Trans Women + Sex = Awesome

Introduction and Terminology

Part One: So you’re gonna have sex with a trans woman

Part Two: So you’re a trans woman who wants to get off

Part Three: Sex Toys!

General Introduction

When it comes to popular culture and human sexuality, few bodies are lower on the sexual totem pole than trans women. We’re not viewed too positively, us trans women: exploitative and problematic “she-male” porn; sitcoms and movies joking about discovering the woman a character was dating was “really” a man; Craigslist personal encounters demanding “passable” trans women, conflating trans people and cross-dressers; the list goes on and on.

Trans Women + Sex = Awesome is written in the hopes of combating all that cultural bullshit, at least a little bit. Specifically, I hope to address two major topics:

  1. Physical intimacy with trans women
  2. Physical intimacy as trans women, both solo and with partners

There will definitely be some overlap between 1 and 2, and I may get a little off topic on occasion, but everything is written with those two major focus areas in mind.

Before we get started, a few ground rules and language notes:

Language

I’m going to use language the best way I know how, and with as much transparency as I can. Some notes on language:

  • Trans Woman: Used throughout this guide to mean “someone who was assigned male at birth, but doesn’t identity as male and identifies at least sorta-kinda-maybe as female.” This hypothetical person may or may not have undergone any medical intervention (surgery, hormones, etc), although I’ll talk a little about how those interventions can change one’s body
  • Cis or Cisgender: A word used as an antonym/opposite of trans. A cis person is someone who feels at least mostly comfortable in the gender they were assigned.
  • Sex (the act): Physical intimacy. Hooking up. Sexytime. May or may not include any penetration or genital contact. YMMV.
  • Body Parts: I’m going to mostly use generally recognizable names for body parts, including penis/cock/dick, testicals/scrotum, etc. Some trans women do not like these names for themselves, and I’ll include some specific notes on what I and other trans women sometimes like instead.

If you or someone you know disagree with these definitions, it doesn’t inherently mean one of us is right and the other is wrong. It means language is complicated, and language around gender and sexuality is developing. (See Disclaimers, below.)

Disclaimers

I do not claim to speak on behalf of All Trans Women. If you are a trans woman and disagree with something in this guide, please let me know so I can try to make it more comprehensive. If you are hooking up with a trans woman and they say something which disagrees with a part or all of this guide, trust them to know their own bodies! (And, if appropriate, please email me at rebecca@rebeccakling.com to let me know where I fucked up, so I can do a better job.)

 I am writing about trans women because I am one. If any trans men, or genderqueer folks, or even other trans women, want to write a similar guide from their perspective, please do so! I’m trying to be as transparent as possible about my experiences, but don’t want this guide to be seen as the end-all, be-all of trans sex related knowledge.

I’ll also be writing most of this guide from the perspective of a pre- or non-operative trans woman (that is, a trans woman with a penis) because, well, I’ve had one for most of my life. That’s also usually what people mean when they talk about “having sex with trans women”: they mean trans women with cocks. Of course, I started this guide before I had gender reassignment surgery, but finished it after I had surgery, so check back soon for updates and post-surgery thoughts on sex and sexuality…

Other Resources

I cannot recommend Fucking Trans Women highly enough. It’s an 80+ page zine, $5 as a PDF download and $8 print copy, that explores many of the same issues as this guide with much more detail and pretty pictures. Definitely worth the price of admission.

There are a few good blog posts I’ve found:

If you know of other good resources, please let me know and I’ll include ‘em here. (Are you noticing a pattern? I don’t pretend to know everything!)

 

Part One: So You’re Going To Have Sex With A Trans Woman

The idea of having sex with a trans woman carries a lot of cultural baggage. Celebrities are disproportionately shamed or ridiculed when they’re discovered with trans sex workers. TV shows go out of their way to poke fun at characters who even consider dating a trans woman. In court, trans women are accused leading men on, or tricking them.

Fuck that.

 This section of Trans Women + Sex = Awesome is directed primarily at cis folks who want to know more about having sex with trans women in a way that is not fetishizing, objectifying, or engaging in transphobic bullshit. Hopefully, this section will also have some value for trans women, but you’re not my primary audience right now.

Note: This section contains some overlap with the section directed at trans women. The phrasing has been tweaked in a few places, but don’t be surprised if some of the information seems familiar.

About What Not To Do

Before we get to how you should interact with your trans female partner, let’s talk about some stuff to avoid. Hopefully, none of these should be too surprising, and they should fit with what you’re already doing with any cis partners. Because trans women are people, first and foremost, above and beyond our trans-ness. We deserve the same respect any other partner deserves. I’ve joked that, from the partner’s perspective, this guide could be reduced to two main points:

  1. Don’t Make Assumptions
  2. Don’t Be A Jerk

But that’s a little simplistic, so lets go into some specifics.

Don’t Make Assumptions About Language

I’m going to talk more about how to approach this topic in a moment, but don’t assume your trans partner will like specific terms for themselves or their body parts. Some trans women will like talking about their genitalia using the word “cock”; others might prefer she-cock or lady-cock or bio-cock; some like strapless (as opposed to a strap-on dildo); some like clit; some will like something else entirely. And it might change from day to day, or act to act.

Don’t Make Assumptions About Sexual Acts

Pretty much the same as above. Some trans women are going to love fucking you in the ass with their strapless bio-cock. Some might not love it, but will be willing to do it for you. Some won’t want to do it, period. Why a trans woman does or doesn’t want to do something might have to do with her trans identity, or it might not. Or maybe she’s just not into that act on that day.

