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I Have A Boyfriend that goest Out Crossdressed

Ok! Iam Female by birth, and i have a boyfriend that loved to go out in public crossdressed, I found out by accident and admit at the time I didnt take it to well, I felt betrayed and threatened, not to mention angry as i felt he didn't trust me enough to express his feelings. after lots of talking and explaining and me asking loads of questions, it was agreed that i didn't have any problem with it.but didn't want to meet his feminine other self. so he did it in secret and when i wasn't there. trouble was/is that to be secret about it you have to 1 Be a very good lier, and 2 Have a good memory.
I could tell when things had been moved, etc eventually i gave in and met her. he was embarrassed and must admit I didn't make it easy for him. Give him his due he did it. and i was impressed.

A few problems arose and this is the reason for this post, and maybe it may be of some help.
Tell your wife or girlfriend, it wont be easy but in the long run its best, if you don't and she finds out and isn't understanding she will leave, but She will most probably leave anyway if she catches you.
Plus if you tell her and she is understanding then the love understanding and trust is still there, and will continue to be there.

I have done my homework, but i do still have questions
Why do you go outside? My boyfriend isn't gay but wanted to pass as as a woman, and did look the part, so going outside wasn't really a problem because he could pass. but Ive seen so many cross dressers or what ever other title that fits going outside that don't pass or even come close. is it to shock? don't get me wrong to do it takes guts and iam not mocking, I am just asking a question. and before the answer comes back that there is ugly women too, yes I agree.

Also there seems a band of cross dressers that for what ever reason think its ladylike to ***** off and prance about in their underwear, Why? is it the risk of getting caught? or to shock?

I know it cant be easy, Ive seen it first hand that quiet country roads are an ideal place to experiment and to practice, that's fair and understandable. But on that point a little advice, people, both men and women when they walk do so for a reason, so they are either going somewhere, or have been somewhere, they walk with purpose, even if it is only a stroll through the woods or whatever, lift your head up and be confident, walk with purpose, yes you will be seen, isn't that the point? if you look like a lady and act like one, yes there may be a doubt there if your seen. But people don't want to appear stupid so wont say or do anything just in case they are wrong.

High heels, Hey I love them, but i dint wear them all the time with every outfit, before you go out have a look out of the window and look what the other girls are wearing and blend in, that also goes for belt length mini skirts in winter, OK not the every day usual norm, and that goes for other inappropriate clothing. I know it sounds obvious, but take a look on you tube or the like and see for your self.

There is an awful lot of Fabulous and amazing cross dressers, and i see that their effort being undermined by the quite frankly monsters. or the ones that are feminine in every way, their looks, their walk, the way they hold them selves everything, then you see them stripping off or flashing to traffic, that's where it falls down, and the battle is lost

I don't wish to upset anyone but having a boyfriend that cross dresses and goes outside in public Ive seen a few things, and learnt a lot.
Thank you for you time ladies
PS As a woman if you want to talk or want my opinion for what its worth, let me know.
pashon8 pashon8 41-45, F 19 Responses Oct 29, 2012

Your Response


I'm a cross dresser that deep down when in fem wants t be just another girl among the other girls. My taste in outfits is current fashions not slutty like some Rocky Horror character.

In addition I feel a part of my soul is female sand needs to express herself.

Somebody once said "We are old souls" I like to believe that in my past life I was a female and maybe my wonderful life was cut short. If it's true we get more than one chance at life. I look forward to hopefully having another chance at life being female.

Oh I wish we all were able to have more than one chance in life. Wouldn't that be awesome? I would love a do over. I don't believe we do get another chance in life but it doesn't hurt to dream.

Guys that dress up fell like a girl in their mind and even tho they dont always pass, they still feel feminine inside and what to go out and be around women to kink of connect with them. Its not really a sexual thing, its them wanting to be excepted for who they are.
Thats why they go out, if they are excepted, they feel more like the female they are trying so hard to be like.

It is a wonderful feeling to be accepted as an equal and looked at as someone who totally understands women. Maybe we really don't, but seeing us walking a mile or more in your shoes shows that in our heart we want to connect on an equal level with women and experience femininity first hand.

What does, "...fell like a girl..." mean?

