Advice for someone new to crossdressing and D/s.

September 26, 2012 7:06 AM

My husband just told me he's into crossdressing and wants to introduce D/s into our sex life.

Basically, my husband of 6 years told me that he's really into crossdressing, and wants to do some kinkier stuff where I top him. I'm getting more okay with this; at the time he told me I was really upset because I felt like he was saying that the few years of our sex lives was inadequate. However, we talked about it, and he assured me that it was not, that he loved us, and that he loved having sex with me. Every now and then I have little twinges of panic and grief, particularly when he talks about wanting me to cum inside him using a dildo, but I’m gradually getting over that. I’m getting to a point where I understand that it’s more a kind of scene/play than him actually wanting me to be a man or have a dick. Heck, it’s not like we haven’t used strap ons before. He just wasn’t in a skirt those other times. So far, I’ve helped him pick a “goal corset” (if he does really well at his homework/upcoming tests, we’ll get him that) and have sent him some images of clothes and shoes. TBH I think the thing that bothers me is that in the porn links he’s sent me showing what he wants to do (like a crossdresser getting fucked in the ass), it looks painful and borderline non-consensual. When I see things like that, all the parts of my brain are like, NO ME GUSTA! Besides this, we've actually had some fun exploring this new aspect of our relationship; we've also been checking in with one another pretty frequently, and have had a lot of really good, really deep conversations about this permutation in our evolving sex lives.

Anyways, as we’ve talked further about this, it’s becoming clearer to me that he’s really into being submissive as well. This makes sense; he’s mentioned before that he likes it when I’m more aggressive in bed, and that he likes it when I’m rougher with him. The thing is, my ONLY experience with BDSM (as a hot, curvy, embarrassingly naïve undergrad) was as a lifestyle sub for my first boyfriend. It left me with a real bad taste in my mouth for kinkdom in general and BDSM in particular; I feel like he used his kink to be cruel and controlling, and that any scenes we did involving toys and props were really about him bolstering up his fragile ego using violence and verbal abuse. I have a real antipathy towards doing that with my husband, even though I can tell that this is really important to him. It’s also been really upsetting me that I really liked the few times we’ve played a little bit rougher (like with me spanking him, orgasm denial, etc) because I would never, ever, ever want him to feel like I did when I was with that first asshole. This is probably one of the major reasons he waited so long to tell me.

The other thing is, we’re long distance for the next four months. He is training for his job, and has a roommate. Sometimes the roommate goes out on the weekend, and then my husband has a little privacy. There is no possibility of my seeing him in person until December, so everything we’re doing now has to be by phone, Skype, or chat, and has to be something easy to hide/put away if his roommate comes in.

Now, here’re my actual questions:
1. What resources would you recommend for someone sticking a toe into the world of D/s, particularly for a woman exploring being a top?
2. What are some activities I can assign my husband to do long distance? I’ve looked at this thread for ideas, but would like more inspiration.
3. What should I know about being married to a crossdresser?

posted by anonymous to human relations (15 answers total)

Top female with crossdressing partner here.

Fetlife is a great resource and social space for all things kinky - and there's even a Metafilter group. Come and say hello!

Some books you might want to check out: The Good Girl's Guide to Female Dominance, The Art Of Sensual Female Dominance and The Sexually Dominant Woman: A Workbook for Nervous Beginners are all good 'starter' guides for women just getting into playing a dominant role with their partners and offer lots of useful suggestions for when you're starting out on a D/s path (or when you're simply at a loss for what to do first - or next).

Feel free to mail me here if you have any specific questions, or come find me on Fetlife (Teamouse).
posted by Acarpous at 7:23 AM on September 26, 2012 [7 favorites]

This seems like an awfully tough time to introduce several newer and potentially big things at once. I think you could have a lot of fun with the whole Skype/phone/video thing, but I also think that a lot of this should probably be negotiated when you're in person and can share things more intimately -- in the comfort of the home you share together, being able to touch and whisper and do some of those things you've talked about to the exact level you've planned.

This is not to say "hold on there; nothing until later!" but it's probably worth going very slowly.

Of course, by "slowly" you could also mean "I'm stretching out the delicious agony of anticipation. So there's that :)
posted by Madamina at 7:29 AM on September 26, 2012 [1 favorite]

You may want to start off with When Someone You Love is Kinky.
At Her Feet is a pretty good look at what a 24/7 D/S dynamic is like, though it's written in a sometimes irritatingly cutesy voice.
I've also enjoyed Claudia Varrin's books, especially The Art of Sensual Female Dominance and Female Dominance: Rituals and Practices.

