Skirting The Line

CW: Mentions of suicide, alcoholism, ****, cancer, parental loss and bullying.

Kim rested after her stream. The energy drinks had done wonders, but she was tired from both her performance and pumping load after load into Jennifer. She was not happy that Jennifer had managed to cum. But it was not like she had told her not to, so she did not think a punishment was in order… not for this at least.

She wondered how Jennifer was holding up. She looked over at her desk from her bed, the divider was moved away, showing off Jennifer's pussy still sitting there at the end of the reextended toy. It was caked in cum. Kim shuddered as she imagined having knocked Jennifer up. That would fulfil a great deal of her **** fantasies.

She had certainly improved her chances of that happening. Between a day of cumdumps into her and the side effects of the vibro-lube. Kim would say she had a fair chance. But it all really depended if Jennifer was ovulating or not. She would have to make this a regular occurrence to improve the odds. Maybe more streams, or just more raw cum shots in general.

Kim was certainly considering streaming more after having made close to 500 dollars, easily. She had been looking for a job before this to supplement her dwindling trust fund. With an income like this, she need not bother. She shut her eyes and felt weariness drift over her. She would just rest them for a moment.

Kim woke to the sound of a notification on her phone. She groaned as she opened her eyes to a dark room. It was some time at night. She looked at her phone. 2:13am. And there was a message from… Woody. Interesting. She opened it.

Woody: Hope I didn't wake you. Just got home. If you are up, can we talk? I could use a friend.

Kim blinked. That was… unexpected. She tapped a reply.

Kim: Sure. Come on down. Don't ring my door bell. It's too late. I'll be at my door shortly.

She got up out of bed and glanced around her room. Oh crap. She rushed over to the computer and grabbed the toy. She decided to deactivate the portal and collapse it into being the small, flat disk. Easier to hide. She put it into one of her desk draws under a notebook.

Her desk was splattered with cum having leaked from Jennifer's hole. No time to clean that up. Instead she just grabbed the divider and pulled it back across. She tore down her trans flag and shoved that into her closet. Clothes… she needed clothes… Kim had stripped out of her outfit from before and left it discarded around the room.

She rummaged about to unearth a pair of purple boxer shorts. She wore panties throughout the day but these were very comfortable some nights for sleeping in. She also pulled on an oversized blue sleep shirt with a snoozing sheep upon it. That would do.

Making her way out of her bedroom she glanced in her mirror along the way to the hall. She looked just like she had rolled out of bed. Only... She pulled the neck of the oversized sleep shirt down till she could pop one of her tits out of it. Woody deserved another peek and Kim enjoyed riling him up.

Reaching the door, she checked her new doorbell cam on her phone and saw a more dishevelled looking Woody standing there. He had bags under his eyes, he was unshaven with a five-o'clock shadow and was wearing the same clothes he had on the morning he left.

Kim opened the door and watched as his eyes went from squinting to wide open as he gazed down at her exposed breast. "Get inside," Kim grumbled as she reached out and pulled him in by the collar before closing the door behind him.

"Your umm… you… y…" Woody stumbled over his words as his face got redder and redder.

"Spit it out," Kim said as she did a good job at playing the fool. "It's 2am. No time for guessing games."

"Your boob is… out."

"Is it?" Kim asked, glancing down before shrugging. "It's 2am." She said again, as if that explained it away, but she did make a half decent effort to adjust the shirt till it popped back in.

"I'm sorry… were you asleep?"

"It's 2am and I look like this," Kim said, gesturing at herself. "You tell me."

"You don't look that bad."

"Thanks," Kim said dryly before sniffing the air as they stood close together in the hall. "You stink."

"Yeah… I have not had time to shower yet since getting back."

"Well go use mine," Kim said, shoving him down her hall. "I'll put some coffee on. Use the blue towel. It's fresh. Don't know what clothes I have that will fit you but you better not put those filthy rags back on or I will kick you out and you can come back at a decent hour, understood?"