Don’t Put Your Shit On Us

This is a tough one for many people to wrap their mind around. If you’re hooking up with a trans woman for the first time, it is entirely legit for you to have feelings of uncertainty or nervousness. You’ve been told your whole life that trans women are icky and to be pitied (at best) or beaten up and killed (at worst). Your complex feelings are legitimate and important for you to process. But not with your partner. It is unfair and unreasonable of you to ask your partner to play therapist.

Statements like, “I’ve never been with a body like yours,” may be entirely true and seem neutral in your mind. But, to a trans woman, it can come across as “…because you’re a freak.” Likewise for “I’m not sure what to do with [body part],” as well as “I’m really nervous about [sexual act] because it’s new to me.”

None of which is to say you can’t feel those things, or that you should hesitate to express discomfort with your partner. But there’s a fine line between, “I’m unsure about getting fucked up the ass because I’ve never done it before and don’t want to hurt myself,” and “I’m unsure about getting fucked up the ass because I’ve never been with a trans woman before and I’m questioning my sexuality.”

The first concern is very much something you should share with your partner, whether or not they’re trans. The second statement is something you should discuss with your therapist, best friend, bartender, priest, etc, not with your trans partner.

Lets look at some possible emotions, and what you should or shouldn’t say.

 

Situation

Icky Thing to Say

Awesome Thing to Say

You’ve never been with a penis-having woman before, and are nervous about how you’re going to react in the midst of sexytime.

“I’ve never been with a trans woman before, and I’m a little nervous I might freak out.”

“Can we take things slow?”

You just finished an amazing night of sex, and want to share your excitement with your trans partner.

“Wow! I guess sex with trans women can be fun!”

“That was amazing! I can’t wait to see you again.”

You have a question about your partner and their sexual desire.

“I heard some trans women don’t like to use their penis to fuck their partners. Do you?”

“What sort of things sound fun to you? I’d love to get fucked by you.”

 

As always, these are guidelines and not hard-and-fast rules. Not every trans woman is going to have the same attitude or desire the same type of communication. Likewise, the above is sort of over the top, and shouldn’t be viewed as scripts you need to recite word for word. But, in general, highlighting the difference or freakiness of your trans partner is not a great idea. Instead, think about the core question or emotion you want to convey, and focus on that.

About What To Do

I hope I haven’t scared you away with all that ‘what not to do’ stuff! I promise we’re not that scary, it’s just that many trans women (myself included) have been physically or emotionally hurt by someone who made unwarranted assumptions about our bodies and our identity. Even if you stop reading this guide right now, I want you to keep those ‘what not to do’s in mind. Pretty please with a cherry on top!

Still with me? Good. Lets get to the fun stuff.

Trans Women’s Bodies Are Just As Normal As Any Other Body

There’s this idea that trans women are somehow inherently different than everyone else, when it comes to sex. You see it in porn. You see it in fetish literature. You see it, I admit, implicitly in the premise of a guide like this: Trans women are different, and you somehow need extra knowledge to have sex with us.

I don’t subscribe to that. You could do much worse than following that advice from earlier:

  1. Don’t Make Assumptions
  2. Don’t Be A Jerk

That’s pretty good advice for having sex with any body, trans or cis. (And pretty good advice for non-sexual interactions, come to think of it.) But, because of all that cultural baggage, it’s helpful to talk about how trans women’s bodies are unique, and have some things in mind when approaching fun sexytime with a trans woman.

Hormones

There are two primary sex-related hormones: testosterone (the primary ‘male’ hormone) and estrogen (the primary ‘female’ hormone). Both men and women have a mix of both, but the levels are different. If a trans woman is on hormones, (AKA hormone replacement therapy) she’s probably on estrogen and/or testosterone blockers. Estrogen and testosterone blockers can have many effects, but the major ones we’re interested in may include:

  • Breast growth
  • General fat distribution (largely to butt/boobs, from belly)
  • Muscle reduction (testosterone fuels muscle growth)
  • Softening of skin texture
  • Reduction in sperm production
  • Possible increase in skin sensitivity
  • Possible reduction in ability to get/maintain an erection
  • Possible reduction in libido

Unless you’re pretty intimate already, it’s a little forward/rude to ask your trans woman partner about her hormone levels. You don’t really need to know whether or not she is on hormones in order to have sex with her. Much better to ask what acts they do/don’t like, and what body parts you should/shouldn’t touch, just like you would (I hope!) with any other partner.

So while it’s helpful to be aware of hormones, and how they can impact trans women, you shouldn’t feel worried about the hormone status of your partner. Some trans women are on hormones, some aren’t, and neither really impacts how you should treat your partner during sexytime.

Penis. Cock. She-cock. Lady-cock. Bio-cock. Clit. Strapless.

Having a penis is perhaps the most visible differentiator between trans and cis women. For every other physical characteristic that might be called “trans,” you can find a cis woman who is just as tall, or hairy, or whatever. But a penis is generally The Thing People Mean When Talking About Sex With Trans Women.

(Phew, that was a lot of capital letters…)

Fucking Trans Women is THE definitive guide on the anatomy of the cock as it relates to trans women. I won’t go into nearly as much depth (tee hee!) but I will touch on a few things (tee hee!).

Some trans women like using their cock during sexytime. Some don’t. Since genitals are so linked with sex and gender in our culture, there are some trans women who find that using their penis during sex is too inextricably linked with ‘male’ness. Before getting into below-the-belt action with your trans partner, here are some questions to consider:

  • What do you like your parts to be called? I call mine ___________
  • What feels good?
  • Is there anywhere I definitely should or shouldn’t touch?

