Date: Sat, 21 Dec 2019 00:04:15 +0000 From: annah4phallactik Subject: Discovering A Young Sissy-chapter one Discovering A Young Sissy by Annah Phallactik Chapter one Please consider making a donation to nifty to keep this going. This provides a great resource for writers and readers alike. When I was 25 I got a part time gig from a buddy of mine named Tommy cleaning up and prepping his rentals for new tenants. He had a couple dozen houses and an apartment complex as well. I was a young man, living in Florida, the flexibility was great, and at the houses I could play my stereo and have a few beers while I was working on them but I had to tone it down a few notches in the apartment complex. I was cleaning up one of his rental homes in a neighborhood that was lower middle class. A woman and her two teenage kids had rented the house previously. Apparently the dad split and she couldn't afford the rent, so Tommy helped her out and put her in a cheaper house. He said she was working 2 jobs now, so he trusted she would be able to handle it. She left this place a mess, but he let her make a few payments for the cleanup. As I was going through the 3 bedroom place, it was obviously the mom and a young teenage boy, and a teenage girl. The moms' room wasn't too bad, but the teenagers rooms were pretty messy, with lots left behind. I started with the moms room first, and had it all picked up and vacuumed in a couple hours. I decided on the girls room next. It was littered with some garbage, discarded makeup, a torn poster, and a couple piles of clothes. I started with the garbage, and made quick work of that, maybe this room wasn't so bad after all. I grabbed another big black garbage bag for the clothes, I figured there was about that much there. I wanted a chance to go through the clothes anyway. I had started cross dressing as a teenager, discovered I was bisexual at 19, and I have always had a fondness for teen girls and boys both. As I was putting the clothes in the bag, I saw few cute tank tops, some shorts, a couple pairs of leggings, a few bras, and a good handful of panties. At the bottom of the last pile there was a cute little bikini, and a sexy little 1 piece swimsuit. I was pretty excited to find all this and I couldn't wait to get this home, wash it and try it all on, this promised to be a few nights of some great jack off sessions and maybe something cute to wear for a special someone I had yet to meet. This was going to be a great gig if I kept finding stuff like this. When I was done with the girls room, I took my stash of clothes and headed to the boy's room. When I started on the boy's room, I realized it wouldn't be too bad, really just a bunch of loose garbage. I started with the walls, tacks and various torn pieces of posters was all there was. I hit the closet next, raking out some trash, and a few old hangers in there, when I noticed the baseboard was loose, and had been pulled out. I gave it a little wiggle and it popped open a little cubby hole. Inside there was a pile of ripped up porno mags, I pulled some out, the usual fucky sucky porn, there were pages pulled out and in a stack. These must have been his favorites. I went through them, mostly photo spreads of skinny chicks taking it in the ass. This must be something he liked. I reached in and grabbed the rest to look at and there was something soft in there. When I pulled it out, there was a pink cotton crop bra, and some matching pink cotton panties. When I set the panties down I noticed the front was pretty crusty, the boy must have snagged his sister's clothes and dressed up and masturbated in them! I was getting ready to scoop up the girls underwear and porn mags and put them in my bag of clothes when I heard someone yell hello from the front door. Before I had time to yell back or do something with the stash I just found, a kid about 13 or 14 appeared in the bedroom doorway. From the angle of the doorway to the closet I don't think he could see the cubby opened, but I think he probably knew. He looked away quickly, and said he was checking to see if his mom got everything. He started for the living room, and I yelled that everything was bagged up and still all in the house, and to Look through it if he wanted. I went to the living room and pointed to the bags. He seemed a little flushed and distracted, so I knew he was worried about his stash. I decided to test him, I went back to the bedroom and grabbed the pink cotton bra and panties and headed to the living room. I had them dangling from my fingertips and asked if this is what he came back for. The look on his face told me all I needed to know. His cheeks got a little red, and he started stammering that he didn't know what I was talking about. "It's ok" I said, "it's really pretty normal". He looked up at me, with a quizzical look on his face. "I wear stuff like this too sometimes, really it's ok". He was really looking at me now, not sure where to go with this. I was pretty horny now thinking about this kid in his sister's underwear, and maybe me in his sister's underwear. "So this is what you came back looking for?" I said, still dangling the clothes from my fingertips. He just looked at them, a lump in his throat. His young hormones had just taken control of his brain. I could see a look of lust in his eyes, and he was visibly hard, and pretty good sized too it looked like. I told him to hold on a second, and I went back to the bag and pulled out a pair of silky white panties and a cute pink and yellow T-shirt bra his sister left behind. I went back to the living room and locked the door as I passed and tossed the pink set to him. He caught them and was staring at the set I had in my hand. He was quite visibly hard now, he looked like he was hiding about 7" in there. "If you want I'll dress up with you if your interested, believe me it's more fun with two" He just nodded his head, the lump still in his throat, but the look of lust still in his eyes. "Do you want me to change first" I asked him? He just nodded his head. I told him to go into the bathroom and change, and I would change in the living room. He was putty at this point. He walked towards the bathroom, slipped in and shut the door. I wasn't sure if he was going to go through with it, but I was too horny at this point to slow down. I undressed in record time, pulled the panties up and into place. They were small silky brief cut, they didn't do real well covering my straining erection, but fit nice every where else. I slipped my arms through the bra straps and pulled it into place, adjusted the straps a little, and clasped the little front clasp up. Looking down at myself, I thought I looked pretty hot. I couldn't wait to see him walk out on the cute pink set on his nice little body. I really wanted to see his cock, it looked pretty big for his age. I asked him if he was doing alright, he hollered "yeah" through the door. I heard the door open and he peeked out, probably wanting to make sure I held up my end and changed too. He saw that I was standing there in a bra and panties and slowly emerged