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u/ChubbySissyJean

r/Sissy r/AISissyHentai r/AISissyHardcore r/FemboyHent_AI r/rule34aiart r/chastity r/sissyology r/SissiesWorldCaptions r/SexToys r/chastitytraining
▲ 53 r/AISissyHentai

Petra Parker aka Spider-Woman Re post!

Decided to repost Petra with a larger X-Ray of her chastity cage to make it easier to see the chastity cage.

u/ChubbySissyJean — 2 days ago
▲ 31 r/sissyology

Wearing a chastity cage to work?

I’m curious to hear from sissies who have gone to work wearing their chastity cages. What sort of cage do you wear? How do you feel when wearing the chastity cage? Have you done it again or do you wear it as part of your daily routine?

reddit.com
u/ChubbySissyJean — 4 days ago
▲ 5 r/chastitytraining

Chastity cages for discretion?

So, I’m looking into chastity cages and I’m hoping to get some advice on ones that are good for discretion/can be easily concealed beneath clothing.

Like what is a good type of chastity cage that can be worn under your clothing to a 9-5 office job that won’t make much noise or clink around too much if you have metal one?

reddit.com
u/ChubbySissyJean — 4 days ago
▲ 89 r/AISissyHentai

Created my own custom Sissy Persona!

I’m open to making custom ones as well if anyone would like a custom made sissy persona brought to life?

u/ChubbySissyJean — 8 days ago
▲ 1 r/chastitytraining

Flat catheter chastity cages?

I recently bought myself a flat chastity cage and a series of catheters of varying sizes that can screw into the main drain hole of the flat chastity cage. I tried it on with a medium sized catheter (83 mm total length), and I found that when I tried urinating through the catheter, I felt a strong pressure that didn’t quite let me pee easily.

Am I doing something wrong or putting the catheter in incorrectly? I could really use some advice on being able to pee through the catheter easily and without much pressure and pain. Is it something I need to work up to? Do I need to get a catheter with a wider tube to allow urine to flow through easier?

What should I do?

reddit.com
u/ChubbySissyJean — 10 days ago
▲ 173 r/AISissyHentai+1 crossposts

Sissy Hypno Careers! Which sissy career is your dream to be hypnotized and feminized into?

HOSPITAL NURSE
A NIGHT-SHIFT NURSE IN A PRIVATE CLINIC WHO “CHECKS VITALS” BY DROPPING TO HER KNEES BETWEEN ROUNDS. SHE SPECIALIZES IN ORAL “MEDICATION,” LETTING DOCTORS AND SELECT PATIENTS USE HER MOUTH WHILE SHE KEEPS THE STETHOSCOPE ON AND THE SKIRT RIDDEN UP.
FULL-TIME, ROTATING NIGHTS.
SALARY: $145K

EXECUTIVE SECRETARY
A HIGH-RISE OFFICE SECRETARY WHO TAKES DICTATION WITH HER LIPS INSTEAD OF A KEYBOARD. AFTER HOURS SHE SPREADS ON THE DESK FOR PARTNERS AND CLIENTS, KEEPING HER GOLD THONG PULLED ASIDE WHILE SHE FILES REPORTS WITH A MOUTH FULL.
YEAR-ROUND, FLEXIBLE OVERTIME.
SALARY: $160K

PRIVATE SCHOOL TEACHER
A CLASSROOM TEACHER WHO GIVES “EXTRA CREDIT” AFTER THE BELL. SHE BENDS OVER THE DESK, SKIRT FLIPPED UP, AND LETS FAVORED STUDENTS OR PARENTS USE HER THROAT WHILE SHE STILL HOLDS THE POINTER. DISCIPLINE IS STRICT—AND WET.
SCHOOL YEAR PLUS SUMMER TUTORING.
SALARY: $125K

DINER WAITRESS
A LATE-NIGHT DINER WAITRESS WHO SERVES MORE THAN MILKSHAKES. SHE LEANS OVER BOOTHS, APRON FLIPPED, AND TAKES ORDERS WITH HER MOUTH UNDER THE TABLE WHILE THE NEON GLOWS. REGULARS KNOW TO TIP HER DIRECTLY BETWEEN HER LIPS.
GRAVEYARD SHIFTS, YEAR-ROUND.
SALARY: $95K (plus heavy tips)

LUXURY HOTEL MAID
A PENTHOUSE MAID WHO CLEANS ROOMS ON HER KNEES. SHE KEEPS THE FEATHER DUSTER BETWEEN HER TEETH WHILE GUESTS USE HER MOUTH OR BEND HER OVER THE BED. THE KEY ON HER CHOKER OPENS MORE THAN JUST THE MINIBAR.
FULL-TIME, HIGH-END HOTEL.
SALARY: $110K
BEACH LIFEGUARD

A COASTAL LIFEGUARD WHO “RESCUES” MORE THAN SWIMMERS. SHE SPREADS ON THE TOWER OR IN THE SAND, RED SWIMSUIT PULLED ASIDE, AND GIVES ORAL CPR TO ANYONE WHO WHISTLES FOR HER. THE BELT POUCHES HOLD LUBE INSTEAD OF FIRST-AID.
SEASONAL PEAK + YEAR-ROUND PRIVATE BEACH CONTRACTS.
SALARY: $105K

u/ChubbySissyJean — 12 days ago
▲ 298 r/AISissyHentai

Would you rather be a sissy femboy maid at a sissy maid cafe, a sissy playboy bunny girl at a casino, or a sissy stripper at a freeuse sissy strip club?

In each scenario, you would start off by wearing a special AR visor and headphones that play sissy hypnosis audio and fills your AR visor with hypnotic flashes and suggestions. You would also slowly be feminized more and more over time.

u/ChubbySissyJean — 13 days ago
▲ 9 r/chastitytraining

Building up chastity duration?

So, I’m trying to set myself up with a plan for increasing my time in chastity.

My current plan is to wear the chastity cage for one day then give myself a two week cool off. After two weeks, I wear the cage for two days. After another two weeks, I add another day, and so on and so forth.

Once I am comfortable wear the cage for two weeks long I begin to reduce the time I’m out of chastity by one day, sort doing the inverse of how I started.

This is my plan, but I’d like to hear how other people have built up time in their own chastity cages. How did you plan it and how did you ensure you remained locked up in chastity?

reddit.com
u/ChubbySissyJean — 18 days ago