I am hesitant to post this, as it is my personal story. I am sure I have embellished some parts, though this part is as true as I can remember. As usual, the names have been obscured. This is not about porn, it is about experiences... though I do still get quite hot writing about it.

It is necessary that I state this all happened among consenting adults. Any inference otherwise is purely your own interpretation.

I hope you enjoy.

Tracy and Margaret were living with their Nana for the summer and Nana was not able to walk very well. She had one of those stairway automated chairs she had to use to get up and down the main stairs. That meant that Nana could no longer easily go either down in the basement, nor up in the attic. Those were the obvious places for Tracy, Margaret and I to go and play as we got to know each other. I was the first one to get to know the girls — Scott was really rather shy, in a boisterous boy-way. Anything potentially embarrassing was put off onto someone else, and most of the time he would refuse to have anything to do with playing with girls anyway... Despite being curious, he was also very chauvinistic, though I didn’t know that at the time. Since I lived next door, and my parents knew their Nana, it was easier for me to get invited over to play with them – in fact, I was often sent by my mother, so I actually got to know them quite well, way before Scott did.

The girls suggested the basement right off. It was full of all kinds of old furniture, boxes, mirrors, and so on. We wandered around between the stacks of things and found blankets and sheets and made narrow passages between boxes and old chair backs. We would throw old sheets and blankets over the paths and make extensive forts to run around in and play house. It wasn’t long before the girls started getting curious and touchy-feely with me. It was summertime and we would get hot running around down there, so I would take off my shirt. Margaret asked if I would mind if she took hers off too, and I just shook my head, amazed that she would do that. Nana called down for Tracy to come upstairs for some reason, and we all froze. Tracy yelled back, Okay,” and said she would be back soon. After Tracy left, Margaret took off her shirt. She had tiny little budding breasts and her nipples stood up hard. I couldn’t help but stare and she said if I wanted to I could touch them. I reached out and stroked her left breast and immediately got very hard in my pants. I wasn’t sure what to think... I was so curious and excited and I wondered what they would feel like, but also to have them myself. Margaret said she wanted to know what a boy looked like “down there.” I was so excited, I was actually shaking a little bit. I was also embarrassed because I was really stiff in my underwear. I swallowed hard and said, “I’ll show you mine if you show me yours.”

She didn’t even say anything, she just took off her pants and stood there naked except for her pink panties. I unbuttoned and unzipped my pants slowly and took them off. She was staring at me and I was staring at her. She looked up and nodded her head, then slipped her fingers into her panties and pulled them slowly down to her knees. I followed suit and stood up. Her eyes got real big and she asked if she could touch me. I shook my head yes and she reached out and grabbed my little hard dick. I must have jumped a little since she pulled back, so I said, “Just be a little careful, its real sensitive!” I wanted to touch her too, so I asked and she said, “Okay,” and I reached out and carefully put my finger on her slit. She said I could rub it gently up and down some if I wanted, so I did and we were doing that to each other when Tracy started back down the stairs.
I jumped again and reached for my pants, but Margaret said, “It’s just Tracy, and she’ll get naked too, besides, Nana can’t come down here.” Tracy found us with our underwear back up, but she got scared that Nana would find us. Margaret talked to her and calmed her down, then said how fun it was, and that we could run around down here naked and no one would ever know. Tracy wasn’t sure about all this, so she said, “I’ll do it if he gets all the way naked first.” Margaret looked at me and smiled, and I said, “Okay,” and took off my underwear. There I stood, completely naked to two girls I had really just met... with my little dicky sticking straight out. Tracy giggled, but began taking off her shirt. She was a little older, if a bit less smart than Margaret, so she had bigger breasts. She quickly got down to her panties, but didn’t want to go any further. I reached out and tickled her, calling her “Chicken” and then ran down the tunnel of boxes and sheets we had made. We all started chasing each other and giggling until we had to stop and rest. I was starting to feel like one of them, another sister in my mind, but it must have been obvious to them I wasn’t.

I wasn’t really as excited anymore then, so they got all curious about why it got small. Of course, just looking and talking about my little peenie made me get all stiff again, much to their delight. Margaret got an idea and ran back to our underwear, picked it up and brought it back. She put on my white Jockey shorts, giggling and said, “See, I’m a boy!” Then held her pink panties out to me and said, “Put them on!”

Tracy just stared, and I was really getting all excited again at the thought of putting on Margaret’s panties. If my dickie could have gotten any bigger, it would have! I took her panties and she helped me turn them around, cause I wasn’t sure how they went. I pulled them up and they snugged my little hard dick off to the right and really accentuated it. I had never worn anything so tight that held my dick so firm. I must have turned very, very red, because they started laughing and giggling harder and harder and were saying “Look, he’s a girl! He’s a girl!”

