Two week en femme challenge in NYC

[Jackie7]

So here I am in Manhattan on day three of my two-week en femme challenge. Usually when I dress up it is only for the day or evening, and usually I have the pleasure of traveling everywhere with my darling wife. But she's been called to Florida on family business, so I'm here on my own without her protective cover. Plus this business has extended our trip from the planned few days to at least two weeks. Plus we left on Sunday in a bit of a rush and one bag didn't make it into the car: guess which, my guy bag. Most of my clothes are female anyway but it did hold the safety of a couple of dress shirts, a jacket, man shoes and socks. I'd been planning to dress most of the time anyway, now there is no choice, which is what makes it a challenge. Does she have enough girl stuff for a two week ride? Well there are lots of stores in Manhattan. Can she do it full time without freaking out? It will be my longest ever unbroken stretch. But I have to say, I'm feeling very girly, very comfortable, and so far it's going very well.

I had a great time Sunday night, at the Slipper Room with my wife (she didn't fly south until Monday morning) for a burlesque show. I wore jeans with a pretty top, boobs and my best wig, low heels. Chatted easily with other patrons, one nice gentleman even fetched us drinks. Yesterday after seeing my wife off to the airport I went out shopping by myself, then met our best girlfriend Patty the retired fashion model for drinks, early dinner, and a long stroll around the lower east side. That's Patty in the pic and I have her ok to post. Today I will take the bus uptown to the upper east side for lunch with another girlfriend and maybe a museum.

I've been going out for more than fifteen years, but never full time for a stretch as long as this, and rarely alone without my (fully participating) wife. I'd been wanting to test my commitment to dressing as a woman, to sneak up on the big question, do I want to go full time? I'm retired so if it really is what I want to do, I can. So here we are, can I dress full time, or will I chicken out and hide in the apartment or go buy some guy clothes when it all becomes too much? I'll let y'all know in about a week. So far the girl is on top.

[Amy Fakley]

Sounds like a challenge you're up to, Jackie!
So jealous ... 2 weeks on your own in girl mode in nyc???!!! :-)
Call me crazy, but I think you're gonna have the time of your life!!

[bridget thronton]

I hope the experiment works out for the best

[AnneC]

Good luck and hope you have a great time. I would love to try your challenge myself one day. Have fun!

[CONSUELO]

You are looking very good and clearly enjoying yourself. Keep us posted on what happens to you over the next week. i suspect that after this experience you will just go en femme completely.

[Amy Lynn3]

I envy you....Just to be in Manhattan for two weeks is something I can only hope for and to be dressed is over the top. My Manhattan trip was only four days.

[Julie Denier]

Looks like you're off to a great start! Can't wait to hear more ... ;)

[StacyCD]

That's one of my fantasies! My SO would, however, probably never come with me!

[MonctonGirl]

Sounds amazing...
If only I had enough clothes and TIME to do 2 weeks en-femme.

Truly I don't think I could do 2 weeks let alone 24 hours of sitting to pee.

[Jaylyn]

Would be tough on me to do two weeks let alone two days.... I have to many chores out on the farm and there's no way I'm gonna ruin a good outfit out in the pasture.... Lol

[Stephanie Julianna]

Jealous! Jealous! Jealous! Did I already say that I'm JEALOUS?

[Martina]

Now that's a good way of getting to dress and no male clothes, I hope that you have a great time and make the most of your holiday.

Martina

[Beverley Sims]

Jackie,
Enjoy the moment you will find it all too short and just a memory.
New Yorkers on that island are all too busy to notice the likes of you and I.

[charlenesomeone]

Looks like a great time in the big Apple.
You look great and very comfortable. Keep the updates coming.
We are cheering for you.

[Marcelle]

Hi Jackie . . . did the bag of guy clothes really get accidently left behind??? :) Seriously though, you look great and seem to be having a great time . . . Good luck and keep us updated.

Hugs

Isha

[Sarina Curtis]

Best of luck with the 2 week challenge Jackie and I hope it helps you reach a decision. You look great!