I agree that some CDs do it quite well. Others look like men in women's clothing - and it can be frightening. I think your points about going out in public are spot on.

You make some very good points. There are many different motivations for crossdressers to want to go out dressed and leave the safety of being behind locked doors.
I am fortunate to be able to pass in public and enjoy things like going shopping at the mall. I dress conservatively and appropriately for a day at the mall. I want to look and feel as feminine as I can so I will wear a dress, stockings and short high heels. I will wear a knee length dress or long skirt and blouse, nothing flashy. I don't want to draw attention to myself, I just want to be treated like any other woman.
In defense of those who go over board I think it's because they know they can't fit in anyways so go for broke and be extreme and try to experience the ultimate in the short period of time you have.
As a woman I don't think you have a need to put on a mini skirt and high heels to go to the gas station. I'm sure there are times you like to wear a mini skirt and heels, but you will wear them when your going out to a club or dinner. Many crossdressers don't get an opportunity to go to a club or out to dinner so they put on their mini skirt and high heels to go to the gas station or for a walk on a lonely street. If they only dressed appropriately when they venture out they would never experience what it's like to dress sexy, and we all want to experience that from time to time.
I hope I make sense and thank you for your story. We all love to hear from women and their perspective.

What if you were on your way to a club and you needed to stop at the gas station for gas? lol

That works for me. lol Once I got up early in the morning and decided to go to McDonalds and went thru the drive thru in my nightgown and robe. I found that a fun experience. My mother use to take me to school while still in her nightgown, so why can't I go to Mc.D's in mine.

I agree with so many of your questions/points. So does my crossdressing BF. He dresses gender neutral or both male and female in public now days. He used to go out dressed as female before I knew him when he was a teen and in his early 20's. The way he put it is this: "I dressed just like the girls my age". It made him passible and didn't draw attention and make him look like a weirdo. I have seen the photos, he wore what was in style and appropriate for his age AND height. Being tall (for a female) he wore long skirts or dresses but mostly wore pants and being flat chested he didn't wear v-necks. Yet so many crossdressers insist on showing their lingerie, dressing like a "****" and wearing heals with everything... including their unshaved legs and I wonder why as well as my BF. He likes tights and pantyhose but admits that American women don't wear them, so by wearing tight or pantyhose in public is also drawing attention to oneself. Also he is saddened by the evidence that shows so many crossdressers that get on the internet are nothing more than perverts. Old sexual studies showed most CD's were straight. Now thanks to the internet and online profiles and classified adds it looks like CD's are out for sex with men and women. This hurts the CD community. He too wishes that some in the CD community would not make a spectacle by dressing so outlandish so that being a CD will become more accepted instead of being associated with perversion.

How does a crossdresser wanting to have sex with men and women hurt the CD community? I agree that some crossdressers I have seen on youtube come across as complete weirdos. I have seen some that are completely scary. This one showed him dressed in latex and his genitals were hooked up to electricity! But yeah I agree that if a CD's goal is to go out in public he should see how other women dress so he can blend in instead of drawing attention.

I'm not here to argue or debate with you LoriQ. I have said my piece once here and I am done. I don't know what goes on in other's minds and sometimes even my own. I wish we lived in a time and place where my BF, who is bi-gendered (kind of similar to transsexual for those that don't know what it means), can be himself without being prejudged and grouped into the pervert pile.

I find if people get to know you as a person first before they discover your feminine side they are much more accepting.

Very true ...

Why were you being so nasty? Why the attitude? Who said I was trying to argue or debate? What is wrong with talking? You have said your piece and you are done. Ha! What is wrong with saying MY "Piece?" I agreed with most of what you said and I said so yet you reply with a nasty attitude. Is this how you treat everyone? I would be surprised if anyone would tolerate your attitude. I don't know how you get along in society. I can be the nicest person you would ever meet but I don't give the time of day to people that are so nasty. I'd love to know how even your boyfriend tolerates you. I don't know who you think you are but you need that chip on your shoulder knocked off! You aren't any better than I am so knock it off!!

