A Family Affair Ch. 05

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Daddy takes my anal cherry.
2.3k words
4.46
24.6k
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Part 5 of the 5 part series

Updated 06/11/2023
Created 03/29/2022
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** At the time of writing, I'm currently 48 years old and divorced for maybe 16 or 17 years. I cant quite remember. This is my attempt to string together some of my past experiences that rightly or wrongly have shaped who I am. I hope you enjoy reading this and please don't judge me. I'd love to receive comments from my readers too so feel free to say what you want. **

In the previous chapters, I briefly explained how I stared sleeping with my Uncle, then my Dad and my two brothers. It went on and I was never sure if the others knew but I suspected they did. No one really said anything. Dad was the most often -- at least once a week but usually 2 or 3 times a week. With Mark, it wasn't that often. He liked blowjobs though and would often get me to blow him. With John it was also about once a week.

I learnt I liked giving blowjobs and I perfected my art with Mark. I learnt how to deepthroat with Mark and I learnt how to read a man's sighs and groans and adjust what I was doing to give him pleasure. With Mark I also learnt that how to tease his balls while I was sucking him and even tease his ass hole. I slipped my finger in a few times too and the response was amazing.

It was also then that I learnt what the prostate was and how massaging it or teasing it while sucking seemed to elicit such a wild response from Mark. He would cum in buckets too if I stimulated his prostate and I'd have a hard time swallowing it all down.

Mark also loved to cum on my face, something that I wasn't particularly fond of but something I knew he liked. Over the years, with different men, what I had learnt and practiced with Mark came into good practice and I was often told I had an amazing mouth.

For me, giving blowjobs gave me an immense feeling of power. I know some men think that women are subservient during the act of giving a blowjob but to me it felt like I had the power. I mean, I was the one sucking you and controlling when you came. I was the one drawing his seed into my mouth and following it. I was the one that was making them glassy eyed and begging for release. So in my mind, it was a very powerful thing.

And as I said, I liked it. I liked the taste, I liked the feel, I liked the smell. The feeling of a hot cock in my mouth, pulsing and tensing when I licked it or sucked it was just amazing. The feeling of the cock head swelling and then spurting warm liquid into my mouth was divine. I just loved giving head.

Surprisingly, none of my boys, yes, I called my Dad and brothers my boys, gave me oral. Sure, they would lick a little to get me more wet but they never spent and time down there. At that point in time it suited me fine as I would much rather be sucking a cock then having my cunt licked. That kind of stayed with me for a long time. I guess some of it had to do with me wanting to feel fresh all the time and I was kind of turned off by how I might smell or taste and that inhibited me.

But anyway, back to another experience.

It was a Saturday afternoon and both my brothers were out somewhere. I was lazing on the couch, switching channels on the TV, not really watching anything in particular. I was wearing an old, thin frock, one of what I called my houseclothes. Nothing that I would ever wear outside the house. It was ratty and used but comfortable. Perfect for lazing at home.

"Whatcha watching?" Dad asked as he stood in the entrance to the lounge.

"Umm...nothing really, just flicking channels."

"Anything interesting?" He asked.

"Nah uh." I replied, shaking my head.

Dad smiled at me and cocked his head toward his room, his indication that he wanted some. "No one is home. And I love how you look in those old clothes of yours."

"Daddy wants to fuck me?" I teased.

He smiled. "How do I resist you. Come."

I got up and followed Dad to his room. I have to admit my pussy was tingling slightly at the thought that Daddy wanted me and was going to fuck me. Once in his room, I pulled my dress off and then peeled off my panties and unhooked my bra. I moved to lie on the bed, naked, as I watched Daddy undress.

Daddy climbed in beside me and stroked my face. "So pretty." He said softly. My hand moved to his chest, rubbing it slightly then down to his cock. There was no real kissing or teasing with Dad. It was straight into bed and almost straight at it.

His cock grew harder in my hand and I rubbed some of the precum over his head. Daddy sighed. I moved in closer to him, nuzzling against his chest. "How do you want me Daddy?" I asked softly, my hands playing with his cock.

Daddy groaned. "Sit on me. I want to watch you."

