Best Fuck of My Life
Best Fuck of My Life
This is a 100% true story of the best fuck of my life. It happened almost in 2016. I had gotten back into dressing after a very long time. I work very hard at being as passable as possible and it really seemed to work on this particular night. Here's the story.
I got all dolled up in one of my new dresses and headed up to VIP Nightclub north of here. It had been a great night for me getting a lot of attention from both men and girls. One super cute Asian girl even came up to me and said I reminded her of Jennifer Aniston. I smiled and said, "well, maybe her mother". Time flew by and it was last call when he made his move on me. His name was Bryan and he looked to be at least 15 years younger than me. That's right baby...it was a cougar moment for Jennifer. He asked me if I was with anybody tonight and I told him no. He said I looked really hot and he would like to fuck me all night long. OMG, I almost came in my panties right there. Trying to keep calm I said "oh really?" He said "baby, I know you are older than me and some of the other girls are pissed that I am talking to you, but you just look so fuckable." Who could turn down a line like that.
Then he said "The only problem is we can't do it at my place.” I said you can follow me home. I couldn't believe what I was saying. I was inviting a man I had just met to follow me home and fuck my brains out. I think he saw the nervousness in my face. He took my head in his hands and planted a hot, juicy kiss on my lips, forcing my mouth open and thrusting his tongue almost down my throat. After breaking off the kiss I said let's go. We walked out to the parking lot and when we got to my car, he spun me around and started kissing me hard and deep. I just love to be kissed and this guy really new how to kiss a slut like me. He had both hands on my ass pulling up my dress. He gave my ass a quick grab and then breaking off the kiss, he went over to get his car. I was so fucking horny that when a black guy sitting in the car next to mine said lean in and give me some head, I didn't hesitate. I felt like such a slut. Short dress, high heels, bending over and leaning into a car to suck a big black cock while waiting for the man that was going to take me home and fuck me silly.
As Bryan pulled up, I pulled myself away from the black guys cock, got in my car and we headed home. Now the fun was going to start. Once in my house, we went into the kitchen where I fixed us both a drink. He started kissing me again and then put his hands on my shoulders to push me down to my knees. I rubbed his cock thru his jeans and boy was I surprised. For a medium sized guy, he had a monster piece of meat in his pants. He pulled his cock out and my eyes just about popped out of my head. I was looking at, at least nine inches of beautiful cock. He asked, "Do you like what you see?" I said "Oh yeah." "Then suck my cock you little faggot." I didn't need to be told twice. I opened up really wide and took that beautiful cock into my cock sucking mouth. God, did it feel and taste great. He put his hand behind my head and guided me back and forth on his dick. After getting his cock nice and wet, I took a big breath, opened wide and swallowed every inch. I thought he was going to explode right there. He said "What a great cocksucker." I looked up at him and said I just love your cock.
He lifted me up off my knees and placed another hot, wet, juicy kiss on me and then said let's go upstairs so I can fuck your hot little ass pussy. I held his hand and led him upstairs. Once in the bedroom he got really aggressive. He pushed me onto the bed, rolled me onto my back and climbed on top of me spreading my legs and kissing me like a madman. He was rubbing my clitty through my pantyhose making me hard and wet. Then he just grabbed the top of the pantyhose and pulled and ripped them right off me. At that moment I thought “I am going to be ****d" But then he crawled up and slid his cock between my hungry lips and started taking off the rest of his clothes. Once naked, he started really fucking my mouth and throat. He said use my spit to lube my pussy because he really wanted to start fucking me.