This may not seem super-sexy, but a sobbing trans woman – traumatized because you didn’t ask if she liked receiving blowjobs – isn’t particularly sexy, either. Unless you’re into that sort of thing. In which case, you should still ask first.

 A trans woman may not want her genitalia touched or played with, and this may have nothing to do with you. So don’t take it personally.

Hormones change how the cock experiences sensation, but not so drastically that you should over-think things. Let’s say your trans lady does want you to touch her cock. Ask her how hard, how much, and so on. I know lots of trans women (myself included) who enjoy having their cocks played with, but neeeeeeeeed lube. For me, it’s kinda like a clit in that regard: Pressure/sensation/vibration/friction is all awesome, but only if it starts gentle and if I’m allowed to back off when it gets to be too much.

Don’t stress about erections or ejaculation. We have an expectation that an erect penis is a (sexually) happy penis, and a flaccid penis is a (sexually) unhappy penis. When on estrogen, some trans women have a more difficult time achieving or maintaining an erection. Don’t take this as an ironclad barometer of your partner’s enjoyment! Check in with her, and see how she’s doing. Some trans women aren’t going to get hard, no matter how much you try; if you’re waiting for an erection, you’re going to be disappointed. Some trans women will get hard, but it may not mean as much to their sexual enjoyment as it would to a stereotypical cis man. There are lots of fun ways a flaccid cock can be played with, and lots of nerve endings that still deserve stimulation!

All of the above goes for ejaculations as well: Some trans women, particularly those who are on hormones, aren’t going to ejaculate in the same way a cis man might. Some trans women, even those who are on hormones, may still ejaculate. This is another area where checking in with your partner should take higher priority than looking for expected (cis-centric) ideas of orgasm, completion, finale, or whatever you want to call it.

Sperm: The Babymaker. Hormone replacement therapy – estrogen and/or testosterone blockers – will definitely decrease a trans woman’s sperm count. Unfortunately, that’s not a guarantee that a trans woman will produce no sperm. If you’re planning to have sex with a trans woman, you should still use other birth control methods you find appropriate: condoms, birth control pills or an IUD (if you’re a cis woman), etc.

Penetrative Sex: Being Fucked By A Trans Woman

All those penis possibilities – will it get erect? what should I call it? what sensations feel good? ahh!!! – mean that some trans women aren’t going to be interested in penetrative sex as the penetrator. It may not be physically possible given their personal anatomy. It may be physically possible but not feel emotionally good. It may be physically possible but not feel physically good. If you want your trans partner to penetrate you with her bio-cock, be open and honest about it, and be ready to take ‘no’ for an answer.

There are lots of guides on the Internet for how to get fucked by a penis, in whichever orifice you may desire. I won’t go into much detail, except to say that difficulties maintaining erections mean that positions with the trans woman underneath you – sitting or laying on her back – may make it easier.

You can also check out the the other sections of this guide for thoughts on having sex as a trans woman, as well as toys (like strap-ons) that may be of interest to partners of trans women.

Penetrative Sex: Fucking a Trans Woman

Urban Dictionary defines “fucking” as:

  1. The man’s erect penis rapidly thrusting back and forth in the woman’s vagina (or an anus).
  2. The woman’s vagina (or an anus) rubbing up and down on the man’s erect penis.
  3. The action of the penis penetrating an object or a person.
  4. An insertion of the vagina that is pleasing to the woman.

(Sidenote: Ain’t the Internet great?)

We’re gonna use a broader definition of “fucking” than Urban Dictionary, particularly because not all women have vaginas. Hopefully that’s a “duh” by this point. We will, however, cover a few different ways trans women can be penetrated, all under the umbrella heading of “fucking.”

What What (In the Butt)

There are lots of guides about how to successfully have anal. Go read them. The fact that trans women have a prostate means anal can be extra fun. (Take that, cis women!) Estrogen or testosterone blockers can cause the prostate to shrink, but there’s nothing too different about having anal sex with a trans woman than with anyone else. As such, the only notes I’ll give are:

  • Anal play can simply be putting pressure or vibration on the outside of the anus, with zero penetration.
  • If you do decide to experiment with penetration, go slow, especially the first few times
  • Use lube. Lots. More than you think you need.
  • Allow the person being penetrated to control the speed for the first few times. Positions with them on top, or things like doggy style, make this easier
  • Did I mention using ALL the lube? Put down a towel and make a mess.

Still looking for more info? Head on over to Early to Bed’s Anal Sex Dos and Don’ts page.

Muffing

This is a term, popularized by Fucking Trans Women, for inserting a finger, small dildo, or small vibrator into one or both of the inguinal canals of a trans woman. Of course, since I can almost promise “inguinal canal” is not something covered in sex ed, the previous sentence may not be helpful without some explanation.

The inguinal canals are cavities or chambers (Fucking Trans Women calls them “pockets”) on either side of the groin, behind the scrotum and testicles. They’re where the testicles hung out (pun slightly intended) before they dropped. The inguinal canals are sealed by the skin of the groin and scrotum, but they can be reached and stimulated by inverting the skin of the scrotum and (gently!) pushing it up toward the pelvic cavity.

Check out Fucking Trans Women for some nifty diagrams, and have fun experimenting.

