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Uncle Charlie

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Tiffany's fantasy becomes reality.
4.4k words
4.37
406.5k
60
1

Part 1 of the 4 part series

Updated 10/24/2022
Created 11/30/2000
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SpankerSam
SpankerSam
2,228 Followers

"Hello Uncle Charlie. Hi this is Tiffany. Are you by chance going up to your cabin this weekend?"

"Great! Do you think I could come up and spend the weekend."

"No nothings wrong, I just feel a bit burned out. I figured a weekend without the phone or friends would recharge my batteries."

"You still call me baby girl after all these years."

"Thanks Uncle Charlie, you're the best." I hung up the phone and smiled as I lay back on my bed. I had planned this moment for months.

I thought back to the time that caused me to feel this way. I was 16 and lived with my mom. My dad left us soon after I was born. Being one of 7 children my mom had lots of sisters and brothers. But Uncle Charlie was my favorite. He was younger than mom but always acted older than she was. She always looked up to him and it was just natural that he would be like a second dad to me. He was there for every birthday, Christmas, good time and bad.

He was also the one who gave me most of my spankings. The last time Uncle Charlie spanked me I was 16. Mom had to go out of town on business and he volunteered to stay with me. Since he was at our house most of the time, it was no big deal. Anyway, I was supposed to go to a party that Friday night. It was a costume party and I was going dressed like a slut.

My costume was a sweater two sizes too small, a skirt that barely covered my cunt and ass, high heels and no underwear. I was also taking smokes and a bottle of wine. Uncle Charlie was sitting in the living room when I was ready to go. He knew about the party but didn't know what kind of party it was going to be. We had finished dinner and he was drinking his favorite drink as he watched TV. He always called me his best bartender. It was my job to fix all his drinks. I had made his last two kind of strong hoping he would fall asleep before I left. I was ready to go out the door when Uncle Charlie called me to the living room.

"Let me see what you're wearing. Can't have you going out looking like some easy pickup for all the horny boys out there." With that he made me open my coat. His eyes got wide when he saw how I was dressed. "You must have lost all the little bit of sense I thought you had. If you think that you are leaving this house dressed like that, you have another thing coming."

I begged and pleaded with him to let me go dressed as I was. I told him that I would be OK. I knew everyone at the party and wouldn't let anything happen that I didn't want to. At 16 I had lost my virginity awhile ago.

"It's what you may want to happen that scares me. Either change your clothes or don't go. That's my final word." There was one thing that I knew about Uncle Charlie. When he gave his final word on something, even mom didn't go against him. I was either going as I was or stubborn kid that I was, I wasn't going.

Well I have always been a stubborn, hardheaded kid so I there I was sitting in my room pouting. I'd show Uncle Charlie, I sat on my bed, drinking wine from the bottle. I should have known that uncle Charlie would stick his head in to check on me. Even when he was mad and had given me a spanking, he would still check on me and tell me that he was sorry he had to spank me. Well this time when he stuck his head in the door, (without knocking) he found me propped up on my bed. I was still dressed in my sweater and skirt.

That wasn't so bad, except that I had the bottle of wine in my hand, a cigarette in my mouth and a dildo between my legs.

I had been thinking about the club that I was supposed to join at the party. A few of the girls belonged to a double-fuck club. That was where a girl was being fucked in both holes at the same time. That was part of the reason for my costume. He stood there staring at me and I saw his eyes grow cold. Oh shit! I was in for it now. There would be no excuse I could give him that would sooth his anger.

"Get your nasty ass in the living room." He left the door open and I reluctantly got up and with head bowed went into the living room. He sat in his chair, smoke rising around his head as he puffed hard on his cigarette. It looked almost like smoke was rising from his head but I dare not laugh. He was madder than I had seen him in a long time. I stood in front of his chair.

"I could have forgiven you for wearing that slut outfit. I could have even let it go that you were ready to sneak out the house wearing it. But that disgusting spectacle I saw as I opened your door, that I would not forgive." I stood there in my outfit and for the first time since I put it on, I felt dirty. "Take that shit off."

I turned to go to my room.

"Where the fuck are you going? Take off those clothes. Right here! Right now!" This was going to be a bad spanking. I was just a bit smaller than I am now. At 16, my tits were developed; my ass was just a bit smaller than it is now and I had been having sex for the last 2yrs, so I know my pussy was just as grown up as it is now. I stood before Uncle Charlie and pulled the sweater over my head. My twin mounds were firm.

