Hey there! So, I’ve got a little bit of a dilemma on my hands that I could really use some advice on. My boyfriend has this thing for crossdressing during sex, and while I’m totally open-minded and liberal when it comes to gender expression, this kink of his is throwing me for a loop.
Let me paint you a picture: we’ve been together for about six months, and he’s the sweetest guy ever. Seriously, he’s like a dream come true. But here’s the thing – he’s really into this whole crossdressing scene when things get intimate. He’s not transgender or anything, he just likes to explore his feminine side during sexy times.
Now, don’t get me wrong, I’ve got no issues with gender non-conformity. In fact, I’ve dated all sorts of people across the gender spectrum. But for some reason, his crossdressing kink just isn’t hitting the mark for me. It’s starting to feel more like a caricature of femininity rather than genuine expression.
Here’s where things get tricky – I’ve tried talking to him about it, but I’m not sure how to bring it up without hurting his feelings. I want to find a way to address this issue delicately and respectfully because, well, I care about him a lot.
So, dear internet friends, any thoughts on how I can navigate this situation without causing any harm? Hit me up with your advice and insights, I’d really appreciate it! 🙏🏼 #HelpAGirlOut
And hey, if you’ve got any experiences or stories to share, feel free to drop them in the comments below. Let’s get this conversation rolling! 💬
I don’t think you can address it to him without coming off “bad” in his mind. If you have a problem with it or don’t like it you just have to be open with him on it :/ like, if it’s something that you don’t see yourself enjoying the rest of your life you need to respect yourself and bring that forward as much as possible.
Typically cross dressing leads down more paths. I knew a relationship that this happened with (almost same story) and it didn’t end well.
If its not your cup of tea, its fine – you guys just might not be compatible. I know this isn’t the advice you’re looking for, but 6 months is a good amount of time to know whether or not you are “it” for someone, and it seems like he is not “it” for you. Personally, I would love to be with a guy who is into sissyification/femdom. Like seriously love love. But again, if its not your cup of tea, you may not be able to get over it..
Now, if you want to try and get into it, you would have to try and understand the mindset he enters when you guys do this sort of play, ask him what he likes about it, or what his favorite parts of it. Some guys just simply like being able to just be soft and feminine for a moment of vulnerability, or because it makes them feel embarassed and it turns them on to be humiliated by someone they feel safe with. Ask yourself what kind of pleasure can you extract from this experience? Does the idea of you “taking care” of him in all his vulnerability get you turned on at all?? If you can’t try and get into his head and work out a way for you to get into it too, then your relationship may be doomed. There’s no way you guys can have a vanilla only sex life (because well, he knows what he likes and he deserves to have it).
Edit: bdsm/femdom community support subs on here may be helpful for you too.
No matter how you address it, you most likely will hurt him in some way. If it’s not what you like – it’s okay, we all have our own preferences about intimacy. But when it comes to intimacy and if there’s something and you’re feeling off about, you need to talk with your partner. If it turns out you’re incompatible, you might want to go separate ways. If you want to try to get into it, it should be slow and gentle without any pressure. Ultimately, if both of you won’t be able to get past this, you’ll be better off going separate ways
It looks like a moral judgement from your part which I think you shouldn’t make. If you don’t like the way he lives his sexuality, tell him and if you can work it out, fine, if not leave.
Why bring it here if he’s repressed, gay, straight, or whatever. You are the one uncomfortable, like, he’s not hurting anyone acting like you say he acts. Seems like incompatibility in that regard, just that
Edit: typo
You have to be harder on him here, op. He doesn’t seem to care about what YOU want in sex.
It sounds like the issue is more the lack of sex you enjoy, rather than too much “sissy” sex. Have you talked to him about the low frequency of sex? Are both of your sexdrives just low, or is it that he doesn’t really want sex unless it’s sissy stuff? I think those are the questions you need answered, because that will be important to find out where the middle ground could be.
> He doesn’t watch too much porn or anything, he isn’t addicted, so I know this isn’t entirely some kind of internet brainrot.
Surejan.gif
Yuck
It’s hard to be a feminist and also be ok with the sissy stuff, because you’re right, it’s inherently misogynistic. You’re probably not compatible with this person. And as someone who has known a lot of crossdressers and dated some, it’s never just crossdressing, they just haven’t figured that out yet or are too full of shame to explore it properly.
Just tell him the truth. If you don’t like it, don’t do it.
He is asking too much of you. Tell him you were willing to try it, and you did, but you don’t ever want to do it again and that you feel like he is not liking you for you romantically. What he wants is not something that you want.
Domt worry about hurting him. Worry about yourself.
