My Coworker Kim

Many thanks once again to my amazing editor, pamelacdnz for your invaluable feedback and advice.

I would strongly recommend reading the first story - The Christmas Party.

Chapter 1

Since Kim and I had gotten together, she had wanted to explore her kinkier side. Ben, her boyfriend, was averse to doing the things she wanted to try -- he couldn't call her the names, hit her or punish her the way she wanted. In Kim's own words, he couldn't treat her like the whore she wanted to be.

The first time I sent Kim back to her boyfriend with assorted red marks from a cane all over her body, Ben had been horrified until he realised just how proud she was of them. He still couldn't bring himself to inflict pain on his wonderful girlfriend, so this side of her was all mine.

Over time, we tried various things and discovered she really liked being restrained while I worked her over with a riding crop. Specifically, she loved being struck on her ass and thighs. We had all manner of spreader bars, cuffs, chains, ropes and crops of various materials and sizes. I had become proficient in lining up shots, making a nice line of angry red squares. We also discovered, quite by accident, that Kim can orgasm if she gets her pussy cropped in just the right way.

One night I had Kim restrained, lying on her back. Her wrists were tied above her head. I had her feet in a spreader bar and secured at the end of the bed. I had been marking my way up her thighs. She had been particularly difficult tonight for some reason.

"You've been a little brat tonight. Maybe I will mark your little pussy, so Ben knows who owns it." I said, gently stroking the crop cross her soaking slit. Her eyes burned.

"Daddy won't do that to his good girl. He doesn't have the balls to hurt me there." she said, emphasis on 'balls'. She just lay there, staring at me. Daring me to react.

"You wouldn't dare. You don't have the guts." Kim continued teasing.

"Ohhh, you little fucking slut. You're gonna pay for that." I said, tapping the crop on her pussy.

I adjusted the spreader bar to spread her legs a bit further and stuffed the ball gag back in her mouth. Her eyes widened as she realised I might just do it after all.

"Mbpfpfbf" she mumbled, shaking her head, eyes wide as I raised the crop.

Kim had a signal she could use if she couldn't speak, which had the same meaning as her safe word. She could plead and beg all she wanted for things to stop, but until she used that safe word, or signal, I was clear to keep going. I did stop before she used it occasionally; sometimes I knew she needed to stop before she did.

But this time, she hadn't given either of our agreed signals. I raised my eyebrow as I looked at her, giving her one last chance to back out. I was just about to stop when her whole demeanor changed, and she went from pleading for me not to do it and instead stared at me, daring me with her eyes to do it. I brought the crop down, hard. Harder than I meant to, if I am honest. I meant to start soft and work up, I don't know why I didn't. But my aim was spot on. The sound echoed around the room, but was drowned out by Kim, screaming into the gag.

"Mmmmmmmmmmmmm!!!" Kim screamed into the gag, eyes wide as she tried to bring her knees together, pulling all of the restraints so hard I thought they'd actually rip. Then, she started shaking uncontrollably. Hands clenching, thighs shaking, toes pointing as she tried to arch her back.

"Ughhghhh mbfmfbf!" She groaned into the gag, throwing her head back and clenching her eyes tight. Tears were running down her face, and I realised she was cumming. And she didn't stop, her orgasm continuing for far longer than I had ever seen. Once she had come down, I sat on the bed and removed the gag.

She just lay there for a couple of minutes, breathing heavily. Occasional convulsions wracked her body while she moaned quietly. While she was recovering, I loosened the straps holding her arms and feet, I undid the restraints of the spreader bar, and Kim rolled over into a fetal position. Eventually, Kim rolled onto her back and opened her eyes.

"Fuck!" Was all she said, breathing hard and staring at the ceiling. I sat on the bed and rubbed some aloe vera gel into her pussy, where there were deep red marks appearing on her puffy lips.

"I am so sorry, I didn't mean to hit you that hard." I said. "I meant to start soft and maybe work up to something harder."

Kim looked at me, eyes still wet from tears.

"I didn't think you'd do it at first, but then when I realized you were serious about it, something came over me, and I wanted to see what it was like." She said, still breathing hard. "I didn't think you'd actually hit me that hard, you fucking prick." She smiled at me, taking the sting out of her words, "and I certainly didn't think I'd actually cum from it. But fuck, that was the best orgasm I haveeverhad."

