Looking For A Partner As A Sissy

Dating and relationships are hard in the best of times and for the most vanilla of people.  I’ve learned this though years of experience, as I suspect many of us have.  Generally, when an interest in sissy play, crossdressing or feminization is added to the mix, everything becomes much more complicated and difficult.

There’s a lot of ignorance surrounding the idea of sissy play and developing any type of relationship when it is involved is a minefield.  For me, I’ve usually kept my interests to myself; I’ve tried integrating into relationships: friends with benefits, long term partnerships, or even just a one nighter, and it’s always so tricky.

Let’s discuss how to try and find a supportive partner as a sissy.  What can you do and what’s important to consider?

Starting out afresh

I think the best place to start is to figure out the type of relationship you’re looking for.  Whatever you’re looking for, there are always a few obvious places to look; dating apps, local bars or your friend network, just to name a few.  Given that you’re going to be looking for someone comfortable with sissy play, feminization or dating a crossdresser, I’m going to venture a guess that online dating is going to the be first port of call.

Dating Apps or websites

So, there are the ‘traditional’ choices; Tinder, OK Cupid, Bumble, etc.  I wouldn’t go with these for our specific purpose.  Firstly, because they are so widely used, people aren’t too willing to share a lot on their own profiles.  Because of the popularity of them, and the fact that they link to your location, you also won’t know who might see your sissy self; imagine the knowing smiles and glances at the supermarket or on the train.

Kink Sites or forums

I’ve found a few websites and apps which cater to us, with varying degrees of success.  I’ve been told that Grindr is a good place to start, but having a few gay friends, and knowing their stories; this has never seemed like my cup of tea.  I do know of a few others though.

• SissyMeet.com; at first glance this seems like a winner, but don’t be deceived, it isn’t.  Lots of the accounts are bots which send your profile messages.  This entices you to buy a membership to read their messages without a hope of ever meeting someone.

• ClubCrossdressing.com; This was better, as more of the users are genuine and spread out globally.  Reviews online are also positive.  Downside, you’ve got to pay to do anything beyond create a profile.  Also, it’s nearly impossible to delete the account, which is worrying.

• Reddit, r/sissypersonals; So, the big pro here is that it’s free.  However, after clicking around a bit, I got the feeling that it was mostly meant for sissys to get a thrill from posting a sexy photo or two and maybe getting a few messages.

Planning a meeting

Once you’ve found a potential partner, you can begin to think about meeting up and getting to know each other more intimately.  I’ve got a few pieces of advice about how to do this constructively; spotting red flags is essential at this point.  Chatting online to get acquainted in cyberspace is one thing; transferring that to the real world is quite another.

I wouldn’t want to meet any potential playmate in my sissy role for the first time.  Arranging a casual meeting, in normal attire, at a public place is the best first step.  It should appear to others as if two friends are meeting to hang out, or if your preferred dom is female, a first date.  During this meeting, you’ll be able to gauge their behavior, their social skills and you can keep an eye out for red flags.

One experience I’ve had, which I can share briefly, is that I got acquainted online with someone.  For the first day or two of chatting online, everything seemed fine.  However, anytime I suggested that we try to meet up in person, they’d seem to dismiss ideas about where to go. I’d suggest a coffee shop or bar in a nearby town, and they’d dismiss it, saying that I wouldn’t be able to be my slutty self in such a place.  They’d counter by suggesting a walk through some secluded woods or coming over to their place.  Needless to say, all big red flags.

Knowing if someone is the right fit

When engaging in a relationship as your sissy self, some of the big warning signs that things could or are going wrong can be obvious or more opaque.  The most important thing is to remember that even as a sissy or submissive, you must retain the power to say stop.  Anyone who lords their dom role, or makes demands of you could cause problems, even for a single night.  I’d like to let you know what some of my big red flags are:

• Shaming: A lot of sissies are into humiliation, or have similar fantasies.  But remember, those are things that you’d consent to.  I think shaming is different; making you feel worthless for something you have done or want to do.  Phrases like ‘if you were a good sissy…’ are a marker.

• Unconditional demands: Keep an ear open if your partner uses the imperative too often.  Commands that end with the word Now!

• Setting their own red lines: A partner who makes too many rules prohibiting things is a big no no for me.  “I don’t want you to…”, “You cannot…”.  Being a sissy is about encouraging femininity and being rewarded for doing so; not about preventing a partner from doing things that the other partner might not like.

Beginning a relationship or initiating a hook up as a sissy can be very tricky.  Knowing your boundaries, being confident and secure in your role, and trusting your partner are all essential to enjoy each other in such a role play or relationship.

Finding a suitable partner is very difficult and I’d like to wish all of you the best of luck when doing so.  I hope my advice about red flags and pain points is helpful. I’d like to hear your advice as well; I’m always learning and I’m sure our audience is as well.