We’re so happy to share the story of Chrissy Hilton with you all. This native of PA is a girl after our own heart. She is one of a large number of girls we know who frequent the pretty and liberal town of New Hope, PA – a beautiful oasis for girls shopping, lunching or just browsing. We love how Chrissy puts together her outfits and her selection of wigs. Look and learn ladies!
Let’s start by telling everyone where you are from?
I currently live in the northern suburbs of Philadelphia halfway between Philadelphia and Allentown. I grew up in the western suburbs of Philadelphia, so I have lived in the Philadelphia area my whole life.
When did you first start dressing and how did it come about?
My first recollection of doing anything of a feminine nature occurred when I was pretty young, probably 5 or 6 and I would visit my grandmother and she and my mother and great grandmother would sometimes paint their nails together and I remember asking them to do mine and they would do one or two and I just loved it. The smell of nail polish even to this day brings that memory back.
I also remember discovering my mother’s lingerie in her dresser when I was about 12 or so and being fascinated by it and then trying it on. I think this is a common occurrence and it was something I really enjoyed.
I did not have much contact or desire to dress until a few years ago, 2015 to be exact, when I developed the desire to experiment with wearing feminine clothes. Though my wife is much smaller than I, I tried some of her lingerie on and was hooked. That led to a progression that goes on to this day. I soon realized that the ultimate goal would be to go out in public dressed and that became my goal.
I developed some friendships with others online who were inspirations to me and started to buy some real clothes. I finally decided if I was going to be serious about this, I needed help with makeup, because all women know how to do their own makeup. So, I got up the nerve to schedule a day with Amanda Richards for a makeup lesson and photo shoot in 2018. Chrissy was really born that day once I saw how I looked properly made up.
How did you come up with your Femme name?
I came up with Chrissy because it wasn’t too different sounding than my male name that also starts with a hard C sound and it seemed quite feminine. I soon realized that I was going to need a last name, so I chose Hilton based solely on the fact that I had vacationed in the past on Hilton Head Island and it’s one of my favorite places and being Chrissy is one of my favorite things so I figured it all went together.
How often do you dress?
I try to dress monthly. I’m friends with a group of girls that tries to get together on a monthly basis and I dress for those days out. I’ve gotten to the point that I only like to dress if I’m going out in public. It’s very important to me to go out and be seen whatever that means…lol.
Are you married/in a relationship? If yes, are you able to share your female self with your partner?
I am happily married to a woman that I first began dating back in 1976 and we have been through a lot together, including Chrissy. When I began dressing in 2015, I did not tell my wife, I was too embarrassed and I kept Chrissy hidden. I was never comfortable with that situation and on numerous occasions I would try to bring it up and discuss it with her, but we were never able to do it. Based on various slip ups by me over the years, I thought she had an idea of what I might be doing.
Last year, in 2021, I finally came out to her, primarily because of a situation where a friend called me and my wife wondered who it was. While the revelation was tough, we were able to reach an understanding whereby my wife “tolerates” Chrissy. She doesn’t want to see or have anything to do with her, but she goes along with Chrissy’s monthly outings, clothing purchases and friends. In all cases, my wife and family must come first and that is an easy condition to keep.
In retrospect, coming out to my wife has been one of the best things for Chrissy because I am now able to freely go out with my friends on a monthly basis without any worries. The reduction of the stress related to this lifestyle has diminished considerably.
Tell us what goes into getting the perfect photo?
When I find the perfect photo, I’ll let you know. After taking pictures there always seems to be something that is slightly out of place, but I am a perfectionist.
I always make it a point to smile. I was told to do that a long time ago and I really concentrate on it because it is not a natural look for me. I also try to strike a feminine pose as well as I can, and again, that’s not always easy.
A nice outfit is imperative too.
What are some of your favorite outfits/fashions?
I absolutely love anything feminine, especially the little things like jewelry and painted nails, both fingers and toes. I could not wait to get my first thumb rings and I will not go anywhere now without them.
When I began I primarily wore skinny jeans or leggings, but I have moved on now and incorporate dresses and skirts more in my outfits. I love wearing boots, especially booties and recently bought my first pair of over the knee boots that I love.
Since my times out are primarily for lunch and shopping followed by dinner with the girls I tend to wear a dressy/casual look, kind of a suburban mom look.
Stockings or pantyhose?
Both!!! Stockings and a garter belt are one of the things that attracted me to dressing. However, the need to dress in a manner that will facilitate being out all day into the evening means that pantyhose are much more practical.
