boyfriend cross dressing

[clearlywaiting]

I know there are resources out there, but I'm looking for some suggestions, or at least personal experiences. I've started to date a guy and this weekend he told me that he sometimes likes to dress up in women's clothing and masturbate in them. I'm a pretty open-minded person, but I'm not sure what to do.

One of the things that is on my mind is that I am afraid that he is secretly gay because he lives in a small southern town. But he said that he likes only women, and that it's just a turn on for him. Does anyone have any suggestions for this. I'm a 31 year old female and am not closed minded but I'm not how to handle this situation. I want to understand more about it, but I feel like anything I say will come out as insensitive, and he's such a good guy. I'm really torn.

Thanks in advance!

 

[emap]

Take him at his word silly, not all drag queens want to be sleeping with men. Not saying he is one, just that certain men like to feel sexy and hard to feel sexy in the clothes they make for men.

No seriously, the clothes tend to be a bit abrasive and not smooth, even their suits are like that. Not all guys want to wear abrasive clothes, I often ask my guy how he stands wearing them all the time cause I normally take them off him shortly after we start cuddling.

Rupaul actually said it best, dressing up like that gives him a thrill that you don't get in a tshirt and jeans.

 

[where]

I know and sell to loads of cross dressers and not one of them is gay. I say enjoy it but watch your expensive make-up!

 

[sunandshadow]

Did you try the forum search function? I'm sure we've had girlfriends or wives here asking the same question before, and also boyfriends or husbands who like to crossdress asking for help about if and how to tell their gf/wife about this.

Anyway the thing you should do is try to understand the psychology of crossdressing. There have been psychological studies done which show clearly that at least 2/3 of real life 'hobby' crossdressers are straight, despite the fact that in a lot of fiction it is presented as a characteristically gay activity. On the contrary, most gay men do not want to be women or be mistaken for women because they are attracted to and admire masculine things. Straight men on the other hand tend to be intensely interested in characteristically feminine things like lingerie, pantyhose, high heels, whether these are on women, used as a masturbation aid without being worn, or worn to cause arousal and/or during masturbation.

What I personally would want to know, if I was dating a guy who occasionally dressed, is if he felt like he was mentally female, a woman trapped in a man's body, or whether he was a submissive and wore the clothing as a symbol of vulnerability or obedience, or basically what he imagined while dressed.

 

[Mansa Musa]

I know there are resources out there, but I'm looking for some suggestions, or at least personal experiences. I've started to date a guy and this weekend he told me that he sometimes likes to dress up in women's clothing and masturbate in them. I'm a pretty open-minded person, but I'm not sure what to do.

One of the things that is on my mind is that I am afraid that he is secretly gay because he lives in a small southern town. But he said that he likes only women, and that it's just a turn on for him. Does anyone have any suggestions for this. I'm a 31 year old female and am not closed minded but I'm not how to handle this situation. I want to understand more about it, but I feel like anything I say will come out as insensitive, and he's such a good guy. I'm really torn.

Thanks in advance!

If he's a decent man, if he treats you with respect, if he's good in bed, and if he's holding down a job, then you should just roll with it. Life could be worse: you could've met a man who was far too ashamed to admit to thatside of himself. Then you'd be another one of those "I had no idea..." women on the local evening news.
t least, he'll have an outlet for his "deviancy". He won't find himself in a seedy hotel room, indulging in his vice and worrying that the police may decide to raid the premises at any moment.

 

[Ling]

Speaking as someone who's been though this (on the male side), here are a couple of things to bear in mind: First, there are worse things he could want to do - ultimately this is just a style of clothing he likes to wear that society doesn't think he should

Second, telling you was probably not an easy thing to do for him (see above).

I assume that from "small Southern town" you mean somewhere that gay people are not welcome (I'm not from the US) so I don't know how much this applies, but if he was doing it for the "drag queen" kind of thing then you could probably assume he'd be out doing it, which I assume he's not as you didn't mention it. You also don't say what sort of clothing he likes to wear. I personally feel there's a difference between wearing some nice knickers because you like the feel of them, and wearing a bra, blouse and make up.

