Crossdressing who's into it?

[Maxxine]

Hi. Not long ago I have discovered that I love crossdressing. Can't do it at home but enjoy it when I am with a guy. And I mean full on makeup, wigs, tits, etc and not just a pair of panties. I find that becoming or feeling as a female helps me in many ways feel more comfortable sucking dick, getting fucked, etc. I think the experience becomes much more erotic and sensual. Once in a while I do play with a guy that enjoys me in full makeup etc. He loves it! I enjoy imagining I am a girl on my knees servicing his cock and giving him pleasure. As I bob up and down on his cock the hair of my wig gets in the way which often I need to pull it behind my ears and love that too! I love how awkward it is to walk and kneel on high heels. Love wearing garter belts, stockings and all of that. You get the idea. But this is all relatively new to me and I am trying to embrace it! FWIW public facing I am completely "normal/straight" and masculine.

I want to ask who's into it? What is your experience. What do you like to wear and why does crossdressing do it for you?

[SAW1969]

I wore my 1st Wife's 1 piece dresses when she wasn't around. Total turn on. I've been really interested in cross dressing lately. If I wasn't married I'd would be in a relationship with a guy and would want him to turn me into a sissy in private of the home.

[biguycancun]

Not to repeat myself, but for several years I worked in the sex trade as a tranny escort, which involved the whole deal, including grooming and makeup. I loved the lingerie, shoes and clothing. At 6'1" my "clients" knew I was a man, but I was very passable and that was what they were paying for. And the obvious role of the bottom was very exciting. I loved being on my knees with the guy standing over me, his cock in my mouth with me looking up, encouraging him to cum in my mouth. Even just making out on the couch with him feeling me up and sliding his finger in and out of my ass would get me up to the edge, and my orgasms, when they came, were much more feminine in terms of body response as opposed to the usual squirting of semen. Shivering and shaking and moaning, when they happened, were wonderful to experience and usually resulted in an increased gratuity too.

Now, several decades later I can't pass, but I'm fortunate to have an FWB who dresses and enjoys me dressed too. I can still walk well in stiletto heels and one of my favorites is standing in heels and stockings while she (he) feels me up from behind, kissing my neck, loosening my bra and then fucking me from behind while squeezing my tits. It's amazing what your mind can do to make you happy.

[Maxxine]

I wore my 1st Wife's 1 piece dresses when she wasn't around. Total turn on. I've been really interested in cross dressing lately. If I wasn't married I'd would be in a relationship with a guy and would want him to turn me into a sissy in private of the home.


Do you ever crossdress when you play with a guy or just privately for your own enjoyment?

[Maxxine]

Not to repeat myself, but for several years I worked in the sex trade as a tranny escort, which involved the whole deal, including grooming and makeup. I loved the lingerie, shoes and clothing. At 6'1" my "clients" knew I was a man, but I was very passable and that was what they were paying for. And the obvious role of the bottom was very exciting. I loved being on my knees with the guy standing over me, his cock in my mouth with me looking up, encouraging him to cum in my mouth. Even just making out on the couch with him feeling me up and sliding his finger in and out of my ass would get me up to the edge, and my orgasms, when they came, were much more feminine in terms of body response as opposed to the usual squirting of semen. Shivering and shaking and moaning, when they happened, were wonderful to experience and usually resulted in an increased gratuity too.

Now, several decades later I can't pass, but I'm fortunate to have an FWB who dresses and enjoys me dressed too. I can still walk well in stiletto heels and one of my favorites is standing in heels and stockings while she (he) feels me up from behind, kissing my neck, loosening my bra and then fucking me from behind while squeezing my tits. It's amazing what your mind can do to make you happy.


Thank you for sharing. Yes, the brain is the most sexual organ that we have! When I crossdress, I am someone else. I get transported and almost acquire a different identity. Not sure if this is true for everyone?

[Maxxine]

I should also mention that this thread is not only for those that enjoy being a CD but also those that enjoy being with a CD.

[19biman61]

When I was in high school I would dress in my mother's garments when I was home alone. I would wear her stockings, girdle, bra and wig. Never did do make-up. After I got married I would wear my wife's stuff when I was home alone. After we got divorced I bought some of my own lingere' along with a few dresses, skirts and blouses. One time I went to the local adult bookstore dressed in corset, panties and thigh high stockings. I wore a sweatshirt and sweatpants over everything for the drive there. I removed the sweat clothes in my car and went inside. even though I don't pass I still got a lot of attention.