After fucking my mouth and shoving his cock all the way down my throat, he rolled over on his back with that beautiful 9 incher standing at attention. He said “what are you waiting for? Straddle me and get my dick inside your sissy faggot pussy”. I asked if he had a condom and he said fuck no. He said he only fucks sissy fags bareback. At this point, I knew there was no turning back. I wasn’t sure if I could take such a huge cock without anything for lube except my spit…but I was sure going to try. I straddled him cowgirl style and reached back to place the head of his super hard cock at the entrance to my fag asshole. Gawd, I was sooooo horny for that cock. It felt huge (probably because it was, lol). I eased it in until I could it feel it pop past the outer ring of my cunt. He put his hands on my hips and said get that fucking cock up your ass, NOW. I pushed down hard on his dick and felt every inch slide up into me. OMG!!! It felt so fucking good. He only let me take a few seconds to get used to that monster and then told me to start riding his cock like a good little sissy faggot. I started sliding up and down that wonderful fuck stick, feeling it hit way up in to my tummy every time I slid all the way down. After a minute or so, I really started bouncing up and down with my hot, wet sissy asshole. He was guiding me up and down with his hands on my hips. I started moaning and telling him to fuck me. .…fuck me deep. I love your cock. Please don’t stop fucking me. He said, “oh baby, we are just getting started.”
He reached up and pulled me down and started kissing me while fucking up into my ass pussy. I was going crazy! Getting fucked silly and being kissed hard and deep by my man with our arms wrapped around each other. He was calling me all kinds of names. Fucking faggot, shemale whore, fucking slut. I loved every word and every thrust. Then he did something that took me by surprise. He broke off the kiss and told me to suck his cock so I could taste my ass pussy. I pushed myself up and off his glorious cock and slid down and slid it right into my cock sucking mouth. I loved the taste and smell of cock and ass juice mixed together. I was on my hands and knees on the bed with my head bobbing up and down on his huge cock. He put his hands on my head and shoved his dick all the way down my throat until I gagged. He held me there, thrusting up into my face until I thought I was going to pass out. Spit was flowing out of the corners of my faggot mouth. Finally, he pulled my mouth off his dick and pulled me up to start kissing me long and deep. Gawd, I was loving this! This time I broke off the kiss and told him I wanted him on top of me between my legs (my all time fav position). I rolled over onto my back and spread my legs. He got between my out stretched legs and slid his big beautiful cock all the way up my ass pussy. I wrapped my arms and legs around him and begged him to fuck me. He said ”you are one horny fucking slut”. He was pounding me hard and fast. I was moaning so loud I thought I might wake the neighbors. I didn’t care. I just kept saying over and over, I love your cock, fuck me, fuck me. He leaned in and while still fucking me silly, started kissing me. This just about made me come. I dug my fingernails into his back and pushed my ass pussy up to meet his powerful thrusts. This guy really knew how to fuck a sissy, crossdressing faggot like me. This was absolutely, the best fuck of my life. He said he was going to fuck me so long and hard that I wouldn’t be able to walk for a week. Then he pulled out and straddled my face and said open your fucking mouth you cock sucking bitch!
I opened my mouth and he shoved his cock all the way down my throat. He fucked my face all the while calling me a faggot, queer, slut. I wanted him to cum in my mouth so bad, but I didn’t want the night to end. He asked me how my ass tasted and I told him I loved it. He said keep sucking my cock you fucking whore! I sucked and licked his cock for all I was worth. Then he pulled his cock away and told me to get on my hands and knees. He said I am going to fuck you like the bitch in heat you are. He told me to reach back and open my hole for him. I grabbed my ass cheeks and spread my ass wide open for him. He put his cock right at the entrance and asked are you ready you little faggot? I said God yes. He grabbed my hips and rammed all nine inches as hard as he could up my ass. I swear I thought his cock was going to come out of my mouth. He started fucking me so fucking hard, I was almost in tears. He said take that cock bitch. He started slapping my ass really hard. Slap, slap, slap. Over and over. He said fuck yourself on my cock. I started pushing back into him fast and hard. He said “You’re going to let me fuck you whenever I want aren’t you?” I said “yes.” I want you to fuck me every fucking day. He pushed me flat on the bed and fucked me like he was trying shove his dick right through me and the mattress. I had never been fucked so hard in my life. I looked at the clock by my bed and realized we had been fucking for over an hour and he was still going strong. I was falling in love with this guy and his monster cock. I kept saying Oh Bryan, fuck me, fuck me hard, fuck me deep. I love it. I love your cock. He thrust really hard a few more times and just lay flat on my back with his cock up my ass. He didn’t move. I asked if he was ok. He said, just resting baby. After a couple minutes he slid his cock out of me. He went and got a drink of water. He told me to get off the bed and stand facing the wall by my closet. He came up behind me and said I am not done fucking you.
