I recently saw the term "cross dreamer" to describe people that dream about cross dressing but don't actually do it. I felt this described me for most of my life, then I actually dressed for a time then went back to dreaming about it. Things have changed now and I'm exploring my feminine side with the support of my amazing partner. Here is my story.
I took a deep dive into cross dressing several years ago in my mid fifties. I was married and hid it from my wife. I went all out and did as much to feminize myself as I could. Full body waxing, makeup, lace front wigs, breast forms, gaffs, padded panties, corsets, press-on nails, pedicures, jewelry, sexy dresses, skirts, tops etc, and shoes shoes shoes! I went out in public many times, mostly shopping but also to a few nightclubs. I traveled to another city and had a professional makeover and photo shoot as well as makeup lessons. My marriage ended and I thought my explorations would increase, but I found that I really loved being with women more than being a woman so I started working more on my masculine side and put all my girl things away. I went a little wild and dated and bedded many different women over the course of a year. I found love with the most amazing sexy woman and we eventually became exclusive and now we've been together almost five years.
I purged all of my girl accessories that I had acquired when we moved in together. When we first met she was also recently divorced. She and her ex had been very active in the swinger lifestyle and she was still going to parties almost weekly when we started dating. I expressed interest in swinging with her but she was adamant about keeping that part of her life separate from me. She was very honest with me and having Cuckhold fantasies, I loved hearing her tell me about the many other men she was fucking and I would share details about my own adventures with other women. I had been honest with her about experimenting I had done with another man, but I kept my cross dressing history a secret because I knew that she wasn't super accepting of transgenderism.
I thought I had gotten over my desire to dress until my love had me try on a pair of her bell bottom jeans for a Halloween costume 2 years ago. They fit me amazingly and I loved the way I looked and the way they felt! She had gained a little weight and several pairs of her jeans no longer fit so she gave them all to me! I've always thought that my legs and ass look more like a girl than a guy and my desires were coming back every time I saw myself in her tight jeans. I started talking to her about my desire to cross dress and she freaked! Told me I would be ugly as a woman and that nobody in my life would accept me. I tried to explain that I had no desire to transition, and that it was more of a fetish or even a hobby. Over the past few years we've had a few uncomfortable conversations so I tried to downplay it and I started trying on her clothes secretly when I had opportunities. This only made me want more and I started occasionally trying to have playful conversations with her and focusing on that I had no desire to actually be a woman and she occasionally would ask me questions.
Things have changed considerably in the last month. In casual conversation she wondered aloud if she could make herself look like a man. I told her that she could but would have to look like a large bellied man to cover up her DDD breasts and have some fake facial hair. This led to talk of us dressing as opposite genders for Halloween and different ideas for costumes. She said we could go to a thrift store to find high heels for me. I was ecstatic but a few days later she said she really didn't want to dress as a man. She did say that she would let me dress though, A lot has happened in the past two weeks. We went to a thrift store and found a pair of wedge sandals that are almost my size and I look amazing in them! She again started having cold feet but told me I could try on her clothes in private but she didn't want to see me because she was worried she wouldn't be attracted to me anymore and that she wouldn't be able to wear any of her clothes if she saw me in them. She also said I could try on her wigs and made sure to tell me about her club dresses in the downstairs closet. I suggested that I would like to shave my beard but she was against that and suggested I could wear a veil. Even though this was less than a full fledged endorsement, as soon as I had the house to myself I started trying on wigs and outfits! I used a pair of her lacy thong panties to fashion a mask, and took pictures of myself in a few different outfits. She has an amazing wardrobe that fits me great and I couldn't wait to do more!
I shaved my legs and chest and the next opportunity I had I got into her makeup drawer and did my eyes up with eyeliner, mascara, and eye shadow. I again tried on several outfits including lingerie sets and took a lot of photos. I didn't do a proper job of cleaning the eyeliner off and she immediately knew I had done makeup. Her reaction was amazing! She said it looked like I had done alright and then showed me how to clean it off better. The next day she said that she was going to occasionally talk to me about makeup and that I couldn't use her eye makeup because it wasn't sanitary but had given me some items I could have for myself. I was positively giddy, and the next day she was gone for several hours so I had another session of makeup, trying on outfits, and taking pictures. I had tried on several wigs and liked a long brunette one the best, but then I found a long blonde wig that made my heart leap when I tried it on! I looked amazing and it had an aroma that intoxicated me. It smelled like girl! I'm certain that it was a combination of my love's perfume and body scent and it was amazing! I finally decided to start cleaning up because I knew my love would be home soon, I had just taken off the wig and clothes when she came home. I had locked the bedroom door so she asked me if I was dressed. I told her that I still had makeup on but was getting undressed. She said that she was feeling brave and wanted to see me so I said give me a few minutes and quickly chose an outfit that I thought would be good. I chose a black and pink spaghetti strap chemise and thong combo with a short pink checkered school girl skirt topped off with my heels and the blonde wig and of course my "veil". My heart was beating so hard when I unlocked the door and told her to come in! Her reaction was better than I expected and exactly what I had hoped! She told me I looked amazing and I basked in her compliments. She even had me try on another set of lingerie. She said I looked better than her, which I was a little afraid she might say, but I assured her that I didn't look better, just different. Anyway, it was a great experience and has me excited about the future! That was last Friday and I haven't dressed again since because I want her to see that it's a hobby and won't take over my life, but know that I'll get another chance soon!
