It is no secret that I enjoy cross dressing men and have had a few men in my life that I have enjoyed having sex with why they are dressed as women but let me explain why I enjoy them.
I admire courage
First of all if you are brave enough to tell me you like to dress in women’s clothing I am instantly excited, courage and being proud of who and what you do is a turn on. So anyone who has the courage to share their feminine ways with me already is a step above in my book!
The Sexy Factor
There is no denying that if done well and dressed properly in women’s clothing you will me damn sexy!  When I say properly I mean with class and style…. a slutty look on a man or woman is fine for those rare occasions it is called for, but dressing slutty all the time is not really super sexy it is like hmm okay slutty again…besides leave the slutty things for under your clothing. Men dressing in women’s clothing is always a reason for me to smile and lets me imagine what is under a sexy dress or skirt….I dig that and find it very sexy
Cross dressing men in lingerie
Can I just say WOW SEXY Please though if you want me to enjoy you being a cross dressing man and personally be excited about it groom sweetie there is nothing worse than a sexy corset on a man and chest hair sticking out all over ( yes I know some cant shave) but if you are unable to take off that hair choose something with more coverage to wear. But a Man in a sexy pair of stockings laying on a bed in a cute nightie and me next to him in my sexy stockings and nightie is like over the top hot!
Need Help dressing?
Do you find your self lost in the world of women’s clothing? Do you need help finding lingerie for men or figuring out what goes where and how? Give me a call I can not only help be your fashion guide but your play mate as well
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While not ‘exactly’ a cross dresser, I do LOVE wearing panties daily. They feel wonderful and perfectly remind me of my submissive place. Real men don’t wear panties but cuckolds with ‘lil dickies’ do. So while I could never pass and may never completely cross dress…..I too admire the courage of those who do and understand the appeal!
well cuckie you in panties is just what I love and you are right you being fully cross dressed is not such a hot look I don’t think but man my little dickie in chastity behind sexy panties well you rock it babe!!!!
Anyone interested in cross dressing men should look at this. Be sure to watch the video.
https://www.manhattantheatreclub.com/2013-2014-season/casa-valentina/
wet spot thanks for the link I don’t normally allow links in comments but for you I made an exception
I’m with you Ms. Constance, I think it is very sexy when men dress in a feminine way. They feel they have to work at it so much harder than women do, and most of the time, that hard work seems to pay off. It means they are not just girlie, but immaculately so. But even so, like us real girls, everyone needs help getting ready at times, and I know that any of our guys would love to have your help in getting girlie and would be lucky to have you and your help!
Ms Christine I think you and I would make a great consulting team we could help the cross dressers pick out clothing and the sissy girls find their sissy style and than we could have our way with them hehehehe
I can practically hear you saying this as I read it, Ms Constance. Your personality comes shining through in this posting. *smile* Why, you offer fashion advice and cautionary words. Very helpful information for a cross dresser or sissy in training. Your last line is so true. You will be a playmate. A gloriously fun one too!
awww Ms. Violet my sweet sexy friend thank you and I know you and I share a love for the cross dressing and sissy clients and we not only want to help them but have fun with them and I have to say in no safer hands would they be than in yours
Loved this post, Ms Constance! I agree that dressing slutty has it’s place, and I enjoy that sexy look too, but I like the classy look even more. I love the look of a stylish business skirt suit with heels and hose.
jemjem you are my classy girl that dress we got you is so perfect sexy without being slutty and girl you look good in it too
Thank you so much Mistress! I love the dress and love wearing it especially because you picked it out for me!
it is perfect for you my sweet girl
This is a great post! Ms. Constance, I really agree with you about the slut look or classy trashy. Some go for that look, maybe thinking that is whats appropriate. I hope they read this and realize we like to keep it classy and get pretty excited about it!
thanks Ms Meredith as I said I do love me a slutty look but time and place means everything nothing beats a classy sexy cross dresser
I have a regular caller that really enjoyed this past Halloween because he went out all dressed up for the first time, but he has since confided in me that he liked it so much that he’s not going to let anything stop him from stepping out more and more. I am so proud of him! It’s a very brave thing to live YOUR OWN WAY, to be who you are even when you might get pushback or negative attention. Here’s to hoping that anyone else that is in that crucial place can see this post and make the choice to always live every day exactly how they choose, doing what they were meant to!
aww Ms Amber that is so awesome it warms my heart! I wish everyone could live they way they feel on the inside without fear of judgment if it is not hurting someone than do it I love the be who you are that you said thank you
Just wearing bra/boyshorts against my soft, smooth, girlish skin is to much to resist. Also wearing sheath dresses/yoga pants with pumps/ankle boots. Ms Violet and Ms Cindsy said I’m badly in need of session:( for me dressing is only way I can get hard and off. I confessed to both mistresses about having them do this to me:(I came clean and told them it’s what I want. They are right as it’s time for them to take over and dress me and turn me into their sissy boy.
I agree, Ms. Constance, that it takes courage to admit to being a cross dresser and that, in and of itself, is very sexy. I also agree that to keep it classy and sexy, it must be done with style and finesse. Slutty is definitely good on occasion, but there’s something super hot and sexy about intertwining nylon covered legs during a lovemaking session, wouldn’t you agree?
yes courage is key when admitting your kinks especially cross dressing because not everyone gets it……..and I know you like a hot slut as much as I do but also appreciate a classy man dressed in feminine things as well totally agree with you
I completely agree, Ms Constance! Cross dressers are a blast to speak and shop with; I frequently have shopping dates with mine. Watching their transformation is a journey, and I love offering my guidance and advice. I’m sure your cross dressers are very grateful for the instruction of a sexy woman like yourself!
I agree I love helping my cross dressing clients to shop and dress and get all pretty sometimes they just need a womans touch 🙂