That was when Nana called down for them to come up for supper. Margaret quickly pulled her pants back on, right over my underwear and Tracy was getting dressed very quickly too. I just kind of stood there and then looked around for my pants, which were on the other side of the room. Margaret said “Just go out the basement door when you’re done” and they both ran upstairs.
I found my pants and then realized I still had on Margaret’s panties! There was nothing I could do but just wear them... at least, that was what I thought. So I pulled up my pants right over those tight little pink panties, zipped up my pants, put on my shirt and let myself out.

Just wearing her panties felt so good and kept me so hard, I had a time hiding my little boner from my mom. I also had to eat dinner, but afterwards I could go back out for awhile or stay in and watch TV if I wanted. That night I decided to stay in so I could hide Margaret’s panties and change into my own undies, so my parents and brother wouldn’t find out. I kept her panties under my clothes in a bottom drawer and thought about how good it felt to wear them, for most of the night until bedtime. That night I fell asleep thinking about what it would be like to have little breasts, dress like a girl and wear dresses and stuff to school... and maybe play with Scott while I was dressed like that...

hat summer I was nine, we played many times in the basement, and I often wound up in Margaret’s panties. The summer ended though and Scott had not played with the girls like I did, nor was he likely to. He was too nervous about girls yet, switching back and forth between wanting to get to know Tracy and saying girls were silly or gross and he didn’t want to have anything to do with them. In the meantime, I would spend time playing with the girls, exploring girly things and having fun, while sometimes spending the night with Scott, often playing with his dick for him when he wanted. School started and the girls went back home, so I didn’t get to play much with girly things and I outgrew the few pairs of panties I had. But by the time I turned ten, the girls were back to spend the summer again with their Nana. I was already missing the feel of panties and dreamt about them often, so I was really excited to find out they were back.

For awhile then, I looked for ways to get panties from the girls whenever I could, and I would sneak or steal panties from them. I would sometimes play at their house not just in the basement, but also in the attic. When we were up there and Nana was in the kitchen, I would “go to the bathroom” but really go into their bedroom and find panties and take them, sliding them into my pocket or then going into the bathroom and changing into them. It just felt so natural, even if a little exciting, to be wearing small briefs or bikini panties in soft pretty colors with no harsh folds, tags or openings like boy’s undies. They were usually soft and silky and sometimes had cute little, scalloped edges that made me feel so girly. Some were cotton, pink with red trim and had things like Strawberry Shortcake on them. I found I liked the pink ones the best and tended to take those when they were available. I wore them as much as I could for awhile, whenever I could dress alone or change into them while no one was around.
More and more as I played with the girls, I found that I really enjoying things like dolls and Barbies because I didn’t have any of those things. My toys were all boy toys like cars and Hot Wheels and stuff, so when I went over there I liked doing what they wanted to do. Oddly enough, my mother was sending me over there more and more. She even said I always came back in such a good and calm mood when I played over there, not like when I went out to play with other boys, so she really liked having me go play over there.

One afternoon on a rainy day the girls and I were playing with dolls up in the attic and they decided to play with makeup. I told them I had to go to the bathroom and went downstairs. I went into their room and found a nice pair of pastel pink, silky, scalloped edged panties and slipped them into my pocket. I then went into the bathroom and pulled down my pants. I pulled off my Jockey shorts and put them behind a drawer in the bathroom vanity, and put on the pink panties. They were so silky-smooth and slightly tight. They rubbed my little peenie and made me hard, but I pulled my pants back on and it softened up a bit. It was still very exciting, especially when I walked and my pants rubbed my dicky through the silky panties, reminding me with each step of the girly feeling in my pants. If I listened closely, and it was real quiet, I could even hear a slight swish-swish as I walked.
I went back upstairs and the girls had a play vanity with all kinds of eyeshadow, lipstick, eyeliner, blush and powder and such. They were putting makeup on each other, giggling and having a great time in front of the little mirror. I sat down on the floor since there was only one little matching chair (as much to get comfortable as to hide my little boner), and picked up a doll.
Margaret said, “Let’s make-up Mitchie! I think he would make a very cute little girl!” My mouth just dropped open in shock and she leaned over and started putting lipstick on me. I didn’t know what to do, so I just froze like that, which happened to be perfect for her to apply it. Tracy scotched closer and started putting eyeshadow on me and then Margaret began brushing my hair. They were treating me like one of their dolls and I was actually starting to love it! Then Margaret said, “Now we have to dress him, er, her up!” I immediately thought of the pretty pink panties I already had on and began to blush. They giggled and pulled me to my feet. I protested weakly as Tracy pulled my shirt off over my head and Margaret began unbuttoning and zipping my pants.  Margaret stopped in the middle of pulling my pants down my thighs and started laughing. She backed up and pointed at me and covered her mouth, she was laughing so hard. Tracy stared at her then looked where she pointed and a big smile crept across her face. I looked down and my little peenie was hard and pushing straight out making a tight, silky-smooth, pink pup-tent in Margaret’s panties. Margaret was about my size and Tracy was a little bigger and had hips already, so I always took Margaret’s panties. Of course, Margaret recognized them and she stopped giggling and put her hands on her hips and said with false scorn, “And just where did you get those?”