from behind the door. He walked out to the living room. Man he looked so hot, the underwear set fit him perfectly. He was completely smooth and tone, and the bra looked perfect on him. The panties were straining to keep his rather nice cock in place. "Have you ever done anything like this with anyone before?" "No" while shaking his head I walked over to him, put my hands on his hips and asked "are you nervous?" He nodded his head, blushing just a little. My hands rubbed up and down feeling the sides of his panties, working my fingertips back a little to feel his cute panty covered ass. I pulled him to me, allowing our panty covered cocks to touch. I pushed my hips forward, slowly grinding against him. As I ground our cocks together I started kissing his shoulders and neck. I was going slow, making sure he was comfortable. I have always considered myself to be versatile, so I was pretty torn up about where I wanted this to go. His ass looked absolutely scrumptious in those pink cotton panties, but he had a nice looking cock I would love to ride too. I continued kissing his neck, moving up to his cheek, my hands still cupping his sexy little behind. As I was kissing his cheek, I whispered in his ear "is this ok?" He nodded his head, and the hardness of his cock pressed against mine reaffirmed that. I slowly kissed my way towards his mouth, leaving a trail of soft pecks on his cheek and lips. Those pecks turned to kisses, my tongue stroking his lips, coaxing his mouth open. That first open kiss must have done it for him because he wrapped his arms around tight and pressed against me hard, his hips making small thrusts, gently but firmly humping these two panty covered dicks together. We stood there making out for about 5 minutes when i broke the kiss. I spread an old blanket out on the floor and had him lay down with me. Down on the blanket he was laid out straight, legs together, so i climbed on him straddling his legs, and started grinding down on him from the tip of my cock all the way to my ass crack, and resumed our making out. He was really picking up on the kissing, both of our tongues were intertwined in each others mouths, but his arms were still down by his sides. I reached down, lifting one of his arms so his hand was on my ass. His other hand followed immediately, and he was soon squeezing both of my panty covered cheeks and pushing his hips up to meet my thrusts. I knew right then i had to have his boy cock inside me. The grinding had caused his panties to slide down in front, exposing his cock, I licked my hand and reached down to stroke it. I started kissing his neck and chest while he slowly pumped his cock in my hand. He was now moaning, making me even more excited, I wanted him in me before he was ready to cum. I let go of his cock long enough to reach back and pull my panties aside. I gathered up some spit in my hand and got my hole as wet as i could, i hadn't planned on this, so spit was going to have to do. I got my hand as wet as could and started stroking his cock again, mixing my saliva with his precum. It was at this point that I think he realized what was about to happen and it occured to me he was probably a virgin. This got me even more excited knowing I was giving him his first fuck. With my hand holding his cock up I leaned down and kissed him, my tongue was running over his lips until he opened his mouth and his tongue met mine. His cock was now nestled against my opening and I relaxed and let myself slowly sink down on it. When I hit bottom he let out a gasp and I broke the kiss. "Does it feel good" I whispered to him. With his eyes glazed over in lust, he just nodded his head. "You just relax and let me take care of you". I went back to devouring his mouth while slowly rocking up and down on his cock. After about 2 minutes his arms went around me, pulling me tight against him, letting out a small gasp as I felt him throbbing inside me, letting his cock spurt deep inside me. I milked his cock for another minute while he came down from his orgasm, kissing him whle his arms were still wrapped tight around me. When his arms loosened up, I sat up a bit and looked at him and said "so did you like"? "Oh my god, that was great, was I ok"? "You were amazing, and you're still very hard" I said with a big smile. "I can't believe how good that felt, that was so much better than my hand". "I'd really like to make you feel good again', with that I started rocking up and down. I'm sure he didn't produce a lot of cum, but it was definately slicker now. I worked my ass up and down his cock, feeling it grow even firmer, oh to be 13 again and stay hard perpetually. He was getting into it more this time, thrusting back into me. I stopped an spread my legs out and squatted over him and told him to go for it. His hips immediately started rocking up as he gently fucked me, I wanted him to move himself, fuck the way it felt best, I wanted him to enjoy it and give me another load. I reached into my panties and pulled my cock out the side of them and started stroking it. He must have enjoyed the sight as his thrusts got more deliberate and deep. When he grabbed my hips and started fucking harder, I picked up my pace on my own cock, I was very close. When I started moaning, and felt myself on the edge of orgasm he made one final thrust and pushed as far as he could in me and started filling me with his boy seed again I aimed my cock down towards his chest and fired a huge wad of cum out. My aim was off as it ended up hitting his chin and cheek, followed by 4 more shots that hit his bra and chest. When the last bit finally drizzled outi collapsed on him running my tongue over his face, collecting my cum and sharing it with him in a kiss. He was obviously ok with it, he kissed me back hard and seemed to be savoring my cum in his mouth. We we made out and felt each other up for about 10 minutes when his cock finally softened up some and slid out of my ass. "How was that?" I asked him "It was amazing, I never dreamed it would feel that good". "Well, you are a natural, and very sexy dressed up like this". "Thanks, I always thought I was weird and the only one that did this". "Not at all, I've messed around like this a few times, but this is by far the best, you were great". I got up and started getting dressed, pulling my clothes on over the bra and panties. "I think I'm going to keep these on so I can savor the fun we had" He pulled his clothes on over his bra and panties as well. When we were both dressed I walked to him and put my arms around him and pulled him close. I felt the bra lines through the back of his shirt and then started squeezing his ass, feeling his panty lines too through his jeans. I kissed my way up to his neck and whispered in his ear, "would you be interested in getting together again?" His arms went around my neck and he melted into me, nodding his head and he whispered "yes", then nuzzled his cheek against my chest...... more to cum, another encounter with this cute little panty boy awaits. I love all feedback and comments... annah4phallactik@gmail.com