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"16 Inches? I QUIT!"

"16 Inches? I QUIT!"

Societal Decay Episode 2

Societal Decay Episode 2

OFFICIAL: The Most Vile Girl on the Internet

OFFICIAL: The Most Vile Girl on the Internet

OOPS! I Accidentally Sodomized You!

OOPS! I Accidentally Sodomized You!

Why You Motherfucker

Why You Motherfucker

Reverse Anal

Reverse Anal

Groups

Pole Position

0 Uploads · 57 Members · 0 Forum Posts · 36,712 Visitors
Fat dicks stretching cute assholes to their limit.

Gaping Assholes

397 Uploads · 92 Members · 3 Forum Posts · 28,297 Visitors
This group is spaicely for Woman's Assholes.gaping, opened and stretched wet Assholes.All kind of woman's buttholes are welcome.The wider the better.

Fist Me

350 Uploads · 56 Members · 0 Forum Posts · 19,039 Visitors
The reason we have fists is so that we can stretch with them pussies and assholes.girls fisting themselves or someone else fist them. using their hands feet and everything else that makes their holes gap.Girls holes only!

"Stretch My Little Asshole"

28,965 Uploads · 1,249 Members · 5 Forum Posts · 960,440 Visitors
Group dedicated to the hottest anal actions and the most delicious assholes. Let me help you explore your dirtiest anal addictions and desires

Feminized assholes

2 Uploads · 6 Members · 0 Forum Posts · 2,525 Visitors
Any male who has their asshole used and stretched made to look and feel just like a woman’s pussy. Shaved, waxed, bleached, loose and stretched gaping asshole that resemble a vagina with nice lips.

Board Posts

24
Anonymous
@confessions
27 May 2022 5:03AM
• 2,088 views • 0 attachments
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I'm a nympho who loves anal. I can't get get enough anal. Don't bother with my pussy, just shove your cock up my ass. I love gape and rosebud porn and I want nothing more than to be able to take a nice big fist in my own ass. But every time I find a guy willing to try HE chickens out when the stretch gets a little uncomfortable.

I'm sick of being babied. I want a guy to tie me up and gag me and work his damn fist into my ass whether I like it or not. To fuck me open relentlessly and slam his knuckles up against my asshole until it gives. And I don't just want to take his fist. I want him to ruin me for cock. I want him to punch his fist deep in my once-tight asshole and rip it back out. I want him to punchfuck me while I scream into the gag, sobbing and helpless. I want him to brutalize my hole until my rosebud spills out and then I want him to shove it back inside me with his fist.

I want my ass to just be a hole that swallows up anything it's given. I want a stranger in the street to be able to bend me over and shove a beer bottle right up there without any resistance. And I want to be that way because someone saw me for the dumb useless slut I really am and decided to use me the way I'm meant to be used.

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Anonymous
@confessions
29 Jun 2024 4:28AM
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ACCIDENTALLY INGESTED BREAST MILK - WTF?!
Last night I hooked up with this African chick, mid 20s, single mum. Quite big and with a massive ass, Kenyan ass to be specific and massive tits as well.
Overall it was an easy conquest, she was really really keen to meet up for a while. For a big girl with a kid her pussy was quite tight and she was extremely wet, to the point that as I was naked on top of her my cock slid inside of her with no assistance. 

I also ate her massive ass and made sure to tell her it was so big that I couldn’t breathe, she claims to have never done anal, however my tongue slid in very very easily and lightly gaped her.
If she’s being honest about no previous anal experiences, then I may have to visit her again and make her asshole acquainted with my cock, as it appears to stretch easily….

ANYWAY…
As we were making out, I went to suck on her tits, the first time around I felt a sweet taste and didn’t think much of it…thought it may have been a moisturiser or something…
However…the second time I went to suck on her tits I did so quite hard and felt a squirt on my tongue, same exact sweet taste…I then realised it was fucking milk bros…I thought what the FUCK?!

In all fairness…for all I know she’s fat enough to be incognito pregnant or something…not sure when the milk kicks in to be honest and her kid is like 4 I think…surely you’d stop producing milk after that long?

What I do know though is that immediately following the milk injection I really really struggled to cum, I was able to block that thought out for a bit and just get it done. But when post nut clarity kicked in…fuck man I was so grossed out, that shit made me want to vomit and I had to get out of there pronto…I can’t get the memory of the taste out of my head. 

