How to have sex with a trans woman | Riley J. Dennis

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– Hey everyone, so today I’m gonna teach you how to have sex with a trans woman. Obviously we’re on YouTube here, so nothing’s gonna be too graphic. I’m just gonna show you some toys and talk about some of the methods that you can use. And we’re gonna talk about some of the changes that happen to a trans woman’s body as she goes through a physical transition. So it’ll be broadly split into four categories, one for stuff that that anyone can do, one for trans women who haven’t started any kind of hormone therapy, one for trans women who are on hormone therapy but have not had bottom surgery, and one for trans women who have had bottom surgery. Because obviously when you’re having sex, different genitals act in different ways and what hormones you have running through your body affect the way those genitals work.

And that’s not to say that any of those are better or worse than others, just that they all function differently. And so if you’re a trans woman looking to have sex, this might be helpful or interesting to you. But also, if you have a partner who’s a trans woman, but you’ve never had sex with a trans woman before and you’re just curious about some of the different things you can do, hopefully this will be helpful for you. I can’t really help you find a trans woman to have sex with, that’s on you. I mean, don’t go looking for a trans woman to have sex with, I feel like that’s really fetishizing. But just, if you’re in the scenario where you wanna have sex with a trans woman, but you’re unsure about genitals or hormones or what different toys you can use, that makes sense because a lot of people haven’t had experience having sex with people who aren’t cis men or cis women.

So that’s what I’m here for today, to help you learn about sex with people who aren’t cis. I also wanna point out that not all trans women physically transition in the same way, so some trans women might be fine not being on HRT or having bottom surgery, some might be happy just having HRT, and some will really want to have HRT and bottom surgery, so it completely depends and there’s no beginning, start, middle, end.

It’s all very individual and down to the person. And also, social transitioning can happen separately from physical transitioning. So someone can socially transition before they get on hormones, or someone might start hormones before they socially transition. I just want everyone to be aware of that, that not every trans woman will go through every single one of these stages. Everyone’s physical transition looks different. So before we get started, I wanna let you all know that this video is sponsored by Adam & Eve. So if you see any toys in this video that you like, you can go to adamandeve.com and use the offer code Riley to get 50% off of almost any one item and free shipping on your entire order in the US and Canada.

And just a huge thanks to Adam & Eve for sponsoring this video, because this is stuff that I really wanna talk about. And with Adam & Eve’s help, I’m able to do that. So let’s get into the video. Okay, so the first category we’re going to talk about is stuff that can work for any trans woman. So obviously we’re gonna talk about butt stuff. Because the great thing about butts, is that everyone has one, so it doesn’t matter what kind of genitals you have, if you have a butt, you can use butt toys. This one is called the Booty Bootcamp Training Kit and it’s basically just three levels of butt plugs. So you start with a smaller one. Focus on the butt plug, please. There you go, so you start with the smaller one, go up to a little bit bigger one, and then go up to a bigger one. Depending on how comfortable you are with them, it’s a really great way to get started with anal, to work with something small and then make your way up.

And just remember to use a ton, a ton, a ton of lube. Because it might be a little bit uncomfortable at first, but it shouldn’t hurt. So that is one thing that I would suggest trying. There’s also just a ton of other butt plug options. I personally like this one, that I talked about in the video before. It’s like a little metal one with a rose on the end. Just a nice, cute, little feminine butt plug. So this butt plug might look similar to the last one, but it actually has a cable coming out of it because it can plug into this little remote that has a button that makes this one vibrate. So if you’ve used the other butt plugs and you like them and you wanna try something that vibrates a little bit more, this one’s called the My First Silicone Surge.

And you can use the remote or you can give it to someone else, depending on whether you’re masturbating or having sex. But it’s just a little way to step up your butt plug game from just normal butt plugs to vibrating butt plugs. And regardless of where the trans woman is in her transition, you can always do BDSM stuff.

Obviously that depends on the individual, and if she likes BDSM stuff, and if you like BDSM stuff. Any kind of whipping kind of stuff, doesn’t matter what kind of genitals you have. Any bondage type things, like so you can strap someone to a bed or strap their arms and legs together. All of that can be used regardless of your genitals. Also, nipple play stuff can be used with anyone. I don’t have any examples on me, but like nipple clamps and that sort of thing.

Again, this all depends on what you like and what your partner likes, so you should be talking to your partner about what she likes, what she doesn’t like, and figure all that out and match that with the stuff in this video. Next up we’re gonna talk about some toys for trans women who haven’t started hormones and haven’t had bottom surgery. So this one is called the Optix Main Squeeze. It’s basically a masturbator stroker kind of toy.

So you unscrew this part and you can stick your penis in here. I recommend this one because it’s not like a highly gendered product, which I feel like can make a lot of trans women dysphoric. And the entry is just the generic hole, it doesn’t look like labia or anything, which again, could cause dysphoria for some trans women. And it’s just a great little toy. You use some lube, you can push on this side to get more pressure. I think it’s a great place to start in terms of strokers and masturbators. And honestly, it’s not only for masturbating, you can use these during sex for sure. You can use this on someone else if they’re not comfortable having penetrative sex. Another option, depending on what you’re into is the Cyber Skin Stealth. So it’s the same kind of vibe, you just unscrew the thing and then you can put your penis in here. It mostly just depends on what aesthetic you want, but this one also has a thing to stick it to the wall in the shower if you want.

And so those are some great options if you’re with a trans woman who hasn’t started hormones or had bottom surgery or anything. But again, what other sex acts you can do with her are going to depend on what she and you are comfortable with. And it depends on what genitals you have. So some trans women really enjoy receiving anal sex, which you can do with either your penis or a strap on.

