Ask Sheery: Yet Another New Advice Column

Ask Sheery

Having this blog can feel pretty one-dimensional at times. I mean I’m the one doing all the talking while just you sit there and take it all in.

How rude of me!

So, to be polite and maybe let you have a word or two in the conversation, I’m starting this new column, Ask Sheery. This has been an idea of mine for quite a while and now I figure is a good time to give it a whirl. So here we go…

Weekly, I’ll take your questions posted in this or any post comments and answer them in a new post. While I cannot guarantee that I’ll be able to answer all of them, I’ll do my best to try.

What should I ask, you say? Here are some topics to get you started:

  • Advice on being a crossdresser
  • Advice for your pantyhose fetish
  • Sexuality
  • Anything on pantyhose, lingerie or any of those girly things we love
  • Personal questions to me

Again, feel free to post your questions below or in any post. I look forward to hearing what you have to say;)


28 Comments on “Ask Sheery: Yet Another New Advice Column

  1. crossdressing as it relates to sexuality… Why did I used to feel I was straight as I was told most crossdressers are and end up bi/gay? I really am beginning to think that more CDs are bi or gay than I was originally led to believe. What are your thoughts on that?

  2. I would have to say that the proportion of bi/gay/straight crossdressers to hetero crossdressers would be roughly the same as those of non-CDs. Most of the research out there have been surveys that tend to support this although, personally, I haven’t come across a major scientific study that would come to this conclusion.

    If the question is does crossdressing determine your sexual preference? In my opinion, maybe for some but not for the majority. And if it does, great, you have my support all the way!

    Thanks for your comment Charlie.

  3. The research out there does support and prove that most CD are straight. What happens is that the proportion that are Bi/Gay and make it evident on the internet and are more ‘out there’ and open, more than make up for the straight CDers! Rather like other stereotypes of race etc.
    I can see where you are coming from, I have had my own concerns, every where I look on the internet CD are bi/gay, and had to question myself on the implications. Could it be that a lot of the straight CD simply don’t go on the internet to advertise the fact, won’t risk pictures and being discovered, don’t have the means for that, or happily already in a hetereosexual relationship. -Where there is a demand a internet site will pop up and so far it is very difficult to find a site for straight CD. It would not be financially viable, a ton of guys all looking for women and very few women, so hence the bi/gay market seem to outweigh.

  4. Hi Penn, what type of straight CD website were you looking for that have not been able to find?

    From what I have seen there are sites on the internet where straight (and bi/gay alike) crossdressers will post pictures of themselves (hello Flickr). But yes, those sites that cater to crossdressers who are fond of tgirls and transvestites are more likely to have a sexual preference towards them whether bi, gay or even just curious. Really, there is pretty much a website to suit every taste in crossdressing and/or fetishes but sometimes a little digging is necessary.

    For hetero M2F crossdressers, though, they are likely to look for sites that satisfy their particular fetish. For instance, just take a look at one of the many flavors of pantyhose fetish websites out there. You won’t see other crossdressers on these sites, of course, but rather women modeling in a role the crossdresser fantasizes about being in.

  5. HI there, nothing serious, just pointing out you won’t find a dedicated site for straight CD to find females. Sure there ARE sites SCD can go on, but they get swamped by BGCD messaging them! LOL
    Agreed tvchix is a good one, but still not many women.

  6. Ah, I see what you’re saying now. You’re exactly right, the ratio of crossdressers looking for women to women looking for CDs is definitely skewed A LOT towards the CDs. I believe that is just due to the reflection in society as a whole. Yet still there are women out there who love CDs, though, and I’ve even met some online myself. But truth is you never really know who could also be posing as women. I may have met some of those too.

    I appreciate your comments Penn.

  7. U Should Check Out APerson That I Found On The Net Called Liclic Pantyhose, She Is So Hot in Pantyhose And Loves Dildos And My FavorIte Shinny Blk PantyhoSe ,When U Watch Make Sure U R Dressed Up And Have A Good Toy With U!!!!!

  8. could you refer a reliable website with lovely CD. for years i have been wanting to meet a lovely CD. i use to know a very pretty CD in my town but she is no longer here and she could put any women to shame. please put me in the right direction

  9. Hi Davey, is a great place to start. You may or may not find someone in your area but, who knows, you may get to travel a bit!

