Post
This experience may contain mature content, as flagged by the community. Please click away if you do not want to see this content, or if you are not of age. To report inappropriate content, please email us.

I Love Wearing A Bra As A Man

Personal Stories, Advice, and Support 444 People

    I Would Love To Wear One Everyday!

    As you can see, I'm a natural 36C and it would be fun to wear one everyday, like a lot of guy do on EP.Just under a t shirt going shopping or to work would be "Heaven!"I am a closet crossdresser and married.....so I wear one, when I can.
    CandyKowal CandyKowal 46-50, T 6 Responses Sep 21, 2011

    Your Response

    Cancel

    Sheer

    I remember how hard I was even before she instructed me to raise my arms and, far above my head, to any observer I had clearly surrendered. the cups, placed up against my chest by her curious hands, made me throb all the harder. "you're such an adorable little feminie doll you...
    zoecrosswater zoecrosswater 31-35 1 Response Jul 20, 2011

    Your Response

    Cancel

    My Chistmas Bra

    Was going though my bra collection, must have about 25 in the bra drawer. Found a red velvet Maidenform 36A bra. Kind of a Christmas theme.   No silicon inserts, all me!
    deleted deleted 26-30 1 Response Dec 22, 2011

    Your Response

    Cancel

    Wear A Bra

    I wore my first Bra when I was about 23/24 after just wearing pantyhose/tights under from about 13/14 my trousers when ever I got the chance and found that I quite liked wearing bras along with my pantyhose/tights and after another couple of months I decided to see what I felt...
    xdpaul xdpaul 56-60, M 1 Response Jun 8, 2012

    Your Response

    Cancel

    Wearing Bras

    I really love wearing bras. They are so sexy and feminine. I started wearing my mom's bra and when her bra no longer fit me, I bought my own bras. It's such a great feeling wearing a bra feeling the band around my chest and the straps on my shoulders. And I love to have a bra...
    jml2000 jml2000 56-60, M 1 Response May 22, 2012

    Your Response

    Cancel

    Want My **** Sucked While Wearing Bra

    The bigger my moobs get the more I love them! They feel so good in my tight bras and I love the feel to rub my nipples till they're hard and stand out in the bra. I too love the feeling to squeeze and cup my moobs and think how great it feels to have my nipples sucked till they...
    robbi95 robbi95 46-50, M 1 Response Jul 16, 2011

    Your Response

    Cancel

    Since Starting To Crossdress Have Worn A Bra

    After first purchase and wearing women's panties the next item of female lingerie was a bra. Additional items purchased and wear are garter belts, nylons and slips. At Walmart the other day in the main isle there was a hanger tree filled with bras marked $3.00 each. I found one...
    deleted deleted 26-30 1 Response Sep 23, 2011

    Your Response

    Cancel

    Airport Security And Bras

    I don't know what got over me, what made me put on my bra as I was getting changed for my overseas trip. I did some background reading and it turns out that TSA officers are actually quite professional and will not cause any grief for bra wearing men. This kept me calm as I...
    val83 val83 26-30, T 1 Response Sep 27, 2013

    Your Response

    Cancel

    The Feeling Of My Bra

    At night before going to bed, I set out 5 or 6 different color bras along wih a top, a cami, a panty, and a pant or skirt. I get up in the morning and I pick out a bra and get dressed. My panty first then my plunge bra. I hook the back and slowly slide up the shoulder straps...
    serinalynn serinalynn 61-65, M Dec 7, 2011

    Your Response

    Cancel

    Bra On Everyday.

    After years of using hormones I have lovely B cup boobs! I have no choice really but to have to wear a bra but I love it. Its just a daily naturel thing now to wear one. I dont get any 'kicks' out of it, its just normal for me to wear one. Most of the time I forget I got a bra on...
    gurlyruth gurlyruth 46-50 Jan 23, 2013

    Your Response

    Cancel

    But Only Sometimes

    Most of the time just wearing panties is enough for me. Not counting the male thongs of swimsuit material I only have panties for underwear. I wear them or nothing, and mostly it's NOT nothing. But the bra is a different thing. I need to be in the mood (or ordered by my Mistress...
    MPsslavetommy MPsslavetommy 70+, M Sep 6, 2010

    Your Response

    Cancel

    Everyday!!!!