Disclaimer Number One: Lots of trans women aren’t familiar with muffing (I wasn’t, before reading Fucking Trans Women), so this may be a term that your partner won’t know. It can also be performed on any body with a penis, so cis men should feel free to experiment with it, too!

Disclaimer Number Two: Muffing should not hurt if done correctly.

Kangarooing (or ‘Rooing)

Writing this guide has been tons of fun, if for no other reason than it gave me an excuse to talk about sex with my friends. (As if I needed an excuse…) One friend, while reading a draft of this section, mentioned a sex act I wasn’t familiar with. Here’s how they described it:

[I can be stimulated] at the base of my penis, just behind my scrotum and just ‘below’ my prostate. It’s basically in the exact spot where a vagina would be, which makes a lot of sense if you think about ‘sex differentiation’ and hormones and development and such (there are a lot of homologous structures).

In other words, this area is right below the scrotum, but not quite down to the perineum (also called the taint). You’re inverting the loose skin of the scrotum up into the open space of the pelvis, beneath/behind the balls and penis.  After some research, my friend discovered that this act is entering the deep perineal pouch, and stimulates the bulb of the penis.

Kangarooing is similar to muffing, in that you’re not quite penetrating an open body cavity, as you would be with vaginal or anal sex. But you are inverting loose skin to penetrate an interior body cavity – the inguinal canals with muffing, and the deep perineal pouch with kangarooing – thus stimulating the surrounding nerves in a new and (hopefully!) exciting way.

All the same disclaimers for muffing apply to kangarooing.

Other Fun Sexytime Activities

Having sex can involve lots more than purely penetrative acts. There’s mutual masturbation, oral sex, toys (which I’ll discuss in a later section), and more.  Talk to your partner about whether she’d like you to go down on her, or get her off with your hands (and probably with lube), or spank her ‘till she screams, or spank you ‘till you scream, or any of the countless ways two (or more!) people can have sex.

All of which is to say that, as trans women, we are more than what’s between our legs. (For what it’s worth, the same is true for cis women. Hell, it’s true for anyone.) Fun sexytime can include a lot more than genital contact, and don’t you forget it. After all, “sex with a trans woman” can and should include whatever fun things work for you. Check out Early to Bed’s sex advice page for information on lube, dildos, orgasms, and more.

I will, however, leave you with one more sex act that a friend sent my way, one they felt was particularly suited for trans women. As such, all credit (and blame) should be directed to C.C.

Telescoping (or the Shy Turtle):

This one works best for those whose penis doesn’t get totally hard or does so only reluctantly. If it gets hard or painful, stop. Do not “fight” against a hard penis.

 First push the flaccid penis inside its own skin. Think of this as inverting a balloon. If it starts to get hard or merely curious, the trans woman should relax and breathe until it stops. Keep pushing it inward and upward into the pubis using the middle finger and ring finger, while pulling the sides of the scrotum forward over the glans using the thumb and ring finger. The other hand may need to push everything into place. Keep tightening until the whole setup looks like a large clit, with the sides of the scrotum serving as labia.

At this point the whole setup can be stroked or rubbed like a clit between the index and middle fingers. Gradually pull on the scrotum to enlarge the labia and to pull everything closer in to the body (or possibly some parts even into the inguinal canals). At this point, the whole setup can be penetrated slowly and carefully with a forefinger.

There are many possible variations on this, although it may take practice to keep everything from popping out.

Have fun!

 

Part Two: So You’re A Trans Woman Who Wants to Get Off

Earlier in this guide, I said the following:

The idea of having sex with a trans woman carries a lot of cultural baggage. Celebrities are disproportionately shamed or ridiculed when they’re discovered with trans sex workers. TV shows go out of their way to poke fun at characters who even consider dating a trans woman. In court, trans women are accused leading men on, or tricking them.

Fuck that.

Well, the idea of having sex as a trans woman carries a lot of cultural baggage, too. We’re told that our sole value is as fetish sex objects (at best) or as objects of humor and pity (at worst). We shouldn’t like our bodies, we shouldn’t take pleasure in exploring them, and we certainly shouldn’t have any sort of sexual agency.

 Fuck that. Fuck all that. Fuck it so very much.

This section of Trans Women + Sex = Awesome is directed primarily at trans women who are interested in exploring their bodies and figuring out what they like (and dislike) sexually. Also, for trans women who want to cum. Hard. And repeatedly. Hopefully, this section will also have some value for the cis partners of trans women, but you’re not my primary audience right now.

Note: This section contains some overlap with the section directed at the partners of trans women. The phrasing has been tweaked in a few places, but don’t be surprised if some of the information seems familiar.

We Have Some Shit To Deal With

Due to all the cultural baggage we trans women have foisted upon us, it may be difficult to find a healthy headspace in which to explore ourselves as sexual beings. Julia Serano touched on this concern in Whipping Girl:

When I hit puberty, my newly found attraction to women spilled into my dreams of becoming a girl. For me, sexuality became a strange combination of jealousy, self-loathing, and lust. Because when you isolate an impressionable transgender teen and bombard her with billboard ads baring bikini-clad women and boys’ locker room trash talk about this girl’s tits and that girl’s ass, then she will learn to turn her gender identity into a fetish. (Page 274)

There is nothing wrong with forced-feminization erotica, or with power play in the bedroom, or with humiliation porn. If that’s what gets you off, go for it! But many trans women – myself included! – toyed with those types of fantasies because they touched upon shame we carry within ourselves, rather than because they made us feel good.  It was much easier for me to imagine myself as the male main character in some forced-feminization erotica at Fictionmania than it was to imagine myself as the female main character in anything else. After all, my thinking went, I was never going to transition. Even if I did, I’d never think of myself as attractive. Even if I could somehow manage that, no one else would ever find me attractive. So much easier to use forced-feminization porn to offload the responsibility of my transition to someone else, as well as to implicitly deny that I wanted to be pretty, or sexy, or sexual as a woman.

