New Age Lifestyle

Hello everyone

I found this website by accident so why not tell my story? When I was 19 still living with my mom a certain feeling came across me that hadn’t surfaced since I was 7 years old. I started to pay attention to the clothes my mom wore to work each day. My mom works in an office so she always dressed nice.

One night after we had dinner I talked to her about the clothes she wore to the office. Unlike guys who would wear a suit with a different tie and shirt I noticed my mom wore something completely different every day. I talked to her about that concept. She told me about mixing and matching which helped increase her options.

My mom asked me why the sudden interest in her clothes. I wasn’t sure how to answer mostly because I really didn’t know the answer yet. I thought about it for a minute then asked what my mom did with her old dresses in the closet downstairs. My mom told me some of them she would keep in case the fashion comes back in style while others she would donate at some point. Without thinking I asked if it would be ok if I tried on some of the old dresses. My mom kind of looked at me with her mouth open then smiled and said sure why not. She asked me if there was a reason I wanted to try on her old dresses. I just said I didn’t know but something inside thought I should do it once in my life.

Later on we went downstairs where my mom showed me the different styles of dresses then she suggested I might try on certain ones but pass on others. With my mom’s permission I stripped down to my undies so she could help me try on my first dress. With each dress I tried on my mom commented on what she thought looked better on me than others. My mom pointed out that if I wanted to wear the 3 dresses she picked out it would be best I also wore a bra. I wasn’t so sure about wearing a bra so my mom showed me how bagging the chest area was since she has fairly large breasts. I said ok I will try it if she thought it best. A few minutes later mom returned with 2 bras and proceeded to try them both on me. One did fit better than the other so she put some socks in the cups. Mom pulled the dress over my head then zipped it up from the back. She took a look and told me I looked much better with some shape.

My mom wanted to know how I felt and was wearing a dress something I liked or was my curiosity over. I let my mom know I kind of liked the dress thing more than I thought. She asked if I wanted to try something else so I said ok. A few minutes later my mom returned with pantyhose that she helped me put on then a couple of pairs of high heels. I never tried high heels on before or wanted to. Mom helped me stand up in the pair that fit the best. She told me I had nice legs which made me turn red. I asked my mom if she was ok with me wearing those things. My mom let me know why not it was only her and me at home.

We went upstairs to watch some TV while I sat there in the dress. A while later I wanted to take the dress off mostly because I started to feel embarrassed. My mom helped me with the zipper so I hung the dress up downstairs.
The next night I kind of wanted to wear the dress again or one of the others. I asked my mom if I could try one of the other dresses and she said sure.
This time my mom brought down the bra again and panties along with the pantyhose. She told me to get the real sensation of wearing a dress I should wear panties. I was so embarrassed but I went to put them on along with the pantyhose. My mom asked me if the panties felt better than my undies. She was right the panties were nicer and when I put on the dress the total feeling of the dress with panties and pantyhose was really nice.  My mom told me she would like to buy me my own bra and panties if I was cool with that idea. She told me if I wanted to go with her I could pick out what I liked. I didn’t know much at the time about bras and panties. That weekend we went shopping for a couple of bras with smaller cups (B) and panties. We looked at high heels and when nobody was looking I tried some on.

Later on at home I tried on the panties and bra along with some breast forms. I put the dress on then asked my mom if she would zip me up. That was something she asked me to do many times so we laughed about it.

For the rest of the week I wore one of the 3 dresses every night and all day on the weekend. My mom convinced me to shave my legs and underarms which I did finally. We had some good talks about why I wanted to dress like a woman. My mom wasn’t for it or against it as she wondered why. It was hard for me to explain but it just felt right. My mom wanted to know if I wanted to be a woman or was it just the clothes. I let her know I didn’t want to be a woman but I wanted to dress like one. My mom talked to me about makeup, wigs and painting my nails. She wanted to get an idea how far I wanted to go so she could help me get there. Really I just liked what we were already doing since I never thought about hair and makeup. My mom wanted to know if at some point did I want to go out with her while dressed. I thought no thanks as it kind of scared me. My mom laughed a little then said good since she wasn’t ready for that either.

For the next month or so I dressed every day. My mom bought me a couple of dresses, blouses and skirts. She also made sure I had enough panties, pantyhose and bras. I started to wear night gowns while watching TV at night with my mom. In fact, she bought us matching nightgowns and robes.  My mom made me a deal that she would allow me to wear women’s clothing any time I wanted as long as I helped her around the house. I thought it was more than fair so she taught me cleaning, ironing, laundry and cooking. Every weekend we spent the day cleaning, changing beds, laundry, ironing and cooking. Our relationship became stronger as I learned more about what it was like to be a woman.
My mom surprised me with a wig one day that she helped me put on. She told me that I looked much prettier in the wig. I began wearing the wig every day. I always thought my mom knew best so I should always do what she told me. There were times when I didn’t want to get dressed which didn’t make my mom happy. The next day I would do something special her like a back or foot massage.