  10. Sheery,

    I am a mostly straight (bi-curious) male who loves pantyhose. I will be traveling to Las Vegas soon for work and wanted to pick up some sexy hose to wear while out there. What I’m looking for are some sheer to waist hose that won’t fit too snug around my package. I’m 5’11, and 220 pounds, so finding plus sized hosiery is a bit of a challenge. Basically I want to surprise my wife (she knows I wear and encourages it) when she comes out to spend the weekend, and I wasn’t her to be able to wrap her hand around my cock while wearing the hose (and possibly suck me too). Any advice for brands that would allow for that sort of freedom of movement?


  11. I’d highly recommend a pair of Wolford Neon 40 tights in XL for that special occasion. They don’t fit too tight and form well to any figure. They are pricey but it would be well worth the “surprise.” You can buy them online at but I believe there is even a Wolford outlet in Las Vegas that I’ve even been dying to check out.

    I hope you find what you are looking for!

  12. OH DEAR I THINK I’M IN HEAVEN!!!!!!!! HERE I AM CLOSE TO 60 AND NEVER GONE OUT DRESSED!!!!! I know could have done something before now but for me always wanted someone to share my feelings with!!!!!!! Someone to dress with or just give me a little courage!!!!! Living in southern Alabama no such luck but maybe now with this sight that can change !!!!! Haven’t filled anything out yet but the whole thing sounds wonderful!!!!!! Can’t wait to get started with pics and all !!!!! PLEASE PLEASE keep up the wonderful work I Love you already!!!!

  13. Pantyhose look so amazing and I assume very enjoyable to wear if you have a fetish for them. I assume shaving your legs is important to those who want to fully enjoy the experience of wearing this sexy item. For people interested in trying pantyhose but want to go even beyond that, what other items are most enjoyable to compliment wearing pantyhose or at least do you feel are the most sensual? If you had to recommend a first outfit for somebody interested in having a pleasurable experience with pantyhose what would it be? Satin robes and slips look like they would feel nice against the skin and sliding over the pantyhose. The secretary look with a pencil skirt and silk blouse looks classic, sexy, and amazing. I also like the Hooters look with the older satin shorts, it looks like that would be fun as well. Also, what footwear do you recommend? Soft slippers for comfort and feel or black stilettos for a classic look and giving the legs a nice long line? Also, what color combinations do you think look good as well with these outfits? I like the suntan and jet black colors when it comes to pantyhose.

  14. @Mark My personal preference with pantyhose is lingerie such as teddies or chemises and tall platform heels. Tall heels give the best shape to your legs but can be dangerous from falls if you’re not use to them so be careful!

    Of course being a mock Hooter’s girl would be sexy as well. Plus you can buy those outfits at Hooters too. One tip, also, you can sneak into the girls room to buy their pantyhose from a machine!

    Thanks for you comment.

  15. Sheery I love your site. I remember your story of meeting those 2 attractive xdressers randomly and having that orgy. When I’m horny I imagine you as one of those hot xdressers and you pounding my pantied ass to the point where the bed is almost coming apart. I’d love to see you in TALL boots, bc your legs are already long and tone. Thanks for starting up this site you’re fucking hot and I fuckin whack it to you often

  16. Hello sweet Sheery ,
    How are you ? I hope that everything is allright. I have some questions…
    I am now crossdressing as I speak . I have come to CD , since I started inserting a tampoon in my little butt as I was 9 or 10. Since then I masturbated using every kind of ,as I call it , pre-CD period. Then Mom’s lingerie and nylons,oh nylons…It may sound all a little bit of abstract but I always speak the truth. And since I started Crossdressing I never reached beyond hiding as a Closet CD. I went out with some satin panties and nylons .But never showed my Femine site to anyone.This writing here is a big step now . I am 20 now and I havent had a so “easy life ” or normal. Now I have a “long-distance relationship” and I am Straight as an arrow, but this morning I buyed myself an pantyhose and I took some panties from my aunt that she forgot and isnt wearing anymore. I buyed even an mini-vibrator this morning , lube and condoms. I dont know,I dont know if this is right but mostly ,when i dress and masturbate some bad things happem in future. Like some bad luck or idk… But yeah,I feel good now ,tight, horny , all ready to play with myself a little bit this evening . I would like to hear your opiniom Sheery.I have read all your posts,stories that make me wanna get another CD and fill my fantasy and make someones day better. Maybe I have wrote too much ,but I hope you understand . I would love to write with a real experienced CD often. With love and hugs. Me