What the fuck man…Has this happened to anyone else? How did you feel after the fact? Sometimes when I do weird shit im fought between disgust and hedonistic pleasure, but this time…fucking yuck bro 

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Anonymous
@confessions
08 Feb 2017 4:41PM
• 11,842 views • 2 attachments
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I confess that I lost my virginity to my first cousin and I want to fuck my sister. My cousin and I would watch porn that she stole form her dad at night, after my grandmother went to bed. Before long we were trying things from the porn on each other. She always kinda chubby but not too much and she was always pretty. Her pussy, ass, and tits are very nice. For a while, we just did oral stuff, I ate her pussy and licked her asshole and She would suck my dick, lick my balls and ass, she's great at it. I watched her go to the bathroom and other kinky things like that. But I did not penetrate her for a while. My cousin lived at my grandmas so we could only have our fun when I visited.

At home I was full of sexual frustration. I had to live with my beautiful sister who won't do things like that for me. it was like torture. I stole her dirty panties a lot and once jerked off over her while she slept in her room. The closest I got was one day during spring break in High School. Both parents were at work and I was sitting in the couch, just hanging out, around noon. She and I smoked weed together and she walked into the living room and asked if i wanted to burn, I said yes and followed her to the garage. She was a robe with pajama bottoms under it and her hair flipped up into a towel, she had just showered. After smoking and getting super faded, We return to the living room, I sit where I was and she curled up into a kind of ball to leave space for me to sit on the couch. I was turned on just sitting next to her.

"You can stretch out, put your feet in my lap" I told her. She kinda smirked and said, "really?" she kinda laughed. I reassured her and she put her feet up into my lap. After a while, I put my hands on her feet and started rubbing them. She look at me funny at first, but started to enjoy it. She let me do this a while, I got a boner while rubbing her feet and I felt like it was gonna rip outta my jeans. She fell asleep. I watched her sleep for a few minutes and whispered her name to make sure she was sleeping. She was, and I ran my hands down her leg and felt her inner thigh, she was so warm and smelled so good fresh outta the shower. I was so horney and I got carried away, I pulled my cok out and touched her feet with it. This is when she woke up and jumped up at the sight of my cock. She told me to put it away, she said we were brother and sister and that thats wrong. she said she wouldn't tell anyone but i shouldn't do that, she left the room. I went into my room and jerked off violently, I was kinda furious. It was rough for the next few weeks until I went back to my grandmas.

My next visit to grandmas, after the sister incident, I told my cousin that we need to fuck. She was reluctant but finally agreed. I got hard instantly, and was read to go, she pulled her pants down and I ate her pussy for like 2 seconds, just enough to get it wet and then shoved my dick in her beautiful pussy. This was the first time I was inside a pussy and It was magnificent, I waited so long and it was better than i ever though. She told me not to cum inside her, and I said I wouldn't, I didn't mean too, but It was so good. I couldn't pull out. I cam so hard inside her. We were afraid she would get pregnant but she never did, and we where way more careful after that.

Me and my cousins stopped having sex for many years, but started again about 3 years ago. Now, I live a lone and every few weekends she will come stay and we still have fun. I want to try to talk her into making some uploads for this site, Lets see how it goes.

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Anonymous
@confessions
18 Nov 2011 5:48PM
• 1,230 views • 1 attachment
[ − ] thread [ 8 replies ]

I confess that I fantasize about removing my wife's underwear in her sleep and placing some ants in her cunt.

The closest I got was:
One evening we had sex in our living room. she was on all fours, her face planted firmly in the sofa and her ass raised high up in the air, I was "keeping her busy" with my fingers when my eye caught a slow-flying mosquito. without thinking I reached out with my free hand and caught it, being careful not to kill it.

I then placed the stunned-wing-broken insect on her asshole and hoped it would bite. Alas the poor creature was too shocked and just wandered aimlessly, I stretched her cunt lips open and put it directly on her clit thinking maybe the blood-rich area will trigger the biting instinct.... nothing. At this point I saw she was starting to get suspicious so I gave up and just used my finger to rub and crash the poor thing on her clit until she came.

Attached some candid images of her that I took on another occasion.

http://www.imagebam.com/gallery/l10we51nqx1eo5fsff70awjbrvafwnv1/

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Anonymous
@confessions
16 Nov 2013 7:52PM
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I confess I let an older guy fuck me when I was 16.

When I was around 15, I started going on chat rooms and chatting with older guys. I was not and still do not consider myself gay, but when I get really horny I get in this depraved sense of mind. I'd get horny doing something I think is otherwise disgusting. Anyway, nothing got me hornier than knowing these older guys wanted to use my ass. I loved chatting with married guys because I knew they were paranoid about keeping it a secret like me. I had a lot of depraved convos with older guys about fucking my ass and making me their slutboi. I'd cum, always feel mega jackoff remorse, close the chat, and usually block them.