We always tried to keep the communication open like having sore feet from wearing high heels all day. Then the annoying bra straps at times. My mom continued to talk to me about what I liked and disliked.
One Sunday morning my mom asked me if I would let her put some makeup on me just so she could see what I would look like. I was hesitant but went along with it. My mom put false eye lashes on me, plucked my eyebrows which hurt like hell and did my whole face. A while later she gave me the mirror. I was stunned at what my mom did with makeup. She told me I looked very pretty. I looked again to see who was looking back at me in the mirror.

From that day on my mom taught me how to put makeup on just on the weekends. My mom asked me if I would go to the store with her one Sunday. I was like Mom, no way. She pointed out that I looked very pretty and from a few feet away I looked like her daughter. I tried to refuse but found myself in the car with my mom weeks later. She brought along a purse for me as we had practiced walking with a purse a few times at home. My mom told me she would teach me how to carry myself just like a woman if I wanted to learn. I was more into the clothes than trying to be like a woman. My mom told me some day I would thank her for showing me things that guys never learn about women. It’s a good thing I remembered it all because I was about to venture into the real world.
When we got to the store my mom talked to me for a few minutes about how to walk and she would do any talking. We got out if the car with my heart pounding. We walked through the parking lot then into the store. I pushed the buggy which was easier for me than walking right out in the open. All I wanted to do was run back to the car but my mom talked to me all the time we shopped. She kept telling me I was doing fine and how proud she was of me for trusting her.
We had agreed that if anyone said anything I was a transgender male to female. As it turned out only the cashier knew I wasn’t a woman. She said in a low voice I looked very pretty and my mom did a good job. I whispered thank you as I smiled.

It was a scary time that ended better than I expected. My mom was proud of me as she said once again on the way home.
The next day my mom asked me what I thought of going fulltime. I wasn’t sure what that meant so she told me I could live fulltime as a woman if I wanted to. I let her know I could never be a woman though. My mom agreed but she said I could live like one or as a sissy. My mom explained what a sissy was which was knew to me. I wasn’t sure about the sissy part after I read more about sissies.

My mom talked me into only wearing women’s clothing for a month. So each day I would get up and do the same things she did. My mom would go to work and I would work at home like the maid. At the end of the month my mom talked to me about how it went. We talked about the challenges like keeping my up with my makeup and shaving my legs and face. My mom talked me into trying it for 2 months just to see if I could handle life like a woman. Covid allowed me to take time off of work so I worked at home as my mom’s maid.

Near the end of the second month my mom and I talked again. I didn’t know it but she looked into working at her company as an office assistant. When she told me I was in shock. How could I work in an office looking like a woman. My mom told me her boss’s daughter transgendered to be a man. We talked about that for a while. My mom had talked to her boss Mary who was willing to have me trained if I was willing to come to the office dressed in women’s attire. I was in shock hearing all of that information. I never heard of any company willing to hire a crossdressing male before. I couldn’t say I was transgender when I wasn’t.
My mom was determined to have me work at her office. I agreed to go there on the weekend when nobody was there to scope out the place. On Sunday morning I got ready as though I wasn’t going to work in an office. We drove there and went in to the office. My mom showed me around and where I   would work. Just as we were ready to leave my mom’s boss walked in. My mom said hi Mary. I was shaking as I met Mary, mom’s boss. Mary told me I look very nice just as my mom had explained. We talked for a while in Mary’s office. I was scared to say yes to the job so Mary explained the environment to me. It was an all-woman department so I would fit in just fine. All the women that worked there knew of Mary’s transgender daughter. I just wasn’t sure after a couple of months I was ready to live that way all the time. My mom asked Mary if we could have a few days to talk about the challenges of a new job and working as a woman for me. Mary agreed that it was a big step and best to talk it over at home.
I always knew my mom had my best interest at heart. It was just accepting this new life would take some getting used to for me. My mom felt it best if we continued me living as a woman so we went out more often with me dressed as such. The more I went out with my mom the more I got used to how to carry myself and walk in heels. I watched other women and my mom which helped me a lot.

It had been a week since I met mom’s boss Mary. I thought it over and to be fair to my mom and her relationship with Mary I accepted the job offer. I know it was going to be a challenge but I had my mom to help me. We went shopping for a few more dresses, skirts and blouses along with another pair of pumps.
Monday morning, I was up early to take a shower, shave all over then get ready. Mom picked out my outfit for a first day at the office then finished off my makeup for me. We headed to the office together for my first day. Together we walked in a little early to meet Mary. We went over the paperwork then I was shown to my desk. My mom is a supervisor so she had one of her girls show me the ropes. I was surprised that everyone accepted me for who I was on day one. By the time I realized it the day had come to an end. Mom talked to me on the way home about how it went for me. She was interested to hear how I felt working in an office full of women while I was dressed as one of them. I let her know I was a little embarrassed each time I was introduced to someone. It got easier though as I learned my role and the roles of others.

Jumping ahead it’s been 3 months working with mom at the office. I quite like living this way far more than I could have ever dreamed. Although my mom never pushed me hard she did help me when I had questions or issues. I quit my old job which wasn’t that great anyways. I have decided to keep working with my mom and all the wonderful ladies at the office. I have become friends with several of the ladies. So many of them have complimented me on my decision to live like a woman and they like how I dress. My mom has good taste in fashion so she has taught me how to look good at the office.
The next step for me is to grow out my own hair instead of wearing a wig. I have decided to live this way fulltime because I like it very much. My mom and I have talked about me taking hormones so we have a doctor’s appointment next week with Mary’s daughters doctor. She specializes in transgender patients so she would be the best doctor to talk with about me going on hormones.

