A few days after our last encounter together, Brooke and I haven't talked much especially after what she whispered to me after we finished. Did she fantasize seeing me get fucked by other men? Did I? Kinda, but she's a lesbian, why would she want to see two dudes fuck? Anyway, my sex life had been pretty dry over the past few months so I was not gonna complain if she set me up with another guy. Then one night I decided I needed to talk to her about if she was serious, so I straight up asked her about it and she said, "Dead serious. I've been scouting out for guys all over the place but I really want to find the perfect man to be your daddy. Maybe we could scroll through dating apps later to see who you like?" Of course I said yes, so she had me download tinder and grindr on my phone. "Ooh, we have to dress you up for your new profile! Lets go to my closet." She exclaimed in the most excited way possible while dragging me into her room. I hadn't been in this room since we played with her toys last time so I was recalling some good memories. I became hard upon the view of her bending over to grab a sock on the floor, also because of the plug that I now keep in me at all times. She laid out some clothes over her bed and asked, "Do you want a more girly look or something more casual? Ah, who am I kidding? Your new bull is gonna want you showing off that nice ass in a skirt." I started to blush upon the compliment. I have to admit, for a guy, my ass is pretty nice so she was right. Women's clothes is a new thing for me so I was a little hesitant but Brooke would put me in line, with her finger in my face she commanded, "Strip. Now. You little sissy boy. If you're a good pup throughout this I might let you cum while we watch gay porn together later." Then suddenly she brings me in close, holds my balls in a death grip, and whispers, "I also noticed that plug in your ass. Does that pleasure remind you that you're mine? That you're life is mine to exploit. Until you and your little clit dick are swept away by a handsome hunk of a man who'll pound your holes into the night. But for right now, I'm your mistress and you'll do as I say. Now, get on the bed and let me put a cage on your little guy." She put that cage on my dick and I noticed it was a lot tighter. She had bought a new one which was a lot smaller but seemed to fit perfectly. I was humiliated by that fact that a smaller size was perfect for me but deep down I'm aroused by this humiliation. She told me to get up and try on some pink panties which she said I wouldn't take off until I was told so. Then she had me put on some white stockings and a green plaid skirt, finally she gave me a white v-neck shirt to complete the first outfit. "This will be one of your outfits, we won't need to shave you since you have no body hair like a real man would have. Now let me take some pictures." I went into some normal poses and she snapped some photos then had me get into more suggestive poses like pulling my skirt up to reveal my ass and having me spread my legs. After this, she had me get into several new outfits and we took photos of me in each one. I tried on different leggings, skirts, dresses, blouses, swimsuits, etc. I had never cross dressed before in my life but I secretly always wanted to try it, I was tired from all of it but it was a thrill to try all of girly clothes for the first time. She had me clean and organize the clothes as they were before then we created my profiles together which, admittedly, was exciting. Seeing myself in all of the new outfits made me believe that every guy on the app would be interested in me. I still had on a cute blue dress with little flowers on it, some see-through nylons, and the same pink panties. I uploaded my profile on both tinder and grindr and waited for someone to respond. "Come, kneel in front of me." She instructed. I got on my knees and crawled to her feet. "You were very good today. I'm proud of you. Now we're gonna watch your favorite gay porn together. Go retrieve my dildo, come back here, then sit on it and wait for my instructions." She commanded and I quickly did as I was told. I pulled the plug out of my ass, fingered myself with some lube, pulled my panties aside, and eased myself onto the big black cock. "We're gonna watch little white boys like you get pounded by hung, sexy, black cocks like the one you're gonna ride. You are to ride this cock until you come on my feet. Now start." As she turned the video on I began to rock on the dick, feeling my prostate engorge from the pressure. I squatted and impaled myself repeatedly on the thick dildo, then suddenly she put another black cock into my mouth. She didn't need to say anything for me to suck the non-existent life out of it. As I began to feel my orgasm building she pushed onto my shoulders and sent the entire cock in my ass so that i couldn't move, then said into my ear, "New instructions my slutty boy, as soon as you're done cumming on my feet, you'll eat all of it." This is familiar territory because I regularly swallow my cum after finishing. I began to build the orgasm inside me again and I knew that this was gonna be a big one. I waited for the perfect moment in the video where the black guy pulls the sissy's arms back and pounds him to hell, I blew up all over Brooke's feet and the floor. I continued to come for well over a minute until I had permission to lick my cum off her feet. I lapped up the sweet cum like a good boy with no hesitation and left no trace of it anywhere but my mouth. I waited at her feet until further instruction where she told me to clean up. I put away the dildo, cleaned up the sweat and saliva off of the floor and cleaned her room for her until she told me to sit on the couch. She cuddled me while we watched tv. "You were a very good boy today. As your new mistress I'll be very harsh on you but I'll also be good to you. I only want what's in your best interest. We'll get you that man of yours. Now go to sleep." She sent me off with a kiss on my cheek and a little slap on my ass. I couldn't help but sleep happy with this new dynamic in my life.