The Emasculation of Sissy Daisy

For starters walking to the door and seeing Your note and the clothes laid out immediately set my head spinning. i had never done anything more than wear panties, so being dressed up was an extremely humiliating experience for me. i felt both incredibly excited and deeply humiliated. i immediately felt emasculated and ashamed, especially in combination with my little cock being locked up. The most intense part was putting the lipstick on. It felt like there was no going back once the lipstick touched my lips. It made me feel weak and foolish.

i know many crossdressers enjoy the feeling and sensation. For me it was utterly humiliating. There was nothing pleasurable about it, just feeling foolish and ashamed and like i was no longer a man.

In my head, i was thinking, “i deserve this because my cock is too small to please a woman” and that this was the only way You would ever want to be around me, that i would have to humiliate myself this way to earn even a small amount of Your attention. My cock is straining in its cage, as i write these words to You.

taped the tree, i went to a very, submissive place
When You taped me to the tree and took pictures of me, i went to a very submissive place. i felt like a toy or a dress up doll for You to play with. My emotional masochism started to creep in and i was flooded with feelings of You seeing me that way, knowing i could never go back to being anything other than a sissy in Your eyes.

The feelings also tapped my craving for denial. Not just orgasm control, but being denied my masculinity. Having that taken away so quickly and so completely made my head spin. i saw You posted a picture on Twitter, which made my shame even deeper. i remember how aware i was of the lipstick on my lips and how absolutely humiliated it made me feel. i also had a flashback to one of my earliest SM fantasies. i remembered wishing as a boy that i was kidnapped by a group of girls from school and given a makeover by them at a sleepover party. If i didn’t follow every instruction exactly they would punish me. i imagined them putting make up on me and dressing me up and making me model things for them, while they made fun of me, That was when i was in the 7th or 8th grade. i was always developing crushes on the “mean girls.”
Coming inside and

lick up, chewed chips and soda off the floor
eating Your spit out food off the floor was incredibly powerful as well. It truly made me feel like i was lowering myself in front of You. How could You ever have any respect for someone who would lick chewed up chips and soda off the floor? and i couldn’t even do it right. i was terrified, i would get lipstick marks on your floor. It was very humiliating for me.

The spanking was extremely intense. i wanted to please you so much. i also have very deep shame, about masturbation. The whole punishment, especially having to admit to it, pushed a lot of my buttons. While i was driving home, i imagined what it would feel like, to have to, stand in front of You, maybe in a pretty dress and have You scold me about my masturbation problem. Digging in to me and really making it hurt. Even talking about it like We/we did, triggered very deep humiliation.

So i suck on it…i sucked, like a pathetic bound & milked sissy
The pain level of the spankings was very intense for me, but it was exactly what i needed. It truly felt like punishment for my masturbation, not a game. It felt like discipline and i won’t be able to touch myself, without thinking about that and those feelings. i truly wish, as hard as it would be on me, that i could have my masturbation both controlled and used as a source of humiliation on a long term basis.

And then the medical room. i barely have words to explain how deeply submissive, humiliated and exposed i felt.

knees open & ass exposed, i felt shameful Very close to tears
Having my knees open and my ass exposed was extremely shameful and i loved the tight bondage. i felt so helpless, so weak, so vulnerable. When You stuck the dildo in my mouth, i was very close to tears.
Probably the most intense moment of the whole day was when You stuffed the paper towel, with my cum on it, in my mouth, At that moment, i felt so ashamed and humiliated, i thought i might not be able to, look You in the eye after. i can’t even imagine how You see me after that. It was bad enough at first and i thought i could get through it, but when You demanded that i suck on it and clean it,
the humiliation hit me, like a tidal wave
it all hit me like a tidal wave.

When You threatened to hurt me, if i didn’t obey, i have never felt, more helpless and controlled. i started to suck on the paper towel, wanting so desperately to clean it for You, not out of fear of punishment, but because in that moment, i wanted You to know, i would do something so gross, so horrible, and so humiliating for You, for no other reason than because You told me to. my discomfort was less important, than obeying You.

So i suck on it, i suck on it like a pathetic, bound and milked sissy, who in that moment worshipped and adored You. The more i sucked and licked, the more i felt that You would never see me as anything other than a sissy, to humiliate and to torment. i could feel my self-esteem, pride, and self-worth slipping away. But i still kept, sucking on it.

As i write all of this, i am straining in my cage. i feel like that is, what i am supposed to do now. Those are some initial reflections and some insight into what was going through my mind.

Thank You again Mistress Victoria, for a wonderful day and for dressing me up and helping me find my sissy self.

as i write this, i’m straining in my cage

The Emasculation of Sissy Daisy