Is any of this resonating?

I want to steer this back toward sexytime fun, and away from emotional ickiness, but let me say this: My gender is what I say it is. My body means what I say it means. The same is true for you. Please don’t let anyone else – your partner, the porn you watch, the society in which you live – tell you that you are anything other than awesome, fun, sexy, beautiful, hot-Hot-HOT.

Finding A Good Headspace

All that self-love-touchy-feely-bullshit is easier said than done, I know. But I strongly encourage you to set aside time to think about your body and your sense of self as a sexual being. This may or may not mean your sexuality – that is, who you are attracted to – but should definitely include thinking about what you’d like to do to yourself, do with others, and have done to you. Think about what makes you feel good, physically. Exercise? Taking a bath? Standing in front of the mirror, naked, playing drums on your stomach? (That last one may just be me…) Being trans can mean we have body parts we don’t like, or body shapes we wish were very different, but doesn’t mean we can’t enjoy what we do have.

 Here are some questions I’d like you to ask yourself. Take as much or as little time as you need, and think about feeling GOOD!

  • What makes me feel sexy?
  • When do I feel present and comfortable in my body?
  • How can I encourage that feeling of comfort?
  • What is preventing me from feeling present, and good, and comfortable, and sexy?

And some here are some questions that may be a bit more difficult to think about.

  • What part(s) of my body would I not want a sexual partner to see?
  • What part(s) of my body would I not want a sexual partner to touch?
  • What part(s) of my body do I not like to touch?

At this point, I want to repeat something I said earlier: Your body means whatever you say it means. No one else gets to determine that. If something feels icky, don’t do it. But if you think something might feel good, even if it is emotionally fraught, I highly encourage you to experiment with it. Go slow and take care of yourself, but don’t let anyone else tell you what you can and can’t do with your body.

Other Thoughts Before We Get Started

From the time we’re very little, we’re told that boys have a penis and girls have a vagina. Yet many trans women do have penises. (I had one, up until very recently!) As a result, the information we’re given about sex and self-pleasure – whether it’s from sex ed, porn, or friends – is almost guaranteed to be problematic, if not outright harmful or triggering. Even when getting information from sex-positive doctors, we can be told that hormones will lower our libido, that cumming will be more difficult, even that our sexual orientation may shift.

Boooooo!

 Lets see if we can talk about all that jazz in a body-positive, hormone-positive, sex-positive, trans-positive way.

Your Body Means What You Say It Means

I may have mentioned this once or twice before: Your Body Means What You Say It Means.

I repeat it here to remind you that you don’t have to use the same language I use, or use it in the same way. In this guide, I’m going to use generally recognizable names for body parts, including penis/cock/dick, testicals/scrotum, etc. You do not have to use these names for your body parts! Some trans women like talking about their genitalia using the word “cock”; others might prefer she-cock or lady-cock or bio-cock; some like strapless (as opposed to a strap-on dildo); some like clit or cunt; some will like something else entirely. Some will prefer gender neutral pronouns, or feminine pronouns, or maybe even masculine pronouns. You are allowed (encouraged!) to pick what works for you, and to experiment until you find what feels right.

Hormones Are Complicated

One of the frustrating things about being a trans person, of any variety or gender identity, is that there isn’t good data on our life experiences. People trot out so-called facts:

DID YOU KNOW THAT TRANS WOMEN ON ESTROGEN ARE…

  • guaranteed to experience a reduced libido?
  • definitely at a higher risk for breast cancer?
  • probably more likely to be attacked by bears?
  • maybe possibly more likely to enjoy romantic comedies?
  • almost certainly going to be told baseless bullshit by trained medical professionals, without any statistics or studies to back it up?

And yet, if you try to find actual studies to back up any of the above, you will be unable to do so. Which isn’t to say they’re definitely false, but don’t be worried if you’re on estrogen and testosterone blockers and still have a high libido.

For this guide, it doesn’t really matter if you’re on hormones or not. The only things to keep in mind is that going on hormones will change your body, but no one can guarantee exactly how. There are some general expectations – breast growth, muscle reduction, reduction in sperm count, etc – but really no guarantees.

To use myself as an example, I was able to get and maintain an erection all the way until I had gender reassignment surgery, even while on estrogen and testosterone blockers. On the other hand, I know trans women who are on hormones and are no longer able to get or maintain an erection. We both get our hormones from doctors who check our levels regularly, but bodies are complicated and there haven’t been good studies on how hormones affect trans women. If you’re on hormones, use it as an opportunity to explore your body and how it is changing. But stay calm if your body doesn’t change exactly the way you expected, or exactly the way you were told that it would.

Woohoo Masturbation!

At long last, let’s turn toward the most literal form of self-love there is: Masturbation. Masturbating as a trans women is not fundamentally different from masturbating as any other type of person, but it’s also not anything that was discussed in sex ed. If you Google “how to masturbate as a trans person,” you won’t find nothing, but you also won’t find nearly as much helpful information if you simply Google  “how to masturbate.” Which is a bummer if you’re trying to make yourself cum and aren’t comfortable (or cumfortable) reading a post about how men with penises are supposed to masturbate, and reading how women with vaginas masturbate may not be incredibly helpful, either.

