Deanna's First Time Out-At Least I Didn't Get Arrested!

[Deanna Lund]

Let me begin by saying that I have an obsessive/compulsive personality, probably not the best thing for a cross-dresser!

I am not clear what triggered things. I have had a slight infatuation with panties and bras for decades but it was infrequent, extremely infrequent and very minimal. Then, about a month ago I got a full on obsession. It started with buying some lipstick and leaving lip prints on cups (pretty juvenile right?). Then I bought some false eyelashes. Then a dress from Macy’s, a matching purse-happened to find one at a thrift store where I also bought a skirt and a cute woman’s top I knew was too small but thought I could cut it open and tie it in back (yeah, that didn’t work). I ordered a wig (bob style from Amazon and joined CrossDressingHeaven. I was on a roll and couldn’t stop.

I got interested in makeup and looked for videos on Youtube showing how to do it. One of the first ones I watched was a guy who looked pretty good made up and explained how easy it was to look good. So I watched his video, went and bought the items I needed and proceeded to apply the makeup according to his instructions. Things did not go well but I was determined to go through McDonald’s drive-through en-femme  and did.  That experience almost ended me.  Turned out that the video I watched was by a pxxx (replaced the 0, r, and n with x’s so the CDH filter would not flag it like it did on the forum post where I gave full details on the disaster) and I should not have spread foundation on with a trowel like he did. I really wanted to become a woman so I went back to the drawing board so to speak and watched more videos, this time selecting ones which were by actual makeup artists and pretty girls, some of whom were actually cross-dressers. I discovered that less makeup is better than more and was convinced that I could do this.

I collected the makeup and clothing items I needed, reviewed the videos and made notes. I created my breasts using stockings and 1 pound of rice per breast and started planning operation Deanna’s First Time Out. The plan was simple. I live in Titusville Florida so I looked for a cross dressing business near me but far enough away that I would not be recognized by anyone.  The best choice seemed to be Ritzy Rags about 40 miles from my house. My wife was not going to come home for lunch on Tuesday, April 2, so I had the date.

Tuesday morning, I got up and started getting ready. RR did not open until 11am so I had plenty of time.

First I did my makeup routine.

Shower

Shave

Moisturizer

Primer

Concealor especially under eyes

Foundation, applied sparingly and blended.

A simple medium brown eyeshadow as recommended by the makeup artist I had been watching. I decided to save the ultradramatic smokey eye makeup with dual bat wings for another time.

Applied my eyelashes, completed with effort

Finally, applied Cover girl setting spray to my face.

Next, I put on my nails.  That turned out to be harder than I thought. The kit I had consisted of about 2 dozen nails of different sizes so I had to figure out which nail was the closes match for each finger. They were all a bit smaller than my somewhat large woman’s nails but I did the best I could. The glue they provided was not easy to apple from the little tube so I got a new tube of super glue and liberally applied it to any nails which came off. I had not anticipated that the more nails I got on the harder it would be to apply the next one. Eventually I got them all on though some were a bit crooked, but not terribly so, and once I had cemented them in place I could not move them.

Next, I put on my bra. Fastened it shut then put it on over my head but while pulling it down in back, I lost a couple of nails that were only lightly glued on.  I got the bra adjusted, boy  girl did that smooth material feel good on my skin. I inserted by rice breasts (they smelled like rice. I remember when I was a teenager I read a book called Myra Breckenridge it claimed the Myra’s breasts smelled like freshly baked bread.  As an I am adult married man person with 3 grown children so I know that women’s breasts don’t smell like freshly baked bread, but it occurred to me that if my breasts smelled like rice, I might be able to infuse them with other scents. Vanilla, cinnamon, chocolate, coffee, … maybe even yeast to simulate bread. I have plenty of knee socks left over from my breast making and bags of rice are cheap so I made a note of this for future experimentation. And cemented on the nails which had come loose.

I put on my dress and noticed how hairy my legs and arms were. I had planned to Nair them but Monday night, I read the instructions on the bottle of Nair. It cautioned that the produce might cause skin irritation and I should try a small patch and wait 24 hours to see if there was any reaction.  So, Monday night was too late to do that and be ready to go Tuesday morning so it was either shave, risk a rash, cancel the trip, or go European style. I chose the latter.

Ok, so, I have my makeup, eyelashes, bra, breasts, and dress. I put on my wig, put the items I would need in my purse (wallet, keys, phone, touch-up lipstick took a look in the mirror snapped a quick selfie, put on on heels and headed out the door.

About three blocks from home a bug was hovering in front of my right eye so I brushed it away. It turned out not to be a bug, it was my right eyelash.  I still had one good eyelash so I wasn’t going to abort the mission.  About a mile down the road, I noticed that my dress was riding pretty high, much higher than I had thought it would, in fact it was close to exposing my underwear to me and it would certainly be visible to anyone in front of me if I were sitting.  I note, for the record that I intend to buy some panties, but the slutty one’s I had don’t fit, and I have spent so much on makeup and other clothing that I had put off buying panties assuming, as a proper lady, so I wore men’s briefs since I would not be showing them anyway.  Another decision point: Continue or abort? As I said, I am obsessive and nothing would stop me from doing this so I continued on.

I arrived at Ritze Rags about ten after noon. Parked in the back and got out of the car. In the process of getting out my dress rode up completely exposing my underpants. It’s hard enough being a girl, try being a lady! Fortunately, no one was around so I pulled my dress back into position, found my lost eyelash on the floor of the car, locked the car and headed inside.