I clambered up and threw one leg over him. I positioned my pussy over his stiff dick and slowly lowered myself on to his upright cock. His meat slowly parted my lips and slipped into me. I hissed with pleasure at the first entrance and slowly worked my way down till all of his cock was inside of me. I placed my hands on his chest as I planted my ass firmly down and smiled, looking down at him.

"Just sit there. You feel so warm and tight." He said. He pulled me down slightly toward him and raised his head up to take one nipple into his mouth. His tongue swirled and lashed at my nipple as his other hand moved between my legs to find my clit. His thumb started rubbing on my clit as I felt his cock throb hotly in my pussy.

I moaned with pleasure and started to rock my hips against him, pressing harder against his thumb against my clit. His other hand moved to my back and pulled me closer to him as he started to thrust slowly into me. I groaned louder now.

"Oh god. Fuck me Daddy.. fuck me...Unnnnhh." He released me and I started to ride him, plunging my hips and and down on his cock. His thumb kept rubbing on my pussy as I pumped up and down on his cock. I could feel my orgasm starting to build in me and his thumb on my pussy only served to heighten my pleasure. I raised myself on my knees to get more leverage and started pounding my fathers cock deeper into me.

"Fuckk...Daddddy...Daddddy....Dadddy....I'mmm gonnaaa cummmmmm!" I cried out as I planted myself firmly on his cock and felt my pussy spasm and my body tremble. His thumb was working hard on my clit as I orgasmed and that drew out my orgasm longer and harder. I quivered and shook on his cock as my hand flew to his to stop him strumming my clit. It was just too intense. I looked down at him and he had this grin of satisfaction as I ground my pussy against his cock. My mouth was open and I was moaning loudly.

My legs finally stopped quivering and I smiled down at Daddy. I started to move again, slowly up and down. He placed his hands on my breasts, tweaking them. "Wait. I don't want to come yet. Get up. Get on your fours." He said.

I climbed off his cock and I could see my white cream coating parts of the base of his cock. That sight excited me more. I started to kneel to position myself. "I should have taken your cherry." Daddy said.

"I lost that some time ago Daddy." I laughed. "Sorry."

His eyes took on a glassy look. "What about your ass? Is that still Cherry?"

"Daddy!" I exclaimed, in shock. "I..I..I've never done that."

His finger slipped into my buttocks crack and wormed its way into my ass. I gasped at the intrusion and instinctively tensed my ass muscles. "You're mother hardly did it. Even when she did she always complained."

I don't know what it was. Whether it was knowing that my mom had done it or the fact that my father said she didn't like it. I wanted to do it then. I needed to know what it was like and if I could please my father. Do something for him that my mother was reluctant to do.

I raised my ass higher, feeling his finger push deeper into me as I did so. "Be gentle Daddy?"

"Are you saying I can fuck your ass?" He asked. I could hear the lust in his voice.

"O..only if you want to Daddy." I replied, a little unsure of myself.

I felt my ass cheeks being parted and then what I only can think was spit being applied to my ass, feeling it drip down my crack and then daddy's fingers working it into my hole. I felt him spread me further and then he plunged his cock into my pussy a few times, coating it with my juices.

I felt his cock head press against the rosebud of my ass and I tried to relax it as much as I could. I felt him pressing forward and there was immense pressure. I instinctively pulled away a little. Daddy grabbed my hips and pulled me back. One hand wrapped around my hips and stomach, holding me tight. I felt his cock pressing against my ass again. The pressure started to increase.

"It hurts Daddy... ohhh.. fuck... it hurts."

The pressure increased even as I tried to relax my ass muscles even more. I felt a pop as the cock head broke into my ass. Daddy shoved forward and I felt an even more intense searing pain. "Aaagggh.... Godddd... Stoppp stop.... Daddddyy... It hurts.. it hurts.. oh pleaseeeee"

Daddy's cock speared deep into my ass and I felt his balls slap against my ass. My ass burned and throbbed. It really hurt, more so than loosing my virginity. I heard Daddy groan as he flexed his cock inside my ass. I fought back tears as he slowly started to fuck in and out of my ass.

"It hurts daddy... oh goddd.. it hurts.. Daddy please, please Daddy... gently.. Ohhhhh" I cried out, trying to will away the searing pain.

