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 Crossdressing Swimwear

Personal Stories, Advice, and Support 616 People

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    Newbie

    I just started wearing a woman's swimsuit to swim. It is Speedo's hydrasuit. The legs are cut rather high, but I wear a pair of trunks over it to reduce the shocking impact to others swimmers at the pool. Together with the trunk, the swimsuit doesn't look too female. The suit...
    kidme kidme 36-40 1 Response Jul 23, 2009

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 3 Responses Nov 3, 2013

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 36-40, T 7 Responses Nov 24, 2012

    Your Response

    Cancel

    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 3 Responses Jul 17, 2009

    Your Response

    Cancel

    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 2 Responses Oct 14, 2011

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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 31 Responses Aug 6, 2011

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    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

    Your Response

    Cancel

    Related Experiences

    Maybe we beautiful women should play on the beach in Summer hot days. So a piece of swimwear is necessary. We like to buy swimwear online, I can recommend you a good place to shop...
    chowonion chowonion 22-25, M 4 days ago

    Your Response

    Cancel
    Hi. Im a male 18 at college. Ive been crossdressing for a while but am looking for a female to talk with about it and whatever..message me on here
    Zxi19 Zxi19 18-21, M Mar 30

    Your Response

    Cancel
    A night out as Rhonda had me visiting a local establishment where a band was playing that I follow. I was with a friend, and she is very acceptable of my crossdressing. I was...
    SweetRhonda SweetRhonda 51-55, T 5 Responses Apr 8

    Your Response

    Cancel
    I want to know more about crossdressing
    nightfun56 nightfun56 18-21, M 2 Responses Apr 9

    Your Response

    Cancel
    I like Crossdressing. But I have never told anyone. Do you think I should?
    Pinklovemaddie Pinklovemaddie 13-15 4 Responses Apr 14

    Your Response

    Cancel
    I want a girlfriend who fully supports me crossdressing but I cant find anyone nearby.
    natessecret natessecret 18-21, M 1 day ago

    Your Response

    Cancel
    I argue with my parents a lot about my bikini, they say it looks to small, but really it makes me look sexy. My moms a b-i-t-c-h, she says it's not normal for me to show it off to...
    dakotape3 dakotape3 22-25, F 4 Responses 4 days ago

    Your Response

    Cancel
    I was tired, lonely and needed to relax. I went to the local adult video store and picked up a video. In it, there was a woman who was really cute who wore a white corset, and a...
    wistfulmiles wistfulmiles 51-55, M 5 Responses Mar 23

    Your Response

    Cancel
    I love wearing girls clothes the more girly the better. I'd love to chat to other crossdressers so send me a message :)
    deleted deleted 26-30 1 Response Mar 25

    Your Response

    Cancel
    I love to ware woman's underwear. Like bras and pantys. I have ever since I was potty trained in my cuz pantys. Is this ok?
    onomaine onomaine 22-25, M 3 Responses Mar 27

    Your Response

    Cancel
    I crossdress every chance I get. My wife knows but does not participate.
    cdtommy cdtommy 66-70, M 2 Responses Mar 28

    Your Response

    Cancel
    Hey im 18 in college. Anybody close to that age wanna talk or anything? Im a guy from ct/ny.
    Zxi19 Zxi19 18-21, M 3 Responses Mar 30

    Your Response

    Cancel
    Sometime my wife makes me cross dress
    bendoverman75 bendoverman75 36-40, M 1 Response Apr 2

    Your Response

    Cancel
    I should preface this with "I'm pretty sure this is weird," because even I get mad at myself for thinking it. Basically, I'm jealous of my boyfriend when he dresses. I realize this...
    Lynne82 Lynne82 31-35, F 4 Responses Apr 4

    Your Response

    Cancel
    Fem Sissy Boy is honestly searching for a masculine and protective boyfriend/husband and treat me as your princess wife! I am TG and would even love to dress for you and if you...
    FemGayBottom FemGayBottom 26-30, T 1 Response Apr 4

    Your Response

    Cancel