They stood up with no support. I dare not look at Uncle Charlie as my fingers hooked my skirt and pushed it down over my hips. I stood before him now totally naked. He looked at me for a few moments, then grabbed my hand and pulled me over his lap. His hand rested on my soft ass. I knew that my ass was soft and round. Many boys would rub and squeeze my ass whenever they got the chance. Uncle Charlie didn't seem interested in my soft ass.

He raised his hand and liquid fire landed on my ass. I remember screaming and kicking my legs. Over and over his hand landed on my ass. Somewhere during the spanking, things changed. I remember feeling a fire begin to simmer between my legs. I know that my moans changed pitch. Uncle Charlie was rubbing my ass as he scolded me. "I will not allow you to run around looking like some cheap whore. Your mom and I have worked too hard to make you into a lady. I never again want to see you dressing the way you did tonight. No more smoking! No more drinking! At least not until you become of age. Then you can do whatever you want."

I could feel wetness between my legs. I hoped that it wasn't showing on Uncle Charlie's robe. Suddenly he began to spank me again. This time though, he was spanking me on my thighs. His big rough hands were landing on my ass, my thighs and even between my legs. Sometimes his hand would slap the lips of my pussy and I know I moaned when he did. Not from pain, I had stopped feeling pain. Instead I felt the fire burning hotter.

I was moaning and calling his name when he finally stopped. I stood up and turned to look at my uncle. There was no mistaking the big lump in his robe. He sent me to my room and told me to close the door. I can only guess that he must have given his hard dick a good workout. Back in my room, I couldn't help but finger my hot pussy till I came. I didn't connect his spanking with my horniness until years later.

Now here I was almost 10 years later. I never forgot the feeling that Uncle Charlie's spanking gave me. Nor have I found anyone who could make me feel that way. I learned a lot since my last spanking from Uncle Charlie. I found out that there was a lot more between him and my mom than I thought. But that is a story all by itself. I had planned a very elaborate scheme to get Uncle Charlie to spank me again. Friday came more quickly than I would have wanted.

I met Uncle Charlie after work and we took the ride to Pennsylvania in his jeep. We stopped at the liquor store and also stopped at the supermarket. I asked Uncle Charlie to start a fire as soon as we got to the cabin. We talked all during the time we made dinner. After dinner when we were sitting before the fire, I said I was going to take a shower. I went to my room and took a quick shower. Then I dressed in the lingerie I had picked specifically for this moment and put my robe on over it. Uncle Charlie had also gone and took a shower. He was sitting in his robe before the fire when I came out my room.

When I was younger I would sit on the rug by his side. Many times, mom would sit across from him. I would sit and listen as the two of them talked about things I couldn't understand. Now at 25, I was sitting on the rug at uncle Charlie's feet. We were both sipping the drinks I had made. I still made his drinks, only this time; I made his twice as strong as mine. I leaned my head on his knee and just like when I was a child, his hand dropped down on my head and he twined his hand in my hair.

"Remember when I was small Uncle Charlie? You were just like a dad to me. You were there whenever I needed you. You bought me presents, told me what to do and even spanked me when I was bad."

Uncle Charlie laughed. "And as I remember, there were times when you were very bad." I could tell that the drinks were having their effect on him. It was time to play my ace card. I laughed along with him. "Remember when I was 16 and tried to sneak out to that party. You gave me the hardest spanking I can ever remember."

Uncle Charlie's hand stopped moving. "I remember. You had dressed like a slut to go to some party. I said no and you went into your room. When I came to check on you, you were sitting up in bed, drinking from a wind bottle. You had a cigarette sticking out your mouth." He stopped talking then.

"You can say it Uncle Charlie. I'm a lot older and wiser now. I was sitting on my bed with a dildo stuck in my cunt. You made me undress and lay across your lap. You gave me a spanking I have remembered all these years. But something else happened that night."

I let things hang unsaid. Uncle Charlie didn't say a word. His hand started stroking my head again. Only this time it was softer, gentler. "Uncle Charlie?"

"Yes baby girl."

I smiled at hearing him call me by my pet name. "Can I tell you a secret?"

"Honey, you know that you can tell me anything. What's the matter?"

"Remember the night you spanked me? Well sometime during that spanking, things began to change. All of a sudden the spanking made me feel so hot and funny. I didn't know it then, but that spanking turned me on in such a way, I've never felt like that since. I've tried to find that feeling with other men, but nothing ever duplicated it."