You sound like someone very open minded and the reason I start with this is because in my opinion I think this is key to working things out. My concern, reading between the lines of your post, is that because you are so wonderfully open minded (and don’t ever change that) you are giving time to a relationship that may not fundamentally work. Intimacy is important in most relationships and it’s sounds like it’s important to you and your partner, however the intimacy that you have together is not compatible at the moment. Kinks are varied and diverse and I’m sure there is someone who will have the right link to match his but maybe it’s not you. Alternatively, and taking into account the fact you said this isn’t a “dump him” post, I think you have to explain to him how his portrayal of females in his fantasy/kink feels rooted in misogyny and therefore doesn’t feel like a turn on for you for that reason. It’s not about him it’s about behaviours that can actually be adapted and can satisfy you both. But without a gentle and supportive dialogue “dump him”.
My partner is like this but is pansexual. Regardless of what he’s into you need to decide what you’re into. If it’s not this that’s totally okay. I would be open and honest about how you feel and what your needs are. It may be a deal breaker though unfortunately so prepare yourself for that. Best of luck either way.
I’m gonna go ahead and kink shame. This is weird as fuck. It reminds me way too much of the DDLG scene only he’s the LG in this scenario. Anyone who sexualizes child like behavior needs to be locked up. Full stop.
I think married couples should do this but just for safety. I can see my wife’s but I never look at it. I feel better knowing that if I was worried about where she was or why she wasn’t home (and I mean with a valid reason — not why are you 5 min late from work lol) I could see where she is.
Simple, you don’t.
You respectfully tell him that you can appreciate that he has things he likes that do no align with what you like.
Because of that, and because you wouldn’t want him to stop being himself, and because you do not want to stop being yourself, that it’s not going to work out.
Anything else is gonna flirt with kink shaming and is going to hurt because either you’re gonna go your entire life not having fulfilling sex, or you’re gonna force him to do the same thing for you. That builds resentment.
The writing is on the wall.
Sexual compatibility can make or break a relationship and in this case one of you will be unfulfilled.
Y’all aren’t compatible. There. Simple as that.
Also, the part where you said his fetish is being a misogynistic caricature of women – not of real women – that is spot on. This IS brain rot from watching misogynistic porn (most porn is misogynistic). Nobody learns this behavior from the natural unfolding of their sexuality. It’s industry propaganda infiltrating his view of sexuality.
I would also like to echo what another commenter had said. He is very selfish and doesn’t ask you how he can please YOU. It seems like he expects you to make yourself malleable and accommodate his extravagant preferences for every sexual encounter.
Ok there is a slight difference between a kink and a fetish. A kink is something that turns you on, where a fetish is something you NEED to be turned on. It sounds like he’s not into sex where sissy stuff isn’t involved. If that’s not something you’re into, it will be a pretty major incompatibility.
Can you see yourself wanting to deal with this six months, a year or more from now?
Do you see yourself marrying this person and bringing children into this?
Do you enjoy how icky this is making you feel?
Does he care how icky this is making you feel?
If you answered no to most or all of these questions, you have your answer and need to advocate for yourself and leave.
If you answered yes, to most or all of the questions, then you need to mentally prepare yourself on how your relationship will be centered around his sexual kinks that will most likely evolve into something else and most likely act out this behavior with other people with or without you.
At least you know before getting pregnant, because I have seen this come out of the closet once a pregnancy comes into the mix in more than a dozen marriages I have worked on while doing divorce mediation for family court.
This isn’t a kink, it’s a fetish. He cannot get off without it. He does not want to have vanilla sex with you. You do not share his fetish.
Some sissy boys are incredibly selfish. They just don’t care about the sexual satisfaction of the people they’re with. The people they have sex with need to take satisfaction from them by force, which they can be incredibly into, or accept that they will have none.
Is that you?
Are you mommy?
Are you ok with being mommy forever, more and more?
You’ve laid your needs out plainly and he doesn’t care about your sexual needs.
Is that the relationship you want?
Breaking up with someone isn’t a punishment. You two are sexually incompatible. That won’t change. He doesn’t want to change. You can’t make him change. You didn’t know this could happen to you because your bi or pan, but you can still be sexually incompatible.
I know you said no breakups, but you’re never going to be acknowledged sexually in this relationship. You are not into this kind of sex. You are forcing sex you don’t want onto yourself to keep a partner. That’s tragic, and he’s not going to stop you.
Christ I remember when sex was a simple pleasure.
The one thing I’ll say is that you should share what you’re up for and not up for without sharing all your reasoning for why it gives you the ick – The latter is likely to come off as criticizing him or making it wrong whereas the former is just a fact about you
We can talk if you want but its more private than id like to get into on public
Girl. I get that you like him. I get that you don’t want to break up. But you need to realize that you two are not even remotely sexually compatible. And you can’t get around that in a sexual relationship.
Try putting your foot down. See what happens next. No more kinky sex. He can’t dress up. He can’t make girly noises. He won’t have vanilla sex with you. He doesn’t want it. He only wants sex his way. And right now, you are having sex that you are not into, just to appease him. This is not healthy in the long run.
