Sherry Ann's Big Adventure!

Part 1:

Hi everyone,

I had the adventure of a lifetime! I've dressed and gone out many times for a single day/night, but that's it. I always wanted to dress up and stay dressed for several days in a row. From last Saturday night until Tuesday morning, I finally had the chance. My (supportive!) wife is traveling this week and she encouraged me to grab the chance that she knew I wanted. So I did! @Teresa.smith.va also gave me good advice and encouragement.

I went to Boston, which I know pretty well and always felt comfy/safe there.

I arrived Saturday night in drab mode, because of circumstances. I wanted to go to Club Cafe (a popular LGBT nightclub), so I changed into shiny black pants, a blue/green sequined top, and black boots. The top is nicer than the picture indicates -- it's not so patchy in real life. On my way outside, I took the drab clothes from traveling and put them in my car, on the theory that if I wimped out from dressing one day and wanted to go drab again, I'd still have to dress up to go outside and get those drab clothes, in which case I'd be en femme anyhow so might as well stay that way! LOL it worked. I spent a few hours at the club, got invited by some cis women to dance in their group, and maybe got a little bit tipsy. :)

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Part 2:

Sunday, I slept pretty late. I woke up and put on a cool pair of space-themed black leggings, a black sweater, and a light blue jacket. I went out in black Keds, but they were hurting my feet (lots of brick sidewalks), so I changed back into the boots for the evening. I started the day by getting my first ever professional manicure! I spent most of the afternoon checking out an annual spring fair ("Mayfair"), and then tried -- and failed -- to find some interesting nightlife. I wound up at Jacques which is a famous dive/CD bar, but I was the only regular customer there -- everyone else was there for an amateur standup comedy night. They weren't very funny.

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I like seeing how I like from the back. :) (I always wear hip/butt pads when I dress, which helps sooooo much to create the illusion of a good figure!)

It looks like maybe I didn't (ahem) tuck well enough on Sunday. Oh well. Nobody gave me any indication that they noticed!

Part 3:

Monday, I slept late again, and put on a blue dress and cream ribbed shirt underneath. So now it was milestone territory -- my third straight day of dressing, and I've NEVER dared to wear anything showing that amount of bare leg. I've always worn pantyhose, stockings, etc., except with capris which only show your calf (where I'm not naturally hairy anyhow.) I shaved as closely as I could. Probably not good enough because it's hard to reach certain places! But I did my best. I went out in blue sneakers. Big mistake not wearing socks! They hurt the back of my heels, so I stopped at a CVS and bought white ankle socks. In retrospect, I wish I'd brought with me a cute pair of white * ruffled * ankle socks from back home. The dress looked better in real life than in the pictures, I think. I visited a museum and just spent a lot of time walking around the city.

That evening, I found drag queen trivia night at a local arcade! Super fun!!

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Part 4:

Tuesday, I had to wake up to check out of my room. I put on jeans and a black blouse. I had a pair of denim cuffed shorts that I reaaaaaally wanted to wear, but I wimped out, in fear that my legs were not shaved well enough or just the wrong shape without hose/leggings. I went to a local diner for breakfast, and then left for back home.

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I drove home still dressed, including at rest stops, for gasoline, etc. .... ALMOST got caught by a worker at the house next door (who knows me!!) when I pulled into my driveway, but managed to elude it. Whew!

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Overall, I had an AMAZING time being Sherry Ann for several days in a row!!! I don't know why I was so scared to do this before. Every time that I've gone out for one day/night, the worst part was going back to drab the next day. Getting to stay this way was ... I'm out of words for it!!! Shaving every day is something I hate :) but it was soooo worthwhile. Every time I stepped outside of my hotel room, and every time I had some interaction with another person, it made me happy inside.

There were two interesting interactions on Monday. Around lunchtime, walking down the street, a young college-age woman complimented me on my dress. Simply and friendly. But later that day, an older women practically ran up to me, just to say: "I saw your from over there, and wanted to say you look so well put together!" ... I know she was trying to be a good ally, but instead it made me think, "So you're saying you could tell I'm a CD, not a cis woman, from over there?"

Anyway: I highly recommend taking such an adventure for all CDs! I already knew from past outings that nobody really cares, and the only ones who speak up are those that are being friendly and accepting. (Although obviously it's different here in the northeast US than some other parts of the country/world.)

I'm still on a high from the trip. :)

That was a great adventure Sherry Ann! Thanks for sharing with us!
You look great in all the pictures and I can tell you were having a great time.
I like the leggings in Part2, and they really show off the shape!

It is great to be able to spend more time in girl mode for sure!
I am into week 5 now. It is getting interesting, thats for sure.

Thanks!!

Four days was enough to blow my girl mind. :) I had to go back to work and real life on Wednesday. I'm not interested in coming out to everyone in my family, work, etc., so for now it remains just between my wife, the Internet :heehee: and few most trusted friends.

Here are the leggings: https://www.amazon.com/dp/B07W3LKS1W

What a great trip Sherry Ann--you describe it so well. Thanks for the accompanying pics--you look great.

Very glad that you had a great time! Whats next?

Hahaha I have no idea what's next. For the last few years, I've * craved * an opportunity to stay dressed up for several days in a row. Now I've done that! Beyond that ... I mean I love finding new things to experience, en femme, but now I'm out of ideas! Maybe shave my legs well enough to go out in a miniskirt without any hose! :)

Do you have any (realistic) suggestions?