At some point I built up the courage to have phone sex with some guys. I would get older guys to give me their number and call it with *67 so they couldn't call me back. Pretty much whenever I was home alone I'd hit the chatrooms and find guys to phonefuck me. I was usually pretty shy on the phone, but I loved when a guy was really verbal and would call me names, faggot, etc, while we were moaning over the phone. We'd cum together moaning in extacy and hang up right after. Despite my post cum remorse, I would always go back. At times, when my family was asleep, I'd take my phone and a jizz napkin in the shed behind the house in the middle of the night to get off like this. I get both disgusted and horny thinking about moaning "fuck me harder daddy!" to some old guy states away, in middle of the night, in my filthy shed.

So now to the fucking: One day, I start chatting with an 50 something year old married guy and I don't quite exactly remember why, but we ended up jacking off together from time to time on messenger. He lived a few counties away from me, but in the same state. I don't think we ever phonefucked, but at one point he definitely convinced me to get a webcam, and I would cam for him. We had many horny conversations about him fucking me in front of his wife, etc. I'd always cum on cam for him and feel that remorse, I never showed him my face though.

We started having conversations about how we should meet and fuck, and it was always just jerkoff fodder. We were both to paranoid to actually do it. One weekend when the family was gone for the day we had a pretty long edging session early. We both were in an extremely horny state of mind I guess, because we decided to go for it. We stopped jerking off, our balls full with cum, to save for our depraved encounter. We worked out a plan were I would take a bus to a point where he would meet me and we'd walk to a motel nearby.

The moment I walked out of my house my heart was beating like crazy, but I felt hornier than I ever have. I'd never even taken the bus before, but my horniness made me so willing to do anything. When I go off the bus I saw the him wearing the clothes he described. He wasn't ugly, buy he was certainly a man in his fifties, a bit overweight and stocky. When I walked up to him, we were both very nervous and just said things like "are you ready for this" and "I cant wait." I started getting so horny as we walked, I started getting so horny though, and started thoughing his cock through his pants. Probably not the best idea since he was 50 something and I was young, but I was horny.

When we got in the motel room, my heart was pounding and my cock was throbbing. We took off our clothes and I lay on the bed naked. Keep in mind I was a complete virgin, only had a few fingers in my ass when I cammed for him, but was horny for cock. I had my first foreplay with this guy as we humped each other for a good 30 min. My cock was leaking at this point rubbing all over this hairy guy. We 69ed until I about burst and then gave him head while my cock softened a bit. I started pushing his cock on my tight asshole and we knew it was time.

He lubed up my ass with his fingers and slowly stretched me out a bit. It hurt and almost made me cum at the same time. He worked my ass with his fingers for a bit, until I told him to try to get inside me. He worked on a condom and dumped some more lube on his cock. I lay missionary while he started working his cock inside me. It was uncomfortable at first, but wasn't long before my cock was rock hard as his saggy balls slapped my ass. We started talking dirty. We didn't even know eachothers names. He moan "you like my cock boy!" and I responded, "fuck me daddy!"

He told me he loved me and I responded I love him too. I vividly remember this and making out while he fucked me. I confess my first kiss was this horny old man I met on messenger. He asked if he could take the condom off and I said fine. I didn't really understand how dumb that was at the time, but he was married I didn't think he had a std since he told me I was his first male fuck.

When he slid in me bareback, it felt so good. We kissed as he fucked me a few more minutes and then I told him I was gonna cum. A few strokes of my cock and I blew all over my chest and face with his cock still sliding in and out of me. Needless to say, I felt immediate disgust and discomfort. My cock got soft and I got quite but he just started pounding away harder. I'm not sure he fucked me harder because he saw I was uncomfortable and in pain and was trying to finish to get it over with for me or because the pain on my face made him hornier, but he pumped until he moaned "I'm gonna breed you boy!" Then stuck his tongue down my mouth while he pumped his seed deep inside me. He collapsed on top of me, his heart beating through me.

After a min or so he slid his beating semi out of my hole and just started cleaning himself up and getting dressed. I followed and there were few words after and we didn't look at eachother. We pretty much just dressed and I walked alone to the bus stop feeling dirty.

I blocked him when I got home and we never talked again.

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Anonymous
@chicks
26 Feb 2020 11:54AM
• 226 views • 1 attachment
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Stretch my asshole and fill me with piss please :)

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xDuckSick
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@random
27 Feb 2017 1:49PM
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Bernard's Cock

This is the confessional story of how Bernard was able to fuck whoever he wanted in class.

Bernard was timid and shy, and his thin body reflected this. However, as is often the case with such a person, he was the horniest of fuckers. Losing his virginity permeated his thoughts throughout every minute of his waking life, and when he slept, well, needless to say all his dreams had a common theme. Every morning Bernard awoke to the disappointment that the cunt he thought he'd finally been penetrating, was just another dream, and that in fact all he had achieved in doing was to make his pyjamas wet and sticky about the groin area again.

Eighteen and the closest he'd been to fucking was in his dreams. However, an unearthly gift was about to change all this.


