First, about me: I'm 45, recently divorced, 5'4" tall, 138 lbs and have a 4 1/2 inch cock. I've been successful in sales and can afford just about anything I want.

Since my divorce I've gotten interested in trying lipstick and makeup, and even bought a dress and bra. On Fridays I dress up and lounge around the house stroking my tiny cock. I've never been with another man, but have been curious.

A couple of weeks ago I was dressed up and looking on C/L to try my hand at a man. The ad said he was looking for a sissy slut to fuck. I thought I'd give it a shot, so I answered the ad.

He was 24 years old, 5'8" tall and weighed 280 lbs. When he answered the door he had on a robe, and nothing underneath. I confessed to him that I hadn't done this before, and he assured me that after tasting his cock I would want it all the time. He kept the robe on while we sat on the couch. He brought me close and started kissing me. His lips were surprisingly soft, and when he stuck his tongue in my mouth I responded eagerly.

"Here's what's gonna happen," he said. "Tonight, you're my bitch. You do what I say and no one gets hurt." I was a little worried now. "Okay, first you're gonna suck my cock and swallow my load. Then you're gonna eat my ass until I tell you to stop. Then you're gonna suck me again until I'm ready to fuck you. I won't touch your cock, but only use you as my whore. Got it?" "Um, I'm not so sure about anal." "That's too fucking bad," he said. "It's gonna happen."

I told him I had made a mistake and thought I'd better leave. Instead, he grabbed my arms and held them behind me and led me to the bedroom. I was stuck, not knowing how I was gonna get out of this. He closed the bedroom door and dropped his robe. He had the biggest fucking cock I'd ever seen. It dwarfed my tiny one, and was about as thick as my wrist. Now I was really scared. "Okay, bitch, get to it." His cock hung there limp. When I didn't move toward him, he came to me. He pushed me on the bed and grabbed my nuts. "I'm gonna hang onto these until you beg me to fuck you." I was on my back, and he positioned himself next to me so his cock was at my mouth but could still hold my nuts hostage.

I tentatively opened my mouth and took his cock in. Instantly it started to grow. It was fucking huge. My jaw was stretched to the limit. He mouth fucked me for about 10 minutes and said he was gonna cum. He squeezed my nuts a little and told me I had better swallow it all. I Tried. He had a bucketful of cum in those balls, and as hard as I tried I couldn't take it all. He did, however, allow me to lick all the spilled cum off of his balls and cock, and made me suck him until he was clean.

"Good," he said. "Now, on your belly, faggot." He hung onto my balls through it all, and when I was on my belly he ordered me to spread my legs. In one quick motion he shoved two wet fingers into my asshole. It hurt like a bitch. I yelped. "Shut up, sissy, we're just getting started." He began to finger fuck me, and soon the pain went away and was replaced by pleasure. "You like that, don't you, cunt?" I shook my head yes. He continued to finger fuck me until I was pushing back each time he thrust his fingers in. "Tell me to fuck you," "I want you to fuck me," I said. "Turn over." I rolled over onto my back. He repositioned himself so his asshole was right at my mouth. "Now tongue fuck me." I thought this was kinda nasty and didn't move. He squeezed my nuts hard enough that I immediately thrust my tongue into his asshole. I tongue fucked him for a few minutes and his cock was finally hard. "Tell me again to fuck you." "I want you to fuck me," I said for the second time.

He moved around so he was kneeling between my legs. He let go of my balls finally and pushed my legs up toward my chest. He had a hard time pushing his cock in, but finally did. I tried to relax as much as possible, and eventually he slowly started to fuck me. Again, it hurt at first, then subsided. I was actually enjoying getting butt fucked by this massive cock. He must have fucked me for a good half hour before being ready to cum. He tensed up, thrust forward and started cumming. It was another big load, and some of it seeped out of my ass.

Finally spent, he pulled his cock out and told me to get undressed. "Now comes the best part," he said. I thought he was going to suck my cock, but instead he led me to the bathroom. "Lay down in the tub." I had no fucking idea what this was about, but was afraid not to. As soon as I was on my back, he got in and stood over me and started pissing. He must have been saving it up for a while, 'cause he pissed a bucketful. Mostly on my cock and balls, but some on my chest, and even hit my face a little. The warmth of his piss and the fact that I was still horny made for an exciting experience.

When he was done pissing, he shook his cock a couple of times and told me to sit up. I did, and he put his cock back up to my lips. "Now, make me cum again." What a stud. This would be the third cum of the evening. I wrapped my lips around his cock and he began to fuck it. It was still able to get hard, but it took a long time for him to cum, at least 30 minutes. When he did start to cum, he gave me no warning this time. He just let it fly. I wasted his cum all the way down my throat, and it was a much smaller load than the other two times.

He was finally done, and I had sucked him dry. He got out of the tub and told me that was it until next Friday. It was painful, humiliating and degrading, and I can't wait until next Friday when I can be his sissy again.

I grew up with a fucking whore for a mother. My dad left us when I was three because my mom would fuck anything with a cock. So she was left to raise me alone. Her frequent suitors thought it was cute when she put lipstick on her cute little boy and paraded him around the house like a mini-whore. When I was eight years old she made me share a cock with her. So, growing up a sissy wasn't much of a stretch.

