The last couple of days were, for me, two of the most interesting and eye-opening in my life. Jen made her first trip into the world outside of the little apartment that she has lived in since being conceived. She was free! Free to run in the meadows, free to soar with the birds, free to live her life, and finally free to be whoever she wanted to be, and free to do whatever she wanted to do.
In deciding to get away from my bubble, I booked a two-night stay at an Airbnb in Oaklawn, the LGBTQ center of Dallas. I wouldn’t have to fear anyone or have to hide myself in Oaklawn. Jen could be free. And, as it turned out, Jen WAS free for those two days…
It all started on Thursday. Taking off early from work, Jen had on her black leggings, a black bra, a silver necklace, and a red top, all hidden by a pair of manly baggy jeans and a hooded black sweatshirt by 3:30. My little suitcase contained all Jen’s worldly belongings. Her breast forms, white mid-heeled shoes, a long-haired wig, makeup, and jewelry were in a separate box, ready to be put on as soon as I was out of my apartment complex.
I drove to a nearby gas station, which had a parking lot at the back. That’s where I intended for Jen’s transformation to be complete. I took off the baggy jeans and sweatshirt, put on the breast forms, the white shoes, the wig, lipstick, a couple of rings and a bracelet. Jen’s transformation was ALMOST complete.
Earlier in the day, I had painted my toenails. All well and good. I went to work on my fingernails… and messed them up. Nail polish all over the sides of my fingers. Used nail polish remover and tried again… and failed again. Feeling frustrated, I gave up and ran to the local Walmart. I purchased press on nails but waited until I got to my Airbnb before applying them.
So, Jen, for the first time, drove a car. It was exhilarating. In trying to describe the feeling, it was like putting excitement, happiness, peace, confidence, beauty, and sexiness in a blender and blending them together on high for a minute, and then pouring it into me. You catch my drift.
I drove playing ’90s R&B with the windows partially open, even though there was a cold wind. Nobody seemed to notice me, and if they did, I didn’t notice them. I found the assigned parking spot, got out. Another first, Jen stepped out in front of other people. I got my suitcase out, walked up the stairs to the apartment, punched in the key code, and opened the door. And I stepped into the apartment. It was a clean, cozy, nice, and tidy place.
I settled in, got my clothes out of the suitcase, ironed them, put them up in hangers, got my makeup kit out and arranged all the makeup in the bathroom. I took a long, hot shower, shaved my arms and legs (again!), shaved my face, and put on some makeup. I applied the press-on nails and added some jewelry. Dark blue pants, a lighter blue sleeveless top, a black cardigan, black high heels, and the wig. And I walked out.
I was conscious of my walking. It was still a more masculine walk, but I really didn’t care. I made the walk to Sue Ellen’s, which was about a 5-min walk away successfully (given that I had never walked on a rough terrain in heels!!) Sue Ellen’s was mostly empty as it was a Thursday night (and apparently, they didn’t serve food.) I was starving, skipping lunch because of my excitement, the trip to Walmart, and trying to finish work early. I went to JR’s instead, a gay bar. There were a few guys hanging out at the bar. I ordered food and a beer. Other than the bartender, nobody spoke to me, nor did I. Talk about being nervous! I finished my meal, paid my bill, and walked out. It was enough excitement for today. I walked back to the apartment.
I changed into silk pajamas. Looking at my nails, I realized they make a huge difference in how I feel about myself. Painted nails make me feel womanly, something new that Jen learned.
I ate breakfast at the apartment and at 11am, I dressed in a blue flowery dress, white heels and my black cardigan. I headed out for some exploring. After window-shopping, I got some lunch at Roy G’s Grill. I ordered a bowl of Texas chili and a glass of rose wine. Then another glass of wine and another. Bad idea! I’m a very light drinker and three glasses of wine tipped me over the edge. It was all I could do to pay my bill and walk back to the apartment. I didn’t even change – went straight to bed.
A couple of hours later, I woke up with a hangover. I had some coffee, took off my clothes and makeup, and took another long, hot shower. I lay down, closed my eyes, and fell asleep again. I woke up after an hour feeling much better. I took another shower, shaved, did my makeup, and added jewelry. I wore a dark-orange wrap-around dress and black heels. I felt sexy, so I didn’t wear the cardigan, deciding to brave the cold in just the dress.
I went back to JR’s to eat. It was busy. I sat down at the bar next to what turned out to be an amazing cis woman. We ended up having a very open conversation about what it was like being a closeted crossdresser. She was an aesthetician and had worked with men, women, crossdressers, and transgenders.
