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I Crossdressing Swimwear

Personal Stories, Advice, and Support 632 People

    At The Beach

    The first time I went out in public as a woman in a bikini was a few years back. Some of my gay male friends were having a catered party at the public nude beach and I was invited. I bought a yellow bikini, tucked myself back severely, and went. The beach is clothing optional so...
    deleted deleted 26-30 1 Response Aug 8, 2012

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    My First Bikini!

    O wow so I'm not alone? for years now I have enjoyed wearing women's bikinis or swimsuits it all started for me many years ago now when I was about 14 and just getting very sexual aware! My mum had a big clear out of her cloths around this time and in these cloths was a Navy Blue...
    deleted deleted 26-30 4 Responses Sep 30, 2011

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    First Time As A Beach Babe

    I had been looking for ways to push the boundaries of my transvestic fetish and decided to wear a bikini to the beach. Living in Australia there are so many empty beaches, but I had one in mind. It was going to be a bit of a drive, but I knew I'd have it to myself, especially...
    territgirl territgirl 51-55, T 7 Responses Nov 24, 2012

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    My First Ladies Bathing Suit

    My first swim suit was red,yellow and blue. It was a one piece given to me by my wife. She had bought a new swim suit and asked me if I wanted it. I didn't even hesitate and grabbed it from her. I loved to wear different colours and styles of tights and pantyhose with it. I think...
    gdmidd gdmidd 41-45 2 Responses Oct 6, 2011

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    Wearing Female Onepiece Swimwear.

    I see no problems in wearing onepiece swimwear at all, I am a male and I also identify myself as a man who wears female onepiece swimwear, I wear them because I find the men's swimwear very, very booring, I do it for several reasons and one of them is because I have a scar on my...
    markwhiting markwhiting 41-45, M 4 Responses Apr 1, 2012

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    A Replacement Suit

    Well I did it I went to a Goodwill store and found 2 ladies I piece bathing suits. Of course I had to try them on. One was multiple colored that had a zipper between the breasts but not a very high cut leg, the second was light blue kind of a teal colour open back that tied up...
    gdmidd gdmidd 41-45 1 Response Oct 14, 2011

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    I Love Bikini Tan Lines

    Now that the summer is here. I have been working on my bikini tan. I love painting my toe nails and going to the beach. There is enough room on the beach that I don't have to worry about someone sitting next to me. I'll tuck my **** back in my thin skimpy string bikini bottom...
    jaqui928 jaqui928 51-55 4 Responses Aug 7, 2013

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    Sun Bathing In The Woods

    When I was in my mid 20's I took my vacation in the south central mountains of New Mexico. I had found a place to camp in what could be described as a cove. After I set up camp and ate breakfeast the sun was shining done and felt good. I decide I would sun bath since I was in a...
    Jambell Jambell 51-55, T 2 Responses Feb 1, 2011

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    I Can't Believe I Did It.

    In the last month some of the hypnosis I have been doing to help me with my transition to living as a woman seems to be paying off. There is on I listen to regularly that seems to be in regards to wearing women's with out caring if others know or say anything. This past week I...
    deleted deleted 26-30 2 Responses Jun 12, 2012

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    With My Gf

    Me and my gf decided to go swimming down the beach the other day. As I was looking through my wardrobe for some swimshorts, my gf reached in around me and dug out my blue spotty swimdress and said that I should wear that. We got to the beach and she ******** down to her bikini...
    pantylover5099 pantylover5099 36-40, M 4 Responses Jun 6, 2011

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    My First Public Crossdressed Swimwear Experience

    I have crossdressed swimwear and leotards for as long as I can remember. I almost always add panties and some kind of tights underneath. I don't typically try to pass as a girl or bother with wigs/ makeup,etc. Usually I just put a short shirt over the leotard or swimsuit so...
    Phboy Phboy 41-45 5 Responses Mar 27, 2010

