Business trips

[sandy_folsom]

I rarely get the opportunity to go on business trips, once every few years. When I do go on trips, I always pack a chemise, panties, and a sexy pair of shoes (pumps or stilettos). After I am in my hotel room for the evening, I would strip off all my drab clothes and lounge around in my feminine clothes, even sleeping in my chemise.

The odd part is that there are no restrictions at home for doing the same thing. My wife won't mind if I wear a nightie to bed. For some reason, it's the feeling of just being in a new place and dressing up. I haven't yet ventured out of my room yet dressed up. Partly because the feminine clothes I bring are not suitable to wear in public and also don't want to be caught by any coworkers. However if I'm ever on a trip by myself...

Have other folks dressed up while on a business trip?

[alliy377]

Hi Sandy. I've done the same thing a couple times while traveling for business. One time at TSA they searched by carry on and found my breast forms! Awkward!!!!!!
But at home, I sleep every night dressed. My wife don't mind that, but I can't dress during the day, only on weekends. Not a bad thing.
Alliy

[Bluesman]

I've only had two business trips in my time and I did the same thing. At the time my dressing was strictly limited to panties, bras and nightgown and I was not fully out to my wife, so it was quite a thrill to return to my hotel room after work and lounge around in panties and bra, and then sleep in my nightgown. I wore panties every day. The first trip took me to Zurich (I'm in U.S.)and I added on a week, rented a car, and explored Switzerland and the Alps, underdressed in bra and panties when driving, sightseeing, hiking or eating out. Second trip was to Toronto. Only three days, but dressed in the hotel room. I even visited a dominatrix there for a forced feminisation session. It was fun, but, like many fantasies turned into reality, not as exciting as the anticipation. Glad I did it, but no inclination to do so again. Those were good times. I'm fully out now to my wife, and can dress at home when I wish to, which is good, but sometimes I still miss the thrill of those hidden "taboo" experiences.

[NjJamie]

Sandy, great topic and YES! I so miss the trips, actually had an assignment that had me in DC for the work week for over 6 months, probably dressed 80% of the nights and even got to visit Elizabeth Taylor for a makeover, I highly recommend it for everyone.

I usually dressed for the 4 hour drive home, had a few shopping stops along the way whenever able, Kohl's, JCP, Walmart, etc. At the time I would sometimes be able to dress at home but it was not often and not really in a friendly setting, things have gotten much better now so that's a huge improvement even if it's not nearly 4 nights/week.

One of my favorite evenings was to bring in a meal, usually a salad or something light, then iron my shirts for the week (even if they didn't need it!) and otherwise relax and enjoy the moments.

[Fiona_44]

I am retired now but used to travel a lot for business. I often brought some lingerie with me to dress in the room.

[NancySue]

Yes, almost always. I never ventured out totally dressed, but did underdress.

[MonikaCD]

Couple of years ago I was going on business trips every other month and staying at hotel for 2-3 days, so I had plenty of time to crossdress. Unfortunately I was not crossdressing those years yet. :( I usually just bought some pantyhose on my way there and wore them in the hotel in the evening and once I even bought a pair of high heels which was something extra. I had to throw everything away on my trip home as I haven't yet discovered that I could stash it somewhere.
When I discovered crossdressing some time ago, I didn't had any opportunity to travel. That lasted until late 2022, when I was able to drive to other town en femme, but without interacting with any other people - refueling in the middle of the night on self-service gas station, self-service checkin to rented apartment, visit to a self-service shop in the middle of the night... but that was kind of breakthrough before my next business trips, but that is another story that I may tell one day, though you may find some hint in albums on my Flickr page.

[SophiaRose]

I'm out of town on business right now and yup, dressed as I type. My suitcase was packed more than usual: Three dresses, two pairs of pantyhose, body shaping suit, panties, bra and night gown. Couldn't wait to get of drab and be myself. Never left the room. Maybe someday when I feel I could pass better.

