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Q.1
I am going to the adult theater dessed as a sissy. Should I go anywhere else before that?
Go directly to the adult store, so I do not chicken out again
Adult Toy store for a black suction cup dildo to practice with
Adult Toy store for a Penis Pump for my little clit
Adult Toy store for a new blowup doll to use after I complete my task.
Victoria Secret for new panties and have to admit are for me.
Department Store to shop for women's clothing and try on a few things.
Drug Store for lube and condoms (already have enough, just for the shame)
Other:
Q.2
Do I have to place a personal ad at least a day before I go?
Yes
No
Q.3
Before heading out for my assignment should I take my Viagra?
Yes... It will only frustrate me more while locked tight in chastity
No..... I will already be humiliated enough at what I have to do and 18 days without an orgasm is enough frustration without the Viagra
Other:
Q.4
What outfit should I wear to the adult theater to complete my task?
Dressed as before when I failed to go inside. (Mistress had actually requested some kind of easy access comfy pants, but they had to be sissy) Cute pink lounge pants and cami (like college girl lounge attire). Thin show panty line and chastity cage outline. With cute little sandals and black embroidered zip hoody.
Tight girl jeans and cute tight top (probably embroidered and jeweled jeans and a pink shirt (or My Hello Kitty one or "I Like Boys" tank)
Long cotton summer dress with cute heels and stockings
Short black dress (one of my new ones), stockings, panties and bra (all in black)
Denim mini skirt with cute cami and sheer top, stocking and cute heels.
Pleated plaid mini skirt cute button up top, stocking or knee high socks, and cute shoes
Other:
Q.5
What wig should I wear?
Blonde shoulder length wig (with highlights)
Blonde long wig
Brunette long wig
Q.6
What hairstyle should my wig be in?
Styled as wig came
Ponytail (to keep hair out of face when sucking)
Sissy Pigtails
Other:
Q.7
What should my mood be when I enter the theater?
Completely Sober so I feel the complete shame of what I am doing, but most chance to chicken out
A couple drinks to take edge off
A couple drinks and and additional one between each Blowjob to give me courage to continue.
Very typsy, so I am a willing and less inhibited
Other:
Q.8
How many men do I have to pleasure orally?
One
Two (Mistresses preferred minimum and cum must be swallowed)
Three
Five
Other:
Q.9
Will I be allowed and orgasm after I complete my task?
Yes
No
Q.10
If I am allowed an orgasm. How should it happen?
Masturbation
No Orgasm
Anal Stimulation
Contact local girl in an ad to do it as a special reward for first time (how a release occurs is up to her, have not had a BJ or intercourse in so long)
Contact a local mistress I have seen before for more humiliation (how and if a release happens up to her)
Mount and have sex with one of my Blowup Dolls
Other:
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