I could feel Uncle Charlie as his breathing changed. He was starting to breathe a bit faster. "What are you trying to say baby girl?" I turned around and looked at Uncle Charlie. He was older than when I was 16, but he still had a way of making me feel so good inside. It was now or never. I had to take a chance and put all my marbles in one pocket. His eyes looked down at me. I just know he knew what I was about to say. I took a deep breath and closed my eyes.

"I want you to spank me Uncle Charlie. Spank me the way you spanked me when I was 16. I have to know if what I'm feeling is real." I felt his hand clench as he held my hair. It hurt but I dare not cry out. I bit my lower lip until it almost bled.

"I can't baby girl. Please don't ask me to do that. You don't know what almost happened the last time I spanked you." I was not about to let his fear stop me at this point. I had planned too long and gotten too close to what I wanted. No! What I needed. I turned until I was kneeling before him. Between his legs the way I used to do when I was a child.

"I do know what happened Uncle Charlie. I saw the erection you had. I know how close you came to making love to me. The way you felt my ass, the way you squeezed and kneaded my flesh. I need you to do this Uncle Charlie. I have to know if what I felt was only because it was you spanking me. Will you make me go from man to man like the slut you saw me dressed as? Is that what you want me to do Uncle Charlie?"

I opened my robe and let it fall. Uncle Charlie looked at me. I was dressed in an outfit that left nothing to the imagination. The material was sheer enough to seem invisible. He could see my hard nipples and the hair on my cunt.

Uncle Charlie was breathing heavy. I could see him lick his lips. His hand shook and he half lifted it then let it fall. A soft sob escaped his throat. "Do you want to think about some pervert spanking me? Do you think he'll care about me the way you do? Or will he hurt me? I need you to do this for me. I need you like I never needed you before. Do this for me Uncle Charlie. Do this for us." I laid myself across his lap and held my breath. I felt his hand, still rough, still strong as he set it on my ass. He was slowly squeezing my cheeks. I began to breathe again.

I felt the wetness between my legs begin to grow. Uncle Charlie raised his hand. For almost 10yrs I thought I remembered how his hand felt. But I wasn't ready for the liquid fire that burst upon my ass. It hurt like hell but the only thing I could do was moan. "Oh Uncle Charlie", was all I could say. His hand raised and lowered again and again. I felt the hot tears roll down my cheek. I also felt something else. It was him. It was the spanking that Uncle Charlie gave me that made me so hot. The ember that had simmered in my pussy all these years burst into a blazing inferno. He didn't hold back. He spanked me with his bare hand and I felt like a child again. But this time I was a woman. And I had knowledge that would make this night like no other night in my life.

Uncle Charlie spanked me again and again. I cried and I came, over and over. When his hand stopped, he was rubbing my ass. His hand slipped between my thighs and I opened them gladly. When his fingers touched my throbbing pussy I moaned and welcomed his probing digits. I knew what I had to do now. I slipped from his lap. As I knew it would be, his dick was hard as stone. I knelt between his legs and as my hand sought his throbbing cock, he wrapped my hair in his hand. As my mouth slipped over the pulsing head of his cock, his hand tightened in my hair. He pulled hard until I moaned as my tongue washed his cockhead. I knew what he would do next and I steadied myself.

As I knew he would, he began to work my head up and down. He was forcing me to take his entire dick down my throat. I was ready for him. As a matter of fact, I had practiced on a few boys just getting ready for this moment. I knew he wouldn't cum this way. I smiled to myself even as I felt the gag reflex begin. I gagged and choked just like he expected me to. He pulled my head off his dick and smiled down at me. Had I not known what to expect, that smile would have scared me half to death. He was no longer the loving, caring and sweet uncle I so loved. He was a man consumed with his own private lust.

He pulled me up onto his lap. My legs straddled the chair, facing him as he pulled me close to him. Even though I was ready for his intrusion, the sheer force of it made me scream. He pulled me down on his throbbing cock as hard as he could. Then he raised me up and slammed me back down on it. I knew what he wanted to hear. I grabbed his shoulders.

My nails dug in hard. I knew they were drawing blood but I had come too far to back down now. "Make me behave. Fuck me till I promise not to act like a slut anymore. Oh Charlie! You incestuous bastard. Give it to me." I knew those words would inflame him even more. My pussy felt like he was ripping it apart. I had never felt a more delicious feeling in my life. There was no going back, no stopping him from this point on. He was mine and I was his until the ride stopped. With his strength alone, he picked me up.

