Jennifer's Walk of Shame

Story Info
ENF has humiliating sexual morning with horny homeless men.
6.2k words
3.99
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112

Part 1 of the 2 part series

Updated 06/09/2023
Created 07/31/2019
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First story. Writing more already. The story is all fiction.

Trying to do a wild ENF theme. Feedback welcomed.

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Jennifer's Walk of Shame

"Uhhh where am I? Whoa wait. wait. what's going on. I was partying at the club. What the fuck. Where am I? I thought I was just dancing. Where are my girls?" Jennifer thinks this to herself as she opens her eyes and sits up from the ground.

"oh fuck it smells. What is this? Trash? ew more trash. oh my goodness, there's a homeless man next me." Jennifer wipes her eyes as she smells the stink of trash. She opens her eyes to find a middle aged homeless man next to her. Who was he? Why is he here? She was about to touch him when suddenly a different hand grabbed her shoulder. Jennifer squeals in surprise to find another bum standing behind her.

"Hey Tom! She's awake. Wake the fuck up!" The bum chucks a tin can at the sleeping man and hits him square in the head. He wakes up.

"oh what the hell! oh oh. hey sweet thing. you ready for some more? heh heh some more fun?" The bum wasted no time in creeping out Jennifer. She had no clue what he was talking about. She soon brought in her knees to kneel and stand. But when she wanted to stand up the older male was still holding her shoulder, keeping her kneeling on the ground.

"I don't know what this is. I don't want to know. I'm leaving. Bye guys." She tries to stand up again but no success. She looks up confused and timid at the standing man. When she turns back around to the first bum, there is a cock in her face. She how sudden he is a pervert. She can't believe there is a random cock in her face. Tom slaps his dick on her surprised face.

"okay lets get with it." Tom grabbed her nose and pushed his dick in her mouth. Of course it slides right in because she wanted to scream. "hey Dick, get the hands behind her back!"

Dick, the other bum, quickly gets both her wrists pinned to her back. She has big eyes and loud groans as the dick moves back and forth in her vulnerable mouth. Her mouth makes a pop noise as Tom pulls her off. He slaps her ass and turns her hand. As she gasp for air. there is another dick ready to fuck her mouth.

"Wait urrrrgh wait urrrggh please stop! ag ag." Jennifer could hardly talk as the homeless men took advantage.

Chapter 2

Jennifer thought to herself as a cock was sliding in and out of her mouth. "What the fuck is going on! Why am I here?! Why are dicks in my mouth! Oh my, it taste gross." She looks up at the bum with big confused eyes. She just woke up. It was too early for this shit.

The bum fucking Jennifer's mouth making eye contact and speaks to her. "Hey slut. My name is Dick, and my dick is in your mouth. How does it feel? oh wait, I don't care." And with that he grabbed Jennifer's head and banged her face back and forth on his swollen cock.

This went on for several minutes. Jennifer couldn't believe bums were face fucking her. They were forcing cocks down her throat and she couldn't understand why. She didn't understand why she was there with them in the first place. She just remembered clubbing and drinking with her friends. Tom again pops his dick out of her mouth and this gives Jennifer a chance to speak.

Jennifer quickly speaks. "Wait! Please! Stop! Why you doing this! Why me! Let me go!" Drool and cum fall out her mouth. She tries to catch her breath. She desperately wants some answers.

"What baby? You don't remember you protectors? well, do you remember last night?" Tom leans in to finally tell Jennifer a clue about last night. Jennifer shakes her head 'no' like a dumb little girl. She didn't remember this guy. Jennifer was scared and humiliated. She remembers being at a club with her girlfriends. They were drinking. She was drinking a lot...actually.

Tom "Okay, I'll recap with you slut. But you gotta keep our dicks hard with nice slow sucking. We won't pound our cocks in you mouth anymore. You can just keep sucking slowly for us. Now listen to the story, you dumb little cocksucker." Tom goes back to pushing her face on Dick's dick. She reluctantly opens her mouth and lets Dick slowly move her head up and down his cock.

"Well we found you this way miss. You were sucking dick when we came by this way. You were sucking fierce too. Ass hanging out. Drool down your lips. A real cock sucking display. It was two guys. You were sucking those two real good right here in the alley." Tom switches her face to start sucking his dick.

Jennifer tries to understand the bums story. She heard everything he said but still couldn't believe it. She thought, "What you mean I'm sucking two dicks? Who's dicks! Why was I sucking dick in the alley?" Jennifer is totally confused and embarrassed.