By the time I was 10 she would make me suck a guy off first, making him cum, then she would fuck him. By the time I was 15 I was a fell-fledged sissy. I was pretty small, only 5'4" tall and about 115 pounds. I didn't know until high school that this wasn't normal for a boy. I was the freak of my class, and would often get abused by the football team.

I moved out right after high school. I didn't want to be my mom's sissy anymore. I got a job with the state as a clerk, but after trying to live the straight life, I realized that the sissy in me had to emerge. I started going to the gay bars every Friday night, sucking cock and getting fucked at every chance. My asshole got so loose that I was able to take a nine inch cock in my ass, and constantly looked for bigger and bigger cocks to suck and fuck. I was a true cum slut, and found I couldn't function unless I had a cock for dessert.

Eventually I started dressing like a woman, and with my petite frame I made quite a good looking gurl. I couldn't believe so many real men would pay a sissy slut like me in my make-up and lipstick so much money just for the pleasure of putting their cock in my asshole.

I left my job with the state and concentrated all of my efforts on my new found source of income, and to this day I make nearly six figures sucking and fucking all the married men who need a real woman to take care of their cocks.

I posted I was looking for a dominate man. I'm a 50 year old married man looking for something a little kinkier than I get at home. This guy answered the ad and said he was a dom and invited me over.

When I got there a very tall, fat man answered the door. Not quite how he portrayed himself online, but I went in anyway. He immediately told me to strip. When I was naked he cuffed my hands behind me and led me to his basement. I was suddenly scared. He had more dungeon equipment than I could imagine. He took me over to a stockade and had me kneel down in front of it. He put my head through the hole and locked me in. He walked in front of me and took off his pants. He had the biggest cock I had ever seen. Even soft it was about 7 inches long. He stepped forward and told me to suck it. I opened my mouth a bit and he put his cock in. I could barely fit the head of his cock in my mouth. Slowly he started to grow. When he was hard he pulled his cock out of my mouth and walked around to the back of me. I fully expected to get fucked, but instead I felt something cold and rubbery being pushed into my ass. I had been fucked before, so I knew what to expect. He started to fuck me with that rubber thing. Then he slapped my ass. Hard. Each time he pulled that thing out he slapped me. After about a dozen slaps I started to cry. He started calling me sissy and queer-cunt and other sub names. He must have fucked me and slapped me for about 15 minutes before he pulled it out of my ass and walked back in front of me. His cock was still hard when he put it up to my lips and told me to open up.

I sucked him the best I could, his belly slapping my forehead each time he pushed his cock in. He pushed in as far as he could, but his cock was so big I couldn't even get half of it in my mouth. I was choking and gagging each time he hit the back of my throat, but when he started to cum I almost had a heart attack. He had so much cum it literally squirted out of the corners of my mouth. He had big nuts and had stored up for quite a while. He had more cum than anyone I had ever seen, and probably 5 times the amount of cum I produce. He finally pulled his cock out, and it was still hard.

He walked around to the back and said, "Now, cunt, you're gonna feel my cock split you in two." I begged him not to fuck me, that I would do anything he wanted if he wouldn't ass fuck me. He just laughed. He knelt down and I felt his cock at the opening of my ass. Luckily it was slippery from his cum, but when he shoved his cock in my ass I felt a shock of pain like never before. I tried to relax, but it didn't do much good. I was crying, screaming, and squirming trying to get away. He wasn't having any of it. He started slapping my ass again, telling me to man up and be a good little cunt. He fucked me so hard and so fast I passed out from the pain.

I woke up to a slap in the face. It felt like hours, but it was only a couple of minutes. When I was coherent again he walked behind me again and shoved his cock back in. I screamed again. He was right when he said he would split me in two. It felt like a baseball bat up my asshole. He fucked me for a good half hour. He finally pulled his cock out of my ass, and I was totally broken. He walked in front of me and started jerking his cock until he started to cum. He hit my forehead, my eyes, my nose, and finally shoved his cock back in my mouth for the last couple of squirts. He had me clean his cock off, and when he pulled out he just left.

About two hours he came back in and I felt him examine my asshole. He pulled me out of the stockade and undid my cuffs. He had me lay down on a massage table and pulled me to the end so my ass was hanging off the end. Then he squirted some lube in my ass and started to fuck me again. It didn't hurt as much this time, but I was too emotionally and physically exhausted to fight him. After fucking me for another 20 minutes he pulled his cock out and came all over my belly and cock. My own shriveled 3 inch cock was dwarfed compared to his. When he was done he walked up to my head and had me clean his cock off with my mouth. when he was totally clean he told me to get dressed and get the fuck out.

Humiliated, spent and totally broken, I got dressed and limped out. It took three days before my asshole closed up enough that I could hold my shit in. I had to wear my wife's tampons in my underwear, my ass leaked so bad. The tough part was keeping my plight from her until my ass was back to normal. It was the worst experience of my life, and I can't wait to do it again. Fuck, what a night.