Cross-dressing at an Island Resort

[Kimberly Kael]

I just got back from a week-long getaway and my very first attempt to bring some of my emerging feminine self with me on vacation. The process of packing for the journey was fascinating in its own right - I now have a lot more sympathy for the intricate outfit coordination and packing process, and realize why women need so many changes of clothing! Weather conditions were tricky to anticipate, and evening wear demanded everything from subtle additions to whole new outfits. Throw in the need to pack some basic makeup and it took me twice as long as usual to pack.

... and I wasn't even planning to go in full femme mode! As supportive as my wife has been I was still a little worried about how she would react to some of my packing choices and knew that packing breast forms was out of the question. Still, almost everything I wore during the trip was designed for a woman. Some straddled the gender borderline and others were blatantly feminine, but despite some trepidation about possible reactions it sounded like a real adventure.

So how do people react when confronted with some fairly obvious cross-dressing in an island resort setting? As expected there were some frowns from men and more conservative appearing couples, but given that I was expecting at least a snide remark or two and never had any confrontation? I was very happy. The staff was wonderfully friendly, and I was met with smiles by the vast majority of female guests. Every time I greeted someone or initiated interaction things got even more relaxed and even men seemed to quickly discard their preconceptions and engage in conversation despite the lacy camisole on display in my v-neck tops, the purse on my shoulder, and some of my favorite earrings. Lesson learned? There's no point in waiting for someone else to get the positive vibe started, so don't walk around with a chip on your shoulder. The more comfortable I acted, the more comfortable everyone felt.

The trip even offered several opportunities to expand my wardrobe and accessories. Shortly before leaving I picked up a cute, short swim skirt that wound up being the only bathing attire I wore on the trip even though I brought some more conservative options just in case. I even wore it with a cute tank top on a hike from the beach. I forgot to pack my sunglasses and picked up some adorable rose-tinted glasses with subtle jeweled adornment that I wore throughout the week. This wasn't the only shopping opportunity on the trip and I picked up a few fun articles to wear while glorying in the absurdity of female clothing sizes. I agonized briefly between L and XL in a shirt , tried and failed to buy a lightweight rain jacket that was just too tight in an XL, but my favorite find was a pair of XS pants that fit with room to spare! No wonder men give up trying to buy clothing for women.

So while I never tried to pass as a woman during the trip I really enjoyed expressing my femininity. The resort environment felt like a safe haven for my exploration and I can't wait for my next opportunity. I'll be actively looking for a femme trip in the new year (Diva Las Vegas, perhaps?) so I'd appreciate any suggestions for my next step.

[Veronica Smith]

My wife and I are planning to travel to Hawaii this winter and I'd love to spend much of my time wearing feminine clothing. If I understand correctly, you weren't trying to pass as a girl, just wearing the clothing you prefer while otherwise being clearly a guy. Is that correct? I'd love to be able to do that. I bought some Westbound tropical print blouses last fall that I hope to wear there along with my ladies shorts. I've also got some ladies polo shirts that I hope to wear. And I love to wear a bra and a camisole under some of my male tropical shirts I own.

Thanks for the encouraging story!
Veronica

[DonnaT]

Did your wife go wth you? If so, what were her reactions to your attire?

[Kimberly Kael]

My wife and I are planning to travel to Hawaii this winter and I'd love to spend much of my time wearing feminine clothing. If I understand correctly, you weren't trying to pass as a girl, just wearing the clothing you prefer while otherwise being clearly a guy. Is that correct?

Yes, that's it exactly. I suspect some people would rather be "fooled" than have someone obviously cross-dressing, and reactions were more polarized by outfits that were undeniably female (my wife claims that anything lacy is a dead giveaway and so the visible camisole fell into that category, but I even wore that on the flight home.)

Thanks for the encouraging story!

I'm glad to hear you appreciated hearing about it. Your mileage may vary, but for me it was a very freeing experience. Hawaii isn't known for being particularly tolerant so I would definitely avoid going to a bar frequented by locals or anything like that, but in a more controlled upscale resort environment it seemed fairly safe.

[Kiera Kael (SO)]

I did indeed accompany Kimberly on the trip! I love the way my sweetie looks in "borderline" attire and a little eye makeup but to be honest, I would not have felt comfortable if she'd chosen this trip as the time for a dinner totally en femme.

As it was, there was only one episode that freaked me out. We were having dinner in the "fancy" resort restaurant one night and Kimberly was in one of the more blatantly feminine outfits. I noticed a conservative man at the next table scowling at us and shaking his head. Okay, I could live with that - it's his problem, not ours. But when Kimberly got up and headed to the bathroom, the man actually followed her! Call me paranoid - it might have been coincidence as he did not accost Kimberly - but he did return following close on her heels. Nothing came of it but my heart stopped for a few minutes while I was sitting at the table waiting for Kimberly to return.