"Fuckkk... so tight sweetie. Your ass is so hot and tight. Fuck yes." Daddy moaned. "Take it baby, I'm in your ass... oh fuck yessss"

As Daddy fucked my ass, I slowly became accustomed to the pain and it wasn't so bad anymore. It was still uncomfortable and I really wouldn't say it was pleasurable, at least not physically. Somehow it just felt kinky and erotic knowing that my ass was being fucked and in some weird way that kind of made it better.

Daddy started to speed up his thrusts, groaning as he did so. I wanted to make it as pleasurable for Daddy as I could and so I goaded him on. "Fuck me Daddy. Fuck my ass. Oh god, you're so big in my ass.... Oh fuck yes."

Daddy moaned at my words and my hand moved to my clit to try and get some stimulus going in my pussy. Slowly I rubbed my clit as Daddy's cock ploughed in and out of my cunt. I felt so much better with my pussy responding now and I was able to focus on the thrills in my pussy rather than the discomfort in my ass.

My father's hands moved to cup my breasts and he pulled me closer to him as his fingers teased my nipples, sending jolts shooting to my pussy. He was hammering into my ass now and the sounds of fucking filled the room. I moaned softly.

Daddy started to grunt and groan louder now as he fucked me. His cock was going deeper and harder into my ass. "Ohh baby.. I'm gonna cum.. gonna cum in your ass baby girl." He cried out.

"Cum Daddy. Cum... cum in my ass!" I said, rubbing my clit harder but knowing I wasn't going to cum. I felt Daddy tense and then he cried out as his cock began to pump it's load into my ass. I could feel his cock swell and then his liquid filling my ass. Daddy pumped my ass a few more times before he buried his cock inside. I could feel his legs trembling against mine. Slowly he pulled out of me and I could feel his cum slowly start to dribble out of my asshole. I collapsed on to the bed, my ass felt empty but it was almost a relief. My anal passage also felt sore even while the rest of my body felt warm and tingly even though I hadn't cum.

Daddy stroked my back lightly as I lay there. "Your first anal girl." He said matter of factly. I rolled over on to my back and gazed at him. I nodded quietly. In a way I was glad that I had given up my anal cherry. It made me feel like a full woman, no longer having any virgin holes and nothing left to hold on to or to hold me back.

I did anal with Daddy more times and also with my brothers and over the years I also did anal with a lot of other men too. I learnt to relax my anal muscles and although it still hurt, the pain was far, far less. For some reason men loved doing anal and I was willing to let them take mine. Most times it was just to make them happy but there were times when I was so turned on I actually wanted to be fucked it in my ass. Those were the times that anal sex was truly enjoyable. But those are stories for another time.

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AkpervertAkpervert6 months ago

You...are my cum dream true! I have never gotten to really get to do an anal. I plunged into my second wife by accident one time, and then we attempted it again one time. But it wasn't quite like you described. And my now wife refuses to let me do that. This was a HOT chapter.

fraserdfraserd9 months ago

Many thanks Erina:

Daddy moaned at my words and my hand moved to my clit to try and get some stimulus going in my pussy. Slowly I rubbed my clit as Daddy's cock ploughed in and out of my cunt. I felt so much better with my pussy responding now and I was able to focus on the thrills in my pussy rather than the discomfort in my ass.

My father's hands moved to cup my breasts and he pulled me closer to him as his fingers teased my nipples, sending jolts shooting to my pussy. He was hammering into my ass now and the sounds of fucking filled the room. I moaned softly.

AnonymousAnonymousabout 2 years ago

ERINA IS JUST THE FAMILY WHORE, AN EASY PIECE

bare5747bare5747about 2 years ago

awesome story and the fact you finally got to take it in your ass. I know anal is not for everyone, my second wife introduced me to it about forty years ago my third wife did it a couple of times but my forth wife likes anal better than vaginal. For me I like eating her ass before I fuck her in it, gets it good and wet for easy penetration. I truly enjoyed your stories and hope you have more experiences to share with us.

AnonymousAnonymousabout 2 years ago

I think I would love to fuck my daughters ass . I was very hard reading this I have fuck a girls ass it was like she said very tight but as you get desperate it gets better that girl likes me licking her fanney till she cums and I licked it till she came every time with a finger up her ass

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