My Best Friend's Uncle
My friend Matt was having a going away party. We had been best friends for years and he was one of the first people I talked to before really embracing my lifestyle. He was always so cool and defended me when bullies in school would tease me. I even offered to blow him once in college, but he said that just would be too weird and he is strictly for girls, but we stayed the best of friends. Many of the people at the party knew my lifestyle and some of my old friends actively made passes at me from time to time.
Matt told me to just be myself because I knew most of the people there, so I had a little black dress I had been dying to wear. Over time I had grown my hair down to my shoulders and dyed it purple with red highlights and I had some Skull Girl barrettes. The last parts were the pink Nikes and babydoll socks. I always stay shaved, all over and underneath, and my perfume was very light, and Matt said it made me smell girly, but he still wouldn’t let me at least blow him…. oh well, a gurl can dream. Once Matt picked me up, he asked “What are you all dressed up for?” “For your party silly” I shot back. I really wanted to give him a going away present, but the chances were next to zero, but I planned to try anyway, and I think he knew because I wore everything that he said, “fits me.”
The party was in the basement of Matt’s uncle, he had a nice home and Matt said he was a great guy, but that was his uncle. I heard so many stories about how back in the day about the gang he road with and some of his legendary fights, but Matt said since he has done his time, he has mellowed out, regardless I steered clear of him. The music was loud, I could hear it from the side of the house. We walked in headed downstairs and once Matt arrived there was a ton of “Congratulations!” and the party really started. From the start, as soon as we made it to the basement we were split up. Some of the girls there grabbed me by the head and dragged me away and Matt was Matt, always the life of the party. The girls always asked me the same questions about Matt, the one that bugged me the most was “Is he gay because he is always hanging out with you?” “No” he is not, blah, blah, blah.
A few of the guys were hitting on me and some of the other girls and Mikey (my former bully) was ALWAYS “accidently” bumping into me, and after a few drinks he was straight forward trying to feel me up. As the night when on, I felt a hands on my butt, that was fine but seeing Matt’s uncle leering at me gave me the creeps. I started to feel like my dress was too short, but I just continued on and enjoyed the party. Looking at my watch it was around 1am and I was looking for Matt to take me home. I had a few drinks, and I was tipsy but not drunk. I couldn’t find Matt anywhere, one of the girls said right before she left that Matt was hooking up with some skank that blew him in the bathroom. WTF?! When she left, I was the last girl at the party, no I was the last person at the party. I started looking for my purse to grab some money to get a cab. Shit, I left my purse at home! Seemingly on queue, Matt’s creepy biker uncle came around the corner. He had a plastic garbage cleaning up after everyone. My heart dropped. I asked for a ride home because I lived on the other side of town and had no money. He said he had to finish cleaning up and he will see what he could do if I helped him clean.
I notices him looking at my ass each time I bent over to pick up a red cup and other trash. “I know you remember me…Matt said you call yourself Kelly now right?” “Yes” I got out. “Look, there is no need for you to be scared of me, I know who you are and what you are. Let me finish cleaning up down here.” “Hey there is still beer and some Wild Turkey on the counter” he said trying to be nice. I took a few sips to just chill out as he cleaned. As he cleaned, we actually talked and shared some laughs, and finished off the remains of the Wild Turkey. The more we talked the more we sipped the secret stash of Crown Royal that was behind the counter. It was nearly an hour when Darin, Matt’s uncle’s real name, finished cleaning and sat down on the couch. He admitted he took a few more sips than he should have and due to his last DUI, driving was out the question, but he did offer me the pull out couch.
I think due to the alcohol we became freer as we talked. He made comments on how I made a pretty gurl, with my little chubby legs, cute outfit and how I smelled really nice. He next asked me if I used coco butter on my legs. The smell was familiar because that is what some of the sissies in prison used to try to be more feminine for their cell daddies. Then making an animated gesture he made a cool comeback, “…But you are out of this world gurl.” He laughed and I giggled, and he told me I had a cute laugh. I asked him about prison, and he told me all about his time there, and he had a couple of bitches that offered ass for protect, that’s the game. Replying back, I told him I could totally understand, because I would never survive. “Yeah…you right, because the guards and the inmates would be fucking you every night.”
