I am a 25yo male. I have a fuck buddy from a couple years ago that I stay in touch with as friends. She is a traveling sales rep, and is always on the road.

We havent hung out in a while and we finally got together for dinner last weekend. She looked so sexy in these tight white pants, high heels with her long sexy legs up to her beautiful ass, and low cut shirt showing off her tits. We had a few drinks and we fucked, I fisted her, and she gave me an amazing massage until I fell asleep.

I woke up with her straddling my face and I eagerly started to lick her pussy and she leaned down to start sucking my cock. She stopped after getting me really hard and wanted to cuff me down to the bed. We have had kinky sex before so I was game for it. She had the cuffs already attached to the bed and had me cuffed spread eagle really quick.

She went back to grinding her pussy on my face and sucking my cock. I was soon cumming her in mouth and she squirted all over my face. She moaned and asked me if that was a great blowjob. I said of course it was...

She then got up, opened the drawer next to the bed, and pulled out a chastity cage. She gave me this sexy but evil glare and locked up my cock. I thought it was a joke.

She climbed on top of me and rubbed my locked cock against her pussy. She told me that she missed my cock and wanted to keep it for herself. I instantly lost the smile on my face and asked if she was serious.

She put the keys around her neck on a necklace and said that she will be back in town on Friday. She got up, let me up, made me get dressed and sent me on my way.

At first I thought it was kind of a hot game, it wont be too bad. I have been extremely horny all week and she just told me today that she will only unlock my cock if I cum from her fucking me with a strapon tomorrow. Im so desperate to cum I would beg for her to fuck me. I will keep you posted on what happens.

