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Anna my dear Anna. Amended Chapter One and Two Finished

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MadChris
Sophomore
Posts: 13
Joined: Thu Oct 30, 2025 5:51 am

Re: Anna my dear Anna. Amended Chapter One and Two Finished

Post by MadChris »

I gave it a few minutes just to make sure that the streets were clear , there was no lights coming from as my neighbouring houses .

I grabbed my fun bag , then knocked on the door , the phone and key's landed in my waiting hand , I looked through the letter box and caught her going upstairs , when she disappeared from view I opened the door , she had showered I caught the aroma of her shampoo , , I moved up the stairs cautiously , step by step .
When I got to the top of the stairs I heard sobbing ,and a single light coming from the open door of a room .
I looked in as instructed she was on the bed , face down her head under a pillow , her hand's behind her back and her long shapely leg's spread wide apart ..
I heard her moan as I sat on the bed , I used a zip tie and secured her wrist together , I turned her over making sure that her head was still under the pillow I grabbed her ankles and tied each to the bed leg's ,
She was stunning , smooth long shapely leg's , a smooth shaved pussy , her breasts were not much larger than Anna's ,
" Well Emily , here I am , and I do hope you won't cause me any problems , just do as I say and you'll soon be seeing Anna , that's what you want isn't it , to see Anna safe and sound again ".
A quiet "Yes " came from under the pillow .
" Good now I'm going to take the pillow off your head , you will keep your face pressed into the sheets do you understand , ?
Another " Yes ".
" Now I am going to ask you a few questions and don't lie to me . I've learned something's about you from Anna ok , I will punish you if you lie .
Where is your husband
Do you have a partner ,
When did you last get fucked .
Do you enjoy sucking cock .
And finally are you an anal virgin

She began to shake and did .
"My husband was unfaithful , we got divorced , I am not seeing anyone I don't want to be hurt again , I haven't had sex since my husband left 3 year's ago .
I detest oral sex , and I have never had anal sex , I think it's disgusting "...
" Mmmmm a good healthy sexy woman like you be craving for a good fuck , or do you have a special little sex toy you use to satisfy your needs , remember don't lie to me " .
" Yes you fucking pervert , I've got a vibrator in fact I've got a few , I find them more fucking useful than any man if you want me to be fucking honest with you ".
I reached under the pillow and with some strips of cloth I had in my fun bag I blindfolded here then turned her over into her back .
Emily moaned , I'm laying on my wrists you bastard can't you tie them in front of me instead .
" They'll fucking stay like that until I'm finished then I'll think about it "
I pulled out a ring gag and told her to open her mouth .
" Your not sticking your fucking filthy cock in my mouth pervert ".
" Ok I'll just call my friend , tell him your not behaving and he can have some fun with your darling Anna , he's been itching to fuck her , and to let you know he's an ass man he loves a nice tight was , I certainly enjoyed popping her anal cherry , she even climaxed for me ".

" No , no , ".
She opened her mouth and I pushed in the ring gag any tied it off at the back of her neck .
I pulled her down to the bottom edge of the bed , I tightened the restraints on both ankles , she was now just as I wanted her , leg's spread wide apart ,when I lifted her hips I could see her tight asshole , it wouldn't be so tight after I finished with her .
" Nice pussy bitch , let's see how tight you are and how sweet you taste , Anna tasted very sweet when she climaxed she didn't squirt , but her juices were thick and creamy ".
I got on my knees and began licking up and down her slit , when I licked her puckered hole she went ballistic , it took all my strength to hold her in place .
" Keep fucking still or I'm going to hurt you , and afterwards I'll still do what I want ,so just lay back and enjoy yourself ".
I kept on licking her , I stroked her clit , I slipped a finger inside he for a few minutes and then added another " .
She was screaming through the ring gag , she tried pulling away , she had no chance of moving much ,
I hooked my finger's inside her and found her G spot , she struggled even harder .
I reached up the bed and slapped her head across the face .
" Told you to keep fucking still if you move again I'm going to use my belt on you " .
Emily stopped moving , I was rock hard , and she was getting wet , I started pumping my finger's , I licked her clit .
" Oh yeah Emily , your ready to be fucked now ".
I pressed my cock against her opening , she was tight but not as tight as Anna ..
I reached up and pulled off her blindfold .
" I want to see the look on your face as I fuck you , if you close your eye's I'll fuck you tight asshole instead ".
If looks could kill I'd be dead ,
" Are you ready for this , I think you might enjoy it " .
I thrust forwards without warning her , my cock head hit her cervix , I wish I hadn't gagged her because her screams would have been music to my ear's .
I kept ramming inside I slapped her face .
" Squeeze me , I want to feel every inch of your insides " .
She began shaking her head side to side , her body was trembling , I pushed a finger inside her asshole , I could feel my cock through the small membrane that kept her two holes separate .
I pulled a fully ,then rammed back inside , spittle shot out of her mouth like a fountain .