[Sandi Beech]

Haha, yes just a few. I posted all the clubs I have been to dressed up a while back in this post.

https://www.crossdressers.com/forums/showthread.php?283931-Places-I-have-been-to-Crossdressed&highlight=

My biggest problem is keeping my girly suitcase under 50 lbs for air travel ; )

I have a number of threads about my outings. It has been a lot of fun for sure.


Sandi

[Traci H]

Retired now, but many of my business trips included some crossdressing. When traveling by air, it sometimes limited how much I could pack. One time I was taking a road trip with a female co-worker and I swung by to pick her up. As she put her bags in the trunk, she commented I had more luggage than a woman. If only she knew. I fully dressed and walked outside that evening, fully enjoying it.

[Kayy]

Me too, when I was still in the closet trips away (two or three a year) were an opportunity to get dressed up without a chance of my wife finding out. Now I’m retired but also fully ‘out’ and supported by my wife, but I still miss the trips.

[Sometimes Steffi]

I remember business trip adventures, one in particular. I was packing my suitcase for my next business trip, including some girly stuff. My wife came home from church early and caught me packing a bra. The best response was the truth, but that didn't go very well. In short, "It was a terrible, horrible, no-good, very bad day."

But, I did have a lot of very good experiences. One one trip, I broke the "shopping (in person) barrier" and rather than a large sonic boom, there was barely a whisper. I did a lot of in-person shopping while on business trips. I was on a number of extended business trips of several weeks duration. My company didn't pay to fly me home each weekend, but they did cover my room and board. On one business trip, I bought so much that I had to buy a duffle bag to get it home. On another business trip, I shipped some stuff home to my PO Box.

I got my first makeover on a business trip, and I took it on a test drive Out and About in the "gayborhood". I met some online friends FtF, or IRL (even some friends from here) en femme at events while on a business trip several times. I met a TG group in Denver for dinner at a restaurant and a private shopping experience at a woman's store. I got a pedi on a business trip a couple of times. I went to yoga classes and to the gym in hybrid mode

[bridget thronton]

Some business travel (but not much) - drive dressed if distance is not far, pack a dress, bra, sandals, and nightgown if I fly.

[siva]

going on a business trip in august so looking forward for the dress up

[Stephanie47]

Once I had a business trip that ran from Monday to check out on a Friday morning. It was a drive, so no issue with packing luggage. I stayed at a Marriott that had a kitchenette, closets, etc. It was great to hang dresses in a closet, line heals up, etc. I bought along several nighties to sleep in. This was 1992. I still have one of the nighties which I still wear on occasion.

[beckymarie]

I have traveled extensively for business over my career and took advantage to dress and get out where there was almost 0 chance of encountering anyone I knew. I had multiple occasions where I visited the same location every week for a few months and would leave my suitcase of girly things at the hotel over the weekend and took advantage of the hotel laundry to keep things clean. Sadly, those days are over.

[kimdl93]

Of course, I often dressed and went out, while on business trips. I also dressed daily at home when my wife was traveling routinely. Eventually, I just hated, I mean hated changing back to male mode upon her return. Although she knew of, tolerated, and at times tried to be supportive, this proved to be a bridge too far.

[Vintage4sarah]

I didn't go on trips a lot, but when I did I made the most of it. It was on these trips that I gradually "put my foot in the water" and first started to go out as Sarah. This gave me the opportunity to get comfortable out as Sarah into public. It also spurred me to develope a wardrobe that allowed me to blend in and make it all easier. From these trips I then arranged meetings and social time with others.
Now that I am fully retired, I still go to several collectors' shows for over nights away from home.

[alwayshave]

My last business trip was to Korea a few years back, and of course I was underdressed and at night wore a nightgown at night.

[CharlotteCD]

I have a hit and miss for my work trips. Sometimes I am going to sites that involve bag searches and full car searches.

