Hello

My Story

I was born the first child of two very loving Christian parents. They both took great care of me and are still there whenever I need them. One of my first memories is the time after my sister was born, I was feeding her with a bottle of formula. I loved feeding her. It made her happy so I knew I loved holding and taking care of her. 

We had a great childhood. The two of us were great at playing together. We were all very close with my grandparents, especially my mom’s parents. They lived a couple hours away but we would go visit them frequently or they would come visit us. I remember one time we were visiting my grandparents and as usual I was snooping…I was opening every drawer I could until I came across a silk pink nightgown and robe…I enjoyed touching it and had to put it on. When I did, I loved the way it made me feel! Every time we went to visit them I would get it out and try it on until one day I was told it wasn’t funny anymore and I needed to stop. I remember my heart sinking but I don’t think I ever tried it on again. I do remember finding my mom’s old dresses in my grandparent’s basement and I loved looking at them. They were so pretty! I knew I had to wear them! So then after, until I got too big for them, whenever I got a chance I would try them on in secret. No one ever caught me. I had some close calls where I had to take them off quickly but I had my clothes on underneath so it was easy to hurry. 

I remember in elementary school, my sister got a dress up box. She had all kinds of dresses and skirts in the box. Of course I loved looking at them. Most of them were too small until Mom found some old dresses of hers and put them in the box. My heart started racing. They were so pretty and I couldn’t wait to try them on. I remember over the years that either my sister would dress me up or I would make her a bet or somehow get her to get me to dress up. We always had fun doing it. I even remember doing that one time when my best friend was having a sleepover. She dressed both of us up and we had a great time. My parents thought it was funny, especially because he was dressed up too. 

Growing up… while I had a great family, everyone else around me not so much…. I went to the upper class school in the district and some of the kids were mean to me. I was never a very masculine kid, didn't have a backbone and was terrible at comebacks so kids always picked on me. I remember getting sick of it so much there were years I sat at home without friends. 

One year in late elementary or early middle school, I remember hearing about one of our friends who dressed up as a grandma for Halloween. I remember thinking how fun that would be to dress up and be in public without people thinking too much about it. When my mom asked me what I wanted to be for Halloween, I mentioned that guy that dressed as a grandma and that it sounded like fun. She immediately went to the dress up box and picked out a beautiful burgundy dress and a green skirt with a matching green top. She got some pantyhose out of her drawer and helped me put them on and then the dress. She got out her old short blonde wig, clip on earrings, and after I had them on, she went to her makeup drawer and applied some eyeshadow, blush and lipstick. I remember feeling butterflies and loving it. We took some pictures in the burgundy dress and then she helped me put on the green skirt and matching top. We took some pictures and then it was time to take it all off. I didn’t want to but agreed. I never had a party to go to that year so I didn’t wear them again, well except in secret. 

Middle school came around and I made a few friends. I remember one time I went with my friend's church group to a baseball game. On the way out of the game it poured down rain on us. We were all drenched. When we got back to the church, we all put on clothes from a dress up play box while our clothes dried. I remember seeing a beautiful long dress so I put it on. Everyone laughed when I came out after changing into it but afterwards we just played games like hide and seek until it was time to go to sleep. I took off the dress even though I didn't want to, put on my clothes that were now dry and went to sleep.

When it came time for high school, most of my friends left to go to private school. I was attracted to one of the girls in my band section so I invited myself along to a hangout with her friends. I joined her group but while we had great times together I never really was on the inside and as close as they were. Two of the guys turned out to be gay…never in a million years would I have thought I was LGBT like them. I remember one of our first parties where we were drinking… Someone made a joke that one of them saw our friend sneak off and wear one of the mom's dresses, even though they were just joking. I remember chuckling and thinking thank heavens no one is making that joke about me. I don't need them to know my secret.

In high school, my friends and I were discussing Halloween and someone joked that we should go as "hookers". While my heart raced…..I laughed and said let’s do it! I wore my girlfriend’s short sleeveless gray dress with black flowers on it, a brown wig, black fishnets, high heels Mom and I purchased at Payless, and stuffed the top of the dress. My girlfriend’s Mom put heavy makeup on me. It was the first time I had worn mascara and my eyelashes kept fluttering like they were about to fly away while she put it on but I was loving it! :) We took some pictures, then I was handed a purse and we were off to trick or treat (we were way too old but we thought it would be funny). This was the first time that I felt sexy dressed as a woman. The three of us were dressed up and some people didn’t know who we were and some didn’t even know we were actually boys. It was so much fun! That year I dressed as a girl twice for Halloween. 