Just before she left, she asked, “You’re Indian, aren’t you?” “Yes,” I replied. And she said, “I have Indian nieces and nephews, so I know about Indian culture, and I know how your family would react if they found out. Just hang in there and try to be yourself.”
As she stood up to leave, she looked me in the eye and said, “Be yourself. Dress up if you want to. Don’t be afraid to be yourself. Life is short and you’ll regret it if you’re not true to yourself.” She hugged me and was gone. I almost had tears in my eyes.
I finished my meal and went to Sue Ellen’s. I ran into my apartment neighbors and hung out with them and their friends until around midnight. While walking back to the apartment, I felt a drop in my mood, knowing Jen’s wonderful weekend was about to end. I changed back into my pajamas, got into bed, and reflected on my time spent fully En femme as Jen. It was a happiness that I hadn’t experienced since the moment my daughter was born. It made me realize there is a whole different side of Jen I hadn’t known about before. Playing dress up and living the En femme life are very, very different experiences. This excursion made Jen very real for me. She truly exists and isn’t just a figment of my imagination or a name on the CDH website. She is a real, physical being who walks and talks and has conversations with people and lives a real life.
Falling asleep, I knew Jen had fully become a part of me. Or maybe, I have fully become Jen.
I woke up at about 7am, made some coffee and grudgingly started my retransformation into my masculine self. First went the press-on nails, and then the nail polish on my toenails. All the clothes were re-packed into the suitcase and the makeup into the makeup bag. I was uplifted by the thought that this isn’t the end. Jen will be back. She’s inside me, a part of me, and she’ll come out again at some point. Maybe not tomorrow, or next week or next month, but she certainly will come out.
As a final hurrah to Jen, my masculine-self walked into a spa and had a mani-pedi session, just for the heck of it. I can’t wait to live Jen’s life again, even if it’s for a day.
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Jen thanks for sharing your fabulous weekend. I’m glad you got to enjoy life as Jen.
Thank you, Susan. It was exciting as this was the first time I went out in public as Jen and it was a wonderful experience. Can’t wait for the next one!
What a lovely weekend you had and you looked so nice. There is that exhilaration being your true self. Now you are out of the suitcase I hope the sky will be the limit for further adventures.
Thank you, Angela. It certainly was a lovely weekend and Jen is becoming more prominent in my life. In fact, on most days I’m more Jen than my masculine self, and I love it!
great successful story of going out dressed with a positive outcome thanks for sharing
Thank you, Leah. It was certainly a very positive experience for me.
Your story has a wonderful timeline and so well planned out. Now that you have flirted with your fem side you will never stop like most of us here. Hugs sis
Thank you, Deborah! There’s no stopping Jen now. She has completely taken over my life.
Congrats, Jen . Hope your Cd journey takes you where you want/need to go. Being out as your fem self is such a high. I know for me Cassie is taking over and I love it.
Thanks, Cassie. It was certainly a high. I haven’t had the chance to go out in public again, but I’m gearing up for my next trip out. Hopefully very, very soon.
Thank you for sharing this great experience!
Your story is full of emotions, and I can imagine what a relief it may have been for you to feel comfortable being out for the first time in Jen.
I wish you more and more similar experiences.
Thank you, Kirra. I was surprisingly comfortable being Jen and never hesitated or felt awkward. It was a wonderful experience.
Jen, that sounds wonderful. I’m glad you had such a wonderful, positive experience! Thanks for sharing!
Jen what a wonderful and fabulous weekend, I so happy for you to have had the chance, it builds confidence in us to see it can be done and so enjoyed. May Jen have many more wonderful times ahead.
Thank you, Sherri. It built a lot of confidence in me, knowing that I can be myself. I feel validated.
That is weird I was just in Dallas and discovered Oaklawn and also drove their to be Diana, just walked up and down that street with all the bars you mentioned…..this was January 25 or so….you described just right….I bought a velvet cocktail dress at the second hand shop to add to my collection….
Hopefully you had as wonderful a time as I did. I went into that shop but didn’t find anything that I liked. Let me know if you’re ever in Dallas again and would like to meet up for drinks or a meal.
Wow Jen, what a lovely time you had and I can see much of my own experiences through your descriptions. Going out is far different from being dressed at home and stories like yours can hopefully motivate others to give it a shot. It’s a great big world out there and having an experience like you did can only make you want to enjoy a little more of it. Thanks for sharing.
Yes, I’m certainly hooked and can’t wait for my next trip. I’d like to do it more often, but life doesn’t always permit for that to happen. For now, I have to make do with dressing at home.