"You'd better fucking cum for me , or I can fuck you all day , maybe that what you want and I'm more than ready to oblige you".
I began pinching her clit , muffled moans came out of the gag ..
" What was that , you want it harder ".
She shook her head side to side , I started rabbit fucking her , she moaned and groaned , but she was now dripping wet .

" Are you ready to cum yet , or do you think you'll find it easier If I fucked your asshole instead " .

Emily started pushing up as my cock went in deeper..
" That's it Emily work for your climax ".
I kept up the pace , continually rubbing her clit , and pressing my thumb against her tiny puckered rosebud , the more pressure I pushed my the the more she reacted .
" Oh yeah Emily I think you really enjoy that don't you ? ".
I was close to cumming but I wanted her to cum with me , I clenched the cheeks of my ass ,then pulled out , I moved up to her head and turned her to face me then rammed my cock until it breached her throat and then erupted , I held her head until she had no option but to swallow or choke , she swallowed , when I was sure she taken all my cum I pulled out ..
" Emily I can do this all night until you cum with me ".
I moved to the bottom of the bed and continued fucking her hard .
Suddenly she moaned out of the gag , then I felt a rush of her warm cum dripping all over my cock , I gave her my second load inside her , it felt fantastic .
" Use your pussy lips to clean my cock , or it's going back in your throat " .
Her pussy lips clenched around my cock , I bet she would have felt every inch as my cock slipped out of her pussy .
I got up and looked down at her , my cum was dripping out of her and down the inside of her leg's , some made it down in between her ass cheeks .
I removed the ring gag .
" You enjoyed that didn't you , well you won't be disappointed , we have plenty of time to fuck again , maybe I'll do your asshole , now go get cleaned up and make sure you do a good job " .
She move her legs over the side of the bed and then crawled on all fours to the bathroom , I heard her throwing up , coughing and spluttering , I heard her sobbing , then heard the shower turned on .

I was laying on the bed still naked , my back against the headboard , a cigarette in my mouth blowing smoke rings when she came back in ..

" I don't fucking smoke in here , you've had what you wanted so fucking go and bring my daughter back home ".

I Laughed at her ." Your not smoking in your bedroom babe , I am ,, and don't think I've done with you yet , I have so many plans for you over the next couple of day's ,and don't forget Anna , what happens to get depends on how nice you are to me , and how you behave , get that into your thick head , obey me and Anna will be safe ".
" You'll pay for this you fucking pervert , I swear you'll. " ..... She didn't finish the sentence , I was up before she knew it I'd punched her hard in the stomach , she doubled up and fell to her knee's , I grabbed hold of a fist full of her hair and forced her to look up at me .

" Do you really think you're in the position to threaten me , one phone call from me and your dear Anna will be in her hand's and knee's , a cock in her mouth and another inside her asshole , until I tell my friends to stop , so you had better apologise to me and beg me to fuck you anytime any any hole I want understand ".

" Ok ok , I'm sorry , just don't hurt Anna I'm sure you have put her through enough already , I'll behave ".

" That's better now go downstairs and find me a good strong drink and bring two glasses with you , and don't even think of running ".

She returned a few minutes later with a bottle of Hennessey and two glasses .
" Come and sit on the bed next to me and pour two large glasses , let's celebrate out new found friendship "
" I don't drink , I'm on medication it makes me light headed " .
" I'm not asking you Emily , I'm telling you , and if it makes you light headed then you probably won't feel it so bad when I fuck your ass ".

" Please you can't , it hurt when you just fucked me , you'll rip me apart if you try to put it in there " .

