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I Crossdressing Swimwear

Personal Stories, Advice, and Support 644 People

    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
    1 Response Feb 1, 2011

    In High School

     My parents helped with a youth event and for some reason we had a girls one piece bathing suit at home for a long time. I would put it on and wish that I could go swimming in it.  
    deleted deleted
    26-30
    Jul 7, 2009

    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

    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
    3 Responses Aug 12, 2009

    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
    10 Responses Jan 26, 2009

    TV to Swimwear Transition

    My TV habits has been around since I was 8 or 9 years old, and wore both my sisters and mothers things like nylons, panties and the occasional bra. By the time of college, I had been crossdressing for a few years but I didn't own too much stuff. Usually things GFs tossed out out...
    jhenry922 jhenry922
    41-45
    2 Responses Jul 17, 2009

    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
    3 Responses Sep 30, 2011

    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
    4 Responses Mar 24, 2010

    (note: this story is not about me crossdressing

    lol, so the title's a bit misleading, although I have worn boys' trunks as bottoms a couple of times just for the heck of it :> ) I think boys in girls' one-piece swimsuits can be just as cute as girls, if not more. But I didn't always think that way..... I am good friends...
    nothingnobodynowhere nothingnobodynowhere
    22-25, F
    6 Responses Nov 14, 2014

    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
    3 Responses Aug 7, 2013

    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
    1 Response Feb 8, 2009

    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
    Dec 16, 2012

    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

    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

    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

    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

    I love wearing women's bikini bottoms to the

    beach, waterpark and to the pool. They feel and look better than a speedo. I have worn them for many years.
    swimguy0812 swimguy0812
    22-25, M
    Oct 4, 2014

    I have on a high cut women's lifeguard speedo

    swimsuit. I feel so feminine and sexy I have to strut around with high heels on. Love the look and feel of it.
    deleted deleted
    26-30
    Sep 7, 2015

    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

    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...
    deleted deleted
    26-30
    1 Response Dec 8, 2011

    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

    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

    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
    Feb 5, 2010

    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

    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

    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

    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
    1 Response Nov 3, 2013

    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
    2 Responses Mar 10, 2010

    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
    4 Responses May 15, 2012

    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

    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
    2 Responses Apr 19, 2009

    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

    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
    56-60, M
    2 Responses Sep 6, 2011

    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
    2 Responses Mar 27, 2010

    Bikini Day At The Beach, Caught In School

    I have worn one and two piece suits for years.  I worked at a local public pool in high school.  We always had boxes of suits people had left.  Lots of the female staff would pick through them.  I grabbed a couple of the suits and stuffed them in my gym bag...
    talltabatha talltabatha
    46-50, T
    1 Response Mar 26, 2010

    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
    24 Responses Aug 6, 2011
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