I was never really into authoritarian or discipline type encounters, but I would like to tell you about an encounter I had a while ago. I like to go to adult video stores around town to check out the videos and to check out possible guy action. My favorite videos are the shemale, transexual or transvestite ones. I have fantasized for a long time, as I am sure a lot of guys have, about getting it on with a hot shemale. But, as far as I know, I have never actually even seen a shemale in person, let alone got it on with one. I have seen transvestites a couple of times in video stores and gay bars, but they are usually with someone so it is not easy to try to pick them up.
One night after stopping at a bar and having several drinks, I went to one of my usual video stores to see if there was anything going on. There were a few guys hanging around in the aisles but none that seemed interested. So I moved to the area where the shemale magazines are. After looking at the shemale and gay books and magazines for a few minutes I decided to move to the video section. As I left the book section and was walking to the shemale and gay video section I thought I noticed a guy checking me out. There was another guy not far away, but he didn't seem to be paying attention. I walked back and looked over the videos for a while and when I looked up I was sure that I saw the same guy watching me from the next aisle. I also thought that I saw the other guy looking at me but he was farther away and he looked away when I looked at him. I thought that I would move into the back area and look at the DVD's and see if either one of them followed.
I walked into the other area and again went to the shemale and gay section. After looking at the DVD's for a couple of minutes, I looked over and saw that the first guy had followed me into this area. This is a more secluded area and we were the only ones in it. This time he did not turn away when I looked back at him. Instead he slide his hand over and started to rub and squeeze his cock through his pants, so I did the same. He nodded his head, smiled and motioned toward the door. I smiled and nodded ok. He started to walk away, so I waited a minute and followed him. As I was walking out I noticed that the second guy was watching me. He smiled at me and I smiled back, but I kept walking.
I followed at a distance as the first guy went outside. He was waiting for me around the corner of the building. He was an average looking guy about 6' tall,190 lb., with a decent build and maybe in his early thirties. He asked me how I was doing and I said ok. Then he said "So what's going on" and I said "not much". He said he knew what I meant, there wasn't much going on tonight. He asked me what I was looking for and I told him that I was looking for some fun. When he asked what kind of fun, I said I liked all kinds of things since I am pretty versatile. He smiled and said that was good, and maybe we could go somewhere and have some fun. When I asked if he had some where to go, he said that he had a place not far from there. So I said ok. I followed his car for a few miles and he turned up a side street into a development. He pulled into the garage of a condo and I pulled up behind him. He told me his name was Ray and he said to come on in. I followed him through the garage and into the kitchen. I could see that it was a real nice place as he lead me into the living room and told me to sit on the couch.
He turned on a video and went to get us some drinks. It turned out that it was a shemale video. When he came back with the drinks he said he thought that I might like this video, and I told him it was my favorite. He smiled and said that he had hoped so. We watched the video and drank our drinks for a few minutes. While we watched the video he reached into his pocket and pulled out a small bottle of poppers. After he had taken a couple of sniffs he held the bottle up to my nose and had me take a few whiffs in each nostril. Then he put the bottle down and started to rub himself through his pants again, so I did the same. He reached over and started to rub me with one hand and pulled my hand over to him with the other. After a couple of minutes of this he started to unbutton and unzip my pants, so I did the same to his. He was not wearing any underwear so his hard dick popped right out. It was about 8" long and nice and thick. He asked me to stand up so he could make me more comfortable. Then he slid my pants and underwear down to my ankles. While I took my shirt off, he had me lift my feet so he could remove my pants, underwear, shoes and socks. As I stood naked before him, he started to slide his hands up and rub my legs.
I told him that I hated to interrupt this but I really needed to pee. He said sure he would show me where the bathroom was. As he stood up he removed his pants and shoes and took off his shirt. As the two of us walked naked to the bathroom, he smiled and said he was sure glad that I was into shemales. He showed me the bathroom and as I walked in he closed the door. As I started to pee I thought that I heard something, so I turned my head to look. He had left the door open slightly and I could see his reflection in the mirror. He was standing outside of the door watching me pee through the mirror, and stroking himself. About the time I was finishing, he pushed the door open and walked in. He stepped up behind me and as he pressed his hard cock against my ass crack he reached around me and said let me give you a hand shaking those last drops out. He started to stroke my dick as he slowly rubbed his cock up and down my ass crack. About this time I thought that I heard something else in the hall.
I turned my head and looked, there standing naked in the doorway was the second guy from the video store. He was in his late twenties, about 6'2", 195 lb. and solidly built. As he walked in stroking his hard 7" dick, he said it looks like we made a good choice. I pulled away from Ray and said "What do you mean, what is going on?". Ray said that they like going places and picking up a guy to bring home and have sex with, but sometimes the guys aren't into what they like. Since I seemed to be into shemales so much, and since one of their fantasies is to both make it with a shemale at the same time, I was going to be their shemale for the night. I said that I wasn't sure I was into this and at six feet tall, 180 lbs. I would probably not make a good one. I started to try to leave, but the other guy grabbed me and held me. Ray started smacking me and when I turned to get away he held me tighter while Ray started spanking my ass. When both cheeks were good and crimson they pushed me down on the floor. The new guy, who Ray called Bob, said that assuming that I could manage to get passed them both, which would not be easy, I would look pretty funny walking home naked since he had hid my clothes and car keys. He said that I had better do want they wanted or I would be sorry. He also said that if I went along with their fantasy we could all enjoy it, but if I didn't they would make it very unpleasant.