"Yes Ma'am," Woody said with a mock salute before Kim shoved him again in the direction of the shower. She walked behind him but turned into the kitchen as he continued in through the living room and to the bathroom.

Kim did not have a plan, per se, but she did have two things that were better. Coffee and the ability to wing it. But most important was the coffee. Especially at this hour. She needed to be alert. She put on the kettle and went to look through her closest. What could she give Woody to wear?

None of her shorts, pants or shirts would fit him. Actually one shirt might. The one she was wearing. Oh… she liked that idea. She considered giving him nothing else but thought that might be a bit too much, too fast for him. Especially after his weekend. None of her pants or shorts were going to fit though.

There was one last option. She grinned as she pulled out her chosen garment. Was this too much? Nah, she wanted to see him sweat.

She walked her way out of her bedroom and towards the bathroom door. She could hear the shower running and she noticed Woody forgot to lock it. Perfect. Grinning ear to ear she knocked and entered at the same time. Sure enough, there he was, butt ass naked in the shower.

She could not see much through the fogged up class but he certainly noticed her enter and flailed about within there as he covered up his genitals only to wince as he covered them. "Kim! I'm not decent," He gasped out.

"So? Not like I haven't seen your cock before. It's not as impressive or secret as you think it is," Kim said she matched into the bathroom. "I have clothes for you."

"You can… um… leave them in here… if you like," Woody stuttered out. She swore even through the foggy glass she could see his red face.

"If that's what you want," Kim said as she casually reached down and whipped off her shirt. Woody gasped and even though he could barely see through the fogged up glass at her naked tits. He stiffly turned around. "Shirt's here when you want it along with something to cover up your not so secret, unimpressive dick."

"Don't you have any other shirts?" Woody asked as he kept his back to her.

"None that will fit you and besides, not like you haven't seen the girls before. They missed you," Kim said teasingly as she walked up towards the shower and tapped on the glass before purposely rubbing away part of the fog. "You have a cute butt by the way."

"Thanks?" Woody said as he glanced over his shoulder only to gasp as he saw Kim's face clearly though the patch she had rubbed along the foggy glass. He also saw the familiar outline of her naked upper body, including her breasts. He bit his bottom lip. "You can go now…"

"I can," Kim said with a nod before smirking as she leaned forward against the glass, pushing her naked breasts against them. Woody glanced away but not before staring for just a fraction too long. "I'll go make us some coffee. Take your time. Feel free to work out any… lingering frustrations."

Kim strapped back and turned away from him. She noticed his clothes on the floor and bundled them up. She found that his keys, wallet and phone were still in his pants. Oh that was an opportunity. Kim marched on out of there but stopped at the doorway to glance back, she caught him watching her and blew him a kiss before closing the door.

Kim dumped his clothes in her laundry basket before hiding it. She wanted him dressed in the ones she picked out for him, not back in these. She grabbed his stuff from the pockets and brought it over to the kitchen counter. She noticed his phone was nearly dead so she plugged it onto a charger near the kettle.

She remembered spying on Woody's phone pin. Although she did not see it clearly enough to remember exactly what numbers he used, she was pretty sure it was Jennifer's birthday. Kim pulled up Jennifer's social media page on her own phone and found her birthday. She attempted it and sure enough Woody's phone unlocked. She had to be quick, and listen to the shower, but something told me she had time on her side.

Inside the shower Woody was regretting his decision to come down to Kim's apartment already. It was a terrible idea. He should be avoiding her. Everytime they were together he got… urges. And she was not helping matters. The way she teased and flirted with him. His cock was half erect already. It only got worse when he noticed the impression of her breasts upon the foggy glass. How had she gotten that so perfect?

He could just imagine them in his palms. Just like they had almost been before he left. Even without that specific thought, Kim lingered in his mind. Her voice, her laugh, her touch, her smile, the image of her body, eyes, feet, hair, breasts… he was falling for her.