So Veronica, I say wear those blouses proudly but please stay safe!

Kiera Kael

[Kimberly Kael]

Did your wife go wth you? If so, what were her reactions to your attire?

We were together for the entire trip. She was, as always, supportive but concerned about my safety and happiness. She is happy to offer advice on my outfit for the day but is willing to go with whatever I settle on. I think there was only two things that clearly made her uncomfortable.

Once was when I got up to go to the washroom, and someone from another table who she thought hadn't reacted well got up to leave immediately after me. She thought it was possible he was checking to see what washroom I used (the men's, as I wasn't trying to pass as a woman.) I didn't notice anything and while I did meet someone on the way out who did a double-take I greeted him politely and he returned the greeting in a startled but otherwise friendly tone.

The other was when I showed her one of the outfits I'd brought - complete with skirt and blouse. I never did wind up wearing the skirt but I wore the blouse one evening and she wore the cute little half-jacket I had brought to complete the ensemble. I really wasn't sure that I would find the right opportunity and had only brought the skirt in a move of sheer optimism. Maybe next time.

(Edit: I see Kiera posted her own reply before I finished mine - now you have both perspectives!)

[Virginia]

Well I definitely commend your wife and thank her for posting. Glad you both had a good time and were in sync on the clothing.

I have to say that virtually everyday that I go out I am wearing feminine clothing, but it is androgynous enough so as to not raise too many eyebrows. With the colder weather, mock turtle neck cable knit sweaters with jeans or girl's slacks and silk print blouse under a girl's heavier outerwear coat. Depending on the time and temperature usually panty hose are the order of the day as well, with white socks as my shoes fit better that way.

On several occasions while travelling dressed, I have checked in with my credit card and driver's license and have never had anyone question me.

It is fun to "Push the envelop" as it were, isn't it!!!??

Oh, there is a CD/TG cruise being planned over Halloween 2008. Four days to Mexico, I think, and the price starts at $399.00 out of Miami per person. SL and I are considering it, unless I make the World Team and have to go and lift in the World's.

Anyway, just have fun, we only go around once!

Virginia

[Jeannie]

Hi Hon
That's a great story. I love it! One tip. If your wife is a bit skitish about your look, just go to San Francisco or Provincetown for your next vacation. They will be giving your wife the eye at dinner and if you are in Provincetown you'll drink free all night and if they hit on you when you're leaving just say" Thanks so much but I'm with him." Trust me. It works but your honey will be rippin'! I told Mini we should take separate vacations but she had to learn the hard way Virginia. Too bad. I warned her! Life isn't a bowl of freakin' cherries you know!Hugs


Love
Jeannie


PS I sent a Chritsmas present to you two but I have to send another one. It was confiscated by the Postal Authorities. Lucky I put Lorna's return address. I did send her the bail money though.

[KimberlyS]

Kimberly and Kiera that is so great and sounded like so much fun. I am glad you enjoyed your selves. The two of you rock. I would love to do that with my wife, but she would freak.

Kimberly you said
"The more comfortable I acted, the more comfortable everyone felt."
That has been my experience no matter what my presentation.

I do push the boundaries quite a bit also when I travel alone and not around anyone I know. Like you said, I get some scowls mostly from guys, knowing smiles from quite a few gals and some some questioning and other interesting looks from guys and gals. Similar to what you said Kimberly, an obvious bra under a top or cami draws many looks, as does a bra with forms.

Veronica I would say go for it with confidence.


KimberlyS-CD
joe in a skirt

[Gaven McLaren]

I was in St Augustine, Fl over the past weekend with my mother and my stepfather. On Saturday I was wearing a white button up shirt with a gray cami with black skirt. It was the first time I had wore anything like that around my mother. I got quite a few odd looks and a few people that had the question "Is that a guy in a skirt?" My mother did tell a group of people "Yes he is a guy in a skirt." We were looking at Flagler College and there was a group of ladies that were sitting on a bench and we were joking about telling them to take a picture it will last longer. When I get home and back to my drive for my laptop I will upload some pics of that weekend on my Myspace page. Any pics from on Saturday I will post in the gallery.

[Anita]

Hi Kimberly--
I'm happy to hear that it went well for you and your wife. It takes some courage to try something as different as this in a strange environment, but when it works it really enriches the whole experience. Doing partial femme seems to me to be the hardest thing that you can do, so give yourself a pat on the back. And then keep on doing it, finding what works for you.