With that he slid his cock right back up my hole. Oh my god did that feel great. He started fucking me against the wall. Kissing the back of my neck he said you know I’m going to breed that ass of yours tonight. I said I can’t believe you haven’t cum. He started fucking me so hard that he was literally lifting me off the floor with every thrust. Fuck me, fuck me!!! I kept saying over and over. He said get on your knees and suck my cock. Taste your ass you little slut. I got down on my knees and looked up at him with my mouth wide open and my tongue sticking out. He slapped my face and tongue again and again with his cock. He grabbed my head in both hands and started face fucking me again. He said you are an amazing piece of ass. And then he said “get your ass up and bend over the side of the bed.”
I got up and went over to the side of my bed and he said now I’m got to fuck you till I shoot a huge load of cum up your ass. You ready for that bitch? I said God yes. He pushed me forward so that my upper body was on the bed but my legs were on the floor. He kicked my legs apart and rammed his cock into me. He put his hands on my throat and started choking me and fucking me at the same time. I squeaked out the words, Fuck me Bryan, fuck me. He then grabbed me by the shoulders and fucked me so deep I could feel his cum filled balls slapping against mine with each stroke. His thrusts got faster and shorter and then he let out a loud grunt and scream as his cock exploded inside of me. He came so much, I could feel it running out of my ass and down my legs. He must have shot at least six times. I felt like a complete woman. He kept his hard cock in my ass as I kept clenching my ass cheeks trying to milk every last drop of cum out of him. Finally, he told me to get on my knees and clean him up. He pulled out of me and I got down on my knees and took his softening cock into my cock sucking mouth. It tasted soooo good! A mixture of ass juice and cum. He told me to look up at him. As I did he said that was a great fuck. I told him he had just given me the best fuck of my life.
When he left, he told me wanted to make me his personal little fuck doll. Well…..that never happened. I saw him a couple weeks later at the same night club and he completely blew me off. Oh well, his loss. I’ve been fucked many more times since then. Those stories to come.
This is a 100% true story of the best fuck of my life. It happened almost in 2016. I had gotten back into dressing after a very long time. I work very hard at being as passable as possible and it really seemed to work on this particular night. Here's the story.
I got all dolled up in one of my new dresses and headed up to VIP Nightclub north of here. It had been a great night for me getting a lot of attention from both men and girls. One super cute Asian girl even came up to me and said I reminded her of Jennifer Aniston. I smiled and said, "well, maybe her mother". Time flew by and it was last call when he made his move on me. His name was Bryan and he looked to be at least 15 years younger than me. That's right baby...it was a cougar moment for Jennifer. He asked me if I was with anybody tonight and I told him no. He said I looked really hot and he would like to fuck me all night long. OMG, I almost came in my panties right there. Trying to keep calm I said "oh really?" He said "baby, I know you are older than me and some of the other girls are pissed that I am talking to you, but you just look so fuckable." Who could turn down a line like that.
Then he said "The only problem is we can't do it at my place.” I said you can follow me home. I couldn't believe what I was saying. I was inviting a man I had just met to follow me home and fuck my brains out. I think he saw the nervousness in my face. He took my head in his hands and planted a hot, juicy kiss on my lips, forcing my mouth open and thrusting his tongue almost down my throat. After breaking off the kiss I said let's go. We walked out to the parking lot and when we got to my car, he spun me around and started kissing me hard and deep. I just love to be kissed and this guy really new how to kiss a slut like me. He had both hands on my ass pulling up my dress. He gave my ass a quick grab and then breaking off the kiss, he went over to get his car. I was so fucking horny that when a black guy sitting in the car next to mine said lean in and give me some head, I didn't hesitate. I felt like such a slut. Short dress, high heels, bending over and leaning into a car to suck a big black cock while waiting for the man that was going to take me home and fuck me silly.
