Isabelle Over Her Head Ch. 02

Story Info
Isabelle gets blackmailed into a gangbang.
3.1k words
186.6k
55
0

Part 2 of the 2 part series

Updated 10/02/2022
Created 10/09/2010
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

Isabelle had told Michael she was an insatiable whore. She had admitted to him the things she loved and fantasized about: being watched, porn, rough sex, face-fucking, humiliation, dirty-talk, anal sex, gangbangs, gloryholes, prostitution role-play and rape role-play. While many of her fantasies had already been fulfilled, she still had some unfulfilled. Michael read her clearly and in fucking her throat brutally and cumming on her face he broke her in, so to speak. He knew she would go through with the things she said.

The first night they met he came three times. The first was all over her face. The second time was in her pussy. He wasn't sure he would take her a third round until she began screaming for him to fuck her harder. His cock was 9 inches long and almost 6 inches around. As far as fucking went, she should have been begging him to be gentle. Not Isabelle, though. Isabelle was built to take cock and she had an addiction for big ones. She loved how it hurt when they pushed too far and how she thought they would literally rip her open. But he wanted to see her squirm and gasp and beg him to be gentle and he didn't get that satisfaction when he abused her young cunt.

So somewhere around 3AM they had finished 3 drinks together in his studio. On top of the 3 she had between 9 and 10 that night she was undoubtedly drunk. Her hands began running along his limp cock and she slid from the couch back to her familiar position on her knees in front of him. She began to bring his cock back to life with her expert tongue and lips. "You insatiable, whore. You sure you want to go down this road? There is only 1 hole left on your body I have any interest in now."

She took his half hard cock all the way in her mouth and attempted to lick his balls while doing so, drool poured from her mouth and on him as she managed to mumble out, "mmmhmmm".

In no time she found herself on her knees on the couch, her head on the low arm rest. His well lubricated fingers were making their way easily in and out of her asshole. He pushed in a third to prepare her well. He didn't want neighbors thinking he was murdering someone when he finally took her ass.

Michael spent 5 minutes toying with her asshole, 30 seconds lecturing her on how her tight hole would never be the same and 15 minutes making her scream. Isabelle had never felt so full in her life and she had successfully received double penetration in the past. She didn't even enjoy it for the first 5 minutes, she managed to relax in the middle and by the end she was telling him to spank her. She was demanding he fuck her hard and abuse her and remind her what a whore she really is.

When Michael was done with her he called her a taxi and told her to be check her email when she woke up. She woke up giddy and incredibly sore at noon. The soreness in her head was from the drinks and the soreness in her pussy, ass, throat and jaw were obviously from the abuse she took. Still, she had to return. Everything seemed like a good idea when she was drunk but now the very real possibility of her internet debut hung over her head and she couldn't have that. She checked her e-mail and followed the instructions.

She showered and had a light breakfast and relaxed until 5:00. He had told her to meet him on one of the busier streets in town. She knew the area pretty well as she passed it on her commute to work. So at 4:30 she got on a bus as instructed. She wore a skirt, flat shoes and a tight shirt. She was told to forget the bra and underwear so she was sure to cross her arms and legs on the bus ride there. Michael was waiting for her at her stop with a smile. "OK, Isabelle. We can fulfill so many of your fantasies right here!"

She looked around. "Right here? At a bus stop? Listen, I know I told you I'm an exhibitionist but I'm not fucking you at a bus stop in day light."

Michael laughed and grabbed her should and spun her around. He pointed at a glowing sign that read, 'Peep Shows'. She was confused. "I like porn stores but what the fuck is a Peep Show?"

He smiled again as if she were so naive. "Peep shows, my dear, are code word for gloryholes 99% of the time. These ones are particularly good. This is my store and I have some friends who would love to watch you work my cock."

She was stunned. She never thought she was ACTUALLY visit a gloryhole -- she just loved the thought of it. How dirty she would feel playing with her pussy as some perverted stranger watched through a small hole. How maybe she would suck on a big fat dick while others watched and wished. And now her chance was upon her and she didn't feel ready. Michael sensed this and he assured her, "Listen, just do what comes naturally to whores like you."

He led the way into the store. He waved to the person at the front desk and they opened a door that lead to the back. It was dark and smelled of sex. Isabelle grabbed his shirt so she wouldn't lose him in the darkness. He knew the place well and he politely opened a door for her. "OK, this is your booth. Find something nice to watch. I'll take the booth on your right. Some of my friends are already here to watch. Oh, and don't worry. They all go through a lot of tests to make sure they're clean before I allow them in any of my films." On that note he slipped into his box. It suddenly occurred to Isabelle that his friends were amateur porn actors.

She stepped into her dark box and locked the door behind her. It was small with just 2 walls, a screen and a door behind her. She pushed the glowing red button and the screen lit up. She flicked through the channels rather naturally until she found porn of a woman fucking someone rough-looking in front of another guy who was tied up and forced to watch. The woman's hands were tied behind her back and she obvious loved the rough pounding she was taking.

She watched it and knew what she had to do. She decided to take advantage of the situation she was in. She reminded herself that this was her fantasy. "Oh fuck, Isabelle... What have you gotten yourself into?" she uttered under her breath before submitting to her fate. The focused on the woman on the screen and admired the cock that was now roughly making its way up her asshole. Seeing the woman squirm and scream and pull against her restraints began to make Isabelle wet. She hiked her skirt up a bit and widened her stance. She glanced at the hole on her right and could see movement on the other side of the hole. It was Michael waiting for the real show, obviously.

She looked to her left and noticed movement on that side as well. She knew she was safe in her box and knowing that someone was already watching got her wetter. "You boys want a show?" She pulled down her shirt slowly and began fondling her own tits. She licked her left nipple as her other hand slipped under her skirt to begin teasing her aching pussy.

After a few minutes of this she found herself very wet. She wished she had somewhere to rest so she could play with herself less awkwardly and looked around in futility. She finally decided to sit on the firty ground with her legs spread. She leaned against the door and looked up at the screen as she started fingering her pussy. She was bringing herself close to cumming when Michaels cock pushed through the side of her booth. Show time. She got on to her knees and took it in greedily. She thought to herself for a moment how she must have been really drunk last night -- his cock seemed bigger then. She smiled when she next thought that she must just be getting used to it already.

Out of the corner of her eye she noticed a hole in her door and she thought she saw movement there too. Used one hand to finger her wet slit as she worked this cock as expertly as possible. Michael's cock was already making her jaw sore but she was soon to get relief. After only a few minutes it started to throb and she could hear him moaning. She pulled her face back and left the tip in her wide open mouth. Him hot cum exploded all over the inside of her mouth and tongue and down the back of her mouth. She swallowed every last drop satisfied with herself. Only problem was that she was still horny. The cock withdrew itself from dark hole and she could see his tongue flick through the hole. She needed no more invitation then that.

She stood up and dropper her skirt to the ground. She leaned over as far as she could and kept her legs nice and straight to ensure whoever was at the door was getting a good show. She gasped when the tongue first probed her asshole and began to sigh and coo as it worked her expertly. "Mmm fuck yeah, lick my asshole, you dirty bastard. Kiss it better for that brutal fucking you gave it last night!"

2 fingers pushed into her pussy and began to fuck her as the tongue continued pushing as deep as it could into her asshole. Isabelle was going to cum and she needed to brace herself. She lifted her head a bit higher and put her elbow on the wall in front of her. Her jaw dropped open and she began screaming to herself and she came. A cock pushed through the hole that she had inadvertently put her mouth up to. Her orgasm distracted her too much to give a shit and she simply closed her mouth on the invasive prick. She barely noticed that she was sucking on it until she was done cumming. Michael had stopped finger and tongue fucking her and she could feel his cock begin to push it's way into her cunt. She pushed her ass against the wall hard to encourage him and in only 3 thrusts he was as deep inside her as the booth would allow.

"Oh!" She pulled the cock from her mouth and stroked it so she could speak. "OH! OH! OH! YESSS! Fuck me!! I'm your whore!!" It hadn't been her intention but this set the mystery man over the edge. His cock quickly pulsated in her hand and shot hot cum on her chin and her cheek. She took it back in her mouth and sucked on it until he voluntarily removed it. She was pounding back hard against the wall desperate for more of his cock when it dawned on her that she had just made him cum only 5 minutes before he was fucking her again. Was he that good or was this someone new?

Another orgasm started rolling through her gently and suddenly she didn't give a fuck. It sure felt like Michael! She pushed her ass against the wall and let him do all the work. The booth shook as he fucked her with force and this time she nearly collapsed when the orgasm overtook her. She didn't even notice the cock stop thrusting as it sprayed cum deep in her belly. It quickly pulled out of her and she collapsed to the floor. "Fuck... Oh my God. Fuck me, this is too good." Isabelle was talking to herself again.

A familiar voice spoke to her through the hole in the door. It was Michael's voice. "Well done, slut. Now open the door so you can take my cock."

She got to her feet and opened the door with some confusion. It had occurred to her that maybe the cock that fucked her wasn't his and she knew now she was right. "That wasn't you fucking me."

He looked at her straight-faced. "Baby, that wasn't me doing anything. I decided to be polite and let a couple guys ahead of me in line." He unzipped his pants and revealed his rock hard dick. The look on her face amused him. "So what you're good at."

She couldn't do anything else now. She dropped to her knees once again and took him in her mouth. He knew she was warmed up already and he wasted no time. "Show the boys what you can REALLY do!" He emphasized this statement by choking her once again with his cock as he had the night before. She could hear voices around and now that her eyes were adjusted she could make out the shapes of at least 2 other guys. They were commenting on what a hot slut Michael had now and openly asking one another if anyone had worked with her before. Michael only wanted to give this blowjob show for a few minutes though.

He pulled her to her feet and kissed her on the mouth. While doing so he slapped her ass hard. When he was done kissing her he told her, "You'll fuck me now in front of my friends. Show them how much cock you can fit. Don't disappoint me."

"I'll take your whole fucking 9 inch cock inside me." Isabelle was confident.

Michael lifted her by her hips and she instinctively wrapped her legs around him and her arms around his neck. He aligned his big dick with her soaking wet pussy and lowered her on to it with ease until she was sitting on his balls. She felt smug.

"Oh, I know you can take 9 inches. Any whore can do that." He now had her where he wanted her. "But 2 of my friends are 7 inches and one is a little larger than that."

Isabelle looked panicked and even though the cock in her pussy was divine, she wasn't sure she could take a second. Not in this position. Not with someone whose face she'd never seen! Her mind was racing and as she opened her mouth to speak she felt a hot, lubricated cock begin to demand entry into her tight anal passage. "Wait! Wait! I don't think it will fit!" She was finally able to speak up but it was too late.

The mysterious cock behind her spoke into her ear, "I think it will." His hands grabbed on to her just above where Michael's were and the man slowly pushed his cock inside her.

Isabelle was in pain like she'd never experienced sexually but couldn't help but notice how wet she was also. Michael grabbed her by the face as she started to scream. "Don't fucking embarrass me, bitch!"

She relaxed as much as she could. "OHHH MYYYY GOOOOODDD!!" She couldn't say anything else. The cock finally settled balls deep up her ass. "OH! God! OK! OOohhhh Ahhhh!! Ok... Ummm... Fuck!" She couldn't make any sense and that just made the men hornier.

Michael spoke again, "Well, are we going to let her massage our cocks like this or should we fuck her?" This was followed immediately by the two of them raising her up 6 inches and lowering her. They ignored her screams. She was trying not to beg them to stop. She wanted to be good and she wanted to be that ultimate whore she had bragged she was but they were making it difficult.

They lifted her again and dropped her more quickly. They begin to increase the rhythm of their thrusts and after a few minutes the man up her ass withdrew. She was thankful for the break despite the fact that she had been getting used to it. She felt a new set of hands grab hold of her roughly. A new man took over and although his cock was the same size, his had fresh lube on it and she actually enjoyed it as it entered her. "OHHH YES FUCK ME!"

The two men laughed and began thrusting harder as Isabelle began to scream. She thought for a moment, 'if only he could see me now. His beautiful girlfriend impaled off the ground by two massive cocks in the sleezy back hallways of a porn store!!' the thought sent her into orgasm. Her screams were fanastic as she came. She begged for more and told them not to stop! "I NEED IT! I NEED COCK!! FUCK ME MORE!!"

For over an hour she was used in the hallways on the gloryholes booths by Michael and 3 amateur porn actors. They took turns at some points and they alternated between her pussy, ass and mouth. Sometimes all 3 of her holes were filled and twice she found they were forcing 2 cocks into 1 hole. Once, two cocks pushed into her mouth and she loved it. But the second time she screamed in agony as a second cock stretched her pussy walls wider than she ever felt before.

Michael admitted to her later that he didn't know them well but they all applied for jobs with him. After he had them tested he told them they had an "on camera" audition. Isabelle didn't even believe him until he showed her a video of her being fucked by a strangers cock in a dark booth while another came on her face. "Don't worry," he assured her. "It's just 1 more video for the vault to make sure you do what you're told. You wouldn't want hundreds of thousands of porn-hungry perverts thinking you're a filthy, glory-hole going, amateur gangbang prostitute, would you? That's what you looked like in that video to me."

She was in deep now. Whatever he had planned for the second and third day was going to be extreme and she would have to do it without complaining. She checked the emails to see what was left for her fantasies and fetishes. "My god..." she gasped. The list was brutal albeit incredibly hot:

Being tied up and blindfolded in a park while getting fucked.

Prostitution role-play

Rape role-play

"Well," she thought, "He can't do all three in one day... I hope." That night she came thinking about it despite the abuse she took earlier. Michael was right, she was an insatiable whore.

Share this Story

READ MORE OF THIS SERIES

Similar Stories

Be Careful What You Wish For My gf and I get more than we expected at the Gloryholes.in Group Sex
Accidental Gangbang Wife-to-be ends up fuck-slut at her fiancé's bachelor party.in Group Sex
Wife is Taken and Fucked at Party Sweet little Wife is taken in front of her husband.in NonConsent/Reluctance
Garage Gang Rape Claire gets into trouble when she can't pay her repair bill.in NonConsent/Reluctance
Three Days of Watching my Wife Fuck Vacation, watching reluctant wife fuck Spring Breakers.in Loving Wives
More Stories