Bob said to sit on the floor while they got everything ready. Ray left the bathroom and quickly came back smoking a joint. He gave it to me and said that it would help me relax and enjoy it more. Bob was putting stuff out of the bathroom closet on to the counter. Ray left the room again and came back with a gym bag and some more drinks. He handed us both a drink and reached into the bag. He brought out a bottle of poppers and came over and had me take a few whiffs. By the time I was almost finished with the joint and the drink I was feeling pretty good. Bob had me stand up between he and Ray. They both reached into the stuff that Bob had placed on the vanity and came over with an electric razor, a safety razor and shaving cream. As I stood there Bob used the electric razor on my leg and Ray came right behind him with the shaving cream and razor. When they had finished shaving one leg they moved to the other, then my chest and underarms. Next they had me spread my legs and shaved between my legs and all around my cock and balls. Finally they bent me over, shaved my ass clean and wiped me off all over with a damp cloth. Then they sprayed perfume on my ass. Now I really did feel naked. Next they had me sit down again and they applied makeup to my face and red lipstick to my lips. When they were satisfied with this Ray brought the gym bag over. They took a blond wig out of the bag and put it on me. Then they had me stand up again and dressed me in a black garter belt, a pair of black hose and a pair of fake boobs that fasten in the back like a strapless bra. Next came pink thong like panties, black high heeled shoes and a waist length pink silk nighty. When they were done they stood back and admired their work. They had me walk and turn like I was modeling for them, and when I saw my reflection in the mirror I really was surprised. I was no super model but I probably looked good enough for what they had in mind.
Bob told me to follow him and we all went back into the living room. Bob and Ray sat on the couch and told me to get another shemale video from the shelf and put it into the machine. As I bent over to pick one out they both started making comments about how good my hairless ass looked. When I turned around they were sitting there, both still naked, and stroking each others cocks. After I had started the video, Bob told me to go in the kitchen and bring them a couple of drinks. When I came back into the room Bob was smoking a joint while Ray was turning on a video camera that he had placed on top of the TV and aimed at the couch. Ray sat back down on the couch so that the video would film me as I served them their drinks. After handing them their drinks they had me sit on the couch between them. They ran their hands up and down my legs, over my ass and under my nighty to play with my "tits", but they were careful not to touch my cock. As they continued to feel me up in front of the camera they took turns feeding me their drinks, having me smoke some of their joint and gave me a few good whiffs of poppers.
At this point my head was really spinning. They each took one of my hands and pulled it back to their dicks. As they laid back and finished their drinks I continued to play with their cocks and balls. When they had finished their drinks Bob pushed me onto the floor in front of them. He reached over and pulled my head down to his cock. I licked up and down the length of his dick and then licked and sucked on his balls. Ray got up and moved the camera to a table at the end of the couch so it could catch the action from the front. Then he sat back down and reached over and pulled my head to his cock. I was really getting turned on so I started to repeat what I had done to Bob. Working my way down that big cock. I licked up and down it's length several times and then started to lick and suck his balls. After a couple of minutes of working on his balls, I licked my way back up to the head of his cock. I slowly sucked down as much of it as I could and he started to moan. They had me alternate between them, sucking and licking their cocks and balls. Then Bob stood up with me kneeling in front of him. As I knelt there he pushed my face to his cock again so I started to suck and lick his cock and balls. He reached over and got the camera and told me to look up, this was a close up. Then Ray stood up so I could suck his cock while Bob filmed it. Ray started to move his hips and fuck my face.
After a few minutes Bob suggested we move to the bedroom so we could be more comfortable. As I followed Ray up the stairs to the bedroom Bob was filming us from behind and telling Ray about the great ass shots he was getting. When we got to the bedroom he placed the camera on the dresser beside the bed and left it running. Bob laid down on the bed next to Ray and spread his legs and told me to crawl up and start sucking him. I crawled up between his legs and licked my way up from his balls to the head of his dick. He held my head and pushed his dick into my mouth. After a few minutes of sucking Bob, Ray pulled me over to his cock which I greedily started to suck on. After a few minutes Bob pulled me back over to him. I reached down and started to stroke his big cock. I leaned forward and started to lick and kiss his nipples. I licked and sucked on both of his nipples then worked my way down his stomach. I licked up and down the length of his dick and around the big head. He pulled his legs up to his chest and told me to lick his asshole. As I was doing this Ray got up and moved behind me.