    I wear a bra everyday. I love the way it makes me feel. Sometimes I forget that I am wearing one. I wear a different one everyday. I am small busted so my bra in not noticable when I wear a male shirt over it.
    davis36a davis36a 61-65 3 Responses Oct 15, 2010

    Your Response

    Cancel

    Well, Maybe Not Exactly As A Man

    Because by the time I get my bra and panties on, I'm well on the way to being a different person. At least in my mind. I'm not a man anymore, but I become Rayanne. But I love wearing a bra, because I love to crossdress and become Rayanne. In the past, I've always worn a 42C or D...
    RayanneA RayanneA 56-60, M 2 Responses May 2, 2012

    Your Response

    Cancel

    How I Got 38c Boobs

    LET ME START MY STORY BY SAYING IVE ALWAYS WANTED BREASTS THAT WOULD FILL A BRA DURING PUBERTY I HAD BREASTS THAT WERE LARGE WITH AUREOLES THAT WERE SO LARGE I WAS EMBARRASSED TAKE MY SHIRT OFF. IT WAS AROUND THIS TIME THAT I TRY ED IN MY MOTHERS LONG LINE  BRA I DIDN'T FILL...
    HIPPILOTTA HIPPILOTTA 66-70, T 3 Responses Nov 3, 2010

    Your Response

    Cancel

    Love To Wear A Bra

    i love top wear a bra, i love to know my starps are visiable and i love how my straps sit on my shoulders, i also love how they wrap around me
    addguy3455 addguy3455 18-21, M Oct 14, 2011

    Your Response

    Cancel

    Going Out Secretly

    Like a lot of males who love to cross dress there is no way I am passable. Yet I also love to wear my wonderful female clothing other than in the secrecy of my home. So I do what is often referred to as "dressing under", that is wearing as much female clothing as I can under my...
    deleted deleted 26-30 3 Responses Nov 1, 2010

    Your Response

    Cancel

    My Bras Are My Love

    i have quite a few bras now ,at least 20 different ones in many colors ,,but my favorite one is an old early purchase ,a cheap bra from a bargain clothes store,it is a size 42d that has been stretched loads to fit ,,it used to be dead tight ,but made my boobs stand out loads like...
    franceslepole57 franceslepole57 56-60, T Nov 2, 2012

    Your Response

    Cancel

    Great Website

    Cool Aussie site www.hommemystere.au have a look
    pantylover5099 pantylover5099 36-40, M 2 Responses Mar 9, 2012

    Your Response

    Cancel

    Love To Fill A Bra With My Moobs

    I love the feel of tight panties and bras and lingerie and dressing up around the house. Not passable as gurl to go public so i don't. but do wear panties, hose, bras, and lingerie under my levies to go shopping. Love the feel and thought of what the person next to me would think...
    robbi95 robbi95 46-50, M 3 Responses Oct 16, 2010

    Your Response

    Cancel

    Related Experiences

    So guys and girls I am needing some help.I am wanting to pic has my first pair of thongs.Any suggestions on brand,fabric,any bigger size,etc.I love wearing panties and I think...
    Bigboylovinpanties Bigboylovinpanties 18-21, M 1 Response Jul 23

    Your Response

    Cancel
      So I'm a guy....and I am love wearing short shorts....I can't stand the styles they have today down at the knees....I like them mid thigh or shorter. I honestly haven't...
    ilovethongs23 ilovethongs23 41-45 4 Responses Aug 10

    Your Response

    Cancel
    It took me a long time to accept this but I love watching a man reach his highest level of excitement. It's a complete pleasure for me to see this and see his body giving him the...
    ILoveAGirlInStockings ILoveAGirlInStockings 51-55, M 2 Responses Aug 10

    Your Response

    Cancel
    I love wearing thongs so boys will see my thong and I wear my thong with a pair of low rise jeans and I like my but crack and thong is showing
    lauran2014 lauran2014 16-17, F 3 Responses Jul 21

    Your Response

    Cancel
    I love wearing women's clothes. I just feel so right. The problem is that my body type doesn't fit this obsession. I seriously sometimes feel like I should be a girl.
    c455muscle c455muscle 22-25, M 10 Responses Jul 24

    Your Response

    Cancel
    I love wearing make up!!! I feel better with make up on
    andreaespe andreaespe 18-21, F Jul 27

    Your Response

    Cancel
    When I was young the miniskirt was all the rage and we loved wearing them. We used to get into trouble at school if our skirts were too short but mum was very good about our desire...
    Jilly53 Jilly53 56-60, F 1 Response Jul 31

    Your Response

    Cancel
    I love wearing granny panties the big pink ones are my fav
    Benbrian Benbrian 13-15, M 3 Responses Aug 5

    Your Response

    Cancel
    I love wearing all kinds of lingerie, and I especially like the kind that makes me feel like a sissy. I made this video when I was feeling a little sissyish. I hope you like it...
    VictoriaFredericks VictoriaFredericks 36-40, M 3 Responses Aug 12

    Your Response

    Cancel
    When I was a teenager I loved wearing miniskirts. In fact I used to wear them as much as possible in preference to jeans, etc. to show off my legs. My mum used to let us wear...
    Jilly53 Jilly53 56-60, F 1 Response 5 days ago