2 More Responses

I know this post is about 1 1/2 years too late. But
pashon8, I found myself in a similar situation. I have been a crossdresser since I was 5. The only thing I knew about Gay was it meant happy. I always wanted to dress in pretty girl clothes, they were just so pretty. Growing up I was a normal boy on the outside, tough guy and things.
BUT, every time I had the chance, I would adore dressing in pretty, FEMININE girly clothes.
pashon8, it was not a fetish thing, when I dressed, it was always, when possible, from the skin out.
I started buying my very own pretty, girly clothes when I was 12. My very first purchase was a pink garter panty, second was a pair of stockings-seamless with a reinforced heel and toe. I attached these to the garters of my panties.
WOW, sorry about going on so much, the bottom line is, at least you know. I'm a veteran of the Viet Nam Conflict-(-yea right Conflict----did you know that Conflict bullets can kill you just like WAR bullets).
I had to tell my wife, that I'm a hetrosexual crossdresser before we got married. Yes, at first she freaked, broke off the engagement, but for only for a day. She said that she never wanted to see or even know anything about my Crossdressing.
We have been married now for 40years.
All these years I respected her wishes.
Gotta ask, Am I being selfish (I had gone out to a Motel so I could dress) as she says, OR is it my time to enjoy something she can't relate to?
I have purged, as we all do, I had a complete wardrobe, including silicone breast forms that cost me $200.00.
I just adore the feeling of being pretty, wearing cute clothes, enjoy the sway of my skirt touching my legs, love to look down at the cute bow between the cups of my Bra and the breast forms jiggling as I walk.
I can't get out of my mind the thought of the pretty pastel lacy panties that I wear under my Panty Girdle.
My male member being TUCKED WAY back, being held by a Maxi Pad under my Panty Girdle.
I just adore, sheer stockings attached to my garters, hearing them whisper as I walk then smooth my skirt as I sit in a girly way.

Thank you for your comments and insight. I have been a CD for over 40 yrs and have come to both accept and enjoy fulfilling my inner need to dress.
I cannot describe the satisfaction I get when I finally am able to dress (mostly every night). I do like gender-bending when going out.... women's jeans, underwear, panty-hose. bra (with breast forms if the conditions are right) camisole or tank top under my denim shirt etc. .
I had abdominal surgery last year and now wear an ostomy pouch and found that wearing a high-waisted panty girdle really helps.
As for your comments about being outside, I can only say this... it is the act of going outside that expands our world beyond our "safe home environment" and cracks open the closet door, ever so slightly.
I would have a very hard time "passing" as I am 6'-2" and 200 lbs and have a moustache but have been told that I could be made up to be passable if was to shave.
My wife ( of over 32 yrs ) not only knows but buys me "gifts" and such.
I have no problem buying clothing, shoes, underwear etc. and quite often will go to stores alone to get these items. If a sales girl asks, I tell her they are for me and that I am one of millions of other guys who like to dress in private (or discreetly).
Today I bought two pairs of shoes at Pay Less they were obviously for me as they were a size 13 (my wife wears a 10) the girls at the counter were very nice and were joking and carrying on as though this was quite ordinary.
I watch what women are wearing very intently and do my best to emulate them as this is the look I am ultimately trying to achieve.
Once again thank you for your insight and perspective ,


Not so fun

I have not been able to share my experiences with an ex -lover. During our affair I discovered he enjoyed wearing my red nighties and I encouraged it. I began leaving them out for him when he came over after work. He was a prison guard and often stressed after work that is until he looked at the garments waiting for him. We began shopping together for his clothing....he was embarrassed, shy and afraid. I was in to this lifestyle for him. So turned on!!! He began sharing other things like his fascination for other men and I encouraged that as well. We enjoyed a rich fulfilling sex life but his overwhelming jealousy tore us apart. I grieved the loss of that relationship.

I'm new to this and thus haven't read much on this site, but my opinion is that I agree and like everything that you had to say. As I can only speak for myself, when I cross dress I want to fit in, which means dressing age appropriately and acting like a woman in my age group. I also take the time to ensure that details are correct, the jewelry matches, the make up is modest, but effective, and the footwear is for the season and outfit i'm wearing. So with that said, I would also prefer if those who feel the need to show their genitals while poorly dressed would save it for a **** site. For me it takes a lot time and effort to get made up, so i really enjoy seeing a well dressed gurl that put the effort into passing.

