Dating Transpeople 101

It occurred to me, several weeks after I made the two anal sex posts, that I covered fucking before I wrote a guide about actually dating transpeople. In that way, my blog mirrors much more of my life than I intended.

Hello all, and welcome back to The Broke-Ass Transwoman. In case the title did not clarify enough, I am Sephie, your local poor af blogger, transwoman, gamer and consummate slut, here to give you advice straight from the knee-deep cess pool that is my brain! While I am possibly as qualified to speak on this subject as a slug is for giving advice on Super Mario 64 speed runs, not knowing anything about a subject doesn’t stop politicians from telling women what they can do with their bodies and therefore won’t stop me. We’re living the dream here, people–suspend that belief with me.

Because today, dear reader–it’s going to be an interactive event. Yes, you heard me. This is gonna be hands on. Real getting your hands dirty kind of stuff. Why?

Because you’re taking me on a date.

I know, I know–you’re wondering what you did to deserve this five-foot-eight tall pile of perverted thoughts, questionable morals, and even more questionable taste in clothing. How did you, reader, get so lucky? Well, the truth is that you’re here and you’re available; so you’re already miles above everyone I’ve wanted to date. Granted, you can refuse (consent is important), but if you continue reading–we’re going on a date. It’s happening. Got reservations and errythangggg.

But before we go on this clearly life-altering date, how do you prepare? How do you ready your brain for going on a date with a wondrous, stupendous, gorgeous transwoman whose hobbies include eating ramen straight from the pot half-naked on her couch?

1. Stop thinking this is weird.

You’re going on a date with a transperson. I get it, it might be new for you. You might feel strange that you’re getting tingly in your nether bits over a transperson in general. That might be scary.

That’s fine and fair, but is 1000% your problem to deal with for now, not hers, his, or theirs. If you spend the entire night saying how “different” and “strange” this is for you, you’re going to accomplish nothing but making them feel alienated as fuck.

This is not to say that trepidation isn’t natural. It’s understandable, given that society views transpeople, especially transwomen, as boogeymen (heavy on the man, ugh). However, if you’ve already gone far enough down this road that you’ve agreed to the date, try to let that take the back seat. If you have concerns, maybe try to talk about them before the actual date happens. While we’re on this date, it’s better to just think about it like it’s any other date you’ve gone on with a cis-person. Which is to say potentially horrible, but you don’t know that yet!

I’m a keeper. Trust.

2. Your apartment is not a date

This might strike you as a little odd. Sure, chilling in your apartment might not be a great date, but like, you can make dinner, light a few candles or whatever, right?


Here’s the deal–while that’s all well and fucking good for cis-women, you know what transpeople are used to being? Dirty secrets that never get to meet your family, friends, or be seen with you outside the place you jerk off in. For a lot of people, we’re big, wide-mouthed blow-up dolls to be deflated and put away in the shame corner whenever you’re done being dick shallow inside us.

I can count on my left hand the number of partners I’ve had who were comfortable with being seen with me outside, and believe me, that burns, and not in the fun, playing-with-wax kind of way.

While there are some transpeople who may not be out yet, or who are just not comfortable presenting as such outside a private dwelling right now, many of us would prefer to go out. In public. Where there’s people. It’s a good litmus test to see if you’re a decent person, or if we’re just some shameful secret you want to keep in the dark.


Alright. So you’ve done some mental prep work now. You’re ready to take my bright, shiny ass out on a date. What else could you possibly need?

A lot.

3. Prepare for stares

So, we start our date–I look hot, by the way, just want to make that clear–and we go to a restaurant. While we’re there, we draw eyes.

A lot of them. A disturbing amount, and they’re not all friendly.

I am doing an excellent job selling dating me and those like me, but realistically, there is a big possibility that you will get stared at on a date with a transperson. As much as I personally like to imagine it’s because of my stunning good looks, it’s usually because people are judgmental douchewaffles.

You need to keep in mind that you will likely never see these people again, and their opinions don’t matter. Take the staring in stride, and instead of viewing it with shame, see it as standing in the light they’re too afraid to have shine on them.

On the same token…

4. Prepare to leave if things get bad

As much as I encourage ignoring the stares, please be at least a little bit aware of them. Staring can be harmless, but harassment isn’t. If people shout at you or start looking like they’re about to do violence to us, GTFO. Do not pass go. Do not collect $100.

I generally find that most people are content to stare and whisper under their breath, but that isn’t always the case. Be safe, both for you and your date partner–which here, is me. Please don’t get us killed by being too stubborn to find a new restaurant, I don’t think they have great menus in hell.

Alright, so we’re in the restaurant–no one has bothered us. We’re good. We’re chatting, and most importantly, I’m hella hot. Wearing a slinky little red number. My hair is totally doing something nice and not just sticking from the sides of my head like Cynthia from Rugrats.

Just wanted to give you another reminder–as long as I’m making up this fiction, damn straight Imma look good.

So, date goes well, and I’m dead sexy and you think that you maaaybe want to take this further. We get back to your place, and things start getting tense.

What should you know?

5. Now is the time to raise concerns

I know I discouraged talking about all your nerves earlier in the date–this is not because feeling these nerves is bad, but it really, really bogs down a date when all the other person an do is talk about how this is “their first time with someone like you” and “I’m so goddamn nervous”.

However, you should ALWAYS discuss boundaries and fears before being with a partner. I don’t care if you think it will ruin the mood–the mood is gonna get ruined by mediocre sex if you both don’t have the same expectations, or if you can’t get it up because you’re freaking out. If this is new to you, please talk about this stuff before you do the deed.


6. You don’t need to fuck on the first date


This may seem obvious and more me telling myself than anything, but if you have serious interest in a transperson, you do not have to fuck on the first date. Often, at least in my experience, fucking then tends to mean you’re a) just after sex b) don’t want me for anything else. Granted, I’ll still throw my ass back anyway, but not everyone is a shameless slut like me.

There is nothing innately wrong with fucking on the first date. However, I do know at this point in my life it usually means that nothing serious will come from it, which may be fine if that’s what you and your partner want.

Also, we could totally fuck and you could still call me in the morning–a novel goddamn concept in my life, believe me.

With all that said, there’s one important thing to remember through all of this.


Seriously–no matter who you’re dating: cis, trans, non-binary, or a soul sucking succubus from hell, the important thing is to remember that you’re here to enjoy yourself. If you’re not, there’s a good chance they’re not the right person to be hanging out with.

That all said, this date was awesome and make sure you call me. ;*

You are gonna call me, right?

…wait, where the fuck did you go? DID YOU LEAVE? GOD FUCKING DAMN IT.

T________T Back to OkCupid, I guess. 


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