try penetration again Mommy? Then maybe I can cum?" 

Quite the eager little slut, I thought to myself. Three months in chastity has certainly turned this alpha male into exactly what I had hoped he would become, a cock-hungry, sissy slut. 

"Fluff my cock young lady", I purred to him.

He sat up on my knee like a little girl and began to stroke the cock with his ruffled, lace gloves. 

"Good girl! Moan like a slut for Mommy, show me how passionate you are for cock". I used my words to humiliate him further. 

"That's it Sweetness! Now down on your knees. You know what girls are expected to do now". 

"Yes Mommy", he whispered out, choking back tears. 

"Kiss the length of my shaft, good girl Tiffany! That's it. Worship that huge cock!" 

I continued my encouragement and emasculation of Andrew, listening to him gag on the penis and watching him kiss it with his painted lips.

We adjusted him up onto the chair, on his knees. He was good and ready to accept my cock into his sissy pussy. He was so desperate for release. I slipped him out of his little training pants and with a generous glob of lubrication, I entered Tiffany from behind. 

"Mommy, my clitty feels like it has to pee!", he mewed out in desperation. 

"That's the sissygasm building Tiffany, don't fight it! Let it happen". 

I got him onto the floor to try fucking him harder, hoping he would experience an orgasm this way. 

When the sissygasm continued to elude us, I took Tiffany over to the pink fucking bench, and secured his ankles in place. 

"Alright young lady", I spoke. 

"This is definitely going to work this time, with your legs in the air like a slut. I'll pet your balls and massage your cock cage while I fuck you ok?" 

I was determined to have Tiffany spurt for me. Just to qualify in her mind that it is actually possible. 

Forced to now stare at me, along with his precious Mary Jane heels and lace socks, I entered him deeply while massaging his swollen cock cage. 

Success!!

I watched Tiffany moan and whimper, as a few thick, powerful spurts of cum escaped his clitty cage and splashed down onto his stomach. I kept fucking him for a few moments longer, to milk out any remaining cum. Several more dribbles oozed from him cage and cascaded down by his balls.

"Good girl!" I praised him, as I removed my dildo from his "pussy". 

"You did it Tiffany! How do you feel?" I excitingly asked him. 

"That didn't really feel like an orgasm Mommy", he whimpered to me while pouting. 

I chose to ignore what he said completely and kept playing-up the fact that this was a huge step for him and a huge success in his transformation. 

"Look at all the cummies you made for Mommy! Open wide little one", I Mommy-voiced him. 

Andrew reluctantly opened his mouth and I scooped up all of his cum and fed it to him. I even flung some onto his face so he could wear like a badge of honour for me. 

"Swallow that down for Mommy. You need to get used to swallowing loads of cum Tiffany". 

His face twisted and looked disgusted as he swallowed his own sissy cream. I had him kneel for me in submissive pose. I wanted to take a photo of the cum on his face to send to Summer. 

I knew this was only a milking for him, a ruined orgasm, like a prostate milking. It was all very emasculating and humiliating but at least he felt something. 

My next plans for Andrew will be some cuckold scenes, first having to watch me with another girl. Then I'll escalate to me with a male slave while he watches. Finally I'll have him fluffing real cocks for me, and force him to watch me ride a dick he just sucked. He can be on cleanup detail too, if he ever wants his mouth to go near my pussy. 

These were the thoughts running through my mind, as I locked Tiffany into the cage in the sissy room. I gave her my final instructions of the session. 

"I want that cum to remain on your face Tiffany. You served Mommy well this weekend. I want you to spend a few hours in the cage to think about all we accomplished. When your time is up, I'll come release you and escort you to the locker room where your silly boy-clothes are. This will conclude your session, is that understood?"

"Yes Mommy, thank you Mommy", he recited, without hesitation or delay. 

Very sharp and well trained! I thought to myself as I left the room and went to fill the tub. 

I checked my phone to see that Summer had landed safely in Atlanta and had made it to her hotel room. 

I sent her the photo of "Tiffany" with cum all over her face.

There she is!! 

I sent her back a message, telling her that she looked yummy and cute. I'm going to allow her to masturbate for me, but I'm going to direct her exactly how to do so! This should be fun, I thought to myself, as I settled into the tub for a long soak.

Mistress Andrea

xoxo

Continued in: Bella's Daughter Cassandra

Sissy slave fucked and diapered

Continued from: Mommy's Sissy gets a new Name

"Well Tiffany, are you ready to show Mommy what a good little girl you are, or do you need to be taken over my knee again?"

I used my Mommy tone to torment the helpless sissy slave, while he was still gagged and bound to his princess bed. I had left him in this humiliating predicament and ridiculous outfit, following a warm-up spanking I gave him during: Mommy's Sissy gets a new name.

I had left him alone for twenty minutes, with his shame and embarrassment, the key to his chastity cage nowhere in sight. His predicament was disparaging, yet I always provided a glimmer of hope that I might unlock his penis for some edging, perhaps even a ruined orgasm, if he is obedient and feminine for me. 

But for now, it was MY cock he needed to focus on, if he knew what was good for him. 

After I removed Tiffany’s shackles and the ballgag, I ushered the sissy over to the windows and told him to kneel like a good sissy slut. 

He wasted no time in getting the dildo into his mouth and trying his hardest to please me. 

I stroked his wig, repeatedly calling him a "good girl" and reminding him that this was all being filmed for my pleasure. 

When it was time to fuck his ass, I made him ride me like a girl on his princess bed. Surrounded by mirrors so he could watch his own humiliation. 

Tiffany moaned like a whore, when my large dildo entered his tight, sissy hole. I told him that this is the way to please real men, by facing them and riding real cocks. 

I don't know what was more mortifying to Tiffany in this moment, having to face the windows in his sissy attire, riding my dildo, or having to face the video camera in reverse cowgirl. 

I was starting to feel that Tiffany had too much control over the depth and tempo of her fucking. Although very degrading, having to fuck herself on my cock, it was time to get her out of her dress and let Mommy take over.

I secured Tiffany into a floor pillory with a heavy metal collar, securing her neck to the bondage apparatus. I re-lubricated her and told her to be very vocal this time. I wanted her crying out that she loves being fucked and pleading with me to pound her harder. 

I eventually returned him to the princess bed to finish him off, with his legs in the air like a total slut. He was forced to look me in the face as he struggled through the deep fucking. His shame and humiliation was catastrophic at this point. He was so vulnerable yet still so aroused, it should be easy to get him into diapers and into the nursery after all of this. 

"I bet you want those diapers now sissy?" 

I taunted him, making him think about his original choice of wanting cock instead of a diaper. 

"Yes please Mommy. Please don't fuck me anymore", he whimpered, with tears in his eyes once again. 

"Alright my baby girl. Let's get you onto Mommy's change table and get your little bottom all wiped up". 

I reverted back to my soothing and caring Mommy tone. 

I put Tiffany on his back in diaper pose, with legs spread and in the air. I wiped and cleaned around his sissy pussy and applied baby powder to his locked up genitals. Next came a pink, crinkly diaper and a little baby girl top. 

With the additional padding that the diaper provides, it would be very difficult for him to feel any stimulation or sensation to his locked up little clitty. Exactly what I wanted, as I have some more devious plans for my naughty, baby girl. 

"Are you my little baby girl?" I cooed to him. 

I smacked the seat of his diaper, encouraging a quicker response. He nodded his head and whimpered out, "yes Mommy"...

Continued in: it was continued but Blogger deleted it.

Try this one: The elusive sissygasm

Mistress Andrea

xoxo

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