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New boyfriend wants to dress in a dress during sex

Tagged as: Sex, Troubled relationships<< Previous question   Next question >>
Question - (2 October 2018) 10 Answers - (Newest, 6 October 2018)
A female United Kingdom age 41-50, anonymous writes:

I have just got a new boyfriend and he told me something a couple of days ago, he said he wants to dress in female pvc in the bedroom. He doesnt want to wear wigs or do make up just wear a dress and certainly doesnt want to go outside in public. At first i thought he was joking but he is being serious. Im trying to get my head round it. He said he wants to try it a couple of times and if i cant deal with it then it wont be an issue. Im then thinking if he cant do that with me will he go find someone who will. Ive told him all this and he says hell stop if i cant cope with it. Im struggling to get my head round going to bed with a man in a dress. I know theres drag acts and men dress up as a woman on stag dos and things like that im not against people dressing how they want i have no problem with it , its just an issue with the guy im in a relationship with, has anyone ever had this in their life and how did they deal with it ? thanks

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A female reader, anonymous, writes (6 October 2018):

If you don't want to and the idea repulses you then you say no. You now also have a good idea of his fantasies and I hazard a guess he has done this already unless he just happens to feel really comfortable to have only ever asked you, only he knows that. We all have fantasises and different attitudes to sex and what goes so this is about compatibility, only you know if you would be okay to give it a go or to say no.

But do not feel you have to do anything you are not comfortable with x

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A female reader, Ciar Canada + , writes (4 October 2018):

Ciar agony auntNo, I can't say I've had that in my life and nor do I plan to.

Frankly, for a man, the one I'm dating anyway, to even express an interest in doing so would be like a proverbial; cold shower to me. It would forever spoil my view of and feelings for him. So this just wouldn't work.

My suggestion is to stop trying to get your head around it. You don't have to be open to everything. And you8 don't have to try it to prove you don't like it. It's not important enough to be worth it.

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A reader, anonymous, writes (3 October 2018):

Sorry!

Another correction:

"He waited to get you fully-committed; before springing this over-the-top surprise on you."

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A reader, anonymous, writes (3 October 2018):

[EDIT]

Correction:

"I think I deserve the option to decide if I still want to commit, in spite of some unusual quirks."

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A reader, anonymous, writes (3 October 2018):

If that's not what you want in a man; don't try to adapt to every kooky outrageous situation that comes your way. If it was cool with you, you wouldn't have written a post about it!

He waited to get you fully-committed, before springing this over-top surprise on you. Now you're questioning yourself, if you need to change your values and perceptions to sleep with a guy in a dress?!!

Seriously, though?!!

If deep-down, this is a deal-breaker for you; don't let desperation for a boyfriend make you settle for one in a dress! Can you wrap your mind around it? If not, you don't have to! I agree with Code Warrior!

Even I, as a gay man, would not prefer to sleep with men who like to wear dresses. They're not my type! I like dresses on ladies. No offense to drag queens. I don't date or commit to drag queens, or cross-dressers; and respect their opinion, if they don't like me. We can peacefully and respectfully co-exist. We don't have to have sex with each other!

Nothing against those who like it; but I don't like things sprung on me, especially something that drastic! You should have been told this before you made him your committed boyfriend. I am open and transparent with everyone; especially someone I love. That's not the kind of surprises I want in my relationship! I think I deserve the option to decide if I want commit, in spite of some unusual quirks. He didn't offer you that choice. He decided for you, once he had you cornered.

If you want out, no need to feel guilty about it. He tried to back-door you with this; that's deceptive! What comes next???

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A female reader, anonymous, writes (3 October 2018):

I would not want or trust a man who has values so far off from my own. This, my dear, is a red flag, and it is ominous of what's to come. Personally, I would not wait around to find out. I will bet in time much more absurdity will reveal itself and a racier past than you had imagined or want/need to handle will slap you in the face. It's new right now. I'd waste no more time and move on. Relationships where values and sexual preferences are mismatched are doomed to fail. Eventually you will resent his craziness and he will resent your being more conservative in comparison.

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A female reader, Andie's Thoughts United Kingdom +, writes (2 October 2018):

Andie's Thoughts agony auntAs this doesn't violate you, I suggest trying it once. If it was another fetish where you were at risk of feeling violated, then I wouldn't advise trying this. However, as it's a harmless one, it's worth giving a go if you want to try to make this work.

You need to ask him how important this fetish is for him to be turned on, BEFORE you try it (but not in a judgemental way). If he can't get turned on properly without it, then he's probably not for you because most people need to be sexually compatible. After asking, try it once to see how you feel. Try to be open-minded, in case you may feel okay enough to give it ago once every few months, as well as any safe fantasies you may have.

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A female reader, Youcannotbeserious United Kingdom + , writes (2 October 2018):

Youcannotbeserious agony auntI suspect he has already tried it with others and found this is what turns him on. It's a fetish, a fairly harmless one in the grander scheme of things, but it's not everyone's cup of tea.

I would suggest (you can obviously choose to take or leave this suggestion) you try it once. You never know. Seeing him all turned on and "buzzing" may be a turn on for YOU. If you find the whole thing unbearable, then you need to be honest so that he can decide whether it is a deal breaker for him. As your relationship is new, it shouldn't be too difficult to end things and move on if you decide this is definitely not for you.

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A female reader, Honeypie United States + , writes (2 October 2018):

Honeypie agony auntJust be honest with him.

If this is NOT your thing and you don't even WANT to try it, it's OK. JUST tell him.

I don't think he will go elsewhere to try this.

I would probably ask WHY he wants to try it and go from there.

You are not alone, this would not be a "turn on" for me either.

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A female reader, anonymous, writes (2 October 2018):

I don't think this is a standard relationship and at your age I think you might be looking for something that is more in line with the average standard.

In fact I dont feel this is a serious relationship at all!

You've only just met this guy and already he is starting to make extremely unusual requests.

These are things that are red flags and should indicate to you that he is not a good boyfriend for you.

Because by breaking your boundaries of normality he is getting you to shift your perceptions of what you want from a relationship and this is only the start of it.

Maybe he wants two fried eggs with ketchup on his nipples sunny side up.

You need to ask yourself if you should acquiese or if you would prefer a male partner with different boundaries and sex foreplay such as hugging and kissing after a meal out.

Its easy to figure it out.

You just ask yourself if it has been a lifelong dream to have sex with a man in a dress.

If its not your thing the best thing would be to find someone different with whom you can feel more comfortable.

And let this guy go to see if he can find a partner that wants a man to wear a dress for sex.

Its that simple!

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