Later in high school, my Mom came home early one day and I was in our basement wearing one of the dresses from the dress up box. When I heard her upstairs, I was so scared I was about to jump out of my skin. Since I started dressing at home, I found it was more fun dressing in only my underwear. She found me downstairs in the bathroom and I had taken everything off, put the dress under the kitchen sink and closed the bathroom door. She knew something was up as I was flustered. I never could tell a lie so when she asked what I was doing and I said “nothing” she knew I was not telling her the truth. After she wasn’t going away… I finally broke down and told her everything. It was a weight off of my shoulders to finally tell someone but also terrifying because I didn’t know what she would do. I made her promise not to tell Dad. As far as I know she kept that promise because I never have had anything happen with Dad that would tell me otherwise. Her condition to not tell Dad was that I would see a counselor. I agreed and so she took me to a family counselor.

The days I went to talk to the counselor I was so nervous. We talked about a lot of things but I never could get the courage to tell them about my dressing. I know counselors are supposed to be understanding and not judge but at the time I felt like a freak. I didn’t want the judgment or weird looks so I kept my mouth closed on that topic.

I left for my freshman year of college without anything to dress up in so I didn’t dress until Halloween. My friend suggested I go as a playboy bunny, as a joke of course. I said “challenge accepted”. I went down to the local Halloween store and walked right in with my heart pounding. The owner, who is a guy, was wearing a playboy bunny costume. It was a short pink dress with a fluffy white tail and white fur above the breasts and of course the playboy bunny ears and cuffs. When he asked what I wanted, I told him I needed a playboy bunny costume, just like he was wearing. He asked if I needed white fishnets too and I said "of course". I paid for them and went back to the dorm. I went with a girl friend and bought white high heels at Payless. They were the backless kind so they were a bitch to walk in but of course I still loved it! A couple girls in the dorm heard what I was doing and got excited. One found a pink wig and they did my makeup. It was a fun experience, except for those heels. They were terrible to walk in as the heel flapped every time I walked. The best part of the night was when I met another girl at the party that had on the same costume. Someone mentioned that wore it better and she got all in a tizzy! 

Sophomore year...Halloween I went just as a beautiful woman. I went with a friend to the thrift store and bought a long dark red formal dress. It was long and had some crinoline at the bottom which made me feel prettier than ever. 

I remember telling Mom what I was doing and asked her if I could have the brown wig and black heels with straps that I wore in high school. I had to ask a couple times. She told me couldn't find the wig but gave me the shoes. Before she did though she asked me if I still had the urges I had in high school. I lied through my teeth and said that those were gone. One of the few times I remembered blatantly lying to her. 

My ex and I went to buy some things I needed. We went to a wig store to get a blonde wig. I remember wanting a light blonde wig. I hinted at one to my ex. She told the clerk we wanted the one next to it that was dirty blonde. I remember being so nervous to say anything so I just accepted it and paid for it. We went to Walmart to buy black panties and hose. It was the first time I had my own panties or hose. Another friend offered to help me with my wig and makeup. She decided to cut the wig so I had swooping bangs and applied full makeup, more makeup than I had ever worn. She gave me smokey eyes! She even pulled out some cute dangly clip-on earrings that she bought for me at a store she worked at. I felt sexy! People told me I was pretty, smiled or laughed and then pretty much acted normal.

Later that year when my dorm mates were gone, I pulled out my box from under my bed and put on my Halloween costume from earlier in the year with the dark red gown, hose, heels, and wig. I was terrified someone would walk in at any minute, so much that I didn’t stay dressed long, especially after I heard people in the hall.

Junior year I moved into my own apartment. I didn’t dress up as a girl for Halloween, but it was a great year anyway as I lived in my own studio apartment and this was the first year I could dress whenever I wanted to and not have to worry about someone walking in on me.

Senior year I dressed whenever I wanted to, as I still lived alone. My friend who attended a university in another part of the state mentioned that if I didn’t have anything to do for Halloween that I should come visit her. I asked what I should be and she joked and said I could be her sorority sister. I asked what they wore and she said red. I went out and bought a short red dress with a low cut v neck. When I went to see her she also mentioned that she had a french maid costume she had worn one year and that I could try it. It was WAY too small on me so I wore the red dress, pantyhose, heels, and wig I had brought with me. She applied full makeup and we were off to party after party. I tried to keep up with my friend who could really drink…I drank way too much, so much that this is one of the only couple of times in my life that I blacked out. All I remember from that night was drinking jungle juice, talking to a guy at one of the houses (later hearing that he was flirting with me…I had no idea), laying on the grass in “the quad”, puking in her friend’s car (not my finest moment) and stumbling into the room. I woke up still dressed with makeup still on my face lying on the floor of her dorm room….also not my finest moment. I continued to dress occasionally in my apartment until I moved home.