" Emily my cock will be going in your ass , in fact if you really care about Anna you will help me to enjoy the experience , now drink up , I want you to do something else for me , you might even enjoy it " .

I watched Emily drink , when she finished I poured her another .
" I don't feel to good , I feel dizzy " .
" Emily , I'm going to fuck you in your ass but first I need to prepare you , Anna was a good girl , she knew what I going to do , she didn't bitch about it like you , I watched Anna get herself wet using her vibrator , then I lubed her up , I lay on my back , Anna straddled me , she lined herself up and lowered herself , she had total control , and to be honest I think she enjoyed it , she coin three times before she'd finished and then she sucked me clean "
Emily, cursed me , cakes me all the names under the sun .
Her words were slurred but I made out what she was saying .
" You will never get me to do the same , I'd rather die , ".
" Emily I'm not going to make it that easy for you , your going to be screaming , your going to beg me to let you ride my cock , but it won't happen , I won't be lubing you up ,I'm going to rape the shit out of you , and not just once , then your going to choke on my cock in between , your going to be on all fours just like a bitch in heat , your going to be sorry for not behaving like Anna did ".

Emily was drunk , " I don't care what you do , I want Anna home , your a fucking sicko , your scum , a nobody , no wonder you can't get a girl , your kicking pathetic , now go and get my daughter ".

I just smiled at her , picked her up and placed her on the bed face down , her ass up , I pulled her wrists down to her ankles and handcuffed them in place .
I lifted her head and squeezed her cheeks together ,

" Your going to get me nice and wet , if I feel teeth I swear I will pull them out one by one " .
She giggled " So your a dentist as well
as a perverted rapist , will you give them a good clean as well "

"You won't be laughing for long bitch "
I rammed deep into her throat , I held her against me tight I fucked her throat like a man possessed until I fill her with cum .

" She laughed again , you suffer from premature ejaculation as well and you don't even have a decent load , I feel so sorry for you loser , now give me another drink ".

I pulled out of her mouth , moved behind her spread her ass cheeks wide apart as far as I could , I looked down , it was going to hurt me , but It would be excruciating painful for her ..
Without any warning I rammed inside her I felt her anal tract stretch apart , my ball's slapping against her ,

" Àaaaiiiiiiieeee , Oh God what are you doing , your sick ".
I pulled all the way out , then rammed back deep inside her .

" Take it you fucking slut ".
I must have been fucking her for at least twenty minutes , pulling out and ramming back in , her ass was a gaping hole , I pulled out , grabbed the biggest vibrator I had and rammed inside her pussy then began fucking her again .

Suddenly she screamed out .
" Oh God , I'm going to cum , ".
I couldn't believe it , she was loving it , I wanted to hurt her make her scream out in agony "
"Oh no your bitch ".
I pulled out , I was going to make her pay .
I got the bottle of Hennessey and poured what was left in my glass .
" Let's see if you like this " .
I thrust the bottle inside until the base of the bottle was lodged in her ass .
And how she screamed , the screams bounced off the wall's , she tried to crawl away , I watched as the handcuffs dug into her skin "
" Your not laughing now are you bitch and this is just the beginning .
I lifted her head and opened her mouth wide apart .
" Lick your suit off my cock slut ".
once again I shot my load down her throat.
I let her thrash about on the bed until she climaxed then passed out .
I sat down totally exhausted , had a drink and a cigarette , I must have fallen asleep.

Emily was awake and trying to get free pulling and tugging at the handcuffs .

" You'll hurt yourself if you keep doing that , I hope you had a nice sleep , I've been waiting for you to wake" .
" Let me free now you've done what you wanted , now bring my daughter home ".

I got up and walked up to her , and stood by the bed , I picked her up and put her on the floor , her ass was resting on her ankles.
" Stop , take off the cuffs they are digging into me "
I pulled her hair so she was looking up at me .
" You passed out before I finished with you , my cock needs cleaning it covered in your filth "

As she started to protest I shoved my cock down her throat .
" Make it nice and clean , because your going to do what I wanted ".
I dumped a load of cum down her throat and then pulled out ".

" You fucking bastard , your cock was in my ass , I did what you wanted ,you wanted my ass and you've had it "

" No Emily , I wanted you to ride my cock just like Anna did for me ".