I laid back on the couch and slipped off my pink-hearted “Saturday” panties. I did as he asked and laid back again while spreading my legs wide. It was like he was enchanted will my boi hole. “Fuck, fuck, fuck gurl…my God you are blessed!” “That is the prettiest asshole I have EVER seen!” Surprised, I asked “He said you had your…bitches?” “Yeah, but not this pretty.” Its was weird, I never had anyone complement my asshole. “And I love that you are shaved all over, shit you fine.” I was thinking I wanted this to be my present to Matt, but Matt only wanted real girls, but I was going to try my hardest for his last day in town. Now my gurly brain was really confused.
Darin moved so close; he was literally inches from my boi hole. Dropping his shorts, he whipped out the biggest, thickest dick I have ever seen in my life…Holy shit! “Wait wait wait, you said you just want to see it.” “I need to kiss it, I promise you will….” and before he finished what he was saying, a skilled tongue explored my sissy cunt. My little clitty was at full attention, OMG it felt so good. Yes, I have been licked back there before but never like this. I scooted down, grabbed the back of my knees and pulled my legs back as far as I could. I wanted to stroke myself but when I touched my clitty, Darin gave a “Don’t touch it!” He had a plan, and I honestly thought, he planned this all along; but I didn’t care I just wanted him to keep doing what he was doing. Closing my eyes, I gave a heavy moan and it felt like his tongue went deeper in my asshole. I didn’t know if I wanted to use my hands to keep pulling my legs back or to spread my ass cheeks wider. He knew what to do to me and I loved it.
It had to be a good 20-30 minutes when he removed his face from my bottom. When he stood up, he had a raging, veiny 10-11 inch hardon that he was pumping. The head of his dick was soooooo big, it looked like a big brown doorknob! “I think your ready baby” he said slyly. “Ready for what?!” “There is absolutely no way that thing will fit in me, no fucking way!” said in a high pitched tone. “That thing is huge, no…no way!!!” Darin smiled because he noticed during all of my protesting, I never got off the couch. His hands replaced my hands behind my knees. “No, you can’t…it’s too big…I’m not ready.” “I got something that will help” with that Darin strolled over to the side of the counter. I Just watched as his hard fat snake bounced as he walked. I didn’t move or try to run; I just laid there spread eagle on my back, in my little black dress and my panties on the rug. I was filled with the terror of his monster trying to enter my tiny little puckered hole and the OMG factor this really happening thoughts. My mind was trying to figure out why I was growing attracted to his old biker. Up until now I would never find myself in the company of people like him, but now, some weird attraction kept me on the couch spread like some girl in a video.
Darin came back with a can of cooking oil. “You are going to spray cooking oil on my asshole?!” I said in a questioning and surprised manner. “Trust me” he said so coolly. “Please don’t hurt me…okay…be gentle. I have never had anything like what’s between your legs come near me before.” I said while staring at the snake that was about to make me a biker bitch.
Shaking the can, he coated my butthole with the cooking oil spray, next was his cock. When he started rubbing oil on his cock, I could see all the veins and the head looked even bigger. I kept telling myself it too late to get the hell out of there, why didn’t leave when I had the chance? Darin got into mounting position, put his hands behind my knees again and slowly lowered himself. “Kelly…just try your best to relax…we are going to take this nice…and slow...okay” I nodded my head yes, letting him know I was completely trusting him. His cockhead kissed my rear door and I started breathing heavy. He looked directly in my eyes and said, “Look at me baby” Now, I was talking fast, “How can I just look at you when…when…do you know how big you are?!” “It’s going to hurt so bad” I was near distressed. When I had my virginity taken, it was rough, but I wanted to be fucked like a girl so much, I took it, but the guy that took me was half the size and thickness of on Darin. As I was rambling, I felt Darin’s cock start stretching out my sissy hole. More and more it opened like it was being pulled apart. In a wavering voice, I looked at him with eyes as big as saucers and gave an, “Ouchy…..ow…oh my God please stop…Darin…ooooooo…” For his part he never stopped his slow and steady pace. For my part, I clutched the couch cushions with a death grip. Inside my pink Nikes, my toes were locked in the spread position. It was an absolute struggle as he entered me, and he was only halfway in.