If I am going somewhere that I can leave my clothes safe or that I am not subject to security then I will definitely take my clothes.

[NatalieMN]

I rarely went on business trips about 15 years ago and I didn't have a partner at the time. I did live with other people though so I definitely took advantage of the time away to not only dress (primarily in panties, bras, and nighties like a few others) but also go out shopping underdressed. In fact, I think these were the first times I would go out shopping for feminine clothing at all since I could be certain I wouldn't meet anyone I knew. It was exhilarating and really got me more comfortable in shopping for myself.

[PaulaJeanette]

Before retirement, I traveled quite a bit for my job. These were wonderful times as they provided the perfect opportunity to dress and indulge Paula time when alone in my hotel room. Since I was not passable, most of my evenings were limited to my hotel where Paula enjoyed her lingerie consisting of matching panties, bras with breast forms, garter belt with stockings, and heels. In addition to dressing, I enjoyed many evenings lounging and sleeping in sexy, flowing negligees. I felt so special during these self-indulgent moments. My travels also afforded opportunities to leisurely shop as the chances of being seen by family or friends was slim to none.

Because most of my business related trips involved air travel, I usually traveled with two suitcases; one for my male clothing and the other for Paula. As bag inspections began, I routinely did curbside check-in to separate myself from my bags when they were inspected. Of course, Paula's suitcase did not contain any identification of my male self and vice verse. I am sure my wife was somewhat puzzled as to why I took two bags regardless of the trip duration.

Enjoy these times!

[siva]

i am going on a business trip 4th week of august to Miami. i am planning on trying enfemme after security. i fly out from dfw and since i know few people out of dfw can't dress, so i am planning on dressing up after I land at the connecting airport
what kind of tips/tricks you girls can provide, not sure where to do the makeup, dress change probably at a family restroom is easier
can I carry breast forms
how should I react if somebody says are you a male in the airport or flight attendants or gate agents or TSA?

[alliy377]

Siva,
I mentioned earlier I had my breast forms in my carry on once flying out of Regan. TSA searched it and pulled them out and asked me if this was my bag. I had no choice but to say yes. Luckily, my wife had already passed through, because I could only imagine her reaction.
So, in a nutshell, you can carry them on, but be prepared. Since, I've put them in my checked bag, and as Paula mentioned, it separates you from your luggage.
Also, I have underdressed before in the airports, i.e. putting on my bra, no forms, after going through TSA. Didn't want to trip the x-ray with an underwire bra on!!!!!

[siva]

thanks Alliy. So what would TSA say if we have a underwire bra on? can I say them i have a bra while they pat me down

[Sometimes Steffi]

If in doubt, claim gender diversity. TSA has an app (https://www.tsa.gov/travel/tsa-cares/gender-diversity)for that.

Breast forms are considered "medically necessary medical equipment".

If you run into a problem, ask for a supervisor and wait patiently. It's the law.

I use a CPAP device. It's considered "medically necessary medical equipment". I always travel with my CPAP device and carryon. It's kind of delicate and very expensive (~$2000) to replace. Mine is about the size of medium-sized handbag.

Passengers are allowed to bring one carry-on bag and one personal item for free on most flights. I get to carry my CPAP device on in addition to the limit of two above. One time at boarding, I had a small carryon bag my computer (personal item) and my CPAP bag. When I reached the check-in agent, she told me that I was only allowed two bags. Right after that, she said, "Do you have a medical bag?" I replied, "Yes, this is a CPAP", and I showed her my bag. She didn't even inspect it but passed me right through with three bags.

Know the rules and demand your rights.

As I posted recently, I travelled with breast forms in my carryon bag. They were detected. I told the TSA guy what they were. He said they needed to be inspected. He offered me a private inspection.

