Confessions in Daisy Dukes

DaisyDukes with Fogal Rapallo tights

OK, for starters, sorry about the long scroll down. I guess I could have made the image a little smaller but then I would have the misfortune of not letting you see the new love in my life for all its glory. I find it odd that I’m getting around now to try out these highly sexy denim shorts since they’ve been around, oh, since the 80’s. Better now than never as it goes.

Maybe it was a particular image that caught my eye or just the urge to wear something feminine but different, I can’t remember, but I went out and bought my very own pair of Daisy Duke shorts in my usual jean size (not revealing it, sorry). You should have seen my face when I ripped open that package and rushed to put them on.

They barely hung onto my ass meaning they were meant for a woman quite heftier than I. Fine, returned it and ordered another pair a couple sizes smaller. I was having my doubts if these would actually fit since I had never sized or worn womens jeans and the size ordered was WAY below my usual size for even a tight pair of jeans.

Received in the mail again. Ripped open the package, slipped them on with a bit of pessimism. Prepared for another return.

Yet the Hollister shorts fit, well, perfectly. They were tight but not constricting and no loose areas. I noticed on the tag, they have the slightest bit of spandex which allows them to stretch and cover my ass perfectly and comfortably. But now we have to get down to what I was really waiting for. The match made in heaven: wearing them over pantyhose.

Daisy Dukes with Omero pantyhose

I have to say that the combination aroused me to the point to where I was extremely pleased that the Daisy Dukes could expand ever so slightly to contain my erection. It’s as if these shorts were a piece of lingerie actually wearable in public. Pair them with a sexy top and heels, however, and you will be that hot little number in your town. I did happen to go out in public, although somewhat tipsy at 2:30 AM and ducking back in after seeing someone walk up the street.

Still, I felt too sexy not to have a go at public view. Daisy Dukes were probably the missing link I needed to get my ass out and show the world a new crossdresser. Maybe another day for the full public outing, but maybe you get my point.

The DDs look great with any pantyhose, really, but high heels are an absolute must since they lengthen those stems and make that ass all cute and round(ish). I’m kind of particular to the look in the top image paired with black opaque Fogal Rapallo tights, a black bustier top and beige Guess sandals. Any 30 – 40+ denier tights, though, are sexy with the shorts in my opinion. In the second image, I have on an Oroblu bustier, Omero Luxor pantyhose (look for a review soon) and Guess slingbacks.

DDs, pantyhose and are obviously not quite the getup to go out for a trip to the supermarket or for a stroll for the average female. Nothing quite beats that sexy feminine feeling, however, when you know you have a more complete appearance as opposed to, say, wearing those ragged bra and panties with your beloved pantyhose. Then you finish it off by snapping a pic so you happily can jerk off to it later (guilty).

If you remember one thing, just look for Daisy Dukes in a smaller size.

Tagged with: , ,
Posted in CD Diary
9 comments on “Confessions in Daisy Dukes
  1. Willingboi says:

    Those are sexy legs…and the daisy Dukes are perfect

  2. Chris says:

    Wow! That is so sexy! Have you had a chance to go out for some length of time since writing this?
    If I were you, I’d go shopping at a women’s clothing store in them and show off there. It’s a relatively safe environment, limited exposure, and the vast majority of those seeing you will be women.
    I sometimes go to try on women’s swim suits with pantyhose. It’s a real rush!
    Try it!

  3. Amelia says:

    Hooray for the return of the sexiest person on the internet!!! Those DDs look spectacular on you and I love your tan/black shoe/hose contrast.
    I think I was in a state of withdrawal because you hadn’t posted in so long. I was a bit worried that you’d decided to stop posting or had become ill. Then I thought that your last story series, (which was hot as the sun, by the way,) might mean that you were working hard, doing research for future stories. Cue the scratchy wah guitar.
    So, before I go further, (serious, earnest voice over activated,) I would like to declare that I think this is the best,sexiest and, most insightful blog I’ve ever encountered. Thank you. I credit you with helping me to come to terms with my own dressing and sexuality. Your erotic stories have guided me to more shattering pantyhose orgasms than I can count. Your thoughts on pantyhose, crossdressing and sexuality resonate so clearly with me and, I’m always left wanting more, inspired to go deeper.
    And, you are sexy as hell. I am so glad I kept checking for updates!!!
    Do you ever correspond privately with readers? Because I have a feeling I would really enjoy talking to you.

    xo Amy

  4. Sheery says:

    @Amy Thank you so much for the kind words! If this website has helped you (or anybody else) in any way then everything has been well worth it.

    I must apologize for the lack of posts recently but it is primarily due to other work/things. I’m going nowhere!

    Feel free to send a DM on Twitter @sheerysisi or use the contact form here:

    For obvious reasons, I won’t post my email.

    X Sheery

  5. Sheery says:

    @Willingboi Thank you!

  6. Sheery says:

    @Chris No unfortunately I haven’t but I’ve made other crosdresser friends that are convincing me otherwise.

  7. Elizabeth Fredericks says:

    Thanks Sheery for sharing. I so understand in that I had the same revelation. I love wearing DD’s and suntan hose while doing my yard work. I have older neighbors that could care less even if they noticed and I get to have the electric feeling of pantyhose while feeling fem and content and getting those pesky maintenance tasks done. Hard on hose though unless you are careful, the outdoors is not run resistant.


  8. Sheery says:

    @Beth I believe DDs were specifically made for wearing for yardwork (in public view of course).

    And, yes, you have to watch the bushes and tree trunks around your pantyhose… thanks for your comment!

  9. Glossy says:

    DDs, shiny pantyhose and black sling backs are very sexy. Your outfits are very becoming and as a someone who crossdresses, I enjoy wearing similar outfits with the right combination of shorts, pantyhose and heels. It make me feel very sensual and feminine.

Leave a Reply

Your email address will not be published.


This site uses Akismet to reduce spam. Learn how your comment data is processed.

Cookies are used to ensure the best experience on this website. By continuing to browse this site you consent to the use of cookies. Accept