Embarrassing Questions for Sissies

[Chlorine]

Hey sissies,

I've got some fun questions for you, because I'm bored and find sissies funny (sometimes). Answer in as much detail as your pathetic selves can muster!

1. A kind benefactor has offered you an unlimited budget for a whole sissy outfit of your choice. The twist is that you will not be purchasing the outfit, they will be and the only way you can express your choice is by describing your dream outfit in as much detail as possible. Describe it.

2. Think about the last woman that you had sex with... (virgins, the last woman who you thought about while masturbating). Let's say they found out about your sissy ways. What do you fantasise about happening between the two of you?

3. The above question, but this time - what do you think would actually happen?

4. What female name would you give yourself? Why do you think that name suits you?

5. What is your favourite Taylor Swift album?

[darkness991]

Hey sissies,

I've got some fun questions for you, because I'm bored and find sissies funny (sometimes). Answer in as much detail as your pathetic selves can muster!

1. A kind benefactor has offered you an unlimited budget for a whole sissy outfit of your choice. The twist is that you will not be purchasing the outfit, they will be and the only way you can express your choice is by describing your dream outfit in as much detail as possible. Describe it.
most of the outfits i want i already have but if someone would pay for me id go with a perfectly fitting chastity cage, satin red thong with frills with bra, prostetic boobs, a black leather skirt that almost covers my ass, a black leather corset, a leather collar with sissy on it hold ups and black stiletto high heels with small openings on the side

2. Think about the last woman that you had sex with... (virgins, the last woman who you thought about while masturbating). Let's say they found out about your sissy ways. What do you fantasise about happening between the two of you?
hehe well thats my gf and she knows about it and yes we do what i like sometimes im even locked in chastity for her at the moment and im hoping she will fuck me with a strapon tonight while dressed in my sissy clothes and then she keeps me locked even after fucking me

3. The above question, but this time - what do you think would actually happen?
i think she will be to tired and ill have to please myself while still locked or she does fuck me and lets me out to cum

4. What female name would you give yourself? Why do you think that name suits you?
iv been given a sissy name a long time ago since my name is tom he called me tania

5. What is your favourite Taylor Swift album?
i dont listen to her i did put on her songs now to see what could be fun but its not really my kind of music

[beof95]

1. A kind benefactor has offered you an unlimited budget for a whole sissy outfit of your choice. The twist is that you will not be purchasing the outfit, they will be and the only way you can express your choice is by describing your dream outfit in as much detail as possible. Describe it.
Pink sexy French maid outfit with a short but wide skirt with many layers and lots of frills. A white frilly bra, white frilly see-through panties, white garter belt with white stockings. Pink 9 inch high heels that are locked with pink heart pad locks. white frilly gloves and a silver tiara.

2. Think about the last woman that you had sex with... (virgins, the last woman who you thought about while masturbating). Let's say they found out about your sissy ways. What do you fantasise about happening between the two of you?
She turns me into her sissy cuckold maid slave.

3. The above question, but this time - what do you think would actually happen?
She would freak out, laugh, scream and then just leave degusted.

4. What female name would you give yourself? Why do you think that name suits you?
Thinkerbell. Don't know, I just always liked it.

5. What is your favourite Taylor Swift album?
1989

[alex_af1996]

Hey sissies,

I've got some fun questions for you, because I'm bored and find sissies funny (sometimes). Answer in as much detail as your pathetic selves can muster!

1. A kind benefactor has offered you an unlimited budget for a whole sissy outfit of your choice. The twist is that you will not be purchasing the outfit, they will be and the only way you can express your choice is by describing your dream outfit in as much detail as possible. Describe it.
I would describe it as a chequered squirt that was just long enough to cover my cock, long white socks of Lacey socks held up by straps, a crutch less one piece underwear to go underneath (white or red), top half a white shirt that was tied up to show my stomach and to finish it off red lipstick

2. Think about the last woman that you had sex with... (virgins, the last woman who you thought about while masturbating). Let's say they found out about your sissy ways. What do you fantasise about happening between the two of you?
I wish she would dress me up and fuck my holes like a sissy

3. The above question, but this time - what do you think would actually happen?
She wouldn’t do anything


4. What female name would you give yourself? Why do you think that name suits you?
Alexa because Alexa does what she is told

5. What is your favourite Taylor Swift album?
All of them

[MissyK]

I can't answer it for myself, but I'd love to see more answers so bump!

[chiefsfan]

1. A white blouse with a black mini skirt. Underneath I would want a black lace corset with a matching thong garter belt and stockings.

2. She knows about it and I fantasize about serving her all dressed up 24/7 while she fucks who she wants.

3. Nothing happens. I dress up occasionally and she plays along

4. I don’t know. I’ve thought about it but never settled on one

5. Reputation or 1989