[freakyretro69]

Being an alpha male, this is something I desire. There are some beautiful crossdressers out there that really turn me on. Unfortunately, availability in my area is nonexistent so, I believe this will be an unrealized fantasy. The look of a sexy fem dressed sexy in womans clothes would push me to cross the line.....

[chongster]

I have a hot CD friend that I hook up with. She (he) says I make her feel like a real woman when we are together. I love a young sexy girl with a dick, she is in her 30s. I think it's harder to pull off when you get older.

[monaohio]

i would love to have a breast form body suit with big boobs and have on a sexy see through naughty nightie on or have nothing on and boobs bouncing i love being a woman even through i am a man

[SAW1969]

Do you ever crossdress when you play with a guy or just privately for your own enjoyment?

I was wearing my 1st wife's dresses at home while she was away. I would just jerk off alone. I have never been with anyone when I was wearing her clothes. That was roughly 25 year ago. I haven't worn any women's clothes since, but the urge is coming back and I want to play with a guy while wearing women's clothes etc...

[Maxxine]

I have a hot CD friend that I hook up with. She (he) says I make her feel like a real woman when we are together. I love a young sexy girl with a dick, she is in her 30s. I think it's harder to pull off when you get older.


That's how my FWB makes me feel. I am not exactly young anymore but I still make for a good CD. Better now while I still can LOL!

[Maxxine]

i would love to have a breast form body suit with big boobs and have on a sexy see through naughty nightie on or have nothing on and boobs bouncing i love being a woman even through i am a man


I am not very hairy at all. But the little I have I wish I could shave it off completely. I think it would further enhance the experience. Being married I unfortunately can't quite go there.

[monaohio]

same here with me

[monaohio]

I am not very hairy at all. But the little I have I wish I could shave it off completely. I think it would further enhance the experience. Being married I unfortunately can't quite go there.
same here with me i am married wife does not know

[BiVers240]

I am definitely NOT into the whole panty wearing thing. When I am in the mood for a woman, I want a pussy. When i am in the mood for cock, I want a masculine man.

[Maxxine]

I am definitely NOT into the whole panty wearing thing. When I am in the mood for a woman, I want a pussy. When i am in the mood for cock, I want a masculine man.


Makes perfect sense. Definitely not for everyone.

[cumagain68]

I have panties, blouses and skirts, both long and short. I wear them at home inside, unfortunately, I
would look like a very ugly woman.
However, I like the skirts for the comfort and freedom they afford me, and even if I wear nothing else
at the time, I will put on the skirt, just to have it on.
I don't think of it as crossdressing, it's just getting comfortable. I rarely wear anything else than
the skirt. When I feel like it, I will go the whole nine yards. Almost bought a bra with inserts in
case someone with a big one wanted, it but have been too short on cash lately. (Also short on friends
with big ones.)

[dbaker]

I’ve been cross dressing since my mid twenties and was very passable in those days, now days not so passable but still sexy with the lights down low. I like to fully dress even doing my nails and make up too.
For me it’s almost a mental transformation when I pull up a pair of thigh high stockings and feel them on my skin, and my breast forms really take me to a higher level of cross dressing.
I dress up for my lover as often as I get the chance to and love having him on top of me with my arms and legs wrapped around him as he makes love to me, I love that feminine feeling of having a man inside me and I usually cum every time I feel his cock begin to pulse as he is cumming inside me.
I like giving blowjobs but it’s so much better when I’m dressed and have my wig pulled to the side so he can see my lips wrapped around his cock, a couple times I have even came while sucking, it usually happens when I’m holding his cock deep in my mouth moaning with pleasure, as soon as he begins to cum in my mouth the feeling of being a girl makes me cum without touching my cock.
So ya, I’m into cross dressing and I’m a pretty hot fuck too ��

[bsquaredville]