" No No , Never " .
" Ok baby you give me no choice , I'll just give my friend's a quick call , I'll let you listen to her screams , then maybe you might change your mind ".

" No No I'm I'll do it then can I see Anna ?
" Yeah do it and I promise you will see Anna tomorrow ".

I took of the handcuffs and without any ceremony I pulled the vibrator and bottle out of her pussy and asshole .
She screamed out .
" Oh God you've ruined me , I feel strange " .

"Don't worry your asshole will soon be back to normal " .
" I need to clean up, I feel so dirty and used ".
" Ok yeah you do look a fucking mess and you stink "

About half an hour later she came back in the bedroom , she looked nervous .
" So what now , I'll do what you want , ".

" First I want you to get nice and wet , then I want you to get me nice and wet then you'll get on the bed , you'll straddle me , facing towards me , you'll keep looking at me , then you'll take my cock and fuck me using your asshole , you won't stop until you climax , when we're done ,you clean me , then you can get dressed and we can go and get Anna , if you don't please me and cum we'll start all over again ".

Emily couldn't wait to get it over with , she did exactly as I asked , she was like a wild cat as she bounced up and down my cock , she climaxed a couple of times ,when I spurted my load in her asshole , she pulled up , with great enthusiasm she sucked me dry.

" You can go get cleaned up and get dressed , and you'd better look fucking sexy for me I might want to stop somewhere , it's quite a long drive ".
Emily looked stunning after she had dressed , her hair hung over her shoulders , she had put make up on but hadn't gone over the top , she was wearing a lycra black skirt not too long and not to short , a cotton white blouse , the top three buttons open showing her cleavage , she was wearing sheer pantyhose , and black high heels .

" You look good Emily , a pleasure to the eye , I'd like to oblige you and give you a quick fuck ,unfortunately we bed to go ".
I was about an hour away from home , I pulled the car off the main road and turned up a dirt track , it would cut half an hour off the journey , I stopped after twenty minutes and pulled over ".

Emily looked at me .
" What are you stopping for "
I looked straight into her eye's , " I want you to suck me off for the last time , I want to feel myself in your throat , I want to watch you swallow my cum , when you've done that we can carry on , you will be seeing Anna in less than an hours time "

Emily sucked and licked me , I think she was giving me the best blow job she given , I looked down , her lipstick coating my cock , deeper Emily take it all ".
Ten minutes later I was ready to blow .
" When I cum , I want you to keep it in your mouth , I want to see you swallow it , I'm ".
I shot my load , her mouth was full ,cum leaked out from the side of her mouth .
" Look at me Emily , show me ".
Her mouth was full ,
" Ok swallow "
I watched it disappear , watch her throat gulping it down .
" I'm going to miss you doing that , and I bet you'll miss me doing it " .

I arrived home , pulled into the garage closing the rolling doors behind me .
Emily followed me into the house , upstairs and into the bedroom .
Anna saw me , she was naked , she ran up to me , " I've really missed you Sir , can we fuck , can I suck you off , you must be desperate like me "

Emily brushed past me .
Anna looked at her .
" Mom what are you doing here , how , when , I don't understand ".
" I'm taking you back home , I've done what this bastard made me do , we can go home , we have to put this all behind us , now hurry go and get dressed ".
When they were both dressed and ready I led them downstairs , follow me , I opened the living room door , they followed me in ..

" Emily looked at me , what the fuck is this , what's happening " .
Five men were sat in the living room ..

" Gentlemen please meet Emily and her daughter Anna , they can be purchased as a pair if you like , both are well trained , both have been anally broken in , they are both tight , and both of them can suck you dry ".

" What an I offered " .

I watched the stretched black limousine drive down the track leading to the freeway .
€ 155: 000 lined my pockets , I would miss Anna , but I was sure I'd find another toy soon .

The end of the story .
Hope you enjoyed it .
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Claire
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Joined: Mon Feb 24, 2025 7:21 am

Re: Anna my dear Anna. Amended Chapter One and Two Finished

Post by Claire »

@MadChris I cleaned up your posts a little. There was one post with only a single line and you made the final post a quote. I deleted the former and removed the quote from the latter.

Regarding the story itself: I didn't expect that ending. Are you planning a sequel?
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My stories: Claire's Cesspool of Sin. I'm always happy to receive a comment on my stories, even more so on an older one!