Well, I'm not so sure I agree with you about dressing "age appropriate." I'm not a crossdresser. I'm a transsexual living fulltime. I don't like the idea of being restricted to a certain style of clothing. If a woman wants to wear a miniskirt in her 80's she should be allowed. I think that would show a lot of courage to go against the so-called "norms." If it makes her happy why not?

Wow! your boyfriend/gurl is lucky to have your witness, support, and honesty.

I agree that crossdressing/transgender community is a continuum, with some who 'act out' in curious, even disturbing ways.

In my experience, the bonding of the common experience and dangers explains a loyalty that some would consider insane....kind of like putting up with a crazy uncle...but then that is family.

When I see those who 'act out', I look on with dread *and* compassion, and hope they find peace and contentment before they find a bad end....Then check my hair and make-up and say "there but for the grace of god go I."

Thanks for your words.

You have to be a strong woman to be able to accept your boyfriend that cross dresses. smiles***

What does strength have to do with her boyfriend's crossdressing? Maybe she enjoys it herself.

Thank you this is a good reminder and good advise. Everyone have fun!!!!!!

Thankyou for your replies
I have been in public in the past with enfemme ladies and found it fun but at the same time could see that they were nervious as you would expect, I think its a very brave thing to do and credit were its due to all that pluck up the courage and do it. i just thought id mention that should you take the plunge then if you look the part then youd be more excepted and enjoy it even more, Some people are strange and react badly to anything or anyone to them that is strange or different, I wear trousers but nothing is said to me, whats the difference? Iam sorry if I used the wrong terminology in my post. I totally beleive you that to go out in public is the last and greatest hurdle and to do ordinary everyday things like any other woman. Take a deep breath, dress appropriate and go do it, Id love to know how you get on.

Thanks for the advice my spouse knows of my fetish for pantyhose but I just don't know how to tell her I want to completely dress up as a female.

I know this post is old. I was wondering if you got around to telling your wife? I would say just come out and tell her.

Good advice. As for why I dress, well I am transgendered and I felt I was a girl and identified with girls since I can ever remember; probably about 4 or 5, though I didn't dress till I was about 6. As for going out, well it is a big world out there and I enjoy doing the same things as other women do.

I know this is old but I wanted to say first, the term is "transgender" not "transgendered" Just like you wouldn't say someone is gayed. Also, I feel like you think saying you are transgender means you are a transsexual. If that's the case you are wrong. Transgender is an umbrella tern which encompasses all people that deal with gender identity even crossdressers. So it would be correct if you were a crossdresser to say you are transgender as well as if you are a transsexual you still are transgender. I'm not being rude it's just that I am a transsexual and it bothers me that even some people in the community don't know the correct terminology.

If you're transgender or identify as more than one gender, then I think going out crossdressed when you are comfortable allows you to be happy because you are being true to yourself and others will feel more understanding of who you are.

I don't have a burning desire to pass or to go out enfemme, but I know many CD's do. I agree that dressing should be about fitting in when trying to go out. But I think that what happens is the opportunities to go out dressed are so few and far in between that the CD goes all out when they do get a chance to go out. That's when the ultra tight mini and high heels come out; even to the grocery store etc.

I understand what you are trying to say but the CD that goes out in public needs to understand that if they don't blend in then it could become a safety issue.

Indeed. I also think there's a thing happening where we try to project what we feel is the embodiment of ultra femininity in those opportunities to go out. That's where great friends/girlfriends come in. Help your CD tamp it down.

My wife does a great job of keeping me grounded when I haven't been able to dress. We go on a trip and my first instinct is to bring everything, lol. Wifey helps me realize I can't wear it all in 2 days so pick a few.

Wise advice! I don't go out, but frankly getting dressed up makes one want to be seen. Really it's that simple, weird, I know but true.

I don't understand. You said you don't go out but yet you are a crossdresser and you say getting dressed up makes on want to be seen. So how come you don't want to be seen?

Well since I posted that Lori I've been out and been seen. I came out to my wife in February, she is still with me and we are working though this. Not easy. I'm also on hormones with an endocrinologist.

That's great you are progressing!