I get you think he’s great. But he’s not even willing to compromise for you. He’s not even willing to give you the kind of sex life that you want too.
This is not about not hurting his feelings. This is about understanding that when we date, we are looking for a good match in all areas. And he is not it.
You are not compatible
OP: To be clear, I am looking for advice that isn’t just “dump him.”
Comments: you are incompatible, dump him
You’re not sexually compatible that’s it. Don’t drag this out, end it and maybe you both can find someone sexually compatible
I know a couple like this. (I was their bull for a little bit)
He ended up breaking things off with her and got with a man.
lmao
“You love the way you feel when you wear your satin panties, so why don’t you wear them to work? There’s that silly boy, who would ever find out?” He may learn to be dissociate clothing with fantasy.
Hurt him. You might discover he has a pain kink too.
That’s how the whole “trans” thing starts. The get tuned on by feeling they’re being desired the way misogynist straight man desire women. Dump him
You’re not a kink dispenser. You will find his fetish will be the only way he can perform and that’s that. If it was an occasional thing, great. But it’s not.
You are not compatible end of story. Stop stringing him along and let him find his forever person.
Ask him if he watches “sissy porn.”
The part that I think is the biggest red flag is when you said “he does stuff for me like sitting in stores and watching bridgerton” as if that is comparable to bedroom stuff. Partners should be doing things, sometimes including things they don’t necessarily love, to make their partners happy in a romantic/person to person way as well as sexually. It sounds like all your intimacy is focused on him and his kinks/interests but never on the things you like. Does he actually take the time to make you feel good too? Does he say/do things that you want him to purely because it’s something you’re in to or does he only pleasure you if it in some way pleasures him too? Maybe the first step is to have that conversation of, “It sometimes feels like my needs don’t matter when you do xyz” and see if he changes. I know you said you want non-breaking up advice, but if he isn’t willing or able to change you have to decide if this, potentially permanent, incompatibility is a deal breaker for you. In any case, I hope things improve dramatically.
I’m thinking 🤔 possibly setting up a certain time period where you can both enjoy this. So not every time you are intimate but maybe every third time or something. I feel no matter how you address this you might hurt his feelings. But if he’s an honest caring person he should understand this isn’t “your” kink and respect that you are doing his thing to please him. The last thing you want to do is stop it as he will go and find other ways to express his kink. Also you both could maybe explore other types of kink that you might enjoy. Mix it up a bit. Best wishes.
Dump him.
So, an interesting thing about sissification porn, is DOES actually mess with some neural pathways in your brain (at least some of them do, depending on the music that is attached to it) and if he’s watching that stuff semi consistently, he may reach a point where he can’t get aroused properly without the ‘roleplay’. Just some food for thought.
As for solutions: he’s being selfish. You need to put your food down and enforce your boundaries. If it’s a turn off for you, tell him that. You being less aroused during sex is a bad thing. Either make it a special occasion thing or schedule it. Like “on Fridays but only if we’ve had normal sex X times this week beforehand” though monthly or every other week would probably be more sustainable. That’ll give him motivation to not be a selfish shit.
Men are often quite goal oriented, so I think the schedule thing will work. He might try to say you’re withholding sex from him if you do that. And if he does that, that’s when I’d reconsider the relationship, because that’s just him wanting to do the sex his way regardless of your feelings.
I don’t really have any advice for you, I just wanted to say I think you’re very mature for the way you’ve discussed this with us! A lot of girls would have written it off as him being gay, but you are open to actually dissecting it all and I think that’s cool
OP, this seems like less of a kink issue and more of a selfishness issue. I hear all of the things you were saying and I think you’re justifications for not feeling comfortable with this kink are valid. Sometimes people don’t like each other’s kinks. But, that doesn’t seem to be the issue here. Not really.
Your boyfriend does not care about pleasing you sexually. You did not make mention of your own kinks, I’m assuming because they’re irrelevant to and/or aren’t being explored in this relationship. Not only does your boyfriend know you don’t share his kink, not only is he not making very much of an effort to accommodate your distaste for certain sexual activities, but you have not mentioned a single instance of him trying to explore or accommodate your desires during sex. Kinks aside. How often does he try and please you and see what it is that you want in bed? How often is sex about you? Because right now it’s all about him.
You seem like a very open person. I would encourage you to try and be more open and accommodating to your own wants and desires.
>then he starts calling me “mommy”
just gave my vagina the ol’ jumpscare
You can’t help what you like and don’t like and you don’t have to apologize for it. “Hey, that’s not my thing. Love it for you, but not for me.” Seems like you aren’t compatible
This guy has kinks that the overwhelming majority of women are going to find offputting and a dealbreaker. I get that people here are kink-positive, but the reality is that he is going to have an extremely hard time finding anyone who genuinely get excitement out of doing this with him.
I think honesty here is the best policy. On some level he has to know this doesn’t do anything for you. It just seems like there is a big sexual incompatibility here.