The Cucking of Jennifer Fucking Wilson

Kim had been busy. She had put on some laundry, for once done all her studying and assignment work due Monday ahead of time instead of last minute, called to check in with and lied to her family that she may not be available over the weekend since she was doing a massive study session, and even ordered dinner. She was working hard to make sure everything was set so she could spend her whole weekend with her new favourite toy from Jennifer.

She had even thrown out the package it had come in. But she made note of the return address. Maybe she would send Jennifer a present back. Though nothing would measure up to what she had gifted Kim. She wondered if she should reach out. Pulling out her phone she switched from the pizza delivery app to her social media app.

Looking up Jennifer, she learned a few things. She was attending the university in their home town. That made sense with the return address. Kim also saw that Jennifer was still cheerleading. Seemingly on a scholarship there, studying health science. There were a lot of selfies of Jennifer in those tight cheerleader outfits, Kim groaned as she saw the way they hugged Jennifer's tight body and the way her ass almost exploded out of that skirt.

Did she have time to go fetch her toy from the bedroom and blow a load into Jennifer before her pizza was delivered? She frowned as she noticed a few more intimate pictures with a man. Not a bad looking one actually. Athletic build, golden tanned skin, blonde hair and rather tall with pretty blue eyes. It appeared they were in a relationship. That made Kim feel… conflicted about the toy.

Was Jennifer cheating on him with her? Did they recently break-up and Kim was Jennifer's rebound? She checked Jennifer's relationship status and saw they were still in a relationship. It was not like Jennifer to fail to keep her social media up to date. Maybe he knew about this and was okay with it? Hell maybe he was into it. Kim was not one to kinkshame…

Woody was his name, but before she could go digging around his social media there was a knock at her door. Pizza delivery guy already? Talk about quick service. She hopped up and made her way towards the door.

She paused at the full length mirror in her hallway and checked herself out in the mirror. She was wearing a simple red flannel button up with her pink cloud pyjama pants. Nothing out of the ordinary for a Friday evening.

Kim paused as she looked at herself. She appeared exactly the same as she had this morning but she felt different. She looked and held herself so much more confidently and relaxed. She felt, honestly, sexy and, dare she say, flirtatious.

Thinking this, she let down her long brown from the messy ponytail she had had it up in, ruffled it just enough to give that girl next door look, and then undid quite a number of buttons on her shirt to show off her cleavage, she was not even wearing a bra, she felt like flaunting herself a little in front of the delivery guy. Maybe even flirting. Perhaps being daring enough to do something truly wild..

The knocking at her door became a banging. “I’m coming, I’m coming, hold your horses,” Kim called out as she turned and hurried down the hall. Her heart slipped a beat as she reached the door. She had never done anything like this before. Not, at least, after her transition, and especially not when she felt this confident.

All her attempts before transitioning to flirt with anyone had been hampered by a certain high school bully, who Kim now knew very well, both inside and out. She smirked at that thought as she opened the door and then recoiled in terror. Standing at her door was none other than the man from those photos with Jennifer. Her boyfriend, Woody, and he looked pissed.

“Where is he?” Woody demanded.

“Who?” Kim responded blankly as she tried to process what was going on.

“The guy who lives here!”

“No guy lives…”

“Don't play dumb with me,” Woody snapped back. “I know it came here. I know he lives here. I know he has it.”

“I don't… what guy?” Kim asked, her heart racing, as she tried to play dumb but was making some very worrying connections very quickly in the back of her mind.

“The guy who's fucking my girl! Stop protecting him!”

“Listen, there's no guy here,” Kim tried to persuade him. “Only I live here. You have to leave.” She tried to close the door on him. But he slammed his hand on it and **** it back open with his superior strength.

Goddamn female hormones! Kim cursed in her mind as he easily overpowered her attempt to shut the door. Not that she had ever been that strong to begin with. She looked terrified at him as he stepped into the doorway.

“I’m not leaving here till I speak to the guy and get it back,” Woody said, cracking his knuckles. “So just come out dude and let's settle this, like real men!” He called this out into the apartment.