I just stammered a bit and she laughed again and said, “I know, you took them from my drawer!” She moved forward and looked me up and down and said, “It’s okay, if I had known you like them so much... hey! So that’s where my missing panties have gotten off to!” She giggled some more and said, “Well, we’ll just have to make sure you have plenty of panties to wear, all the time...” and she turned around and ran downstairs.

Tracy was still giggling and I was still very pink, embarrassed and warm standing there with my pants now down to my ankles and nothing else on but a shiny pair of pink satin panties with cute little-scalloped trim and makeup. Tracy said, “I know,” and also turned around and ran downstairs.

I didn’t know what to do, I had no idea what they were up to and I was afraid that Nana might yell up to me to come down. I began to tremble a bit, but I was still frozen in place like a deer caught in the headlights.
It wasn’t long and Margaret was back with a small girly bag, a play-toy bag with something like My Little Pony on it. She held it out to me and said, “Here, these are for you, you little girly-boy! I have extras, so I want to make sure you have plenty... and I am going to check and make sure you are wearing them, too!”

I was still trembling as I took the bag and opened it. I was confused because I didn’t know if I was offended at her saying I was a “girly-boy” of if I was relieved she wasn’t upset I had stolen her panties. In fact, it was beginning to dawn on me that not only was she not mad, she was giving me panties... and she wanted me to wear them.

That’s when Tracy came back with her own goodies. She had a hand full of left over training bras and handed me one. I just looked at her and she said, “Put it on.” I had no idea how to do that and as I just stood there with the bag in one hand and the bra in the other, Margaret took the bag from me and set it down. Margaret said, “Here, let me help you,” and took the bra from me. She twisted it around and straightened it, then told me to hold my arms out. She slipped on arm through a hole, then bent my other arm into the next hole and turned me around to pull it over my head. She pulled up the straps and snapped them, startling me. She spun me around and they both giggled and Tracy said, “Now you look like a real girl!” Margaret stooped and gathered up the other bras and put them in the bag while Tracy rummaged in a zippered clothes storage hanger there in the attic. Most of them were training bras, but a couple had hooks. Tracy pulled out a small white print dress and shook is out, then held it up to check the size. It must have looked about right because she unzipped it and told me to step into it.

Trembling still, I shook off my pants from my ankles and stepped into it one foot at a time. They both pulled the dress up and adjusted it, and Margaret zipped it up. It was a little tight and hung to just above my knees, but it fit really well. I was so excited, pumped with adrenaline and conflicting thoughts, that I nearly fainted.

The world around me became crystal clear in that moment... I heard the rain pitter-pat on the roof above our heads, I felt the tightness of my chest against the new feeling of a bra and dress, and I felt my tiny hard-on twinge in my slick pink panties. Feeling dressed but open from below, was new too. I felt vulnerable yet not quite exposed, with a slight breeze brushing against my thighs and panties I was hyper-aware of being exposed from below. I could smell the powder, lipstick and other scents of makeup on my face and hear the excited breaths of the girls as they admired their handiwork, twirling me slowly around and looking me up and down. At that moment, I felt the pleasure of having people look at me as a pretty thing, a soft and feminine girl. And I felt the thrill of a hidden secret under my dress; the one thing that made me not really a girl, no matter how pretty I was in the little mirror of that toy vanity.

We played “house” for what seemed like hours after that, three girls raising dollies and talking about their “husbands” away for work. Finally, the day wore on and it was time to clean up. I took off the dress but Margaret said I had to keep on the bra. I was already committed to wearing my panties home, besides, I really wanted to keep them. The bra was not really visible under my dark t-shirt, and I was already so used to it I didn’t really think much about it. Margaret took me into the bathroom down stairs and helped me wash off the makeup, then handed me the bag full of bras and panties. She said, “Wear these, ‘cause I am going to check on you,” and went downstairs with me to see me out.

I had to be careful when I got back home, I now had several pairs of panties and bras and I didn’t want my parents to find them. I found a new hidey-hole in the basement of our house, which had a black painted window in the back corner of the “pool room,” a room my parents had remodeled into a game room with a pool table. That window was supposed to be access to the pump for the side yard fountain. There was a short tunnel behind it that led under the side yard patio and the pump was at the end of the tunnel. But there was also a small hidden room off to the right, under the kitchen, through a hole in the wall of that tunnel. That is where I started keeping all of my girly things...

The summer was ending and the girls went back to live with their mom and dad. I was still a pre-pubescent boy, not quite mature enough to cum, but I was quickly becoming obsessed with wearing girly things and playing with boys when I could. Next summer the girls would be back to stay with their Nana. Scott and I played around some, but not as much and I didn’t let him know about my panties. Chris was pretty much out of the picture and off with his own friends. However, that Fall I went away to boarding school for the first time, and everything changed...

Next: Going Away to School...