Later tonight I have a woman coming over to my place. I met her on craigslist. We've been texting over the last week about everything we want to do to each other and tonight's the first night for us to finally get together. I'm 29, white, tall and athletic, and she's 38, white, short and a bit thick with huge tits. And I have a 22 y/o tiny hot asian girlfriend already, but she doesn't know how kinky I can be.

This is how it all began. I started watching interracial porn years ago, then eventually cuckold porn before about a year ago going on to sissy/tranny porn. Soon I started watching the "hypno" videos and started getting really turned on by them. After a while of watching them I went and got a little beginner buttplug and started using it myself. That wasn't enough and eventually I was looking for guys on craigslist to hookup with. I was always telling my girlfriends how to suck my cock, so I wondered if I was any good at it. I found a guy and he said he loved the oral then fucked me pretty good ... after that I was looking for a guy online about once every few months. I had sex with my girlfriend all the time but also liked getting fucked. Meeting online took too much time and eventually I went and got a bigger and better dildo to use myself.

I've had the dildo now for about 6 months and can use it pretty well learning how to cum on it from prostate stimulation. So I don't have any physical attraction to guys, don't like to kiss or anything else intimate, but my fantasy of a bisexual MFM 3sum with a down woman has grown. In hopes of finding a woman I made a post on craigslist. That post was much longer than this is but it basically said how much I liked both sex with woman and getting fucked, but not the actual intimate gay sex stuff.

This lady replied to me about how much she's been getting off on gay porn lately. We started emailing, then texting. It was all sorts of dirty stuff about what we liked. And now she's coming over tonight for hours of fun and sex. What she's really excited and looking forward to is getting to rim me and play with my cock at the same time. Then she wants me on my hands and knees while we 69 so she can also fuck me with my dildo while sucking me and I'm eating her out. HOT! I told her she'd probably make me cum so quickly like that and that I'll even cum twice. Then she really wants to get fucked in the ass too.

Best part is I'm setting up my camera hidden away to record the first part of however much it can get tonight. And if tonight goes well, she wants to consider watching me get fucked and have a 3sum. Then, she's also mentioning she likes women in bed, so maybe someday we'll have a MFF 3sum. She gets very turned on by the idea of 3 people all into each other and what we can do.

Last, a warning: Don't watch those sissy hypno trainers unless you really want to do that! I'm tall, masculine, hung, never left a woman unhappy in bed, but now I also shave my ass to get fucked.

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!”

When I was 18 I ventured to the seedy section of Boston called the Combat Zone. I heard all the sordid stories of prostitutes and strippers as well as the crime and how rough it was. I was curious to what really went on down there so one night I skipped out on my friends and headed into Boston to check it out. I was 5'11 long blonde hair and weighed 135lbs. I had on jeans and a t-shirt and definitely peeked the interest of a few men as I walked down the street. I was new to sex with girls and had never had sex with a guy. I knew I wasn't gay or anything like that. I walked by a few strip bars and some adult book stores and came to one that looked interesting. I didn't see anyone in the store so I went in.

As I walked in I was stopped at the counter by the clerk who asked me for my ID. I gave him my drivers license and he laughed and said sure kid have fun. I was very young looking. I was 18 but I looked closer to 14 or 15. I walked up and down the aisles looking at the huge collection of porn magazines and sex toys. When I came to the back of the store I saw another section called Peep Booths. I asked the guy who was sitting at the desk what it was. He asked if I had ever been to a peep show before. I told him no I hadn't he said well its a bunch of booths inside where a person can go and watch some porn videos. I asked how much it was and he said $3 minimum. I gave him a $5 dollar bill and he gave me my tokens. He said go inside and find a booth and enjoy. I took my tokens and walked inside. It was so dark I could hardly see my own hand in front of me. As I walked along I felt hands grabbing my cock and ass. I kept moving not stopping. I walked up and down through this maze of booths and came to one that I thought I would try. I went inside and locked the door behind me and put a token in the machine and the video started playing. As the video played I could see in the booth and noticed a hole on one side of the booth. I looked down and saw a man in the other booth obviously jerking off. I sat up on the chair and watched my video. When the time expired I put another token in.
I then heard a knock on the door and a man said open the door please. I thought it was the man from upfront but when I unlocked the door a black guy pushed his way inside and told me to be quiet. I was very scared. He asked why I was there and I said I was just watching a video. He asked me if I sucked cock and I told him no I was straight. He laughed and said that doesn't mean anything. Lots of straight guys suck dick. I then noticed that he had his cock out. It was very big. Much bigger than my 5.5 inch cock. He told me to suck his cock. I told him I didn't want to. That's when he took out a bottle and said here sniff this it will make you feel better. I didn't know what they were. I asked and he said they were called poppers. I took a sniff and all of a sudden I felt so lightheaded like I was high. I had no control and I went to me knees. The guy then took my head and shoved his cock into my mouth. Suck it he said. I didn't know what to do my head was spinning. I began sucking his cock and I could taste his salty precum. He was holding my head shoving his black cock deep into my throat making me gag. First time my ass he said. You're a natural. I was starting to get my head straight when he stuck the bottle under my nose and told me to sniff it again. I did and it all started again. My head was spinning. I felt helpless and was doing what he told me to do. Then I heard him unlock the door. I saw out of the corner of my eye the door open and could see 2 or 3 guys standing there watching as I sucked my first cock. About 5 mins later I felt him pull my head closer and he shot his load into my mouth and told me to swallow it. I was choking and trying to swallow but it was too much. I spit some out and it landed on my shirt. He let go of my head and I sat there on the floor looking up. Then he got out and another guy got in. He took his cock out and told me to suck him. Feed him some poppers I heard a voice say and the bottle was placed at my nose for me to inhale. I knew what to do at this point and inhaled. Then opened my mouth to take this new guys cock. He was also black and very fat. I sucked his cock and he came rather quickly. Another guy came in and said he wanted my hole. I was pleading for him to not do it. But he pulled my pants down and spun me around and told me to bend over. I did and he again fed me some poppers. He said this will make it better and I felt his cock press against my virgin asshole. I wanted to scream but my head was still spinning and I felt him enter me. I couldn't believe all of this was happening to me. I felt his cock open my tight hole and slide in and out. His balls were slapping my balls as he thrust in and out. That's it baby take that dick. You like it don't you he said and I said no. Then another person held the poppers under my nose again. They were controlling me with these poppers. He fucked my ass and shot his load deep in me. When he pulled out I felt his cum run down my legs. He was then replaced by another and then another. In all I took 4 cocks up my ass and sucked off 4. They all left me there when they were done using me and I sat in the booth crying my eyes out. I was so ashamed and didn't want to leave. After about 30 mins I gathered myself up and walked out. Not making eye contact with anyone. When I got outside there were 3 or 4 guys standing outside and I walked past them. As I walked by they said good night sweet cheeks and all laughed. I felt like shit. I kept walking even when a prostitute asked me if I wanted a date. I kept that story to myself until just now. I now know this was my reason for becoming bi later in life.