Crossdressing Boyfriend

[Anna123]

Hello everyone...

I am just posting because I have some questions about crossdressing.. I am 19 years old and my boyfriend has recently opened up to me about his crossdressing. I am completely comfortable with it and have since bought him heels, makeup and seen him in female clothing (although never all at once, we always seem to do it in stages). I understand that it is an urge that he gets, and that he does not want to be a women or be with men... With him also his main interest is heels, however he does enjoy the rest of the experience as well..

My only issue is that although I enjoy shopping with him, he always wants to go (which I dont mind) but then gets moody whenever we do.. It is mainly whenever we look at heels, I will quietly ask him if there are any that he likes and he will grumpily respond 'well I dont know do I?!'. I think it is mainly that he is worried to touch any of them or appear too interested in case other people realise, however I do not think they would as they are more likely to think he is helping me choose for myself or a friend etc, and even if they did, we do not know them so it would not be the end of the world (although I understand it makes him nervous).. I am asking for help in how to make these trips more relaxing for both of us, at the moment I do not really enjoy them as he gets so grumpy which often ends up with me being frustrated and not wanting to help him at that time, and then it escalates...


Thankyou for your help

Anna x

[Laura912]

You have the answer in your own post. He is nervous, young, and regarded as a male so he gets all tangled up in the guilt which turns to grumpiness. You are wonderful for being so understanding...make sure he knows that! Be patient and coax him to being more comfortable with accepting your help. Tell him, I said he is really lucky to have your support!

[NZ_Dawn]

He is lucky to have someone so special and understanding! Try letting him know before the next shop that you enjoy and want to help shopping. (Describe it like gifl friends out shopping pehaps) But also let him know you dont like the grumpy, thats not fair. I was sort of guilty of the same in the beginning; being unsure and possibly a little fear in case things went turtle. Can he let you know how to help or respond, it sounds all very new to him. Hope it all contnues well for you both.

[Kelly DeWinter]

He should not be getting grumpy at YOU for asking a reasonable question, or making snarky comments to you. It's time he had an attitude adjustment and realize how fortunate he is to have a gf that's OK with his fetish.

[Amanda M]

Anna - first of all, thanks for being here, for him and for you. This is, as has been said, about doubt, nervousness and fear. He knows that you are pretty comfortable with what is going on, clearly, but I suspect that at the back of his mind, there is a nagging doubt that you are such a gem!

I wouldn't tell him as Laura suggested (sorry Laura) that he is lucky to have your support. He already knows that, and is being very self controlling. Unlike many, who get confused in the Pink Fog, he does not want to alienate you by seeming too keen.

The fact is, Anna, that I have been there! Often I have thought "I would kill (or at least maim) for a pair of these, and yet, and yet, I would not say that to my wife. Totally and irredeemably stupid on my part.

May be hand him a fistful (or a small handful) of dollars and say go buy heels. I love your taste, and I am so looking forward to a surprise!"

To him - and strangely, to many of us here, ladies like you are a pearl beyond price.

[Katey888]

Dear Anna,

You're both so young and have so much to develop around confidence and relationships.. most of it is fun..

Sounds to me like he just needs a bit more confidence in being with you, checking over potential purchases, and knowing that being with you will mean he is 'safeguarded' from suspicion... Take a bit of time - keep trying, but be patient...

Perhaps before you shop you should agree that if he feels uncomfortable, you should stop shopping for him for a while, exit the store and just do something neutral... get your confidence back, and then go back to it... It shouldn't be feeling like a race or pressured... Talk to him and try to find out how to make him feel more comfy.

And btw - you are a dear girl for being this way towards him.. there seem few that are as open-minded as you around..

Katey x

[Amanda M]

Sorry, Kelly - fetish???????

[anonymousinmaryland]

Laura 912 has the answer. I hope he is as good to you and for you as you are for him. Hugs.

[kimdl93]

here's the deal. As noted above, he's young and although he wants to express this part of himself and trusts you, he's coping with the usual burdens of self doubt and embarrassment that often plague CDrs ...sometimes throughout their lives. The grumpiness is in a sense, his effort to preserve the male pretense.

So how to get past it? Well, it really starts with conversation. He needs to be reassured that you see this as an acceptable and positive thing....but he also needs to work on accepting himself. He needs to learn that he is OK....and that many young males have similar interests. He needs to understand that being a cross dresser does NOT mean he is a pervert, nor a criminal, nor diminished as a valuable human being. It took me decades to reach that point, but with your patient support and encouragement, he can get there much more quickly, and shopping and dressing up can become something you can share and enjoy.

[Nadine Spirit]

When I first went shopping for my own female items, I was totally and completely embarrassed. I really thought that I would be laughed at and ridiculed, especially if I tried on female shoes while dressed as a male. And trying on shoes is pretty much a must if you want to actually end up with a wearable pair. It has taken me quite some time to be comfortable with who I am.