I took a deep dive into cross dressing several years ago in my mid fifties. I was married and hid it from my wife. I went all out and did as much to feminize myself as I could. Full body waxing, makeup, lace front wigs, breast forms, gaffs, padded panties, corsets, press-on nails, pedicures, jewelry, sexy dresses, skirts, tops etc, and shoes shoes shoes! I went out in public many times, mostly shopping but also to a few nightclubs. I traveled to another city and had a professional makeover and photo shoot as well as makeup lessons. My marriage ended and I thought my explorations would increase, but I found that I really loved being with women more than being a woman so I started working more on my masculine side and put all my girl things away. I went a little wild and dated and bedded many different women over the course of a year. I found love with the most amazing sexy woman and we eventually became exclusive and now we've been together almost five years.
I purged all of my girl accessories that I had acquired when we moved in together. When we first met she was also recently divorced. She and her ex had been very active in the swinger lifestyle and she was still going to parties almost weekly when we started dating. I expressed interest in swinging with her but she was adamant about keeping that part of her life separate from me. She was very honest with me and having Cuckhold fantasies, I loved hearing her tell me about the many other men she was fucking and I would share details about my own adventures with other women. I had been honest with her about experimenting I had done with another man, but I kept my cross dressing history a secret because I knew that she wasn't super accepting of transgenderism.
I thought I had gotten over my desire to dress until my love had me try on a pair of her bell bottom jeans for a Halloween costume 2 years ago. They fit me amazingly and I loved the way I looked and the way they felt! She had gained a little weight and several pairs of her jeans no longer fit so she gave them all to me! I've always thought that my legs and ass look more like a girl than a guy and my desires were coming back every time I saw myself in her tight jeans. I started talking to her about my desire to cross dress and she freaked! Told me I would be ugly as a woman and that nobody in my life would accept me. I tried to explain that I had no desire to transition, and that it was more of a fetish or even a hobby. Over the past few years we've had a few uncomfortable conversations so I tried to downplay it and I started trying on her clothes secretly when I had opportunities. This only made me want more and I started occasionally trying to have playful conversations with her and focusing on that I had no desire to actually be a woman and she occasionally would ask me questions.
Things have changed considerably in the last month. In casual conversation she wondered aloud if she could make herself look like a man. I told her that she could but would have to look like a large bellied man to cover up her DDD breasts and have some fake facial hair. This led to talk of us dressing as opposite genders for Halloween and different ideas for costumes. She said we could go to a thrift store to find high heels for me. I was ecstatic but a few days later she said she really didn't want to dress as a man. She did say that she would let me dress though, A lot has happened in the past two weeks. We went to a thrift store and found a pair of wedge sandals that are almost my size and I look amazing in them! She again started having cold feet but told me I could try on her clothes in private but she didn't want to see me because she was worried she wouldn't be attracted to me anymore and that she wouldn't be able to wear any of her clothes if she saw me in them. She also said I could try on her wigs and made sure to tell me about her club dresses in the downstairs closet. I suggested that I would like to shave my beard but she was against that and suggested I could wear a veil. Even though this was less than a full fledged endorsement, as soon as I had the house to myself I started trying on wigs and outfits! I used a pair of her lacy thong panties to fashion a mask, and took pictures of myself in a few different outfits. She has an amazing wardrobe that fits me great and I couldn't wait to do more!
I shaved my legs and chest and the next opportunity I had I got into her makeup drawer and did my eyes up with eyeliner, mascara, and eye shadow. I again tried on several outfits including lingerie sets and took a lot of photos. I didn't do a proper job of cleaning the eyeliner off and she immediately knew I had done makeup. Her reaction was amazing! She said it looked like I had done alright and then showed me how to clean it off better. The next day she said that she was going to occasionally talk to me about makeup and that I couldn't use her eye makeup because it wasn't sanitary but had given me some items I could have for myself. I was positively giddy, and the next day she was gone for several hours so I had another session of makeup, trying on outfits, and taking pictures. I had tried on several wigs and liked a long brunette one the best, but then I found a long blonde wig that made my heart leap when I tried it on! I looked amazing and it had an aroma that intoxicated me. It smelled like girl! I'm certain that it was a combination of my love's perfume and body scent and it was amazing! I finally decided to start cleaning up because I knew my love would be home soon, I had just taken off the wig and clothes when she came home. I had locked the bedroom door so she asked me if I was dressed. I told her that I still had makeup on but was getting undressed. She said that she was feeling brave and wanted to see me so I said give me a few minutes and quickly chose an outfit that I thought would be good. I chose a black and pink spaghetti strap chemise and thong combo with a short pink checkered school girl skirt topped off with my heels and the blonde wig and of course my "veil". My heart was beating so hard when I unlocked the door and told her to come in! Her reaction was better than I expected and exactly what I had hoped! She told me I looked amazing and I basked in her compliments. She even had me try on another set of lingerie. She said I looked better than her, which I was a little afraid she might say, but I assured her that I didn't look better, just different. Anyway, it was a great experience and has me excited about the future! That was last Friday and I haven't dressed again since because I want her to see that it's a hobby and won't take over my life, but know that I'll get another chance soon!
