This is the story of how I became a sissy. I was always a tiny boy growing up. One of the shortest in my grade, and no muscle whatsoever. Unfortunately, I was lacking in other areas as well… I would watch porn and be amazed at the massive cocks that would fuck these beautiful women and I just knew I’d never be able to do that. One day I discovered sissy porn. In the videos, the girls would talk about small dick losers and how they belonged in panties. This turned me on so much and I would watch those videos every day. Eventually the videos made me want to try on panties myself. I snuck into my sisters room one night and grabbed a pair. I tried to grab the most normal looking ones I could. I didn’t want anything too girly. I grabbed a blue pair that didn’t have much lace or anything too crazy. I ran back to my room excited to try them on. As I slid them up my legs I felt tingles through my body. As soon as the soft fabric touched my cock I immediately got rock hard. I instinctively tucked away my little dick in the panties and it was a perfect fit. It felt so natural to be in panties, like I was made to wear them. I couldn’t help but pose in front of the mirror and check out my ass, and it actually looked quite cute in panties! I got so excited and started humping my hand furiously. I never came so quick before in my life. After that, I knew I needed more. I went to the mall that weekend and went right to the Victoria’s Secret. I picked out about 5 pairs of panties, all different kinds. A lot girlier than the pair I wore before. I did my best to hide the fact that they were for me, and hoped the girl helping me didn’t know. I could feel myself getting hard as I was checking out, and as soon as I was done, I ran out of the store and back to my car, hiding my boner with my new bag of panties. Right when I got home I went up to my room and tried on every pair. I LOVED all my new panties and would go on wearing them every day in secret. I was having so much fun, but it was only a matter of time before I needed more… I wanted to be a real sissy, and to do that I needed a real man. I downloaded Grindr and uploaded a cute pic of just my butt, hiding my face. Right away I got TONS of messages from guys, some respectful, some just sent me their cocks right away. I had never felt so desired before in my life, certainly not with any of the girls I liked. I loved the attention, and so I flirted back with all the guys messaging me. There was one that stood out though. He seemed so nice and gentle. He was so understanding of me. We talked for a few weeks online before exchanging naughty pictures. I eventually sent him a pic of my little dick and he just laughed. He sent me a pic back and my jaw dropped. He had a MASSIVE BBC. It was just like the porn stars I used to jack off to. I never considered myself gay, but that cock made my brain melt. After a lot of convincing, I finally agreed to meet in person. He wanted to have sex, but I was too nervous as I was a virgin. He was nice though and said we didn’t have to do it if I was uncomfortable. We agreed that I would just use my hand a bit and that’s all. I went over to his place and we hung out for a bit before getting things started. We went into his room and laid down on his bed. I asked him “well do you wanna take your pants off?” And he replied by saying “take them off for me”. That turned me on so much. He was stern in his voice and it really felt like a command. So I followed orders and began unbuckling his belt. I was so nervous my hands were shaking, but all of that disappeared as I pulled down his pants, and then his boxers, revealing his giant manhood. I had seen pictures before, but it still blew my mind how big it was. It was thicker than I thought from the pictures and I could barely wrap my small hands around it. I slowly started stroking his cock and I felt him grow harder in my hands. It was such an incredible feeling. Without saying anything he climbed on top of me as I was lying on my back, his cock staring me right in the face. I grabbed it with both hands and continued stroking it a bit faster now. He pulled my pants off me revealing my pink lacy panties that I had on. He began rubbing my cock through my panties like it was a clit. I was already so hard. He laughed a bit and said “you really do have a cute little clitty” and almost immediately I came in my panties. Again he laughed, and then he grabbed my hips and flipped me over. He was now sitting on top of me, with my pantied ass exposed to him. He started rubbing his cock against my ass, and between my cheeks. He said “don’t worry baby, I’m not gonna fuck you tonight”. He was being so nice to me since he knew it was my first time, but a part of me thinks I would have let him fuck me then and there anyways. He started rubbing his thumb against my hole over my panties and I jumped a little every time he pressed a little too hard. He pulled my panties to the side and began rubbing my hole again with his thumb. He asked me if he could stick it in and I was so turned on I happily agreed. He slowly worked his thumb into my ass as I squealed with pain and pleasure. I could tell that it turned him on a lot because he began stroking his cock faster and faster as he fucked my ass with his thumb. I’ll never forget when he said “are you ready for daddies cum baby?” And I yelled out “yes daddy! Give me your cum!” Like a needy little slut. He came all over my ass cheek and made sure to get out every drop. He then slapped his massive cock against my ass a few times before getting up. I laid there, not moving, with my panties filled with my cum, and my ass covered in his. I knew that this was just the beginning of my sissy adventure.