As I bent over on my elbows and knees between Bob's legs, Ray knelt on the bed behind me and ran his hands up and down my legs When he reached my ass he pushed my nighty up and started to rub and squeeze my ass cheeks. Then he leaned forward and started to lick and kiss all over my ass. He spread my legs apart and then spread my cheeks and pulled the thong out of my crack. He started to lick up and down my crack and then to lick and suck my asshole. It felt wonderful. After a while he started to alternate between tongue fucking my hole and slowly pushing first one, then another and finally three fingers up my asshole. He continued to lick and kiss my ass as he finger fucked my asshole. He took his fingers out of my ass and moved up and slowly started to push his cock in. Since I had not been fucked in a while, it hurt some as he pushed the head of his big dick in but soon it started to feel better. As Ray started to fuck me faster, I started to enjoy it and was really going to town licking and sucking Bob's cock, balls and asshole. I started pushing back on the dick in my ass. After about five or ten minutes Ray started to shudder and shoot his load up my ass. He kept his dick moving in my ass until it started to soften and popped out. As Ray got off the bed and got the video camera, Bob got up and moved behind me.
He started to push his dick into my asshole as Ray zoomed in for a closeup. As I started to move my ass with Bob's fucking motion, he looked at Ray and said "Yeah SHE is really getting into having her shemale pussy fucked now". It didn't take long until Bob was shooting his cum up my ass to join with Ray's. As he pulled his dick out Ray zoomed in for a close up of the cum running out of my hole. He even had Bob spread my cheeks so that my hole opened more and he could film the cum in my hole. While Ray had me pose on the bed so he could film me from different angles, Bob left the room. When he returned he was smoking a joint and carrying two drinks and the gym bag. Ray turned off the camera and took his drink. Bob told me to get up. He reached into the bag and handed me some tissues, a black wig, black thong panties, black nighty and some makeup from the bag. He told me to wipe the cum off of my ass, change into the black wig and the clothes and freshen up my makeup. While I stood in front of the bedroom mirror dressing and doing my makeup and hair, they sat on the bed watching me and drinking, smoking and stroking each others cocks.
When I was done they turned on the camera and filmed me modeling the clothes for them. Then Ray put the camera back on the dresser and they had me crawl over to them on my hands and knees. They stood there and had me kneel in front of them and suck them until they started to get hard again. While I sucked on Bob's balls, Ray turned around and bent over the bed. He had me kneel behind him and lick and tongue his asshole. While I was licking Ray's ass, Bob laid on the bed. He called me over so I crawled up on the bed between his legs and started to slowly lick all around the head of his dick. Then I licked down his dick to his big balls and sucked on them for a while, and finally I slowly licked back up his dick and sucked it into my mouth. While I was working on Bob's cock, Ray had been behind me licking my asshole. After a couple of minutes he reached into the bag and pulled out what must have been a 10" black dildo. He slowly rubbed the black cock around my asshole and then began to push it up my ass. As I continued to suck on Bob's cock, Ray began to slowly fuck me with the dildo. He would pull it almost all the way out and then slowly push it in until I could feel the fake balls touching my ass. After a few minutes Bob said that since I was nice and loose now he wanted me to move up and ride his dick. Ray pulled the dildo out of my ass and I moved up until I was kneeling with my hole over Bob's hard cock. Before I could even start to sit on his dick, he reached up, grabbed my hips and jerked up and buried his dick to the balls up my hole. As he started to fuck me he reached up and pulled me down onto him and started kissing and tongue fucking my mouth.
Ray climbed up on the bed and stood above Bob. When Bob let me go and I looked up Ray's dick was in my face. I opened my mouth and he started to fuck my face. After a few minutes Ray said he wanted some more of my shemale pussy. Bob pushed me off of his dick and got off of the bed without cumming. Ray told me to lay down on my back with my legs up. He got on the bed between my legs and pushed them up to my fake tits. He pushed his cock up my ass and started to fuck me deeply. Even though my asshole was getting sore, it felt so good that I started to moan and wiggle my ass. Bob stood next to us stroking his dick and telling Ray to pound that pussy. After Ray had fucked me for about ten minutes he turned to Bob and said he was going to need some help before he could shoot again. He stopped moving but kept his hard dick up my ass. Bob climbed up on the bed behind him and pushed his dick up Ray's ass. Now it was Ray's turn to moan. Ray started to fuck me again slowly until Bob got into sink fucking his ass. Once they got going, they were fucking so hard that you could hear the slap as Ray slammed into my ass and another as Bob slammed into his. After what seemed like twenty minutes of Ray fucking me like this he started to cum in my ass pussy again. That was all it took to set me off and I shot my load into my thong panties. As Ray started to shoot in my ass, his hole must have started squeezing Bob's cock harder and Bob moaned pulled his cock out of Ray's ass and shot all over Ray's back. Then they both collapsed into a pile on top of me with Ray's dick still in my ass and Bob's dick in Ray's asshole.
After a few minutes we all started to get up. My legs were weak and shaky so they helped me stand up and walk to the bathroom. They helped me get out of my shemale clothes and makeup and wipe the cum off of my ass and Ray's back. They asked me to spend the night so we could do it again in the morning, but I told them I really had to leave. After they gave me my clothes and car keys, I got dressed and started to leave. Bob gave me their number so I could call them and we could do it again sometime. I just called them since I need another shave to get rid of all of this itchy stubble. They said that instead of the dildo they are inviting a friend who has a real 10" black dick and says that he can't wait to try some of that shemale ass pussy he saw my video. I may have to stay the night this time!