The most daring

[MonicaPVD]

For those of us who are part time dressers, what's the most daring or extreme (PG-13) thing you have done in public while dressed?

[Teresa]

Monica,
While I was part time it's hard to say what was the most daring as every step felt daring at the time .

Looking back was it was possibly more in private when I took my first photographs . Then it was my first drive , or buying my first shoes or venturing out to get my skin colour checked for makeup ?

Or could it be when I jumped in my car for the first time in a ballgown to visit my first social function in an open hotel ?

As I say the list goes on as we progress .

Is it daring for me now ? Well not anymore because I've left the man behind , I feel once you accept that it's no longer a series of dares , it's my life .

[Diane426]

I think for me it's just being in a mall properly dressed and feeling totally feminine.

[MilenaSometimes190]

Guess going out with feminine underwear under my male clothing.

[JennyMay]

For me, at the moment, it is taking part in a support group Zoom meeting. I?m looking forward to going to a meeting when it is (COVID) safe to do so. It will be a big step for me.

[Samm]

Going out alone for the first time, which was also my first time to a night club in girl mode. Yikes!

[Krisi]

Walking downtown in public and walking through the mall (and getting stopped by one of those sales guys in the kiosk trying to sell some sort of skin tightener). The worst part is when someone speaks to you and you have to answer back.

Of course, to do any of this I have to drive. Driving is fine but once I almost hit a bicyclist riding on the wrong side of the road at night. That would have been a mess.

[Rikidee]

Attended a lingerie party that was sponsored by a lingerie store. There were about a dozen GGs there. The hostess knew me, if anyone else knew I was not a real girl they did not let on. We laughed, talked and played games for a couple of hours. It was a lot of fun.

[jessica33]

During this pandemic lockdown I went to office as Jessica .

[AngelaYVR]

I would have to say that all the things I did that felt daring at the time now just feel normal. Some of those things were driving across Vancouver Island and taking a ferry, retrieving my car that had been towed (never a pleasant experience) and performing on stage at amateur drag night.

[Helen_Highwater]

There's a few that might possibly qualify. Using a ladies public toilet for the first time as well as walking into the female changing room with 3 items while enfemme. Using public transport is another as you're sort of trapped there sitting next to folks shoulder to shoulder.

I still think however for me at least the first time I went shopping enfemme would top the list. Exiting the car, putting on my coat, straightening my hair, grabbing my handbag, remembering to lock the car as I walked way across a busy car park and over the threshold of the shop door way I felt a bit like a rabbit in headlights. Thankfully the butterflies, that had felt like eagles, soon landed and I realised that all those good folk who'd said you'll be fine, just do it were right. Which is why those in the first paragraph were just that bit easier to do as the hard bit had been done.

Just thought of another; while killing time waiting for a train going into a city centre non gay, not obviously LGBT friendly pub for a glass of wine. Standing at the bar I did feel somewhat exposed but hey I survived

[UsuallyRick]

It is an ongoing list of most daring events.. first was just wearing stuff in privacy of home, then venturing around our rural home.. went out on Halloween with wife and kids to local fire station for community fun spot and kids trick or treating,running into people we knew was a trip.. I was dressed as Lita Ford and tried to get wife to go as Ozzy🤣.. no go.. a grocery shopping trip(s) while family was out of town for several days was fun, along with dress shopping at local WalMart and trying on several dresses and purchasing a dress and some panties.. another was the goodwill store in man mode scooping up dresses and hitting the changing room, that was fun! Got some looks and help/tips from S/A!! It's been mostly subdued for the last year but this ski season I go full girl mode minus makeup under my uniform (ski pants as I work outside all winter) and lately because my normal ski pants are hot pink I have been wearing my favorite Obermayer pants for work as a statement to management that we are short on uniforms and the ones we have are at least 15yrs old so time for them to supply new ones or we will just wear whatever and not look professional as a team... I have been wearing my fuzzy hot pink zebra striped PJs around house and outside a lot and even in public occasionally, I love it!! Can't wait to get fully done up again and go out some more..