For a while, I travelled with a lot of electronic test equipment, including a VOM in checked baggage. I also carried a lot of specialized test wires. I anticipated what in would look like going through X-ray. I think I locked it with a cable clip, mostly to know if it was opened. I used a colored cable clip not found in the standard package to make it easy to detect if my bag had been opened. Inside the bag, I had an inventory of equipment, the purpose of my trip and a copy of my FAA Contractor badge. Sometimes my bags were opened and inspected, but not always.

[siva]

thanks Steffi

i am planning on trying en femme after security
what kind of tips/tricks you girls can provide, not sure where to do the makeup, dress change probably at a family restroom is easier
how should I react if somebody asks - are you a male in the airport or flight attendants or gate agents?

[Sometimes Steffi]

If anybody asks, it's none of their business, unless you'd like to engage them in conversation.

If you don't want to talk, I think saying, "What do you think" might be kid of of-putting enough to get them to walk away.

I take a long time to dress and I wouldn't want to occupy a single seat family restroom for that long.

I couple of times I went early to my therapy appointment to get dressed. The girls bathroom had a better mirror than the men's so I decided to use it instead. I prepared a sign, "Sorry. Restroom is out of order. Please use the restroom on the second floor Thanks.

[siva]

thanks
can they take you off the flight for being dressed in a different gender that's another thing i am worried

[Sometimes Steffi]

In the US, no. There's no "dress code" requirements, although there have been some women who were required to cover up or be removed from the plane because they were dressed to skimpily. Dress to fit in and you shouldn't have any problem

As I said, claim gender diversity. TSA has an app (https://www.tsa.gov/travel/tsa-cares/gender-diversity)for that.

Gender Diversity is covered under the Americans with Disabilities Act (ADA). ADA is a Federal law to protect people with disabilities, like mobility, vision or hearing. I don't personally believe gender diversity is a disability, but I'm willing to accept it if it comes for free.

There are special exceptions (https://www.aveloair.com/help/exit-row-requirements) for "permitted" disabilities in exit row seats. Flight attendants have a right to question you about whether or not your disabilities exclude you from sitting in a exit row "because you can't perform the duties required". Even someone who doesn't speak English fluently may be excluded because they "Must be able to comprehend instructions from the crew.

Note that these are general guidelines. There have been any number of "weight challenged", specifically, those that can't fit into their assigned seat without blocking the aisle or encroaching on their seatmate's space. Sometimes, if they need two seats to "fit in", they need to buy two seats.

[siva]

thanks Steffi, once I am done with the trip, will update how it went

[TheHiddenMe]

thanks Steffi

i am planning on trying en femme after security
what kind of tips/tricks you girls can provide, not sure where to do the makeup, dress change probably at a family restroom is easier
how should I react if somebody asks - are you a male in the airport or flight attendants or gate agents?

Why are you changing after security? You can be dressed and go through security. I have at least 5 times now without issue (even got compliments).

One time I was going through security and the TSA agent looked at my ID (guy, of course) and did a double take, so I guess maybe I wasn't quite as detectable as I usually think.

They are trained to deal with Transgender people. It's not a big deal. Just go through security dressed.

[Jillcder]

I love being retired but I definitely miss the opportunity to Crossdress on my overnight business trips. I giggle when I think about my hotel rooms having dresses, skirts, tops, wigs, shoes, scattered around the room and of course my bathroom counter was always covered with makeup products.

[Helen_Highwater]

My work would take me away from home sometimes for a single night, others for days or even weeks. Early on I can remember taking so much stuff with me. Bags of clothing, the reception staff must have wondered what I needed so much for just a one night stay!

[siva]

Why are you changing after security? You can be dressed and go through security. I have at least 5 times now without issue (even got compliments).

One time I was going through security and the TSA agent looked at my ID (guy, of course) and did a double take, so I guess maybe I wasn't quite as detectable as I usually think.

They are trained to deal with Transgender people. It's not a big deal. Just go through security dressed.


Hi Sun-Dee, I know most Gate Agents personally at DFW airport where I flyout from, so didn't want to do it and I can't dress from home either and leave to airport