I’m laying in his bed, fully dressed up like a slut, my little clitty locked up, and he says “today is the day you get fucked like a girl and cum like a girl, bitch!” I’ve never been more scared before. I’ve never been fucked before, not even by anything bigger than the smallish butt plug that was in my ass. And now I have a massive BBC slapping against my pantied ass. After covering my ass and his cock in lube, he begins rubbing the tip of his head up and down against my hole. He says “pull your ass open for me bitch!” In a demanding tone. I immediately reach back and spread my ass cheeks for him, opening up my hole to him. He takes the opportunity to slowly press his head inside of my boy pussy. I gasp out in pain from his massive, thick tip entering my ass. I grimace as just his tip stretches me like never before. He stops after getting the tip all the way in and says”good girl! The worst part is over. You’re doing so great baby.” His tone completely changed, and he was being gentle and caring. He leaned down close to my face, pressing his body against mine, and kissed me on the cheek. He said “hold your ass open for me, I’m turning you into a real girl now.” I did as he said and he slowly but consistently slid his giant cock into my ass until his whole cock was inside of me. I had never felt this much pressure in my ass before. It was so intense, it filled my whole body. I felt my balls tense up as they haven’t been able to cum in a week. I felt the most intense orgasm build up through my entire body with every inch of his cock sliding into my ass. He completely filled me up and after about 3 seconds of him holding his BBC in my ass, I felt so much cum explode out of my little locked up clitty. My first ever sissygasm. I tried achieving that for hours with my butt plug, but I was never able to. After about 3 seconds of a real mans cock penetrating me, I was covered in cum. I had never felt like such a cock hungry slut in my life. I was desperate for his cock, I needed it inside me. His cock awakened the sissy slut I always needed to be. He watched me scream out in pleasure as I filled my panties with cum, and said “I knew you were a sissy slut.” He slowly pulls his cock back out and then jams it back in hard. He said “just because you got to cum, doesn’t mean we are done bitch.” I cried out in pain from having his massive manhood rammed up my ass. I said “yes daddy, please fuck me, I need your cock.” He began fucking me slowly, and then started picking up the pace, getting more aggressive with me as he fucked me harder. He was slapping my ass so hard it would sting more with each slap. He had grabbed my arms behind my back and was holding me down as he stretched my boy pussy open. My legs went up in the air and my toes curled with each slap to my ass. He went on doing this for almost an hour, flipping me into all sorts of positions, and fucking me relentlessly. I sissygasmed probably 3 more times from his cock. After what seemed like an eternity of having my ass drilled, he was finally going to cum. He had me standing up, he was behind me holding me up. My feet were almost getting lifted off the ground, only my toes were touching. He grabbed my balls through my cum soaked panties and said “now it’s my turn to cum, bitch!” He thrust his cock into my ass so hard, it lifted me off the ground. I felt his dick tense up inside of me, and an explosion of his hot, sticky cum flooded deep into my ass. He yelled out in pleasure as he pumped my ass again and again, full of his cum. He lowered me back onto the ground, and my knees were so weak I collapsed to the floor. My ass sticking out in the air, holding his cum. He laughed and said “I’m guessing you liked your first time being fucked like a slut?” I was so exhausted I couldn’t even respond. I was totally worn out, and my ass was gaped open from his cock. My clitty was exhausted from blowing load after load through my chastity cage, and into my panties. My legs had basically gone numb. I laid there totally humiliated and degraded. I was in total sissy heaven…