[Lori Ann Westlake]

I'm not very daring, and I've rarely been out. I guess the most daring thing I ever did was to go through a grocery store checkout alone, hoping I wouldn't be asked a question, knowing my voice would give me away if I answered.

[Rachel M]

So I order two bras online from Soma with an in store pick up. I showed up early in guy mode to look at them on the rack. The SA asked what size I needed. I didn’t disclose I ordered already. So I’m looking at this bra with doubt it’s not gonna fit in the cups. I look up at the SA and tell her I am actually shopping for myself and asked if it would be okay to try it on. She paused for a moment and the said yes. I told her this is my first time in their store so I wasn’t sure between a 38 or 40 bandwidth. She grabbed both and took me back to a fitting room. She left me to try them on. She came back to check on me and the fit. We were talking over the door then I asked if I could just show her and opened the door. She saw what I was working with and we to get me a smaller cup size. I tried that one as well and didn’t like the fit and redressed. Back out on the floor, I told the SA I was there to pick up my order, but no longer needed it because of the fit. The other SA overheard and was preparing my order so she picked up in helping me. She was able to cancel my order without my card ever getting charged. I asked if they get other men shopping for themselves as I just did and she said yes they do. Great customer service. I think what helped was I kept my mask up the entire time.
Rachel

[MsEva]

For me it was driving en femme from my home in VA to PA some 7 hours away. I have done this quite a few times, but have not had the opportunity since my parents passed away some ten years ago. It was always a thrill to make the long drive just as an female on the road.

[Kirsty2907]

For those of you who have ventured out (I tip my hat to you, obviously Prada or something) 😂

The most daring I have ever been is wearing tights under trousers, or twice in the dark of night I?ve ventured out to my back garden bins... 🤷🏻*♀️

Think I should rename myself lamely lamerson

[candykowal]

I suppose going to a new high school for my senior year and being able to present as the girl (I was living as Candice the whole summer) it was a bit un-nerving.
I was very afraid I was going to be bullied and beatin up my first day. I happened a lot at my old school presenting as a boy.
Those of you who remember High School in 1979, everyone...boys and girls, had long hair and wore jeans, so I fit in pretty well.
There were days I longed to wear a skirt and when I did, I got teased a lot by the girls and they would pull on it or hike it up and tease me.
The girls that be-friended me were more of a worry then the guys. The experiences I learned that year would carry through to college.

[Stephanie47]

For me, the most daring was actually getting totally dolled up on Halloween and buying doughnuts at a Winchell's Doughnut House. I had on full makeup including nail polish, a blond wig, jade green and black dress, and hosiery and heels. Underneath was all the proper undergarments; bra, slip and panty. The counter woman gave me a compliment. With some hindsight and reflection I wonder why my wife did not confront me when I came back into the house. She had to know I was gone and feinted sleeping. Getting ready and leaving had to be more daring than actually buying the doughnuts.

[Sandi Beech]

Monica

So as of yet, I guess my wildest thing to date is wearing nothing but lingerie into a bar - more than once I might add.

There is a picture in one of my posts labeled- Maybe I am crazy.

Let me just say I needed a drink to relax when wearing just a black maidenform slip, bra, black thigh highs and to top it off, black leather collar and cuffs. I got hit on by a young couple in just a few minutes so that was also crazy.

I have worn a few variations of the same thing, and the Halloween before covid was the last time. I also had chains attaching my neck collar to wrists. The following night I went to the same bar and the bartender says - I saw you dancing last night. The attention is addictive and I found people were definitely looking. One guy wanted to know if I would go out to dinner with him wearing that. I was like , no way, I live here and likely to see someone I know.

So Monica - you going to tell us your wild adventures? Haha.

