SHOULD I START CROSSDRESSING AGAIN??

Years ago I used to love crossdressing. I had all kinds of girly things. It made me feel so naughty and sexual and it got me some wonderful sex. But that was many years ago. A family member came to stay with me for a few years and I had to throw all my girl clothes away and haven't dressed since. Now that family member is gone and the urge to dress is pretty much gone too. I was wondering should I start dressing again. I've seen some wonderful outfits on Amazon that I would love to order and get into. Sexy things that years ago I would have died to get into. I didn't have access to all those sexy things when I was into crossdressing. But I don't know if I want to start all that secrecy again. So here I am on Naughtypost asking everyone who reads this to put it to a vote.

Should I start crossdressing again Yes ________ No ________

Report this

17 Comments

  • newest
  • oldest
  • most replies
  • most popular
  • By all means give it a try and and see if the thrill is still there. I think the mere fact you are asking means that we probably already know the answer.

  • I'm all dressed up with my bra black mini skirt and black very sheer see through panties on and been masturbating to my favorite shemale videos all day..and of course I'm a shemale and would rather be in gurly lingerie most of the time it makes me feel soo horney and when my shemale friends come over for our fucking times we like to see who's the sexiest and it's soo fun when we all cum together!!!

  • Edging all day long while crossdressed and watching shemale or BBC porn is one of my favorite things, too. But you should try it in chastity sometime while playing with vibrating butt plugs and big phat dildos, too. Bet that you have yourself a sissygasm...

  • Yes edging all day with a vibrating butt plug is a real turn on..but chastity is not my thing but masturbating in panties that I've cum in multitudes
    of times and peeed in gets my shemale cock precuming for hours and watching shemales cumming and fucking and getting nasty,dirty and naughty is just the best way to spend a day all dressed up in one of my sexy lingerie!!!

  • My husband does not fuck me. I am looking for sex chat. Chat with me now: https://ujeb.se/gprHh

  • I first dressed up in my sister's things as a fresh faced pre pubescent boy. I did this for myself and another older boy who cherished my cuteness in the most amazing ways. He really enjoyed showing me off and I loved it, all the attention. I stopped when I turned 16 and met my wife to be and now that we're married she's encouraged me to express myself that way. We go out together and the first time that I went out for a smoke (I really didn't smoke) and was with a man as a man was the best thing. I told him that I was a guy not a girl and he said he didn't care what I was. After a few minutes he had his cock up inside my quivering cheeks and quickly unloaded two amazingly good feeling warm loads of cum in my almost virgin tight ass. He sweetly readjusted my plush lace bottom panties as if nothing had happened and I returned to my young bride who excitedly waited to find out if my friend and I had kissed...

  • Yes

  • Yes.

  • When I was in middle school I was such a cute boyslut almost every time I got dressed up in my two sister's stuff. We moved last year after 8th grade and I've been good, until I started dressing up again, it's weird?

  • Even while my sister was living with me the whole seven years, dressing up was always on my mind. Now that she's gone I want to do it but starting from zero is such a hard road.

  • Finding the right friends is the most difficult lots of men want to be with me, and that's cool. The first boy around my age (I was 14 and he was 16) to discover my beautiful side was gay and couldn't wait to tell his other gay friends about the cute 14 year old sissy that he was fucking. It's better with older guys I think. I mean if I suck um it's like our business not his friends.

  • When I was younger my shemale friend said she would always keep our secret. So far she has.

  • I would vote a definite yes sweetie by all means dress.

  • Thank you for your vote. I'm tempted but dressing always kept me horny and made me a dick slut. I know if I start dressing again, I'll be that slut again. Isn't it strange how wearing girly things brings out your inner whore??

  • Do whatever the Hell you want.

  • That means I'll probably end up dressing like a whore again because secretly, that's what I really want.

  • Awww!!! Do it, it's so sexy!! I've been dressing for years and I can now pass as a mature lady and I love it. Silky underwear, stockings and suspenders under a floaty silky dress and heels, lush.
    I was born with a lisp and that has helped me cultivate a feminine voice and I have always stayed out of the sun, so I have soft fair skin.
    I am a real "bottom" but have always practiced safe sex which I love.

Account Login
Signup
Is this post inapropriate?
Is this comment inapropriate?
Delete this post?