Date: Tue, 20 Aug 2019 01:50:14 +0000 From: annah4phallactik Subject: Panty Playmates This story is pure fiction. Please consider donating to Nifty to keep this site going. I appreciate all comments and feedback, annah4phallactik@protonmail.com My name is Andy, this explains how and when I became a sissy. I was 13 years old, and lived in a nice neighborhood right outside Atlanta. My best friend Steve is also 13 and lives 4 houses down from me. We have been best friends for about 5 years, both of us have single moms, which means we had a fair amount of time to hangout after school without a lot of adult supervision. We also each have a younger sister, they are both 12 and also best friends. With Steve's mom and my mom working, and our younger sisters being best friends, us boys were usually at one house or the other, and the girls usually opposite from where we were. Steve and I are both a little small for our age, and are both a little nerdy, being into computers and video games mostly, while our sisters were both tall and both into sports, they played basketball and volleyball. My sister, Amanda, was my height and his sister Rochelle was an inch taller then he was . His driveway was flat, so they had a basketball hoop up and an above ground swimming pool in back. My mom is kind of a computer geek so we had 100 meg wifi at my house, so mostly Steve and I were at my place and the girls at his place after school. I started beating off around 11, mostly thinking about the girls my geeky self would never get, occasionally finding some porn on the net to assist my fantasies. My first few times were just dry cums, but the first time I squirted was amazing and I was hooked, jerking off every night. This was one thing I didn't share with Steve. As my masturbation fantasies always progressed towards all the cute girls I wasn't ever going to get, my sister and her group of cute athletic friends gave me plenty to think about. One Friday evening a few of her friends were staying over, after riding bikes and playing outside, the girls headed to the basement to hang out to watch movies. Amanda had Rochelle and Tammy staying over. Tammy was real cute, about the same lean athletic build as my sister, but she had started sprouting some boobs already. My sister and most of her friends all had some small bumps growing, but Tammy had some actual boobs. While they were watching a movie, I was in my room getting ready for a serious jerk-off session, I went to use the bathroom. After I peed I noticed a back-pack on the floor. The back-pack didn't look familiar so I assumed it was Tammy's. I couldn't resist, I had to peek inside. I rummaged around, it was all clothes, lots, like she was planning on staying for a week. I felt some soft and silky stuff at the bottom, so I very carefully pulled the shirts and shorts off the top and there in the bottom of the bag was a pile of her underwear! Some panties, a bra, and a swimsuit. I grabbed the panties on top, a paisley silky bikini panty, but my finger must have snagged her swimsuit, and that came out too. I wadded them both up, gently stacked the clothes back in and zipped the bag back up. I tucked my find up under my arm in my robe and ran into my room, locking the door behind me. I sat on the edge of my bed and pulled my goodies out, I was instantly hard just touching these delicate pieces that were once wrapped on Tammy's body. I held the panties up and just rubbed the soft fabric, all I could do was imagine her wearing these. I couldn't wait any longer, I l back and immediately started stroking myself, just holding the panties. I was so turned on I knew this was gonna be a quick one. While stroking my little 13 year old dick with one hand, and feeling the panties with my other hand, I switched hands, the feel of her silky panties on my dick shot me over the edge, I just started spurting all over the panties. As my cum slowed down I started to panic a little, I just coated her panties with cum, I couldn't just put them back now! I panicked a little, I wasn't sure if she would even notice them missing, after all it looked like ft she had a weeks worth of clothes in her bag. Besides, I wanted to keep these, they were so soft and silky, pink and purple paisley, fabric all bunched on the string and hem all around, yup I was going to keep them. I sat up on the bed and looked down, seeing the swimsuit that fell, I picked it up, a one piece, string straps that crossed over the shoulders, a pale pink and pale blue, and the same silky feel that her panties had. I was hard again just from holding this treasure. I started rubbing the material on my dick, it was amazing, so soft, silky, I quickly hopped up to make sure my door was locked, and stood in front of the mirror rubbing myself. As I lifted the swimsuit up to take in the aroma that only girls clothes seem to have, they unrolled, leaving the top part at my nose, and the rest hanging in front of me. I saw it hanging in front of me, pulled it tight to my body, seeing how it fit against me. It took all of 2 seconds to know it belonged on my body and I was stripping out of my clothes and sliding this amazing bathing suit up my legs. The silky feel of the snug lycra encasing my small body was almost too much for me, I was rock hard and right on the edge. I pulled it up, straps over my shoulders and made some final adjustments. The feeling was incredible, my hard dick was pulled flat against me, with a little dark spot already showing from precum. I was in heaven, I knew right then I would always want to be in girls clothes. I laid back on the bed softly rubbing my hands over the soft tight material on my body. I ran my fingertips up and down my front, pausing over my dick, then slowly pushed both hands together over it, encasing my dick in between them, under the tight material. I slowly stared pumping up and down, the feeling was pure ecstasy. I rubbed myself about 1 minute like that and just started blasting uncontrollably, my body spasmed, it was by far the best orgasm I have ever had. After that day I would find time every day to beat off in my new panties or swimsuit. I even snuck into my sister's clothes once and borrowed a white cotton matching bra and panty set. I knew she would miss them so I had to be careful not to get cum on them. One day Steve and I were playing over at his house while our sisters were at a basketball game at school, we were shooting hoops in his driveway when he took a dive and landed in some mud. He said he was gonna go shower and change, so I went inside to wait for him. Steve headed to the bathroom and I was going to hang out in his room. As I walked down the hall, I passed his sister's room, and my curiosity got the best of me. I listened to make sure the shower was on and went in her room and straight for the dresser. I opened the top drawer to a sea of delightful little underthings. It was crammed full to the top! I started sifting through carefully, pulling out one thing at a time, marvelling at all her pretty panties and bras. Most of them were cute cotton items, in