I can remember it like it was just yesterday. I had just turned eighteen and was still living at home with my mother and my older sister by a year. My father had passed away suddenly a few years before, so it was just the three of us at home.

My sister and I shared a bathroom in our small house, and as I went in to brush my teeth, I saw a pair of my sister’s baby blue nylon panties sitting on the counter. She must have dropped them there after taking her shower earlier in the evening.

Something came over me, and I had an incredible urge to pick them up. They felt so soft and slippery to my touch, and I felt a stirring between my legs as I ran my fingers over the silky fabric. I don’t know what came over me, but I just knew I needed to try the pretty panties on. I unzipped my jeans and pushed them and my boxer briefs down my legs and stepped out of them. I bent over and slid one foot and then the other into the panties and slowly slid them up my legs. The feeling was divine as I pulled them into place over my quickly hardening member.

I stepped back and looked at myself in the mirror and really loved how they looked, and especially how they felt, against my skin. I had never considered wearing anything of my sister’s before, but here I was, admiring myself in a pair of her silky nylon panties. I slid my hand down across the front of the panties and uttered a slight moan as I rubbed my hardening cock through the sexy fabric. It wasn’t long before I erupted and shot a huge load of cum into the panties. Afraid that I would be caught, I did my best to clean off as much of my cum as I could from the panties and then dropped them into the clothes hamper. I promised myself that this was a one-time occurrence and that I would never do it again.

It did not take long to break that promise. 

I kept replaying that night in the bathroom in my head. As much as I wanted to forget about it, I could not shake the thought of wearing my sister's panties and how right it had felt. Each time I did, it made me long to try on another pair of her panties.

The next week, my mother and sister went out together to do some shopping, giving me free rein in the house. This was my chance to try on another pair of her panties. As soon as they left, I crept into my sister’s room and went straight to her dresser. Pulling open each drawer I finally hit the jackpot with the third drawer I opened. There before me was an incredible selection of pretty nylon panties in a variety of colors. I ran my hand through the silky stash and my cock started to stiffen again. I found a very pretty white nylon bikini panty with lace around the legs and a pretty bow in the center of the waistband.

I went back to my room and quickly undressed and slid the panties up my legs. Again, once they crossed over my shaft, I became rock-hard and incredibly turned on. I slowly stroked myself through the silky panties. It was not long before I felt myself about to cum. I quickly pushed the front of the panties down so I would not make a mess in them as I had previously done. Within moments of doing so, I shot an incredible load of cum on my stomach and chest. I lay there momentarily to regain my senses. Once I did, I quickly cleaned myself with some tissues and removed the panties. I got dressed again in my own clothes and quickly put the panties back where I had found them. 

This went on for several weeks as I tried on many pairs of my sister’s panties whenever I had a chance. I even got brazen enough to tiptoe into my sister’s room to grab a pair of her pretty panties to wear while she or my mom was also in the house.

As this continued, I soon got careless with my actions. I did not notice that my sister and mother were coming up the hallway at the same time I was exiting my sister’s room with a pair of her panties in my hand. I almost ran right into them. There I stood, frozen, not able to think of what to do next.

My sister looked at her panties in my hands and asked, “What on earth are you doing with my underwear?”

She grabbed them out of my hand, and then asked my mother, "What she is going to do about this?"

My mother then took me by the hand and led me to the living room while my sister went to put her panties back in her room. 

My mother sat me on the couch and stood in front of me for a few minutes, tapping her foot. She was obviously considering what she should do about her son sneaking into his sister’s room to take her underwear for who knows what, but she was determined to get to the bottom of the situation.

She finally asked, “What were you doing with your sister’s underwear?”

I knew there was no way out since I had been caught red-handed. My face turned red, and I mumbled, "I like how they look and feel when I put them on."

She looked at me for a moment and then asked, “How long I have you been wearing your sister’s panties?”

I could not look her in the face, so I looked down and said, "I have been wearing them whenever I have been alone over the past few months."

Then she really embarrassed me and asked, “Do you touch yourself while wearing the panties?”

If I thought my face was red before, it must have really turned bright red at that moment. I was too embarrassed to answer.

“I’m waiting for an answer, young man,” she demanded.

I just slowly nodded my head, wondering what I had gotten myself into.

“Boys do not wear women’s underwear. What am I going to do with you?”

My sister then walked into the room. She had been sitting just inside of earshot and had heard everything that had been said between my mother and me.

“If he really likes wearing women’s panties you should get him his own. Then he won't need to sneak into my room to borrow mine.”

My mother said, “What do you mean? Are you OK with your brother wearing women’s panties? What will everyone think if he is ever caught?”

My sister went on, “If he has been wearing my panties for months, do you think he will really stop now? I do not want to always be wondering if my brother has been wearing my panties, especially if he is jacking himself off while wearing them. Better to get his own so he can wear them whenever he wants. Maybe that will stop the mystique of wearing them. If not, he will have his own to wear whenever he chooses.”

I loved my sister for that. Here I was just caught admitting to wearing her panties and masturbating in them. She was really standing up for me.

My mother just stood there for a moment looking between my sister and me. She finally looked at me and said, “Is that what you want? Do you want panties of your own to wear?”

I slowly nodded.

My mother just shook her head and walked away. I looked at my sister and thanked her for backing me up.

She just smiled and said, “No wearing my clothes anymore, OK?”

Nothing further was said on the topic that night. I kept to myself as much as possible to avoid further embarrassment. The next day I had some errands to run and was not home until late in the afternoon. I was hoping this whole mess would just be forgotten. I said hello to my sister and mother as I walked into the house. I then went up to my room. As I opened the door, there sitting on the bed, were five pairs of nylon panties in different colors. One in black, one in white, one in red, one in baby blue, and one in pink. All of them had pretty lace or bows to make them all the more feminine.

I turned and my mother and sister were in my doorway watching my reaction.

My mother said, “No more borrowing your sister’s underwear. If you want to wear panties, then you will wear your own from this point forward.” 

That was just the beginning of my cross-dressing. There was soon more to follow….