"oh fuck, you're a good cocksucker you know that. You were better last night though. wonder why." Tom looks down at Jennifer as she looks up. She's desperately listening to her story. She stays with pouty dick sucking lips as Tom moves her slowly face fucks her.

"Anyways, turns out your were sucking two other bums dicks. Because get this" He pauses with his dick fully in her mouth. "You thought they were bouncers, they said. You thought sucking dick would get you back in the club. oh oh oh yea like that." Tom passed Jennifer off to Dick again.

Jennifer taking in the new information as well as cock in her innocent mouth. She tries to understand the events of last night. Jennifer tries to think. "What?! I tried to suck dick to get in! Wait? I was kicked out. I must of been gone to get kicked out. oh fuck."

Dick holds her ponytail and slides her reluctant mouth over his cock. "But this is our spot. Right here. yes it is. yes it is. Our spot. And they were starting to slap you so we told them to get the fuck out and leave the booty here. Your fine ass booty."

Jennifer can't believe what's happening. Things escalated so quickly for her. She remembers hearing music from the club then as she now tries to swallow more of the bum's dick. She felt degraded to be there sucking them off. She wants to get home but didn't want to get hurt. She didn't know what these homeless men were capable of, so she gave in to their demands. She was frightened and still hated having to put their nasty cocks in her mouth.

As Jennifer was sucking dick with more pace since the guys stopped talking to her. Jennifer felt a hand slide across her ass, smack a round cheek, and pull up her short dress. Before she could even try to touch her own dress, her cheeks took another smack. Tom was holding her hands with a surprising firm grip. Jennifer couldn't shake lose. She could and did keep shaking her ass.

Then she felt hands flip her top down and expose her tits suddenly. She gasped. And shivered at all this nakedness. She was so embarrassed to be showing her ass and tits. She was grossed out to be here with bums. She was humiliated to be in a public alley exposing herself. Her groans hint at her displeasure. Jennifer could only make muffed moans as a dick stayed in her mouth while her tits and ass are exposed.

Jennifer was wearing a blue dress. It was a tight dress that hugged all her curves. She sways her ass in the club with it. Now it rest on top of her ass sitting besides some homeless men. Her ass cheeks are completely hanging out for anyone to see. The dress has a bustier of its own, like a corset. So Jennifer didn't wear a bra. When Tom yanked her the top down, the firmness of the bust just flipped down with no problem. It opened like a door to her round perky tits. Jennifer's tits bounce gloriously while the homeless men force fuck her mouth. Her skirt is raised completely up above her ass. Jennifer's body feels so dominated by these homeless men. She gets incredibly nervous to being nude in public.

Jennifer again screams while Tom's dick rams in an out of her mouth. She screams because Dick ran his finger over her ass, butt hole, and pussy lips. Jennifer realizes at this point that she has no panties on. She feels another wave of humiliation to know her ass and pussy are on naked display.

"Where are my panties!? Fuck! so much dick. In my mouth. My panties! oh my. I'm naked!" Jennifer tried to process what was going on while keeping up with the cock sucking demand. Lots of drool is running down her mouth now, with some on her tits. She knew she came to the club in a pink thong. Now, she had no clue where that thong was. She wished she had it on as Dick starts to rub his finger up and down some moist pussy lips. She shutters at the domination taking hold on her. Her slutty body being taken by homeless men. Jennifer doesn't want this to happen but can't will herself to stop it. She hates feeling this nasty strange man's finger rubbing her sensitive private area. She just wanted to be with her friends dancing, not here sucking some homeless mans cock.

Chapter 3

Suddenly, Jennifer is lifted up. A loud pop is heard when cock leaves Jennifers mouth. She can't believe how used she felt. Such a humiliating thing to happen to her.

Tom was taking a step back and spoke "Well babe, I think it is time..."

Jennifer feels the grasps on her wrist loosen up. Suddenly, she decides to fight back and push away these bums. She interrupts Tom and shoves them both back.

"Enough! Ok I'm done. No more! Back up! My mouth is so sore. Fuck you guys. Back up fuck heads." Jennifer attempts bravery. However, she did not realize that while yelling at the bums, she walked back into a corner in the alley. The bums were camping by a dumpster niche in the alley. It was space for three but only one was there now. Jennifer put her dumb self further in the corner. As Jennifer realizes the surrounding walls, it was too late. Tom and Dick rushed her fast and pin her face to the wall. She never had a chance.

Her front was to the wall as the two homeless men pinned the sexy brunette. Her young full round body showing in a blue tight dress was squirming to their pleasure. Tom was actually about to let her go. He was going to end it but then dumb Jennifer did a dumb thing. Now he wants to punish her. Get some more out of her ass.

