C.R. wrote: “I just discovered your blog/YouTube today and really love your work. I have a bit of a pressing issue and could use your advice.
I am a sissy. I love the idea of wearing adorable outfits – French maid, Alice in Wonderland – and also have an affinity for diapers and abdl accessories. I am completely straight and love being a man. I just wish (and fantasize about) from time to time, I could be a cute little princess.
My partner knows. We have experimented but it’s not something she enjoys so I have kept my activities to myself out of respect. We do enjoy some D/s play for what it’s worth.
Before meeting her (and for a while after we started dating) I would binge and purge my closet … Acquire 2 or 3 outfits (usually second hand) wear them a few times, then throw them away in shame. For the last five years I have not owned any sissy items.
Recently, my partner suggested I buy a dress of my own to wear in private. I have found a perfect dress from a sissy clothes maker on etsy … It is within my price range and a sissy dream (satin with lace and a petticoat) … But I can’t bring myself to buy it. I just keep re checking my measurements and debating whether to get the purple, pink or blue dress.
I really don’t know why I am so nervous to order it.
Any ideas on where this hesitancy might be coming from? Do you think it’s a mistake to buy the dress? Is this my subconscious trying to tell me something or am I just overwhelmed that my fantasy is within my grasp?
Any thoughts are appreciated!
P.s. If you do think I should get it … Any votes on whether I should go pink, purple or blue?”
Liz says: I suspect your hesitancy is from a combination of shame and guilt. Shame because you’ve internalized our culture’s message of what masculinity is supposed to be and guilt because you enjoy something your partner doesn’t and you’re concerned she’ll want a “real man” instead of you one day.
We are constantly re-defining what femininity and masculinity means, and when you look at other cultures or our own throughout history you’ll note that society often changes its tune with what it deems appropriate clothing for men and women. I don’t know too many people who would say a man in a kilt isn’t masculine. There was a time men wore tights and wigs, too. But you do this in private anyway, so why feel shame over something that hurts no one and doesn’t affect other facets of your life negatively?
It sounds to me that your partner knows what makes you happy, is accepting of it even though she doesn’t care to participate anymore, and doesn’t want you to resent her and feel deprived just because she doesn’t join you in your sissy activities. Plus, she still enjoys D/s with you! In other words, it’s hardly the behavior of someone who’s hoping you’ll change or wants to leave you. This might not even be something you worry about but I thought I’d point this out just in case.
As to what color dress you should get, it depends on your hair color and skin tone! Go with pink if you’re tan and have dark hair, purple or blue if you’re paler. 😉