Courting Disaster is a new advice column on matters of the heart (and loins) coming to you directly from the revolving door boudoir of international queen of hearts, Morgan M Page. A long-time notorious dater from sea to shining sea, Morgan is a trans girl on a mission to solve all problems big and small in your feminist, queer, and trans situationships. Not just any old Carrie Bradshaw, Morgan is the creator of Brazen: The Trans Women’s Safer Sex Guide, and will put her near-decade of experience as a sex educator at your disposal.
Dear Courting Disaster,
How do I make strap-ons sexy?
I’m a trans man. One of those mostly stealth ones. I’m five foot four and somehow straight women show interest in me. I guess the square jaw and not totally horrible style does it.
Once they’ve had to get past the fact they’re attracted to a short man, then I have to drop the trans bomb. It’s truly a test to see how far heterosexual women can bend their sexualité past masculine must-haves, aka height and a cock. I’ve gotten only good responses so far.
My sexual history looks like me eating pussy for 5 dates in a row with my boxer briefs on and then sheepishly messaging them via text or Facebook asking… so strap-on? I’m scared the “toy” aspect makes it feel incredibly kinky for them. I’m also insecure about being compared to cis dick, though I do buy vixskin almost exclusively. As a side note, if you have any recommendations for a great feeling cock let me know.
I’m confident in my ability to get a woman off but when it comes to dicking a woman down, my favourite thing, I feel so shy. I’m getting older now and I’m sick of weirdly rushing to the washroom to put on my harness and stick all eight inches of cock out of a pair of underwear while she lays in bed waiting. The action is paused and it feels like a turn off. But what’s a hot way to strap it on? Does that even exist? How can I be more confident? I don’t really like putting it on in the nude because I’m scared of freaking women the fuck out. That comes like 20+ dates later and I’m sick of it. I’m in my mid-twenties and I like to fuck. I want to fuck with the confidence of a cis man who can just pick girls up at the bar. Help me out here!
Stumbling Over Strap-ons
I want you to know that I have personally suffered in the writing of this month’s column. In order to provide the most professional and scientific advice for your problème de coq, I listened to not one, not two, but twenty different songs about penises. Ranging from Ginuwine’s classic str8 man dick-riding anthem Pony, to Peaches’ raunchy celebration of genitalia in Shake Yer Dix, to Jonny McGovern’s paean to the hypnotic allure of swinging dicks in Dickmatized. Most of these songs are not what one would call classics, and that’s putting it lightly. But given the weight of the problem you’ve presented to me, I felt it was only right to consider every inch of the situation.
One song, in particular, speaks directly to the occasional inconvenience of attachable penises. American avant garde band King Missile struck an unexpected hit with their 1992 single Detachable Penis, which rocketed up to number 25 on the Billboard charts when it was released. The lyrics and video tell the story of one man’s desperate search for his detachable penis. While he reflects that “This comes in handy a lot of the time/I can leave it home, when I think it’s gonna get me in trouble,” he also has an unfortunate habit of leaving it random places whenever he gets drunk. Though forgotten by many, the song is, unsurprisingly, still popular among trans men.
Just like in the King Missile song, having a detachable penis has many benefits. They are, in fact, this writer’s favourite kind of penis. You can choose the length, girth, shape, and even colour of an attachable cock. If, like me, your partner is a real Goldicocks who only likes them to be just right, this comes in handy. They also don’t suffer from the banal problems of other types of cock—erectile dysfunction and premature ejaculation are no danger, and if exposed to an STI you can simply boil a silicone cock to disinfect it.
But having an attachable comes with its own particularities. Namely, the issue of getting the damn thing on. Oh! How many nights I have spent 3-10 minutes laying partially undressed on some masc’s bed, scrolling through Facebook on my phone while I waited for him to strap it on!
I have found, in my extensive fieldwork, that there are many variations to this temporally short but emotionally lengthy pause in the middle of sexing the trans man. Most guys prefer to duck into the bathroom, taking care of this sometimes-ungainly routine in private before returning to fuck my brains out. Others have asked me to turn away for a moment while they do it at the edge of the bed. But my favourites make getting their dick on part of the fun.