every pastel color there was, but one thing caught my eye towards the back. I pulled out a purple silky pair of hipster panties, and under them was a matching training bra. I knew I had to absolutely have these, I quickly stuck them down in my pants, careful to keep them against me and not cause an obvious bulge, and headed towards Steve's room. When I got to Steve's room, he was just finished getting dressed. He said he was hungry and headed to the kitchen to get something to eat. I took this as my chance to run home. I told Steve I was running back to the house for a few. He asked why, and I told him I needed to check on something for my mom, and grab a quick snack, and that I would be back. He looked at me funny, and I knew it was unusual for us to snack separately, but there was no way I could shoot any more hoops, or anything for that matter, with a semi hard dick, and his sister's panties stuffed down my pants. I ran back home quickly, mom was at work, probably for another 3 hours, and I knew my sister and her friend would be another couple hours, so I darted up stairs to rub out a quick cum with my new panties and bra. As I passed my sister's room, I stopped, the girly scent of her room, the pile of clean clothes on her bed, and her dirty clothes all over the floor, this had me even hornier. I darted in there, stripping as I went in. I pulled out the bra and panties, as I slipped my boy underwear off. I slowly pulled on the purple panties, they were snug, but fit perfect. My dick was hard as a rock, pressing tight against the silky material. Next I pulled the bra over my shoulders, pulled it into place and reached around and clasped it together on my first try, I was a natural, I should have been a girl I thought. I looked at myself in my sister's mirror, if my hair was a little longer, and some makeup, I thought I could look like a girl. I was extremely horny at this point, I could see a small spot appear where my dick was leaking a little. I pushed some of her dirty clothes into one area and laid down in the middle of them. With one hand I reached down between my legs and grabbed whatever was there, which happened to be one of her swimsuits, and my other hand grabbed what ever was next to me, which was a pair of her tight workout shorts. I brought the shorts up to my face, they smelled like my sister, a light perfumy smell and some musky smell I knew was from her. As I inhaled the aroma from my sister's shorts I started rubbing myself with her swimsuit over my panties. The sensation from the slick materials rubbing together was amazing and I started spurting cum into the panties almost immediately. I arched my back up, humping my hand and the wadded up swimsuit. It felt like I came a gallon, I think it was the best orgasm I had ever had. As I came down from my euphoria, my head rolled back and there was Steve standing in my sister's doorway! I panicked and started to scramble up, but I was busted, no hiding or explaining this one. Steve just looked at me funny, I didn't know what to say, hoping he would say something first. Then he smiled. "You too?" he said Now I was totally confused. "What?" I stammered out "You too?" He said again, "I figured I had time to jack off real quick while you were gone, and I usually put these panties on when I do" I was still at a complete loss for words, trying to comprehend what he was saying. "I went to my sister's room after you left, and they were gone from her drawer, I knew she would never wear these playing basketball, and I guessed that's why you left so quickly". I was still sprawled out on the floor in a pile of my sister's clothes, in his sister's underwear, and I looked at him and said "you do this too?" I was still confused, but feeling a little better about it all. Steve had come and sat down on my sister's bed. He told me he started jerking off on Rochelle's panties when he found them in the hamper in the bathroom, and Amanda's too when she stayed the night. He told me it didn't take long before he found out it was better when he put them on. As he was telling me how he went from just her panties to bras, swimwear and anything else he could find, I found myself getting hard again. It looked like the front of his shorts were tenting up a bit too. He looked down at me and said "the girls will be another hour at least, can I put on something of your sisters and we can get off together?" I said "sure!" Steve scooped up the wadded up swimsuit I was just rubbing myself with. He quickly shed his clothes allowing me a glimpse of his cock. It was a little longer than mine, and a little thinner. As he was sliding the swimsuit on I sat up and waited for him to join me. When he had it pulled into place, I let out a small gasp. Steve was absolutely breathtaking. The bathing suit fit perfect on him. It hugged his body in all the right places, covering his very hard cock nicely. The bust area had a nice light padding, giving the illusion of small breasts. He turned around so I could see the rest of it. The swimsuit had an open back and the bottom hugged his ass perfectly. He could easily pass as a teenage girl if he had long hair. It was just a simple black one piece swimsuit, but it was the sexiest thing i had ever seen. Steve got down on the floor with me, legs crossed in front of me, his boner bulging out of his swimsuit. I was already hard again and ready for another cum. We were now facing each other and I grabbed my dick, through the panties, jacking it up and down with the material, watching Steve start to do the same. Afyer about a minute of that he stopped, pulled my legs apart and spread his open and scooted in so our dicks were almost touching. "Let's rub them together, is that ok?" He said Before I could say anything he pushed his dick right into mine. The feeling was too incredible to object, not that i would have. We started rocking back and forth, the tight slick material making it slick feeling. Steve reached his hands out and cupped my ass, pulling us close together. I wrapped my arms around him and rested my head on his shoulder while we humped our dicks together. Steve had laid his head on my shoulder too and surprised me by kissing my neck. Thats all it took. I ground in hard, moaning and spilling another load into my panties. As i was cumming he started making little squeak noises and his dick pressed hard against me and he started shooting his cum into the swimsuit. After a minute, our breathing slowed down and both sat back. I just sat and smiled at him, "oh my gawd, I thought it was awesome by myself, that was way better!" " I know, that felt so good, you looked soooo cute and that rubbing felt amazing. You should stay the night tonight so we can do it again". "is my sister staying with Rochelle tonight or will they be at my house?" "I think they will be at your house" Andy said as he stood up. " we better change before anyone gets back though" "Your right" I stood up and took off the bra and panties. "I will ask my mom, and bring something to wear too" Andy smiles and said "ok". Chapter 2 coming soon!