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

SabrinaRoxanne 36T
0 posts
7/15/2016 6:33 am
So You’re Going To Have Sex With A Trans Woman

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:

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!
Sabrina.


need4freedom 62M  
102 posts
11/22/2016 6:51 am

thank you sexy


HAVEFUN150 60M  
1226 posts
2/27/2017 3:53 pm

Very good post. Thanks.


Januaryman99 55M  
327 posts
10/11/2017 6:55 am

A real good read! Thanks for posting, Sabrina.

. . . "inguinal canal." Funny, the stuff they don't teach you in 7th grade health class.

Stop by my BLOG => Januaryman99


Frnd4Lfe 62M  
1 post
12/8/2017 7:18 am

Thanks for this blog Sabrina. Lots of "general" information. But what I'm most interested in is knowing what specifically pleases YOU ..... and when can we be together would be another important question. ;- )


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