It all started after I just got a divorce and had to rent a room in a house in town. I had just lost my job and had just started a new one at entry level pay. I shared the house with two brothers, John and Jack that had inherited the house from their grandmother. They were both jocks that went to the gym everyday and loved sports. I was the opposite kind of small and thin and never really played sports. After the divorce I didn’t really want to have any girlfriends. I started looking at porn on my laptop and started to like the sissy stuff. I wasn’t gay and had always been with women. For some reason this stuff just turned me on. It all started off innocent enough. I would jerk off to sissy porn and then started watching sissy hypno videos. After a couple months went by when I bought my first panties. I never wore them when the brothers were home just when I had the house to myself. I almost died when I left a pair of thongs in the dryer and John found them. They started joking that I must have a new girlfriend and wanted to know when they were going to meet her. I just joked back and told them it was a one night stand. They laughed and congratulated me like I had just scored a touchdown. I had let my hair grow long and told them it was because where I worked they all did. I started driving to the city and trying to buy more stuff. I wanted to buy some stuff like skirts, blouses and shoes. The hardest thing to buy were things like bras, stockings and thing like that. Even though nobody knew who I was I still felt uncomfortable buying these things. I think the way I was embarrassed, they knew I was buying them for myself. Sometimes I would just walk out of the store because I was so embarrassed. That when I decided to start using Amazon. I went crazy! I could buy whatever I wanted and never had to go to a store. I bought all kind of stuff to dress up in. I was going to the post office almost every day. Then things like dildos and things like that started to be recommended to me. I started to try some small dildos and plugs. Oh god I loved it! The more I used them the more I wanted something bigger. I started buying ones that looked like dicks and they were a lot bigger than mine. I got a chastity devise and lock my penis up. It was so cool to not to be able to jerk off when I played my games. I would get horny as hell by not being able to cum for days. That may have been a bad thing looking back! Like I said the guys went to the gym every day and went to the bars most nights so I had the house to myself most of the time. The only problem was the hornier I got the more chances I would take. I almost got caught a couple of time. I swore not to take the chance of getting caught. One day we were all in the kitchen talking and Jack said something about ordering something on line and like a dumbass I said that I had an Amazon account. He said it would be great if he could just use my account to order his stuff. I didn’t know what to say but sure. I immediately went to my room and deleted my history and thought please don’t let him see what I been buying. I thought I had deleted everything and took my laptop to Jack’s room. I logged on for him and he was searching for what he wanted when John called me in to the living room for something. When I got back to Jack he was done ordering and gave me my laptop back and said he would pay me when his stuff came in. I thought everything was ok because everything was normal for a couple of days. Then three days later Jack came in and said John was out for the night and he wanted to talk to me. I sat on the couch and Jack was walking around then he said “I seen the fucked up shit you have bought on line.” My heart dropped and my stomach turned! I didn’t say anything. I just look at the floor and hope it would all go away. It didn’t. Jack said I knew there was something funny about you. Now go upstairs and get changed. I’m going to take a shower so don’t be too long! My head was spinning. I didn’t know what to do. Then Jack yelled “you better get your ass moving sissy or I’m going to stomp your ass in the ground.” I ran upstairs and slammed my door with all kind of thoughts running though my head. I didn’t want to dress up but, I was afraid Jack would kill me if I didn’t do as he said. I grabbed a skirt and blouse off the floor and put them on real fast. I already had panties on. I found some socks and tennis shoes that I had bought for that outfit and put them on. I looked in the mirror and thought to myself I got to do better than this. He’s going to beat the shit out of me. I knew I didn’t have time to put on much makeup so I just put on a little blush and lipstick and pulled my hair up in ponytails to help me look like a girl. I was out of breath and shaking knowing nobody has ever seen me this way. I ran back downstairs and heard the shower still running so I sat on his bed trembling. I heard the water stop and I knew he would be out soon so I tried to relax so he wouldn’t be mad. When I heard the door open my heart stopped. He walked in to the room and said “Holy fuck Scott.” He just stared at me for a while and then said “You make a good looking sissy you little faggot.” I just sat there not knowing what to say when he started to get angry again. Calling me names, saying he was going to tell everyone about me. I started crying a little and he kept yelling. I kept saying I was sorry and begging him not to tell anyone. He pushed me down on the bed and I thought he was going to hit me. He started calling me names like sissy bitch, pussy boy and told me I probably like sucking cocks too. I told him that I wasn’t gay and he just laughed. He took out his cell phone and started taking pics of me. I’m going to let everyone enjoy these. He said he was going to call all the guys at the gym and have them come over and fuck my sissy ass. I kept begging him not to and