Skye135’s Diary

Dear diary,

Now that my mom knew I was wearing panties and didn't care I really wanted more add some variety to my wardrobe. I was nervous to go shopping for something like this, so at 1 or 2 am I decided I would go to Kmart to see what they had.

The store was empty, only employees running around. I went to the show isle, and I could see the entire area where they had tons of panties on display. After working through my nerves, beat red in the face, I walked into the middle of the giant area.

They had so many. Bikinis, boy short, thongs, and g-strings. I spent some time browsing. I picked out quite a bit. I got 4 pairs of satin bikini panties from joe boxer (so cute) they had a wink face on the right hip. I got them in black, white, yellow, and pink. I also found a cute string bikini, with purple straps on the hips and leg openings, that were a metallic silver with glitter and sparkle star designs on them. I also got a few thongs of random colors and patterns, as well as a g-string. My arms were full. Probably 20 pairs.

While I was focused, 2 ladies about my age had come into the area. One was bouncing around with excitement singing about thong shopping. She turned around an I was right there, arms full of panties. She stopped, grabbed her friends hand and went around the corner. I could hear her laughing, saying that boy is buying panties to wear, and saying I was a weird gay guy.

At that point I left the area. Now my next big step. Checking out. I'm sure I was beat red. I put the panties on the belt. The lady looked at the panties, then looked at me, the said did you find everything ok. I told her I did. She probably knew I was embarrassed, about half way through she held up the pink satin pair as she scanned and said they were cute, I said yeah, then she held up the string bikini and she said they were a bit flashy and cute. I said thanks. She finished up and asked me if they were for me. I told her they were. She said if I ever needed to shop privately for them that I should look to see if she's working.

About 3/4 of the way through those 2 girls got in line behind me. They were giggling the entire time ask the cashier scanned them, then transferred them to the bag. So they seem everything I was buying since they got there.

I made my way out to my car, in the parking lot the louder girl yelled are you going to wear those?, I responded with a head nod yes. They both started busting out laughing at me. I couldn't fully make out everything that was said that night, but I do remember heard fag and I bet he has a really small dick.

Over the next few weeks I started to wear them, my mom didn't say anything, I just went on as usual, put my clothes in the hamper, they came back clean and folded on my bed, panties on top. My mom did say she liked my satin ones, and asked where I got them, so I told her.

Dear diary,

Now that I had my own panties, and a few bras I began to wear them every day. At first I was only wearing them at home, every so often I would toss a bra on. I had to learn to do laundry, that way I could go undecided from my parents.

Eventually I started wearing them to school. I tried to keep a keen eye on what other girls were wearing, that was the advantage of low rise fashion. I really liked string bikinis and thongs, they were so cute, and I had a big thing for Victoria secret panties with the logo on the waistband.

Eventually, I hit a point to where my parents didn't go out for a long time. I ran out of panties and bras to wear. I was going commando, I really didn't want to wear boys underwear again. My mom eventually noticed that I didn't have underwear in the laundry. When she confronted on where my dirty underwear was I told her that I haven't been wearing any.

That's when something unexpected happened, she looked at me and said she wasn't talking about my boy underwear. I literally froze up. I felt my face turn beat red, thats when she told me to hurry up and give them to her because I need to wear something. So I got into my little baggie in the closet and gave her all my panties and bras.

I hid in my room all day, embarrassed, and scared. Eventually she returned with the laundry, she walked over to my drawer, grabbed all the mens underwear, put them in the hamper, then took the bras and panties and put them in the drawer, she said I won't be needing those anymore.

From that day forward I only wore panties.

Dear diary,

My sister had gone off to college. I stole some of her panties to give me something to wear while she was gone. Unfortunately it wasn't enough. She came back for winter break and I immediately jumped into her bags for some new things to wear. Her style changed, it was the first time I had ever seen a thong.

For a few years I had gotten more and more bold. I was wearing panties fulltime, and I had gotten caught by her and my mom a lot up to this point. In all honesty I wasn't really hiding it anymore, I knew I wanted to be a girl.

A week or so before she was supposed to return to school our mom sent us to the mall to do some exchanges and to get a few new things for school. We spent a few hours shopping and returned to the car. 

We got in and I don't really remember what I was looking for, but I put my knees on the seat and stretched into the back, I wasn't mindful of the situation, the next thing I knew my sister immediately asked my I was wearing her panties.it caught me by surprise, I wasn't expecting it. When I stretched out my panties came out of my jeans 

She asked me 2 questions. The first was if I was gay, which I had no response to atm, and answered no. The second was if I wanted to be a girl, which I told her I did. I was petrified after that. 

She calmly told me that we were going to go back in the store to get me a few more things. The deal was that if I got my own underwear I was not allowed to wear hers anymore, and that if I needed new ones that I let her know.

In the store she said that she noticed that the only time I show interest in clothes shopping is when I'm in the women's clothes. We got 12 panties and 4 bras that day. I also honored our arrangement until I was able to drive and get my own things.

Dear Diary,

Getting caught was both a way for me to let others know that I am this way, and it aslo provided a little sexual gratification. I started wearing my sisters panties a lot more frequently. The goal was every single night I wanted to wear them.

I was sneaking into either the laundry or my sisters room while she was at practice (for sports) and I would go through her panties and pick a pair that I was going to wear that night. Then after dinner, I would go to shower. It started out as usual, I got undressed, kicked my clothes into the corner and put my new clothes on the end of the counter. I generally put the panties I was going to wear in the legs of my pants. I think on that day they must have not fully been in pants that day.

While I was showering my sister came in to get something off the counter. She was in and out. When I got into the shower I started getting dressed, I noticed that the panties were gone. I thought I dropped them or something. I took forever tearing apart the bathroom looking for them and I was unable to find them. I was stressed beyond belief. I put my clothes on, no underwear, and walked out of the bathroom.

My sister was sitting on the edge of our parents bed with her panties in her hands. All she said was "looking for something." I said no, then went about my evening. I waited for her to start her shower. Thats when I went into her room again and got myself a pair of her panties to put on.

It will go on like this for a while before I switched to panties full time. I really liked wearing womens panties, and it made my gender dysphoria subside some until it was time to take it further.

Dear diary,

I remember being 13, sneaking into my sisters room, opening the dresser drawer up, looking at all of her panties. I shuffled through them, thinking to myself that I liked everything she had. I settled on a blue pair, ribbed, thicker satin. It really compressed and flattened out my penis, like it wasn't even there. I was so happy.

I kicked back onto her bed, I positioned myself with my knees up and spread out, and began to rub myself through the panties. I came so hard to the thought of being a girl, to the thought of wearing panties.

I made up my mind at that point that I wanted to wear them all the time, that I wanted breasts, I wanted a vagina, I wanted to be a girl.