Sandi

[Alice Torn]

My first night time out dressed, i drove around a small town late, and parked and walked around, then got back in the car, and drove back to a town where i had a motel room. and on the way, the local cop pulled me over. It all went fine, He just wanted to know what i was doing walking around a town late, when everything was closed and why my driving was erratic. No ticket. The next day, strutted around another bigger town in a mini dress, dark hose and heel. and was noticed and shouted at, by guys in a truck, and teens. Later in the day, went to a big city, parked and strutted, and got asked for a jump start, by a man with his family, who he told not to watch!! Gave him jump. and he thanked me. Another time, went waliking around a university campus park, and forgot to zip the back zipper on the dress, all the way up. It was only half zipped up, and i wondered why a girl was watching me, from the other side of the road, and laughed. Later, when i tok a back photo, i saw the back of the bra staring back at me!

[MonicaPVD]

These are all wonderful experiences and a good cross section of our diverse circumstances. Over the years, I have had different opportunities to do outrageous things, ranging from silly to obscene. However, I must admit that the most extreme thing that I have ever done is to go on a date with a guy who insisted on me wearing a very inappropriate outfit for the occasion. He basically picked out the outfit for me. This meant that the whole night all eyes were on me and, trust me, they were looks of disgust and disapproval. My gentleman friend really enjoyed watching everyone's reaction. He had a great time. To clarify, we went to dinner at a very fancy restaurant and then to watch a play. I was wearing a way too small, and too tight, minidress with 5" heels, fishnet stockings and almost-Halloween-calibre makeup. I looked completely ridiculous and out of place. It was embarrassing for the first 20 minutes and then the rest of the night was like a comedy sketch.

[Karren H]

I don't know.... even though I've done a lot of things enfemme.... going to Casino's dresses, getting trapped in the rest area ladies restroom on the intestate by a woman and her brood of female children and a pregnant woman throwng up in the next stall (almost had my skirt sucked down the toilet too...), drove on long business trips dressed, checked into and out of hotels dressed.. walked around an number of cities enfemme... did many quick gender changes in the family restrooms on freeway rest areas (walk in male and come out female)... Shopping in malls.. shopping in consignment shops... shopping shopping shopping enfemme. And I think that doing any of those things for the first time was daring and extremely exciting!

The first time I left the house dressed I was 14 and had dressed in the basement when everyone was asleep. All my mother clothes (bra stuffed with socks, girdle, nylons, shoes, skirt and blouse) that I had stashed in an old cistern... but I had no wig so I took a hair net and placed a ton of curlers in it to give the appearance of having my hair set. Snuck up the outside stairway into a cold clear moon lit night. Remember shaking and shivering from the excitement. We lived in a small farming village in Southern Michigan and getting caught would have been devastating. So I took a walk around the block and as I rounded the last corner heading back towards the house, I could see a car's headlights coming up from behind me. I took of running down the street then cut through the neighbors yard, curlers flying and half tripping over my skirt. Made it back home but must have broken every world record that night but no one was watching to record it! None that I knew about! lol

[MissSixties]

Going to a gay bar a few times and getting hit on, kissed deeply in public a few times one wanted to catch a Uber to his motel in town and have his way with me but sadly in hindsight i declined, havent been since COVID unfortunately

[beccadeath]

If I'm honest? Putting in homemade breast forms for the first time in front of my wife...

She's aware and accepting and all, I'm just very repressed.

[TheHiddenMe]

Going to see U2 at an indoor arena with about 15,000 fans by myself (and taking public transit to attend). Second was probably seeing Hamilton in Chicago (also solo).

[Beverley Sims]

When I was part time, dress shopping with a group of girls on a Saturday morning, for a dress to wear that evening.

The evening escapades got daring as well. :-)

[Ressie]

Each of the few times that I've gone out dressed alone were daring. Especially my first time out in 2012 - was at a gay bar having a TG weekend event. I got out of the car with butterflies in stomach, walked into the place and I was the only CD there. Since it was in the afternoon hardly anyone was there but I felt very out of place and awkward to say the least!

Going out with a small group of CD friends is much easier :)

[cosmolovesph]

Gone out fully dressed many times, but one of the more daring have been going to a movie fully dressed (not uncommon for me) and in my purse I brought a pair of handcuffs. Once the lights dimmed down I then clicked on the cuffs with my hands in my lap (not behind my back or to the chair, nothing that crazy). Fun right?

