When I was younger, I used to go to my sister's bedroom and look through her things. They were so soft, I loved to touch them. When I was about 14, my sister got a promotion at her job but it made her work long hours and I often had a lot of time to myself. One day I decided to try on some of her things. I was not very big, so her clothes fit me nicely. I loved the way her panties felt against my skin. I loved to move my dick back and forth inside them. The feeling was indescribable.
After a while, the panties weren't enough and I started putting on her bra. I used washcloths to fill it out because I liked it that way. If I had a lot of time, I'd put on one of Lil's sweaters so I had bumps like the girls in my school. I didn't wander around much, just stayed in Lil's room and put on her clothes and looked at myself in her mirror. It felt so good, I'd soon have to grab a Kleenex and jerk off so I wouldn't soil her clothes. I was always careful to put everything away properly.
One day, I was sitting there in just a bra and panties when the door opened and Lil walked in. I saw her in the mirror and I think I may have fainted because the next thing I knew, Lil had her arms around me and was holding me and I was crying. I wanted to go away, but I couldn't move. Lil held my head against her breast and rocked me. She kept saying, 'It's OK, Billy. It's OK'.
After a few minutes, while I was still crying, Lil put her hand in my lap. I felt her fingertips slide softly across her panties and my dick. I was frightened and ashamed but it felt so good my dick started to stiffen. Lil moved her fingers along the shaft, and then moved it so it slid against the soft material the way I did when I was playing with myself.
In no time, I was hard as a rock. Lil kept stroking me gently and, all of a sudden, I exploded. I didn't have time to grab a Kleenex, I shot everything into her panties ... At the same time, Lil started to croon, 'Me, too, Billy. Me, too'.
Hugging me against her breast, Lil slid her hand under her skirt and into her panties. She kept whispering, 'That's OK, Billy. Me, too.' as she moved her hand, slowly at first and then more and more furiously. I could hear her fingers move, like water hitting the side of the tub. As she kept moving her hand, she kept whispering to me, 'It's OK, Billy. It's OK. Me, too.'
Then her whispers got louder and more breathless as she straightened her back, and shoved her legs out, and I could see and hear her hand moving inside her panties in all directions and she sort of groaned and said, 'Oh, Billy. Oh, Billy. Ohhhhhhhhhhhhh!!!!
After that, we sat quietly for a while. Lil held me close and I buried my head in her breast. The cum in the panties got cold and I wanted to take them off, but I was afraid to speak or move. I didn't know what to say. Lil stroked my hair for a while, and then said, 'C'mon, Billy. You'd better get cleaned up. Here. Let me help you with that.' and she reached behind me and unhooked the bra. 'Just put these things in the hamper.' When I stood up, she turned me around and kissed me on the forehead, saying, 'You're a good boy, Billy, and I love you very much.'
Just before I went to bed that night, Lil told me she would pick me up after school. I didn't ask her why, I just told her I'd see her in the parking lot about 3:15.
The next afternoon she picked me up and we went to a diner about a mile from the school. It was practically empty since it was mid-afternoon. We went to a booth in the back and Lil ordered two hot fudge sundaes. We didn't talk much until after we ate the ice cream. Then Lil asked me how long I'd been wearing her undies. I was too scared to answer, but Lil told me it was OK. She wasn't angry but she did want to know a little more about what I was doing. I finally admitted that I'd been looking at her things for over a year, but that I didn't start wearing them until this fall, after school. She asked me if I liked doing that, and I admitted that I did. She asked me if I knew that men wearing women's clothes was fairly common. I told her I didn't think so, and she assured me it was true. She told me about a woman she knows who enjoys helping her husband dress in lingerie. She said the man was a macho individual, but he liked to wear soft things. He wasn't the only one, by a long shot, but he was the only one Lil knew personally. His wife told Lil he was a better lover when she dressed him up.
After we talked for a while, Lil asked me if I would like some of my own things. She said she didn't mind me wearing hers, but she thought I'd enjoy it more if I had my own. She said I must have been very careful when I was wearing her things and she was sure it would be more fun if I had my own things and didn't have to be so careful. I couldn't answer her, so she told not to worry, it was fine with her, either way.
After we left the diner, Lil drove downtown to a store. We went to the ladies' department where Lil bought quite a few things. She asked my opinion a lot, but she seemed to know the things I liked even better than I did. Just before we left, she bought a beautiful brown-haired wig.
When we got home, we carried the things to her room. Once there, she picked two drawers in her dresser and moved all her things to other drawers. Then, we put the new things in the two drawers she'd just cleaned and put the wig on a stand on her dresser. When we were all finished, she said, 'There. Those two drawers are yours ... but only you and I know that. You can come here any time you want to. Would you like to try them, right now?' Again, I was tongue-tied and couldn't speak, but I must have nodded because she said, 'OK. I'll help you. First, let's get you a shower so you're nice and clean. They'll feel even better that way.'
When I came out of the shower, she had one of her big soft towels and dried me off, all over. Then, still naked, I followed her back to her room. She sat on the edge of the bed and waited while I went through the new things and picked out panties and a bra that I liked. I put the panties on first. When I tried to hook the bra, Lil came over and helped me. Then, she reached in the drawer for a package I hadn't noticed and took out two large pieces of foam that she slipped inside the bra. It was incredible. The bra looked like it was real. More than that, the sight of it made my tiny nipples swell up until they touched the foam. I moved the bra a little bit, as if to adjust it, but really to feel it rub my nipples. It excited me so much I was instantly erect.
Lil said, 'OK, Billy. I have to go out for a while. Enjoy your things. You can play with them as long as you like. You're a fine young man and I'm glad to see you growing up. I love you, Billy, and I'm proud of you.'