was really crying now. He said for now on he would call me Sue. He said Scott is not a good name for a sissy faggot. I was lying on the bed curled up in a ball crying and thing got quiet. I looked up and Jack was just standing over top of me. For a few minutes I didn’t know what he was going to do. I felt him sit on the bed and after a while he said “Sit up Sue we need to talk” I sat up and he said it would be ok and not to worry. I was wiping my eyes and he put out his hands like he wanted a hug. I was so confused I didn’t know what to do so I leaned towards him and he gave me a hug. The hug was lasting a long time and he pulled my legs over his lap and was rubbing my back and arms. He kept saying over and over that it will be ok. I was really getting uncomfortable from his touching when all of a sudden he grabbed my ass. I was shaking and afraid to say anything. He kept saying things like “Don’t worry, it will be ok and just relax.” The whole time he was rubbing my legs and ass. For some reason his touching me was beginning to less revolting and my comforting. I almost felt myself start to cuddle up to him. Then he said something that made my fears return. He said “Just do as I say and it will be ok. All you have to do is relax and enjoy this.” I wanted to run but I knew he would get mad again so I just sat there with him while he felt me up. His hands were everywhere, on neck and face, on my arm and the whole time with one on my ass. He put his hand inside of my panties and was squeezing and pulling on my ass cheek. He slid my panties down and was really working on my ass. He started breathing more heavily. A chill ran down my spine when he said “I think it time for you to get out of some of those pretty clothes. I started to pull away and he pulled me in really tight and said “Just do as I say and everything will be ok.” I went limp from defeat and he sat up and pulled me in to a kneeling position. I just close my eyes and let him take control of me. He started to pull on my sweater and blouse until it was pulled out of my skirt. He pulled my sweater up but, I still had my arms down and he said “We can do this the easy way or the hard way. Just do as I say and you might enjoy this. You are a pretty girl. Now act like a pretty girl.” I knew I didn’t have a choice so I raise my arms above my head and let him take my sweater off. After Jack got my sweater off he stood up and looked down at me and said “Sue are you going to be a good girl or am I going to have to call for some help.” I just looked down and didn’t say anything. I heard him pull his cell phone out and it sounded like he was dialing a number. I thought he was bluffing about telling his friends but when he started talking to one of his buddies from the gym named Brice I looked at him in shock. Brice was a very large black guy that was always mean to me. He would always push me around or put me in a head lock. Brice would call me names like little man. I had heard them joke with Brice about the size of his dick. He called it his cunt buster and rectum wrecker. I didn’t have any choice but to look up at Jack and say “I will be a good girl Jack. Please don’t let Brice come over here. I will do anything you want me to do. Please!” Jack looked down at me and told Brice that he had to go because he had a hot bitch on his bed that needed his attention. I don’t know what Brice said but, Jack said he would call him if he needed any help with this cunt. Jack hung up and said I was lucky because Brice would have split my ass in two and if he has any more problems with me that I wouldn’t be able to stop him from calling him to come over. Jack started taking off his clothes and I just sat on the bed looking down, kind of whimpering. I felt Jack approach the bed and said “Time to show me how good of a girl you can be Sue.” I looked up at him. He was naked and looked huge standing over me. He was pulling on his dick and looking down at me. He moved as close as he could to the edge of the bed and ordered “Lick my balls Sue.” I was scared to death and not knowing what to do. I remember thinking it was funny that he was completely shaved. I closed my eyes and stuck out my tongue. I leaned in until my tongue hit him balls. I was trying to think what I would want a woman to do to me when he barked “You better get busy Sue or I’m going to make a call.” I started licking like crazy not knowing if it felt good to him or not. He started to moan so I figured it must be ok. As I licked his balls I took my mouth and started to suck on them to. He seemed to really like that, so I continued to lick and suck on his balls while he was pulling on his dick. He got his phone and was taking more pics and videos. I was able to suck one of his balls in to my mouth and lick it while I sucked on it then I would change and do the same thing to the other one. I thought I must be doing ok his cock was getting really big and he wasn’t threatening me anymore. Then he let go of his cock and it hit me on my forehead. Jack ordered me to suck it. I had never sucked a dick before but I did pretend with my dildos. I figured it would be the same, but it was different. It was warm and soft and bigger than my dildos. I was full of mixed emotions. The man in me wanted to fight back and to stop this, but there was a part of me that wanted to take his cock in my mouth and suck him as deep as I could. He wasn’t moving a bit so any movement was me. The more I sucked his cock the more I wanted to suck him. Now I was rocking back and forth while sucking his cock taking more and more every time. I found myself hoping I was doing a good job and hoping I was better than any women he had fucked before. The thought crossed my mind that I better make him cum or he might want to fuck me. I started to really work on his cock. I grabbed it with my hand and started to jerk him while I was sucking