-raises hand-

i enjoy it. I just wish I looked better in it than I do.
I used to be able to try my ex wife’s clothes on when I worked nights and she worked days. I’d get dressed up in her panties and some leggings and a cute bra. Then I’d try on cute tops but my favorite were dresses. I wanted to feel as girlie as possible. I always said I was going to take a nap while being dolled up but I’d usually end up masturbating and cum and then feel uncomfortable how tight everything was lol

[DLazguy]

I'm not into cross dressing, but if I could find 1 guy or a group of guys who were into it and who were good looking and very HUNG (9+ inches and very thick), I'd dress up for them. There would be a few requirements;

1 - attractive (face and body).
2 - their cocks would HAVE to be 9 inches or longer and very thick.
3 - No hard drugs (alcohol and weed only).
4 - ZERO diseases.
5 - taking video of me sucking and getting fucked is a must

Our meeting would not be a quick cum and go. If it is one guy, I would take my time sucking and draining his balls. I would let him recover so he can take his time fucking me before he fills my ass with his second load.

If it is with a group, I want to be surrounded by rocks (1 in each hand, 1 in my mouth, and 1 fucking me). I'd start off sucking each of them before each one took their time fucking and filling me with their loads. I want video of their socks stretching my mouth and ass. I want to be able to feel how good I was tucked all week. When I walk or sit i want feel how much my ass was stretched and pounded.

[Pat69]

Wearing Bras, Pants, Dresses, and the sort of female clothing is a real turn-on. It opens the mind to another aspect of being a human being. It makes me feel sexy and really feminine. If I put on panties I get so wet and excited - what's with that? I don't know but I want to suck a good cock while I'm in that moment. I love feeling, sucking, fucking cock anyways. I don't know what took so long for me to realize I'm probably Gay as much as I am Bi.

You can dislike a guy cause he is a male, but you don't have stop loving cock.

It's all good!

[Maxxine]

The only down side for me when it comes to crossdressing is how much work it takes as I like to pretty much dress from top to bottom with makeup and all. My FWB knows that I need at least 45 mins. I sneak into his bathroom to get ready and I refuse to let him see me otherwise. I like to get my makeup as perfect as I can which I find is not always so easy.

[monaohio]

The only down side for me when it comes to crossdressing is how much work it takes as I like to pretty much dress from top to bottom with makeup and all. My FWB knows that I need at least 45 mins. I sneak into his bathroom to get ready and I refuse to let him see me otherwise. I like to get my makeup as perfect as I can which I find is not always so easy. what need is a woman to put on and show me how to put make up on with me in just a breast form body suit and a long hair blond wig with clip on ear rings

[MNBiGuy]

I am personally, privately just getting into this. On a very limited basis. Most of the men I get with don’t like this so it’s more for me. I have always had a foot/shoe fedish. I get it. I’m weird. But I order from Enfemmestyle.com. And I love their stuff!!their shoes and clothing are very well made!

[SAW1969]

I've been looking at sexy lingerie, wigs, breast plates etc... so horny now! My wife caught me watching a video on how to do make up last night. She says to me does that turn you on? She doesn't approve of bi/homo activities.

[Huey1N]

I like the feeling of pantyhose. I haven't had the pleasure yet, but the idea of being fucked while wearing them is a turn on. Also I just like the way they feel against my hard on.

[MIGHTTRY1]

I like wearing panties and lingerie sometimes while jerking off. Makes my cock hard thinking about it.

[Maxxine]

I am personally, privately just getting into this. On a very limited basis. Most of the men I get with don’t like this so it’s more for me. I have always had a foot/shoe fedish. I get it. I’m weird. But I order from Enfemmestyle.com. And I love their stuff!!their shoes and clothing are very well made!


Good to know. I have been looking on that site and I like a lot of their stuff.

[Seamlesssensation]

I like the feeling of pantyhose. I haven't had the pleasure yet, but the idea of being fucked while wearing them is a turn on. Also I just like the way they feel against my hard on.
Same here, love the feeling of a nice high quality pair of pantyhose. Would love to be bent over while wearing them as well.

