The next day he texted me again and wanted to meet again. I was eager to see him again as well. He asked me to come to his house fully dressed as a girl this time, instead of just wearing panties under my boy clothes. I told him I don’t actually have any girl clothes. Only a few pairs of panties. He seemed surprised by that and told me “you seemed like such a sissy, I thought you would have a whole wardrobe already!” He said “that’s alright. Let’s go shopping today and get you some new clothes”. I agreed and later that day we met at the mall. As always, he was being so nice to me and really making me feel comfortable with all of this. He only teased me a little bit here and there. We walked into a few women’s clothing stores to look at outfits for me to wear. I LOVE cute skirts and so I looked at quite a few, but I couldn’t really find any that caught my eye. Until he came from the other end of the store carrying this adorable pink skirt. It was just like one a cheerleader would wear, but a bit shorter. He told me “you would look so adorable in this”. I agreed. I picked out a cute white top with a heart on the front and some white tights to match. As we went to checkout he surprised me when he pulled out his card to pay. I wasn’t expecting him to buy the clothes for me. As we walked out of the store I thanked him and told him he didn’t need to do that. He patted me on the butt and said “it’s ok, I’m really excited to see you try this on”. I got shy and was blushing a bit. After that we went out to dinner and again, he paid. He was really treating me so well! I’d never been treated like this, he made me feel like I was a girl and he was taking me out on a date. Later that night, we were at his place again, watching a movie on the couch. We cuddled for a while, until cuddling turned into making out. We made out for quite a long time before he grabbed my hand and lead me to the bedroom where he sat me down on his bed. He pulled out the clothes we got from earlier and told me to put them on. He watched intensely as I stripped down to my panties, put on my top, slipped into my skirt, and slid the stockings up my smooth legs. This was my first time getting fully dressed up in girl clothes, and I did it right in front of a guy! I felt so slutty and embarrassed and turned on all at the same time. I got hard pretty quickly, and you could almost see my little dick poking a tent in my skirt. He told me to turn around and put my hands on the bed, bending over. I did as he asked and I could feel him come up behind me and press his body against mine. He flipped the back of my skirt up and began feeling up my ass and spanking it. Every time he spanked me a bit harder I let out a little yelp and he would chuckle. He put some lube on his thumb and began rubbing it on the outside of my hole as he asked “are you ready sissy?” I said yes, and he quickly plunged his thumb deep into my ass. I let out a louder yelp and my knees shook a bit, and I sort of fell onto the bed, my legs still hanging off onto the floor. He continued fucking my ass with his thumb for a while before he asked me “are you ready for something a bit bigger?” For a moment I thought he was talking about his massive BBC and a bit of fear rushed over me. But then I felt cold metal pressing against my hole. He had a medium sized butt plug with a cute pink heard at the base. He slowly pushed it into me until it was all the way in. I had never had anything more than a thumb inside of me before, but to my surprise it slid in pretty easily. I think the lube helped quite a bit. He patted me on the butt and moved my panties back over the plug and said “good girl”. My whole body quivered when he said that, and I had never felt more vulnerable. Here I was in this guys room. Fully dressed up like a slut, pantied and plugged. And I’ve never been more turned on in my life. After that, he flipped me around and pushed me down to my knees by my head. He pulled my head up close to his jeans and said “are you ready to suck your first dick today sissy?” I looked back up at him from my knees and shyly said “yes daddy”. He said “good girl. Now take off my pants. I quickly reached out to take off his belts but immediately he grabbed my arms and held my hands out above my head. He said “not like that sissy. Use your mouth”. The way he demanded it was so hot, and I love a challenge, so I smiled and perked up on my knees, and began trying to undress him with my mouth. The belt was a bit of a challenge but I eventually got it off. The rest was a bit easier. As I grabbed his zipper with my teeth and began to pull it down. I could see his massive bulge in his underwear. He was only half hard and his dick was already 3x bigger than mine. Before I pulled down his underwear with my mouth, he grabbed the back of my head and pulled it right into his dick, and said “kiss it”. The way he was acting so dominant with me got me so excited and I would do anything he asked me to. I dug my face deep into his dick and balls and began kissing all over. His manly smell was intoxicating and I would take deep breaths in as I made out with his massive dick. I couldn’t tell who was enjoying it more, because we were both rock hard at this point. He yanked down his underwear and said “alright sissy, show me how you suck a real cock”, before slapping my cheek a few times with his thick cock. He still hand both my arms pinned above my head, so all I could do was grab the tip of his cock with my mouth and try to start sucking. It was so thick I could barely even fit my lips around it at first. It took me a while but eventually I had his whole head in my mouth and I began rocking up and down on his massive cock. I tried swirling my tongue around the tip like I’ve watched all those porn stars do so many times. I could tell he liked it too as he twitched and said “damn baby. You’re a natural cocksucker”. I was so turned on I was almost ready to cum and I wasn’t even touching myself! He grabbed the back of my head and started pushing it down deeper onto his massive BBC. I gagged a bit and he laughed. He said “good job baby” and continued. After a while he was thrusting his dick down my throat and he was going faster and faster. I had been gagged by his cock and was covered in drool that had fallen down all over my chest and legs. As his speed reached a climax, he pulled his cock out and said “I’m about to cum baby”. Without even thinking, I instinctually squatted down low, tilted my head back, and stuck out my tongue, ready to catch his cum with my face. He pulled his cock right up to my face and jerked off a huge load. It shot all over my face, forehead to chin. I caught a lot of it in my mouth, and I swallowed what I got. I then put his dick back in my mouth and sucked out every last drop, and cleaned the tip. After swallowing all the cum I could, I let out a giggle just out of pure excitement that I had made a man cum with my mouth for the first time ever, and swallowed his cum…