"Hey, Leah!" I opened the door to see my new friend waiting, with her black backpack, ready for another round of fun. I looked over my shoulder to look at where Tim was sitting on the couch. It didn't seem like he was very excited. Well, that only made it more fun for Leah and me! For the past few days, Tim's schedule was to wake up, go to school, then come back to the dorm room where Leah and I could do whatever the hell we wanted to him. Then, we left him in his room to do whatever he had to do. "Hey, Aaron! Hey, Tim!" Leah stepped into the room and walked over to where Tim was sitting. "How's our little sissy slut doing?" She mocked him cruelly. "Fuck you, bitch," Tim spat back. I still let Tim speak his mind. That was the only freedom I allowed him. However, his body was ours to control. I was really glad that I was able to get that chastity cage on him. "Hmm, that's not really the right way to address me, sissy. Besides, if anyone's a bitch here, it's you," Leah's steely voice really shut him up. I closed the door to our apartment and watched Leah get undressed. She was sexy as hell. I just couldn't take my eyes off her beautiful face and curvy body. I could tell that Tim was getting turned on by looking at her as well. Not that he could do anything about it. I commanded Tim to take his clothes off as well, which he did reluctantly. But within a minute, Tim was standing naked, displaying his small member trapped inside the metal chastity cage. Behind him, Leah stood, with a big, black, strap-on. This was a real sight to behold. Leah bent Tim over and stroked the large dildo. Tim resisted a little, but Leah grabbed hold of his hips and pulled him back. She lined the dildo up with his small hole and thrust it in, hard. This resulted in a satisfying sound of smacking flesh and a moan from Tim. He still wasn't used to it, even though he'd been subjected to Leah's wrath multiple times already. I took the opportunity to stand in front of my roommate and hold my stiff member out in front of his face. It took a few moments, but eventually, my cock was enveloped by his warm mouth. Once Leah saw that Tim was airtight, she slowly pulled her hips away from his ass, then slammed back in. As she did this, I started to use my roommate's mouth also. I matched Leah's thrusts, so that we both slammed deep into Tim at the same time. This was a hot sight to see. Leah's big strap-on rapidly thrusting in and out of my roommate's asshole. Every time I thrust into Tim's mouth, I felt the back of his throat contracting around the tip of my cock as he gagged. Leah reached over and started squeezing Tim's nipples while continuing to fuck him hard. Feeling Tim's moans around my cock, I could feel my orgasm coming. While Leah was pounding into Tim's asshole like an animal, I grabbed him by the throat and face-fucked him. I couldn't hold it anymore, and I held my cock deep in my sissy's throat. The clenching of his throat as he gagged pushed me over the edge. My cock twitched inside his mouth and I shot out long, thick strands of cum into his throat. Even though I'd already done this to Tim a few times already, it felt just like the first time. My member twitched one more time as I drained the last of my cum into his mouth. My cock started softening and I reluctantly pulled it out of Tim's warm mouth. I walked back, admiring my work. Tim's face was red and my cum covered the edges of his mouth. He was gagging and coughing, but I didn't care. He fell to his knees after Leah pulled the strap-on out of his ass. There was a small puddle of pre-cum forming on the floor, which had come from Tim's little cock, trapped in the chastity cage. The poor kid hadn't cum in over a week. Everyday, we've been pushing him to brink without giving him any satisfaction. Every time we finished with him, he was a mess, degraded down to a miserable sissy begging to be able to cum. Maybe today would be the day that I let him do just that. "Hey kid, you've been a pretty good sissy," I started, "I think I might let you get some release now." Leah, who had already removed the strap-on and was starting to put her clothes back on, looked at me, confused. Tim looked up at me through glazed-over eyes. His face was still red, and he really did look like a worthless whore. But he still didn't talk like one. "F-finally, you asshole. J-just get this f-fucking thing off me!" He screamed at me while pointing at the cage around his cock. "Hmm, that won't do, sissy," I mocked him, "I want to hear you beg for it." "Fuck you! T-take it off a-already!" "Alright then, I guess you don't want to cum," I shrugged my shoulders and started to put my clothes back on. "W-wait, Aaron! Just let me, please!" I turned around and crossed my arms over my chest. "Let you what?" "P-please, let me cum..." He begged. "Please, let me cum!" He said it a bit louder the second time. He repeated it a few more times before I uncrossed my arms. "Well, I'm not planning to take the cage off of you," I whispered evilly. "But you said! You said you would let me cum! I begged you! Ju-" I cut him off. "That doesn't mean you won't be able to cum, though." Tim was quiet for a moment, then his face twisted in humiliation. I guess he realized what I meant. "Well, kid, you can't really get off with that cage on unless you have some... other stimulation," I suggested. "Then take the cage off! I'm not gonna let you do... that again!" "Do what? Fuck you in the ass?" I asked him, teasingly. "Ok then, I'll be nice. I won't do it unless you ask me to." His face turned bright red. He stammered a little bit, but just ended up refusing once again. I faked a frown. "I'm disappointed. You can have it your way, then." I turned around and started to walk over to Leah, who had taken a seat on the other side of the living room, watching the scene go down. I was walking Leah out the door when Tim called me. "W-wait! Why can't she just do it? She's been doing it this whole time, I only need her to do it a little bit longer." Tim pointed at Leah. Leah turned around to look at him. "Well, I'm pretty tired out, but maybe another time." She smirked at Tim, then walked out the door. When she was in the hallway and out of Tim's line of sight, she turned to me and winked. "Have fun!" She mouthed. I smiled and closed the door. "You heard the girl. She's tired, but I'm not." Tim looked at the ground, ashamed. He