“Listen to me, don’t look at a dick, look at me baby.” “I can’t do this…it hurts” “It’s okay baby” Darin said softly as tears began to well in my eyes. “You are doing so good baby, let daddy guide you.” That’s when he got fully on top of me, his tatted up arms pinned my legs back and his cock drilled in until I felt his pelvis rest on my little belly. The pain of being impaled with his old biker’s baseball bat of a dick in my sensitive sissy hole was enough to start my tears streaming. His pumps matched the gentle kisses to my wet cheeks. I was on an emotional rollercoaster. This man was hurting me, stretching me out so much…then out of nowhere, I wrapped my arms around his strong back and neck. My pussy was opening up for him, I howled a combination of “NO, take it out, take it out” and “Please cum in me, shoot your nasty cum it in me!!!” His pace quickened, and the power of his pumps let me know he was no longer holding back. All I could do was hold on to him for dear life as he took my sissy pussy. On top of me, his chest and ab muscles tightened; I could feel this arm flex around my legs, and I knew his was about to seed me. The python in my ass began to flex and unflex like his muscular arms and I knew it was pushing cum in my...or now his pussy. His muscles from his shoulders to his toes contracted over and over as he continued to hump me, but now his pace was much slower.
His oversized cock contracted for the final times, and Darin released the bear hold he had on me. Tears were still running down my cheeks as I started to release my grip on him as well. He leaned back and his cock, slowly and painfully withdrew out of me. “It’s okay baby…it’s okay.” I think he was looking at me trying to understand what had just happened to me. I had never had ANYTHING like that in me, I had never been so manhandled and manipulated. I had seen girls in videos take huge dicks in their ass, but this was so different. They knew what was about to happen, I had no idea. When he stood up, I was wet with his sweat, and I felt my legs stay back as if he was still pushing them back as far as they would go. “Relax now” he said in a calming voice. I slowly lowered my legs as a flood of emotions took over. Globs of his cum was leaking out my gaping asshole. I didn’t care. I looked down and noticed as I came, a lot. There was cum all over the front of my dress and neck. I thought it was him, but he was too busy fucking the shit out of me and emptying his balls full of sperm into my aching cunt.
I teared up again as, yet another rush of emotions really hit me. The pain in my butt was fading away, but I felt so weird. I really broke down. Darin sat next to me on the couch, and I just collapsed in his lap and cried more. Darin continued to allow me to sob on his lap while rubbing my hair until I was exhausted. He stood up and finally pulled out the sofa bed, put on fresh sheets and two fluffy pillows at the top. “Time to go to bed baby” he softly whispered to me. I got under the sheets and was almost asleep when he suddenly spooned up behind me. I almost jumped, but he said in an assuring tone, “It’s okay baby I’m not got to do that to you again, just get some sleep. I so wanted to trust him, but his dick rested so close to the scene of my destruction. “I’m, I’m…I don’t know, but please….” Blubbered out, “Shhh…It’s okay” he said quietly, lovingly and I was off to dreamland.
The morning sun brightly beaming through the basement window, and I wiped the sleep from my eyes. Slowly and carefully, I removed Darin’s beefy arm that was wrapped around me and made me feel protected. Finding a folded large t-shirt on the laundry table, unfolded it, it read “Mack” on the front with a picture of a weird looking metallic dog, I was sure he wouldn’t mind, and I slipped it on. Standing there half naked from the waist down, I could now process what was happening to me and I was okay with it. I went upstairs, just wearing the oversized t-shirt and started making coffee and frying Darin a couple of eggs. I knew that man had just brutalized my still kind of sore sissy pussy a few hours ago, but he was just the type of bull daddy that made me feel safe, I was his biker bitch chick.