Jennifer remained his one and only. He was sure of that. But Kim was right here. She was playful, bossy, flirty and fun, like Jennifer in so many ways, but different. Whereas Jennifer laid down the rules and set the pace ahead of time. Kim seemed more free, or at least gave the impression of it. It was like she was willing to lead him on a leash, let him run and play but always ready to pull upon it and shorten it at any moment.

Woody felt like he was as dancing to two different tunes. Both were very fun and exciting but one was fresh and new. Whereas the other was… not stale… played out? No… there was more to Jennifer and Woody's relationship. They just had not reached that yet. Kim was so new in his life, she offered elements and experiences he had already had with Jennifer but in new lights and new ways that he never even imagined possible.

Not to mention that unlike Jennifer, Kim was not currently at the whims of someone with a portal literally connected to her holes. As much as Woody secretly enjoyed that… it was currently a difficulty in their relationship. A hardship that Jennifer was fighting to overcome and failing, while Woody… Woody felt powerless to stop it or help really. Deep down, he questioned if he even wanted to end it.

Meanwhile, Kim offered him something not burdened by that particular hardship. Though it put him in a rough spot. Cheating on his long term girlfriend with his neighbour while said girlfriend went through hell… it was not a good look and it weighed heavily on his conscience. That was if she even was going through hell…

The doubts that Kim put in his head around this whole situation still lingered. They were like poison. Slowly eating away at his faith in Jennifer. Everytime he heard her experiencing even a moment of pleasure as she was getting fucked, or saw her clearly getting off, the comment about that other cock being bigger than his…

That was not to mention the freak occurrence of the toy, she claimed she intended for him, getting lost. He had also noticed the way she seemed more guarded of her phone around him when he was with her and how it was buzzing so much that one night… it all made the doubts weigh heavier upon him.

He had to **** himself to turn the water off and get out of the shower. He had used Kim's floral scented soap. And the smell of it was familiar. He wondered if Jennifer used it, but knew she was not a fan of those scents. She preferred fruity aromas. He swore though that he had smelt something like this recently… and the only woman he had been closely around was Jennifer.

He banished the thought from his head as he grabbed the blue towel from the wall and dried himself off. He also borrowed Kim's deordient. A cherry blossom scent that he sprayed himself with. After a day in that run down motel and hours crammed into an economy seat on the plane, he needed it. Woody picked Kim's shirt up from where she placed it only for that other garment to fall out from within it. Those were not pants…

Kim had been busy. Going between searching through Woody's phone and making coffee. She was alerted when the shower switched off. Okay, it was game time. Any moment now she would be called for. She checked once more over his phone. She was up to date now on his conversations with Jennifer. They had talked a lot on the plane ride. It seemed Woody had upgraded to get WiFi. Maybe Jennifer gave him the money.

They still had no real strategy to deal with the portal and from the looks of it, Jennifer had not told Woody about Kim's contact with her. Good. Kim's make-it-up-as-you-go-along plan was working… she thought. She also noted that there was an apology about Woody not being able to fuck her ass from Jennifer and then from Woody him saying it was alright and he was just glad he could make her cum.

That explained a lot and confirmed some of Kim's theories. She also saw Jennifer venting her worries and frustrations about classes later today. That might be interesting to know. She did a quick search of their text thread for 'schedule' and sure enough Jennifer had sent Woody her class schedule a while ago. Kim snapped a photo of it with her phone, making sure it was legible.

The last thing she checked was Woody's text thread with herself. He had not deleted the photos she sent him of her tits. Neither of them. In fact, she found he had saved them. She grinned as she turned his phone off and put it aside. No more than a moment later she heard Woody calling for her from the bathroom.

"What's up?" Kim asked as she approached the door. He opened it a fraction and held out a white frilly skirt with the best elastic band in it that Kim had.

"These aren't pants… I think you got them mixed up," Woody said from behind the door.

"Nope," Kim said as she sipped her coffee cup. "None of my pants will fit around your bulky body. But that will."