The first time was quite the thrill but the second time I decided to leave the key in the car.. Thankfully I thought ahead and brought a jacket to carry over my hands to hide the cuffs for the walk back to the car made it more stealthy but what a thrill! I'd love to take my shackles but between the noise and getting out of the theater... I won't be pushing my luck any further.

[MonicaPVD]

Ressie, I totally hear you. Going out alone is terrifying at first. Then you go to a supposedly welcoming place, such as a gay bar, and you find yourself all alone there, as well. It is intimidating. I have found that as my confidence grew to face the world as Monica, this has also made me a more confident and assertive person in my vanilla life.

[jacques]

hello Monica,
Once ( when I was under-dressed) in my favourite noisy cafe my trousers slipped down revealing my black pantyhose - the cafe went quiet! Luckily my wife did not notice, but we do have a new favourite cafe now.
I am not sure if this counts as daring as it was not planned - honestly!
luv J

[patti.jean]

Yes, the first time at the Dunes was the same for me. I now have been going to the Dunes for several years am now a welcomed regular. I do appreciate the wonderful people like yourself that have made it easier for so many. Thank you!

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Each of the few times that I've gone out dressed alone were daring. Especially my first time out in 2012 - was at a gay bar having a TG weekend event. I got out of the car with butterflies in stomach, walked into the place and I was the only CD there. Since it was in the afternoon hardly anyone was there but I felt very out of place and awkward to say the least!

Going out with a small group of CD friends is much easier :)

[docrobbysherry]

While Sherry's appeared a number places where my heart was racing at 200 beats a minute? :eek:

I think I most freaked out in Cambodia. A country with a repressive govt. Where I was all alone and hid from the guards while I changed into my Loa Croft, Tomb Raider outfit in Angkor Wat for photos!
If nothing else, I was breaking the rule that women r not allowed into the ruins with uncovered arms and legs!:eek:

A nice couple walking by took this photo with my camera!:thumbsup:
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[Lana Mae]

When I was part time, the first time to the mall alone to the MAC counter for a color check! Sitting in the big chair for all to view! Risky to me but turned out to be a non-event! No one paid any attention to me in any negative way! Not too wild, but it really pushed the limits for me! Hugs Lana Mae

[Jillcder]

Wow Karren great story the curlers flying made me laugh! Also I bet you are the only one on this site to keep your stash in a cistern.

[Frannie7]

Probably the 2 most daring things were going to Stratford, ON (theatre festival town) to see a musical. It was Rocky Horror Picture Show live--I was dressed "normally" not as a character in the show. Also went to a performance of Elf the musical. That was a bit more nerve wracking as there were a number of kids there. Both times by myself.

[prene]

I was in Las Vegas Outlet mall. I was dressed in gg jeans, a nice top with my 36C attached forms and a nice Jean jacket to cover.
I walked the mall and no one cared. I went into a lingerie shop and tried on a few bras and bought one.
I was surprised how easy it felt and was.

[kayegirl]

Attending a school reunion meeting in full enfemme mode. Didn't stay long, just not my thing, hate it when everybody tries to out boast each other with their earnings/achievements etc. Can't even say that I recognised anybody at all.
Why was it daring. The school that I attended was an all boys school, ano just one female teacher. Hated every minute of it.

[Karren H]

Wow Karren great story the curlers flying made me laugh! Also I bet you are the only one on this site to keep your stash in a cistern.

Lucky it was an old dry cistern with no easy access! Located in the basement under the kitchen. Next to the old coal bin.

[Natalie5004]

I had a very nice trip to Target where I dropped $200 on womans clothes and make up. That was fun.

Also my wife came home unexpectedly last week. I did not know that I could move that fast into the bathroom across the house.

At some point I will just walk out as Natalie and be done with it.

[MonicaPVD]

Sherry, I think you won top prize. Wow.

[Teresa]

Kaye,
Old school reunions could be interesting , I also attended an all boys school , I might give a reunion a go when lockdown ends , it might be interesting to see if any others have transitioned . Even more so if any of the teachers have !

