My friends, it has been a long three and a half months since I last dressed as Jessica. Our current living situation (a couple of roommates) has really hindered an activity that I love so much. Lack of privacy and a smaller space have also contributed but thanks to my amazing wife, I have broken the streak.
Shortly after partaking in a delicious breakfast and enjoying a little bit of NFL football, Rebecca began nudging me to get the process rolling. After a bit of hesitation, I readied the tools — razors, makeup, clothes — and before I knew it, Jessica was back!
This time, though, would be unique as we decided to venture outside. . .
The Preparation
Applying makeup well takes quite a bit of practice and since it’s been a while, I was rusty. Once I finished the beard cover and foundation, I sought the aid of my wife. She took out the MAC eye shadow and went to work, effortlessly completing my look.
My outfit consisted of a strapless black pinstripe dress, a grey cardigan sweater, a thin pink rope belt and black pumps. We took some pictures (coming soon) and ate dinner together in our tiny room, it was absolutely spectacular.
On A Whim
Around ten o’ clock I felt a wave of emotion flood over me and I suggested that we take a drive around town. Without missing a beat, Rebecca said that it sounded like a great idea and she quickly gathered her things.
We snuck out the back door into the pitch black night and hopped into the car. To be outside of my apartment all dressed up basking in the cool autumn air was exhilirating and I had to pause in order to gather myself and soak up the moment fully.
I was focusing so much on driving en femme that I forgot to turn on the headlights, but corrected my mistake before exiting the community. For the next twenty minutes we drove all around town and while we did pass several other cars nobody gave me a second look.
Food Run!
My wife has been extremely supportive of my femme side but managed to throw me for a loop by proposing that we go to Taco Bell for a late night snack. I laughed it off at first, but she wasn’t joking. She was hungry and was sure that I would be fine going through the drive-thru. If anything bad happened, we could just drive away.
Taking her up on the offer, I pulled into the adjacent parking lot and switched seats. I was willing to do this, but sitting the driver’s seat was a bit much for this time. Baby steps, I figured. Things progressed smoothly and we didn’t run into any trouble getting our delicious food.
We enjoyed our little snack in the same parking lot and after driving around for a few more minutes, my wife and I called it a night and headed home. For her, it was just another great time hanging out with me, even though I was dressed as Jessica.
However, this was a major milestone for me. Although I did take a drive en femme at the Be-All conference, I had never left my own dwelling in drag until last night. Believe me, it was nice change from going through the whole ordeal of getting ready only to sit on the couch and watch television.
Above all, I felt like I was living my life to the fullest and really taking advantage of the opportunities in front of me. For this, I am extremely grateful.
In the comments below, I would love to hear about your first crossdressing experience outside of your home. If you haven’t had the chance yet, please share why and if you think that you’ll get the opportunity to do so.
photo credit: Justin Link
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{ 28 comments… read them below or add one }
Awesome, girl! Awesome!
For me, my first time out as a girl was very shortly after I came out to my family and all. I had my first appointment with my gender therapist in Amsterdam and decided to make a good impression by going in girl mode.
I traveled by public transport and it was quite nerve wrecking. I was sure everyone would notice, or worse yet, point and laugh. This wasn’t the case though. Apart from a few looks everything was fine and even in Amsterdam I didn’t have a single problem with anyone.
I went shopping in Amsterdam after my therapy session so I was there for quite a while. Not a single store clerk or anyone else for that matter made a problem out of it. Of course they are used to things in Amsterdam but I was still very new at this and extremely nervous. Though those nerves lessened more and more as the day went by.
I’ve been full time for well over a year now and those nerves are in the past. I still love dressing up every day as it makes me feel good and happy, even if I don’t go out.
Yes, I took pictures of my first time out, lol.
Me on the train: (nervous wreck) http://bit.ly/35nbNZ
Me switching to the shoes I just bought: (yay!) http://bit.ly/ygE8N
Just posing: http://bit.ly/saVAw
Standing next to Darth Vader: (scary) http://bit.ly/3N1dUu
Thanks, and I appreciate you sharing your story and pictures, very nice
!
Hi Jessica,
A wonderful post . I always love reading about when someone has a first.
Your wife sounds a fantastic lady and you are very lucky.
Going out can become very addictive and the most mundane things can take on a whole new meaning.
My one regret is not going out with my wife when I had the chance. .
Now I try to get out as much as possible and it has done wonders for my confidence.
Yea, my wife is so good to me. I am sorry that you didn’t get a chance to go out with your wife
.
My first time out was just a quick walk around the block. Nothing earth-shattering like going to Be-All or going out shopping, but a big step for me. It was during the fall last year, and I got dressed at home, wearing a pretty simple black dress, hose, heels, and a kind of androgynous black overcoat i have. long black wig with a knit cap on my head, and a purse. I remember standing at the back door of my building, feeling my heart beating a mile a minute, and i remember stepping outside and just feeling an absolute rush as the wind blew onto my legs. The walk was a blur, but I was so elated by it, that I knew I had to do it again, and I did the very next night!
Still working on going out and interacting with people, but little steps, right?
Sounds like one fantastic walk
!
Yes, little steps help us take larger ones down the road
CONGRATULATIONS! Empowerment is a wonderful thing, huh! Kudos all the way ’round!
Thanks! I really appreciate it
> For this, I am extremely grateful.
I feel it’s the little things that make it all worthwhile.
Each little trip out brings back a lot of memories. I remember stepping outside the house at night and fetching something from the car. I think that was my first time outside. Even though it was very late at night, I was very much a bad of nerves – why does heels sound so loud in the quiet?
I remember my first visit to a tranny social group. Pulling up in the car park – the crunch of gravel under the tires – and me swinging my legs out (“knees together, ladies!”
