Mixed-Up Revenge Ch. 01

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Taking cheating ex's butt cherry, he gets a surprise.
1.8k words
4.51
309.5k
111

Part 1 of the 3 part series

Updated 10/31/2022
Created 06/26/2005
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Goldeniangel
Goldeniangel
12,563 Followers

Ray silently entered the unlocked back door of his ex-girlfriend Karen's house... Karen the bitch who had cheated on him with his best friend - supposed best friend - Ted. Karen who had told him how much she loved him, hinted at possibly getting married one day, and also told him that she wanted to wait till marriage to have sex. At 23 years old it wasn't exactly an easy wait for him, especially because he'd lost his virginity when he was 18 and then met her when he was 19. Although, you'd think that after almost four years that she would be a little more forthcoming, but no. And he'd respected her wishes, all the way up until he'd come over to her house to surprise her and found her riding his friend Ted. Not only was she not a virgin, like she'd told him, but she'd been cheating on him. For quite awhile... and although they had both begged for forgiveness, swearing up and down that they never meant to hurt him, he was filled with anger at her. Not so much at Ted, because as soon as he'd told Ted's girlfriend Chrissy, she'd not only dumped him but she'd kicked him out of their apartment - after cutting up all his clothes.

Sure it was kinda messed up, and Ted was going to have to pay a fortune to replace his wardrobe, but Ray didn't really care. At least Ted had payed for it. Karen still hadn't paid... all that had happened was that she'd lost Ray, and somehow Ray just didn't feel like that was enough. After all, if she'd really cared about losing him then she wouldn't have cheated on him in the first place.

Silently he went down the hall, dressed completely in black and with his dick already achingly hard at the thought of what he was going to do to his slutty ex-girlfriend. She'd promised him a cherry, and he was going to take one... she might not have the usual one left for him, but there was still one place he was quite sure was virginal. His dick throbbed at the thought.

At her door he stopped and began stripping - he wanted to be ready and raring to go in case she put up a fight, not hampered by trying to take off his clothes or anything. Quickly he lubed up his dick with the KY he'd brought with him... after all, he wanted her to pay but he didn't really want to damage her. When he thought his dick was slick enough he carefully began to push open the door, peering inside cautiously. There she was... laid out on the bed, face down with her head in the pillow; the moonlight played across her pale skin and he could see that she was completely naked. Her sheet was kicked off of her as she often did in her sleep, pale blonde hair covered her shoulders and she sighed in a dream.

Grinning, his hand wrapped around his dick, he quietly stepped to the edge of the bed, his eyes locked on that delicious ass and her sweet looking pussy. But her pussy wasn't what he was here for, it had already been violated, she'd given that away when it had been promised to him... and so he was going to take something else. Her little crinkled hole looked tiny compared to his dick, but that didn't stop him at all, in fact it just made him harder.

Crawling onto the bed he carefully positioned his dick at the entrance of her ass and started to push in; as she began to shriek and thrash on the bed, awakening to the cramping pain in her ass, he pressed her shoulders down, holding her in place. Her ass was exquisite, tight and warm, its walls slick with the lubricant that covered his dick. It rippled as she cramped and clamped down on him, massaging his dick as he began to press deeper, enjoying the feeling of her tight warmth. She was screaming and sobbing into the pillow as he buried himself, her voice muffled - not that he was listening to any of her protests anyway.

When his groin finally pressed against the smooth curve of her buttocks he leaned forward and allowed his hands to wrap around her body, grabbing her tits and massaging them as he whispered in her ear, "You promised me a cherry, remember Karen? You gave one to Ted, but I think I like this one better anyway... It's a lot tighter than that slutty pussy of yours probably is."

She gave another shriek as he began to move his dick back and forth in her ass, little hard jabs as he tweaked her nipples and tugged on them. Feeling her begin to squirm underneath him as he fucked her, he reached down to her pussy and found - to his utter shock - that she was wet.

Well, if that wouldn't be the ultimate revenge. Making the bitch cum with his dick up her ass... he stirred his fingers in her juices and she actually moaned and pushed back against him, her ass pressing against his body. Steadily thrusting in and out of her deflowered asshole, he began to toy with her pussy, running his fingers through the wet slit and rubbing her clit. The sounds she was making turned from pained to aroused and then to pleasured as he continued to fuck her and began to slide two of his fingers into her pussy.

He could feel his dick moving in her ass with his fingers, it was very strange and rather erotic, and he wondered how she felt with something in both of her holes. Rubbing her clit harder, he ground against her ass, making a circular motion with his dick and stirring her insides. Karen gasped and pushed back again, pushing herself up onto her forearms as he fucked her. With her ass high in the air she fucked him back, one of his hands gripping a hanging boob and the other knuckle deep in her pussy.