I hope you like my story. I am interested to read about others who live as women or as sissies.
Thank you,
Charlene 
 
 

Congratulations Charlene on an incredible journey so far. You have an amazing mother who saw the feminine side of you come out the first time you tried on one of her dresses. Women have this ability to see through boys and men when it comes to their hidden feminine side. I know as my mom helped me too.

Enjoy your new life day by day. It only gets better with time.

Kim

Beautiful story you are so lucky ,wish this happened to me

Hi Conway

Thank you for your lovely post. I don't have time to address all of your points since it is housework day for me. Life before now was a little boring with some confusion on where I was headed. My mom and I have always been close which helped get us started on this new path together. I am not familiar with the Good Wife but will in time check it out. My mother and I settled on The Vice last week because she felt more than I chastity was needed. I will agree with you on day 4 I was ready to climb the walls. My mom told me it would take a while to get used to it and for my mind to settle down. So far she was right in that I kind of talked myself into accepting it to avoid bugging my mom to take it off. I like the commitment bracelet although my mom bought me the latest Apple watch for Christmas that I will all the time.

Alright that is all I have time for today. My mom is shopping and I have housework to do before going back to work tomorrow. Oh, I actually like my job and the girls in the office have been so good to me. They like the clothes and shoes I wear, thanks to my mom's excellent taste in fashion.

Bye for now
Charlene

Hi Conway,

Mom and I listened to the video you shared. It was very informative and mom liked it too. I also listened to the one about chastity since that is new to me. I think I learned more about how us guys work than I knew before. My mom and IO are going for lunch with a couple of the girls in the office now. It will be another new experience for me to go to a restaurant dressed as Charlene. My mom told me nothing to worry about since she knows  the people there.

Bye for now
Charlene

Well thank you so much for the kind words. It's been quite the journey so far working with my mom and being accepted by the other girls in the office. I only wish my mom and I had done this years ago. The only part of living as my mom's daughter is the chastity device on my clit. I have gotten used to it but still prefer my mom never bought it for me to wear. I will say mom has been pretty good about allowing me time to remove it for cleaning and shaving. Next month mom told me to get ready to be waxed. My mom would like me to be waxed instead of having to shave so much. Ouch is alll I can say.

Hello Charlene: Thanks so much for the update. You have both a lot to be proud of, and a lot to be thankful for.

Regarding waxing, the discomfort is temporary, the sensation will last a month or more. You will love how your clothes just glide across your skin. If you don't have something fun to wear around the house, like a bodystocking or catsuit, now is the time to get one.

Salon technicians are professionals and are non-judgmental, so I hope you wear your chastity to the salon, and your mom is present for the treatment, removing your device only as long as needed for your bikini area wax.

As for chastity, it took me about 2 weeks to get so accustomed to the device that it actually felt strange, and a bit like a weakness and betrayal, to remove it. It helps you focus your energy on things that are important (like pleasing your mom and co-workers, housework, etc.) and should make you feel more submissive, easier to manage, and lighter on your feet.

I always think of the scene in "The Story of O" where O looks glowing and adoringly at her training mistress when her corset is tightened. The chastity should give you similar feelings of warmth and gratitude. I hope you are proud of your accomplishments thusfar and encourage your mom to keep you in chastity. Perhaps your next foot rub can be extra special, and you can discuss your feelings openly, being vulnerable, and without reluctance. Hopefully your mom has at least one close friend who knows the full extent of your relationship with her, and can work with you, building confidence and making your journey as comfortable, and feel as right, as possible.

One suggestion. A new type of tattoo ink looks authentic but fades after 9-15 months. You might consider getting a lower back tattoo of a feminist symbol along with your mother's initials or first name. It would be quite a symbol of devotion and a great conversation starter. When it fades you can have it renewed, or eventually replaced with your wife's name, or the names of a lesbian couple, if you are ever managed by one.

Attached is a symbol often associated with wife-led marriages and female supremacy/gynarchy. There are others, but this is my favorite.

More info on the ink is here. https://ephemeral.tattoo/

THANKS again for the update and please keep in touch here. Your posts are very inspirational, and could help others who are just getting started.

Regards,

CONWAY

Hi Charlene

You write wonderfully and from the heart which makes your story so wonderful. It honestly sounds like you have hit the ground running even hough wearing heels. Well Done Gurl  You seem to be happy with how things are going and I suspect that the positive reaction by those you meet is down to that happiness, I hope it continues for the future as the world needs happy people. One caution though - you have changed a great deal in a very short time and, even if you don't start hormones, other things will change too. Be ready and open to this as you have shown you can and it will avoid many issues down the road. People like us are a work in progress and find it easier to improve with a good attitude, you may be amazed when you look back in a year or two and see how much has changed for the better.
I wish us all a great future which we all deserve.