I have found that online communities for men who do this kind of thing seem to be entirely made up of people posting "heres some pictures of me what do u think" and/or "heres what i wore to work/on a plane/while shopping/in the car" - so it can be difficult to talk to anyone properly about it.

Like Mansa Musa said, if everything else about him is fine, go with it. You might enjoy it

 

[baited]

He is being honest about wanting to wear women's clothes, if he was gay, don't you think that he would be honest about that to. If he's not too embarrased about it, maybe you should have him dress up for you someday, to see what he wears; you might like it.

 

[rkymtnkng]

hello first post

I love to trade seats,chairs roles or sexes. Some guys like me just want to hand the keys over sometimes. dress him up an peg him.

 

[VelvetDarkness]

Youtube some Eddie Izzard standup. He is a happily married, heterosexual cross dresser and he usually tackles the issue during a show. Memorable quotes include:

"All this and I'm wearing heels. Mustn't fall over though. If you're a woman and you trip over your heels it's cute, if you're a man... well... your life's over."

"Men generally are all: running, jumping, climbing trees. Transvestites run, jump, climb trees and then put on make up when they get there. Think of me as a male lesbian. That's about right. A butch one who carries all the shopping."

This guy has made a point of being honest with you from the earliest reasonable opportunity. Some women don't get to hear about this stuff until they're married or until the guy ladders one too many pairs of their tights and gets rumbled.

He has told you but that may be where it ends. He may not require you to do anything except accept it and not freak out when you spot a pair of lacy knickers in the laundry basket. Ask him if he wants your support in any way. To many men this is a very private thing that they prefer to do alone. My Master is the same about porn. He enjoys it but not when I'm around. I don't care that he watches porn, I'd watch it with him if he wanted to but he prefers to be alone. It may be the same kind of thing. Don't automatically assume that you have to act on this info. Just be accepting and wait and see when he brings the subject up again.

 

[TheHeinz57]

Thanks Velvet...i youtubed him and got sucked into watching that guy for a good hour =P

But yeah, if he's being honest with you he must care about ya.

 

[KokopelliRises]

Thanks Velvet...i youtubed him and got sucked into watching that guy for a good hour =P

But yeah, if he's being honest with you he must care about ya.

He is quite that addictive.

But seriously, he obviously cares about you to tell you something that personal. Maybe you could probe into it a little more, see what exactly he likes about women's clothing and maybe see if you can help him find something (clothing-wise), so he knows that you aren't freaking out.

 

[peachydreams]

You might enjoy his dressing up. I have a friend who loves the silky, sexy feel of women's lingerie and believe me he is VERY straight. He loves to take my panties (especially if he gets to take them off me) and feel them slide over his erection. It can be very sexy, just go with the flow and find out what he enjoys.

 

[A_Kefka]

He went ahead and told you, so there isn't much reason to think he's hiding anything. Almost all straight men like the look and feel of women's lingerie, a few just like it on themselves as well as the woman they are with.

 

[RUbensBeautY]

I used to date a guy who had a thing for wearing female lingerie. My feelings have been quite mixed about this information even though we had been very open about most intimate issues from the early beginning. Thankfully we had a few open, even if slightly embarrassing conversations and they definitely brought us closer.

If it bothers you or you have questions, be tactful about it and make sure to chose a good time and setting, but I would still encourage you to talk to him. It is not about blowing up the issue but sorting it out for yourself which is also in his best interest.

As for me, in the end it came down to the question what was the most important to me and he was the natural answer. So ... I got him a pair of blood red lacy panties for his birthday as a special gift and we had many great times of me teasing him about how hot and spankable his ass looked in them as part of our bedroom games - and believe me, it did!

I wish you good luck and for things to work out for the two of you.

 

[ZoeBird]

I don't get the connection between being gay and living in the south. You think he may be secretly gay because he lives in the south?

 

[SweetErika]

I don't get the connection between being gay and living in the south. You think he may be secretly gay because he lives in the south?