My wife has pointed out to me that a lot of women now do not wear either stockings or pantyhose and in the warm weather I do not wear either myself. I keep my body shaved at all times, so if I wear a dress in the warm weather I go with bare legs and that also enables me to indulge in painting my toes and wearing toe rings, another thing I love.
Heels or flats?
While I do own some flats and sneakers, I’ve never worn them. I love the look and feel of something with a heel to it, including wedges. I will sometimes pay the price for wearing heels all day, but it is worth it.
I have noticed when I am out that the majority of women do not wear heels out for the day and are either in flats or sneakers. While I like to emulate women I see in public, I do want to keep my heels.
Favorite places to go when dressed?
Generally, my friends and I go out in the New Hope/Lambertville area of Pennsylvania and New Jersey respectively. It provides a welcoming atmosphere and is much safer now than being in the city.
I will go anywhere dressed and have been out in Philadelphia and the Allentown area in addition to New Hope. I went to Keystone for the first-time last year and it was fabulous and I hope to get back in 2023.
Go to accessories for a night out
As I mentioned, I really love rings, both fingers and toes and I always wear bracelets, usually stacked and being an older girl, I still like wearing a nice feminine watch. I’ll wear an ankle bracelet when appropriate and also love earrings.
I make sure I always have a nice perfume on when I go out.
Who is/are your female role model(s) and why?
I would have to say, my principal role model is my wife. I love the way she dresses and I try to emulate some of her styles, though I am a little more edgy than she is and will wear some things that she will not.
I also watch women in public to see what they are wearing and how they act while out and will file certain looks and styles in my brain for future consideration.
I like to look through catalogs and newspaper inserts to see what is for sale to try and keep up on the current styles.
Tell us some fun facts about yourself. What are your hobbies (either when dressed or not), likes, things you do in your spare time, or anything else you would like to share?
I like to play golf. I started in 2013 and it’s become an obsession for me, it is also another form of exercise because I try to walk when I play and I can get a good workout by hitting balls at the driving range. I also workout with a trainer weekly and try to go to the gym on a regular basis.
I like taking vacations with my wife and family and spending time at our vacation home down south.
I have always been a history buff and like to read books related to my historical interests and visit historic sites when on vacations.
Any stories you would like to share about yourself and your journey?
I have been on a very accelerated path since 2018, so a lot of things have happened in a short period of time. The most important thing for me though has been my being able to get out in real life as Chrissy. That was my primary goal and I have been able to achieve that. To me, there is nothing so wonderful as being out doing “normal” things in the real world as Chrissy. It changes my whole attitude and being and I am never as happy as I am on those days that I am out.
I have been buying my makeup at the MAC counter at Macys in Philadelphia for a while and had developed a friendship with one of the saleswomen there. The first time I went, she asked me about my wife’s skin tone when I told her what I was looking for. I laughed and said it was for me and showed her my picture on my phone. After a quick laugh and apology we developed a nice relationship and she provided me with some great recommendations when I’d go in to stock up.
One night I was meeting friends in Philadelphia for a Monday Night TGirl event in center city Philadelphia and had gotten a room to change prior to dinner and the event. I was only three blocks from Macys, so I finished dressing early and decided to walk over and show my friend at MAC what Chrissy looked like in real life. On the way there, while crossing the street, a woman stopped me and told me how wonderful I looked!!!! Wow, my night had been made right there!
When I got to Macys, my friend was waiting on another person and glanced at me, but made no indication that she knew who I was. After finishing with her customer she came over and asked me if she could help me, she had no idea who I was. I then revealed myself to her and she was totally blown away, it was fantastic!!!! It was icing on the cake after my other encounter. It was a complete validation for me and remains one of my best experiences as Chrissy.
I also have to mention that I have made some wonderful friendships. My friends and I have developed into a group that has many different paths and journeys though we all care for and support each other. As one of my friends said, we have all shared our deepest secret with each other and that gives us a very strong bond.
If you have social media, what is the best way for others to follow you?
I am on Facebook at https://www.facebook.com/profile.php?id=100011205961732
Before we go, would you like to send a message to your fellow girls out there or a closing statement.
While I do not have as much experience as many girls, I will say that you can set your goals and achieve them, it is possible and I am evidence of that. I wanted to go out and I worked at it and I was able to achieve it.
Also, do not be intimidated. It is scary at first, but most people are very supportive of us and at worst indifferent. I have never had a bad experience in all the times I’ve been out and in fact have received a number of compliments from people passing me on the street.
Be true to yourself, do not worry what others may think and be smart and careful.