The first time it happened, Bernard was in Math class. Sitting absentmindedly as ever, Bernard would alternate his gaze between the clock on the wall, and the view out the window. The girls were playing volleyball in the playground. He would try not to stare at them for too long, firstly so that he wasn't caught, and secondly so that he wouldn't get an erection in class. Every time one of the girls would jump to shoot, he would narrow his vision at their vest covered breasts, some were larger than others, but all gave him equal delight.

Turning his attention back to his text book, Bernard couldn't help but notice the pink thong of the girl in the desk in front of his. She was Jessica Riley, and she was the prettiest of things. Seeing her thong from behind, Bernard couldn't help but imagine what the front would look like, how she would look with nothing but the thong on, with her long brunette hair resting on her naked shoulders. How he would love to pull her thong to oneside and taste her fresh pussy, how her body would writhe under the influence of his tongue up her cunt. Bernard's breaths begin to become shorter when all at once his thoughts were suddenly broken.

Mrs Adams was standing over his desk. "Distracted by something again Bernard?", she enquired in harsh tones.
"No Mrs, sorry Mrs", fell the words out of his embarrassed red face.

Leaning forward, Mrs Adams continued to lecture Bernard on the importance of remaining focused in class and studying well. However it fell on dead ears, Bernard had already been distracted by her low cut top, draping off her shoulders, exposing first her collar bones, then her well defined cleavage. Bernard tried to retain eye contact with Mrs Adams, tried to look as if he was paying attention to her words. It was too dificult. He Intermittently nodded to simulate agreement with what she was saying, however this was merely an excuse to catch a glimpse down her blouse.

Seeing the top of her black lace bra, remembering the sight of Jessica's pink thong. Imagining Mrs Adams and Jessica naked together, rubbing each others bodies, kissing each others lips. Picturing them on their knees under his desk, pulling down his trousers, seeing their astonished faces as he reveals his gigantic cock (it wasn't). Bernard could no longer suppress the feeling in his boxers, a bead of sweat rolled down his face, and his cock all of a sudden was erect.

As instantaneously as Bernard's cock was hard, Mrs Adams speech wash frozen. He looked up awaiting the next sentence but it didn't come. He looked around, no one was moving. He looked out the window, the girls had stopped playing volleyball, frozen like statues in their sporting poses. Finally he looked back at the clock on the wall, it ticked no longer. In total shock, Bernard rose from his seat. Shaking like a leaf he reached out to touch Mrs Adams' arm. It was warm and soft, she remained totally motionless and unaffected.

The distress evident on Bernard's face slowly faded as his parted lips transformed into a wry grin. The realisation time was frozen and his cock was rock solid made Bernard overwhelmed with a strange blend of fear and joy. Building in confidence, he reached for Mrs Adams' tits, the first non-maternal pair he'd ever felt. He squeezed them with delight. In the blink of an eye he had removed her blouse, and then - not without difficulty - removed that seductive lace bra, dropped it to the floor, and almost awe struck eye-balled her large exposed tits. Those grand orbs of desire, framed and enhanced by a thin waist and slender shoulders. Bernard was beside himself.

Removing his own top, Bernard moved closer to Mrs Adams. He threw his arms around her waist tightly to feel her naked torso against his. He tasted her lips, slid his hands down her trousers and groped her firm ass cheeks. After feeling her tongue with his own one, he moved down to kiss her neck, in doing so he saw it again - over Mrs Adams' shoulder - the pink thong of Jessica Riley.

How had he forgotten about Jessy, sitting there, bent forward, frozen. He stepped away from Mrs Adam's body, approached Jessica's desk. She sat there with the end of a pencil in her mouth. How innocent she looked clearly deliberating on one of the problems from class. Bernard was transfixed by her pretty frozen face, by her soft lips teasing the end of that pencil, he couldn't resist any longer. Her head was at a perfect height, he turned it towards his crotch and dropped his trousers. He ripped off his boxers and manually opened her mouth, then - slowly yet purposefully - buried his throbbing cock in her gob. He felt her wet tongue before the back of her mouth.

His heart beating like a drum, Bernard lost all self-control. Taking hold of her head with both hands, Bernard begin thrusting in and out of her mouth. The silence in the room was broken by the sound of squelching and of Bernard's balls ricocheting off her chin. Jessica's mouth became ever fuller with spit and bile as she began to gag on Bernards cock which gave him a shock. He took his cock out her mouth to see if she had awoken. She hadn't, but moreover, she was more beautiful than ever. Frozen in time with saliva hanging between her mouth and his cock, her eye make-up a mess.

Bernard lifted Jessica out of her chair. Fortunately she stood of her own accord. Starting from the top down, Bernard unbuttoned her shirt one by one. She didn't wear a bra, and her perky budding tits were a sight to behold. Small, unassuming, fucking perfect. Her body was just as Bernard had imagined. Petite as anything, slightly tanned, soft, delicate, ripe.

