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  • #658319
    Ruby Renee
    Registered On: June 8, 2022
    Topics: 3
    Replies: 12
    Has thanked: 66 times
    Been thanked: 77 times

    So, I may have “accidently” entered the online hookup scene without even realizing it..

    I was told that Fetlife was a good site for meeting other crossdressers.  I signed up recently, right around the time I joined this site.  I listed the current city and I just recently uploaded some photos (and yes, some of them may be a bit racy).  I knew the site was more adult/kink oriented, but I heard it was more like a social media site.  I didn’t realize it was first, and foremost a hookup site.

    I’ve been kinda unsuccessful at connecting with other crossdressers on there..  Instead, I’ve been receiving a lot of messages from local guys who want to get together with me..  For most of them I’m going to say no, but there have been one or two guys that are actually insanely good looking, and I feel like I’m going to kick myself later if pass up a good opportunity..

    I’ve been with men before, as my male self, but never as my femme self..  I have NO IDEA what the etiquette is here.  I don’t know what their expectations are.  I don’t know if I have to use a fem voice (or if I even can).  Some of these guys messaging me are starting to act impatient.  I haven’t even mentioned that I have crazy social anxiety..  I haven’t even left my apartment dressed yet, and very few people have even seen me dressed. Am I kidding myself here thinking that I could go through with this?? I am in way over my head..

    • This topic was modified 1 month ago by Ruby Renee.
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    • #658462
      Jess Secret
      Registered On: February 18, 2021
      Topics: 15
      Replies: 441
      Has thanked: 1108 times
      Been thanked: 1811 times

      Hi Ruby I can lend some advice here since I have a boyfriend. Didn’t meet him online but just wanted to share a few pieces of advice. To Jenny’s point, be careful and safe, plenty of guys out there are only thinking about sex, but if and when you do really connect with the *right* guy and make the decision to go to bed with him, it will be an incredible night take my word for it. Do make sure to really get to know him and know that you can trust him. Since you mention you will be your fem self, make sure you build up your lingerie wardrobe, beautiful/romantic lingerie is a must have in the bedroom for that special night. If possible add candles, soft music, satin sheets and champagne, had all of those things for my first time with my boyfriend and the night was magical. Make it feel like you’re a bride on your wedding night.

      6 users thanked author for this post.
    • #658451
      Ruby Renee
      Registered On: June 8, 2022
      Topics: 3
      Replies: 12
      Has thanked: 66 times
      Been thanked: 77 times


      So I updated my FL profile to more honestly state my experience level, and what I’m looking for.. I chatted with 3 guys (I’m ignoring messages from faceless profiles), and I was just completely honest with them, basically about everything I mentioned here, and that I’d prefer to get to know someone a little before hooking up. 2 of them are still interested (including one really hot guy), and one hasn’t responded, lol.

      I’m just trying to take things at my own pace (like I said, social anxiety), at the same time trying not to miss out on any good opportunities. It’s not that I’ve never had an online hookup with a guy before, I have (I used to occasionally use Grindr). Its just that doing so as my femme self, while crossdressing is still new to me, feels like a whole new ballgame.

      Thanks to everyone who gave me advice..

    • #658424
      Jane Don
      Registered On: March 4, 2020
      Topics: 3
      Replies: 95
      Has thanked: 25 times
      Been thanked: 290 times

      I’d say-Just have fun-

      3 users thanked author for this post.
    • #658422
      Jenny Thigh High
      Registered On: August 10, 2019
      Topics: 7
      Replies: 303
      Has thanked: 1661 times
      Been thanked: 1577 times

      Great post and some of the advice below is really good.

      I have met up with many men from online, both as a guy and as Jenny.

      Go slow, keep your expectations low, be totally upfront and to the point regarding how public you are, how you “sound,” etc. Don’t mislead anyone, but also recognize very few guys will be totally honest with you too. And yes, most of them just want sex, no matter what they say. Not a bad thing (!!!), just keep your expectations low.

      Having said that, I’ve had some AMAZING sexual experiences with men met online. As you indicate, you don’t want regrets. Caution is essential, but too much caution will lead to missed opportunities. 🙁

      When you do ultimately connect with a guy, especially dressed, it’s just the most incredible experience imaginable.

