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Sissy Questionnaire - One
Written by Mistress Emily   

Sissy Questionnaire 1 - Completed 

Are you in a relationship with anyone?


Do they know that you are interested in wearing ladies underwear?

No. I have joked about it, but she doesn’t know

How would you describe yourself?

I’m straight, but possibly still bi-curious. I’m not too sure

How long have you been wearing feminine underwear?

Over five years

How did it first start?

I really liked sexy female underwear and just longed to try it. When I did work experience at a department store, they had spare unaccounted thongs and g-strings just left in the warehouse, so I had lots of opportunities to take some, which I did. I remember putting on my first pair. It was a bright pink, girly g-string. I slipped it up my smooth young legs and it felt so good! I remember taking them off and keep putting them back on because I loved how sexy they made me feel!

How often do you wear feminine underwear?

I haven’t worn them in ages! I joined this site to get back into it, but I would wear them about once a week.

How many hours per day?

I’d wear them for up to 4 hours I think, then change back into normal underwear for the rest of the day, but sometimes I would sleep in them.

Where do you wear feminine underwear?

At home, a couple of times I have worn them out

How often do you wear feminine clothing?

When I wore them, I would try to wear them at least once a week

How many hours per day?

I’d just wear them for maybe an hour

Have you ever worn feminine clothing outside?

No, just underwear

Do you wear feminine clothing to bed?



Have you ever worn makeup?

Yes, I have

How many days a week do you wear makeup?

Just when I would dress up, so once a week

How many hours per day?

I’d apply it, take some pictures (which are now gone) then remove it before my family got back

Do you paint your fingernails?

Once before

Do you paint your toenails?

Never done it


How many days a week do you masturbate?

I usually masturbate everyday, so 6-7 days

How many times per day?

1, sometimes 2 but normally 1

Do you “dress up” when masturbating?

Yes, about 50/50 when I used to dress up


Have you ever shaved any of your body apart from your face?

Yes, I have shaved my ass, and legs but because I have fair body hair its not really necessary. And yes, I’d like to again

Have you ever penetrated your anus?

Yes, I have used a butt plug, and would love to do it again!

Have you ever tasted your own sperm?

No, its never interested me, and I don’t think I’d like to


What is you favourite sexual fantasy?

Being sold into sexual slavery has always been a big fantasy. Made up like a cheap hooker, red lipstick, mascara, big fake breasts, wearing a school-girl outfit: tiny low-cut white blouse, extra extra short plaid skirt that shows a lot of ass, white frilly ankle socks and mary jane heels, blonde hair put into pigtails. I’d be collared and led onto a stage with a leash, and forced to parade around showing my sexy body off, and being humiliated. Powerful black men would be buying me. Once they have, I’d be forced to crawl on all fours into the boot of their car, and taken to their home. They would make me do sissy tasks, and tie me up when ‘not in use’, like hogtying and ball gagging. Lots of kinky bondage gear, like dildo gag, butt plugs, anything that would humiliate and degrade me.

They would make me their little sissy bitch. I would have to suck their big black cocks whenever they felt like it, get bent over and fucked, spit-roasted, and lots of spankings, over then knee. They would also pimp me out, making me show myself off on street corners, and go and fuck and suck in the alleyways.

So basically being owned as a white sissy sex slave and whore, forced into humiliating things and constantly reminded of my place with lots of dirty talk, drinking from a dog bowl, licking up cum from a dog bowl, sleeping in a kennel, being caged, forced to dance and perform, walked like a dog, molested, raped, any dirty, naughty kinky things. In every one of these scenarios, I am always made up like a girl, full makeup and hair, but being degraded like a proper slut. The porn I watch is like teen girls being told what to do and dominated, I like to imagine I am those girls when masturbating to it basically.

I also have a massive fantasy about being feminized by a sexy, strong woman of course. Like being emasculated, forced to dress up like a slut barby doll, trying on a variety of outfits/uniforms like school girl, maid, nurse etc etc, made to suck a dildo, and be fucked by a strap-on dildo, parading around outside and humiliated, my mistress allowing strangers to take advantage of me, being tied up and gagged in various positions. And of course, being pimped out in dirty places like public toilets (I really am a dirty tart lol)

I love being called a variety of names like slut, whore, bitch, tart, trollop, tramp, sissy slut, cock sucker, fuck toy, cum dumpster.

But overall, I just love being all girly and femme, but also being really submissive and slutty, doing anything a sex partner wants and being humiliated and degraded as a girl rather than a boy

Is there anything else that you would like to share with me?

Well, I thought I was bisexual, because I have always fancied and loved girls, never boys. But I recently wanted sex with a man, but I could never have a relationship with one, that’s how I feel. I figured I need to find out whether I was bi or not, so I met up with a guy, and had sex with him, me as the submissive, collared and leashed. I sucked his cock and he fucked my ass, but I didn’t particularly enjoy it. I loved being spanked however, and having my panties pulled down.

So I realised I was straight. I might like to try sex with a man again, but only if I’m fully tarted out, and took a bigger cock. But I’m not too sure, someone once told me that fantasies are best left as fantasies, and I had sex with a guy because I just needed to get it out of my system. I think you should try what you like when you’re young, rather than start late. Personally I don’t like the idea of middle aged men dressing up as women, but of course that’s their choice. That’s why I am doing it now, so I can relax when I’m older knowing I have no regrets. Overall, the whole sex with a guy/dress up slut thing is purely a sexual thing. it’s a fetish I love, but its not a lifestyle for me. I love my Rania, and I know she loves me, but I need this as well. I’ve moved back onto being dominated by/dominating a woman after I had sex with a man.

I hope you understand Mistress Emily, I’m sure you do as you work in this industry. Everybody has a fetish, its part of being human. it’s the ones that try to hide and deny it that will end up hurting themselves. And this actually felt good, typing it all out, so thank you! I have trained with a mistress by email before, but she wasn’t that supportive, you seem so much better!

Some of this info might be contradictory, but I just wrote out what I thought, and its all there.

Hope you had fun reading this.