Bernard continued to strip both his mannequinesque beauties completely bear. He looked around the room at all the other frozen faces, but with little inspection was sure he already had the two finest women in the room stripped naked, ready at his disposal. He pushed Mrs Adam's onto his desk face up, and positioned her body so that her head dangled off the end. With some effort and plenty of huffing and puffing, he lifted Jessica's body on top of Mrs Adams' the other way around and on all fours, so that her hairless pussy rested right above Mrs' Adams' upside down face.

Bernard stood back and admired his perfect fucking creation. Proudly he stood up to it, kissed Jessica's pretty little ass cheek (for it looked so sweet), then angled his cock down towards Mrs Adams' mouth. He secured the two bodies in place with his hands, and begin to pummel her mouth like a rabid dog fucks their favourite toy.

Once again the room was full of the sound of gagging. This time Mrs Adams' mouth squelching whilst spit spluttered out all over her face. Bernard stopped fucking her face for a moment, again admiring his creation and the mess he'd made of it.

Using his hand, he cupped up some of the saliva from his cock and Mrs Adams' messy face, and dribbled it over Jessica's ass. Bernard returned his cock to Mrs Adam's throat, burying his whole length in there as far is he could go, holding it there for a few seconds so to lube up his cock. He pulled it out again, took a firm grip of Jessica's hips, and with some force required, squeezed his cock into her asshole.

Her asshole, tight as it was, gradually parted, expended, and engulfed the head of Bernard's cock. He slid inch after inch, deeper and deeper into her shitter, and as he reached maximum penetration, she wimpered.

Again Bernard feared she had awoken. He reached forward and turned her head to face him. It was still motionless, yet now it bore an expression of discomfort. Still angling her face towards him, Bernard removed all but the head of his cock from her ass. Staring deeply into her eyes (still beautifully framed by her messed up makeup), he slammed his cock hard up her ass to the sound of flesh slapping flesh and another whimper. Certainly she was still frozen in time, but to Bernard' delight, she quietly whimpered as he continued to pound her ass.

After a few minutes of fucking Jessica's pretty little ass, he removed his cock, and spat onto her barely gaping hole. It slid over her asshole, down the ravine between her red ass cheeks towards her pussy, before dripping on Mrs Adams' face. The sight of this excited Bernard immensely, and joyfully he returned his ass stenching cock to Mrs Adams' throat.

He pounded away gleefully, alternating between the teachers gob and the students asshole, the messier Mrs Adams' face became, and the more Jessica whimpered, the more Bernard became excited. Frantically he fucked both of them until he felt a contortion in his stomach. Uncontrollably, as if possessed, he stretched Jessica's ass cheeks wide apart, found her drenched wet cunt with the head of his cock, plunged the whole thing in, and instantly erupted. With a demonic grunt, the likes of which Bernard did not know he could produce, Bernard was finished.


So that's the story of how Bernard lost his virginity (if you can call it that). After cumming (and taking a moment to watch his cum spew out of Jessica's pussy onto Mrs Adams' face) he quickly cleaned and dressed the pair, and soon as his cock was soft again, the clock ticked again. Needless to say Jessica and Mrs Adams' were might confused as to why their makeup had suddenly became a mess, why Jessica's ass was sore, and why Mrs Adams' had lost her voice. However it remained an unsolved mystery.

From that day onwards, whenever Bernard got an erection, time froze. Might this gift turn out to be a curse for our timid Bernard. Who knows? All Bernard knows, is that he had the best fucking experience of his life, one that he couldn't have even dreamed off without his magic cock.

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Anonymous
@chicks
24 May 2025 8:47AM
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Let’s see some of those nasty sluts stretching out that pussy and asshole..🔥🔥

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Slut_girl69
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@confessions
02 Feb 2025 7:23PM
• 241 views • 3 attachments
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Another session of my humiliation and stretching my anus with improvised objects. If only my asshole was stretched in front of the owner

Your young slut
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Anonymous
@confessions
25 Feb 2009 6:00AM
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I confess that I love to see women give birth!! When my wife pooped out our daughter she was lying on her side and I had one of her legs pushed back so everything was in full view. I loved seeing her little hairy pussy slowly stretching and there was nothing she could do to stop it. Her asshole really gaped as she pushed. Would have loved to fucked her ass real good as she was pushing and I was watching her pussy slowly stretch! I keep replaying this scene over and over and jerk off regularly to it. She was so sexy all spread open with her holes all stretched! Also jerk off to lots of birth vids on the net. Anyone else love to do this?