Considering this thread was started last May and the first post is the OP's one and only post, I'm pretty sure you're not going to get an answer.

I wonder what's up with all of the dead thread bumping in the past few days. It seems like we suddenly got several new people who decided to go through the archives and bump, bump, bump. Maybe it's due to Spring Break.

 

[ZoeBird]

Considering this thread was started last May and the first post is the OP's one and only post, I'm pretty sure you're not going to get an answer.

I wonder what's up with all of the dead thread bumping in the past few days. It seems like we suddenly got several new people who decided to go through the archives and bump, bump, bump. Maybe it's due to Spring Break.

Oops, I didn't even notice the date on the thread. I just saw it on the first page and posted on it.

 

[E_S]

I know there are resources out there, but I'm looking for some suggestions, or at least personal experiences. I've started to date a guy and this weekend he told me that he sometimes likes to dress up in women's clothing and masturbate in them. I'm a pretty open-minded person, but I'm not sure what to do.

One of the things that is on my mind is that I am afraid that he is secretly gay because he lives in a small southern town. But he said that he likes only women, and that it's just a turn on for him. Does anyone have any suggestions for this. I'm a 31 year old female and am not closed minded but I'm not how to handle this situation. I want to understand more about it, but I feel like anything I say will come out as insensitive, and he's such a good guy. I'm really torn.

Thanks in advance!

You're going out with a pansy. Bloody hell. Lock away your expensive underwear, he might stretch it.

 

[SweetErika]

Oops, I didn't even notice the date on the thread. I just saw it on the first page and posted on it.

I figured as much. It just caught my attention with the unusual amount of bumping in the past few days.

 

[A_Kefka]

I know me I don't look at threads that haven't had a post recently, but if it has I don't bother to look for a huge gap in the dates to see if it used to be dead.

 

[Eilan]

One of the things that is on my mind is that I am afraid that he is secretly gay because he lives in a small southern town.

I don't know how I missed this thread the first time around, but this is some funny shit!

 

[Slider1234]

does he get fully decked out in women's clothes?
panties are actually pretty comfortable, but thats as far as i ever went when my g/f asked me to try em on

 

[Joanne4Ever]

Take it from me, I started out just cross dressing & it led to fully dressing, then wearing full makeup, then growing my hair & nails, then getting my ears pierced & having my eyebrows waxed into thin, highly arched lines, then getting my hair cut & styled into a feminine style, then throwing out a majority of my male clothes, and finally, going out and sleeping with men. It cost me two marriages, both times I was caught fully dressed & made up performing oral sex on men. My new girlfriend is very accepting of my dressing up every day, I have yet to tell her about how I like being with men & how I really want to be a woman. I have been dropping hints about wanting to take hormones to grow my own breasts & she seems to be pretty positive about it. She does my hair & makeup for me & goes out with me to the clubs, she even made a comment once about finding me a boyfriend. We get our nails done together & go clothes shopping, she has even suggested I get my hair colored. She does not seem to mind that I spend around 95% of my life as Joanne & she recently has started helping me to find a job where I can work as Joanne. My advice to you would be get out before this takes over his life & winds up hurting you.

 

[davion2308]

Compliment

Consider it a compliment that he's told you something early in the relationship and he is being upfront about it. Just because he's interested in women's clothing and they are a masturbatory aid for him doesn't mean he's gay. Just because he says, "Hey, can we try pegging?" doesn't mean he's gay. It's too bad the first thought of yours seemed to go that direction.

Don't be torn. You said you're open-minded, good. I won't tell you what to do but if this popped up with me, I'd let the person talk it out and understand where they're coming from. Do they want me involved with it? Am I comfortable with that? Is it just during "Them" time and I don't see or experience anything?

I would explore the desires and turn-ons and see how I feel and make a decision, if any, afterward. That's just me.

Good luck.

 

[pplwatching]

Consider it a compliment that he's told you something early in the relationship and he is being upfront about it.

While I agree that it was a good sign that he was willing to be up front and communicate, he told her back in 2008 Hopefully they worked through it.