Karen's Challenge

The mood was festive as our team of four sat in the Applebee's close to the airport and drank to the closing of the deal. I stared at Karen with a smirk, wondering if she knew what I was so happy about.

In one late-night strategy session, we sat around wondering how we'd go about acquiring the Reynolds' small company. George Alistair Reynolds had proven a hard nut to crack, but while everyone else saw a small, inconsequential figure in his son, I saw an opening and suggested we work through him to convince Dad to sell. No one scoffed at my suggestion more than Karen, who laughed and exclaimed crudely, "Yeah, right. If that works, I'll get down on my knees and blow you!"

I jokingly responded, "Well you better start licking those lips Karen." The other two were shocked at our crude banter, but Karen and I had that type of friendship. It was, I expected, promptly forgotten; except by me. The fantasy that surrounded my relationship with my co-worker and friend had started that day with her snide comment. I understood that it was only just a fantasy though.

Karen was a happily married woman. Her and Eric had been married for twelve years and had two boys. She had gained some weight with Timmy, her second child, which brought the quiet, behind the back criticism of her male co-workers. I thought that was shameful and unprofessional. Besides, she had been 120 pounds for most of her life. I always thought she could stand to gain some weight. The extra twenty pounds, I thought, made her more voluptuous, especially considering the extra heft added to her formally athletic, relatively flat chest. To tell you the truth, it only made me fantasize about her more. It helped that many of her outfits for work had filled out and when she moved just right, you could see a lot more of her.

I looked over at her in the passenger seat on the way to the hotel and smiled. I caught a glimpse of her flowery bra showing through the exposure caused by her unbuttoning the top button of her blouse. The gift of flesh almost made me drive off the road as we moved our celebration from the Applebee's to the hotel bar. When she flipped her brown locks to press the phone to her ear, I could smell that alluring Chanel and it drove me closer to insanity. I watched her mouth move as she described our success to Eric and told her kids to be good. The great view only got better after she hung up. Karen turned to joke with the guys in the backseat, Harold and Turner, and I had a perfect view of her stockinged legs, her left one now pulled up in the seat. I reluctantly pulled myself away to make my own phone call prior to heading into our hotel.

Turner, an older African-American gentleman, excused himself almost immediately upon leaving the car. "Too much beer will make our flight home tomorrow a headache--literally." So it left me, Harold, or Hank to his friends, to escort the lovely Karen to the hotel bar for some more drinks.

The bar was pretty empty and dimly lit. An older Korean lady served the drinks from behind the long bar, though she seemed annoyed to have to put down her cigarette to do it. She seemed even more annoyed when we loaded up the jukebox with tunes. We could hardly care about her ire as we recounted our success. It was genuinely a great time. Harold risked that when he suggested old man Reynolds only agreed to the sale because he wanted to get into Karen's panties. The suggestion and the blatant use of the word "panties" took us aback, especially coming from the normally reserved Hank. Karen and I were the younger of the four and decidedly less refined in our professional demeanor, so hearing him say something like that was stunning a bit. Even so, we laughed at what he said, and continued celebrating.

Hank surprised us again when he held out his hand to Karen and asked her to dance. Karen looked at me and I gave her a "why not?" smirk as I put he the lip of my drink to my lips to cover my smile. Hank was not a small man. Many nights on the road eating fast-food meals before turning in had made him pretty overweight. His drinking tonight had made him sloppy. Even so, he had some pretty sweet moves on the dance floor which left us both impressed. It became even more interesting, though, when the music slowed. I laughed quietly and Karen looked back at me and smiled when Hank, Mr. Conservative himself, slipped his hands down her back and over the skirt that covered her ass. Slipping slowly into a drunken stupor, he was showing more and more of his figurative ass by holding Karen's. Much to my surprise, Karen just let him, at least initially.

By the third song, Hank's eyes were half-closed and it was very apparent that he was almost done for the night. It didn't stop him from running his large chubby hands further down until he finally cupped both of Karen's ass cheeks. Karen had been a good sport, but this was getting out of hand. She smiled politely and pulled one of his hands off and Hank promptly moved it to her breast. I stood up to break it up, but surprisingly got a wave-off from Karen, whose mouth opened in a quick inhale of surprise. Hank was lucky, first, to not get smacked, but second, to have his hand on one of Karen's luscious B-cups.