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Anonymous
@random
08 Dec 2016 8:32PM
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How It Started 3 1 and 2 were posted earlier
After Jack left I jumped up and got in the shower. It was Saturday and I didn’t have to work until Monday. I thought I had better hurry before Jack gets impatient and starts to get angry. I had grabbed a razor and some shaving cream before I got in the shower. I have been shaving my private areas for a couple of month now. I didn’t have very thick hair on my arms or legs and I had never had much facial hair. I only shaved maybe once a week and only because it looked straggly. I shaved my legs and what few hairs I had on my chest. I made sure my ass and front side was smooth. The plug was still in my ass when I got ready to shave there so, I had to pull it out, shave and then put it back in. My body felt strange when I got out of the shower. It was cool and tingly. I went to the mirror and started doing my hair. I was trying to curl it while I was blow drying it and it sound funny but, it was looking pretty good. I put on some make up to help me look more like a girl. When I got done I went to get something to wear. I didn’t have a lot of clothes to wear. Mostly what I had were panties, sleepwear, and a couple outfits. I never needed much because I only wore them in my room. I put on a thong and found a pair of shorts that were really tight and short. I remembered I had bought a halter top when I bought those shorts. Then I heard Jack say “Come on Sue. We don’t have all fucking day.” He was mad, so I hurried up and put on the shirt I had on last night and tied it over my stomach. Then I thought “OH FUCK. I had forgotten my chastity device.” I got it out of the drawer and put it on my dick. I clicked the lock and didn’t know what to do with the key. I stuck it in my pocket and ran downstairs.
When I got downstairs, Jack was in the kitchen. I said “I’m sorry for taking too long.” Jack looked me up and down. He said “You are worse than a woman. Did you wear everything I told you to?” I nodded yes. “Well let’s see.” He replied. I unbuttoned the front of my shorts and turned around. I pulled them down over my ass and bent over. I reached back and spread my ass cheeks so, he could see the pink jewel on the end of the plug. He walked over and rubbed my ass. Jack grabbed the end of the plug and started to pull it out. The fat part the plug slipped out of my ass and he pushed it back in. I moaned when he did it. Jack said “You like that sissy don’t you. Now turn around and show me what else you got on.” I stood up and turned around. He snickered when he saw the lock and said “That’s nice. Where’s the key?” I reached down and got the key out of my pocket. I handed it to him with my hand shaking so much I almost dropped it. Jack said “Is that the only one?” I nodded yes and Jack smacked me a crossed my face hard. He said “Don’t lie to me. Is this the only key?” My eyes watered up as I shook my head no. He told me to go get the rest of them. I ran to my room and got the other two keys. I went back to the kitchen to where Jack was standing and put my hand out with the keys. He took the keys and said “This better be all of them or you will be sorry.” I blurted out “I’m already sorry.” And he just laughed.
“Come on Sue.” He said “Were going for a ride.” My eyes got wide with fear. I had never been out of the house dressed like this. I said “Please Jack no. I don’t want to leave. I’ll be good and do anything you want. Just don’t make me be seen like this.” Jack said “It will be ok. You look great and where we’re going nobody will see you.” I was kind of flattered that he thought I looked good but, was scared of where he was taking me. He grabbed my arm and started pulling me towards the door. We got to the driveway and he told me to get in his truck. I got in the passenger side and he started to back out when he said “Slide over here next to me.” I slid over and it looked like I was his girlfriend on a date. We didn’t drive far before he was reaching in his pants and pulling his cock out. I looked down and knew what he wanted me to do. I slid down the seat and turned so that I was facing his lap. I lowered my mouth until it was just above his cock and he pushed the back of my head down on his cock. I bobbed my head up and down sucking him. We were going down the highway with me sucking him the best I could when I heard a horn blow. I never stopped but Jack laughed and said “I think the truckers like you. Get back on the seat with your knees pulled up.” I never stopped sucking his cock as I climbed back on the seat and put my knees under my body. My mouth was on his cock and my ass was up pointing towards the passenger window. I didn’t look back not wanting to see who was going to see me. Jack told me to take my shorts and thong off. I shook my head no with his cock in my mouth. He grabbed the hair on the back of my head and shoved me down until his cock was all the way down my throat. I couldn’t breathe this way and he knew it. Then Jack said “Do it and I will let go.” I couldn’t get my shorts off fast enough and when I did he released my hair. Now my ass was bare and facing the window for everybody to see. Jack loved it. He would speed up to catch some trucks and then slow down when we were beside them. He did this a couple of times and then told me to reach back and pull my plug out. I did as I was told and the he said “Start fucking your ass with that thing until I tell you to stop.” The plug would stretch my asshole when the fat part went in and out. I was still sucking his cock and every time the large part would pass though me, I would be forced to take a deep breath causing me to suck him deeper in to my throat. He rolled the window down and I could hear horns blowing and I thought I heard people hollering something. This went on for a while and then Jack rolled the window up. He told me to sit up and put my shorts back on.
