Sissy quiz!! Questions answered Dec 2022

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1. When you check out hot girls tell me what you look at other than the obvious. (ie. Jewelry, shoes, outfit, hair, make up etc.)?
I don't have a hardcore foot fetish, but I do love looking at women's feet. So, one of the first things I notice are a woman's feet and the sexy, cool shoes she is wearing. I have several pairs of women's shoes, but I fantasize about having a closet full of sexy shoes. I could walk around naked just wearing women's shoes. Outfits are my next passion. Girl clothes are so much more fun than boy clothes. Short skirts are awesome!

2. How would you rate yourself when it comes to being masculine? (1-10) And explain why you give this rating?

I would say that I am in the 7 to 9 range. I was in the military and my current job requires a certain level of fitness, so I have been fairly fit my whole life. Not Arnold fit, but in good shape. I'm getting close to 60 though and getting a little squishy now. So I feel that I am a manly man, but I also notice sometimes that when I use my hands to talk, some of the gestures could be be construed as a little GAY. I also tear up sometimes when my wife and I watch girly movies. This seems to be happening more frequently. (Notting Hill, Love Actually and The Proposal are some of my favorites)

3. Do you have more guy or girl friends? Be honest and explain!

I have more guy friends. I think that is just by default because I know more guys. My workplace is predominantly male. I am also a little awkward (shy) around women. But as I thought about it more, I think it could also be by design. I think I'm afraid that if I hung out with girls more they would figure out that I'm a sissy faggot. Since I can't come out, that might be bad. But I desperately want to be able to talk to a girl as a gurl.

4. Have you ever thought about what it would be like to be a woman?

I think about being a woman all of the time. To be able to walk around in sexy clothes and sexy shoes enticing and teasing men into doing whatever I want. I think about having long red hair, nice full boobies and a tight ass. I would love to be able to do yoga the way a woman does.

5. Ever have a sexual fantasy where you are the woman?

Oh, fuck. So many fantasies. I would play with my own titties constantly. It's strange because as a man, I want to have sex with men. But I also fantasize about being a woman and having sex with women. I'm fucking GAY either way. But I do also fantasize that I'm a woman getting pounded by a giant cock or many giant cocks and they are squeezing my titties and cuming all over them. I love eating cum off of boobies. Being filled with a cock in all three of my holes seems like it would be heaven.

6. What about shopping, have you ever shopped for lingerie either online or at a boutique?

OMG! You don't even know. I have shopped at several online stores that cater to sissies. The challenging part was scheduling delivery so I could hide the deliveries from my wife. I have several dresses, a blond wig, red wig and I even bought an expensive pair of boobies. Of course I have all kinds of panties and stockings and a pretty good collection of shoes.

I have never gone to a store and shopped for lingerie, but there are so many fantasies. I would love to go shopping with a mistress or in a perfect world, my wife. I would be dressed as a boy. The first stop would be the shoe store. I would get a pair of sexy heels, not too crazy, 3 or 4 inches maybe. I would have to wear them out of the store while still wearing my boy clothes. Boy, would I get the stares.

The next stop would be the salon. A mani/pedi and a long red wig later, there would be no doubt that I was a sissy faggot in boys clothes. As we walk through the mall toward the lingerie/clothing store, I notice that a small gathering of men is following us now. They start taunting me, calling me a faggot, queer and many other names that make my little cock hard. When we get to the lingerie store, I have to go to the store attendant and tell her that I would like to buy some lingerie for myself. Of course, as hard as she tries, she can't stifle a giggle. This makes my cock twitch again. She helps me pick out some things that she feels would make me look cute and faggoty. I go into a changing room and my wife makes me come out into the hallway every time I try on a new piece. The men who were taunting me in the mall also followed us into the store and are now jeering and leering at me. One time when I come out of the changing room wearing a purple teddy, two of the men have their cocks in their hands. They put me on my knees, rubbing their cocks on my face and pushing them into my mouth. Then they take turns fucking me right there outside the changing rooms. The store attendant is now laughing her ass off at my predicament and taking photos. At this point my wife is yelling that I am a faggot son of a bitch, and I will be taking so much cock for her.

7. Have you ever painted your own nails or gone to a salon for a mani/pedi?
No, I have never used nail polish or gotten a mani/pedi.

8. Do you own any make-up? If so, tell me what and the brand you like?
No, I have no makeup. I have no idea how to apply makeup and don't really have opportunities to learn.

9. Have you ever worn makeup and/or dressed in public? Details!!
No, I have never put makeup on. I have gone to the park late at night on several occasions after midnight and got naked and then changed into a dress and heels and walked around the park for a couple of hours. I desperately wanted to get caught and fucked hard right in the park, but I never did. Which is also good, because as much as I wanted to get caught, I was also terrified of getting caught. Does that make sense?

Once when my wife was out of town, I dressed at home. I had on my red wig, my 34c boobies, a long sleeve short dress and a pair of crotchless pantyhose and wedges. Again, late at night, I ran to the garage dressed as a woman. My heart was beating out of my chest. I drove around my neighborhood for about a half an hour. My little faggot dick was poking up out of my dress. I finally pulled over in an empty parking lot and leaning against the hood of my car I furiously jerked off into my hand wishing I was getting fucked in the ass. Of course, I ate my load and then drove home and slept in a baby doll.

10. Do you have a "sissy" name?
My sissy name is Dawn. I know it's kind of a plain name but years ago I was infatuated with a red-haired co-worker named Dawn. I wanted to fuck her and I wanted to be her. So, I am, and I do because I fuck myself often.

11. Write a small paragraph or even just a sentence or two about yourself and where you are in your sissy lifestyle.

I am 59 and have been married for 33 years. I have been curious about cock almost my entire life from my teens. As I got older, the feelings got stronger. Early on I watched straight porn but it wasn't long before I was watching tranny porn, then bisex porn. I still watch a variety of porn but my favorite is gay porn. I have been playing with dildos and dressing for more than thirty years. As far as I know, my wife is unaware of my interests. Although I would not be surprised to find out that she knows and has just kept it to herself. She is not very sexually adventurous.

My wife and I are very different sizes so I wasn't really able to wear her stuff. That only provided the opportunity for me to shop for the things that really appealed to me. I have a small but nice collection of girl clothes that I can wear about once a month when my wife is out of the house long enough.

12. Submit a photo of yourself when you are dressed and feeling like your true sissy self! You may be discreet.