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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..
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!
Jenny
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. .
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!
[UPDATE]
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..
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.
So.. Quick update on this.. Since making this post a little over 3 months ago, I’ve actually had a few really AMAZING experiences. Including an ongoing friends-with-benefits(I think?) thing I started with an adorable 25 year old!
All the dates I’ve had so far have taken place at my apartment. I have still yet to fully venture out while dressed. So, sadly, something as simple as meeting someone for coffee is not quite an option for me yet.
It’s funny… while in the presence of a potential partner, I find my self COMEPLETELY NATRUALLY just adopting more feminine mannerisms, and speaking in a slightly more feminized voice. After a while I honestly wasn’t even trying, my brain just forced myself to go into full “Ruby-mode”! The guy I’ve been seeing seems to be very appreciative of my company, which is an indescribable feeling, especially after all my worrying and self-doubts. A lot of insecurities I had quickly started melting away..
So, just a huge reminder to everyone that most of the time, we are are own worst critics!!
Morning Ruby,
I’ve been on FL for many years trying to find a man with little success. My ability to meet someone is very narrow and life also has a funny way of creating obsticles to meeting someone. No one can host and I’ll never invite a stranger into my home. Just like any girl, you’d never do that for safety reasons. I also expect a guy to wine and dine me, it’s not dutch, no different when a guy takes a girl out for drinks or dinner.
I’ve met a few strangers and given car head hoping that it might turn into something longer term, sort of like proof of concept, total BS of course.
It’s a rabbit hole that you will dig yourself deeper into.
Be Safe n Stay Healthy
Em
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