Towards the end of college, I reconnected with a friend from childhood and when we were both home from school. We went out as friends. I remember her opening the door and thinking she was extremely beautiful. Even though we had known each other for many years, and I had even taken her as my date to homecoming (as friends), I knew that things were now very different for me because I didn’t remember looking at her in that way before. We went to dinner and then to see the movie Juno, of all movies! LOL Soon after, I decided to visit her at her school. We stayed up until 5am, just talking on her couch. I knew I had to take things slow because our parents are friends and I didn’t want to mess that up. I would call her every time I was driving home or driving back to school, just to “pass the time”. Shortly after we started officially dating….and a couple years later, I asked her to marry me.

After college, I moved home and for the few months I was home there was no opportunity to dress but when I moved into a townhouse by myself I was able to dress occasionally when I didn't have to work and my fiance was not around.

Before we got married I did what I thought was the right thing to do and told her that I liked dressing as a woman…. One of her favorite comedians is Eddie Izzard. If you don't know, Eddie is a transvestite who does not hide it at all. I told her I was kind of like Eddie. She said you mean you like wearing women's clothes. I said unfortunately yes. We went through a whirlwind of emotions and conversations that week. From "can you just dress on Halloween?" to "I don't know if I can do this"... it was one hell of a week for the two of us. In the end she stayed with me even though she still tells me to this day she really was about to break up over it and sometimes thinks maybe she should have.

Shortly after we got married, I remember one weekend laying in bed one morning while she was getting ready for work. She thought it would be funny to put makeup on me. She put some light makeup on me while I pretended to be sleeping or at least too tired to stop her. I was loving every minute of it. So much that as soon as she was out the door I ran to the bathroom to see. I applied a little bit more makeup because I knew if I had any on me after I removed it, I could blame it on the makeup she put on me. As soon as I was happy with my makeup, I went to the closet and got out one of my old dresses from Halloween, put on my panties, pantyhose, stuff the cups with socks, put on my heels and a wig…. I looked in the mirror and liked the girl I saw looking back at me so I stayed dressed for a couple hours and then removed it all. 

In 2014, after being married and still having the desire to crossdress, I had a plan to try to stop my dressing for good. We were planning on trying to have a baby so we both decided my dressing needed to stop before the baby came. I was going to dress up in full for 30 days straight late-night. It ended up being 42 days. I really thought I could wear myself out of it and hopefully not have the desire to do it again. As per my agreement with my wife, I would set my alarm to wake-up in the middle of the night and apply full makeup, try on all of the outfits I purchased and wear one around the house while I cleaned the house. The first day I walked out of the bathroom dressed, our dog was terrified. She was growling and barking at me so I approached her to try to tell her who I was and settle her but she attacked me. She was so scared, I scared the shit out of her, literally. My wife had to come settle her down so I could get back down to the basement to take it all off. My wife told me that should make me want to stop. I told her I wanted to stop but that was why I needed to continue. I continued the next night to try to make this desire stop for good. Days went by and it did become daunting and exhausting. I was only getting 3-4 hours of sleep each night. I remember at times wishing I could take a night off as I was exhausted but I powered through until the end.

I was hopeful that my desire to crossdress would fade. It did but only for a couple weeks. After that I dressed occasionally, probably a few times a year. I even tried purchasing and wearing a variety of different outfits in hopes I could ruin all types for myself. It didn't work.

April 14, 2021 was a big day! For as long as I had my own computer, I remember going online searching crossdressing and related topics but all I could find were stories of being forced to dress, made a bet and had to dress, magically turned into a woman, etc. It was that week in April that I searched as usual but this time I found a contest that Glamour Boutique was holding. It was a photo contest for crossdressers and trans women. No one had ever seen my pictures of me all dressed up with me applying my own makeup so I was curious what they would think. After some debating, I decided to enter. Absolute best case I win a free breast plate, worst case I decide not to put myself out there ever again. April 14th was the day I decided to enter. It appeared to be easier to enter if I had a Facebook. There was no way I was using my male account so I decided to create a female account. I had never had a female name before so I had to think of one. I thought for a second and it didn’t take me long to remember I already had a name. Growing up my sister would call me Jennifer when she dressed me up and when she wanted to razz me for doing something girly so I decided I loved it and that was it.

I found a community on Facebook and made a lot of friends very quickly. I created a home there and was loving the responses to the pictures I was posting. 

It wasn't until April 2021 that I fully accepted that there was no way to get this to fade. I had tried everything from a lot of prayer, to not dressing, to dressing for 42 days straight and I still had that desire to dress and feel like a woman. So it was then that I wrote out the story you are reading now. I realized it is just part of me and I came to peace with that and love that side of me. I realized I am still the same me, I just have two sides.

When I wrote my story originally I knew that I had no desire to become a woman. I wrote “I love being a man and the man my wife knows and loves. I am still getting to know the other side of me but I do know that she loves to feel pretty, elegant, classy and sexy.”

After I wrote my story, I decided to create a blog to share it with the world to get validation in hopes that someone out there reading it would benefit by reading it in some way. I never imagined what it would turn into. Thousands have read my story and many of them reach out to tell me they were either inspired or felt connected and less alone as they had experienced similar things in their life.