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    Another Add To My Collection

    Just got a new swimsuit today, i have taken pictures of it, you can se them in my profile, please leave some comments :-)
    bodylower bodylower 31-35, M Jul 27, 2011

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    Paddling Pleasure

    One thing that I enjoy doing is kayaking on a peaceful river in northern New York. One thing I make sure of wearing under what I set out in, as it is relatively unpopulated, is a nice blue one piece woman's bathing suit, compliments unknowingly from my wife, while paddling. When...
    iwearsilkiesman iwearsilkiesman 51-55, M 3 Responses Sep 6, 2011

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    My Dream

    I'm a Bi M/F Transgender Surfer. I've been a surfer all my life, the bi and the transgender stuff I've just owned since retiring from my job of 37 yrs. and moved away from my home town. The Bi thing, well everyones into diversity when it comes to sexuality now a days, no biggie...
    deleted deleted 26-30 1 Response Dec 16, 2012

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    Sexy Swimsuit Pics

    I've uploaded some very sexy pictures of me in a new racer back swimsuit that I tried on in a dressing room. What a rush it was sneaking it into the dressing room. I did it where no one could see me but I think I secretly wanted someone to see me. And when I left it in there when...
    Ready4You Ready4You 18-21 Feb 15, 2013

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    The Story Of My Piece Swimsuit

    One day we played crossdressing whit my neighbors encourage me to put on one piece swimsuit with my sister, at the time I laughed a lot, Looked very cute as a boy of 8 years and had not hair on legs, stared my fascination for using it under my normal clothes and not one noticed...
    faceta faceta 22-25, M 1 Response Dec 8, 2011

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    Always Loved the Look of a Swimsuit

    Ever since I saw 1 piece swimsuits for girls I knew I'd love them. I spent my sumers around a pool from ages 7-11 and for those 4 years I always wanted to try a one piece swimsuit. Then when I was 13 I saw there was a store that was selling some, so I got some money and secretly...
    TCD20 TCD20 18-21 3 Responses Apr 19, 2009

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    The Day Out

    today was a perfect day other than the weather, i got up took the much needed shower then got dressed for the day... i picked from my many different swimsuits a medium blue and dark blue one piece then pick out dark suntan pantyhose... i put them on the the swimsuit then put my...
    mrmeimme mrmeimme 36-40, T 2 Responses Nov 9, 2010

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    Hanging Around In My Bikini Swimwear

    Now that the weather is finally warming I'm looking forward to pulling out my bikinis to wear around the house. Thinking of them from last summer I just posted pictures of a few of them, and I'm looking forward to adding to my photos with some of my new bikinis shortly. I just...
    Iwearthepanties Iwearthepanties 61-65, M May 30, 2013

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    Love Girls Swimwear

    I have always loved girls swimwear, the look and feel of it is such better that what blokes get to wear.I have several one piece suits, and some bikini bottoms, but my favourite at the moment is my new swimdress.  I ticks all the boxes, tight fitting suit with a skirt to...
    pantylover5099 pantylover5099 36-40, M 5 Responses Jan 8, 2010

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    New Girl On The Beach

     Jeff was ready to show off his new beach body, but dare he?   Jeff was torn with indecision. He had spent months preparing for this moment and now he was ready to enjoy his first trip to the beach dressed as a girl. But now, as he looked out at the crowds milling around on the...
    sammi11 sammi11 41-45, T 29 Responses Aug 6, 2011

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    New Catalina One-piece

    I had went shopping today and I decided to purchase a new swimsuit. I really love how they feel so I worked up the nerve to go to the rack in walmart and search. I've done this before but I had to give them away. So now I'm tring to rebulid my collection. The suit I bought is...
    deleted deleted 26-30 5 Responses Jun 18, 2012

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    I Love Wearing Women's Swimsuits!

