Sherry Ann's Big Adventure, the Sequel!

Last summer, with my wife's encouragement, I went to Boston and stayed en femme for four days. It was the first time I'd ever been Sherry for more than a single day/night. I had an awesome time! I documented the trip here on the forum: https://www.crossdressers.com/forums...Big-Adventure!.

I love that city (went to grad school there and lived there for several years), so I'm going again next week. I wanted to go four a couple of weeks (can you imagine??) but that did not work out. So I am going from Wednesday through Sunday -- five days this time.

I'm planning to travel dressed (last time I dressed on arrival). Driving, not flying, so there are no security issues. I'll have to make a couple of stops for food, fuel, restroom, etc. but this is the northeast which is all pretty accepting. I feel safe. My first stop on arrival will be to get my nails done. LOL priorities!!

My wife and I went shopping today and I bought a couple of new outfits that I'm looking forward to wearing. :)

I have plans for Wednesday night and most of Saturday (volunteering at Boston Pride). We'll see where life takes me the other days!

I'll post updates and pictures. :)

That is so great, Sherry Ann, I know you will have a fantastic time and am looking forward to reading the story about it.
I remember reading about your trip last year, and went back and read it again just now. Great trip and report.

Staying in girl mode for several days is special, isn't it! After a couple of days, it changes and you start experiencing it all in a different way than you do during a single day of dressing, that's my experience anyway.

Maybe you get to wear more dresses and skirts this time?
Have fun.

I hope you have a great time!

just about every business in New England displays the rainbow flag so you're in pretty safe territory.

Thank you Suzie!

You're so right. After a few days it is hard to explain but you get used to it, and then the contentment is sooo high! Going back to drab is a major downer. Lol also kind of a relief from all that work. But mostly a downer!!

Last time I only wore a dress one day and honestly it didn't fit too well. This time I am packing a skirt for Wednesday evening and my wife helped me pick out a cute long summer dress with an appropriate shirt to wear underneath.

Two things I would love to wear are a miniskirt and short-shorts, in bare legs, but I just don't have the confidence.

Sherry Ann, may we presume that you’re not taking any of “his” clothes with you? I’ve found that having no options to retreat sharpens the focus on the experience. Let the good times roll.

I haven't decided.

Last time, I only had the drab clothes that I wore to drive there (about 5 hours from NJ). When I arrived, I changed in my hotel room and the put the drab clothes back into my car. I figured if I woke up any day during the trip and didn't feel like dressing, it would leave me no choice :) because I'd have to dress up to get back to my car, in which case I'd be dressed anyway!

Also last time, I considered throwing away the only set of drab clothes in which I traveled, but that seemed a bit extreme. It'd be wasting perfectly good clothes and would leave me stranded in the event of some emergency.

This time, I'm thinking of traveling up there already dressed. Which begs the question, do I bring a pair of emergency clothes and just keep them in the car, or not bring them at all? I guess I'm torn between the rational thing and the fun thing. :)

I have spent several days dressed and interacting in the community just doing normal stuff. Shopping is always dangerous to my purse but oh so much fun. Starting the day and then finishing it after a dinner and my be a club for a little music and dancing is just so much fun. One thing I learned is that you need extra time for getting ready to face the world if you are going to blend in. Packing for a several day trip is one of the hardest things I have ever done. Every out fit and occasion has special shoes, Day look and evening looks add up to two outfits per day so a four day trip you end up with 8 outfits which do not fit in a carry on.

A multiple day trip allows you to really immerse yourself into being a woman. You become aware of odd little things such as grates in the sidewalk, or walking on grass in the park. Refining the contents of your purse to address little accidents such as a blister from a high heel. Making sure that you have a couple of extra pairs of nylons and a bottle of clear nail polish to stop a run. The best part of an adventure over several days is that by the end you are so comfortable that you will hate to revert back.

Sherry, That sounds awesome. Have a great time.

Have enjoy the trip, be safe and have fun!

Quote:

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Originally Posted by Sherry Ann Evans

This time, I'm thinking of traveling up there already dressed. Which begs the question, do I bring a pair of emergency clothes and just keep them in the car, or not bring them at all? I guess I'm torn between the rational thing and the fun thing. :)

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Burn the boat. Girl clothes only!

In a real emergency, you can always buy guy clothes.

When I've done girl trips, usually my only guy clothes are workout clothes. More fun to travel without the safety net. You are pot committed, as they say in poker.

Sounds like a great outing coming up Sherry, leave the so called emergency clothes behind remember this a girl trip. Im super jealous of all the ladies on this forum with wives that encourage their husbands Crossdressing adventures. Enjoy

Off I go! Cute new girly sneakers (lavender with pink trim), stretchy jeans butt/hip padding, short-sleeve sweater, breast inserts, freshly washed wig, and makeup almost certainly not as good as it should be. :/ Time to put his wallet stuff into her purse and hit the road...

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Here! I stopped halfway to charge my car. There was a nail salon, so of course I had to go there to pass the time. :) Nice shade of a purpleish-pinkish. I'll post pictures later.

Threw on black faux leather leggings, boots, and a sparkly green shirt. There's a pic of that outfit in the post from last year that I linked above... Wanted to wear w skirt tonight but ran out of time to shave my legs. So another night.

Going to a comedy show now. Maybe I'll meet a nice single guy who is also here for Pride weekend! Lol you never know.

So far everyone I interacted with has been wonderful. The nail tech, hotel clerk, and Uber driver all treated me like a lady. :)

Thanks for sharing

I'm back home, back in drab, back at work, and so on.

It was a great trip!! I was able to wear several different outfits, walks a zillion miles all over Boston and Cambridge (lost two pounds!), got a little better at doing my makeup, and felt perfectly safe and welcomed the whole time. The best part was Pride and related events on Friday night and all day Saturday. In some tiny way, it felt like I was actually making a difference.

Since I didn't bring any boy clothes for the whole five-day trip, I was still dressed when I arrived home last night. My wife and I went to dinner so I could have one last thrill, before un-doing it all and changing back.

I don't have a lot of pictures, unlike last time :( but I have lots of happy memories.

Boston is a FANTASTIC place to be out and dressed up as your authentic self!!

Glad you enjoyed your trip to Boston/Cambridge! I'm originally from Boston's South Shore and have worked in the city during much of my work career. Now retired so I don't get there any more but I miss the great seafood.

Sherry Ann, I am glad you had a great time.

I also want to remind everyone that practice makes perfect! Or at least better!!

A couple of years ago, the concept of getting ready to go out all by myself was an incredibly long and stressful one. I couldn't choose an outfit, the idea of doing my own makeup was foreign, and confidence was something that I had to renew for every outing.

Now I can be fully in guy mode, and out the door feeling good as Sherry Ann, in an hour.