My wife had always said the thing that bothered her most about my desire to dress was not understanding why. At the time I was not able to answer that question. Since then, I created this online community where I found myself seeking more and more answers. I talked to people, continued searching the internet. It was then I noticed a lot of my Facebook friends had liked a page called The Fox and the Phoenix Podcast. I looked into it and it turned out it was a podcast solely about crossdressing. I listened to an episode and fell in love. Everything about it resonated with me. I decided to go back to Episode 1 and listen to every episode in order. Savannah Hauk, one of the co-hosts, said she was a crossdresser like me and I just connected and wanted to hear what she had to say. She explained that she was dual gender. I immediately thought that’s interesting but that’s definitely not me. I remember listening to more and more episodes and after listening and self reflection, I thought that is exactly me. I love my male life but I also have this female life that I can’t give up, with losing part of myself, even if I wanted to. I continued to listen to the podcast and chat with friends on Facebook until one day in August 2021 I decided to join Instagram. 

I used the same name, even the same username that I had created for Facebook. I started posting pictures and people were liking my pictures and I was following all kinds of accounts and liking their pictures. Soon I started following accounts of beautiful trans women and women in various parts of the gender spectrum. I had no idea what kind of spectrum there was but I soon began to learn. My following grew and grew and while that was fun and still is, what I loved most was all of the new people that my story was reaching and helping. They reached out left and right and still do and every time they do it makes me smile that I could help someone just by sharing my story. I started writing what I call my black and white posts where I post a black and white pictures of me and share the deep struggles I am experiencing. That honesty and vulnerability resonated with people too. It validated what I was feeling when I had no one in person to talk to and it helped people so I started doing it pretty routinely. Whenever something comes up, I write it all down, refine it and share it when I feel it is the right time.

Last year, I decided I needed to sit down and share what I was going through with my wife and have her read my story. That was one of the hardest things I have ever done. It is important to me that I be upfront with her but that night and many nights since we have so many conversations that have been so difficult. She continues to tell me sometimes she wishes she left me when I told her I was like Eddie Izzard. It is all so hard for both of us. And while sometimes I get so frustrated that she won’t try to understand me or my side, I remind myself…It took me 30 years to understand and love this side of myself…I can’t expect her to understand or love Jenn overnight. During some of our conversations, she has come up with ideas that should basically try to fix me. I listened and even tried a couple. 

She wanted me to see a Christian counselor and maybe they might challenge my way of thinking. I struggled to find anyone who claimed to be a Christian counselor that dealt with transgender issues until I found her. The first time we met we both agreed that she did not have immense experience with transgender issues and that if either of us felt I needed more of a gender specialist we would tell the other. I felt very comfortable with her and shared my entire story and all kinds of thoughts I hadn’t shared with anyone else. She and I had met 2 times and then the week before my 3rd appointment I received an email from her. 

She explained she had some things going on and was stepping away from counseling. I remember wanting to cry and also being mad. I was mad that she let me start counseling with her only to leave me after 2 sessions. I am not a runner but even after chatting with a friend on IG, it was midnight but I decided I needed to go for a run, something I hadn’t done for a long time. It was therapeutic and I was a little calmer when I got home. I re-read the email and it said our last session would be next week and she was looking forward to seeing me then. I decided to go to our final session to share the things I had written down, wrap things up, hear who she thought would be good for me to see, and say goodbye. 

I was in a very good headspace when I arrived at our final session. I went through my list of things I wanted to talk about and when it came towards the end when I planned to hear her list of people she recommended for me, I felt a great calm come over me. Instead of asking to hear her list, I proceeded to explain that I thought I would be frustrated and not want my sessions with her to end but I felt like I was in a good place. I asked her if I could ask her a question. I asked her “Do you think I am in the right place where it would be beneficial for me to see a gender therapist?” She explained that she was so happy with my progress and could see how much more comfortable with myself I had become. She also said she thought I could really benefit from seeing a gender therapist. So I decided right then and there that’s exactly what I would do. I reached out to the gender therapist I had come across several times over the years of searching online and reached out and we scheduled a session. I remembered I had actually emailed this same person back in 2015 but after she responded, I was too scared to take it any further. Now I feel I am in the right place and time to figure me out. 

Am I dual gender and have these two sides of myself that will continue to be completely separate? Am I dual gender and I need to find some way to blend the two sides together even though currently I have zero desire or enjoyment when I do? Or am I trans and I am just on my journey to transition? Only time will tell but I’m now in a great place in my life and ready to figure it out.

*As you know that's not where my story ended...for more, make sure to watch for my book that I am expecting to release this summer. This story you just read is a snapshot of a small part of my journey. My book encompasses my entire soul and every secret. I can't wait to share it with you!