    Your Response

    Cancel
    i love wearing my wifes clothing and going out for a drive in the car and maybe a walk
    funlover74 funlover74 36-40, M 4 Responses 3 days ago

    Your Response

    Cancel
    I love wearing low-rise jeans or shorts with a low cut tank top that show off my belly and cleavage ;-)
    SexyBellyButton80 SexyBellyButton80 31-35, F 6 Responses 3 days ago

    Your Response

    Cancel
    I am in love with a man I never met it's hard to know that yeah he loves me but not in that way I'll never get to meet him I'll never get to see his gorgeous brown eyes...
    xriiccii xriiccii 13-15, F 2 Responses Jul 26

    Your Response

    Cancel
    I don't know much people who like it... Then again I don't know much people! But I totally love anime and manga, everything about it is just awesome. It makes me want to jump up...
    farahway farahway 16-17, F 23 Responses Aug 1

    Your Response

    Cancel
    This is the first time I fall in love with younger man. He's 29 and I'm 37 :D
    lilithadam lilithadam 31-35, F Aug 11

    Your Response

    Cancel
    I come on here and can express myself freely and it usually feels good.... But Damn I love being a MAN and all that goes with it. Macho **** and all...
    JimD911 JimD911 36-40, M 1 Response 5 days ago

    Your Response

    Cancel
    I think I do..... For about a year or so, with the exception of my school uniform, that's all I've worn.... I'm so used to them now that it feels strange not wearing one...
    SarahTheHooker SarahTheHooker 18-21, F 1 hr ago

    Your Response

    Cancel
    I love thongs (girls ones) and wear norhing else
    ryaninthongs ryaninthongs 22-25, M 4 hrs ago

    Your Response

    Cancel
    I brought my first bra and suspenders set yesterday along with a sports bra and a Calvin cline top, and a pair of size 8 woman's jeans that are probably a size too small, I love...
    Incideofme Incideofme 36-40, M 8 Responses Jul 29

    Your Response

    Cancel
    Almost all of my female attire is second hand! I go to Garage sales a great deal. I have purchased; second hand panties, bras, slips, pantyhose, skirts, blouses dresses, and...
    OhioSissy OhioSissy 51-55, M 3 Responses Jul 23

    Your Response

    Cancel
    I don't know why. It's probably cause I'm just used to buying that brand. Plus it's convenient when you want to dance, in my opinion. Damn if there was a possibility That I would...
    FunnyandNerdy FunnyandNerdy 16-17, F 1 Response Jul 20

    Your Response

    Cancel
    I'm wearing purple bikini style panties, black and white yoga shorts, cheetah bra, and a black tank top to bed 😏😍
    sammixdress sammixdress 18-21, M 5 Responses Jul 27

    Your Response

    Cancel
    I am in love with all kinds of lace and frills, I wish I could have them all and bras to match but with 32GG boobies I have to special order my bras which are to expensive to...
    MissABell MissABell 18-21, F 12 Responses Jul 29

    Your Response

    Cancel
    Today I'm wearing underwear that belonged to my friends girlfriend . Grey cotton g string white bra . They feel so good and just the thought that she had them on drives me insane...
    toesforme toesforme 36-40, M 6 Responses Aug 12

    Your Response

    Cancel
    My wife has me wearing matching satin Cacique bra and panties with black nylons, black flirty skirt, red top and my red 4" heels. Also all made up with a my brown curly wig and...
    nikkifemmdslave2 nikkifemmdslave2 36-40, M 4 Responses a week ago

    Your Response

    Cancel
    I'm standing in the line at walmart buying my first pair of bras. I have really no clue what size I am but I'll figure that out
    thestifmeister thestifmeister 22-25, M Aug 3

    Your Response

    Cancel
    i get these crazy feminine urges all the time and the only way to satisfy them is to dress in female lingerie. Now, I am still a guy and, like most guys, am generally lazy and I...
    DonnaSue10 DonnaSue10 66-70, M 11 Responses Jul 23

    Your Response

    Cancel
    I have several pairs of bras and panties, and love getting dressed up
    asspussypowerbottom asspussypowerbottom 26-30, M 6 Responses Jul 24

    Your Response

    Cancel
    Those corsets that cinch tight, showing off your curves and leaving your bottom exposed in scantily clad panties. There’s the leather with buckles on the sides and holsters for...
    MissMasque MissMasque 13-15, F 3 Responses Jul 29

    Your Response

    Cancel
    I have worn lingerie for years. I started when I was in my early teens. Like most men who wear and start early, it was my mothers stuff that I found first. Things like stockings...
    Fullofstars Fullofstars 31-35, M 4 Responses Aug 3

    Your Response

    Cancel