The room was filled with squelching and moans, her ass gripping him tightly with every thrust... this was the first time that he'd ever fucked a girl in the ass and he thought he might be addicted. It was a completely different sensation than a pussy... ok so it wasn't quite as wet as a pussy would be but it was still tight and slick, and there was something very base about it. He felt like he was doing something he wasn't supposed to be doing - and not just breaking in and taking her without asking - but the fact that he was in what was often considered the "wrong" hole. Fucking her harder, he realized he was going to cum soon and redoubled his efforts on her pussy, pressing against the small rough spot in her hole with his fingers.

When she came, it was completely unexpected for him, and he gasped with ecstatic shock as her ass suddenly began to convulse around him with her climax. It massaged him, gripping and pulling at his dick, as if it was trying to pull him deeper into her hole. Groaning, he managed to thrust one more time, burying himself as deeply as he could, before he began unloading his cum into her ravaged ass.

He straightened up, exhausted and surprised at the way she had responded - not that he wanted to get back together with her. Looking at the firm globes of her ass he regretted that they would never do this again, he liked the way his dick looked lodged in her ass. Panting for breath, she had her head down as his dick slowly shrunk inside her.

Turning to look over her shoulder she said to him, "You know, you could have just asked."

Ray literally fell over, his dick falling from her ass, as he recognized Karen's younger - but (fortunately) 18 year old - sister Charlotte.

*********************************

Later they would sit in the kitchen, both of them freshly showered and in towels... although he had just seen her naked Ray was still turned on by the sight of her in a towel. There was just something so erotic about a girl who was almost naked, but still covered.

Sipping her hot chocolate the younger girl told him, "You know, I thought that what she did was pretty fucked up... not that what you tried to do wasn't."

Shame-faced, Ray looked down at the marsh mellows floating in his cup, "Charlotte, I'm so sorry... if you want to report me to the police I'll understand."

He looked up, surprised at her sudden laughter. Giggling, she gave him a speculative look, "Ray, if you didn't know that I've had a crush on you since forever then you're totally blind." His jaw dropped and she sighed, "Ok, so boys are totally blind... anyway, I'll definitely be giving Karen my blessings for leaving me here to house-sit for her! The only way I'll be mad at you is if you don't at LEAST take me out on a date after this."

Totally stunned he stared at this gorgeous, sweet, ok so younger, but absolutely wonderful girl who apparently had not only not minded his invasion but had been excited and enthusiastic about it, and told his stunned brain that if he turned down this offer he was a complete and total idiot and should probably be cut out of the gene pool.

"I'd love to take you out!" he said, reaching across the table to grab her hand, "Now that it's legal of course." They grinned at each other, a little goofily. Then Charlotte's smile became a little more sinister.

"Of course, I do still think that my sister deserves a little payback for the way she treated you... can't have her doing that to any guy that's going to be worth dating me." She tossed her hair.

"Of course not," agreed Ray, not sure at all what she was talking about, but perfectly willing to go along with whatever she wanted. What had he been thinking all those years that he'd be dating Karen and not Charlotte? Oh right... that Charlotte had been underage.

Smiling, she leaned forward and his eyes couldn't help but travel down to her cleavage, "I think we can arrange something for when she gets home, don't you?" The towel slipped a little and he could feel his dick stirring, "And I can think of a few things to do in the meantime... can't you?" She got up and started walking towards the stairs, her delicious ass peeking out from underneath the hem of the towel.

As he ran up behind her - his towel fluttering behind him before landing on the floor - and grabbed her, she shrieked with glee as he picked her up and began to carry her up the stairs as they shared their first kiss.

Goldeniangel
Goldeniangel
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roveroneroverone2 days ago

Sheesh...you got some folks really riled up...

I've given a story here that involved rape a one before...gave this a 4 and fave-guess things just different enough...perhaps her younger sister thinking she's also a creep one factor...

PS-was already following author...

perhaps I'll also be smitten...or smited..not sure of the tense....(spell check hates it...)

Schwanze1Schwanze1about 5 years ago
Not sure if it was intentional

but the whole thing was over the top hilarious.

Fixated1Fixated1about 14 years ago
Looking forward

I thought this would be a run-of-the-mill tit-for-tat. Thank you for the twist, it was an enjoyable read and I'm "Looking forward" to the chapters to come.

MstangMch4MstangMch4over 16 years ago
nice Twist of Fate

Damn if that wasn't a nice unexpected twist. Instead of the evil Ex he got her sister & she liked it!! LoL Goldie i'm not sure which i like more, the naughtyness in your mind, or the talent flowing from your hands. Either way don't ever let it stop =)

AnonymousAnonymousover 17 years ago
Loved it!!

Ignore the PC crowd. Pay back should be a bitch. Anal sex is grossly underated. You write great stories, please keep writing

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