 So lets talk about some masturbation options for trans women.

General Thoughts on Masturbation

  • Experiment. Ask yourself if something would feel better while you’re on your front or on your back. With your legs open, or closed. While reading erotica, watching porn, or lost in your own fantasies.
  • Go Slow. There’s no rush, and you can always try again tomorrow if something doesn’t work the way you want it to tonight.

Nothing Wrong Being Traditional

Masturbating a penis is often called ‘jerking off,’ and for a simple reason: perhaps the simplest way to masturbate is to circle your fingers around your cock and make some friction. For many trans women, this can be dysphoric, or bring up feelings of body discomfort or shame. If so, this technique may not be for you. But there is nothing wrong if this technique is what works. Remember, Your Body Means What You Say It Means.

A few things can help with this technique, however, both to lessen the dysphoria and to make it more pleasurable if you’re on hormones.

Lube. First and foremost, try some lube. Get some at Early to Bed, use hand lotion, whatever works for you. This can reduce the emotional/physical feeling of gripping a cock, which can be helpful, and is also great if hormones have increased your sensitivity.

Go Slow. For the same reasons that you may want to use lube, you may want to go slow.

Head to the Head. The head of the penis has analogous nerve and physical structures as the clit. There’s no reason you can’t take advantage of that anatomical parallel to get yourself off.

Hump Your Way To Happiness

Another simple masturbation technique is to point your penis up toward your belly button and layer some blankets over it. You can then rub the blankets to get friction and sensation down to your penis, without having to actually touch or feel it. That can be good for trans women who aren’t on speaking terms with their genitalia. This also has the bonus of making your crotch look and feel more like it has a vagina, which can be an emotional or mental turn-on.

This technique can also be ‘turned around,’ so that your penic is pointing down and toward your anus. You can secure your penis with tight undies, the blankets, or simply tuck it between your legs. Again, this can make your crotch look smoother while still allowing you to stimulate yourself.

Muffing

This is a term, popularized by Fucking Trans Women, for inserting a finger, small dildo, or small vibrator into one or both of your inguinal canals. Of course, since I can almost promise “inguinal canal” is not something covered in sex ed, the previous sentence may not be helpful without some explanation.

The inguinal canals are cavities or chambers (Fucking Trans Women calls them “pockets”) on either side of the groin, behind the scrotum and testicles. They’re where the testicles hung out (pun slightly intended) before they dropped. The inguinal canals are sealed by the skin of the groin and scrotum, but they can be reached and stimulated by inverting the skin of the scrotum and (gently!) pushing it up toward the pelvic cavity.

Check out Fucking Trans Women for some nifty diagrams, and have fun experimenting.

This can also be combined with the technique described at Alice’s Adventures in Trans*land, of using two fingers – one on either side of your penis – and approaching the inguinal canals from above. As Alice says,

One of my favorite things about this is that it looks like you’re legitimately fingering yourself, so it helps if masturbation causes you any dysphoria. This also feels absolutely AMAZING to have a partner preform on you. My boyfriend has done this to me numerous times now and I swear it feels better each time. It takes a little getting used to, but afterwards it feels wonderful, in my opinion.

Disclaimer: Muffing should not hurt if done correctly.

Kangarooing

Writing this guide has been tons of fun, if for no other reason than it gave me an excuse to talk about sex with my friends. (As if I needed an excuse…) One friend, while reading a draft of this section, mentioned a sex act I wasn’t familiar with. Here’s how they described it:

[I can be stimulated] at the base of my penis, just behind my scrotum and just ‘below’ my prostate. It’s basically in the exact spot where a vagina would be, which makes a lot of sense if you think about ‘sex differentiation’ and hormones and development and such (there are a lot of homologous structures).

In other words, this area is right below the scrotum, but not quite down to the perineum (also called the taint). You’re inverting the loose skin of the scrotum up into the open space of the pelvis, beneath/behind the balls and penis.  After some research, my friend discovered that this act is entering the deep perineal pouch, and stimulates the bulb of the penis.

Kangarooing is similar to muffing, in that you’re not quite penetrating an open body cavity, as you would be with vaginal or anal sex. But you are inverting loose skin to penetrate an interior body cavity – the inguinal canals with muffing, and the deep perineal pouch with kangarooing – thus stimulating the surrounding nerves in a new and (hopefully!) exciting way.

All the same disclaimers for muffing apply to kangarooing.

Telescoping (or the Shy Turtle)

This one works best for those whose penis doesn’t get totally hard or does so only reluctantly. If it gets hard or painful, stop. Do not “fight” against a hard penis.

 First push the flaccid penis inside its own skin. Think of this as inverting a balloon. If it starts to get hard or merely curious, the trans woman should relax and breathe until it stops. Keep pushing it inward and upward into the pubis using the middle finger and ring finger, while pulling the sides of the scrotum forward over the glans using the thumb and ring finger. The other hand may need to push everything into place. Keep tightening until the whole setup looks like a large clit, with the sides of the scrotum serving as labia.

 At this point the whole setup can be stroked or rubbed like a clit between the index and middle fingers. Gradually pull on the scrotum to enlarge the labia and to pull everything closer in to the body (or possibly some parts even into the inguinal canals). At this point, the whole setup can be penetrated slowly and carefully with a forefinger.

There are many possible variations on this, although it may take practice to keep everything from popping out.