As Bryan pulled up, I pulled myself away from the black guys cock, got in my car and we headed home. Now the fun was going to start. Once in my house, we went into the kitchen where I fixed us both a drink. He started kissing me again and then put his hands on my shoulders to push me down to my knees. I rubbed his cock thru his jeans and boy was I surprised. For a medium sized guy, he had a monster piece of meat in his pants. He pulled his cock out and my eyes just about popped out of my head. I was looking at, at least nine inches of beautiful cock. He asked, "Do you like what you see?" I said "Oh yeah." "Then suck my cock you little faggot." I didn't need to be told twice. I opened up really wide and took that beautiful cock into my cock sucking mouth. God, did it feel and taste great. He put his hand behind my head and guided me back and forth on his dick. After getting his cock nice and wet, I took a big breath, opened wide and swallowed every inch. I thought he was going to explode right there. He said "What a great cocksucker." I looked up at him and said I just love your cock.
He lifted me up off my knees and placed another hot, wet, juicy kiss on me and then said let's go upstairs so I can fuck your hot little ass pussy. I held his hand and led him upstairs. Once in the bedroom he got really aggressive. He pushed me onto the bed, rolled me onto my back and climbed on top of me spreading my legs and kissing me like a madman. He was rubbing my clitty through my pantyhose making me hard and wet. Then he just grabbed the top of the pantyhose and pulled and ripped them right off me. At that moment I thought “I am going to be ****d" But then he crawled up and slid his cock between my hungry lips and started taking off the rest of his clothes. Once naked, he started really fucking my mouth and throat. He said use my spit to lube my pussy because he really wanted to start fucking me.
After fucking my mouth and shoving his cock all the way down my throat, he rolled over on his back with that beautiful 9 incher standing at attention. He said “what are you waiting for? Straddle me and get my dick inside your sissy faggot pussy”. I asked if he had a condom and he said fuck no. He said he only fucks sissy fags bareback. At this point, I knew there was no turning back. I wasn’t sure if I could take such a huge cock without anything for lube except my spit…but I was sure going to try. I straddled him cowgirl style and reached back to place the head of his super hard cock at the entrance to my fag asshole. Gawd, I was sooooo horny for that cock. It felt huge (probably because it was, lol). I eased it in until I could it feel it pop past the outer ring of my cunt. He put his hands on my hips and said get that fucking cock up your ass, NOW. I pushed down hard on his dick and felt every inch slide up into me. OMG!!! It felt so fucking good. He only let me take a few seconds to get used to that monster and then told me to start riding his cock like a good little sissy faggot. I started sliding up and down that wonderful fuck stick, feeling it hit way up in to my tummy every time I slid all the way down. After a minute or so, I really started bouncing up and down with my hot, wet sissy asshole. He was guiding me up and down with his hands on my hips. I started moaning and telling him to fuck me. .…fuck me deep. I love your cock. Please don’t stop fucking me. He said, “oh baby, we are just getting started.”
He reached up and pulled me down and started kissing me while fucking up into my ass pussy. I was going crazy! Getting fucked silly and being kissed hard and deep by my man with our arms wrapped around each other. He was calling me all kinds of names. Fucking faggot, shemale whore, fucking slut. I loved every word and every thrust. Then he did something that took me by surprise. He broke off the kiss and told me to suck his cock so I could taste my ass pussy. I pushed myself up and off his glorious cock and slid down and slid it right into my cock sucking mouth. I loved the taste and smell of cock and ass juice mixed together. I was on my hands and knees on the bed with my head bobbing up and down on his huge cock. He put his hands on my head and shoved his dick all the way down my throat until I gagged. He held me there, thrusting up into my face until I thought I was going to pass out. Spit was flowing out of the corners of my faggot mouth. Finally, he pulled my mouth off his dick and pulled me up to start kissing me long and deep. Gawd, I was loving this! This time I broke off the kiss and told him I wanted him on top of me between my legs (my all time fav position). I rolled over onto my back and spread my legs. He got between my out stretched legs and slid his big beautiful cock all the way up my ass pussy. I wrapped my arms and legs around him and begged him to fuck me. He said ”you are one horny fucking slut”. He was pounding me hard and fast. I was moaning so loud I thought I might wake the neighbors. I didn’t care. I just kept saying over and over, I love your cock, fuck me, fuck me. He leaned in and while still fucking me silly, started kissing me. This just about made me come. I dug my fingernails into his back and pushed my ass pussy up to meet his powerful thrusts. This guy really knew how to fuck a sissy, crossdressing faggot like me. This was absolutely, the best fuck of my life. He said he was going to fuck me so long and hard that I wouldn’t be able to walk for a week. Then he pulled out and straddled my face and said open your fucking mouth you cock sucking bitch!