Kim looked down at her bright red pussy. "You fucking owe me for that." She said.

I did not argue the point; she was absolutely right. The next week there was a gift card, that pushed into 4 figures, for her favourite lingerie shop delivered with a huge bunch of native flowers to the office. "From Ben" of course, it would have raised difficult questions if they came from me. He gained a lot of brownie points from her colleagues that day at my expense. The important thing was that Kim knew who they were from.

But still she asked if we could explore that a bit more, obviously starting with lighter strokes. We figured out that it worked best if we got her very close to orgasm before cropping her with a strike that wasn't too light, but nowhere near what I'd done that first time. It's not something we did every time, even with the lighter stroke it did cause her a lot of pain, but she knew if she wanted it, she just had to be particularly bratty during our session and that was my signal to build her up then set her off with a single stroke between her legs.

Ben was not happy on those weekends. Her pussy was out of action the next few days while it recovered, but Kim insisted we keep it up.

Chapter 2

The other thing Kim said she wanted to try was fucking in front of people. She had a taste of this our first night together where we inadvertently put on a show for a couple in the room next to us while we fucked on the hotel balcony. That really got her pussy leaking.

She subsequently dragged me out onto hotel room balconies on multiple occasions to get railed, hoping someone was watching. We sometimes saw people watching from their windows. Usually guys, with their cocks out as they stroked to Kim being fucked. Kim put in extra effort on those occasions, being more vocal and animated, and always dropping to her knees to clean my cock after I'd cum in her. More than one guy painted his hotel, or office, window in cum on those nights.

Sometimes we'd go hiking and pop off the trail for a bit of fun in nature, the chance of being seen making her positively drip like a leaking tap. We picked trails that were not "family friendly", we didn't want to get arrested for screwing in front of kids. That would seriously fuck things up. There was a local group who hiked naked, and we went out with them a few times, but they were purely there for the hike -- not to play.

On occasion, she had even pulled me into changing rooms and either sucked or fucked me while people went about their business just on the other side of the door. A few of the department stores around our area had suspicious new stains on their carpet, thanks to us.

She'd tried to get Ben to explore this with her, but he was simply not into it. Making this another part of Kim I had all to myself.

While she enjoyed all of this, she wanted to try something a bit more explicit. She wanted a room full of people to watch her have sex. She wanted to completely expose herself and let them watch as my cock plundered her wet little pussy. And hey, if it meant a group of guys got to watch me fucking and cumming in this brown eyed goddess, who the fuck was I to argue?

So, we ended up deciding to go to a sex club my wife and I had visited one time, where Kim was going to try putting herself on full display. What I didn't tell her is there was also a BDSM dungeon in the lower level of the club where I was planning something special for her involving restraining her to a cross, or maybe the chain hanging from the ceiling, and working her with a crop, before finishing her with a single stroke to her pussy in front of everybody. Showing everyone what a horny little slut she could be.

I noticed the club had a beginners night coming up, which would be perfect for Kim. I let her know, and she confirmed she was free that weekend. I booked the hotel, got some tickets to the club, and looked forward to the night.

Chapter 3

We were at the hotel getting ready. We had a nice, light dinner and came back to shower and dress for the club. I waited until Kim had done her hair and makeup before hopping in the shower. I loved being male -- wash everything with the same bodywash, dry and get dressed. Simple.

I walked out to see Kim in what was apparently passing for her underwear for the night.

"Fucking hell, Kim. Why bother?" I asked, amazed at the sight before me.

She just grinned at me. "If I'm going to be a slut tonight, I may as well dress like one."

She was wearing the tiniest black string thong, the material barely covering her puffy pussy lips, stopping just at the top of her slit. She'd shaved the little bit of hair she usually kept there, which was a good thing as this thong would not have even touched it. The rest of the thong was, quite literally, string. If you've ever seen traditional Wicked Weasel micro-bikinis, this was smaller than those. The material, what little there was of it, was completely see-through and already soaked.

Her bra was not much better. Tiny little triangles of completely see through fine mesh left absolutely nothing to the imagination. Luckily, Kim had fairly small areola, but even so the material didn't completely cover them. Her little nipples, currently hard, were trying their best to poke through the thin material. Interestingly, instead of the straps going over each shoulder, the strap from the left crossed her chest and hooked into the rear of the bra on the right.