One recent lover, whose whole thing was being dominant, barked at me to get face down, ass up, and shut my eyes until he told me I could open them again. This move made my little bottom heart flutter! Recounting it to (many) friends later, I dramatically put my hand to my heart and breathily stage-whispered, “Daddy.”
Now while that particular move may be most effective with someone who enjoys a little consensual domination in the bedroom, it’s main idea—that putting it on can be part of the sex rather than a break in the sex—is broadly applicable. Let this be my first piece of advice for you: getting your dick on doesn’t have to be awkward, it can be hot—all it takes is some confidence.
As for recommendations, I’m going to let you in on a big secret: honestly I have never in my life been able to tell a difference, sensation-wise, between cis dicks and anatomically-shaped attachable cocks. Maybe my pussy’s palate is just not refined enough to separate the wheat from the other kind of wheat, but either way it’s all gluten to me. Cyberskin definitely feels better in my hand, but it has the unfortunate problem of not being boilable for sterilization, so I generally recommend silicone.
Let’s get at the real meat of your question, though. Will str8 girls find it kinky to introduce your dick into the bedroom? I certainly can’t speak for all str8 girls (am I a str8 girl? A mystery for the ages), but I think by the time you’ve dropped that “trans bomb” on a str8 cis girl, you have already blown past her “this is kinky” road sign. This is not to say that trans people should be treated as a kinky fetish, but the reality is that that’s how most cis people think of us.
But I think the problem you’ve having here is an issue of framing. An attachable cock is not really a sex toy, it is a dick. It’s your dick (you bought it, it’s yours!). Now, the thing about str8 women is they’re already expecting the men they want to have sex with to have dicks. So introducing your dick into the bedroom really isn’t going to shock a girl who has already accepted and moved past the “trans bomb.”
And let’s be honest: even if she did find it kinky, lots of str8 girls love kink!
That said, if you want to ease any possible fears of kinky sex toys, use a RodeoH harness instead of a leather strap. Instead of a complicated series of leather or plastic straps, which definitely look like they’d be at home on a minor character in a Tom of Finland drawing, the RodeoH is a harness hidden in a pair of briefs or boxer briefs. As I’m sure you know, they come in a variety of colours, and the best part is that they double as underwear, so you can wear them all night and when things are getting hot and heavy you can just slip your cock into them and get right on to dicking that girl down the way she wants!
Speaking of which, I have not covered pack-and-play cocks. There’s a reason for this. Pack-and-play cocks are kind of the worst. A pack-and-play is a type of cock that can worn “soft” when you’re out and about and then be erect when you need it. Some include the option of being an STP (Stand-to-Pee) device. Prone to breaking, embarrassingly large to wear as actual packers, and troubled by the accumulation of lint throughout the day, pack-and-plays are a great idea that just doesn’t quite work in practice. And STPs, unfortunately, end up pretty gross if not washed out thoroughly after each use.
I find it both curious and erotically compelling that you give some humble bragging about not only hooking up with str8 girls but also about your apparent skills at eating pussy. Based on your message, it seems that if you’ve “gotten only good responses so far,” maybe it’s just you who has hang ups around height and dick size.
Now I am a tall girl. A minor giantess, if you will. And let me tell you, never have I ever had a problem with a guy shorter than me being the brutal dom top I need. The secret ingredient that turns any person—no matter their height, genital configuration, or anything else—into a true top is just confidence. Act like you have “the confidence of a cis man,” and any lucky, consenting bottom will be enthralled.
It might be time for you to have a talk with yourself about your insecurities because it seems like they are the only things holding you back from giving that good D to a girl who wants it!
Returning to King Missile’s 1992 hit, the narrator leads us through the struggle and inconvenience of trying to track down the penis he lost when he was drunk. He eventually finds it being sold on a blanket on Second Avenue and buys it back. What a hassle. Despite this, he still sings at the end of the song that “People sometimes tell me I should get it permanently attached/but I don’t know/even though sometimes it’s a pain in the ass/I still like having a detachable penis.”
Send your feminist, queer, and/or trans dating problems to Courting Disaster at email@example.com.