It think it will be important to you to learn more about your partner's interest in cross-dressing. Is it because it makes him feel more submissive? Is there an exciting element of humiliation or display in it for him? Or does he just find female clothing more sensual than male dress? Try not to let too many rigid gender ideals distract you right now. Just explore where this is coming from.

It also sounds like you had some pretty bad experiences with BDSM before. It doesn't have to be verbal abuse and ego-crushing, unless that's what you both find mutually satisfying. Check out Clarisse Thorn's blog for some pretty illuminating discussions of the difference between D/S play and abuse.
Feel free to memail me.
posted by Kitty Stardust at 7:30 AM on September 26, 2012

I agree with the going slow in a good way advice. And don't be shy about telling him both what you like (eg the spanking) and what isn't working for you (eg the porn). I mean, if he wants you more in charge, a great beginning point is telling him to find you some hot (by your standards) porn or erotica.
posted by Forktine at 7:36 AM on September 26, 2012 [2 favorites]

Something I found helpful when first getting into less errr mainstream bedroom antics was to start out by simply laying together in bed and running ideas together in the form of almost stories together. This would work long distance on the phone really easily. Sort of a way to mentally try on ideas first, a shared fantasy if you will. We'd describe scenes, clothing, who is doing what it was a good way to find out just what each of us wanted from a scene and what we didn't before we were in the actual situation. It was also pretty hot and fun when we found something that set us both off. Being separate for this part might actually work better, as you might feel less self conscious if he's not in the room.

Dominance doesn't have to be all soul crushing, and I'm sorry that your first experiences where so bad. You can think of it as I am going to take care of you in the extreme, say maybe like having a fun sex pet. You control it, discipline it when it's bad, reward it when it's good and still love it and dress it up in pretty things, or you know what ever floats both of your boats.

Remember an important thing too, and I know this might sound weird, just because you are the one playing the Dominant role it doesn't mean you have to do stuff you don't enjoy. I would get so in the whole concentrating on making a scene work that I'd forget I was supposed to be having fun too and started to feel resentful. Once I realized it had to be fun for both of us it made a huge difference.

The books I was going to suggest have all been recommended already and are really worth reading.
posted by wwax at 8:06 AM on September 26, 2012 [3 favorites]

First off, I just want to say that you sound like a wonderfully open, thoughtful and giving partner. Your husband is really lucky to have you. Second, it sounds like you're both doing everything right - talking openly both about your desires and your concerns. Definitely make sure you keep doing that no matter what.

I'm female but have some similar kinks to your husband, so hopefully this will offer some helpful perspective.

I feel like he used his kink to be cruel and controlling, and that any scenes we did involving toys and props were really about him bolstering up his fragile ego using violence and verbal abuse ....

It’s also been really upsetting me that I really liked the few times we’ve played a little bit rougher (like with me spanking him, orgasm denial, etc) because I would never, ever, ever want him to feel like I did when I was with that first asshole.

Ugh, I'm sorry you had such a shitty experience. Unfortunately, this does happen in the BDSM world. BUT I think an important thing to remember is that what happened between you and your ex was wrong because of the way it made you feel and his intent, not because of the actions themselves. It's different with your husband, because he really wants this. You may get pleasure from it (which is great - pleasure is good!) but so is he. That's a really crucial difference.

That's not to say YOUR doubts and hesitations aren't important. Obviously you shouldn't have to feel like you need to do something you're not comfortable with. I think it's important to make sure that you guys keep talking and checking in to make sure you're both feeling OK and that you're both getting to talk about anything that's making you feel icky. Also, are you familiar with the idea of aftercare in BDSM play? It's for the top as much as the bottom, so make sure you're getting aftercare that helps you and your partner connect after play.

I agree with the above commenters that this time while you're apart is not the best time to push either of your boundaries, especially because you can't get that physical reconnection after play. But it is a really great time for you guys to talk about this stuff - and that can be fun and sexy. For instance, you could have him describe some of his fantasies to you - in great detail - along with what exactly about those fantasies is so hot to him. Understanding just how hot he finds this stuff and why might help you feel more ok with it.
posted by the essence of class and fanciness at 8:41 AM on September 26, 2012 [3 favorites]

It left me with a real bad taste in my mouth for kinkdom in general and BDSM in particular; I feel like he used his kink to be cruel and controlling

My Prime Directive of BDSM is that bullies should not be dom(me)s, and dom(me)s should not be bullies.