I got turned around and when I looked up I saw that we were pulling into a mall parking lot. I was scared as hell, not knowing what Jack was doing. He said “We are going shopping. You need some new things to wear.” I was scared. I had never been in public dressed as a girl. I had fantasized about it but, never had the courage to do it. He parked the truck and got out and said “Come on lets go.” I just sat there and refused to get out and Jack said “Sue, you better do what I say or I will take you to that truck stop on the highway and let all the truckers that you just flashed fuck you until can’t walk!” I knew I had to do what he said so; I got out and walked into the mall with him holding my arm really tight. Our first stop was Victoria Secrets. Jack was picking up lacy thongs and sleepwear. Then he turns and said “You need some bras. What size do we get? Double A-.” and laughed. He called a sales woman over and asked where they kept the bras that would fit his girlfriend. It was funny I almost smiled when I thought about him calling me his girlfriend. She pointed to the area of the store to go. He found some bras that were for flat cheated women. He handed me several and then he saw the garter and stocking. He like them and grabbed a few of them. My arms were full of things and he walked me to the checkout. I put the stuff on the counter and the girl scanned them. It was over $400 of stuff. I looked at Jack and he bent down and whispered to me “You better get your credit card out before I start sending your pics to my friends.” I paid for the thing and we left the store. The rest of the day was more of the same. We want into a lot of store and bought more clothes. Everything he picked out was slutty clothes that a prostitute might wear. He even made me but heels and boots at a shoe store.
We were walking down the mall and I was amazed that all day nobody seemed to know I was a guy. I even had seen a few guys checking me out like I was girl. Then all of a sudden I saw a group of guys that I had seen before. They were friends of Jack and John for the gym or the bars. I never looked up and just walked by them. Jack stopped to talk to them. I walked down the mall and thought I better stop and wait. After a few minutes Jack walked up and grabbed the back of my neck and said “Don’t you ever walk away from me? You should have stopped and chatted with the guys that will be fucking you soon!” I didn’t know what to say but, “I’m sorry” Was he really going to make me fuck all his friends? Maybe he was just threatening me. Then he said “You owe me for that and I know how make you pay.” I guess we were done at the mall because he led me out to his truck and we started to drive.
We drove for awhile to a place I was not familiar with. It was a part of town that was run down and an area that most normal people go. There were vacant building everywhere and a few people that looked like they were wondering around. Jack pulled the truck over and said “Get out! I want you to get out of the truck and walk down this street. I’ll pick you up in three blocks if you make it that far. All you got to do is anyone you pass you got to ask them if you can suck their cock! If they want you to you got to go with them and do as they say. Suck them; fuck them or whatever it takes to get them to cum on or in you.” I panicked and pleaded Jack not to make me do this. I told him I would do anything he asked just please take me home. He said “Tell me what you will do to make this not happen.” I started blurting out that I would suck his cock anytime he wanted and he could fuck my ass as often as he liked and I would be a good slut for him. He said “OK only two blocks then.” I screamed “NOOO, I’ll dress like a whore and you can show me off to anybody you like. I will act like a slut and you can take me anywhere you want and show me off to your friends.” Jack said “Just one block unless you got more to offer.” I thought and then whimpered “I will suck and fuck all of you friends and I will be your whore to use. Please don’t make me walk down this street.”
Jack said that he would agree to this if I proved that I was a good whore. He said “Pick someone on this street and suck their cock and we could go home.” I didn’t have a choice and it was better than having to walk three blocks and have sex with everyone on the street. I looked around and pointed to an old bum that was sleeping in a doorway. I figured he probably not interested. Jack pulled the truck next to the doorway and rolled down my window. Jack said “Go ahead and ask him.” I called out to the man and he just grunted. I yelled again and he rolled over and I seen his face. In the doorway he was all balled up but, when he looked up I saw he was a black man. “Tell him” Jack said. I said “Sir, Do you want me to suck your dick? I will if you want me too. He got up and started to walk towards the truck and Jack said “Show him your ass.” I turned around and put my ass up toward the window. I pulled my shorts down over my ass just as he got to the truck window. He was looking at my ass and Jack asked him if he wanted to get in. I heard the door open and I moved over to let him in. He got in the truck without saying anything. Jack said “Ask him again.” I asked him if he wanted me to suck his cock and then he started reaching in his pants. He unbuttoned and unzipped his pants and pulled out the biggest fucking cock I had ever seen. Jack started laughing and said “Good choice Sue.” His cock looked more like an arm than a cock. It was at least a foot long and as big around as a beer bottle. I knew there was no way I could suck his dick. Jack started to drive and told me to get busy. I crawled down to the floor in between the bums legs and put my face