“I'll call the cops,” Kim threatened before cursing internally as she realised she left her phone on the couch. “No one else lives here. Get the hell out of here you… you… you creep!” She tried to push him back through the door but that was as useless as her attempts to close the door in the first place.

“Good, call them. I want to talk to them about some stolen property and **** on my girl!” Woody said as he just barged in, straight by Kim, knocking her to the ground and storming into her apartment. “Hear that man! Cops are coming. You better get your ass out here before I beat you up. You're dead, you hear me? Dead fucking meat!”

Kim scrambled up to her feet and hurried after Woody into her tiny apartment. He knew exactly where to go, similarly familiar with the home. He pulled open a cupboard along the hall before slamming it closed. “Not in here… where the fuck are you hiding jackass?” He growled as he stormed down the hall, checking the kitchen on one side and then over to the living room.

Kim had no idea what to do as Woody pushed over her couch and then stomped over to the bathroom door. He kicked it open and started searching that room. She picked her phone up from the ground where it had landed. She considered actually calling the police but was that really a good idea? Had Kim actually broken the law by using Jennifer like that? She had not known at the time but… maybe she needed to call herself a lawyer.

Woody came out of the bathroom, slamming the door in his wake. “Only one last place left to hid fucker!” He declared as he turned and walked towards Kim’s bedroom door. “I know you are in there. You better fucking have my girls property ready to give back to me or I am going to beat you to a pulp!”

“Wait!” Kim called out as Woody reached for the door. She had left the toy in her bedroom, right out there on the bed. If he saw that and realised no one else lived here… Kim was going to be in a lot of trouble. He pulled open the door so hard one of the hinges came off. Kim really should run now but where even to? At this point he would probably catch up to her and then… she needed to do something.

Kim raced forward into the room and grabbed Woody by the shoulder. “Stop this…” She said as she skirted around him to stand in his way. His eyes were unfocused, rage blinding him, as he glanced around frantically. Did he even know what the toy looked like?

“Where is he?” Woody asked, quieter this time, the boiling anger in him turning down to a rage fueled simmer. He was still looking for only a guy. A big assumption on his part… good. Kim could work with that.

“Look,” She said, pointing to her open closet while keeping herself between him and her bed. She was not sure exactly how and where she left the toy on the bed, but she needed to block his view of it and put him off the trail. “See those clothes in there? All women's clothes? All my size? No man lives here… just me.”

“That's… but… I…” Woody stumbled over his words.

“In the bathroom… how many towels were there? How many tooth brushes ”

“One.”

“Any cologne? Men’s deodorant? Any stupid 3 in 1 shampoo, conditioner, soap?” Kim asked.

“No…”

“Look over here,” She said, taking him by his hands and leading him back closer to the bed but pointing him towards her night stand. “Look at these…” She pulled open the top draw. “Panties, bras, stockings, feminine socks… my underwear… no men’s briefs, boxers…” Kim sat down on her bed side as she watched Woody's eyes focused down on the draw and the contents.

“Ignore the condoms those are for if I do have company, which you will find are unopened and probably out of date so I can assure you, no man lives here or has been here recently. Only me. Kimberley.” She reached back while he was distracted, her fingers grasping around the toy on the bed, before she pulled it close to herself and hid it behind her back.

“Ohhhhhh,” Woody said, his face falling and head bowing. “I thought… I’m… oh dear god! I’M SO SORRY!” He turned to her and she stiffened, fingers still holding the toy, the only thing between him and the truth was her small form sitting on the bed in front of him. “I thought… I just… I flew into a fit of rage… I… did I hurt you? Are you okay?”

“I’m fine,” Kim assured him as his hands came to rest down upon her shoulders. “Maybe a little bruised bum when you knocked me down and scared out of my wits but beyond that… okay.”

“I’m sorry… I… I can't believe I did that. It was so wrong… I‘m normally not like this… I just… I’m sorry!” He wailed as he collapsed to his knees before her. “Please forgive me. I’m so sorry I laid hands on you and… scared you like that. I didn't mean to…”

“It’s okay,” Kim said a little too quickly as she felt relieved to have talked him around. She reached out and put a hand in his blonde hair before pulling his head down against her chest. Anything to block his sight as her other hand very carefully tucked the toy in under her pillow. “You were clearly upset and angry. You thought someone was here who… hurt your girl or something?”