was debating it. His little cock was still twitching in the cage, aching for relief. "Besides, I haven't even fucked you in the ass since that first day," I walked up close to him and whispered in his ear. "Don't you want to feel the real thing? Don't you want to feel my warm cock filling up your asshole?" "N-no... I don't want it..." I ignored him, "You just have to beg for me to fuck you deep in your tight little hole and let you cum." I know he wanted to say no, but now he was too horny. Especially after over a week of denial, he couldn't control what his body desired. His lips quivered, "Uh... ok, j-just do i-it..." I could barely hear him, but I knew he'd definitely made up his mind. Even so, I just wanted to hear him say it. I wanted him to accept it. "Do what, hmm? Tell me what you want me to do," I whispered. "I-I want you to... f-fuck me in my a-ass... please..." he whimpered. I stood up. "No, I won't," I harshly told him. "N-no! P-please!" He started to raise his voice. My cock was starting to get harder. He definitely noticed this, giving him more confidence. "F-fuck... fuck me! Fuck me, Aaron!" I looked down at him. My cock was fully hardened now. "Well, you asked for it." He was still lying on the ground, so I reached down and grabbed him by the waist, pulling him up. When he was standing, looking up at me, I spun him around and grabbed under his ass cheeks. I lifted him up and lined my cock up with his asshole. I waited for a moment. "Just do it already! Please! Fuck me in the ass!" He screamed. Gladly, I dropped him onto my cock. His head fell back so that it was on my shoulder. With my hands under his thighs, he was completely off the ground. In one swift stroke, my cock was buried balls deep into my sissy's asshole. With his small stature, I was easily able to lift him up. Even though I'd just cum a few minutes ago, I was ready to go again. The fact that I was able to make my roommate seem so powerless turned me on so much. I bounced him up and down on my cock, enjoying his high-pitched moans and screams. I walked over to the bathroom in our dorm and walked in. I turned to face the mirror, where I could get a view of my sissy's worthless little cock bouncing up and down to my thrusts. "Look at you, bitch, you're just a worthless little sissy slut," I mocked. Having a full view of himself in the mirror made my sissy go bright red. He met my eyes and looked away quickly. I repositioned myself and picked up my sissy again, then dropped him hard on my cock. "Oh! Fuck!" He moaned. As I kept fucking him like this, his moans started getting louder. I could tell he was trying to hide his pleasure, but at this point, I knew that I was getting him close. "Look at me, sissy," I commanded. I wanted to see his humiliation. When he refused to look at me, I dropped him on my cock and stopped thrusting into him. "Look at me," I commanded more boldly. He slowly looked into the mirror, where he met my hard stare. He flicked his eyes away quickly, but looked at me again. His face was turning more red than before. I resumed my ministrations, but slowly. I lifted him up slowly, then dropped him hard onto my cock. "What are you, bitch?" I asked him. He looked at me, reluctant. "Tell me what you are," I commanded. He hesitated, then whispered, "I'm a s-sissy..." "What did you say? I can't really hear you," I teased. I started to fuck him a little faster now. I could feel my second orgasm of the night coming. "I'm a sissy," he said, louder this time. "And who's sissy are you?" I asked. I grinned, excited to hear the answer. "I-I'm... your sissy," he whispered between moans. Then he said it louder, "I'm your sissy. Fuck! I'm your sissy!" I started fucking him even faster. I moved closer to the mirror. This was a floor mirror, so I was able to walk right up to it. I was so close that I could even see the mist of my sissy's breath on it. "And what does my sissy want?" I was getting close. My sissy was getting close, too. "Oh fuck! Your sissy wants to cum! Oh! Your sissy wants your cock!" He screamed. That was it. Hearing that, I couldn't hold it back any more. I dropped my sissy onto my cock one last time. My cock spewed hot cum inside my sissy's used asshole. At that moment, he screamed, "Oh! Fuck! I'm gonna cum! Fuck!" His hands flew over the cage, shaking it like crazy. As soon as he stopped and held onto his cock, I reached my arms forwards and grabbed his wrists with my hands, pulling them away from his twitching cock. I wanted my sissy to cum hands-free. "Oh! Fuck!" His little cock shot one small blast of cum, which hit the mirror. Then another. And one more. Then, his cum just dripped out of his cock and down his shaft, sliding into his own asshole and along my own shaft. It then dripped onto the floor, along with my cum that was now starting to flow out of his abused asshole. My member shrunk out of my sissy's asshole with a satisfying popping sound, followed by a wave of my hot seed. I was exhausted, and my sissy was, too. I let go of his hands and grabbed his thighs once again. His legs were shaking. I grabbed him by the hips and slowly set him down. His legs wobbled a little bit, then they collapsed under him. I caught him before he hit the ground, and I helped him up to his knees. I grabbed the back of his head and smeared my cock on his face. After I wiped the cum from my cock off onto his face, I rubbed his face in the mirror, too, so that he was covered in his own cum, as well. Looking at the mirror, I saw a cum-drenched sissy slut. Nothing like the arrogant, stuck-up, rich roommate that I had before. Well, he was still rich, but that did nothing to help him in this situation. He knew that too. "Look at you. You're just a sissy slut. You're not even a man. In fact, I can't be calling you by your old name anymore. And while we're at it, I certainly can't refer to you as a male," I pondered. It's true, I just felt strange thinking of my roommate as a male. She is now a real sissy. "I'll call you Terri from now on, I think that's a very fitting sissy name." She looked up at me in the mirror, then broke into a silent sob. I helped her up and turned her around to look at me. She was still covered in cum, and I could feel my cock stirring again. But I think Terri deserved a rest. "Don't be sad, Terri, you're going to be the best sissy there is. And I know that'll make you really happy."