Hank finally crossed Karen's line, though, when he had slyly unbuttoned two more buttons on he blouse and attempted to thrust his hand in her shirt. She finally registered some annoyance and I quickly came in to grab him. Hank acted pretty surprised by the slight shove he got and my hand now on his shoulder. His eyes got big as if he suddenly realized his indiscretion at the sight of Karen rebuttoning her blouse. I mouthed "Are you okay," as I got under one of Hank's huge arms to steady him. She shrugged and smiled back at me as if to say, "no big deal," even though it was.

I held up a fifty to get the Korean bartender's attention which she answered with an angry scowl and put it on our table. I then began escorting Hank to the elevator and then to his room. Karen, in a display of utter kindness in light of what he had just done, took Hank's other arm, draped it over her shoulder and began helping me with the effort. Hank just shuffled along with his head hung forward.

We made it to his room and finally found his key card. By this time, Hank was mumbling loudly something about his ex-wife. He continued after we laid him on the bed. Karen and I stood at the end of the bed and just laughed at him. "So, you going to press charges?" I asked her.

"No, he's harmless. Just lonely and had a little too much to drink." she replied.

I couldn't stop the quip, "You or him?" She laughed and playfully pushed me. The physical contact, even as meaningless as her shove, felt nice. We both turned and walked toward the door when Hank allowed himself one more asshole act for the night. He sat up slightly and said with an eerie nonchalance, "Hey Karen. When you give Randy that blowjob for closing this deal, I wanna watch." He then went to sleep.

His statement left an uncomfortable silence between Karen and I for a couple of seconds. I had to rescue our good rapport quickly so I said, "Hey Karen, don't worry. I'm not holding you to that." The recovery worked because we both laughed heartily, if only to mitigate the awkwardness.

We walked into the hallway and I asked, "So, we going down to the bar again," hoping she'd say yes so I could at least try to match Hank's earlier efforts.

She unfortunately answered looking at her watch, "It's eleven-thirty. Our flight's not until four in the afternoon, but I want to go to the gym, take in all of our success over our delicious free continental breakfast." Her sarcasm did not escape me. I wished her good night and resigned myself that a romp with Karen would remain a fantasy. I'd have to rub out my frustrations in the shower tonight.

I turned on the television and watched SportsCenter as I removed my slacks and got to the third button of my shirt when I heard a knocking. I hadn't really thought about it, but it was the first time I'd noticed that Karen and my room were joined by a door between rooms. We'd been booked rooms normally reserved for families. I looked down at my boxers and thought that my appearance was pretty harmless. I turned the deadbolt and swung open the door.

Karen stood in front of me still wearing her high heels, skirt and blouse. She had unbuttoned the blouse to where Hank had previously had it. It looked like she was getting ready for bed. She asked, "Hey, does your hot water work because mine doesn't really?"

"I haven't checked it yet, but you can." I replied. She walked past me with her alluring Chanel tantalizing my nose and into the bathroom. She fooled with the water while moved to the head of the bed and promptly placed a pillow over my growing cock.

She came out of the bathroom and stated, "I may have to use your shower if that's alright. Yours seems to actually work." She paused for a second and looked at the sports highlights on TV as if trying to buy time. She then said softly, "I'm sorry to bug you but I'm not tired and wouldn't mind the company if you don't mind. Besides, it'd be nice to sit with the man of the hour."

"What do you mean by that?" I asked.

She then said as she sat at the office chair that faced the television, "I have to hand it to you. I really thought we'd hit a dead end and so did the rest. Your analysis and approach really sealed the deal. I'm very impressed.

"Whatever! Lucky guess Karen." I replied.

"Yeah, but this was our biggest acquisition." she responded.

"Well thanks. Coming from you that means a lot. You seemed to have gotten the most out of our celebration though." I said.

She looked at me confused and then it finally registered. "Oh! Yeah. Yay, I got felt up by an old fat guy!" Her laughter at the very bad events from earlier made me laugh too.

"It was wrong Karen; and inappropriate. You're a better sport about it then me." I said, feeling a little guilty about dreaming of pounding away at her with my cock.