Still attached to his throbbing shaft that was buried deeper in my cunt than any other man had ever been, my legs wrapped tightly around his waist, he walked with me to the bedroom. I grunted as we fell on the bed and he slid in even further. The muscles in my cunt were going berserk. I don't know how many times I had cum already. But he was just getting started. I just hoped I could last thru what was to come.

Uncle Charlie pulled his dick out until just the tip was in. Then looking down at me, he slowly slid it up into my pussy until I grunted from the full insertion. My nails were ripping into his back something fierce. He fucked me slow.

I begged; I pleaded but he wouldn't stop. Then he pulled out. I lay moaning my legs splayed open before me. He grabbed my ankles and turned me over on my stomach. I felt him pull me up by my waist. His tongue was red hot as he licked my puckered hole. Only two men have ever fucked me up the ass. Both of their dicks were much smaller than Uncle Charlie's and they had been gentle. Uncle Charlie would not be gentle. His tongue stabbed into my asshole repeatedly. I knew he was getting me ready for his assault.

I tried to relax and calm my breathing but nothing worked. Then I felt his thumbs prying my cheeks apart. I took a deep breath and held it. Nothing could have prepared me for the searing pain. I though he had ruined me for life. I remember screaming and then I think I passed out. The next thing I remember was hearing him grunt every time he shoved that red-hot poker up my ass. I lay there crying and screaming from the pain.

Then I felt him stiffen. He shook all over then let out a loud scream. It felt like he was shooting gallons of cum up my ass. The hot cream scalded me at first then seemed to bath my tender, ravaged asshole with a soothing balm. I don't know if I came from his brutal assfucking. But I felt more alive than I ever felt in my life. He collapsed on top of me and held me tight.

I cried out as he pulled his withering cock from my ass. Then I turned in his arms and held him. 'Why baby girl? Why did you make me do this?"

I could only shower his face with kisses as I kept repeating, "Thank you Uncle Charlie. Thank you!" I held him in my arms as he cried.

After what seemed like an eternity, he drew back and looked into my eyes. I was crying too. "I love you Uncle Charlie. I always have. I needed you to give me what no other man ever could."

"But how did you know? No don't answer. I'm afraid to find out." I snuggled close to him and whispered in his ear. '"You want to know. I know you too well Uncle Charlie. I know you won't dare ask mom so I will tell you."

I kissed him long and hard on the lips. Reluctantly his lips parted and his tongue sought mine. I broke the kiss and smiled at him. Even with my asshole screaming, my cunt throbbing, I wanted more of this man. I wanted him like I never wanted any man in my life. I smiled at him and he gave me a crooked smile in return. "I'll tell you. But not before we take a shower. I need another drink. Jeez! I've never been fucked like that in my life." I got up and went into the bathroom. He followed me in and we washed each other in the shower.

We were seated back before the fire. Drinks in our hands as we stared into the dancing flames. "When I was 18, after working for awhile, I decided to by mom a new mattress and boxed spring. She was out of town on business and I was going to surprise her when she got back. Well I took the old stuff and turned it on its side. I was dragging out the boxed spring when I heard something rattle. Inspecting I found a bag had been pushed up into a hole in it. I took the bag out and opened it up. I found a bunch of pictures tied with rubber bands. The first picture had mom dressed in a see-thru nightie. Being curious, I looked thru all of them. One picture showed her with her lips wrapped around a dick. Thinking they were pictures of my dad, I kept looking. Imagine my shock and surprise when I saw a picture of you lying on the bed naked. The sheets were the same as the ones she was laying on so I guessed you had taken pictures of her and she you. Along with the pictures was a videotape. It showed you fucking mom the same way you just fucked me. That's how I knew what to say and what to expect. Well when mom came home and found I had changed her mattress and boxed spring she freaked. She was ranting and raving about me messing with her things. When I handed her the bag, she looked at me and knew I had seen what was inside. She broke down and cried. That night she told me everything about the two of you. That's when I made up my mind that I had to make you fuck me. I'm not jealous of mom Uncle Charlie. This has nothing to do with her. Since the time you spanked me there has been a big hole in my life. No matter what man I was with, they never seemed to satisfy me completely. There was always something missing. After seeing the pictures, the video and talking to mom, I knew what it was."

SpankerSam
SpankerSam
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