      PM me if you ever want to chat more on this topic 🙂

      Good luck!

    • #658398
      Johanez Johnston
      Registered On: September 16, 2021
      Topics: 2
      Replies: 24
      Has thanked: 44 times
      Been thanked: 79 times

      The ones who are being “Impatient” are players and just want (at best) a FWB… at worst, a quickie… I find it is best to politely decline and move along to less inappropriate and a possibly disastrous situation.


      2 users thanked author for this post.
    • #658391
      Managing Ambassador
      Registered On: January 21, 2018
      Topics: 613
      Replies: 1584
      Has thanked: 9265 times
      Been thanked: 5491 times

      I don’t know what their expectations are.

      Probably sexy times.

      I don’t know if I have to use a fem voice (or if I even can).

      I would say, probably not if you were honest up front. I never do. If people expect me to talk, they better be ok with how I sound.

      Some of these guys messaging me are starting to act impatient.

      That’s really not a good sign in my opinion.

      I haven’t even mentioned that I have crazy social anxiety..

      Shoo, me too. Sometimes you can kinda feed off the nerves. Medication helps too if you’re on any for that sort of thing…but don’t overdo it if that’s the case!!

      I haven’t even left my apartment dressed yet, and very few people have even seen me dressed.

      Would that create problems in your life? If you can get away with it, you should do it.


      Those are my initial thoughts here. Beyond that, Jenny had some pretty good advice farther down the page. You kinda have to place yourself in the woman’s shoes and think like a woman. Safety first hon.

      4 users thanked author for this post.
    • #658358
      Araminta Purdy
      Registered On: January 23, 2020
      Topics: 10
      Replies: 480
      Has thanked: 1003 times
      Been thanked: 1815 times

      First: Don’t Panic!

      Second: Don’t be seduced by pictures.

      Third: Be a lady (relatively).

      Fourth: Make sure you are convinced the other person is safe, suitable and sane before giving away any personal information.


      5 users thanked author for this post.
    • #658349
      Aurora Borealis
      Registered On: October 25, 2021
      Topics: 1
      Replies: 150
      Has thanked: 483 times
      Been thanked: 432 times

      Dear Ruby,

      I dont consider myself to be any kind of dating or relationship expert but, here goes.

      First of all are you really wanting to date or start a relationship that maybe a guy wants and has certain expectations about? If youre not up front from the other tmight be complications when he finds out
      youre not a GG woman.r He might get frustrated, maybe m really pissed off.

      Its really on you to be honest even with a stranger. Take this for what its worth. Hugs, Aurora B. .

      4 users thanked author for this post.
    • #658330
      Jenny James
      Registered On: February 16, 2022
      Topics: 1
      Replies: 22
      Has thanked: 54 times
      Been thanked: 90 times

      Hey Ruby,

      I have met with a couple of guys online and my only advice is go slow! Make contact, get a phone number and meet as guys for lunch somewhere first. Somebody in a real hurry to hookup may have bad intentions or just looking for a “quickie” and doesn’t appreciate what it took for you to get dolled up.

      If you have a friend that knows you crossdress, make sure that they know who and when you are meeting somebody. I was attacked years ago because I was desperate for some male acceptance of Jenny and let myself get cornered in a hotel room. I was completely defensive and lets face it, you really don’t want to scrap in a tight skirt and heels. Only reason I got out is I did enough damage that he fled.  Get to know who you will be meeting!

      Also, contact other CDs on that site and ask for a good guy reference.  You may also be able to set up a meeting with you two gurls and the guy. Safer for you and extra fun for the guy.

      Although this is not a dating forum, there may be another member that lives in your area that can vouch for a guy that they trust.

      Good luck Miss Ruby and have fun!



    • #658328
      Barbie Satin
      Registered On: May 15, 2022
      Topics: 1
      Replies: 191
      Has thanked: 443 times
      Been thanked: 680 times

      I sent you a PM. Ask me anything. I am pretty sure I am the expert on the subject here. I had over 250 dates in my time.


    • #658322
      1968 Sonia
      Registered On: November 14, 2021
      Topics: 0
      Replies: 50
      Has thanked: 141 times
      Been thanked: 178 times

      Be Ruby and enjoy dear!!!!

      You know what men like



      2 users thanked author for this post.
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