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I dressed up as a girl last Halloween and was walking home drunk when I noticed a huge house party. A few older men were out front and starting to whistle and call me sexy, I wasn’t sure if they were teasing me but I was on 6 months of hormone treat

The slutty school girl outfits were just a joke. Casey and Marissa planned to spend the Halloween party acting like caricatures of the girls who constantly flirted with the guys on campus. They even brought their own drinks so no one would slip them anyth

Halloween is just an excuse to be a slut.

“Sorry but we only fuck black cowboys”

You’ve watched one to many Hollywood movies loser…

I hope some nerd with a big dick hits on me tonight.

Think superman will shoot his load on my boobies?

You’ll be eating black cum out of Pocahontas’s pussy…

My boyfriend gave me a free pass this Halloween.

caption sucks but this halloween milf is beautiful

Happy halloween, sissy.Ready to dress up?

Halloween: Another holiday that gets way too much bad press in the crossdressing community. Just because all the crossdressing antics that usually condemn CD'ers to be stuck like girls for the rest of their life usually occur on Halloween doesn’t

Halloween: What are you dressing up as this year, first-timers? Start planning now so it’ll be the perfect night that you’ll never forget.

Halloween: the gateway to self-feminization.

Peter!? Verdammt! Hi… Schatz! Warum trägst du meine Sachen? Ähm? Ich wollte es nur mal probieren wie es aussieht, wenn ich mich zu Halloween wie ein Mädchen verkleide? Oh, cool! Aber warum schleichst dann so früh hier draußen rum? Ähm. Ich wollte

salemtheblackcat: Happy Halloween! I’m a spice rack. don’t remove caption or you will be cursed with an unsuccessful harvest.

Cassie blushed as she squirmed into the tight costume. She had been to a couple Halloween parties before, but she hadn’t ever dared to go as something “slutty,” her body just wasn’t right for it. You know how it is, there are slutty nurses, slutty

Candice Swanepoel — It’s not Halloween anymore but I still had these pictures and wanted to do something with them!

It’s October and that means sexy costumes! I’ve been busy IRL but I’m working on a Halloween Week series to start next week. Here’s some Candice from last year to tide you over.

vsfemdomcaptions: Officer Candice Swanepoel owns you Halloween is coming…

vsfemdomcaptions: Candice wants to play a game. Halloween Week is almost here…

Halloween Series: Goddess Elsa is the sexy slave maid of her new Alpha Master, and so are you!

Halloween Week: Goddess Alessandra teases you in public as Jessica Rabbit

Halloween Week: Join the Mile High Edge Club with Stewardess Candice

Halloween Week: Goddess Miranda performs a magic trick with her special assistant

Halloween Week: Candice the Godmother demands her (key) protection payments on time

Halloween Week: Goddess Elsa want you to worship her ass

Halloween Week: Captain Candice welcomes the new recruits to the Femdom Navy

Yes, I’m doing a caption with Candice in the devil costume.

Halloween Week Finale: The Devil Candice wants your soul in exchange for an eternity of teasing and edging. Do you take her deal?

Hi could you do something with this picture in your halloween´s week?? She as a girl with childish personality and a poor nerd boyfriend sufferin in chastity for years? thanks!!

I know I’m late and I know most people are gonna skip this due to its overboarding length… but here’s my cruel caption for Halloween!

Halloween Forced Feminization Caption – The Help

Halloween TG Caption – Too Much? Continuing the Halloween-themed captions…

Halloween Sissy Caption – Definitely the Bow

Halloween Crossdressing Caption – Catwoman

Halloween Crossdressing Caption – Tinkerbell

Halloween Sissy Caption – A Sissy Waitress At Halloween

Crossdressing Caption – Late Halloween

Halloween Caption - A Bet’s a Bet

Halloween Caption - Fitting

Halloween Caption - Fitting In

Happy Halloween! For those of us who gravitate toward this genre of fiction (and those who live it as reality), Halloween is something of a special holiday. For many, it’s the one night of the year when it’s socially acceptable to venture

Halloween Crossdressing Caption - Costume Party

mysweetbabydollsarah: I’m a cheeky witch ⃛(❛ั◡˜๑) ~Spoil me~ ||Please do not repost or delete my caption. ||

nailbats: Heeeey it’s halloween, so have some Battle Tendency x Haunted House?? (ref; 1, 2, 3) clickthrough for lame captions.

malacandrax: A bunch of requests and misc sketches from this weekend! (I’ll probably work on the requests y’all sent in every now and again, its nice to have a sketch to go with my ask responses and stuff :P) Check the captions! The last image is

She plans on breaking this little number out for all of those costume parties you two get invited to all the time. You’ll be seeing it a lot more than just on Halloween…

pekoeboo: I’m gonna burn my house down into an ugly blackI’m gonna run away now and never look back [x] (Please do not remove caption or repost. also on deviantart)

pekoeboo: I’m gonna burn my house down into an ugly blackI’m gonna run away now and never look back [x] (Please do not remove caption or repost. also on deviantart)

hentaibeats: Halloween Set Day 2/20!(ﾉ◕ヮ◕)ﾉ*:･ﾟ✧ All art is sourced via caption! ✧ﾟ･: *ヽ(◕ヮ◕ヽ)Click here for more hentai! Click here for more daily halloween! Click here to read the FAQ and Rules before requesting! Feel

anon0w0stories: “And another goodie bag for me <3 I love Halloween night, everyone thinks I’m just a slutty girl, all I have to do is show them my breasts and they’re all over me. How many does this make, 13? Hehe it’s only 8:30, the night

crr3483: Filled Out (Halloween Caption)

chastity-slaves-obey:Halloween Week

charmaise: Happy Halloween! (captions if you dont know a costume!) i have no idea where this was going and im super early but i want to post this incase im not motivated on the week leading to halloween, so enjoy this 2spooky really long comic.

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