    I love the way the nylon of a woman's swimsuit feels against my skin. I would almost rather wear a woman's swimsuit than my own, but am afraid people would laugh about how I look.
    rick105 rick105 26-30 13 Responses Jan 26, 2009

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    My New Bikini

    Lady just came home from Her daily shopping trip.  “I have a present for you,” She announced, “get the box from the car.”  It was a small box, but Lady does not carry anything from the garage up the stairs to the house.  The box was not...
    redlace redlace 61-65, M 6 Responses Mar 10, 2010

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    Talking

    i love crossdressing in swimsuits but i havent been able to do it in a while someone talk to be and maybe show me some pics ?? lol idk kik weshouldtalk098
    weshouldtalk098 weshouldtalk098 18-21 2 Responses Nov 3, 2013

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    Showering Together In Swimsuits

    We had just finished dinner and didn't feel like going out. We both complained of how disgusting we felt since we had just been at the gym before we had dinner at home. My girlfriend wanted to shower first but I had an idea. "Why don't we save water." I told her. "What do you...
    southbeachkid35 southbeachkid35 26-30, M 1 Response Feb 12, 2013

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    The Fourth Of July

    This fourth of July my wife thought it would be great to have a nice pool party for the fourth. But wanted everyone to have the same thing on so this is what she did. She had got a red white. And blue slim suit for me and flag swim suits for my 3 daughters and a flag two piece...
    lifewithbreasts lifewithbreasts 36-40 3 Responses Jul 6, 2013

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    Lots Of Pictures

    of me in my swimsuits in my profile, have a look and please leave a comment :-)
    bodylower bodylower 31-35, M 6 Responses Feb 9, 2011

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    Hot Tub

    I really enjoy our hot tub. I have several 1 pc swim suits. I especially like the style like Marlyn wore. The material not only feels so good against my skin, but it has this smell, I really can't describe. It's very intoxicating.
    Diana46 Diana46 61-65, M 3 Responses Feb 8, 2009

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    Thong

    As I don't really like the thong swimwear on offer for men, I often wear ladies thongs when I go to the beach. Another thing I love to do is wear a pair of panties under my shorts when I go to the beach, then watch if anyone notices them when I remove my shorts and start to...
    accordinglyford accordinglyford 36-40, M Sep 12, 2012

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    It's Just My Experience.

    My first name begins with E. and I was born in 1977. Ever since I was a teenager and went to school I have always been deeply attracted by women's one-piece swimsuits and leotards, at that time I used to spend hours at the pool looking at the girls in their beautiful costumes...
    deleted deleted 26-30 7 Responses Mar 24, 2010

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    New Pics

    I have just uploaded some new pics of me in my new swimsuit. Plus I would like to say that I'm also sitting here wearing the same suit and I love it. Just being able to express myself is good I just wish society would leave us alone and let us wear what we wanted to any time we...
    deleted deleted 26-30 Jun 24, 2012

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    Wearing Womens Swimsuits

    I have worn a womans bathing suit, both a one piece swimsuit and a bikini swimsuit. I like the feeling of the heavy spandex material against my body and also the look of a womans swimsuit. I have *********** several times wearing both a one piece swimsuit and a bikini swimsuit...
    pantiescouple pantiescouple 26-30 1 Response Feb 28, 2013

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    New

    got a few new swimsuits, pic's are posted in my profile, please have a look and leave a comment or two :-)
    bodylower bodylower 31-35, M Apr 13, 2011

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    First Time I Crossdressed...