"I can't wear a skirt."

"Why not?"

"Because their for women."

"Kilts."

"Kilts?"

"Are they for women?"

"No."

"Well they can be. Generally they are for both men and women. Or anyone else really. Just like skirts were for centuries longer than they have been considered to be gendered. Warriors, kings and even the simple labourers used to wear them. What's wrong with wearing them now? Especially just around my house. I am literally the only one here and I don't have a problem with it. Do you?"

"I guess not," Woody said, accepting defeat. "Is this really the only thing you have that would fit me?"

"Have you seen those muscular thighs? It was either skirts or dresses and I don't think you would fit well with those broad shoulders into one of those."

"Alright," Woody said, shutting the door. Kim retreated back to the lounge where she placed her own coffee mug down next to his. Moments later the door opened half way. "Don't laugh, okay?"

"I can't promise that, but I won't make fun of you," Kim said before she eagerly watched the door swing open and out stepped Woody. "Oh wow…"

He shuffled out and Kim looked him up and down. From his muscular thighs with the faint blonde hairs across his legs up to his muscular chest that was hugged nicely by Kim's shirt. She could see a great deal of his chest as the shirt had a deeper cut than the ones he wore normally. He was barely hairy at all, just some fine pectoral muscles.

Kim felt a pang of jealousy for his lack of hair over his body. She still had to get hers lasered off every so often to feel smooth and affirmed in her gender. Nothing against hairy women or anything. Kim just sought out anything to distance her own self from her former masculine traits. Woody looked half decent in those clothes. Even with his build.

"You make a fairly pretty lady in that," Kim commented and watched Woody blush.

"I thought you said skirts were for everyone," He mumbled as he stood there, shifting his weight, awkwardly on the spot.

"They are, but they do look better on women in my opinion, though feminine boys are almost as cute," Kim commented. "You could make either a very pretty lady or a cute femboy yourself."

"You said you wouldn't make fun of me."

"Who's making fun? Maybe I'm very serious. Either way, sit down and have your coffee," Kim said as she patted the couch next to her. Much to her disappointment he chose to sit on the armchair across from her. Kim frowned, okay maybe it would not be as easy to seduce him as last time. She giggled a little at the way he sat.

"What?"

"You're sitting very… masculinely," Kim said, her eyes locked down on the end of his skirt where his cock was poking out. "I see at least someone is pleased to see me."

"Oh shit… sorry," Woody exclaimed as he tried to shift around to hide his naked cock from her, only to wince as he brushed against the still sore member the wrong way.

"Sit on your balls?" Kim asked and Woody nodded to hide the real reason for his pain. "That can hurt pretty badly. Let me show you how to sit with a skirt." She demonstrated and noticed that he took a while to focus on anything other than her tits, which were still bared before him. Eventually though he got it. "There you go. Now drink your coffee before it gets cold."

"Thanks," Woody said, feeling strangely proud at having mastered sitting in a skirt. "I don't know how you women… and other skirt wearing individuals do this."

"It can be tricky. But they are very comfortable and fun. I'll show you the magic of spinies later. It took me a while to get them down. I still have some trouble with it depending on the length."

"Really? I would have thought you would be used to it, having spent your whole life wearing them."

"I wasn't allowed to wear skirts or dresses growing up. Not till I moved out and even then it took me a while to build up the… courage."

"Did your parents not let you or…"

"Something like that," Kim said vaguely as Woody sipped his coffee. "They're both dead now, so they can't stop me no more, even if they wanted to."

"Oh… I'm sorry."

"Don't worry. It was a while ago now. I was still in high school when they passed. I've been to a lot of grief counselling and I am over it… for the most part."

"For the most part?"

"Some wounds are still there. A lot of the… comments from kids in my class still linger… some in particular hit harder than others."

"Can I ask… how did they die?"