Matt told me to just be myself because I knew most of the people there, so I had a little black dress I had been dying to wear. Over time I had grown my hair down to my shoulders and dyed it purple with red highlights and I had some Skull Girl barrettes. The last parts were the pink Nikes and babydoll socks. I always stay shaved, all over and underneath, and my perfume was very light, and Matt said it made me smell girly, but he still wouldn’t let me at least blow him…. oh well, a gurl can dream. Once Matt picked me up, he asked “What are you all dressed up for?” “For your party silly” I shot back. I really wanted to give him a going away present, but the chances were next to zero, but I planned to try anyway, and I think he knew because I wore everything that he said, “fits me.”
The party was in the basement of Matt’s uncle, he had a nice home and Matt said he was a great guy, but that was his uncle. I heard so many stories about how back in the day about the gang he road with and some of his legendary fights, but Matt said since he has done his time, he has mellowed out, regardless I steered clear of him. The music was loud, I could hear it from the side of the house. We walked in headed downstairs and once Matt arrived there was a ton of “Congratulations!” and the party really started. From the start, as soon as we made it to the basement we were split up. Some of the girls there grabbed me by the head and dragged me away and Matt was Matt, always the life of the party. The girls always asked me the same questions about Matt, the one that bugged me the most was “Is he gay because he is always hanging out with you?” “No” he is not, blah, blah, blah.
A few of the guys were hitting on me and some of the other girls and Mikey (my former bully) was ALWAYS “accidently” bumping into me, and after a few drinks he was straight forward trying to feel me up. As the night when on, I felt a hands on my butt, that was fine but seeing Matt’s uncle leering at me gave me the creeps. I started to feel like my dress was too short, but I just continued on and enjoyed the party. Looking at my watch it was around 1am and I was looking for Matt to take me home. I had a few drinks, and I was tipsy but not drunk. I couldn’t find Matt anywhere, one of the girls said right before she left that Matt was hooking up with some skank that blew him in the bathroom. WTF?! When she left, I was the last girl at the party, no I was the last person at the party. I started looking for my purse to grab some money to get a cab. Shit, I left my purse at home! Seemingly on queue, Matt’s creepy biker uncle came around the corner. He had a plastic garbage cleaning up after everyone. My heart dropped. I asked for a ride home because I lived on the other side of town and had no money. He said he had to finish cleaning up and he will see what he could do if I helped him clean.
I notices him looking at my ass each time I bent over to pick up a red cup and other trash. “I know you remember me…Matt said you call yourself Kelly now right?” “Yes” I got out. “Look, there is no need for you to be scared of me, I know who you are and what you are. Let me finish cleaning up down here.” “Hey there is still beer and some Wild Turkey on the counter” he said trying to be nice. I took a few sips to just chill out as he cleaned. As he cleaned, we actually talked and shared some laughs, and finished off the remains of the Wild Turkey. The more we talked the more we sipped the secret stash of Crown Royal that was behind the counter. It was nearly an hour when Darin, Matt’s uncle’s real name, finished cleaning and sat down on the couch. He admitted he took a few more sips than he should have and due to his last DUI, driving was out the question, but he did offer me the pull out couch.
I think due to the alcohol we became freer as we talked. He made comments on how I made a pretty gurl, with my little chubby legs, cute outfit and how I smelled really nice. He next asked me if I used coco butter on my legs. The smell was familiar because that is what some of the sissies in prison used to try to be more feminine for their cell daddies. Then making an animated gesture he made a cool comeback, “…But you are out of this world gurl.” He laughed and I giggled, and he told me I had a cute laugh. I asked him about prison, and he told me all about his time there, and he had a couple of bitches that offered ass for protect, that’s the game. Replying back, I told him I could totally understand, because I would never survive. “Yeah…you right, because the guards and the inmates would be fucking you every night.”