"You dumb slut, that was a stupid move! Now your punished! Now your ass gets it!" RIP! More enraged this time and wanting to turn it up a bit on her, Tom grabs the center hem at the back of her skirt and rips it right about apart. He didn't stop until her whole ass was out. He splits the skirt with a long slit up the middle. It falls to the side, leaving a blue frame to a young vulnerable perky round ass cheeks.

"Hey! ouch! ok stop! Sorry! Hey not my dress! Hey! No no no! oh my! You ripped it! Please stop!" Jennifer's girlish pleads go unnoticed again. She didn't think it could get worse than waking up with bums and sucking their cocks. Well it would get worse for poor sweet Jennifer.

"Say you sorry bitch!" Slap! "Say it!" Slap slap. "Hey Dick come slap this ass too. She's got some cheeks on this one!" Slap slap! Squeeze.

Jennifer's ass takes a hard spanking from the two bums. They slap her ass and she tells them sorry sir, over and over again. Her feet dance back and forth and her legs shift as they palm her jiggling butt over and over again. Jennifer's ass reaches a nice red. Jennifer's tears have forced her mascara to run in little black streaks. With ass hanging out, glowing red, and ravished face Jennifer looked like a dumb slut.

"Ok! Are we done now! ow my ass! Please let me go! Let me go home. I'm sorry. Hey! what! stop!" Jennifer is pushed to bend over a stack of palettes. The same palettes that gave her some covering when sucking dick. Her dress falls to the sides exposing a glistening full red ass. And a puffy pussy.

"Tom walks in front of Jennifer's nervous face. She doesn't quite get whats going to happen yet. She's so flustered with her stinging ass. He grabs her ponytail and forces her to look up.

"Well since you went mean on us. Lets remind you of the good ol times we had last night then. shall we. cause we all had a nice time last night do this! maybe then you'll feel better. hm?" He smirks and stand up right to put his dick in Jennifer face.

"oh my! oh no! no! no no no! Please don't fuck! Please stop! please! ow! ow! ow! go easy! ow! hey! oh fuck! oh fuck! please! ow!" Jennifer screams out as Dick slides his cock in her waiting pussy. He wastes little time in pummeling her sweet spot. Her red ass bounces to a wonderful display for the bums and it stings terribly for Jennifer. She grunts and moans as Dick works his dick.

Soon Jennifer is sucking dick again and taking it hard from behind. Minutes go by in the waking sun as a dumb brunette slut is split roasted by a couple of homeless men. The bums fuck Jennifer good. And she can't believe how much energy they are showing. She was hoping this would end soon but they just kept fucking her. Jennifer was surprise to get such energy from two homeless men. They forced her to get on her hands and knees on top of the palettes. She does as told, and offers herself in a new position. Her knees and elbows are keeping her steady on the palettes. Jennifer's ass rounds out even more this way and exposes more leg. With an arch back and vulnerable round ass, Jennifer bit her lip as she looked behind her and in front of the two bums ready to fuck her some more. She knows she's on display but can't do anything about it. She kept hoping they would blow their load soon and let her leave. They pound away again on her pussy and in her mouth.

Throughout Jennifer's ordeal, bikers and cars would seldomly but periodically drive by. Some cars would honk at the almost naked whore getting pounded by bums. Some bikers said things too, usually it was about her ass. This humiliated Jennifer even more. She wanted this to be over and didn't want people to see her being a slut with bums! Jennifer thought she was a nice girl. Bystanders could catch a glimpse of Jennifer's ass and her whole right side. Her tits we hanging out and bouncing away. Her messy hair gave her some cover for her face. Still she looked like a slut from last nights club and was getting handled by the homeless.

During the fucking on Jennifer, Tom tells her more about last night. He mentions that did this exact thing to her last night. Apparently, Jennifer was so into it last night that she did many positions on the bums to get fucked. He told her some of the moves she did last night. How she danced on both their cock and bounced her ass real good. Jennifer was stunned. She felt her stomach drop when she heard this. How much of a slut she was last night has gotten her into so much trouble she thought. She felt so stupid. She almost felt like she deserved this now. The bums were treating her like the slut she was last night.

Jennifer thinks as she satisfies two dicks in the alley. "But I was drunk! I didn't mean to be a slut! oh my. its so hard. so much dick. These guys don't stop fucking me. oh fuck. oh fuck.