The only way I have arrived at any sort of comfort level that folks were not going to start poking me with pitchforks and yelling "monster!" is to actually experience the total non response of society over and over and over again and again.

I am sure that his moodiness is not with you, but with himself. Most of us are quite annoyed that we want what we want and we totally do not understand why. So in the moment of buying stuff, in the early stages, we are totally torn, I want the shoes, but I hate myself for wanting the shoes. I want the shoes but people are going to think I am a freak if I try them on, thus I hate myself and I hate others because I want the damn shoes!

[Teresa Monsivais]

Hello Anna and welcome to this group. It sounds that he isn't comfortable yet and may be very much his nervousness. I wonder if he gets extremely nervous when you whisper to him because he may think someone in the store may have heard you tell him if he sees anything he likes? (despite you being discrete). It may make him think like all eyes are on him (obviously an irrational thought) and he is afraid of getting outed etc. Does he get moody with other things when he is stressed, overwhelmed or nervous? If so, it may be the way he handles stressful situations in general. Be patient but also he needs to work on communicating his feelings to you. If he does not, maybe you may want to set some boundaries. Maybe something like, : I really enjoy shopping with you and supporting you on your crossdressing but I can not be part of this if you continue to speak to me in a way that is (insert feeling i.e. hurtful, aggressive, abusive etc).

good luck

Teresa

[Kate Simmons]

It won't be more relaxing to him until he is ready for it to be. Some things just take time my friend.

[KittyD]

Hi Well tbh with you I'm 42 & I still get a little silly about buying clothes & shoes when I go out hunting for the good stuff :P Online shopping is a great way to over come that in a way... plus if youv'e got big size 10 feet like me the internet is a dream come true for heels LOL
I think its an age thing & the older Ya get the less you care about what other people think about you and what you enjoy doing in your life and with your time
You sound like a totally uber lOvely person ox

[Jacky Aikou]

Hi Anna, welcome to the forum! Your bf is truly lucky to have somebody as caring as you.

I can't offer much other than what's been posted already (I especially agree with Theresa's and Nadine's replies), but I regret to say I've acted in a similar way to my wife (GF at the time) while shopping in the past. Shopping for feminine clothes was sometimes a very tense experience, and I would be unappreciative and short-tempered even though my wife was just trying to help me. For me, it was a self-esteem/guilt issue (me shopping for women's clothes is wrong/I am a lousy man) plus being overwhelmed at the same time (Look at all these clothes! I am lost!). I had no confidence and wouldn't let myself enjoy the moment and take the time to honestly think of fashion and just shop. I took that stress out on my poor wife.

Maybe your BF feels similarly? Airing the topic with him might help - hopefully he will be receptive to an open talk! We're not always as mature as we should be when we're 19. Good luck! Just FYI, I worked on my attitude and try to be much more considerate toward my wife and people in general now.

[Anna123]

Thankyou everybody for your replies!

They have all been very helpful..
It is true that this is something new for him and time and support can only help him to become more comfortable with it I will definitely look in to online shopping with him some more as it will be a good solution for when he wants a quick and easy fix of clothes/shoes etc.. and as part of the fun is in the actual shopping process I will continue to go with him but perhaps yes if he is showing discomfort I will suggest another activity for a while until he feels better again.. and if i need to i will mention that he is being grumpy and that I dont like it..

It also does sound quite fun to give him some money and see what he comes back with! Perhaps when he is a bit more comfortable I will try that :P

You have all been very helpful and sweet,

Thanks a lot!

Anna x

[Teresa]

Hi Anna,
Your boyfriend is very lucky but at the moment he won't see it like that, he may be confused by the role you're playing when shopping, it's not that many years when perhaps mum shopped for him in other areas. He may get over his nerves better if he shops alone and develops a better rapport with SAs, it does get better and can be fun, perhaps better not to encourage him to shop dressed for the time being that's a different ball game.
As others have suggested online shopping is another way round the problem but won't cure his nerves.
The other problem you could have is that he doesn't know where he wants to be with his CDing so he gets tetchy when he's choosing things because he doesn't know when and where he is going to wear them.
The other question is he a member of the forum ? It could help him to find his answers.

[Tracii G]

Welcome Anna and I agree with all the answers given by all.
He needs to understand just how lucky he is to have you as a partner.
He may be dealing with a lot of things right now that he won't talk about only because he is not sure who he is just yet.
If you can help him discover a few things that is a good thing but don't push him too hard for answers yet he needs to grow on his own.
Its possible to be comfy in both male and female modes just finding the balance is the key.

[Confucius]

First of all, you sound like an absolute angel. Really!