Ritzy Rags was immaculate inside. It did not have that musty smell that older building sometimes have and was brightly lit. The first thing I noticed was about a hundred pictures of female celebrities.  They were beautiful women. Then it dawned on me that they were probably female impersonators.  It turns out that Leigh Shannon, the owner is a well known performer of that genre.

As I walked further on an employee appeared and smiled at me. I introduced myself and she told me her name was Linda. I explained that this was my first time out and she congratulated me then we spent some time discussing girl things like makeup-missing eyelashes, I had lost 2 more finger nails on the drive over, one in the parking lot, etc. She didn’t bat an eyelash (ha) and gave me some practical pointers and hacks on putting eyelashes assuring me that losing an eyelash happens to all girls. We talked some more and she introduced me to the owner and told him this was my first time out. He also congratulated me and didn’t seem to notice my missing eyelash.  We chatted a bit and I noticed their selection of wigs.  I paid under $20 for my bob as I wasn’t sure how this CD thing was going to go, or even last (though I am loving it). They showed me a back wall with wigs on sale.  One of the wigs, a blonde with lots of hair caught me eye. She said it was $60 on sale and I could try it on if I wanted-I WANTED!!! So she took it down and I expected her to put in on me. NOPE, she led me to a chair, like a barber chair with mirrors all around and bright lights, and bade me have a seat. OHHHHHH. There are time in a girl’s life when modesty rules the day, and times when it doesn’t, on this day, it did NOT so I sat down and adjusted my dress as best as I could, which was not much. I blushed and apologized for the shortness of my dress. She blew it off, “Honey, you don’t have anything down there I haven’t seen before,” she said. She put on a protective wig cap, health regulations for trying on wigs, and put on the wig.  That wig must have three times the hair my bob wig has but it fit better, was lighter and cooler and I love the bangs.  She spent quite a while with me explaining how to put wigs on, how to care for them, how to brush them and more.  Honestly, I wanted to buy something there before I walked in but Linda made me feel so welcome, without being fake or pushy that sealed the deal.

I also asked her about my lipstick. It was no longer just on my lips, it had bled in irregular ways around my lips.  I had not used lip liner. I should have outlined my lips with lip liner, then filled the lips in with the lipstick.

I bought the wig and paid for it using my pursed at a store for the first time!

On the way out I asked if there were any restaurants nearby where a girl like me could eat without being uncomfortable and she told me that there was a taco restaurant next door as was the transgender center* for Orlando so I should have no worries.

I left happy but decided not to press my luck. I was alone in RR except for Linda and Leigh so I didn’t really have anything to worry about, but I didn’t want to risk being arrested for flashing my ‘panties’ in public, especially given the special nature of Deanna and her dress for the day.

I drove home feeling very contented.  I completed my mission. It wasn’t perfect but it was good enough.  I even stopped at McDonald’s on the way home and ordered an iced coffee and hamburger as Deanna, voice included. Linda said my voice sounds natural. I hope so, she might have just been being nice.

On the drive home a potential problem occurred to me.  My fingernails, the ones that had not come off, how was I going to get them off? I had cemented them on not really considering what that meant.  I know a bit of chemistry from my school days and thought I could probably get them off using acetone but did not know if we had any.  I was too happy to be overly worried and enjoyed looking at my bangs in the mirror during the ride.

I got home and took some pictures of me in my new wig. Not too bad, even missing one lash-can’t tell. Then, got around to reading about the nails. Turns out you can either tape the nails on using tape supplied with the nails, so that’s what that was, probably would not have worked anyway, or glue them on. If glue is used it is recommend that you trim the nails as close as possible then soak in acetone until soft and peal off.  I was right, and we had acetone, my daughters still visit and sometimes to their nails.

I learned a lot from this outing.  I really want to go again, but somewhere more challenging, though still not in down, though I did stop and fill up the car with gas just down the street from our house.  No one paid any attention to the blonde filling her car.  That made me a bit sad.

*you may recall that Orlando was were the Pulse nightclub shooting happened a few years ago. The Center has been active in Orlando working on the memorial to the victims.

As I write this I am listening to my Echo Dot playing, I Enjoy Being A Girl.

I know that some of you ladies are much more lady than I am, at least at this point, and that many of the things I overlooked would have been deal breakers for you, but I desperately wanted to be out this time.  The next time I will be more fussy. I will have panties on, nice appropriate big girl panties, I will have removed my body hair, I will have my fingernails as close to perfect as I can get them, I will have my lips lined and filled, I will …

Luv you

D

ps, I wouldn’t have missed it for the world!!!!!

• This topic was modified 5 years ago by Deanna Lund.

[Brittney Andrews]

Hello Deanna; Thank you for sharing your story. When we begin our journey, our look is always an evolving work-in-progress. It’s very rare to get everything perfect the first time. Deciding to go to a CD specific store for your first time out was a smart plan. It appears that you had a great experience.

[Anonymous]

Thanks for sharing Deanna.  I am glad the day went well for you, but I am just tired from reading it.  You put a lot of effort in for that outing, but you know as a CD, it does take a lot of effort, but so worth it.  Have fun on your next venture out.

[Angela]

Hi Deanna, I loved your story! Thank you for sharing it. I loved hearing that after each roadblock you kept preserving. Nothing would stop you. When I get the courage to go out and I hit those roadblocks I’m going to think of you and your story and never stop until I accomplish my mission!

Higs,

Angela

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