Exploring Crossdressing with a Close Friend

"hold still!" He said, and he slowly pulled the razor up my butt cheek. He was the only gay friend I had, and I'd confided in him that I liked to cross dress. He thought this was amazing and wanted to teach me how to "manscape" and wanted to help me learn some tricks. He had offered to help me become smooth, and I'd obliged.
"Have you ever had an enema?" He asked. "Uh, no." I replied truthfully. "Well, I've got a kit that I brought, so I'll teach you how to do that too." I was hesitant, but why not? This was a lifestyle choice, and I needed to learn all the ins and outs.
He finished and we went to the bathroom. I was legitimately smooth, I loved the feeling. He explained how to do the enema, and I followed his instructions. When I was sufficiently cleaned I came out of the bathroom.
"Wow!" I said as I realized he'd picked everything out for me. Matching bra and panties, garter belt, skirt, thigh high stockings, stilettos, and a tight stretch top that would reveal my belly button... And a fake belly piercing to complete the ensemble. Also a wig, and a makeup bag.
"Makeup?" I asked.
"You silly, you know I was a theater major. I know all about applying makeup. I played a woman in my last three roles."
This was exciting.
After about an hour I was all done up. I looked in the mirror. I was pretty passable, and so smooth.
"You know I'm a top, right?" He said
"I don't know what that means, I replied."
"Well, there's tops, bottoms, and vers... The tops are the guys that like to penetrate, the bottoms are the penetrated, and the vers do both. It means versatile. Which are you?"
"Wow, I've never thought of it, but I guess I'm a bottom of I look like this."
"Well then, suck me."
I turned and looked at him. He was actually very attractive, and he wasn't wearing a shirt. "I've never done it before." I said sheepishly.
"Yeah, I figured as much, but you need to practice if this is going to be your lifestyle." "Okay," I said shyly.
I approached him, put my hands on his chest and got down on my knees. I pulled his pants down and wow. He was well endowed. I guess I thought since he was gay it would be small or something, but wow.
I slowly opened my mouth, my heart was pounding, I stuck my tongue out and tasted it. Not bad, I opened my mouth more and he slid it in. I gagged... "You'll get used to it." I sucked and found a rhythm. It was fun. I could tell he was enjoying it.
After a few minutes he put his hands behind me head and started pushing it in deeper. "Relax your throat and swallow as I thrust." I tried and wow, he got in balls deep. I couldn't breathe and my gag reflex kicked in. "Wow!" He said, "you're a natural!" Let's fuck!
Before I knew it I was on the bed on my knees and he was behind me. He lubed me up with his spit and I felt the head of his dick against my freshly cleaned hole. "No wonder he brought an enema kit," I thought as he pushed. It slid in and my whole body tensed up. "Relax" he whispered in my ear. He was hard and I could feel him deep inside of me. He began to thrust in and out, in and out. Occasionally he'd push in real deep and pause. He was trying to go deeper and deeper. I started getting hard...
"Oh my!" I gasped, "I'm going to cum"
"Let it happen." He said as his hands moved to my hips. Each thrust came deep and faster, deep again. Each deep push got me closer and closer...
"Uuuaaaahhhhh!" I moaned as my body released my load. My sphincter spasmed as I orgasmed. This really got him going. Faster, deeper, faster deeper. He stiffened, pushed in as deep as he could. He throbbed, and huffed, *boom!* He exploded inside of me.
"Oh my God!" I shouted. "That was the best ever."
"Oh, we're not done!"
He pulled out, had me look at him. I examined his dick. It was clean, except for his cum. "You have to swallow. You're not a sissy bitch until you swallow cum from a cock that's been inside of you."
I opened my mouth, leaned in, "I'm a sissy bitch"