[BrendaPDX]

Wow! Tough crowed to compete with. Mine is just getting outside and taking pictures of myself in a park, like my avatar. I have had a few more pictures, shorter skirt, bigger breast forms, but never higher heals. LOL

[Julie MA]

Went to the D--k Dock in Provincetown MA.

[Cass42]

When I was part time at age 21,decided to go out with friends wearing a sexy black dress with thigh high stockings and 4 inch heels.I was also showing good cleavage as well.Was dressed wearing 5 inch hoop earrings too including my hair done.I had a couple men hit on me and told them no way.

[alwayshave]

I new a bartender from a bar that my wife and I frequent. She also works in a hotel bar several nights a week. I was at girls meetup not far from her hotel bar, went in after my meet up with a few other girls. Ordered a drink from her, she never figured it was me.

[Terrihoney]

The most daring exploits are each time we push our confidence to new adventures. My most daring adventure will be tested again this weekend. I've joined a senior woman's only social group, whose name I should not divulge. For two years now, over several meetings, I am assumed as a genetic female to all the members present. Mind you, I'm not accepted as a CD, but a genetic woman. Their by-laws don't allow anyone but real women.
Someday, they might figure me out. In the mean time, I'm actually experiencing life in the female world.

Hugs, Terri

[Marguarite]

About 5 years ago, between Christmas and New Years, my wife and I visited an outdoor Shopping Mall. She let go dressed for the day, wig, forms, makeup, sweater dress, and my new boots (her XMass gift to Marguarite). We took her wheelchair, knowing she wouldn't be strong enough to last long. It was an incredible day, pushing her through all the shops, interacting with all salespeople. It became exciting when after a couple of hours she needed to use the ladies room. There was a large pavilion in the center of all the shops. When we got there I pushed right into the Ladies Room, past a long line that waved right down to the Handicapped stalls. We both used the facilities, freshened up and went back out thanking everyone for their thoughtfulness. That was the first time I used the ladies in public, it was also the first time I did not just feel like a MIAD.

[Leslie Mary S]

For me it was getting fully made up and dressed in Panty-hose, a floral peasant top with bra and forms, metallic blue mini-skirt, 1.5 " black pumps, and a long blonde wig, walking down the exposed 35' sidewalk out to my car. Drove 17 miles to a local gay bar, went in with my purse and camera. Paid the $5 gate fee. Found a table and then took, with their permission, photos of the Drag Queens as they performed,
Drove part-way home and stopped at a fuel station, got out and pumped a full tank of fuel, paid cash at the window, then moved over to the fast food drive-thru for a burger, then drove home and walked back up the 35' walk and into the house. As I walked up and down the 35' walk the security lights automatically came on.
Here is a recreation of that night. The main differences are that this is a short wig and taller heels, and 5 years later.


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[HollyCD]

Many years ago before cell phones and digital cameras (and I was young) I was perusing a department store a bit over an hour from home while wearing leggings and a short pullover. A young mom came in with her two preschool daughters after what must have been dance class, as all three were wearing matching leotards, tights, and crop t-shirt. Made a conscious effort to be respectful and not stare, but dang the mom was super cute, think Stevie Nicks in her late 20's. Feeling inspired on my next trip to a city a couple hours from home, I layered up two pairs of Capizio nude bodystocking, black leotard, fitted crop top in light gray, and black ladies walking shoes. Went in and walked around a couple stores, and a short paved but slightly wooded trail in a nearby city park. Pretty sure I didn't remind anyone of Stevie Nicks, but it was quite the adrenaline rush. A few more outings similar but toned it down a bit, black lycra volleyball shorts in place of the leotard.

[Genifer Teal]

I drove into nyc to go to my first gurls party the weekend after 9/11. Hour delay at the bridge. Soldiers with guns out checking every car. I didn't even get my window rolled all the way down to see what he wanted and he already waved me on. No trouble there. Great party met old and new friends and continued to go out in the city for years afterwards almost every weekend.

[Sometimes Steffi]

I did a lot of things that were a stretch for me. But, I think the biggest one was when I kissed a girl, and I liked it.