You soooo don't sound like a bully. You sound like the opposite of a bully. Dommeing may or may not be for you, but I want to reassure you that it doesn't make people who aren't already bullies into bullies.

Acarpous has already pointed you to lots of good resources; I would add The Mistress Manual by Mistress Lorelei.

Rachel Kramer Bussell has edited a couple of anthologies of femdom stories that might give you some food for thought as well.

And please, feel good about going at your own pace, even if it feels a little slower than what your sweetheart would like.
posted by Sidhedevil at 9:47 AM on September 26, 2012 [1 favorite]

Welcome to the dark side; the cookies are rather lovely on this side of things!

I'd like to first address your ex boyfriend: your ex wasn't a Dominant, he was a jerk who masqueraded as such. You know that of course, but I just want to reiterate that submission is something given, not seized. Your ex would've probably been thrown out of places like the Crucible (D.C.), because it is very clear that you were uncomfortable with it. I'm so so sorry that happened to you.

Aside from the fact that you sound absolutely thoughtful and open-minded, the key difference between your ex's behavior and your Dominance is that you are approaching this with consideration, acknowledgement of boundaries, and open communication with your husband. And you guys are finding your place in D/s as a team! Some people are into degradation and humiliation, sure; but those acts are conducted in-scene with mutual respect for both parties, and never out of malice. That's D/s, and don't let anyone tell you otherwise!

I am Domme, and can help a little with your second question. When I first realized my alignment, I was absolutely terrified about how to handle all of it at once. I started with small things like "inspections." If his roommate isn't there and you both have a free moment, conduct one: have him strip naked, on camera, and turn 'round (while you remain fully clothed), check his hair, etc. There are plenty of things you could then do, including orgasm denial and control. As you get more comfortable with it, perhaps you two can explore chastity belts. You can also add certain telephone protocols that reassert your dominance from afar, if you'd like.

Continue to keep your eyes and mind open; others have made great suggestions so far. You'll be a great Domina, anonymous! Feel free to MeMail me.
posted by Ashen at 11:00 AM on September 26, 2012 [1 favorite]

Also, my FetLife username is AshaTheConqueror. If you decide to join up, feel free to find me there as well!
posted by Ashen at 11:04 AM on September 26, 2012

Agreeing with everything Ashen wrote.

I do not agree that your husband's expressed interests are indicative of cryptohomosexuality. This is where it will become vital for you to explore what he finds appealing about crossdressing. Quite a lot of submissive men enjoy forced feminization. There is a very good book called My Husband Betty about women who've been in relationships with crossdressing men.

As for what you can do at a distance if you're interested in playing with this: send him some lacy, frilly lingerie of your choosing and command him to wear it under his work clothes. Make him take a picture for you sometime during the day to prove he's obeying. Have him sleep in a nightie or a pair of silk stockings (also with pictures ensuring compliance). Order him to go shopping at Victoria's Secret to buy a "gift" for you. Of course, he'll be wearing it later. Make him earn the right to masturbate by performing certain tasks. If he's handy with writing, have him write you some fantasy scenarios that he can then read you over the phone or Skype.
posted by Kitty Stardust at 11:05 AM on September 26, 2012 [1 favorite]

Oh, and make sure you are enjoying what you're doing. Topping is hella hard work, and if it does nothing for you it's easy to become resentful.
posted by Kitty Stardust at 11:07 AM on September 26, 2012 [2 favorites]

My partner and I recently took some time to make lists to share with each other. We each made a list of "things I know I like to do"; "things I think I'd like to try"; and "things I fantasize or might want to talk dirty about but probably wouldn't actually be into." Then we sat down and went over our lists. It was fun, and it gave us some ideas.

We have since tried a few new things in a spirit of exploration. For instance, I absolutely never used to be into oral sex at all, giving or receiving. But that was something he put on his "I'd like to do" list, so one night when we weren't doing anything else, I just went down on him a little, to see what it was like. It turns out that I've changed--I really like giving oral sex to him. But I haven't changed all that much--although we've experimented on several occasions, receiving it still doesn't do much for me. The point is, we don't always say, "Let's have sex!" but we might just spend a little time messing around with a specific thing to see if it leads anywhere, or if we like it.

