u/ChasteSissyBabyJeff

Image 1 — Rude misogynistic brat turned docile submissive sissy
Image 2 — Rude misogynistic brat turned docile submissive sissy
Image 3 — Rude misogynistic brat turned docile submissive sissy
▲ 515 r/ChasteDiaperedSissy+2 crossposts

Rude misogynistic brat turned docile submissive sissy

The package came with an assortment of sex toys of butt plugs, dildos, nipple clamps, paddle, leash, bondage set and a cute flat chastity cage which wife turned mommy uses on me after the delivery man left.

As soon as the front door closed I was dragged by my ear to the master bedroom where I was thrown on to the bed tied spread eagled, blindfolded and gagged. Mommy first used the paddle to spank my tushy bright red and raw before she uses her monstrous strap-on to pound and resize my virgin boipussy officially making me her sissy slut. When the delivery man come to our house again mommy invites him in and had me thank him for my transformation ever since then he have become my daddy and together with mommy will abuse/play with me or punish me when I’ve been a brat and I loved being spanked to tears so I am always being a naughty little brat

u/ChasteSissyBabyJeff — 6 days ago

Sissy public humiliating punishment

kidnaped and brought on to a yacht, have my little pee pee locked up in a flat chastity cage, hook butt plug stuffed deep inside my boipussy, put in a humiliating bondage position naked for the world to see while my captors took turns to spank my tushy as entertainment leaving me a crying moaning and whimpering mess

u/ChasteSissyBabyJeff — 7 days ago

Although I’m super embarrassed and trembling in fear but deep down I’m loving every second of this exposure, my tiny pee pee can’t stop straining in the Paci cage knowing mommy and her friends would want to take turns to spank my cute tushy bright red and raw before pounding my boipussy with their monstrous strap-on. The more I think of getting pounded like a sissy slut the more horny and aroused I get.

Mommy also has prepared a stack of 3 pink fluffy diapers along with stuffers on the bed. I will be sent to an early bedtime locked up,horny, frustrated, sore and diapered.

Knowing mommy she also likes to force me drink a big bottle of milk mixed with viagra and stuffing my boipussy with a very large powerful butt plug and have it set to the highest setting which will pound my sissy button making me squirm, whimpers, moan and hump my pillow or stuffies all night long by morning I would be waken up to a super soaked and sticky diapers awaiting mommy to change me but before doing so she would spank me extra hard for being such a naughty horny sissy gooner, she would also remind me why am I reduced to such pathetic state. ‘You’re such a pathetic chronic masturbator which is why you deserves to be a chaste and diapered virgin sissy your whole life’ mommy would chide and mock me in between spanks to both my tushy and swollen aching blue balls. After she is done spanking me raw and a crying mess she would make me lie down on the changing table, rubs icy hot all over my swollen purple orbs and bright red tushy she would diaper me up once again and the butt plug stayed buzzing in my boipussy. The spankings humiliation and the plug stimulating my prostate at the same time resulted in me immediately creaming my fresh diapers, mommy sees me having another sissygasm snapped and gave my crotch couple of very hard smacks then drag me by my ear to the timeout corner. ‘Stay there and don’t you dare move or the next spanking will be much worse you little sissy cry baby’ mommy shouts before storming out of my pink sissy nursery room leaving me sobbing and whimpering before another wave of sissygasm wash over me and let loose into my very much sticky diapers

u/ChasteSissyBabyJeff — 23 days ago
▲ 83 r/ChasteDiaperedSissy+1 crossposts

Not only does my roommate’s boyfriend who I have to call him daddy now makes me wear the humiliating cage but both him and mommy (roommate) loves to take turns to spank me LONG and HARD extremely hard when it’s daddy who spanks me. After they turned my tushy bright red and raw daddy would pick me up and throw me face down ass up on the bed tie me spread eagled, stuffs my penis shaped pacifier in my mouth and start pounding my boipussy raw sometimes mommy would join in the fun and use her monstrous strap-on and I would tremble, scream, yelp, whimpers and finally sissygasm but it will always leave me even more horny. After hours of raw pounding and daddy cums deep inside my boipussy they would diaper me in three layers of thick pink fluffy diapers before tucking me into my cucky crib with the baby monitor on so I would spend whole night turning and tossing listening to them fuck while all I could do is make humpies with the huge powerful butt plug daddy stuffed in me after filling me with his thick alpha cum buzzing away and smashing my sissy g spot,hoping to relief the ache in my balls, eventually my little pee pee would explode in yet another sissygasms and I would slowly fall asleep having wet dreams and multiple sissygasms. In the morning when Daddy or Mommy wakes me up my diapers would be soaked with lots of pee and cummies which will infuriate them resulting in me getting spanked on my still red sore tushy, in between the spanking Daddy or mummy depends on who is delivering the spanking would also randomly smacks my blue aching balls this would not stop until their palms grew tired. Such is a life of a sissy and I love every moment of it

u/ChasteSissyBabyJeff — 23 days ago