She had her long brown hair done in one single ponytail; a black ribbon tied in a bow holding it in place.

Finally, she was towering over me in a pair of sparkly black hooker heels. These added at least 4 inches to her height.

It was already looking doubtful as to whether we would make it out of the room, then she grabbed the dress.

At first, it appeared to be a simple, black dress that had the same kind of crossover for the straps as her bra. Once she had it on, it transformed. It hugged every curve, enhancing her already amazing body. What really set it off though, was the length. If Kim was standing straight up, with her shoulders back, it stopped literally just below her ass. If she slouched or leaned forward even the smallest amount, the dress pulled up at the back and you were left staring at her firm, pale, perfectly rounded ass. If she slouched enough, you might see the black string from the thong. If not, you'd wonder if she was actually wearing anything under the dress.

"Oh, fuck me, Kim! You joke about killing the old man. Nothing you've tried yet has done it, but damn! That dress might just fucking do it." I could not take my eyes off her.

She didn't appear to be wearing any makeup, but she was skilled at rocking the "natural" look. When she wasn't going for a goth / punk vibe, that is. And tonight, it was natural. Probably a good choice, knowing what I had planned in the dungeon. Her makeup would be ruined after a few strokes of the crop.

Kim walked over to the bed, placed her feet shoulder-width apart and bent at the waist, putting her palms on the mattress. The dress rode up showing off the entirety of her perfectly firm, round, white ass. The piece of string dipping between her cheeks. I swallowed as my mouth went dry, wishing I was standing directly behind her. That view would've guaranteed we didn't get out of the room though. She looked back over her shoulder.

"Does daddy approve of his little cumslut going out in this?" She asked sweetly, wiggling her ass. My mouth went from dry to positively salivating in a heartbeat.

"Ohh, we'll be lucky if we get out of this room." I said as she straightened and turned.

Kim sauntered up to me and grabbed my cock through my jeans, causing me to groan.

"Well, I guess we should go then. Is the ride here?" She asked, squeezing me.

I checked the app and saw the taxi was about 5 minutes away. "Yep, we should head down now. Are you taking a jacket or something?" I said as I grabbed my bag. Kim just shook her head and headed for the door. Fuck, she was really going to go out dressed in that.

I had packed a few things we'd need into the bag. A couple of bottles of wine, her favourite crop, and a few other restraints we might need. Although the club had most of the things we'd need, it paid to bring your own. At least you knew it was clean, and in working order.

"Care to tell me what's in the bag?" Kim asked.

I just smirked at her, picturing her in nothing but those heels, tied to the cross.

"You'll find out later." Was all I said. She shot me a look I couldn't quite read.

Kim hooked her arm through mine once we were out of the room. Having Kim hanging off my arm always made me feel like a king. Having Kim in this dress hanging off my arm? I could conquer the entire fucking world.

We took the lift down to the ground floor. Once the doors opened, we stepped out; Kim's heels clicking on the tiled floor as we walked across the lobby. The head of every guy in the place snapped to stare at this brown eyed brunette goddess. Quickly following the males came the eyes of all the women. A mixture of shock, disgust and envy on every one of their faces.

Damn, it felt good. I felt Kim stick out her chest a little bit more, she obviously felt the same. That, or she was trying to make sure her ass wasn't entirely showing. I wasn't sure that it helped that much, if it helped at all. The motion of Kim walking in the heels did cause the dress to flap, flashing her ass cheeks.

The taxi pulled up just as we exited the hotel. I opened the rear door and held it for Kim as she got in and scooted across to sit behind the driver who had turned to welcome us, but got quite a different welcome, getting a clear crotch shot as Kim spread her legs to move across the rear seat. His eyes bulged as he got a clear shot of my mistress, and her completely sheer panties. I saw him swallow, hard, as I hopped in.

"Hey mate, how's it going?" I asked, pretending like Kim hadn't just flashed her pussy at him.

"I, uhh. Yeah." He said, recovering and moving out into traffic. "Much better now, if you don't mind me saying."

"She is a sight, isn't she?" I asked. Kim rolled her eyes and looked out the window, smiling. She loved the attention and I knew it.