in front of his cock. I reached to the side of the seat and moved it as far back as it would go. This gave me room to move around and kneel in front of him. He smelled terrible. He smelled like burnt wood and strong body odor. I started licking his cock and it tasted just as bad as it smelled. I tried spitting on it a lot to help the taste, but it only helped a little bit. He was getting hard and thank god it didn’t get much bigger. I was licking up and down his cock and he was moaning. I put the head of his cock and tried to take him in my mouth. I was only able to get a couple of inches in and my mouth was full. Jack must have thought I wasn’t trying hard enough because he grabbed the back of my head and started pushing me down. Even with him pushing, it wouldn’t go down my throat. I only had less than half of his cock in me. The bum was starting to breathe heavy and was moaning. Jack pulled my head back and said “Not to fast Sue. Don’t make him cum yet. I want to see how much of that monster you can take in your sissy ass.” I pleaded with Jack not to make me do that. I knew his cock would hurt me and probably give me some sort of STD. Jack didn’t want to hear it. “We can go back and you can fuck all the men in that area if you want.” Jack said. I told him that I didn’t want to do that either. He said “It your choice.” I knew I would lose. I lost the last night. I lost this morning and I’m going to lose now.
I got up without saying a word or looking at either one of them I got up and pulled down my shorts and thong down. Jack said “Bend over and let your lover pull that thing out of your ass.” I leaned towards Jack and put my ass up towards the bum. He looked at my ass for a while with a confused look on his face. Then I thought “Oh fuck, he thought I was a girl.” He reached out and touched my ass and I cringed. He spread my ass cheeks and was looking at my bottom with a pink jewel in it. He grabbed the plug and started pulling like he didn’t knew what it was. He kept pulling harder watching my ass stretch around it until in came out. He looked at the plug and then I saw him put it his pocket. I remember thinking it was kind of funny. He must have thought the jewel was worth something. I got back up and moved until I was sitting on his lap. I rose up until I could point his cock at my asshole. I sat back down and started putting pressure on it to push it in. It felt like I was sitting on a pole. It wasn’t going in at all. I pushed back as hard as I could and it never went in anymore. I looked at Jack and said “It’s not going to fit.” Jack told me to look in the glove box. I opened it and saw some condoms and some gel. I grabbed the condoms and Jack hollered “No slut, use the gel.” I squirted some of the gel on my hand and reached back to put it on his cock. I thought I better use a lot and put more in my hand to spread on my asshole. I got back up and put his cock back to the entrance of my ass and pushed. “OH FUCK” I squealed. Only the head of his cock went in me. It felt so big and burned as my ass tried to stretch around it. It still only went in an inch or so and stopped. I would push back but, my ass won’t open for it.
Then all of a sudden we hit a big bump in the road. The jolt slammed me down on his cock and another couple of inches went in me. I screamed like I stabbed and was not able to breathe. The pain was terrible. I was trying to maintain my balance while I got used to the size of his cock. Jack saw what the bump did and must have got an idea. He started giving the truck gas which pushed my back towards the bum’s cock. Then he would slow up and then give the truck gas again. This made me moved back and forth on the bum’s cock. Another inch slide in me and I was holding on the dash trying to control. All of a sudden Jack turned down a street and I recognized the area. We were back at the mall. I thought “Oh no, everybody was going to see me.” That was not why Jack came here. The mall was big and had a road that circled it. When we hit the first speed bump I knew why Jack came here. The bum’s cock slammed another inch in me. The mall road had a lot of big speed bumps on it to keep people from speeding. I was doing my best to hold on to keep control when Jack said “Put your hands on your head Sue.” I knew that meant there would be nothing stopping that cock from going all the way in me. I let go of the dash and put my hands on my head when the next bump hit. His cock slammed into me and I think I almost blacked out. I pushed with my legs trying to lift myself some and the next bump came. More and more of the bum’s cock was going deeper into my ass. The speed bumps seemed to be very close together and my legs were tired and I couldn’t lift myself anymore. Every bump pushed his cock farther in me. My ass didn’t hurt much now but, I felt a lot of pressure on my insides. My weight forcing down and the speed bumps slamming me on his cock must have pushed the bum over the edge. He grabbed me around the waist and pulled me down hard on his cock. I felt his cock drive deeper than ever and I felt his course hair rub against my ass. He was all the way inside me. My stomach felt like I had been punched in it. He grunted as he came in my ass and then he released me. I was too weak to lift myself off his cock and just sat there impale by his big cock.
Jack reached over and grabbed me by the arm and pulled me towards him. The bum’s cock was yanked out of my ass and Jack said “Funs over get the fuck out dirt bag. Get the fuck out.” The bum never said a word and just stuffed his cock into his pants and opened the truck door. As soon as he was out Jack sped off. He looked at me and said “What a slut you turned out to be. Time to go home sissy.”

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Do you like my asshole stretched?

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