“Y… yeah,” Woody said between sobs as Kim ran her fingers through his hair. She bit her bottom lip as he buried his face in between the valley of her breasts. Her shirt was so unbuttoned that he was practically getting a face full of her naked tits but his eyes werre closed as he sobbed. “Please don't call the cops on me. It was a mistake. I'll make it up to you. Please, I'll do anything, I am so very sorry…”

“Shhhhhh, Shhhhhh, Shhhhhh,” Kim soothed him as she continued to pat his head. What the hell did she do know? She had calmed the ragging beast, for the moment, but that could all change if he ever discovered the truth. Then who knew what would happen. She needed to make sure he never found out. “Woody?”

“Yes?”

“Do you like pizza?”

“That sounds really hard,” Kim said as she lay on her recently un-upturned couch, finishing off a slice of pizza.

At the other end of the couch, with her feet in his lap, was Woody who had demolished his half of the pizza and, between sneaking peeks down Kim's barely buttoned shirt at her boobs, had just finished telling her about what had been happening today. “Yeah…” He responded, his whole body slack on the couch. “She told me this hours ago but I had a test to get through this afternoon… I probably flunked it… I was just getting angier and angier, so by the time I got back here… all I could see was red.”

“I can't imagine what that would feel like,” Kim said as she flexed her bare feet against his thighs. “To have a girlfriend that loves and trusts you enough to send you something so precious like that… not to mention one who is sexually open enough to give you full access to literally her every hole! That is hot as fuck dude! You are a lucky bastard, you know that right?”

“Yeah, Jenny is one hell of a woman,” Woody said with the first smile Kim had seen so far across his face. “Better than any other woman by a mile.” Kim cleared her throat. “Present company excluded but she's still my number one.”

“Thank-you,” Kim said, smiling back at Woody. For a man who had been a ragging psychopath at her door nearly an hour ago, Woody was a pretty good bloke, easy on the eyes too, a little dumb, but sweet. “It sucks what happened with her package going missing. I'll keep my eyes out for it but you know how shit the postage system can be these days. I heard drivery drivers sometimes steal packages and not to mention porch pirates…”

“Fuck I had not even considered that,” Woody sighed. “Do you think someone in this building could have it? Grabbed it from your and my doorstep this morning?”

“Maybe, Woody, maybe,” Kim said as she tried to keep a straight face. “Seems a bit crazy to me to send something like that through standard mail but love can make you do crazy things, right?” His hand came down to rest upon her calf. “Or lust for that matter. How long has it been since you were both physical?”

“I moved here a few months ago after I transferred… I’ve been back once but… probably a month… month and half since we were together and could be… physical… a few weeks since we last had phone sex, I guess?” Woody admitted, a blush appearing across his cheeks. “I’ve been trying to um… save myself… for when we're together.”

“As in… you haven't been… relieving yourself without her?” Kim asked and giggled as the blush on Woody's face spread down his neck.

“Shut up!” Woody said, trying to stand up.

“No, no. I think it's sweet," Kim said, pushing his thighs down firmly with her feet to make him stay in place. "It's just… we all have urges Woody. Men, women, non-binary folks and other pals." She smiled at him and watched as he tentatively nodded his head. "Now, I've never been in a relationship…"

"Really? I would have thought a girl as nice as you…"

"Your turn to shut up!" Kim snapped back her face burning a little red too. "As I was saying… so I don't know how much I can speak on this buuuuuut I think it's okay to take care of such… urges by yourself, even when in a relationship, especially over distance." Woody mumbled something as his hand absentmindedly ran up and down Kim's pyjama pant leg. "Do you really think Jennifer has been saving herself for you? Like she hasn't rubbed one out at all without you? Not cum a single time since you last were together or had phone sex? Barring of course the incidents today."

"No… Jennifer is a bit of a slu… I meant she likes sex, and especially getting off," Woody admitted with a sombre nod. "Do you… do you really think she came today? Like when she got fucked in class by that sick bastared… did he make her cum?"

