Reluctant Sissy Pounder

I'll cut to the chase here. I while back, I started going out into public in women's clothing. I didn't exactly pass at the time, but it was close enough for the dark bars and clubs that I visited. I figured it just had to be convincing enough to get them in the bathroom and suck their dicks. One night, I ran into a co-worker at one of the part time jobs I had and he recognized me. I chatted with him a long time and he was very sweet and promised not to tell anyone that he saw me in women's clothing. About a week later, he and I were working the same shift and he asked if I wanted to go out with him. I said sure and he asked me to dress up. We went out and had a great time. I went back to my place and I decided that I wasn't going to play games. I told him to have a seat on my couch and I went to get us drinks. When I came back, I just point blank asked if I could suck his dick. He seemed a little taken aback, but said he would like that. I got on my knees in front of him, unzipped his pants, pulled them down along with his underwear and revealed an absolutely massive cock. I stared at it in disbelief and he said, "It's ok if it's too big. You don't have to suck it." I told him, "Shut up," and wrapped my lips around it. You should have heard the little squeaky sound he made when I immediately pushed my head all the way down until my nose was touching his belly. I kept it there for a bit while I stuck out my tongue and licked his balls. When I finally came up for air, his cock was sloppy with my saliva. I jerked him off while I panted for breath and then I got to work. All the way down, then all the way up. All the way down, then all the way up. Over and over and over again. Each time I went all the way down, he made that same little squeaky sound. The whole time I was going to town on his cock, he was stock still; he didn't move a muscle. Didn't thrust his hips. Nothing. After a few minutes of working him like this, he said, "Oh shit. I'm going to cum" and tried pulling away from me. I put my hands under his ass and pulled my head all the way down and held it there while his huge cock throbbed out a load into the back of my throat. When it was clear he was done, I raised myself up and stood up to sit next to him. He then said, "I'm sorry, I don't know what to do. I've never been with someone with a cock before." I said, "Sweetie, don't worry, you don't have to do anything. I already came in my underwear." And it was true. As he shot his load into me, I shot mine into my panties. We got cleaned up and had a great rest of the night and he promised to take me out the following weekend.
The next Saturday, we went out, had a great time and went back to my place again. This time, I was determined to get him into my ass. I told him to have a seat on the couch and then I went to the bathroom and gave myself a quick enema, a wash and then I lubed the hell out of my ass. When I went back to my living room, I said, "Can I suck your dick again?" He readily agreed and I gave him the same treatment as last time, but after a minute or so, I looked up and told him I wanted him to fuck me. He got a bit flustered, but said OK. I hiked my skirt up a bit, got on all fours, moved my thong underwear to the side and told him to fuck me. He said, "Don't we need lube?" I told him that between what I already put in my ass and the huge amount of spit on his dick, we would be fine. He then very gingerly pressed his cock against my asshole and he slid right in. While he did have a massive cock, I have dildos that are roughly the same size, so it wasn't really a problem for me. He then proceeded to gently make love to my asshole. I told him to grab my hips and fuck me. He grabbed my hips but kept gingerly moving in and out. I told him to fuck me hard. He kept doing what he was doing. I started to push back against him quickly and he said, "Sorry." I then felt him quicken his pace and I reacted by pushing back against him so that he was against the couch and wouldn't be able to pull out. He grunted out a load into me and asked me what I wanted him to do. I told him to stay there and I fucked myself on his cock while I jerked mine. I shot a fat load on the floor after about 30 seonds. We got cleaned up and I asked him why he didn't fuck me hard when I asked. He told me that he's hurt women in the past with his giant dick and now he's afraid he'll hurt me. I tried to reassure him that he couldn't hurt me, but I don't think I convinced him.
Over the next couple of weeks, we fucked like that a few more times, with him always being gentle and then me taking charge and roughly fucking my ass with his cock. I finally had it though. I wanted him to fuck the hell out of me. So I came up with a plan. The next weekend, he came over and instead of going to town on his cock with my mouth, I figured I'd give him a lackluster suck. I licked the tip of his dick and put the head in my mouth a bit, and I did it all kind of lazily. He had gotten used to my Grade A blowjobs and I could tell he was getting frustrated. He asked if I could suck him a little more deeply. Instead, I just put the very end of his dick on my lips and then I started jerking him off, but poorly. He said, "Come on. Just suck it." It was the first time he was every demanding. I said, "I am," and kept doing what I was doing. After about 5 more seconds of bad cock licking, I told him it was time to fuck me. He was frustrated and I think he was a bit angry. So, when I got onto all fours, he didn't just gently put his dick in my ass, he slammed it in there. He said, "You like to play games? I have a game for you. It's called: Make the Sissy Scream," and then he gave me what I wanted. He fucked the hell out of me with all of his anger and frustration. I think he was a little ashamed that a "man in a dress" could make him want something so badly and then I didn't give him what he wanted. He railed my ass. He was up on his feet, fucking me like a machine. He thrusted hard and deep. After about a minute, I came hard, shooting cum all over the floor. He kept going. Another minute and I came again. He stood me up, walked me over to the dining table, bent me over and fucked me some more. He then pulled out, picked me up, put me on the table on my back, grabbed my ankles and went right back into my ass and gave me one hell of a fucking. I shot another load of cum, this time all over my belly. When he was finally about to cum, he grabbed my head, pulled me down onto my knees and then shoved his cock way into my mouth. The taste was awful (I had never done ass to mouth before) and then he throbbed out a massive load which almost made me gag. After that night, he saw that I could take whatever he could give to me and from then on he always fucked me hard.