I laid back on the couch and slipped off my pink-hearted “Saturday” panties. I did as he asked and laid back again while spreading my legs wide. It was like he was enchanted will my boi hole. “Fuck, fuck, fuck gurl…my God you are blessed!” “That is the prettiest asshole I have EVER seen!” Surprised, I asked “He said you had your…bitches?” “Yeah, but not this pretty.” Its was weird, I never had anyone complement my asshole. “And I love that you are shaved all over, shit you fine.” I was thinking I wanted this to be my present to Matt, but Matt only wanted real girls, but I was going to try my hardest for his last day in town. Now my gurly brain was really confused.
Darin moved so close; he was literally inches from my boi hole. Dropping his shorts, he whipped out the biggest, thickest dick I have ever seen in my life…Holy shit! “Wait wait wait, you said you just want to see it.” “I need to kiss it, I promise you will….” and before he finished what he was saying, a skilled tongue explored my sissy cunt. My little clitty was at full attention, OMG it felt so good. Yes, I have been licked back there before but never like this. I scooted down, grabbed the back of my knees and pulled my legs back as far as I could. I wanted to stroke myself but when I touched my clitty, Darin gave a “Don’t touch it!” He had a plan, and I honestly thought, he planned this all along; but I didn’t care I just wanted him to keep doing what he was doing. Closing my eyes, I gave a heavy moan and it felt like his tongue went deeper in my asshole. I didn’t know if I wanted to use my hands to keep pulling my legs back or to spread my ass cheeks wider. He knew what to do to me and I loved it.
It had to be a good 20-30 minutes when he removed his face from my bottom. When he stood up, he had a raging, veiny 10-11 inch hardon that he was pumping. The head of his dick was soooooo big, it looked like a big brown doorknob! “I think your ready baby” he said slyly. “Ready for what?!” “There is absolutely no way that thing will fit in me, no fucking way!” said in a high pitched tone. “That thing is huge, no…no way!!!” Darin smiled because he noticed during all of my protesting, I never got off the couch. His hands replaced my hands behind my knees. “No, you can’t…it’s too big…I’m not ready.” “I got something that will help” with that Darin strolled over to the side of the counter. I Just watched as his hard fat snake bounced as he walked. I didn’t move or try to run; I just laid there spread eagle on my back, in my little black dress and my panties on the rug. I was filled with the terror of his monster trying to enter my tiny little puckered hole and the OMG factor this really happening thoughts. My mind was trying to figure out why I was growing attracted to his old biker. Up until now I would never find myself in the company of people like him, but now, some weird attraction kept me on the couch spread like some girl in a video.
Darin came back with a can of cooking oil. “You are going to spray cooking oil on my asshole?!” I said in a questioning and surprised manner. “Trust me” he said so coolly. “Please don’t hurt me…okay…be gentle. I have never had anything like what’s between your legs come near me before.” I said while staring at the snake that was about to make me a biker bitch.
Shaking the can, he coated my butthole with the cooking oil spray, next was his cock. When he started rubbing oil on his cock, I could see all the veins and the head looked even bigger. I kept telling myself it too late to get the hell out of there, why didn’t leave when I had the chance? Darin got into mounting position, put his hands behind my knees again and slowly lowered himself. “Kelly…just try your best to relax…we are going to take this nice…and slow...okay” I nodded my head yes, letting him know I was completely trusting him. His cockhead kissed my rear door and I started breathing heavy. He looked directly in my eyes and said, “Look at me baby” Now, I was talking fast, “How can I just look at you when…when…do you know how big you are?!” “It’s going to hurt so bad” I was near distressed. When I had my virginity taken, it was rough, but I wanted to be fucked like a girl so much, I took it, but the guy that took me was half the size and thickness of on Darin. As I was rambling, I felt Darin’s cock start stretching out my sissy hole. More and more it opened like it was being pulled apart. In a wavering voice, I looked at him with eyes as big as saucers and gave an, “Ouchy…..ow…oh my God please stop…Darin…ooooooo…” For his part he never stopped his slow and steady pace. For my part, I clutched the couch cushions with a death grip. Inside my pink Nikes, my toes were locked in the spread position. It was an absolute struggle as he entered me, and he was only halfway in.