the tip. He was breathing heavy and I thought he was going to cum. Then he pulled my hand off his cock and shoved it all the way in my mouth. My nose was pressed against his stomach and his cock was down my throat. He just held me there for a while. He slowly pulled back and pulled my ponytails so that his cock went all the way in my throat again. I couldn’t breathe when he was all the way in. He would release my hair and I would pull back and catch my breath. As soon as I did he would pull my hair until I was pulled back to the base of his cock. I tried to push back against his thighs to get his cock out of my throat but, the more I pushed the harder he pulled my ponytails. Finally I gave up and let him fuck my throat and hope to get a gasp of air when he pulled back. I was exhausted from the assault on my mouth. Jack started to slow down and was just slowly fucking my mouth. Jack pulled his cock out of my mouth and leaned down and whispered “Ok Sue, it’s time to give me some of that sweet ass of yours.” He pushed me down and pulled my legs towards him. In one swift move he twisted my legs to make me turn over and pulled my hips up so that I was on all fours. Jack opened a drawer next to the bed and grabbed a bottle of oil. He poured some on his cock and I felt it run down the crack of my ass as he poured it on me. Jack said “Reach back and spread that ass you little fucking faggot. I’m going to fuck you so hard you are going to beg me to stop.” I reached back with one hand and pulled my ass cheek. His cock was sliding up and down my ass crack. I almost wanted to thank him for using the oil. His cock was a lot bigger than anything I had put in my ass before so I was really scared. When I played with my toys I would go nice and slow so I could get used to the size. I pleaded to Jack to be easy and he started laughing. I knew he wasn’t going to be nice. Jack was rubbing his cock around my asshole but, not sticking it in. That’s when he leaned in and said “I want you to fuck my cock sissy. Don’t go slow, don’t be easy just slam your ass back as hard as you can. I want you to make it come all the way out and then slam your ass back down on it. Don’t stop until I tell you too.” I begged him not to make me rape my own ass. I was starting to cry. I know even my smallest dildo didn’t go in without a little discomfort and he wanted me to take his big cock that was twice the size of anything I had ever tried before. Jack was starting to get impatient. He reached around and grabbed my throat so I couldn’t breathe. He said “Get busy you little whore or I’m going to shove my fist up your ass. You would probably like that wouldn’t you.” I tried to say something but, I couldn’t talk with his hand on my throat. He released me and I choked as I said “Please don’t. I’ll be a good whore.” I knew what I had to do so I made up my mind to just get it over with. I could feel his hard cock at the entrance of my asshole so I pushed back to build up pressure and with all my force pushed back as hard as I could. His cock slid all the way in to the base and I screamed in a high pitch squeal. My ass was burning like I had just sat on a red hot rod. I was panting rapidly not able to catch my breath. Then he hollered “Pull it out”. I leaned forward until his cock was out of me. God it hurt just as bad going out as it did going in. Jack ordered me to do it again. I began to repeat the process of me slamming my ass down on his cock and pulling away until he was completely out. It was still hurting like hell but I guess my ass was starting to stretch to the size of his cock. After a few times I was getting into a rhythm when I heard him say “They are going to love this.” He started saying “Come on you fucking whore fuck my cock.” I knew he was videoing me fucking his cock with my ass. The more I repeated slamming his cock in my ass; I could feel myself starting to get aroused. My dick was getting hard and my ass was tingling. After several minutes I found myself getting into this experience. I would moan every time his cock would enter me and squeezing my ass trying to hold it in. I was a whore. Jack told me to stop and I heard myself moan a disappointing sound. He pushed me away and laid down on the bed. He pulled my hair and pushed my face towards his cock and said “Suck my dirty cock you fucking little slut.” I was way past the point of refusing. I pulled his cock in to my mouth like I was starving for it. I needed him to be satisfied. I was his slut and it was my duty to please him. I had sucked his cock and balls and fucked his cock with my ass. Now it was my responsibility to make him cum. I was sucking him like a crazed whore. Jerking him and sucking him all the way to the base of his cock. While I was sucking him I reached down and started jerking my own dick. I was a horny slut needing to cum. The more I pulled on my dick the more effort I made to get him to cum. I heard him chuckle and point his phone at me. Then he said “What a nasty whore you turned out to be. Now beg for me to cum.” I knew it was another video so I pulled my mouth off his cock and said “Please Jack cum for me. Feed me your cum. I need you to cum in my mouth. I will be your whore forever. I will suck your cock, lick your balls and fuck you whenever you want. I will be your nasty slut to use anyway you like. PLEASE just cum for me!” I was so close to cumming I would have said anything. Jack got up and stood beside the bed and said “Open your mouth bitch.” I sat up opened my mouth and stuck out my tongue while he stood in front of me jerking his cock. He started to cum and shot his cum on the side of my face. He moved closer. I could feel load after load hitting the back of my throat and on my tongue. Jack pushed me back on the bed and took several pics of me with my cum covered face and said “Fuck Sue that was awesome. I can’t wait until tomorrow!”

