Questions Sissies Ask - Why Can't I Feel Pretty?

Sissy Hubby Wants to Look Pretty

I forgot when this came up with an online sissy friend, probably a year or so ago. This sissy felt like (s)he looked too masculine and was afraid that dressing up just made her look silly. As usual, I paraphrase our talk as a "Dear Abby"-type exchange.

Dear Happy Sissy,

I love dressing up, I love being a sissy! Ever since I was a teen I have loved the act of sliding into sexy panties, the feel of a luxurious nightgown, the silky sensation of a slip, anything feminine or girly has always been a weakness of mine. This continued into adulthood and I have quite a collection, mostly lingerie. I can't dress freely but I do get plenty of chances while traveling or when wife is out.

The trouble is that I don't look like a sissy. My frame is masculine, I've been referred to as a "fireplug." I also have a lot of hair, body and otherwise, that is jet black. Sometimes I will be enjoying myself lounging in a pretty nightie and then spot myself in a mirror and the sissy mood evaporates. I see a hairy guy in a girly gown and I am afraid that I just look ridiculous.

I know my problem is small-time compared to some other sissies but it still sometimes bothers me. My wife has said that I am too manly looking and should give up my girly habits entirely, and at times I can't help but feel she might be right. I wish I naturally had a more feminine look but I don't. I love the sissy feelings when I dress up but then I sometimes feel silly, and I hate that. What should I do? Am I too masculine to be a sissy? I love so much feeling like a sissy, but why can't I feel pretty?

Signed,
A Sissy in a Man's Body

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Dear A Sissy in a Man's Body,

I am so glad you wrote to me with your question. I have one primary message for you and it is this: Every sissy that I know, myself included, feels exactly the same way at times, if not all the time! We as sissies adore women, worship femininity, and want to emulate feminine ideals as much as possible. Unfortunately, there is a sometimes-rude reality that all sissies confront: We are still men! Or at least, we are still male, if you know what I mean.

One trait common to all sissies is that we want to feel feminine, we want to feel pretty. Another is that we all feel like we fall short of the feminine ideal, and the truth is, we do fall short. Of course we do, we are not women. But another truth is, women feel the same way! They have a feminine ideal in their mind too, and they also feel that they fall short, and the truth is, they fall short too. The reason is, sissy or woman, it is impossible to live up to an ideal.

It is fine to have an ideal in mind, it is fine to try to live up to that ideal. Just know that you will never be able to. An ideal will always be out of reach by its very nature. My advice to you, dear sissy, is the same as it would be to anybody, women included: Acknowledge that you have this ideal in mind, that it will always be unreachable, and that it is still fun to try!

So don't worry about being too masculine to be a sissy, you are a sissy whether you like it or not. Luckily you do like it! So dress up in the prettiest, frilliest, sissiest things you can find. Strut around like a beauty queen and luxuriate in the feminine mystique. If you need to feel more feminine, do something new. Go shopping and buy a dress, shave your legs, anything new and feminine. And if you must, don't look in the mirror.

Love,
Jackie (The Happy Sissy!)

P.S. - I mentioned not looking in the mirror but really I think you ought to look in the mirror. Even if you don't see the woman you would like to see, you still yourself as a sissy, and it never hurts to be reminded.