Kim did not think she had the strength to restrain herself from yelling 'I don't think, I fucking know she came at least once around my girl cock you stupid cuck!' But one look at Woody's sweet face with those sad puppy dog eyes gave her all the strength she needed to stand strong. "Dose she normally cum when you two have sex?"

"Um yeah… most of the time… I think," Woody said, shifting around on the couch awkwardly. “It’s hard to tell sometimes with women… they don't always make it obvious… she tells me she does… most times… but sometimes she has me eat her out afterwards or uses her vibrator to get off.”

“Mmmm and you didn't mind eating her out after cumming in her?” Kim asked, curiously. Her eyes widened as she felt something poke against the bottom of her soles. “Apprently not if the mere memory of it stirs your little friend up.”

“I’m sorry,” Woody gasped as he tried to shift around but Kim kept her feet in contact with his crotch. “I should… go.”

“What did I say about saying you are sorry?” Kim asked and Woody let out a whimper as her feet brushed against his boner through his khaki pants. “You don't have to go.” Kim looked at him from the other side of her couch with mixed emotions.

She felt guilty for what she had done to Woody, cucking him like that, even if it had been unintentional. And despite the fact it had been to save her own ass she also felt very bad about lying and deceiving him. Not to mention now pretending to hear him out and be a shoulder to cry on. Besides, he was a pretty cool dude and a sweet guy. Not to mention, very easy on the eyes. The only problem was, he was dating Jennifer…

That brought on a whole new range of emotions. What Kim had first believed to be the best apology in the world was nothing more than a missent package? Mmmmm. Her rage from years of torment and a teenage life ruined by that bitch bubbled back to the surface. Maybe some **** was in order and if she could make things up to Woody… why should she not give in and be a little naughty? If anyone deserved it, it was Jennifer.

"I have a girlfriend," Woody barely got out with a sound that was halfway between a whimper and a moan.

"I don't, or a boyfriend for that matter," Kim replied as she locked eyes with him while pressing down with her feet against his crotch. "But I'm not looking to have you as either. Maybe just a little fun?"

"I'm not going to cheat on Jenny…"

"Why? She already has some dude fucking her holes because she was too much of a horny slut to send them to you with a registered mail service or hell wait till you two were together to give them to you. Or maybe… well…"

"Maybe what?"

"Maybe it's less she just didn't care who got a hold of her holes and fucked them raw, and more she sent them purposely to someone else, and is feeding you a load of crap about this accidental wrong address bullshit, so when you are together she can enjoy some action with her side piece right in front of your eyes," Kim rambled as her feet rubbed gently against his growing bulge. His hands moved to grab them, holding them firmly in place, but he did not remove them from his lap.

"You don't really think… Jenny wouldn't really do that to me, right?" He looked so pathetically adorable as he stared over at Kim with this desperation that made her feel so powerful. Especially with his tenting cock between her feet. She wanted to step on him as his big blue eyes welled up and his bottom lip quivered.

"I don't know, never met her," Kim said with a nonchalant shrug. She scared herself how naturally lying and manipulating a man came to her. Talk about having her gender affirmed to her, she darkly thought as her toes curled and clenched around him to gently caress him through those rough shorts. "Have there ever been any signs? Has she ever cheated on you before? Fucked or flirted with another man? A woman even? What about wandering eyes? You said she likes to get off and you've been away from one another… could there be someone else?"

She watched as the doubt grew steadily in his eyes. A million little moments of worries and fears boiled into suspicion and paranoia. "Well… maybe a couple… more than a couple… it's… there's been some moments where I felt she was a little too friendly with some of my guy friends and I know things get… wild on some cheerleading camps," Woody admitted, his breath catching in his throat as he released her feet and let Kim continue to rub them at her pleasure against his throbbing cock. "And there was… once…"

"What happened Woody?"

"There was this football match we won, a big one, last year, not a final but it was against our biggest rival, the South…" Woody whimpered as Kim paused her movements, just letting her feet rest against his cock.

"Get to the good stuff Woody," she demanded and watched as he eagerly nodded his head.