Sarina

[Tina B.]

Now that's the way to take Manhattan!

[Jackie7]

Oh dear I meant to post a diary but have been entirely too busy running around Manhattan. I’ll try to catch up over the next couple of days.
day 3 Tuesday
--Wore skinny black jeans over padded pantyhose made of foam rubber following docrobbysherry’s advice from this site. Wow, a tailored, realistic and low-budget butt over my skinny old-man ass! Red-and-black top borrowed from my wife, red leather jacket we bought in Las Vegas, curly shortish wig, black slip-ons with 2-inch heel. Close shave (white whiskers) with very light makeup – just eyes, lipstick, dab of powder. Trying hard to dress my age but not frumpy. I hoped I looked good, I felt great. I really must get a girly pair of glasses.

--Out all day, First Avenue bus uptown, girlfriends for lunch and thrift-shopping, bus back to Union Square to visit an 81-year-old lady for drinks and dinner, her choice: elegant Spanish restaurant in Greenwich Village. Got in about 11.

--On the street and on the bus and at the coffee bar, nobody looked twice at a homely middle-aged lady who is not dressed to stand out but to blend. She attracts no more attention than any other middle-aged lady, not even when she forgets and walks from her shoulders like a man.

--Good-fitting girl-weight mid-heel (2inch) walking shoes encourage a ladylike gait that leads from the hips. These shoes are great on pavement, today I walked about 40 Manhattan blocks.

--My friends said the padded panty enhanced my look but did it make any difference on the street? I don’t think so. Not because I looked any better or worse, but because, once you get comfortable in your girl disguise, nobody pays any attention to you. You don’t stand out, you’re just another person in the crowd, in my case too old and homely to be of sexual interest, so filling space but functionally invisible.

--the padded pantyhose plus wig is very hot indoors in NYC autumn, beautiful day today but always warm indoors. I guess it is like hot flashes– I wanted a hand fan.

--typing with stick-on nails (French polish natural color) is a bitch with gnarly, work-hardened fingers like mine, impossible on a phone. Lost one nail today, right middle finger.

[Bria]

You look great, have fun!

Hugs, Bria

[Jennifer-GWN]

I'd love to be there as well. Sounds like a marvelous time.

Cheers... Jennifer

[Janine cd]

I envy you. I was in Manhattan about a month ago and I'm familiar with all of the places that you visited. I would love to have been there with you dressed as well.

[Julie Denier]

Thanks for the details! Keep it up -- we'll be watching ;)

[Paula_56]

you look like a cis gendered woman

[Jackie7]

you look like a cis gendered woman

Thanks Paula so do you! Enjoyed your T or Tea report, I lived in the UK for two years in the early 90s, but was completely closeted then, always wanted to go out en femme in London but never did.

[bridget thronton]

Thanks for the update - you look like you are having fun

[Jackie7]

Day 4 Wednesday
--I lost confidence in my suitcase wardrobe and in my ability to assemble a coherent outfit. I tried on everything, it was all awful, and almost decided not to go out. But get back on the horse, girl. I reassembled a basic outfit I knew had worked, the black skinny jeans and black top, red leather jacket, silver jewelry, and went for a very long walk thorough the East Village and Lower East Side. Met a guy friend for a drink and a bite at an esoteric museum.
--Walked slowly home on shopping streets but not really shopping. Thinking rather: when you blend into the crowd, then crossdressing has no outside audience, it’s just your clothes and inside them, just you. So it comes back to that: what pleases you.
--Shaved twice today. Shaving and makeup every day is a real bother.

Day 5 Thursday
--Office girl here at the apartment, charcoal dress with empire waist, patent heels. Out for a walk in the morning by myself, worked here all afternoon with a client to whom I’m long-ago out, then walked again with her for tea and a snack.
--Lost two more stick-on nails, peeled them all off.
--Boo hoo had to change en drab for a business evening (I found an old dress shirt and beat-up black sneakers). But even as a dude I am under-dressed frilly. Nobody looks twice at middle-aged man either.
--I’m loving my bras and breast forms. I’ve been wearing them to sleep, something I never do at home because the princess prefers skin all over.
--Lately, restaurants in the east and west village seem mostly to have unisex restrooms.