[monaohio]

Same here, love the feeling of a nice high quality pair of pantyhose. Would love to be bent over while wearing them as well. then buy a couple pairs of crotchless pantie hose

[curiousguy1959]

I'm very much into it. I started with just wearing a basic thong (felt very silly that first time) and gradually progressed to dresses, heels etc. I only dress at home and my wife doesn't know. That severely limits my opportunities to dress. I really love the feeling of freedom (and self conscious when wearing a shorter skirt and and wondering how women feel when they wear something like that and be self conscious all the time in public places) and feel sexy, although i am not in any way convincing. Just thinking of dressing makes me horny. I am not into male virtual partners, a male as a male is not in any way attractive to me as I need something femme, even if it's only wearing panties (that is hot anyway). Too bad there are so few webcam communities, because I would to cam with likeminded dressers.

[licyou69]

I don't fully CD, but I do enjoy wearing panties. Slipping on panties before giving my mouth or ass to a man makes me feel feminine.

[biguycancun]

I don't fully CD, but I do enjoy wearing panties. Slipping on panties before giving my mouth or ass to a man makes me feel feminine.
You should add stockings to your play time. Then maybe heels. Each addition enhances that feminine feeling.

[Footstep40]

I was living with my boyfriend at the time in the early 2000's. We were enjoying some post coital glow, and he asked me if I had ever experimented in cross dressing. I really hadn't at that point, beyond playing Dr. Frankenfurter in my college's production of Rocky Horror, but I told him I was open to trying, could be fun. I forgot about our conversation as I was barely awake at the time.
Our work schedules were odd at that time, I'd get up early, leave, and he would be about 4 hours later, and at night I'd be back early, he'd roll in about 4 hours later. A couple of days later I came home to find a little bag laying on our bed, I opened it up and it was a black teddy, which is about like a woman's one piece swimsuit. I called him up, asked him about it, he said it was a gift for me, and him. Ohhh got it. I put it on, it wasn't as uncomfortable as the costume I wore for the play was, quite opposite really. I felt a little excited, like I was doing something a little taboo, I checked myself out in the mirror, I wasn't turned on by seeing my hairless body, trying to fill out something that wasn't made for me, but, it was what it was. I waited for Nick to come home and greeted him at the door, the look on his face was worth every second of my thinking I looked weird to me. I like my men, rugged, and masculine, but Nick, didn't. We had some amazing love making that night, didn't even make dinner.

Every few weeks or so, I'd come home from work to another surprise, or I'd buy a piece of lingerie for our exploits, some were very comfortable, some of them were like trying to figure out a puzzle and a little painful, squished bits isn't fun. Those usually didn't get moving into the rotation. I had a co-worker that told me that she would sometimes greet her boyfriend home from work in front of the door on her knees dressed in something sexy, or nothing, I started doing that and Nick had a look on his face like he won the lottery, I still do this one for my husband, although now I need a pillow for my knees.

Nick and I eventually broke up and I ended up blindly throwing them in a box, the ones in the laundry were left behind. I would get some out to wear as they were just so comfy, and made me feel attractive when that's not the case after a break up. Sometimes, I'd wear them for some of the men that visited my bed. When I married my ex wife, I put them in a plastic container and put them in our storage unit, or up in the garage attic. After our divorce I grabbed a bunch of items out of storage and had totally forgotten about them, washed them up and put them in a drawer. I dressed up for a few guys here and there, they enjoyed it. When my now husband moved in with me, he had no idea until he was making space in a drawer for his things. He thought at first that they were something the ex left behind, I showed him that they weren't, some were a little tighter than they used to be, but that's ok, it gets Darryl going.

I have been expanding what and when I wear women's clothing beyond lingerie. I wore a very nice, simple silk and short white dress, had a bit of makeup, jewelry, and my hair was perfect when we got married in October, I felt like myself, and my husband loved it, the only odd part of that day was that I was wearing white. I've worn a dress to a work event I had, around the house, out to dinner, and on our 2 week honeymoon in Zipolite, I only brought two sets of "men's clothing" for travel days, out hotel was nude, as was the beach, so really a little linen summer dress, or cover was all that was needed most of the time. Am I passing? Probably not 100%, but nobody cared there at all, I got asked where I got a dress I was wearing, The one night we needed to dress up a little, the outfit that I had on was killer, split to the hip on both sides, and backless, my ass looked great!
I got groped, a few drinks and more than a few offers.