"Right… so we won the match, and the boys and I went out ah… celebrating," He gasped out as Kim resumed toying with his cock between her feet. She had never done anything like this before but was quickly learning how much she enjoyed making Woody squirm by merely flexing her feet against his bulge. "We were drinking, partying, Jennifer showed up, it got late, she was the only girl there and well ummm…" Kim paused and Woody groaned.

"We got interment!" He squeaked out as Kim resumed her slow torment of him with her feet. "We were both drunk, horny and didn't mind the spectators… the rest of the team. One thing led to another and we… well Jennifer and I fucked in front of all of them but when I was… recovering and she hadn't had her fill… one of the guys asked me… I asked her… she said she was up for it… so I let him fuck her… and then the next guy… and the next… and soon the whole team was lining up."

"You ran a train on your girlfriend?" Kim gasped, freezing at the shock of learning that Jennifer Wilson fucked a whole college football team in one night. That was so fucking juicy. "What a fucking slut!" Woody flinched at Kim's words. "The whole team?" He nodded. "And she liked it?" He nodded again. "And you?"

"I…"

"Dude, I already know, I can feel your cock with my feet, it got hard as steel the moment you started talking about this," Kim said, flexing her toes against them again. "I bet you were ready to go again pretty soon after they started fuciking her, huh?"

"I took a few more turns," Woody groaned as Kim began to really run her feet up and down his fabric glad shaft. She was going harder and harder now as he whimpered and then winced. She stopped.

"Did that hurt?"

"No… well yes… it's just so dry and… rough."

"Do you want me to stop?"

He bowed his head. "... No," he murmured shamefully.

"Good," Kim said as he pulled her feet back and stood up. "Don't go anywhere, I'll be right back." She walked around the couch and through her half broken door to her bedroom before calling out from the next room. "And lose your pants before I get back. Underwear too. I want to see that cock I have been jacking off with my feet all night."

She heard him shifting around as she went rooting about in the bottom draw of her side table. Shifting past a couple other sex toys of her own she pulled out a bottle of lube. She also decided to grab Jennifer's portal toy from under her pillow and add it to her draw. A fitting place for a set of fuck toy holes like.

Kim smirked as she revelled in the feeling of vengeance against her teenage nightmare. She knew all of this was so fucking wrong but she really did not care. Maybe tomorrow she would wake up with it weighing on her conscience but for tonight, tonight she was going to fuck Jennifer fucking Wilson's boyfrined. She adjusted her pants to hide her bulge from him, that was something she would have to keep under wraps for now, lest he discover her greater deception.

Kim sauntered back over to the couch. She threw the lube at him and watched the football star catch it one handed. Her eyes went down to his crotch, looking at the cock that stood there, erect and ready. He was pretty impressive in size. Though Kim bet she was bigger, slightly, even after HRT. Still, it looked good on him, she licked her lips. "Slather that on your meat soldier and let me show you a good time," Kim said and watched as Woody eagerly opened the bottle before pouring it over his dick.

"Cold!" He hissed.

"Have you never used lube?" Kim asked and Woody shook his head. "Of course, it's cold you idiot, rub it along your shaft." She watched him do as instructed while she lay back down on the couch. "Good boy… now it's my turn." She placed her bare feet upon his cock once more.

"Ohhhh that feels… strange… good… but strange," Woody gasped.

"You're telling me," Kim said as she ran one of her feet back behind Woody's cock, hooking it around there while the other she flexed her toes around the head of his cock. "I bet you have never felt a cock on your toes! How's this feel?" Kim ran her feet up and down the cock, sliding them across the lubed up member. "You're twitching and throbbing… you must like it."

"Fuck I have never felt anything like this," Woody gasped out as he thrust up inbetween her feet.

"Stay still," Kim ordered as she pulled her feet away for a moment before returning them to his cock as he sat back down. "You just relax and let me do all the work. Just like Jennifer and her toy… let me fuck you with my feet." Woody groaned as Kim slowly lowered and raised her feet. "That's it, good boy. Just close your eyes and think of Jennifer… your Jenny. Remember what it was like to see her get fucked by that first man on that night last year. Remember what you felt as she was used by your team. Cock after cock plunging into her, over and over again. Tell me how much you liked watching her get used by them."

"I… it was so hot ahhhh… I never even knew… yesssssss… that I wanted to see her get fucked like that! Not till they were lining up… mmmmm… lining up to use her… it was so hot watching them all eager to fill her… and her moans… her moans… they sounded so hot. Fuck me! I never knew… I didn't know… I got so fucking hard wathcing her being fucked by other men!" He leaned back, eyes closed, body ridged, groaning and moaning as Kim slid her feet up and down his cock. He looked so helpless just laying there as she used him with, of all things, her feet. Kim felt like a queen extorting her power over him. She really wanted to see him cum at just the feeling of her feet.

"Imagine now how she felt this morning with a cock down her throat in that bathroom, sucking off some random, or not some random, dude. Do you think she really thought it was you? Or did she hope it was not? Maybe she knew. Knew she was sucking off some dude behind your back. I bet she thinks you'd be so mad if you found out… funny that it's the furthest thing from the truth. Right now you are getting off to the thought of her being fucked by other men. Not to mention what happened in class…"

Woody let out this adorable little groan through gritted teeth at this. Kim was very glad she had gotten him to close his eyes because there was no hiding her bulge at this point. She shifted around ever so slightly, making sure not to stop or disturb him too much as she freed a cushion from under herself and placed it over her lap. "... you remember what she told you about that, right?" Kim continued to prompt him as she picked up her pace. "Her pussy getting fucked by that other cock in the middle of class. All those people around her and she, your girlfriend, was getting fucked right there and then.

"Do you think any of them knew? Do you think one of them may have been the dude fucking your girl sneakily under their desk? Watching her quiver and shake with each thrust, making her cum right there and then around their bigger and fatter cock?" Kim felt him tremble between the soles of her feet while gasping. "Before they dumped a big load of cum into her. Has she ever let you cum inside of her?"

"N-n-n-no!"

"Mmm. Well sounds like the other dude gets to cum in her whenever they like," Kim groaned, as she remembered unloading straight into Jennifer's bare cunt. "Then she had to clean that cock up afterwards… well I suppose she didn't have to have to… what did she say? She felt like she 'could not hold back from licking the cum clean off of that stranger's cock'? Sounds like she just couldn't help herself to me… she just had to lick that cock clean… even knowing it wasn't yours, knowing what it had just done to her, she just had to clean it. I bet she loved tasting herself on it."

"I'm close," Woody gasped out as his cock twitched and his balls retracted a little. "Oh… oh yes… oh Jenny… yesssss!" Kim frowned as her pace slowed and Woody whimpered. "Please… just a little more… don't stop now!"

"Open your eyes Woody," Kim ordered in a gruff tone. "Open them and look at me or I will stop right here and now." His eyes snapped open and he turned to look at Kim. Seeing her laying there, feet wrapped around his slick cock as it glistened between them, cushion over her lap and fingers toying with the few buttons that were done up on her shirt. "What's my name?"

"Kim?"

"Right," Kim said and undid a button. "Not Jenny. Not your girlfriend. Keep your eyes on me, Mister. Who am I?"

"Kim…"

"Correct," Kim said as she popped another button and picked up the pace once more of her feet. "You watching me?" She saw him nod eagerly, almost in time with her feet as they slipped up and down his ridged pole. "Then moan my name, not hers, right now!"

"Kim!" He moaned and Kim rewarded him with undoing the last button of her shirt.

"I know you want to see them, I saw you eyeing them earlier, they're bigger than hers, aren't they?" She asked, already knowing the answer, and he nodded. "All it takes from you to see them is the magic word."

"Kiiiiiiiiim!" He practically shouted at her and she flung open her shirt to flash him her pale, naked breasts in all their glory. She was proud of how they had grown with the hormones. About the size of a decent pair of apples if she did say herself, still bigger than Jennifer's, and by the look upon her boyfriend's face, better too. Her rosy nipples stood at full attention as Woody's jaw fell open and he cried out as his cock exploded between Kim's feet. Take that Jennifer 'Cuck' Wilson, Kim thought with a satisfied smirk as she felt Woody rain down weeks of backed up sperm upon her glistening feet.