) to climb out. Again, the tak-tak-tak of heels on stone, the swish of my skirt and the grip of my wig against my scalp. I remember taking a deep breath and walking through the dark car park towards the front door. Well worth it tho 
Yes it is so worth it once you start taking advantage of these opportunities
You Go girl ! ! ! I hadn’t been out dressed in a while until a few weeks ago.
I live in a really small country community where every one knows everyone and there vehicles. But a few weeks ago I decided to go out and meet some other ladies in b’ham, Al. which is about 75 miles from where I live.
So I spent a couple of hours getting ready and completely dressed i got in my vehicles drove past my moms house and several other people I knew and they me. Drove the whole way enfemme meet with the girls and had dinner chatted for a while and returned home. All while completely dressed.
I am planning for my wife and I going out halloween night for dinner.
Hugs Misty
Thanks Misty!!
Sounds like you’re having lots of fun too
Well done Jess! It is an incredible liberating feeling to venture out into public dressed as a woman, I am really pleased for you. You are incredibly fortunate to have such a supportive wife. Unfortunately we have to be careful as there are many who want to hurt us. You just had to read the comments from the Jonathan Escobar video you posted. THere was a lot of hate there. He was very brave but I do fear for his safety. We have to be prudent and careful.
Hugs
Sissy Karen
Yes, you’re so right. We do have to be mindful of our surroundings and take precautions. Thanks
My first time out in fem clothes when not as part of a costume. I was barely 19 (I think) and went out shopping in a hardware store near my house wearing a bodysuit and jeans. I wish I had been wearing fem jeans then but I was not.
That’s cool Gaven
That’s awesome girl! I’m so glad you got to be Jessica again and even better to get out! There’s nothing like it, is there?
My first time out was like so (and I’ll copy and paste verbatum from the forum I originally posted it to)…from May 12th of this year:
So I did it! I just did it, I opened the door, didn’t look back and stepped outside the house. It wasn’t no garbage I was putting out this time! No ma’am, this was something even bigger! I got the mail!
LOL ok so it’s not that big but it’s HUGE for me. I got home from work today and worked out and then took about an hour or so to get my legs and face shaved and then all dolled up for my weekly [dress up]. All day I had been telling myself that I needed to get the mail today. I mean I dress up almost every day now but not with beard cover and today was full beard cover , everything day.
Rewind, as I was driving onto my street from work, I saw that my neighbor had a buncha kids over for some reason, I was thinking to myself “hopefully they’re gone in an hour or so”. Well the good news is they were. My neighbor across the street that always has his garage open and is always doing something….it was shut. The neighbor on the left’s house was silent and the neighbor behind me (easment) who’s usually flyin by on his motorcycle gave not a peep either.
I crossed the street to the sidewalk and started towards the mailbox, ~ 100 feet away. Then I noticed that the neighbor to the right of me was out workin on his car as usual. I glanced at him but he hadn’t seen me yet. I kept walking…..wow I really thought I could walk in heels but I felt like I was going soooo slow and a bit awkward. I glanced down the street to my left (away from my neighbor) here and there and mostly just kept my eyes straight ahead. I was too chicken to see if he was looking at me weird or anything but I felt like he might’ve stopped and did a double take, not sure though, could frankly be all in my mind. I got to the mailbox right as he got into his car and started to drive off but he was going towards the dead end so he was turning around. On his way back, I was still crouched down getting into my mailbox but his car stopped in the middle of the road for a few seconds, I still didn’t look up. He finally drove off as I was closing my mailbox.
I walked silently (but still slightly awkardly) back to my house, blood definitely pumping and I was probably feeling a little shakey. But feeling good still!
Sweet! You had an amazing experience, thanks for sharing it so vividly
Mmmm…
I Love Tacos!
I’ve never been outside my house, and I’ve been dressing for almost a year now. I am thinking about stepping out back next time?
Just to see how it feels. I know there’s nothing stopping me from going anywhere I want, except me.
I just recently wrote about this too. It’s amazing how so many Gurls write about similar things in their Blogs.
I too spend hours getting ready, only to be dressed for a few hours at most. Once I just fell asleep as Cassie, and even that felt good.
I suspect this has something to do with me posting YouTube videos. At least some one sees me…
That Wii transition video looks pretty appealing now, doesn’t it Jessica!
I wonder if you ever thought you’d be so grateful to sit in your car eating Taco Bell, or that it would feel so good?
I’m glad you did. Thanks for sharing : )
Cassie…
Aw, thanks Cassie
I appreciate your comments and let me know when you venture out!
My first time was as nerve wracking as everyones but I went with another girl to a bar in Las Vegas. It was during pride week so I wasnt alone. I kept thinking everyone was looking at me but they really were not. Now when I get dressed up I dont feel nervous at all. I feel very normal and relaxed and I adore my cloths no matter what I wear.
That’s great to hear, sounds like you just get more and more confident each time
That was great to read…. good for you!
Thanks Tanya!
Jessica -You are my hero.
I think my wife of 59 years would have enjoyed an escapade such as yours. We had many good times together. We used to work in amateur
theatre production. As I look back unfortunately I never had any female roles. I think I would have enjoyed them. I now read about your activities vicariously.
Awww, that’s so sweet Warren, thank you. I really appreciate you taking the time to read my postings and leaving such wonderful comments.
Halloween morning. For the first time out, I put on my green blouse and skirt, white necklace, Kneelength hose and clutch purse and went to the cafeteria in my retirement home for breakfast. The few people I saw there said I looked very nice. No derogetary comments. I would like to do it some more but I don’t want to wait for next Halloween.
I wll let ou know of my next attempt Warren
Yay! Congratulations Warren, yes please keep me updated.