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