    I borrowed my mother's 1 piece bathing and *********** in it.  I don't know why I just always thought they were sexier than 2 piece suits. Another time while on vacation in Mexico, I borrowed the ladies swimsuit who was staying in the room next to us, she hung it out to dry...
    l49331 l49331 18-21, M 6 Responses Aug 12, 2009

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    A Big Step

    Years ago I wanted a ladies swim suit. I had been wearing dresses, footwear, lingerie for a long time, but swim wear was so much different. Just after marriage, my wife began encouraging me to get one but I wasn't sure what I would do with it. It's one thing to wear ladies shorts...
    janusatv janusatv 61-65, T 5 Responses May 15, 2012

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    One Piece Thongs

    For the longest time I've loved one piece swimsuits as well as leotards and tights. As far as the swimsuits go, my favorite style is the high cut one piece thong. I bought several from Brigite and Skinzwear and have worn both to the local beach here. There's a section where the...
    leotard7230 leotard7230 46-50, M 2 Responses Feb 5, 2010

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    Bath Time!!

    when ever i take a bath i always wear a womans 1 piece bathing suit and just sit in the tub wearing it <3
    addguy3455 addguy3455 18-21, M 2 Responses Dec 7, 2012

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    Related Experiences

    Hello everyone I am a 19 Year old Male who previously got addicted to crossdressing. I am strait but for some reason love to wear females clothing, I have tried on several of my...
    MsLexi MsLexi 18-21, F 1 Response Aug 18

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    Every week or so I change my mind about crossdressing. I think its weird and stop, and then later the urge to crossdress returns. I believe it will never go
    kylexdress kylexdress 13-15, M 9 Responses Aug 4

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    So this is a big step for me. I've never been incredibly public about my crossdressing. This is the first thing i've ever done online relative to it with any kind of public...
    EmilyRose15 EmilyRose15 16-17, T 3 Responses Aug 7

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    So, I am fairly new to crossdressing (been at it for about half a year). I keep it a secret and I'm perfectly content with it staying that way. But it has always been a desire of...
    SuperCornstock SuperCornstock 16-17, M 2 Responses Aug 10

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    It's Varied over the Years. In my teens, it was a big part of my sex life, both solo and with my buddy, and to a small part, with a few girls. Then I thought I'd outgrow it. Ha! I...
    AmberFountaine AmberFountaine 66-70, M 2 Responses Aug 10

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    I was Caught Crossdressing by my next door nebor Guy and Im still doing it to day. I was in my Wifes We are the same size too. Well I was in her 34-C push up Bra, and Bikini...
    Kellyboy541 Kellyboy541 56-60, F 6 Responses Aug 21

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    I just like seeing a woman with a curvaceous figure wearing a bikini any height or weight they're all good to me...
    bignatbreastluver bignatbreastluver 46-50, M Aug 6

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    I had a stash of a few of my girlfriends clothes under a mattress that's under my bed. I went camping for four days and my mom decided to clean the entire house. When I got back my...
    sammixdress sammixdress 18-21, M 4 Responses Aug 2

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    Hey ladies; I wasn't quite sure which group to put this in but here it goes. I need laundry help; I never usually do my own laundry, so I'm not sure how to do my feminine...
    JessicaCD20 JessicaCD20 18-21, M 2 Responses Aug 3

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    I once fell asleep (druged) wearing a bra, top,panties, skirt, high heals, and panty hoes. And woke up on my stomach with my *** hanging of the side of my bed, my as* hole...
    bottomslut1 bottomslut1 18-21, M 3 Responses Aug 4

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    if anyone has read my most recent story you know i got the house to myself for 2 weeks and have been girly the entire time its perfect :) but i have noone to share this great...
    dawncutie dawncutie 18-21 6 Responses Aug 6

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    Ten years ago I would have used the word weird, and many other similar words to describe cross dressers. However that has now changed, I use words like delectable, mouth-watering...
    kinkycoupleuk kinkycoupleuk 46-50 7 Responses Aug 6

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    I swiped my first pair of panties from a friends sister when I was 9. By the time I was 11, I had collected quite a few pairs from her and my cousins. I kept them in a shoe box...
    Bobbie1952 Bobbie1952 61-65, M 4 Responses Aug 7

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    Right now I am sitting in my office wearing only my nightie as I do every morning. My office is detached from the house and I thought I just heard a car door close. I walk out...