What What (In the Butt)

Anal play can be done in conjunction with any of the above techniques, or on its own. Since there are lots of guides on anal play, I won’t go into too much detail. The fact that trans women have a prostate does mean that anal can be extra fun. (Take that, cis women!) Estrogen or testosterone blockers can cause the prostate to shrink, but there’s nothing too different about anal play for trans women than for anyone else. As such, the only notes I’ll give are:

  • Anal play can simply be putting pressure or vibration on the outside of the anus, with zero penetration.
  • If you do decide to experiment with penetration, go slow, especially the first few times.
  • Use lube. Lots. More than you think you need.
  • Allow the person being penetrated to control the speed for the first few times. Positions with them on top, or things like doggy style, make this easier
  • Did I mention using ALL the lube? Put down a towel and make a mess

Still looking for more info? Head on over to Early to Bed’s Anal Sex Dos and Don’ts page.

Toys

These are going to get a whole section of their own, so for now I’ll simply acknowledge that sex toys can be a lot of fun, both for solo and partner play. Don’t be scared to experiment, and see what works for you!

Doin’ It With Partners

As a trans woman, being sexual with a cis partner can be scary. The biggest thing you can do to lessen that fear is to get to know yourself: your body, your sexual response, your comfort zone, and your limits. Are there sex acts which will make you feel beautiful and wanted? Ones that will make you feel uncomfortable and unhappy? Also think about what language is going to make you feel good about yourself. Are there particular terms you definitely do want used for your anatomy? Definitely don’t want used?

Just like when any two cis people have sex (or three cis people, or seven, or eleven, or more!), there are no hard and fast rules as to what “should” or “shouldn’t” happen, as long as it’s all safe and consensual. Likewise, don’t let cultural messages get in the way of what you want to do with your body. There are no right or wrong ways to have sex as a trans woman, as long as you’re having fun. (And, again, it’s all safe and consensual.) In other words, do you want to use your cock during sexytime? Great! Very much don’t want to use it? That’s great, too.

Coming Out To Partners

You have no moral or ethical responsibility to out yourself to anyone. Ever. That said, there are some practical reasons to come out to a sexual partner before you actually get into bed with each other. The primary reason is safety. It sucks to have to think about transphobic assholes when we want to be thinking about fun sexytime, but such assholes exist. Outing yourself to someone when not in the heat of the moment removes some of the very real danger of a negative – and potentially violent – reaction.

If at all possible, it’s helpful to maintain a neutral and direct tone when coming out. People are social creatures, and we take our cues from each other. Hemming and hawing – “Well, I wasn’t sure I wanted to, um, tell you this…see, there’s this thing, uh, that you should, maybe, um, know about me?” – sends a signal that you’re not confident in what you’re saying. Whether or not you feel super confident, coming out often goes smoother if you can convey confidence (even if you need to fake it): “I’m trans. I wanted you to know, and expect that it won’t be an issue. Right?”

 Coming out confidently can also give you the upper hand; even if your potential partner reacts poorly, coming out with confidence can make them look like and feel like the jerk for not being OK with your trans identity, rather than making you look like you’re asking some huge favor by expecting them to not be a total jerkface stupidhead.

Thinking About Talking About Your Body

Remember those questions I had you ask yourself, way back in the section about finding a good headspace? I encourage you to revisit them and use them to think about how you can discuss your wants, your desires, and your body itself with your partner. This can be super scary and uncomfortable, but hopefully your partner wants to make you feel super-good. By considering what language you’d like them to use when talking about your body, and what sex acts you’d like them to try, you can help them help you.

And have fun!

Part Three: Sex Toys

We’ve talked about how to approach sex with a trans woman. We’ve talked about how to approach sex and masturbation as a trans woman. What else is left?

TOYS!

 Toys can be an awesome way to enhance solo or partnered sexytime fun for anyone. For trans women, they can also be an awesome way to empower us as women. And part of the impetus behind this guide was the lack of conversation about trans women using sex toys. Trans men sometimes have their own sections in sex toy shops, with strap-ons and packies and stand-to-pee devices and more. Cis women certainly have a wide selection of toys to pick from. Even cis men have a growing number of toys marketed toward them. But what about trans women? We can have just as much fun with sex toys as anyone else, even if you might not know that walking into your average sex toy shop.

 

Before You Get To Gettin’ Off

Sex toys are not scary. I promise. But it’s helpful to have a little bit of info before making a purchasing decision. Early to Bed has info on lube, and which works best with which type of toy.  Lube is great for any type of penetration, as well as for jerking off. Most shops (Early to Bed included) have smaller sample sizes, so you can experiment with a few different lubes before buying a 55 gallon drum of the stuff. (Sidenote: The reviews for that drum of lube are amazing!)

If you want to experiment with anal play – either on yourself or with a partner – you might want to get gloves, condoms, or dental dams. These are helpful if you simply worry that anal might be a bit icky, and especially important if you’re in a situation where you and a partner may swap fluids during sexytime.

Vibrating Your Way To Health And Happiness

When people talk about ‘sex toys,’ they usually mean one of two things: dildos, or vibrators. Lets talk about vibrators, first.

I honestly didn’t know if I’d like using a vibrator when I first tried it. I was raised in a world that thought I was a ‘normal’ boy. I had a relatively good and comprehensive sex education – my parents even bought me puberty books that acknowledged masturbation and said it was healthy – but I was still trapped in a world that things penises don’t deserve fun toys.

Not true!

