Recently our house burned down in CA with a lot of other houses. We lost everything, house, furniture, clothes. I am a Teen Male and was sent to my Aunts house in NorCal to stay with her, while my Mom and Dad figured things out.
She is a nice lady, and I like her. When I arrived, I was wearing gym shorts and a T-Shirt all I had, and they were dirty and smelled like smoke. She ordered me into the shower and said she would wash them and find something to wear and put it on the bed for me.
So I took a hot shower and got clean. I got out of the shower and walked into the room and there was a sundress and p****** on the bed. I was standing there thinking WTF, with a towel wrapped around me and my Aunt walked in and said she was sorry, but she was single and had no male clothes or clothes that would fit me. She apologized and asked if I could just wear this for now.
But it is a dress and ladies underwear I said. She said well we will have to go shopping and get you some clothes, please just get dressed in this for now, or else go naked until your clothes are washed, and she lefyt the room.
I really had no choice, and picked up the yellow nylon p****** and put them on. Now I had to put the dress on, it was a sundress with flowers all over it. I felt weird wearing a dress and p******. I walked out to talk to my Aunt and she smiled and said I looked wonderful and gave me a hug, which was kind of weird.
We had coffee together and talked about the fire and stuff. She asked if I was ready to go shopping and get some clothes. I said not not, wearing a dress and her p******. She took my hand and said you look nice in the dress and I was hoping you might want to wear it for me while we shop for you. It is not a big deal, and it would make me very happy.
No idea why, other than she was being really nice, but I agreed so I could get some regular clothes to wear. So out the door I went wearing her dress and p******. She drove us to a ladies clothing store! She said she needed a couple of things quick and then would go to another store for my things.
We went into the ladies store and one of the clerk recognized her and came over to say hello. She introduced me and I am sure I was bright red with embarrassment wearing her dress. The two of them talked alone for a few minutes and the clerk started running around the store and gathering what my Aunt needed I guessed.
A few minutes later, my Aunt asked me to come to the back of the store wear the clerk was with her items in hand, and she explained to me that I looked so nice in the dress today that she wanted to get me a few more things in my size to wear around the house. The clerk held up 2 more dresses, and more p******. There were even 2 bra’s in the pile of things. I objected, but then my Aunt hugged me again and whispered in my ear that it would make her very happy if I would try on these things and let her buy them for me.
I still have no idea why, but agreed reluctantly to go in the fitting room and try on the items. She insisted to see me in all of it to make sure they fit properly. So one by one I tried on the bra and p******, and put a dress over it all and walked out to show my Aunt, and the clerk too! The sales clerk was adjusting and checking the fitment, and pulled the top of the dress down to adjust the bra straps. Being exposed in female underwear and a dress and being touched so much by the clerk got me excited and I had an erection that both of them could see sticking straight out under the dress which was a little short.
My Aunt was smiling and said you look wonderful and you make me so happy. She purchased all of the items and told me to pick my favorites and put them on to wear out of the store. Bags in hand, I walked out of the store in a short dress wearing bra and p******. My Aunt was so excited, like she had a dress up friend or something. Rather than go to another store for boys clothes she took me home. I said what about getting other clothes. She said You look so good in the new clothes I hoped you would just wear these for me while staying here. Nobody will know, and you will make me so happy.
So I have been here for 10 days now, and dress up for her in bra and p******, and the dresses she purchased. She told me that girls don’t have erections, and it does not look so good, she has been helping me with that. Because she has been helping me make it go away and get relief and have started enjoying dressing up for her everyday. I dress up, and helps me get relief. She has now got me nylons and girls flats to wear with my dresses. She even showed me how to put on light makeup and style my hair better so that I look more like a girl.