We talked really explicity about the possiblity that there would be emotional bumps along the way as we experimented, and made a commitment to take care of each other if we hit one of those bumps. That is, if we tried a thing and one of us was like, "Oh, hey, no, I need to stop this" and the other one was so into it that stopping felt bad, or they felt rejected or insecure, that we'd take a little time to say, "You know, I really love how into sex you are, and your adventurous spirit, and even though that thing we tried didn't work out for me, I'm still really excited about having sex with you," and then, on the the other hand, "I really appreciate you trying that out and it's totally OK that it wasn't your thing. There's lots of good stuff we both really like to do." This has made a big difference to us--we'll even say to each other, "I need my bit of reassurance now."
posted by not that girl at 12:03 PM on September 26, 2012 [4 favorites]

Well, this sounds like a slice of my life. I am a switch (enjoy both Dom and sub roles) who really enjoys assplay.

First off, good on you for not being immediately judgmental and harsh on the husband. It can be amazingly difficult coming out about these things as many partners (including one of mine in the past) have some distressingly deep issues confronting such desires in their partners. And doublegood on you for being so willing to discuss such desires openly and with intent to consider.

A lot of people get hung up on D/s desires, and other things like you mention here, as they are "not normal" and "wrong". I used to deal with a sub who had convinced herself "Good girls do NOT enjoy this" whilst she still craved, as I put it, time in harness.

All I can say, as this strikes so close to home, is please, please, feel free to contact me, or even have you husband contact me, either via MeMail or the email in my account. I swear to keep everything on the up and up and completely confidential.

And a D/s relationship does not mean cruelty. It just means control and the relinquishment thereof. Some people just really dig the apparent abandonment of responsibility. Some people like their butts played with. Ain't a thing wrong with either, in my book.
posted by Samizdata at 5:20 PM on September 26, 2012

Seconding Kitty Stardust that topping can take a lot out of you, and it needs to be put back in one way or another.

It's so neat that you're kinda curious, not upset, about a big switch in personal expression and I hope you and he can keep that characteristic going. It can be very difficult to accept a step change like that. That goes double for the non-consensual appearance of some porn - which is not meant to be accurate, it's often more like a stepping-off point for providing ideas. If I had lived out every fantasy I ever had - or even half of them - I would be in a wheelchair, or dead. They're cute stories and that's all, until they aren't and that point varies person by person.
posted by jet_silver at 5:44 PM on September 26, 2012 [1 favorite]

What should I know about being married to a crossdresser?

I think the main thing you should know is that crossdressing means really different things to different people.

Some guys are into it because they find it humiliating and they find humiliation hot. Some guys are into it because they're genuinely more comfortable in women's clothing and find it empowering rather than humiliating. Some guys it's not particularly a gender thing at all, the appeal is largely that of breaking a taboo. Some guys it's all about playing with gender. For some guys the biggest dream is being able to pass for female in public. For some guys passing would be irrelevant, or would even interfere with the fun of playing around in between categories.

So now that he's come out to you, it's not the end of the process, it's the beginning. You're both gonna do a bunch of learning about what this means to him, and what parts of it are most important in his book, and how you can fit it in with your interests and needs and desires. (DON'T FORGET ABOUT THOSE!)

Which means also be prepared for his wish list (and yours) to evolve. Right now he's excited about you cumming in his ass. And that might be an aspect of this sort of gender play that's always going to be exciting to him — or it might be that in a year he'll be like "No, you know, actually I don't need the magical high-tech squirting dildo, X and Y and Z are more important instead." Or it might be that in a year you'll think the idea of the magical high-tech squirting dildo is just the hottest thing you've ever thought about and you'll have no idea why it used to make you so squeamish. Or... well, you get the idea.*

Go slow. Keep checking in with each other. Don't get so fixated on one goal or plan or fantasy that you forget to ask whether it's still what you both want. Remember that for most itches, there's more than one way to scratch them.

*A propos of that lovely (if you're into that sort of thing) getting-cummed-on feeling: in my book, having warm candle wax splashed on my back is the next best thing. The idea of wax play never particularly turned me on, but the first time I actually did it and realized what else it felt like, I was sold. Something to try, if he keeps fantasizing about toys that go squirt and you keep feeling squicked out by the idea.
posted by nebulawindphone at 7:03 PM on September 26, 2012 [3 favorites]