The head of the penis has the same basic nerve endings as the head of the clit. As a result, stuff that feels good to a clit may feel good on the head of a penis. Namely, vibration. I know lots of trans women who – independent of each other – figured this out. We were all excited to share, and sort of annoyed we hadn’t learned sooner about this fun new way to pleasure ourselves.

If vibration is something that interests you, there are tons of vibrators to choose from. Explore Early to Bed’s website, stop into a sex toy shop and look around, and pick one that seems friendly to you. A few that might be good to consider as starter vibrators:

  • Magic Bullet – Simple, relatively cheap, waterproof
  • Michelle – Different form factor, still simple and cheap
  • Audrey – Small and inexpensive

If you’re interested in something a little more complicated (or expensive) check out:

  • Hitachi Magic Wand – Called a “massager,” but we all know better. Powerful!
  • Hand Solo – Masturbatory ‘glove’ with a vibrator. Yum!
  • Mimi – Fancy and expensive, oh la la!

So you have this new vibrator and you’re wondering, “What should I do with it?” The best answer is that you should experiment. Give yourself some alone time and see where all that vibration feels good. A few suggestions:

  • If the vibration is too intense – particularly on the tip of your penis – diffuse it with a few blankets between your skin and the vibrator.
  • Explore under your scrotum and down to the taint and asshole. What’s it like to masturbate while the underside of your cock is vibrating?
  • Nipple play with vibrators can be great foreplay.
  • Try different speeds, pulses, settings, etc.

It’s also worth trying a bullet-style vibrator and a longer vibrator with a handle, so that you can compare how they work for you. Based on the angles, I usually like using a vibrator with a handle, but you should use what works best for you.

 

This Would Be A Butt Pun If I Were More Clever

So you’re interested in anal play. Well, you don’t need any toys for that! Put on a glove (if that’s what feels safer or more comfortable), lube up your fingers, and go to town! Likewise, all of the above vibrators can be used around your asshole, but only on the outside. See Early to Bed’s guide to anal play for more in-depth information, but the short version is this: Use lube. NEVER put anything in your butt that doesn’t have a flanged base. A flanged base is when a toy has a spread section or handle to prevent it from getting lost up your butt. Here’s a toy with a flanged base, and one without.  If you use a toy without a flanged base, and it gets lost up your butt, you are almost certainly going to need a trip to the ER.

Still here? Good. I knew I could trust you. You would never use a toy for anal unless it had a flanged base, right? Right? Good. Here are some toys to consider:

  • Arrow Plug – Small, great for beginners, and can hold a mini vibrator for extra fun.
  • Booty Call Plug – Little bit bigger, but still not too scary
  • Azure – Designed to work as a vibrator. Yay!

Go slow, use lots of lube, and have fun!

Strapping In for Strap-Ons

Strap-on sex is a quintessential lesbian sex act. As a woman who mostly sleeps with women, it’s something I wanted to try. But I had a penis, which made me wonder: Can I use a strap-on comfortably? Sure, there are strap-ons made for cis men, but they’re marketed in such a way that made me feel uncomfortable using them. Could I use a “normal” strap-on comfortably and successfully?

YES!

After a very scientific process (i.e., me trying on a bunch of strap-on harnesses in the Early to Bed bathroom) I found that it’s possible to wear the Vibe harness comfortably. It’s not the prettiest or fanciest harness in the universe, but I could adjust it in such a way that the harness rested above my cock and balls, leaving them safe and un-crushed. Or so I hoped; trying something on in the bathroom is different than fucking someone with it. But – with the help of a very generous volunteer – I can now definitively say that it is possible to use the Vibe harness to fuck someone’s brains out, without crushing anything important. I wore it with undies on (to help keep my ‘strapless’ from getting in the way) and had tons of fun. It was very weird sporting a giant purple cock, and I highly recommend the experience to anyone – trans or cis – who is interested.

As someone who wasn’t really interested (either emotionally or physically) in penetrating someone with my ‘strapless’ cock, it was great to have the experience of penetrating a sex partner while using a strap-on.

Early to Bed also offers the Bend Over Beginner Kit, which comes with the Vibe harness and two different-sized dildos to try. Both of them are flanged, which means you can use them (with or without the harness) for anal play, too! Bonus!

Toys Designed for Cocks

In addition to the above toys, Early to Bed has a selection of toys made specifically for cocks. I haven’t tried any of them, so please let me know if you do! In particular, I’m sort of bummed I never got around to trying a fleshlight (or a vibrating fleshlight!) before my gender reassignment surgery. There are also vibrating cockrings to consider, masturbatory sleeves, and much much more. If you try any of ‘em out, please let me know what you think so I can update this guide.

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This guide was written by our friend Rebecca Kling.  You can, and should find her at rebeccakling.com and The Thang Blog.

Here is more about her:

Rebecca Kling is a transgender artist and educator who explores gender and identity through solo pieces and educational workshops. Her multidisciplinary performances incorporate conversational storytelling, personal narrative, humor, movement, video projection, and more. Kling takes the position that sharing accessible queer narrative with a wide audience is a form of activism, and that understanding combats bigotry. She regularly tours to colleges, universities, and theatre festivals across the country. Some touring highlights include theatres throughout Chicago, the 2010-2013 Chicago Fringe Festivals, the 2011 and 2012 Kansas City and Indianapolis Fringe Festivals, the 2012 and 2013 Minneapolis Fringe Festival, San Bernardino, New York City, Maine, South Carolina, and more. Her unique style and background as an educator have drawn her praise from The Chicago Tribune, TimeOut Chicago, NUVO Indianapolis, the Coyote Chronicle, and elsewhere.