“Listen to me, don’t look at a dick, look at me baby.” “I can’t do this…it hurts” “It’s okay baby” Darin said softly as tears began to well in my eyes. “You are doing so good baby, let daddy guide you.” That’s when he got fully on top of me, his tatted up arms pinned my legs back and his cock drilled in until I felt his pelvis rest on my little belly. The pain of being impaled with his old biker’s baseball bat of a dick in my sensitive sissy hole was enough to start my tears streaming. His pumps matched the gentle kisses to my wet cheeks. I was on an emotional rollercoaster. This man was hurting me, stretching me out so much…then out of nowhere, I wrapped my arms around his strong back and neck. My pussy was opening up for him, I howled a combination of “NO, take it out, take it out” and “Please cum in me, shoot your nasty cum it in me!!!” His pace quickened, and the power of his pumps let me know he was no longer holding back. All I could do was hold on to him for dear life as he took my sissy pussy. On top of me, his chest and ab muscles tightened; I could feel this arm flex around my legs, and I knew his was about to seed me. The python in my ass began to flex and unflex like his muscular arms and I knew it was pushing cum in my...or now his pussy. His muscles from his shoulders to his toes contracted over and over as he continued to hump me, but now his pace was much slower.
His oversized cock contracted for the final times, and Darin released the bear hold he had on me. Tears were still running down my cheeks as I started to release my grip on him as well. He leaned back and his cock, slowly and painfully withdrew out of me. “It’s okay baby…it’s okay.” I think he was looking at me trying to understand what had just happened to me. I had never had ANYTHING like that in me, I had never been so manhandled and manipulated. I had seen girls in videos take huge dicks in their ass, but this was so different. They knew what was about to happen, I had no idea. When he stood up, I was wet with his sweat, and I felt my legs stay back as if he was still pushing them back as far as they would go. “Relax now” he said in a calming voice. I slowly lowered my legs as a flood of emotions took over. Globs of his cum was leaking out my gaping asshole. I didn’t care. I looked down and noticed as I came, a lot. There was cum all over the front of my dress and neck. I thought it was him, but he was too busy fucking the shit out of me and emptying his balls full of sperm into my aching cunt.
I teared up again as, yet another rush of emotions really hit me. The pain in my butt was fading away, but I felt so weird. I really broke down. Darin sat next to me on the couch, and I just collapsed in his lap and cried more. Darin continued to allow me to sob on his lap while rubbing my hair until I was exhausted. He stood up and finally pulled out the sofa bed, put on fresh sheets and two fluffy pillows at the top. “Time to go to bed baby” he softly whispered to me. I got under the sheets and was almost asleep when he suddenly spooned up behind me. I almost jumped, but he said in an assuring tone, “It’s okay baby I’m not got to do that to you again, just get some sleep. I so wanted to trust him, but his dick rested so close to the scene of my destruction. “I’m, I’m…I don’t know, but please….” Blubbered out, “Shhh…It’s okay” he said quietly, lovingly and I was off to dreamland.
The morning sun brightly beaming through the basement window, and I wiped the sleep from my eyes. Slowly and carefully, I removed Darin’s beefy arm that was wrapped around me and made me feel protected. Finding a folded large t-shirt on the laundry table, unfolded it, it read “Mack” on the front with a picture of a weird looking metallic dog, I was sure he wouldn’t mind, and I slipped it on. Standing there half naked from the waist down, I could now process what was happening to me and I was okay with it. I went upstairs, just wearing the oversized t-shirt and started making coffee and frying Darin a couple of eggs. I knew that man had just brutalized my still kind of sore sissy pussy a few hours ago, but he was just the type of bull daddy that made me feel safe, I was his biker bitch chick.
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