I opened my mouth and he shoved his cock all the way down my throat. He fucked my face all the while calling me a faggot, queer, slut. I wanted him to cum in my mouth so bad, but I didn’t want the night to end. He asked me how my ass tasted and I told him I loved it. He said keep sucking my cock you fucking whore! I sucked and licked his cock for all I was worth. Then he pulled his cock away and told me to get on my hands and knees. He said I am going to fuck you like the bitch in heat you are. He told me to reach back and open my hole for him. I grabbed my ass cheeks and spread my ass wide open for him. He put his cock right at the entrance and asked are you ready you little faggot? I said God yes. He grabbed my hips and rammed all nine inches as hard as he could up my ass. I swear I thought his cock was going to come out of my mouth. He started fucking me so fucking hard, I was almost in tears. He said take that cock bitch. He started slapping my ass really hard. Slap, slap, slap. Over and over. He said fuck yourself on my cock. I started pushing back into him fast and hard. He said “You’re going to let me fuck you whenever I want aren’t you?” I said “yes.” I want you to fuck me every fucking day. He pushed me flat on the bed and fucked me like he was trying shove his dick right through me and the mattress. I had never been fucked so hard in my life. I looked at the clock by my bed and realized we had been fucking for over an hour and he was still going strong. I was falling in love with this guy and his monster cock. I kept saying Oh Bryan, fuck me, fuck me hard, fuck me deep. I love it. I love your cock. He thrust really hard a few more times and just lay flat on my back with his cock up my ass. He didn’t move. I asked if he was ok. He said, just resting baby. After a couple minutes he slid his cock out of me. He went and got a drink of water. He told me to get off the bed and stand facing the wall by my closet. He came up behind me and said I am not done fucking you.
With that he slid his cock right back up my hole. Oh my god did that feel great. He started fucking me against the wall. Kissing the back of my neck he said you know I’m going to breed that ass of yours tonight. I said I can’t believe you haven’t cum. He started fucking me so hard that he was literally lifting me off the floor with every thrust. Fuck me, fuck me!!! I kept saying over and over. He said get on your knees and suck my cock. Taste your ass you little slut. I got down on my knees and looked up at him with my mouth wide open and my tongue sticking out. He slapped my face and tongue again and again with his cock. He grabbed my head in both hands and started face fucking me again. He said you are an amazing piece of ass. And then he said “get your ass up and bend over the side of the bed.”
I got up and went over to the side of my bed and he said now I’m got to fuck you till I shoot a huge load of cum up your ass. You ready for that bitch? I said God yes. He pushed me forward so that my upper body was on the bed but my legs were on the floor. He kicked my legs apart and rammed his cock into me. He put his hands on my throat and started choking me and fucking me at the same time. I squeaked out the words, Fuck me Bryan, fuck me. He then grabbed me by the shoulders and fucked me so deep I could feel his cum filled balls slapping against mine with each stroke. His thrusts got faster and shorter and then he let out a loud grunt and scream as his cock exploded inside of me. He came so much, I could feel it running out of my ass and down my legs. He must have shot at least six times. I felt like a complete woman. He kept his hard cock in my ass as I kept clenching my ass cheeks trying to milk every last drop of cum out of him. Finally, he told me to get on my knees and clean him up. He pulled out of me and I got down on my knees and took his softening cock into my cock sucking mouth. It tasted soooo good! A mixture of ass juice and cum. He told me to look up at him. As I did he said that was a great fuck. I told him he had just given me the best fuck of my life.
When he left, he told me wanted to make me his personal little fuck doll. Well…..that never happened. I saw him a couple weeks later at the same night club and he completely blew me off. Oh well, his loss. I’ve been fucked many more times since then. Those stories to come.
2 years ago