Finally, Dick pulls out of her stretched pussy. She groans with the pull out and waits for further command. She was hoping it was over now. This couldn't get any worse. The bums have fuck her twice over now. They must be done she thought. She was wrong.

Chapter 4

Jennifer yelps when she feels two hands slap down on her round ass. Then two hands push down on her shoulders, shoving her face to the palettes. Only her young round ass thrusts in the air. Tom is holding her behind. And Dick pins her chest down.

"oh so one more thing before you go, babe." Tom stares at her displayed ass. "I'm going to fuck your ass." He stares at her butt hole.

Jennifer's heart skipped at beat when she heard that. She screams back "What! Wait! No! Please! I've. I've never done that! I'm a nice girl! Please not my ass. I haven't done it there. I swear. Please don't! Not in my ass. No don't! ow! ow! ow! oh my! please! stop! not my ass! ow ow!"

It didn't matter what Jennifer said. Tom was going to get his dick in her ass. He was going to push his dick in this tease of a slut's fine round ass. And that's exactly what he did.

He spread her ass cheeks. And with a big smile aimed his homeless cock at Jennifer's back door. Jennifer is so nervous and scared of whats going to happen. She struggles against Dick's hold on her. She strains her eyes to look back at Tom as he stands between her parted feet. His naked dick only inches way from her cunt and ass but it was her asshole that Jennifer knew the bum wanted to stick his dick in.

She still screams out to Tom, "Please don't. Please don't. Not in my ass. Not in my ass sir! I'm sorry ok! But. But please not in my ass. Fuck me sir. Fuck my pussy. Please. Please not my ass. I've never done it there! No! Stop! Please! oh oh not my ass! I've never done anal!" All her pleads make Tom even more eager to fuck her ass. Now he has extra motivation to be the first to fuck this fine slut's round vulnerable ass.

Tom starts to spit on his dick and yells out to Dick. "Hey Dick! Give me some spit. Spit on my dick! So I can enter her ass real good. I want to slide right in her bunghole. Yea thanks that's it." Dick leans forward and gives plenty spit on Tom's raging cock.

Tom is almost drooling himself at the sight in front of him. In front of him is a young innocent 21 year old forced to show her ass and pussy. Her tight blue dress hides nothing as her ass and tits are on full display. The dress covers her back but flaps downward once it gets to her ass crack, leaving her behind in a humiliating exposed way. Jennifer trembles and whimpers as she is held face down ass up in a public alley. The palettes presented her embarrassment like a dumb slut on a stage. Jennifer was stuck on those palettes ready for a butt fucking. She looked like a club tease was going to get butt fucked by a bum in the alley.

"It's not going to fit! Please don't! Not in my ass! Let me go!" Jennifer pleads again as Tom approaches her uplifted naked butt. "oh no. oh no. oh no. oh please no. He's going to try to fuck my ass! This is it! A bum's fucking my ass! oh my! This sucks so hard. oh fuck! oh fuck my ass!" Jennifers thoughts as he walks closer.

Tom steps closer to the trembling butt cheeks of a dumb brunette. Her dumb slutty acts last night got her here. And now he was going to shove his dick in her ass. He didn't care if it was her first anal experience. He didn't care if it was 7 in the morning. He didn't care he was in an alley ready to be seen by anyone. Her body was so beautiful. Her butt was so round and her hips flared out nicely to hint where to hold when pounding her. Her juicy ass cheeks were already parting. He just needs to start shoving it in her innocent waiting ass hole.

Tom does it. He starts to shove his hard dick in her backdoor. To everyone's surprise, he pushed right in. His cock head wasted no time in poking right in her butt hole. Jennifer screamed and grimaced. The cock felt terribly awful in her butt. She could feel her anal ring tightening on his dick already.

Jennifer was in a loss for words. She couldn't believe what just happened. That The homeless man got his dick in her ass. It felt like at least half the dick was in, when actually just the cock head was in her ass. After all the guys she's said 'no anal' to now she has her ass given up to a homeless man. She kept thinking how her first time is with a fucking bum. A bum is about to fuck her in the ass, Jennifer thinks to herself. She is flustered with humiliation and regret of going to this club in the first place. Jennifer just wanted a night to dance with her friends and now she's sucked homeless men dicks and worse, much worse, she's spreading her ass cheeks for them. The young girl didn't want to fuck bums and Jennifer definitely didn't want dick to go in her ass. She's exhausted and humiliated by all the fucking she has been through this morning already. The sun was getting brighter, Jennifer wanted to get home. She wanted off the palettes. She so desperately wanted Tom's dick out of her ass.

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