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My next sketch stream will be on Saturday, May 1st at 4PM.

This month's theme is Pin-Ups!

Bring me your suggestions for pin-up outfits. These will be simple, one-character pin-ups so I'm only looking for the outfit you want to see, not any complex backstory. Like something you might see in a pin-up calendar.

I chose this because there are some outfits that it's harder to think of a good backstory to justify so I wanted to be able to draw any outfit without having to worry about a backstory for a chance.

Since I'm only looking for outfit ideas, please feel free to be very specific and detailed about your outfit ideas. If I choose yours, my interpretation may vary but I'll try to stick as close to the description as I can.

I will post the URL for the stream when I am ready to start. If you won't be able to join me, I encourage you to post a suggestion as a comment on this post.

Comments

WedgeFel

I would absolutely love to see a pinup of a ballerina. But I literally am always gonna suggest that haha And a sexy sailor pinup. High waisted shorts, shirt with the sailor collar, medium ringed curls for the hairstyle, a little sailor cap, great big nails, a lot of red white and blue

Anonymous

My idea is a guy hypnotized into taking pin up photos in different outfits for a calendar? Maybe his wife/gf and some of her friends get in on the action

Connar Woodhead

A pin-up for the Army, Navy, Air Firce, etc. "Service Your Country, One Way OR Another"

WedgeFel

I would love a beach themed pinup. A poor embarrassed sissy in a bikini trying to strategically hide the bulge during the photoshoot but failing. Or maybe a sexy life guard sissy posing heroically. You just know she’s ready to give mouth to mouth to any hunk who needs it to save the day.

Andrew

I have 2 ideas. A sissy in foundation garments with a rack of costumes, maybe holding up a dress to their chest. A sissy infomercial host to one of the myriad kinky store settings about to display some bondage gear or new sextoys.

Anonymous

I'd love to see a sissy in the style of the iconic Bettie Page! The vintage lingerie (high-waist panties, pointy brassiere, sheer thigh-highs) and heels, thrown together with some willing/unwilling bondage modelling. And the whole thing would be in black and white of course ;)

Marylou_76fr

A cabaret style pin up with a dress that has a red corset / bustier with black lines (maybe the possibility of black lace on the bustier) and a kind of black rose in the middle of the bustier (middle / under the breasts), this dress will be composed of the bustier and at the bottom of a tutu / petticoat made of black tulle well filled, Long or short black tights that can be attached with a garter belt, black stiletto heels or black boots / small leather boots. A black necklace with a flower, long curly hair or long hair tied, a red or black hat or the boths colors with feathers and others ornaments / decorations (frilly style). Alternative outfit, we stay on the cabaret style, a red bustier with transparent and opaque parts (a transparent part in the shape of a triangle / heart can be at the level of the breasts with a pretty black bow), A red panty with black lace edges. Long or short black tights that can be attached with a garter belt, black stilettos or black leather boots. A transparent black vest / bolero with long sleeves. A black necklace with a flower, long curly hair or long hair tied. A red or black hat or the boths colors with feathers and others ornaments / decorations (frilly style).

Eelco

Maybe a sissy wearing a long fur coat, held open, showing a metal bra and a metal chastity belt?

Phillip Kettless

CanCan girls or maybe a take on a Gilgren piece of art

Anonymous

What about a Sailor uniform? But sissify it a bit~ and big fake boobs~

Anonymous

A great opportunity for a new "almost caught" or "about to get caught" pic. Where the sissy is fully dressed or still in underwear and he hears his wife calling for him or hears the front door open or foot steps coming towards the room. reference https://mwbbcwxck32zpp124d9nlwip-wpengine.netdna-ssl.com/wp-content/uploads/2018/11/1221748.jpg A sexy model showing off a new line of prom dresses, sexy, frilly, sparkling, silky, lacey, sequin, fluffy, furry, leathery and velour. They can be very long, long, short, very short, medium length, all kinds of tops tube, halter, batwing, spaghetti, sleeveless, singlet, etc. With sexy matching heels and big hair and a nice pair of big boobs and hips. Your sexy lingerie pin up like (artist) Bill Ward style. The sexy baker who is only wearing the apron and baker hat with a big cake. from a rear view showing his sexy butt and legs. The cutesy accident pin up where the the sissy is naked covering his sexy parts with a look of happy surprise like "oh no you caught me with my panties down hehehehe." Another accident where the sissies dress gets caught on the car door and half of it rips off and his boobs all exposed and has a shocked but whoopsie expression like "gasp" "oh no" reference https://www.greatbigcanvas.com/view/laundry-pin-up-girl,2371840/ Husband admiring his wifes' sunday best dress with sun hat and sexy heels in front of the mirror. Sexy mechanic pin up Sexy goth (elvira mistress on the dark or morticia addams or vampira or lily munster style)

Scottie Wottie

Bo Peep with a ruffled bonnet and bell-shaped skirt which is too short to hide her panties when she bends over

Scottie Wottie

A fluffy bunny onesie: hood with big floppy ears and golden curls spilling out, button-up front partially open, long sleeves, snug booty-hugging bottom with big tail, thigh high socks, maybe rabbit foot slippers or big chunky heels

Anonymous

Something in the realm and style of your rockabilly pieces could be cool.

Phillip Kettless

Just had a thought. How about a poster in the theme of the first world war with a dominant mistress in a short leather skirt and white blouse with black thigh high leather boots pointing out of the poster towards the viewer with two bound (armbinders) two ring gagged sissies either side of her with the banner "We Need More Sissies!"

Phillip Kettless

Could also be "I Need More Sissies!" or "The World Needs More Sissies!"