"To tell you the truth, it's the most action I've seen in months. Eric's been a little weird since Timmy came." She admitted.

I was stunned. Mostly at Eric for leaving Karen unfulfilled, but more that she had admitted it to me. "Karen, I'm really sorry." I scooted toward her and put my hand on her back. "Any guy would jump at the chance to..." I stopped myself. I was about to go down a very bad road.

"What?" Karen asked.

"You know." was my pathetic answer.

She smiled and said, "Thanks. You are really sweet to me Randy. I bet you and your wife never have dry spells."

"Karen, marriages are tough. All of them are." She looked really sad now and I was hoping to keep her from crying. "You just have to keep trying," I urged.

She then said, "It's tough though. It's like he's in another world sometimes. I try to be sexy for him, but it's like he's not interested since our second baby came. Maybe it's me. I've gained a little weight..."

I interrupted her. "Karen, I can't speak for your husband. But your weight is not an issue. Trust me. It hit all the right places. Truth is you're pretty freakin' hot. Hell, I wish I had been dancing with you tonight." I was appalled that I had let that slip.

Karen blushed and responded, "Yeah. I wish you had too." She took a deep breath and stood up. "I've got to get to bed. To tell you the truth, for a number of reasons."

I looked at her confusedly. I wasn't sure what she meant so I decided to ask. "What does that mean?"

She turned and stared me right in the eyes. "Uh, better not say." I knew then what she meant. She would have told me that if she stayed, then something bad, or "good" depending on your perspective might happen. She moved toward the door between our rooms and stopped before leaving. She casually turned to me and said, "I almost forgot. I have something for you in the other room for the great job you did on this acquisition."

I look back now and can hardly believe my naïveté. I got up and followed her into her room. She went to her suitcase and flipped it open as if to look for something. She told me to have a seat on the bed. I tried hiding the growing tent in my boxers. Just being in her hotel room, the late hour, the fantasies I kept in my head of her...it all amounted to a growing sexual tension.

She turned around and threw a pillow down at my feet. As she knelt on it, she looked into my eyes and said, "I'm sorry I didn't believe in you. You were right and I was wrong. I said I'd do this if you were right and you were. I think you deserve it." My mouth dropped open. Karen parted my legs at my knees and scooted between them. She reached out and pulled down my boxers to my feet, freeing my hardened cock. She quickly grabbed the base of my seven inch dick and stopped to look up at me. She licked her lips and then asked me just above a whisper, "Do you want me to stop?"

I, of course, did not. I think I was so in shock at the turn of events that I only gave a quick shake of my head. With my approval, Karen smiled and stuck the tip of her tongue out. She began to lick the base of my cock's head slowly. I leaned back on the bed and watched as she began to lick the entire length of my seven inches, from my balls to the tip. Karen let a lot of saliva drip from her tongue and used it to wet my entire shaft. She then expertly used the palm of her hand to rub the underbelly of my cock, making it nice and wet. She looked at my face and giggled a bit, perhaps because of the goofy surprised look I was no doubt expressing. "I've been needing to taste this dick for awhile," she said. Her dirty words made my cock jump as I imagined what she'd do next.

It caused a small droplet of pre-cum to appear. She wasted no time dipping into it and extending the sticky substance out until the string broke and landed on her chin. She giggled again as she took her finger, wiped her chin, and sucked its tip clean. Karen stood my member straight up and began to move her tongue up and down its length a number of times. Finally, when I was to a point where I was writhing in ecstasy, she opened her mouth wide and engulfed my engorged cock's head. She held it there for a few seconds, sucking it a little harder than I liked. But then, she began a gradual descent, slowly swallowing more and more of me into her mouth.

I had known Karen for four years at that point. We shared a playful, flirtatious relationship, but it was innocent for the most part. Occasionally, we skirted the professionalism line. Looking down at her attempting to swallow my cock, though, said we'd taken our relationship, personal and professional, to a different level. The realization of my occasional sexual fantasy was one of the greatest moments of my life. It only got better as the tip of my cock reached the back of her throat and she stuck out her tongue to rub the front of my balls. Karen was determined to take all of me and she did. It was hard to get over that Karen, my friend and co-worker was sucking my cock and doing it better than any woman who'd ever performed a blowjob on me. While she did, I took off my dress shirt and t-shirt and now lay naked in front of her.