My girlfriend, Leann, of 2 years has kept my cock locked in a chastity cage for the past 18 months. Unlike most women that lock up their cocks, she forces me to cum at least 3 times a week. She does not allow my cock out, but forces me to cum from being fucked in the ass. Normally she likes to fuck me with a strapon, but sometimes she makes me ride a toy by myself or fists me.

She does unlock my cock once a month for a weekend and allows me to fuck her, but mostly tortures my cock or teases me even more. Being unlocked doesnt always mean I get to cum.

My girlfriend loves to bring men and women home and forces me to watch them, clean their cum out of her, suck the mens' cock clean, allow women to sit on my face, but my cock and ass belong to her. She has never allowed anybody else to use me that way.

She frequently visits a local strip club and I have never been allowed to go with her, but she has brought home some of the girls and occasionally a fellow patron.

Last night Leann allowed me to go to the strip club with her. She left my cock locked up and made me wear a butt plug.
When we arrived it was clear that she visited often because almost everybody there knew her, but even when they said hi to her they ignored me like I didnt exist, but I am used to that.

After watching a dance and saying hi to a dozen people. Leann took me back to one of the private dance rooms and had one of the girls come in. She told the girl that this was the special dance she told her about and the girl just giggled and started her dance on my lap.
My girlfriend watched in the small room with us as this girl pushed her tits into my face, put my hands all over her which I thought was against the rules so I hesitated.

She sensed my hesitation and got pissed. "What? Am I not good enough for you to touch faggot?" I was shocked and didnt say anything which made her even more mad. She slapped me across the face and stood up. She turned around and her ass was right in my face. I am a huge ass man and it turned me on so much. "What about my ass fag boy? Do you like that?"
She grabbed me by my hair and pulled my face into her ass. Her G-String was practically non-existent. "Lick it bitch"

This time I didnt hesitate, I started tongue fucking her sexy ass and after about 15 minutes she squirted all over the floor. I was so turned on and my cock was straining against its cage, my ass clenching onto my plug, I started to beg Leann for permission to cum.

The Dancer and my GF started laughing at me and making fun of me which just turns me on even more. The Dancer said "Shut up an keep tonguing my ass faggot". But this time she was sitting on the bench type seating next to Leann kind of slouched down. It took a little longer but she eventually squirted all over my face and I couldnt help but start cumming myself.

I instantly confessed to Leann and she was pissed that I came without permission. She asked the Dancer to go get "James". Leann squeezed my balls hard and slapped me as punishment while we were alone.

After a few minutes the huge black bouncer from the door was in our private room. He and Leann knew each other and I imagine she has probably came home with his cum for me to lick out of her before, but I havent seen him before.

She thoroughly enjoyed telling James about every detail of the events leading up to this moment. They both laughed together. Leann was dressed like she could have been one of the Dancers just before getting naked. She had a tiny lil skirt on, sexy lace panties and matching bra, and one of those designer cut up shirts with huge heels.

Leann made me crawl over next to James as she did a sexy strip for him and once she was naked, sat on the other side of him and slowly pulled out his cock. I was mesmerized. I have seen BBC porn, sucked a few black cocks, but never seen one this huge.
She just held it and slowly stroked it telling me "James is OUR new boyfriend now." She made a point to say OUR and explained that James loves lil white cuckold cum sluts almost as much as he loves white girls with asses. She told me how I would be his bitch now as well as hers and that I would worship his cock as mine was no longer allowed to fuck her anymore.

Leann made me get on my hands and knees, put my face down in the spot thats still wet from when the Dancer squirted all over the floor. At first I thought about how gross the floor was but then she pulled the plug out of my ass.

Leaan spread my ass open and I felt so exposed. She looked up at James and said "Daddy, please come use your new little fag boy"

James came up behind me and I felt his hands on my lower back/hips. "Say fuck me Daddy"

I did, I called another man Daddy and begged him to fuck me. This was the first time I have ever had a real cock in me and it felt like I was being fucked with a baseball bat. I wanted to cum but all I could do was beg for my new Daddy to cum in me. I wanted to please him so badly.

James came in my ass and I heard Leann suck him off which is the first time I have ever seen her suck something off after being in my ass. He called her a good little girl and told her to finish me off.

Leann easily fisted me after Daddy's cock fucking me and made me beg for permission to cum. She dragged it out torturing me since I had already cum once without permission that night.

After I came, Leann plugged me back up and we went home. I cant wait for Daddy to come over again.