Some trans women aren’t huge on penetrative sex, which is why I would recommend the strokers. But if she’s into penetrative sex, then that’s also something you could do, depending on what genitals you have. The main point here is just communication. Talk to your partner about what she likes. And if she hasn’t quite figured it out yet, then talk about if you can experiment with stuff. Ask her if she would like oral sex or if she would like this toy or that toy, or how she feels about penetrative sex. The next category we’re gonna talk about is trans women who have been on hormones for awhile but haven’t not had bottom surgery. So if you’re unaware, trans women who are on HRT, hormone replacement therapy, their penis will start to act and look a lot different, because girl dick is not the same as guy dick. On estrogen, the penis and testicles will both tend to get smaller, and the penis won’t really get hard in the same way it did before.

Because it’s acting less like a penis and more like a big clitoris. So if you think of it more like a big clitoris, you can understand better how it works. So obviously this depends and varies for everyone on HRT, but for a lot of trans women, it stops being so pleasurable to have it stroked like a penis, and is more pleasurable to feel vibrations and rubbing up against it. So one thing that I would highly recommend for that is a massage wand like this one or like this one.

This one is obviously smaller and more compact, and it’s easier to put in your bag or something, or to hide in a drawer. But this one, if you’re okay having sex toys out in about in your house, this kind of wand is usually just more powerful and can create more vibrations, which you usually need for what is basically a big clitoris. And like a clitoris, it’s gonna have different areas that feel good or don’t feel good. So you can use one of these to push around on different parts of the penis and you can see where it feels good, whether that’s on the testicles or the shaft or the head, it can really vary. One side can be more sensitive than the other. In a lot of ways, it’s like a clit. And so I would definitely recommend a wand like one of these.

Some trans women on HRT can still have penetrative sex, but not all of them can. So your safest bet is probably some kind of vibrator-related sex. But you can always talk about penetrative sex with her and see if that’s an option. And again, there’s all the stuff that we discussed earlier, like butt stuff and BDSM stuff. Also one thing you might wanna try is that if she doesn’t like having penetrative sex or can’t have penetrative sex, you could always try a strap on. Because like with this one, it kind of suction cups itself to the mound right above your genitals.

And like I said, a penis on HRT is much softer and smaller, and so it doesn’t really get in the way as much. So if you still enjoy the movements or the feelings of penetrative sex, a strap-on can be a good idea to try. Because I know they’re seen as toys for people with vaginas, but it can also work for a trans woman who is on HRT. So next up we’re gonna talk about having sex with a trans woman who has had bottom surgery. So after bottom surgery, a trans woman has what’s called a neo-vagina. It’s their penis reconstructed back into a vagina and a clitoris, so it behaves basically like a cis woman’s vagina and clitoris.

And in that way, there’s several things you can do. You can have penetrative sex, or you can focus on the clitoris a lot, which will probably give more stimulation. But again, depends on the person. Some people enjoy penetrative sex more. So one thing I would recommend trying is a little vibe like this. I swear, people with vaginas get the cutest toys. This one is called the Izzy Clitoral Vibe. It’s got a little power button down here and you can just turn it on and then it’s just a cute little vibrator that has a little end right here for the clitoris. And it’s USB rechargeable. You could also try something like the Satisfyer range. This is the Satisfyer Penguin. It’s really just super cute, but what it does is so it creates a lot of suction right here and you can put this on her clitoris.

And the nice thing about this is that it doesn’t really look or feel like a normal sex toy. It’s kind of innocuous, you could just have this on your bedside table. But also, it can feel a lot better than a lot of other kinds of sex toys ’cause it’s a different kind of stimulation. So I’d highly recommend this if the trans woman you wanna have sex with does have a clitoris. And if you want a clitoral vibe that can be controlled by someone else, you can try this rechargeable Love Bullet. So it has this piece that I think is a little blown out in the camera, but has little feelers down here for the clitoris, and it has this remote.

This can be great for all sorts of play and for teasing someone, plus the vibrations are surprisingly powerful for such a tiny little thing. And obviously you can use the strap on or any other penetrative sex toys with a trans woman who has a vagina. But if you’ve been watching this and thinking, why isn’t there a toy that can do clitoral, vaginal, and anal stimulation, I have a rabbit for you. This is called the Happy Rabbit Triple Vibrator. So this one’s a bit of a doozy. You probably need a bit of warming up to it, but it can provide some incredible stimulations. So the large part here goes into the vagina, this part tickles the clitoris, and this part goes into the anus. And then the whole things vibrates and it is honestly an experience. So this could definitely be something to try with a trans woman who has a vagina. And yeah, that’s basically it. So just keep in mind that the most important thing here is going to be communication.

If you’re going to have sex with a trans woman, she probably knows best what can pleasure her, so ask her about it. Hopefully this can just give you an idea of what toys you can use at different levels of physical transition. If you wanna have sex with a trans woman, but you’re nervous about it, don’t worry, I’m sure it’s going to be fine. Just be very respectful and communicative. And maybe you show her this video and ask what stuff from here sounds good to her. And if you are a trans woman, I hope you can use some of these toys or tips to improve your own sex life.

And if you have any recommendations, feel free to leave them below. I’m not the master of sex or anything. I’m sure there’s stuff I missed and stuff that trans women enjoy that I haven’t touched on. Because I’m just one person and I can’t possibly speak for all trans women, you know? These are just some options for you. And remember that if you like anything you saw here today, you can go to Adamandeve.com and use the code Riley to get 50% off of almost any one item and free shipping in the US and Canada. Anyways, thanks so much for watching and I’ll see you next time. (upbeat music).

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