Then, her cell phone rang. I thought for sure that she'd let it go to voicemail, but she said, "Oh shit, that's probably Eric checking up. Stay right there." So I did lying back on her bed with my dick wet with her saliva. I listened as she talked about getting ready for bed, missing him, et cetera. She sat at the desk chair, with her feet propped up on the room's little coffee table. Her blouse was unbuttoned so I could see the center of her bra. I looked over at her and began stroking my cock. Our eyes met and she smiled, showing her appreciation of my actions. She then turned up the heat.

While still on the phone, Karen stood up and reached under her skirt and pulled down her pantyhose. I quietly watched as she then removed the skirt, leaving her in a pair of silk panties that matched her bra, still covered by her blouse. I wanted to take a closer look, but she allowed the bottom of her shirt to fall and cover her pelvic region. "My flight comes in at 6:20 tomorrow evening," she said, continuing to talk to her husband, unaware that Karen was entertaining a naked man stretched out on her hotel bed.

Karen suddenly looked pensive, but then smiled. "What? You haven't been like that when I'm at home." She bit her lip as she moved seductively towards me. She stopped when she reached the foot of the bed and put her right hand on my thigh. "What do you think I'm wearing?" Wow. Eric wanted to have some phone sex with his wife. "Well, I'm just hanging out in my room in my underwear and my blouse...mmhmm...Really? You have it out? Are you touching it?" Karen was asking her husband all the right leading questions, while she was actually stroking my thighs with her fingertips. While she talked she straddled my thigh. I didn't move in an attempt to remain quiet with her husband on the phone.

Karen continued. "You are naughty tonight...," she said while slowly unbuttoning her blouse. "Yes, I am getting wet," she said to Eric while finishing off her unbuttoning. She was telling the truth. I could see a dark spot had developed on the silk of her panties right where her pussy was. She opened her shirt fully and let it fall behind her, leaving her in just her matching underwear. "I'm touching myself right now." She started to rub the already wet spot on her panties as she watched me stroking myself. "Mmm Eric, it feels so damned good...yes, I wish you were here..." She giggled a little and then said, "You like it in my mouth don't you?" She winked at me when she asked that.

She continued. "Oh Eric, I'm so wet for you..." My breathing was getting heavier and my cock was ready to explode. Karen put her finger to her mouth reminding me to be quiet. "You want me to put my fingers inside of me? Ooh, Eric..." The musky scent of her arousal was thick in the air, but got thicker when she said into the phone, "Wait a second while I take off my wet panties baby..." and then did just that. Karen's pussy had a thin line of hair protruding from the point where her swollen clit lie. She then got back on the phone and said, "Okay, now I'm fingering myself baby." She then crawled up on the bed and straddled my upper thighs. I could feel the heat from her pussy against my skin and stared at the wet exposed opening. Karen began rubbing her swollen clit. With every move, her body shuddered slightly.

"Oh Eric, I want your big cock inside of me..." With that, she grabbed my hard cock and positioned its swollen tip between her wet lips. "Ooh yeah, fuck me baby..." she commanded as she impaled herself on my cock. Her eyes got big and she inhaled deeply as I entered her fully. "Mmm, yes baby, you're fucking me..." she moaned to her husband on the phone. She began to ride my cock in a quick gallop, being careful not to slap down and make too much noise. I reached up and unhooked the front of her bra, releasing her perky breasts. She smiled and closed her eyes as I began to rub her nipples with my palm. "Yeah baby, I'm rubbing my clit and fingering myself for you..." she moaned. "Yeah, that feels so fucking good..." she said, but this time, more to me than to her oblivious husband.

I had to take a little control. I quickly flipped Karen onto her back and spread her legs wide by holding her ankles out. I began to pump her with all my might. It was apparent on her face that my move surprised her. She cupped the phone to keep the sound of my pelvis slapping her wet inner thighs from her husband. She said into the phone, "Ah yes, baby, you're fucking me so good and hard." I knew that she was talking to me. Karen's pitch started to rise and her breathing quickened. Her eyes widened as she exclaimed, "Oh baby, I'm going to cum for you. Oh yeah, don't stop. Cum inside of me! Fuck me harder!"