Day 6 Friday
--Red jeans with red-and-black top, men’s leather coat, red scarf. Padded pantyhose for warmth as well as form in 40-degree weather, breezy, bright and clear. Out early with a girlfriend for coffee and wrangling cars before the 11 am deadline, she drives away, me to double-park for street sweeping. But I got the prize, a nearby parking spot where I can stay until next Tuesday.
--Morning errands on walkabout around Tompkins Square, manicure (pink) on Avenue A, pick up laundry, buy bread and bananas, make lunch.
--Change clothes for afternoon, purple knit dress with a black slip, and stroll crosstown to the Bowery to Tatyana, formerly Bettie Page, my absolute all-time favorite dress shop. Usually I shop with my wife and/or a girlfriend, but I’m alone today and the store is not busy afternoons, I’m wearing forms and hip pads, I can try on everything. And take pix of everything too. I bought a crinoline, and put a coat and a dress on hold to discuss with the princess.
--My walking stride becomes more relaxed and easy, I’m moving easily from the hips instead of from my shoulders. It feels like a significant shift. I should be doing yoga. Home early and crash early, whoof, a lotta walking.
--Should have had a pedi with that mani because a sharp corner on my littlest left toe cut into the next toe, a mess that hurts. For want of a nail the kingdom was lost…

Day 7 Saturday.
--By now it feels almost natural to shave close and do makeup before dressing in the morning. Just what I do, every day.
--Charcoal office-girl dress with empire waist and a pink ribbon, black crochet shrug. The docrobbysherry foam pads slide down a bit under the slip, they seem to need jeans to keep them in place, or else more robust hose than I’ve got right now.
--With my wife out of town for the week, I’ve been making dates with our various girlfriends, but not for today. So off I go myself to the museum at the Fashion Institute of Technology, must catch the last day of their History of Lingerie exhibition, which was terrific, and also Dance into Fashion, which was so lovely I almost cried. It’s there until January for anyone visiting NYC.
--Shopping on 7th Avenue, 14th Street, and lower Broadway. Tried on boots, tried on tops, tried on girly glasses, bought Spanx that might hold the pads better, ended up back at Tatyana and bought the dress.
-- I got invited to a late party tonight. Gonna wear my new dress, it's tan with dots and magenta trim, scoop neckline.
--The two-week challenge continues tomorrow when my wife returns. I will be so glad to see her, to have her protective cover, and her fashion advice!

[Julie Denier]

Thanks for the status report! Love all the details - really makes you remember that a lot of things many of us consider to be fun are really a lot of work when you have to do them every day. Keep up the good work ;)

[Beverley Sims]

Jackie,
You seem to be doing well and the cold feet syndrome will creep in, but, stay on the bike and don't fall off.
As long as no one bothers you it should be free sailing.
I went and looked at the Exposed exhibit, I was looking for lots of fashion shots, but interesting anyway.

[ChristinaK]

What a dream come true. You are soon lucky!

[CindyR]

Jackie, very encouraging, I have been following since you started. I am nowhere near ready to go out, but I was thinking NYC would be the place, not far for me, and people don't give a second look.

Keep it up and enjoy!

[Jillian Faith]

Jackie thanks for letting the rest of us live vicariously through your two weeks enfemme in NYC! Keep the pictures of your daily outfits coming.

[Marcelle]

Hi Jackie,

Thanks for the update . . . I think you are pulling your outfits off quite well. Keep going . . . halfway there! :cheer:

Hugs

Isha

[S. Lisa Smith]

Sounds like a great time to me!!!

[Tina B.]

You are looking great, and it sounds like a dream vacation to me!

[bridget thronton]

Very nice dresses in your pics thanks for sharing your journey these two weeks