In stead of shaving your legs, try an epilator. It will look a lot better and last a lot longer before any regrowth appear. And when it does, it tend to be fine new hairs instead of stubble.
But do the epilation a couple days before you want to show off your legs since they can be a little red right after.

Possibly in the winter. I can't do that in summer, because I have valid reasons for my legs to look normal (hairy) in shorts most of the time.

Suggestion: Dress and spend the day running errands like any AFAB would!
Just a thought!
Hugs Lana Mae

Ah understood, so you are ok with the regrow time after shaving, but not the longer time after epilation.
Are they showing a bit of the leg version of 5 o'clock shadow after shaving? If that is the problem, you can try using a concealer and spread it out real thin and rub it in really well. It will help cover the pores.
Or, use a foundation in the skin color of your legs. This also helps even out any tan issues.

Finally, many women also have to shave their legs and can show a bit of the same problem, but you really have to look closely. Will anybody look that closely at your legs? ;)

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Originally Posted by Lana Mae

Suggestion: Dress and spend the day running errands like any AFAB would!
Just a thought!
Hugs Lana Mae

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I've done that!

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I don't want to get into the whole story here, it's just as you said though, normally my legs are quite hairy and it's NOT something that I can change in certain circles. I'd rather not discuss that further. I can go a week or so outside those circles, maximum.

OK!
Fly pretty! Possibly to a friend who knows a few states away!
Hugs Lana Mae

No of course. Sorry I asked.

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Originally Posted by Sherry Ann Evans

Hahaha I have no idea what's next. For the last few years, I've * craved * an opportunity to stay dressed up for several days in a row. Now I've done that! Beyond that ... I mean I love finding new things to experience, en femme, but now I'm out of ideas! Maybe shave my legs well enough to go out in a miniskirt without any hose! :)

Do you have any (realistic) suggestions?

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A transgender conference. for example, First Event (Boston), Fantasia (Provincetown) and Keystone (Harrisburg, PA) should all be within driving distance. Besides the four days and four nights all girl all the time, you will meet many CD/TSs and will travel with "a posse" wherever you go. Plus, you'll get to go to seminars that may be of interest to you. There's a sub-event where you wife can meet oter SOs of CDs. Go to a free clothing exchange to stock up on new outfits.

Thanks for sharing your pictures and activities - sounds like a great trip

Sherry Ann,

What to do next? Well you could do what I do and rent a place for an entire week and on top of the things you've already done being in self catering accommodation you have to go grocery shopping, you've plenty of time to go clothes shopping, Inc trying on of course. Stops for drinks and a cake give you more opportunity to interact with folks, then there's the cinema or theatre, restaurants, historical buildings and museums, zoos to visit, use public transport, bus, train, taxi. One of my fave days out is to catch firstly the train, switch to bus, to get to a large retail park and spend a few hours on retail therapy. On the return I spend time looKing around the market town, grab a bite to eat and a drink in a pub before going to the train station to make my way home and get ready for a night out.

Find out if there's a support group that meets in the area and time your stay to be able to join them and meet more of our community. Post here to see if there's folks off the forum you could meet up with which I've been lucky enough to do many times. It's so good to put a face to a name as well as share experiences.

Get a full makeover or at least get your foundation checked at a cosmetic counter. Have you ever had a wig fitting? So worth it.

Immersing yourself into being enfemme 24/7 is, while at times, hard work also so satisfying and rewarding. I'm so pleased your trip went so well.

Sounds like you had a great time. Glad it went so well.

Wow your trip sounds amazing love all your outfits. (great job on your makeup)

Sound like you had a blast! I wish I had come down to hang out with you (not that far from boston).

I LOVE that shiny top in the very first pic. Where did you pick that up?

Thanks for sharing your cool adventure!

@SometimesSteffi - I might check out some of the CD events. I've ruled out Keystone, because I find some of their sessions very offensive.

@Helen_Highwater - A lot of those things are what I did in Boston - Maybe I didn't elaborate, but I took plenty of subways, did a bunch of everyday things, etc. - and it was all amazing. Even a homeless guy called me "Miss" on the street.

@Connie D50 - Thanks! I stink at makeup but I'm working on it.

@SylphDevine - I tried so hard to find people to meet up with, ahead of the trip. LOL now you tell me. The top was from Amazon. It comes in other colors too: https://www.amazon.com/dp/B0C7G3NBSW/

Sherry Ann

I haven't found any of the sessions offensive, but that is obviously a matter of perspective. There are 8 to 10 different sessions 4 times a day, for 3 days. There must be some that are not offensive. Skip the sessions that offend you and meet some new girls to hang out with at the hotel restaurant, or at any of the restaurants within walking distance.

Steffi, I'll send you a private message.

Sounds like me when I go to Diva Las Vegas. Only drab clothes I have are what I traveled in. It's like living in a fantasy for 5 or 6 days. Shaving every day sucks.

Glad you had a great time. Once you do it (spend several days en femme) you want to do it again soon! I'm practically counting the days to Diva.

Quote:

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Originally Posted by Sometimes Steffi

A transgender conference. for example, First Event (Boston), Fantasia (Provincetown) and Keystone (Harrisburg, PA) should all be within driving distance. Besides the four days and four nights all girl all the time, you will meet many CD/TSs and will travel with "a posse" wherever you go. Plus, you'll get to go to seminars that may be of interest to you. There's a sub-event where you wife can meet oter SOs of CDs. Go to a free clothing exchange to stock up on new outfits.

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Steffi - I tried sending you a private message, but it says: "Sometimes Steffi has exceeded their stored private messages quota and cannot accept further messages until they clear some space."