You are also correct that your boyfriend is nervous that he will do something that will "out" him, and his big secret will be exposed. If that happens then he is afraid he may have to kill himself. So what should you do???

First of all when you go shopping reassure him that he has nothing to be nervous about. When you go shopping use some code words. For instance, if he likes something he should respond by saying "it looks like your old shoes". He may just want you to make most of the decision making. Pick a few shoes you think he would like, and ask for his opinion. When he says, "this looks like your old shoes" then that's the one. You may even do a practice run in the privacy of your room before you go shopping.

Since you know that shopping in public makes him nervous you should always rehearse before going out for the real thing. He will develop confidence with time.

[Allisa]

Just one more view of your problem not mentioned, have you ever watched a man shop? It's in the door, go to what you want, pick it up, go to the register and pay ,then leave. No comparing items,now add to this gender confusion, shame, embarrassment, lesser knowledge of product, etc. and you have grumpy man. Some of us have to learn how to shop and enjoy it. It may be that simple. He is very lucky to have you in his corner, please be patient, male ego is at play here. He will find himself and the fun will begin.

With all luck and joy Lisa

[MatildaJ.]

You might also try shopping further from home. He may relax more if he feels less worried that someone he knows might see him trying on women's shoes.

[kathrynt21]

Anna-
As you can see these types of posts usually get a lot of responses. That's because we have all been there.
Your BF, as has been stated, is young and nervous.
BUT, he is totally and completely lucky to have you as a GF! We all want that. The acceptance and patience you are showing is commendable and shows your love and affection for him.
He will get more and more used to things and will be more comfortable as time goes on as he accepts HERSELF more and more.
When I first started shopping, it was for "someone else." "A gift."
I am totally comfortable shopping with my wife because you are correct in assuming that people will think we are shopping for her.
After a while I started being more comfortable and now I shop alone all of the time. This morning in fact! Haha.
You'd be surprised how little other people care.
There is a great quote from a John Steinbeck novel called "The Winter Of Our Discontent."
"You wouldn't care so much about what other people think of you if you knew how little they did it."
Keep being supportive and if she wants to talk to someone (or you) I'd be happy to help.

[pantyguysb]

Unfortunately, I have done the same thing. If he is anything like me, he appreciates your support and my guess is he will become more comfortable with it. Maybe come up with a plan before you head out. Code words maybe?

[dana digs sweaters]

Welcome Anna,
and as Jessm said, maybe a little further away mileage wise, may ease his "fears".
AND! tell him that in do time he will laugh at himself for his "fears" of shopping for any female item.
We have ALL been there

[mechamoose]

Laura 912 has the answer.

I agree. He doesn't feel confident.

Shop online. Zappos, Payless, Torrid, Shoes of Prey.. LOTS of choices. You get to browse together without him being embarrassed.

Part of it may be that he doesn't really *know* what he likes.

Lots of sites let you do wish lists. Have him go through some sites and point out things he thinks are attractive. Not attractive on HIM.. just attractive.

Then go through that and pick the best few. Have him try them on, walk around... wear them for an hour.

He will either like them or he won't.. he might be 'iffy' (that counts as a no).

He could be, regardless of what he says, be 'timid'. Afraid of letting that part of him out and getting it all wrong... of getting hurt.

You are being *wonderful* for supporting him. Continue to encourage him. I used to be a flannel and corduroy kind of guy.. a wonderful woman helped draw me out of my shell. ( My Intro )

<3

-MM

[Tara Power]

I wish I was lucky enough to have a gf to go clothes shopping with (heck id settle for a gf right now!) But for me whenever I started shopping by myself my god it was so nervewracking and awkward but usually ended up in buying things in the wrong sizes or something I didn't want, just for the purposes of buying something. I can empathise with your partner for sure!
When I used to get dragged round shopping malls with my ex (before I dressed) I hated it, getting trailed round shops it would take ages and I'd get tired and hungry and ratty just like a child, now I would love it as it would give me an opportunity and cover just to spend hours looking at all the different clothes without feeling weird.

As for my suggestion;if your other half has a female name they like to use, use it when youre out shopping with him e.g. lift up a pair of heels "Do you think that X would like this?" Or I think X would look great in this top, what do you think?" All he needs to do is give a grunt for yes or no if he feels really reallly awkward. But make suggestions, give compliments as if you were talking girly chat shopping with one of your girlfriends buying clothes for a friend.

Overtime, he'll be more confident and learn just to own it! When he sees himself all fully dressed up and looking amazing the guard will come down and be more vocal about getting what he wants. It was for me at least starting out very unsure because I started with buying a few things and didnt feel right about it until top to bottom was fully dressed and could see the potential woman was there all along, hidden.

Hope ive helped x