I was at the Keystone Conference at the Saturday night Gala Ball. I was wearing a sequined cocktail dress with all the fixings. This (CD) girl asked me to dance, and we ended up dancing the rest of the night together. After the dance was over, everyone was headed to the elevators to go to the bar or back to their room. Just as we got to the elevator, this girl I was with said, "I wasn't going to take my panties off for you, but I would have liked a kiss." How's that for a pickup line? Without even thinking about it, I replied "A kiss, I can do a kiss." Then, she came up to me and gave me a kiss on the lips. She turned to leave, but came right back for another kiss, and then another and another. And, that quickly, I was making out with another girl right next to the elevator while all the other girls were just walking right past us.

I guess I liked it, because I just grabbed her hand and said, "Not here." I led her through the outside door that lead to the parking lot. We were making out right outside the back door to the hotel. We must of made out for about 15 minutes, and it got into some heavy petting. She slipped her hands under my dress and grabbed my butt. Then ... Wait. Wait. Why am I telling you this. Good girls don't tell, and I was a very good girl. I've got nothing else to say. Forget everything that I said.

[MonicaPVD]

Steffi, you're going to get yourself banned from this sequined sanhedrin of ours. 🤣

[Sometimes Steffi]

Oh, did I do bad. I thought it was pretty clean, but I can edit it or delete. I didn't intend to go against the rules.

[Sandi Beech]

Haha, funny.
I actually have an R rated story but left it out since Monica said to keep it PG-13.

; )

Sandi

[Sallee]

I went to the Costco Food court. NO problems at all. And I have gone to many womens dept dressing rooms to try things on Again no problems. Years ago when I was a young good looking CD I went to a straight bar near my college which had a band, Bar tender asked if I want a drink ordered a beer then as I was standing there someone asked me to dance WOW I declined. He turned away disappointed. Really I have never had a problem in most situations. Its just getting the nerve and dressings appropriately
I still want to get the nerve to go to a casino. I guess my biggest fear is that I would win big and get noticed because of my big win LOL

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that was very gutsy If caught you might still be there

[lingerieLiz]

Went to a drive-in with a friend for a rock n role contest. I was the girl. My sisters had taught me to dance as a girl. I was young and passed at the time.
as

I went to a costume party as a nurse. I wore a white nylon nurses' uniform dress which were popular at the time it showed my nylon slip with a lace bodice, lace bra, panties, garter belt white stockings and white nurses heels. Wore a nice wig and nurses cap. Got hit on by a couple guys. Some of the girls came up and said, you have been practicing. One suggested we get together.

I've been an adventurer all my life.

[Misty_cder]

My most daring was when I wore women's jeans with 2-inch block heel boots to fill up gas late one evening. I had the jeans over the boots, was wearing a gaff to get the smooth look, and had on a regular men's polo shirt. This was my only time out openly wearing woman's clothing.

[Vintage4sarah]

Back in 2013, I remember a special autumn afternoon and evening when Sarah would find the courage to do three new things for the first time. I was away on a trip a day early to give one of my historical battlefield tours and booked a motel room. It would have been a usual night for Sarah in the room, but this time I explored new activities. The first was meeting and chatting with a local crossdresser I met on the net earlier. He was on the way home from work (dressed as a guy) while I was all done up as Sarah. Just some innocent chatting and photo swapping before he had to leave. The second was my first attempt at going out as Sarah for a stroll and do some window shopping of the downtown area. I would then go to get some "take out" for my evening meal. Everything I did that night was new and far easier than I thought it would be! Finally, I knew that I could pull this all off with ease even though, my inside was all butterflies at first.

[Jennifer_Ph]

A bikini in public. Was so fun.