"Mum had late stage cancer freshman year, didn't make it more than a few months. Dad tried to keep it together after that but he fell apart. Drank so much that by senior year I felt like I was caring for him. He worked hard though. Made sure I had a roof over my head, food in the fridge, even if I had to cook it for both of us. He made sure to even leave enough money for me to buy this place and go to college."

"What happened to him?"

"Put his gun in his mouth and pulled the trigger."

"Jesus Christ!"

"He was nice enough to phone the cops before he did it and to do it while I was on the senior trip so I did not have to come home to that. He even sent an email to one of the teachers so I could be told properly. Too bad that someone else had stolen the teacher's phone that day and read it aloud to all of us."

"Damn… that's intense. And your classmates bullied you for this?"

"Not all of them. There was a ringleader. She kinda incited the bullying and anyone who dared to go against it or question her… they got it almost as bad, till they backed down. I never had any friends at school anyway, so it was not like I cared about any of them. I just put my head down and got through it. Then I moved as far away from them as I could."

"I can't imagine…"

"You really can't. But enough about me for now. What did you need to talk about? What happened? Did you fix Jennifer's problem?"

"Not really but I hoped I helped," Woody said and then relayed to Kim everything that had happened. He left out a lot of his actual feelings on matters but she pushed for them and even though he did not tell her the whole truth he got the feeling she could work out most of it. He had just finished telling Kim about how he had taken Jennifer back to the sorority house before racing to catch his flight when she looked at him with curiosity.

"Can I see it?"

"See what?"

"Your dick, Dude."

"My dick?"

"Yeah, you said it was sore and it looked a bit red before. So let me take a look. It could be a serious medical issue."

"I don't know…"

"Who else are you going to show it to? A doctor? That will be a fortune. Jennifer? Doesn't she have enough dick being shoved in her face at the moment? Literally? Just let me take a look and make sure it's nothing serious."

"I guess," Woody said as he shifted around and pulled up his skirt. His cock was soft but he was circumcised so she could see how red and raw it looked.

"That's got to be painful," Kim said, knowing from experience. She had explored herself sexually and learned how too much friction could cause irritation to one's cock. "I have some ointment that will help with that. Be right back." Kim got up and moments later came back with a tube from the bathroom.

"Alright, hand it over," Woody said, holding out his hand.

"No," Kim said firmly as she came down to her knees at the side of the arm chair. She opened the tube and leaned over the armrest.

"You don't have to…"

"I know," she whispered to him with a smirk. "But I want to." Her eyes glittered with mischief as she squeezed out a healthy amount right onto his cock. He cringed as it fell upon his cock.

"C-c-cold," Woody gasped, his hands digging into the chair arms.

"Oh poor Darling… let me warm it up," Kim said as she touched his cock with her hand. Her fingers spread the ointment out along his member as it slowly rose to the occasion. "How's that feel? Better?"

"The ointment's good," Woody almost purred.

"And my hand?"

"Fuck… it feels… very nice."

"Let’s aim for better than that," Kim said and she began to stroke his now slippery cock. She had some idea of what she was doing, having a cock herself after all, but this was a new experience for Kim. Jacking someone else off. "How am I doing?"

"Not um… bad," Woody moaned out as he bit his bottom lip. How had they gotten to this again? He had tried so hard to resist… or had he? Woody felt ashamed but also very turned on as Kim's hand worked up and down his cock. "Have you… done this before?"

"Not exactly," Kim admitted with a frown. "Any tips?"

"Well the lube is good… the ointment… makes things… easier… harder to fuck up. Your movements are a bit… inconsistent. Try to listen and watch how I react. Feel it. If you find something I react well to… focus on it, learn it, save it to use again later and try other things. Everyone is different and likes different methods."

"Ah. Like how you enjoy your girlfriend being pondered by cocks other than your own," Kim said and watched Woody shudder. She felt his cock twitch as her hand stroked him and little more firmly and he moaned. "Like that?"

"Ye… y… yeah," Woody gasped out as he was reminded of Kim's sneaky little vocalisations. "Normally I would say not to be afraid to be a little rough… but I'm a bit tender."

"Noted," Kim said as she eased up but found a steady pace. She watched him closely and adjusted her technique until he was almost melting into a puddle. She noticed how his hand closest to her was grasping onto the couch. "Here." She grasped his hand and shifted it to her chest.

Woody's eyes widened and his jaw fell open as his hand touched one of Kim's breasts. It was hardly the first time he had touched a woman's breast. But something about Kim's was different. Maybe it was because they were the forbidden fruit, not only behind Jennifer's back but bigger and dare he say better than hers. Or perhaps it was simply that she had teased him with the prospect of it over the last few days that when he finally got to touch them they felt more special.

Kim gasped as he touched her. His hand trembled as he fumbled her boob nervously. That big strong hand upon her made her shiver as his palm gave her a little squeeze, his finger brushed against her hard nipple and she moaned. Her own handling of his cock suffered as she became distracted but Woody did not seem to mind as he firmly groped her.

Both of them panted as they played with each other. They made eye contact. Him sitting there having his cock stroked while she kneeled there with her tit being played. It was a moment of passion between them. Intimacy with one another that left them both moaning and groaning. With a hiss, Woody's cock pulsed in her hand as Kim noticed his balls retracting. It was time.

"Going to cum for me Woody?" Kim asked as she moved her hand up to cup the head of his cock while her other hand came around to rub the shaft. He nodded with a groan. "That's it, cum for me, big boy. Let it all out. Cum."

On her command his whole body tense and he spurted out into her palm. She did not stop stroking him, if anything she started rubbing his cock more vigorously and rougher making him cry out as his tense muscles locked in place. "Kim! I… TOO MUCH!"

"Take it like a big boy for me. Come on. You can do it. Hold on," Kim cried out as his hand squeezed her breast like a stress ball making her whimper. She worked his cock till he was almost in tears from the overstimulation. "That's it… you did so well… good boy."

Woody whimpered as her hands slowed and he released her breast. He could see a red mark impressed upon her pale skin from his grasp. "Ohhhhhh… sorry about that," Woody said with a deep sigh as her hands left his well milked cock.

"Don't worry about it, I liked when you grabbed me hard," Kim said with a grin as she looked at her sticky fingers. They were slick with his cum. Long strands of it dripping between her digits. She could not help but have a lick. Mmm, thick and salty. She cleaned off one of her fingers and looked at him as he stared down at her in surprise. "What? You want some?"

"What? No…"

"Why not? Hardly the first time you have tasted yourself. Remember when you used to eat Jennifer out after cumming in her?"

"That's different… it's eating a woman out… my cum just… happened to be there…"

"You just told me about how you practically inhaled some strangers cum off your girlfriend's messy panties. How is this this that much different?" Kim asked and watched as Woody squirmed about. It was cute when he got embarrassed and uncomfortable. His cheeks flushed and eyes darted about.

"I guess not," he said, biting his bottom lip. "Am I going to regret telling you about that?"

"Probably," Kim said, smirking at her very true statement. "But don't worry. I won't use it for ****. Not unless it's for something sexy… such as now." She raised her finger up and offered them to him. He opened his mouth to object only for her to jam those sticky fingers in between his lips.

"Mmmpphhhh!" Woody exclaimed around him only for Kim to stare him down till he reluctantly licked at her fingers.

"Good boy," She praised and noticed how he practically purred against her finger tips. Her other hand reached down and rested on his thigh. "Skirts not only look good… but they have a wonderful quality of allowing… easy access." Her hand crept up his thigh before brushing against his soft cock. "Wearing them is not so bad, huh?" She watched as he suckled upon her fingers passionately.

"I guess," Woody gasped after she pulled her clean finger out from between his lips.

"And tasting yourself on my fingers?"

"Not the worst…"

"Imagine if it had been Jennifer's fingers you were licking clean after she jacked someone else. Or her pussy after being stuffed full of cum from that portal. Tell me you weren't tempted when it finally turned off to eat her out."

"I… almost offered," Woody shamefully admitted as his soft cock twitched against Kim's hand. "But worried it would be too weird."

"Boy you can't keep hiding your freak from her forever, you know. Keeping your desires hidden is not healthy for a relationship. Even if she's not into that, it will eat away at you both and form rifts between you," Kim advised though she felt like she was talking out of her ass. She had no hands-on experience with relationships. Not outside of whatever this was with Woody and Jennifer. And her single date with Raven too.

"Not the only thing I have to keep from her," Woody said, a darker expression coming on across his face. She could see the guilt and regret bubbling up within him. Kim knew he was too nice of a guy to not have those sort of feelings around cheating with Jennifer but she could not let him tell her about this, not yet.

"You could come clean," Kim said and watched as his eyes lightened up and he seemed to consider the idea for a moment. Her hand moved down and cupped his balls. "Only Jennifer will grab you by your balls and squeeze them, before twisting and yanking them off with her bare hands!"

"Ah!" Woody exclaimed as Kim tightened her grasp upon his balls. She did not squeeze them hard enough to hurt him but made sure he felt the pressure. "Point… mmm… made." He felt sweat drip down his forehead both from the pressure and the fact that Kim was probably more correct than she thought.

She noticed that applying pressure to his balls did not result in his cock getting harder. If anything it almost retreated up into him. It seemed he did not share the same fetish and turn on that Kim did around this. Good to know, she thought as she released her grasp upon his balls. He sighed and relaxed while Kim smirked. She shook her head as she took the tube of cream and placed it in his hand.

"Take that, use it once a day. Can you handle that or do I need to get myself a sexy nurse costume and come up to help you apply it?" Kim teased.

"I have it… unless…" Woody said as he eyed the woman knelt down next to him.

"Unless nothing you butt. Or do I need to get my hands back on your nuts?" Kim asked as she made a tight fist with her hand before his eyes. "Now get out of here so I can go back to sleep."

"Alright," Woody said and with a sigh he stood up. "Where are my clothes?"

"In the wash," Kim said as she too stood up but strategically moved around behind the chair to hide her ragging boner as it bulged through her boxers. "Come get them tomorrow… well tonight I guess, considering the time."

"But I…" Woody said as he looked down and gestured at the skirt. "I can't go out there like this?"

"Why not?" Kim asked with a raised eyebrow. "No one is going to be out at this hour. And even if they are… who cares? Tell them it's laundry day."

"I… suppose," Woody said slowly as he shifted about on the spot.

"Your phone is charging in the kitchen, rest of your stuff on the bench, close the door on your way out, I am going back to bed," Kim said as she turned her back on Woody and walked to the bedroom door.

"Right… I guess I'll bring your clothes back when I come to get my own tonight?"

"Sure. I'll make you dinner and maybe you can finish fixing this door?" Kim asked as she opened the lopsided door in question.

"Sounds good."

"It's a date then," Kim said and stepped into her room before closing the damaged door behind her.

Woody blushed at her words as his heart skipped a beat. He cursed himself for feeling this way as he turned around. Cheating on Jennifer physically was one thing but emotionally… it crushed him down even further with guilt. He trudged out to the kitchen, collected his phone, wallet, keys, and left the apartment.

Kim watched all this from her own phone both through the doorbell camera and several other security cams she had set up throughout her apartment. After what happened when she first met Woody… she was taking some precautions. Especially because she was playing with fire now, manipulating Woody and Jennifer like this. She needed to protect herself.

Thinking of that, she accessed the recordings for the night and looked over the footage captured of Woody in her arm chair getting a hand job. It was a great clip, showing him clearly but angled in a way that showed only Kim's back. She could edit around the rest of the footage if need be. She saved those recordings to her cloud drive. Time to get some sleep… but first… she was still hard and horny. She opened her desk drawer, searching for Jennifer's toy…