  17. Sheery,
    Your site is great and has a lot of good information. I have a pantyhose fetish like many who visit this site. Ever since I was very young the look of pantyhose has always fascinated me and stirred up feelings of arousal. Walking past pantyhose displays, seeing beautiful women on television wearing pantyhose, watching cheerleaders and Hooters waitresses in their pantyhose has really increased my curiosity about this amazing article of clothing. Also, it seems like those with a pantyhose fetish who finally get a chance to finally wear pantyhose really enjoy it and experience erotic bliss. One of my favorite looks is the classic secretary/business look with suntan pantyhose, black stiletto pointed pumps, classic pencil skirt, even a satin blouse. This outfit is what I would like to wear the most because I think it compliments the pantyhose and just looks amazing. My question to you is when you shave your legs to prepare for pantyhose (which it seems is a must), do you shave everything from the waist down including pubic areas to enhance the feel or just your legs? Also, I think it sounds equally exciting as well as arousing to shop for pantyhose. I would like the experience of going into boutique like Wolford and telling them I am shopping for pantyhose for myself even though this seems really intimidating and embarrassing at the same time. What experiences have you had buying pantyhose in person for yourself?

  18. Sheery, your site is great especially for those of us that have a fascination for pantyhose. I’ve been attracted to hosiery since I was real young. I find myself aroused by the sight of pantyhose, including business women, Hooters waitresses, cheerleaders, etc. Even walking by pantyhose displays at stores gets my attention and curiosity going. I think it would be amazing, fun and sexually pleasing to try my favorite combination- the business/ secretary look. I love the feminine look of shiny black stilettos, pencil skirt and a satin blouse accented with a pair of soft and silky pantyhose. I look forward to shaving my legs which everybody says is necessary to enjoy the feel of the pantyhose legs but was wondering if you shave everything from the waist down including pubic area or just your legs? I also like the idea of shopping for pantyhose in person, even though this seems scary and very intimidating. The idea of walking into a Wolford boutique and asking a saleslady for help and pantyhose recommendations seems equally arousing. Have you had any experiences buying pantyhose for yourself in person and if so, how did it go?

  19. @Jack I shave it all… no hair at all!

    My experience with buying pantyhose is that the calmer you are, the easier it will be. That said, I’m always trembling with fear and even shaking after I purchase and leave a store. I find, though, it helps to find a cashier who is older rather than younger otherwise you get the feeling you might be “outed” even though you don’t know the person.

    Try it though. It’s very exhilarating!

  20. Sheery…I Like Wearing Pantyhose, But “I LOVE WEARING MY BRAS”, We “GIRLS” Should “ALWAYS WEAR OUR BRAS (and Panties)” With My “Fem Name” You Can Tell That Playtex Bras Are My Favorite To Wear !!! THANK YOU SHEERY

  21. Hi Sheery,

    I have a couple of questions since reading your last post, I find you can help others navigate through this experience!

    When you get in the mood to dress up –do you enhance it with any other kinds of things like poppers, alcohol, medical cannabis or things to make you feel more sexually charged up?

    I find that I can only handle so much of my ‘feminine playtime’
    until I have to ‘release’ and then this feeling of
    dread, guilt, shame and analyzing myself…happens….like why am I like this?
    I clearly am entranced by femininity and all the silky pleasures it brings but being heterosexual it confuses me and often am conflicted with the experience.
    Is it ever possible to get away from these feelings?

    Lastly, a big confusion factor with me is anal play because I have this constant fetish of having a dominant woman use a strap-on while she is wearing pantyhose and silky items, as am I.
    Anal play is not something I do that much because ultimately it produces the most shame for me.
    In the moment of fantasizing and using a toy –the pleasure is so intense and so powerful.
    However, after climaxing—it is a surge of shame.
    I am in that state of mind —asking myself why?
    Is this common?

    Then I find myself wanting to throw out all of my items.

    Any advice is very much appreciated!

Leave a Reply

Your email address will not be published. Required fields are marked *


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