"I'll say." He said. "So, you two going to the club?"

"Yep. I've been with my wife and now taking the mistress." That caused his eyes to flick up in the mirror. "You ever been?" I asked him as his eyes returned to the road.

"No." He said, sounding disappointed. "My partner isn't into that kind of thing. But I get a lot of fares to and from there. Looks like a fun time."

"It is. It's a pity your partner isn't into it."

He just grunted disappointedly. Point taken.

"Say, it gets busy later in the night." The driver said. "If I give you my card, you can send me a message when you're ready and I'll come get you guys. You can bypass the call center that way and get home quicker." Completely ignoring the fact that we'd booked him via the app.

Clearly, he wanted to see more of Kim and maybe get some details of her adventures in the club. My deviant brain got to planning a way to get a free taxi ride. Well, free for me at any rate. Kim would be paying, but not with cash. If she was up for it.

"Sounds like a plan, thanks mate." I said.

We pulled up and he got out as soon as I'd paid, opening the door for Kim. Taxi drivers never opened doors for people, and we all knew it. Kim obliged by getting out of the taxi in anything but a lady-like manner. She spread her legs wide to step out, giving him the clearest view yet up her dress to her soaked, sheer panties. She "stumbled" against him, leaning against him for support as his hands went straight to her ass.

"Oops, sorry. Had a bit to drink already!" She quipped, regaining her balance and heading for the club door. I knew it was bullshit; she was stone-cold sober.

"Enjoy the tip." I said winking at him. He swallowed hard again and did not take his eyes off Kim's ass until she walked through the door. Kim made life easy for him, rolling her shoulders forward, pulling the back of her dress up above the bottom of her ass. Combined with the wind, and Kim strutting in her heels, he got a few good glimpses of her bare ass. He blew out his cheeks and shook his head as he closed the door and moved off to his next fare. Or, to park around the corner and take care of the tent in his pants.

Chapter 4

Stupidly, in our State, a club can't serve alcohol if there is sex on the premises. Such a dumb fucking rule, but you could still BYO. I grabbed the two bottles of our favourite wine from my bag and handed them over at the bar, receiving a marker for them. I handed the bag over as well as it wouldn't fit in the lockers.

The girl working behind the bar was a cute little redhead. She was wearing a deep green corset, wonderfully setting off her bright green eyes. Her hair was in tight ringlets, hanging down either shoulder. She appeared to have slightly larger tits than Kim, but it could have just been the way the corset pushed them up. I couldn't see much else given the height of the bar, but I did let my mind run wild.

She offered a glass, but we said we'd poke around first. She looked Kim up and down, eyes sparkling, clearly eye fucking her. Kim blushed slightly.

"I hope I get to see a bit more of you later tonight." She said, licking her lips. Kim blushed a deeper red. She'd never expressed an interest in women, but I did wonder sometimes. Seeing her reaction to being blatantly hit on really gave me pause.

"Maybe I will have a glass, please." Kim said. The barmaid cracked a bottle and poured a large glass for Kim. She looked at me questioningly.

"Oh, go ahead." I relented. I never could say no to a cute redhead.

We took our wines, and I led Kim around the club, giving her a quick tour. Just past the bar / reception were a couple of pool tables.

"Maybe you should play a game. You'll give anybody behind you a heart attack." I said, squeezing her ass, making her jump a bit. Kim giggled, sipping her wine.

Past the pool tables were some leather couches; a few couples sitting on them chatting. The men, and some of the women, all stealing glances at Kim. Next there was a dance floor, it was empty as the DJ didn't start up till later in the night. We headed up the stairs beside the dance floor. These stairs were fairly narrow; you could pass people on them, but it did get a bit intimate. Naturally, I pushed Kim ahead of me so I could look up her dress.

"Fucking perv." Kim said, kissing me as she moved past.

"I'll tattoo that on your head one day!" I teased as she started up the stairs, putting an extra sway in her steps, taking my breath away.

At that moment, another couple reached the stairs. Being "polite", but really just wanting to show off Kim, I waved them ahead of me with the guy taking the lead. I saw the guy look up, and freeze. His partner ran into his back and popped her head around him to see what had caused him to stop dead in his tracks.