I have found that leaning into dressing this way helps my husband and I with the roles that we have in our marriage, he calls me his wife, and I love that, not to mention that it adds a little fun and excitement to our sex life. I've honestly never felt so comfortable in my own skin in a long time.

[Kappsguy]

I tried dressing when I was a young man, I liked the feel if the soft clothes on my skin. But that was a long time ago.
However, I do like, I prefer, any male partners I play around with to wear some sexy woman's clothes. I convinced several to try it for the first time. If they can't buy or keep the clothes, ill buy them something I like and have them dress up for me. Then I stash it for their next visit.

[Seamlesssensation]

then buy a couple pairs of crotchless pantie hose

Well sure but you need more than just the crotchless panty hose to fullfill that fantasy….. The play partner to bend you over seems to be the unicorn.

[BiGuyinMA]

I've been a crossdresser since my early 30's when I used to wear my (then) wife's lingerie when she was out. Totally not passable as there was no wigs/makeup involved.
Gave it a break for a few years but then submitted to my urges again in my mid 40's. Like most gurls, started off with just panties, limited lingerie etc but over the next few years dived in deeper and deeper. Now, when given the opportunity I dress fully, wig to heels, makeup and everything in between. I don't just want to wear lingerie, I want to top it off with nice skirts, blouses, dresses etc. I've learned to dress appropriately for my age now (60 but very slim and toned, totally hairless) and strive for a kind of mature businesswomen type of look.

When I dress fully I'm dressing to get fucked... When I hookup with a guy, I want him to see a somewhat sophisticated women when I open my hotel room door, and I want him to have the pleasure of slowly undressing me down to my lingerie as a prelude to sex.

I would consider myself somewhat semi-passable if I get everything right and guys appreciate that and are nearly always willing to overlook my shortcomings. They're in search of a fantasy and that's what I try and give them.

I'm always upfront about what I'm looking for... I'm the women and he's the man, he's there to fuck me and never the other way around, but if I've done my job right there's normally not much in doubt and we both get what we want.

[MIGHTTRY1]

When I was getting divorced, there was no way I was going to let my ex-wife take the lingerie I paid for to fuck other guys. So I took it knowing I?d be wearing it sometime!

[Cforme]

I love crossdressers! To me it’s sexy as hell! Making out with someone in full drag with makeup, lingerie, stockings, everything, is hot! The thought of a cock being hidden under all that and either sucking or fucking in full dress is an ultimate turn on for me.

[redngoldpride]

Hi. Not long ago I have discovered that I love crossdressing. Can't do it at home but enjoy it when I am with a guy. And I mean full on makeup, wigs, tits, etc and not just a pair of panties. I find that becoming or feeling as a female helps me in many ways feel more comfortable sucking dick, getting fucked, etc. I think the experience becomes much more erotic and sensual. Once in a while I do play with a guy that enjoys me in full makeup etc. He loves it! I enjoy imagining I am a girl on my knees servicing his cock and giving him pleasure. As I bob up and down on his cock the hair of my wig gets in the way which often I need to pull it behind my ears and love that too! I love how awkward it is to walk and kneel on high heels. Love wearing garter belts, stockings and all of that. You get the idea. But this is all relatively new to me and I am trying to embrace it! FWIW public facing I am completely "normal/straight" and masculine.

I want to ask who's into it? What is your experience. What do you like to wear and why does crossdressing do it for you?

I prefer this type of girl whether they do it full time , part time , in secret married or single .I love the whole experience of someone being able to be who they are truely . Letting the true person out to be who they really are with someone who not only loves it but wants to share it to the fullest.

[SilkyHoseLover]

*Snip* I'm fortunate to have an FWB who dresses and enjoys me dressed too. I can still walk well in stiletto heels and one of my favorites is standing in heels and stockings while she (he) feels me up from behind, kissing my neck, loosening my bra and then fucking me from behind while squeezing my tits. It's amazing what your mind can do to make you happy.

Amen - that's a favorite scenario of mine, too! I have a shaved chest and smallish tits that are very soft, with nipples that get very erect when I play. I love everything about assuming traditional feminine roles - the psychology involved is off-the-charts!

[SilkyHoseLover]

*Snip* ... the idea of being fucked while wearing them is a turn on.
The reality of it is even hotter! Once you've been there, you'll want to return many times. :bigrin: