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Introduction:

Jim runs into his ex and her best friend on a night out and realizes this is his chance to do something hes always wanted to do.

Jim hated going to bars in this part of the city, but if he wanted to get laid then there was no better place. He tried a place called Lucky Jay’s but the pickings were pretty slim. He spent a couple hours bouncing from one bar to the next without finding a chick who was that sweet spot of drunk, cute, but not too cute to attract all the other guys out looking for fuck meat. He’d given up hope when he pulled out his phone and was about to call a ride home.

“Oh my fucking god is that Jim?!?!” Jim turned around to see Antoinette. She was on the short side and was carrying just a little too much extra weight but was still somebody he’d always considered fuckable. She had this habit of dying her hair a different color every couple months and even though he hadn’t seen her in a while she was currently rocking her naturally brown with what looked like purple highlights.

“Shit, Antoinette, I thought you’d moved for work. What are you doing back here?” Jim was horny and he’d never fucked Antoinette so he figured he should go for it. By the way she was holding herself it looked like she was well liquored up.

“I’m here visiting Ashley, she’s not having a good night so we were going to call it early. So fucking lame, I know.” Jim had guessed as much. Jim and Ashley had dated for a while, but never really clicked. Ashley strictly enforced an “only one hole is open for business” rule which drove Jim nuts. She also was a bit of a butter face. She had long blonde hair, a tight ass, and great C cup tits, but her face just didn’t sell the package. When they had realized there was not future and the sex got stale they amicably slip. Jim had always wanted to fuck Ashely’s tight little ass but the opportunity just hadn’t presented itself.

“Oh, that’s kinda too bad, I was thinking it might be fun for us to hang out a bit, but I don’t think Ashley would be thrilled with that.” Jim was looking around to see where Ashley was.

“She’s not really going to be thrilled about anything tomorrow.” Antoinette moved to the side to show Ashley slumped over on a bench, Jim guessed the puke on the ground next to her was her own doing.

“Holy shit, is she ok?” This could actually work to his advantage. Fucking Antoinette at Ashley’s would be super convenient and kinda hot knowing how much it’d piss Ashley off.

“Yeah, she only had a couple drinks so I think somebody was trying to get lucky.” Antoinette loved using air quotes, which Jim ignored as his mind was racing.

“We should get her home, does she still live on 14th and H?” This was just two short blocks away. Antoinette confirmed she was still in that studio apartment, and the two of them began helping Ashley back home. While making small talk it became clear that Antoinette was eager to get thrown a bone. Jim spent most of the walk trying to cop feels of his ex but didn’t want Antoinette to notice. When they finally got into the apartment’s elevator Antoinette pushed Jim into a corner, sandwiching Ashley between the back wall and their bodies. Without saying a word Jim began kissing Antoinette. With one hand he grabbed Antoinette pulling her close while we snuck his other hand up the bottom of Ashley’s skirt. Jim pulled her panties to the side and began exploring her. Easily the best part about Ashley was that her pussy seemed to always be a little wet. After wetting his middle finger a bit he began pushing it against her tight rosebud. He had just forced the tip of his finger in when the elevator stopped and the doors opened.

Antoinette pulled herself off of Jim and helped him get Ashley to her apartment. Jim instantly recognized the place, she still had a large sectional taking up most of the room and her bed was off to the left. She also had all these blue glass bottles she collected and filled with sand or beads or what have you. There was evidence in the kitchen of a bit of pregaming. They got Ashley up and onto her bed.

“Hey, I could use a drink after all that work. You want anything?” Antoinette asked as she walked to the kitchen. Jim didn’t want anything to drink but was trying to figure how he could fuck Ashley up the ass tonight.

“How about we do a quick shot or two to take the edge off” Jim walked to the Kitchen where Antoinette was pouring the shots. She had poured out two shots of vodka. Jim grabbed Antoinette and pushed her up against the counter. He kissed her deeply for a couple seconds and then took a shot and poured in down her throat. Antoinette wasn’t use to being handled like this and was loving every second of it. They made out a bit more, when Jim grabbed the second shot. He stepped back from Antoinette and handed her the shot. Jim dropped to his knees and lifted up the front of Antoinette’s skirt. Pulling her panties off, he began licking her pussy. It was a little muskier than he’d like but it was getting him hard and she was clearly enjoying it. He didn’t want to get her off just yet so after a couple minutes of some deep licking he came back up, poured the shot into his mouth and then kissed Antoinette. Jim locked lips with her and forced the vodka back her way. She quickly swallowed the mixture of her juices and liquor. Jim poured out another two shots while still locking lips with Antoinette.

Antoinette was getting real frisky and Jim was rock hard so he grabbed her hand and led her to the sectional. It didn’t take long for both of them to rip each other’s closes off and much to Jim’s surprise Antoinette’s fat tits were actually really firm and supple. Jim pulled her to the edge of the couch and pressed his cock against her slit. Between the quick oral and the general exciting Antoinette’s chubby little cunt was ready to go. She wasn’t as tight as he’d like, but she was comparable to Ashley.

Still focusing on her tits he reached out and grabbed one in each hand and squeezed hard. She had big dark areolas with fat nipples. As he pounded into her chubby pussy he bent forward so he could bite down on her nipples. It didn’t take long before Jim felt his first load building. He had heard Antoinette joke before about how much she like swallowing cum, so he decided to test those comments. Moments before he knew he’d release he pulled out of her sloppy cunt, got up on the couch, and plunged his cock into her mouth. Two pumps in he came and sure enough she kept sucking and swallowed it all down. Jim dismounted from her face and collapsed on the couch next to Antoinette. This alone would have qualified as a great night for Jim, but he still needed to keep is eyes on the prize.

Antoinette wasn’t showing signs of slowing down, and Jim was worried if he waited too long Ashley might start to come to. Trying to get a better gauge on things he decided to prod some more, “Hey so what happened to Ashley again? I don’t think I’ve ever seen her like that.”

“Well, she wa was being a bit of a party pooper and didn’t want to pick up guys, so you know” Jim honestly had no idea what she was insinuating but it now sounded like Antoinette had been behind whatever happened to Ashley.

“Ha, so what you roofied your friend? I can’t see you doing that.”

“Nooo, it wasn’t a roofie. But normally they just make me tired and want to go to bed. I didn’t realize she’d get that sick from one.” Hot damn, Jim realized he’d have plenty of time to figure out Ashley. Her best fucking friend had drugged her so she could get laid. He was a little baffled since he always thought Antoinette was somewhat straight laced.

“Well fuck, I need another drink.” Jim got up to get the shots he’d poured. As Jim stepped into the kitchen he saw Antoinette’s clutch, and immediately opened it. Sure enough there was a little pill case with small white pills in it. He took the case and removed one pill. Using a spoon he crushed it and put it in one of the shots. It didn’t really dissolve all the way but hopefully Antoinette wouldn’t notice. He walked back to the couch gave Antoinette the shot. She quickly took it, and swished it around her mouth before swallowing. Jim didn’t know how long this would take to kick in but figured he should do what he could to hasten the process. Thinking of ways to moving things along he remembered a video he saw once and went back to the kitchen the grab the vodka bottle.

“Antoinette, for my shot, I want something special.”

“Yeah, uaandss whats ththats?” Maybe it wouldn’t be too long after all, but Jim knew this was sure to put her over.

“I want to take a shot from your pussy.” Antoinette looked confused but smiled.

“I wants you to take whatever form my pussy!” Jim moved the coffee table away from the couch and got Antoinette situated so she was upside down against the couch. Her shoulders were on the carpet and her lower back was against the front of the couch, leaving her ass and pussy level with the couch seat. Jim got over her in a slight sixty nine and began eating her out again. He wasn’t sure how much vodka was needed but he wanted to be safe. As he sucked on and licked her clit he began stretching out her pussy a bit. It was already a little loose from the fucking but he wanted to be able to pour vodka into her, so he needed her to stay open. He was so consumed in spreading her he didn’t realize at first that Antoinette was orgasming. The fact that his abuse was getting her off just made him harder and more eager. Jim pulled off of her clit and let her writhe a bit. Once she had calmed down he spread her lips and was happy to see her gaping a bit. He took the shot he’d poured and slowly emptied it into her snatch. There was still more room in her pussy so he reached for the bottle. As he settled back in he felt Antoinette playing with his cock and balls. He adjusted himself and little so she could start sucking him off. Jim poured a little more vodka into her pussy, to the point where based on her breathing a little bit would spill out. He estimated he’d poured at least one more shot into her. He didn’t know how quickly the alcohol would soak in but he wanted to get on with it. Figuring he’d repeated what he did earlier he bent down and sucked some of the vodka out of her and went to give it to Antoinette.

“No no no, I’m good. Give it to the sleepy slut.” She gestured weakly to Ashley. Jim didn’t need to be told twice. He stood up with a mouth full of pussy flavored vodka and went to the bed. Ashley was face down on the end of the bed. Jim pulled her to the ground so she was sitting with her back to the bed, her head barely leaning back onto it. It felt weird going in for a kiss with this girl who he had history with but as he held her head with one hand and locked lips, he began poking around under her skirt with his other hand. It was tricky to get the vodka in her mouth without her actively participating but he went slowly and tried not to make a mess. With how she was sitting he didn’t have a good angle on her ass, but her pussy was still ripe as ever. It took a couple minutes but soon his mouth was empty.

He turned back to Antoinette who hadn’t moved and inch over the course of his exchange with Ashley. Getting over her he nudged her slightly with his foot. She stirred and smiled. He went down and sucked the remaining vodka from her.

“I waaant yous to fuck me in er bed!” Jim was confident that Antoinette was going to be passing out soon. It seemed the pill had done it’s trick and seeing as he barely had a shot in his mouth he decided to just down it. It took a bit of effort but he got her up and into the bed.

“No, with heeerrr tooo” Jim smiled and went over to Ashley. He somewhat unceremoniously stripped Ashley down. She did have a cute body and if it weren’t for her face she’d really be something. He picked her up and laid he next to Antoinette. Antoinette was fading in and out so Jim gave her a slap on the ass. She didn’t stir so Jim hit her harder. Still nothing. Jim’s heart started racing, he could do what he wanted with both these girls. He rolled Antoinette over and grabbed his phone. He took a couple pictures of both of them so he wouldn’t have to use his imagination anymore when he beat it to them. He was still recovering from his first go around, and decided to poke around their phones while he got into the mood.

He went through Ashley’s phone looking for any pictures she may have shared with any guys but somewhat to his disappointment he couldn’t find anything good. She’d never sent him any sexy pics so he guessed she kept to that rule. When we went to Antoinette’s phone, it was a different story. It didn’t take long for him to find Antoinette’s “hidden” folder and it was a treasure trove. She was much dirtier than he could have hoped. He began transferring all the photos she had over to his phone, he’d have to go through and delete the tons of dick pics she had saved but for the time being he was getting hard scrolling through what she’d captured. He started to go over the edge when he came across pictures from a vacation Antoinette had taken with Ashley and their friends Courtney and Cindy. It was one of those all-inclusive deals on an island in the Caribbean. It happened a month or two after Jim and Ashley started dating, and Ashley had been texting and posting photos the whole time, it seemed you’re your standard vacation. He’d seen lots of pool and beach shots but nothing too crazy. Antoinette’s photos told a very different story. The bulk of the photos seemed to be from two or three nights and involved all four girls in different states of undress and sobriety. Ashley and Cindy were buck naked in all of them, passed out on a chair, a couch, or the floor depending on the night. What really amazed Jim was that Antoinette had document as different guys had fucked her friends and herself. It started to settle in that this wasn’t Antoinette’s first time drugging her friends to have a good time. He kept on scrolling through the vacation pictures but he was getting too hard seeing these girls getting fucked by random guys, and Ashley’s “one hole” policy being completely disregarded. He thought this one photo of Ashley riding a guy’s cock while she also took another one in the ass was especially poignant. Knowing Ashley would already be pissed on Antoinette in the morning he decided to send that one over to Ashley in a text message.

He made sure all the photos were transferring and looked back at his ex and her trash friend. He felt that he now owed it to Ashley to make Antoinette pay a little for what she’d done. This didn’t mean Ashley was off the hook, far from it, but he would be sure to stay for as long as it took to make Antoinette think twice about drugging her friends.

Jim got off the bed and picked up Ashley. He walked her limp body over to the couch and deposited her in a heap. Now that Antoinette was alone on the bed he knew what he wanted to do. He went to Ashley’s dresser and pulled out some belts and scarfs. Returning to the bed he adjusted Antoinette and spread her thick thighs apart. Using the scarves he tied her legs as wide open as he could. Between the pictures and seeing Antoinette on display he began to get hard again. Jim decided the lesson might be missed if Antoinette didn’t have picture evidence so he grabbed her phone again. He took his time taking detailed photos of her sloppy pussy. Once he was satisfied with the before pictures he picked up a thin leather belt he’d grabbed from Ashley’s dresser.

His first swing of the belt was soft and only elicited a twitch from Antoinette. The belt landed on her inner thigh almost an inch from her lips. The next blow landed dead on her clit and even in her drugged state Antoinette let out a grunt. It wasn’t too loud so Jim repeated the blow. This time her yelp was a little louder. Wanting to really lay into her he grabbed Antoinette’s and Ashley’s underwear, balled it up and stuffed Antoinette’s mouth. The underwear was less material than he’d hoped so he grabbed two more pairs from Ashley’s dirty laundry.

Testing to see if his makeshift gag worked he took a hard swing at one of her tits. He was satisfied with the gargled yelp. Jim looked on as his belt mark reddened and rose slightly across her tit. He was rock hard at seeing what he could do when he really swung. Before returning to her cunt he made sure to turn her tits into red ripple covered mounds. Satisfied with the fact she wouldn’t be able to wear a bra without wincing he returned to Antoinette’s snatch. None of his previous swings were still visible but with his new sense of power he laid into her pussy. Around the fifth swing he was getting worried she was making too much noise even with the gag. Stepping back for a moment he realized he might not need to do much more. She had several welts rising up along her lips and it even looked like she’d have bruising. Jim took several more shots of her and got down for the main event.

Her pussy was still a bit wet from before and Jim was sure she could take more than he’d given her earlier. He was able to fit three fingers into her sloppy cunt right from the start. He was playing with her pussy a bit but didn’t feel like eating her out again. He’d barely gotten his fourth finger into her when he decided he needed lube and something to stimulate her with. Jim had never seen Ashley use any sort of toy but decided to search one out anyways. Not too surprisingly Ashley didn’t have any sort of vibrator or lube. Jim thought about what this implied for Ashley’s asshole but then the idea of tearing her apart a little seemed appropriate for the situation.

Searching through the bathroom Jim realized Ashley had one of those electric toothbrushes. Figuring it was mechanically the same as a vibrator he grabbed it and returned to his bound slut. Knowing he’d need Antoinette to produce her own juices Jim settled onto the bed by her pussy. Grabbing her clit in one hand her turned on the toothbrush and brought the backside of the head to her engorged nub. Within moments of him pressing the vibrating head to Antoinette’s clit she began writhing around. It almost sounded like it was painful for her but that didn’t matter to Jim. He adjusted his body a bit so he was pinning her legs and not relying on the binding. He began working her clit again and despite her bucking and yelping her was able to keep the vibrating head up against her clit. It didn’t take long before he noticed the slight difference in her breathing and moving. She was still trying to fight back against the over stimulation but he finally felt like she was going to orgasm. He felt a subtle shudder course through her body and for a second she rested before trying to buck off the toothbrush again. Deciding to test the waters Jim removed the toothbrush and felt her pussy. It was even sloppier than it had been earlier and Jim was able to get four fingers into her with ease.

He moved down the bed and began working his hand into her with his full weight. By pointing his fingers and tucking his thumb he was able to get his hand into her but this wasn’t what he really wanted to see. The second time he pushed his hand in he balled it into a fist and slowly pulled it out. Antoinette’s pussy strained but he was able to remove his fist without too much of a struggle. With his free hand he got his phone ready. He turned on video and panned from Antoinette’s cute cunt up to her face. Bringing the shot back to her snatch he began pressing his fist against her hole. There was clearly resistance but all of a sudden his fist popped into her. He quickly pulled out and repeated this a few more times. Each penetration getting easier and easier. When he felt that the slut had had enough he pulled out and brought the phone down to her stretched pussy to watch it slowly try to close back up.

He ended the video and marveled at how loose she was. He tried his fist again and sure enough it slipped back into her. Shaking his head he got up and wiped off his hand. Antoinette’s tits had lost their overall color, but he could see some bruising forming. Her mound also had some minor bruises but nothing too crazy. Jim contemplated giving her tits another once over but decided instead to get to his real prize. Not wanting to cause permanent damage he untied Antoinette’s limbs and left her on the bed.

Jim’s dick was rock hard as he approached his passed out ex. He picked her up and draped her over one of the couches arms. He positioned her so she was lying on her belly with her ass in the air. Not being able to stand in any more he began pushing his cock up against her tight little rosebud. She didn’t have any give though. No matter how he positioned himself he couldn’t make any headway into her cavity. Frustrated he took a step back and slapped her ass as hard as he could. He loved seeing his hand print on her. Taking his thumb he begins pushing and trying to stretch her hole that way. He could get his thumb just barely into her, but he knew he needed a longer term solution. He dipped his thumb into her exposed snatch, which provided some lubrication but not enough for what he wanted to do. Jim looked around the room and saw Ashley’s toothbrush on the bed. Without hesitating he grabbed in and approached Ashley again. He turned it on and began teasing her little clit. Within moments she had started to buck her hips into the couch. He tested her cunt again and sure enough her fluids had started running. In no time he was able to work his thumb all the way into her tight ass. He just had to alternate each penetration between her snatch and her asshole. Ashley was letting out a moan into the couch seat as Jim pulled the toothbrush away and stood behind her again. He slipped his cock into her pussy and gave her a quick two pumps. Pulling his dick from her sloppy hole he pressed against her asshole. With the thumb work and the pussy juice his head slowly pressed through and soon he had buried an inch of his cock into her. Eager to cum and wanting the full experience Jim pulled out of her ass and plunged into her pussy again. Two pumps later, he was back out and knocking on her back door. This time he was able to get about halfway into her. He knew he wouldn’t be able to last much longer, he had too much of a build-up. He chanced it and switched back to her pussy. He almost came as he entered her and he quickly pulled out. Taking a breath in. he pushed his cock into her ass as hard as he could and bottomed out. With his second pump he was cumming in her ass. He collapsed on to her and lay there with his cock in her for a minute. He’d fucked her ass, but it wasn’t what he wanted. He should have emptied a load into that bitch on the bed or something so he could really have had fun with Ashley.

He knew it was getting late so he pulled out of Ashley’s ass and stepped back. He began gathering his things and putting them in a pile by the door. He went over to Antoinette and pulled out her gags, keeping her panties for himself and putting Ashley’s back in her hamper. Going back to Antoinette he felt some of the welts on her tits and pinched her nipples a bit. To his surprise his cock started to get hard again. He slapped her tits and turned back to Ashley. With each step he took towards her he was getting harder and harder. By the time he stood behind her little ass he was as erect as he’d been before.

Not wasting any time with her pussy, he spread her cheeks with his hands and pressed into her once more. He was able to push all the way in on his first try this time, even though his cock wasn’t lubed. He felt the slickness of his cum in her and was turned on that this was the only thing protecting her from a torn asshole. As he thrust into her delicate hole he felt the lubrication decreasing. Not wanting to have blood on his dick he pulled out to lube up in her pussy. He saw that he was already to late, but enjoyed fucking his ex with a blood speckled cock. As soon as he felt that he was lubed up enough her was back in her ass. He could feel himself building and was trying to resist but this was too good of a feeling. The only thing that could have made this better would be for her to know it was him who was violating her so badly. He reached forward and grabbed her head by her blonde hair. He pulled her up into a standing position as he felt he was about to cum. Wrapping one arm around her front, her turned her head and gave her a deep kiss on the mouth as he released into her ass once more. He released her and let her fall to the couch.

Panting he took a step back to look at his work. Her asshole had already puckering back up and a small stream of cum was running down her smooth cunt lips. Not wanting to miss the opportunity he grabbed Antoinette's phone again and snapped a picture encompassing Ashley’s situation but focusing on the cum draining from her closing rosebud. Ashley really did have an amazing ass, it’s too bad this was going to be his only chance to truly enjoy it. Refocusing on his situations and wanting to ensure that Antoinette got the blame she deserved, he sent the picture to Ashley with the caption, “Get some girl!” He was sure to throw in too many emojis so it’d look like one of Antoinette’s texts. He felt a thrill as Ashley’s phone chimed, he knew how self-conscious and guilt ridden she could get about sexual situations and this would be one of the worst yet.

He decided Ashley deserved to wake up in better situations than this. He pulled back her covers and manhandled both girls into the bed. He tried his best to wipe his dick off in Antoinette’s mouth but gave up and just used her face. Covering them with the comforter he grabbed their phones and put them on the bedside tables. As his adrenaline level dropped he began to get worried that Antoinette would remember enough to put the blame on him.

He opened up his phone and found the double penetration picture of Ashley. He sent it to Antoinette with the message “Hey, about last night. If you say anything about me, Ashley and the other girls will be getting this album posted online and sent to them. It’s best to keep this our little secret.” He heard Antoinette’s phone buzz, confirming her receipt.

It didn’t take long for him to get dressed and remove any sign he’d been there. He went so far as to clean up a bit so the true extent of their activities wouldn’t be known to either girl. His pictures were going to be a great memento of the night but he decided to grab Ashley’s panties too, just for good measure. On his way out he took the bag of pills from Antoinette’s purse, curious what she’d have to say for herself tomorrow. He started to get hard again just thinking about it. He shook his head and walked out of the apartment and headed home.

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