Theme(s) of the Month!!! Crossdressers, ladyboys, sissies & Bimbo TG

Somewhat more humorous one that I reckon could fit in to one picture. We see the aftermath of a clerical error where one person has received some magic clothing that's turned them into a bimbo (looking fairly shocked) and the other has just received some normal clothing (leaving them wearing the clothing, still the same as usual and likely disgruntled). Manages to tick both theme boxes, and I think it would be nice for a nice bit of lighthearted humour.

Crazy sam10

i change mine lol Robin from teen titans gets caught touching starfires outfit, so she uses some magic and make it fit better than he hoped (not that he wanted to of course ;D )

Kayden of Course

but they did already lmao

Kayden of Course

A sister finds her step brother stealing from her moms purse and soon blackmails herself a sissy maid to pay the debts

Maybe something where he cosplay as a female like Riku oryuns from final fantasy 10-2

Guy walking home hears something going on, witnesses a man being transformed but accidently interrupts them. They take him instead and after it's done he thinks to fight back but soon realizes he isn't fighting anymore.

I did have an idea the other day for a Zelda-related TGTF based on the new game, where Link sneaks into Gerudo Town disguised as a girl, and upon getting caught is cursed to turn into a proper Gerudo maiden.

ZBL

Link trying to sneak into gerudo village by dressing himself up in traditional gerudo female clothing so they mistake him for a female, but he actually becomes female under the clothes. Or he could just be cross dressing and caught by gannon. Edit* Made into gannons sissy boy for example.

Thorval

A husband being turned into a sissy by his wife for first time!

Kyle

A girl catches her boyfriend trying on her clothes, and decides to continue the dressing-up rather further than he had intended...

Martin Lock

(Bonus points if he's still aware of the changes even as a bimbo, but has to make due with the circumstances while resisting how much he's enjoying it.)

ZBL

In futuristic setting, a worker on a space cruiseship has his consciousness transferred to an android body to do job. Due to a glitch with the ship's AI navigator, he's registered as female and is employed in female occupations, and is slowly feminized/bimbofied as his/her chassis is upgraded based on guest feedback/complaints. For example, Facial Modification to give off a friendly appearance. Feet get replaced with heels, and leg exchange enforces a sway. Hips widen/bust fills out for the purpose of being able to act as a lifeguard from buoyancy. Firmware results in an accent/dialect, and censors out attempts to correct identity/gender. A euphoric response is supplied for fulfilling tasks, rewarding the feminization. I call it: Theseus's Cruiseship.

ZBL

Male gets forced in convincing crossdress and is made to sit at a glory hole or be an escort

A guy gets caught crossdressing by his roomate(s) and initially he feels embarrassed but then they both kiss and one thing leads to another...

A crossdresser is given an enchanted balloon by a mysterious old woman who sells enchanted objects. When blown up, it's shaped like a human. A poke to the belly makes the breasts pop out. Then his own belly twitches, and ZIP! His belly shrinks, and breasts pop out of his chest. The more he pokes it, the more the proportions change (shrink here, grow there) until he has the prefect feminine body he always wanted. (This is from a certain anime that I never found out the name of. Unlike the anime, I wouldn't want the crossdresser to start out overweight [no offense to anyone]. I'd like him to be sexy beforehand.) (Yes, this is kind of a long sequence. I'm kinda bad about that. A shorter version is fine.)

mckthomp

Crossdressing CW DC superheroes. I.e. Crossdressing Flash, green arrow, legends of tomorrow.

Sorority Girls forcibly crossdress a panty raiding Frat Boy!!

Devin Dickie

I suggest 9S as a bimbo since it is conducive story wise...

RenewReturner

:D what about a look into the transformation of Sanji (from one piece for those who dont know) when he was on new kama island! like either him getting dolled up or caught trying ivankov's clothes!

Kayden of Course

I love sissy art. How about a mother or older sister dresses a boy in a Cute Princess dress with lace and petticoats, like Princess Peach or Belle from Beauty and the Beast (animated version) And the boy has to love being pretty :)

AzureAKASapphire

A guy tries latex on and becomes a girl! (Almost ZOAT but more real world)

SheIsInTheMirror

A wife crossdresses her husband, but that causes him to become a bimbo. Maybe?

danielsangeo