[cdinmd206]

My first time going out fully dressed was at Halloween and going out as a french maid to a CD friendly bar in Washington DC, but my most daring happened by accident. A couple I knew who also knew I cross dressed asked if I wanted to go to the gay pride day in Washington DC. I said sure and the wife said I should fully dress. I dressed but that was back in my dress like a days and I wore and extremely short skirt with my usual stockings, garter belt and panties under it. Blouse with my big boob forms and a long blond wig plus heels. I thought we were going to drive to the area of the festivities and park close by. When I got to the couples house I found out the plans were to drive to one of the DC metro stations and take the metro in. I had never been in public fully dressed in daylight and had never thought about using public transportation. When we boarded the Metro train I was as nervous as a nun in a house. We had the metro car to ourselves until the first stop and a black family got on. The mother looked me over and said nice legs and the teen daughter piped up and said look mom he is wearing stockings and garters. I was ready to climb under the seat, but the mother quickly said you must be going to gay pride day. We had an interesting conversation the rest of the trip and I had a wonderful day walking around in public in the daylight for the first time. Attached is a pic of that day. The lady os the wife of the couple I went with.

[kimdl93]

I have never done anything that wasn?t G rated in public. The thing I found most challenging personally was attending a business meeting with a GG colleague in girl mode without giving any advance notice. It was a bit impulsive, as I had made the appointment to meet with her without any prior consideration. When the day came, I realized I had scheduled a mani-pedi just a couple hours before our meeting and found I just couldn?t bring myself to wreck my nails or change back into male mode.

[ColleenA]

The most daring exploits are each time we push our confidence to new adventures.

That, to me, sums it all up.
For decades (literally), I could never imagine being en femme out in public, mainly because I cannot pass under even the lightest scrutiny. The most I would do was stand out on my front step around midnight and breathe in the fresh air.

In 2015, though, I decided to really give it a try - under the "protection" of Halloween. Actually, I went out on the 30th and 31st (a Friday and Saturday) to Kohl's at about 9p.m., when it was dark out and fewer people should be at the store. Still, the chance to be out and to simply browse through all the clothing - especially the lingerie section - without worrying that somebody would peg me as a perv was both mind-blowing and liberating. (I did take the precaution of keeping my distance from any other woman in the area.) I did not buy anything either night. Also, the first night, my gf went with me, and we stopped at Denny's after leaving Kohl's. The second night I did my first solo outing.

The next year, I again did two evening shopping trips, but this time I bought two dresses. A woman buying dresses? Whoa! Stop the presses! For me, though, this average event was another huge first. And I felt bolder; the day AFTER Halloween, I ran errands in the daytime with my gf. We ate lunch at a restaurant, picked up some items at a pet store, then went to Kohl's, where I bought a pretty pair of panties. Without the protection of "it's a costume," I did get a couple of dirty looks, but I held my head up and went about my business.

Now I try to take off the 29th through 31st from work each year to have whole days out. One small benefit is I can leave my nail polish on for three days in a row. My most common activity is shopping. I will go to Macy's, Nordstrom Rack, and other department stores (some have enormous clearance sections), as well as thrift stores. I have bought skirts and blouses, makeup and shoes, panties and bras. Other activities have included normal, daily stuff - lunching at a diner, hitting the grocery store, and picking up a prescription at Target.

If you have never gone out en femme, believe me when I say it is amazing how much little things can boost your self-esteem. The first time having someone call me "ma'am" or overhearing the word "she" applied to me sent a thrill through my body - it is so validating. One time, a woman caught my eye as we passed; at first she just smiled, but then she stopped to compliment me on how I looked (ok, she clocked me and kindly gave me encouragement). Often, though, store clerks interact with me as they would with any other woman, despite my "knowing" I am not passing. Each year, I have to work at setting that mental block aside.

One funny moment was when I was at a mall and asked to have a skirt held for me while I continued on to other stores. The lady asked me what name to hold it under. I stood like a deer in headlights. It took at least 6 seconds before I stammered out "Colleen;" that is an eternity for such an innocuous question.

Other milestones: 2017 - first time in the women's dressing room (exhilirating).
2019 - ONLY time in the ladies' room (too stressful; will stick to gender-neutral restrooms, such as at Target). First mani-pedi (awesome). This year, I again went out after Halloween - this time on Nov. 4 for a bra sale at Sears that I had passed up days earlier.
2020 - besides looking through the lingerie sections of department stores, this year I was at an outlet mall and shopped at the Victoria's Secret, Hanes, and Maidenform stores.