How to get started

I'd like to get started in some subtle way to become more feminine. Something I could start doing or wearing when I"m alone at home, and more subtle things at work or in public, maybe starting people to wonder ? I'm an older man, approaching sixty, and used to love wearing sun dresses as a kid when I"d play dolls with my sister and her friend. Recently I"ve become interested in being a bit of a sissy or cross dresser.

Any ideas ?

I enjoy satin/nylon panties as daily underwear that might be a place for you to start.

I also like wearing dresses and nightgowns around the house and sometimes outside late at night to take the trash out, I try to not make it obvious if someone happens to come outside.

Hope this helps.

If you're alone, at home, you can wear anything you want. If you're into female outerwear you can find all manner of clothes! Your first problem is sizing. Try on lots of clothes until you know what fits. I think skirts, low cut tops, and sleeveless, tank top styles are feminine that no man would wear. Lingerie: sky's the limit. If you want to shop--spend money--on lingerie it'll be a lot of fun.

In public is different. What people think is important. If you don't mind everyone knowing you crossdress, you can do anything you want. Everyone looks at your clothes--especially women. If you're wearing women's whatever you will get the cross dresser label. Not a good idea at work. Now everyone is LGBT tolerant, and if you get the 'pervert' label, you livelihood is in danger. Take a trip somewhere, and try something easy like women's pants that vaguely look masculine, loafer shoes & nylon knee highs. Panties of course--as they can't be seen. Then get braver and wear more obvious feminine clothes.

"Recently I"ve become interested in being a bit of a sissy or cross dresser."

You need to start with your comment. There seems to be a growing distinction between sissy and cross dresser. I'm not going to get into details about it, it's more fun to research it on your own. That said, you have to ask yourself, are you a slut on your knees servicing a man or just lounging in women's clothes.......

I got started wearing panties and also had my first orgasm at the same time. I often stay for weekends or vacations with relatives. my auntie my mother's youngest sister. She has two daughters and a step daughter. When I stayed there the two younger girls and I often slept in the same bedroom and sometimes in the same bed. the room had a queen and a king size bed. So, one wrong weekend I was there. we all went to bed. I was in with the girl cousin who is almost same age as I. During the night I wet the bed. This had happened to me a lot before and all we did at home was change the sheets and I'd get clean underwear and pajamas. This time when I got up my aunt had come in and saw what happened. My cousin had felt it and moved to the other bed during the night. My aunt told me to go into the bathroom, take all my clothes off and give them to her and take a shower. I did so and dried myself and emerged with one of my cousin's bathrobes on. The girls and I are all about the same size. My aunt came in to check on me then she went over to my cousin's dresser and took out a pair of panties. She gave them to me and told me to put them on since my other underwear was being washed. I went into the bathroom with the panties. I had always liked watching my cousins walk around in their panties and I knew they wore them under their pajamas at night. I started to pull the panties up my legs. They were nylon, pink with a lace band down one side. They fit perfectly. When I went out my aunt asked how they felt and I said "good. they are a little tight." She told me they are supposed to be tight. I put my shorts and shirt on and wore the panties all day. When I was putting them on I started to feel something very different and very pleasurable. After wearing them a bit my cock started to get hard. This was the first time for the hardness and the pleasure. The girls and my aunt were in the kitchen and I excused myself and went back to the bathroom. I took my shorts off and started to stroke my cock through the panties and as I did the feeling got more and more intense. It wasn't long when the sensation was super intense and I felt something starting to happen in my cock. I pulled down the panties and started to stroke it and in a matter of seconds I felt like I was exploding. I watched the cum shoot out of my cock. After I calmed down I just sat there and then wiped the cum off my cock with a washrag. Some had gotten on the panties but I just pulled them up and went back into the kitchen. My aunt asked if I was OK and I said yes but I now know she guessed what had happened. That night before bed my aunt came into the bed room and told me she had talked to my mom and they decided I needed to be diapered. She told me it was OK because the youngest girl, my age, also wore diapers often for the same reason. she told me to talk of the panties and lie on the bed. She put the diaper on me and then had my cousin get her a pair of her plastic panties. She gave them to me and as I was pulling them on I started to get the same feeling as in the morning. The plastic panties were tight but when I got a hard on it wasn't obvious because of the diaper. I had to wear a diaper every night. I asked my cousin if I could keep on wearing her panties and she said she was OK with it. So, I was diapered every night and wore panties every day. That started me off with my need to wear panties every day. To make a long story short, it also led me to finally admit that I had always wanted to be a girl so a couple years later I started the transition.

I was started with panties at age of 5 by my mom.She let me wear them after seeing wearing girls nexted door . I think easiest way to start and feels so good

Dtart eith panties, you can wear them under your cloths if out, or under a dress if home.