It had been a long time in coming. Andee wasn’t sure if having to “pay up” for losing a friendly bet with her co-worker was just a passing joke in the hallway, or if he was serious about collecting on it. As a thirty-eight year old mom of two very active boys and career woman, she enjoyed a bit of adventure in her life and this was the second time in a year she had found herself confronted with a sexual complication with her friend.
Without question, Andee had been a shameless flirt with Paul, one of the purchasing agents at the hospital where she worked for quite a while. She fondly remembered the time when she had to leave a pair of her panties with him after losing a silly bet with her husband. In fact, the experience often floated through her mind as she masturbated.
As she edged towards her forties, she was discovering how much more confidence she had in herself – and how much she enjoyed playing the role of office flirt and her friend certainly didn't seem to mind the attention. A petite woman, she conveyed an aura of sexiness that served as a distraction for the men around her. Of course, it didn’t hurt that she was still in great shape, and loved to show off her figure with a stylish passion for short dresses, miniskirts and low-cut blouses.
If nothing else, Andee figured making this new bet would make for some fun banter at work. As a dedicated hockey mom and former competitive athlete, she was a real sports fan - and more interested in talking hockey with the office guys than nail salon gossip with the girls. And she took her fandom pretty seriously.
One Monday morning, while she and her co-worker were ribbing each other about how their teams had done on the weekend against each other, Andee scoffed that her friend was cheering on the wrong team. Paul reminded her that it been a number of seasons since her team had even made the first round of playoffs, never mind the decades since their last championship.
"Oh yeah? Well I bet they do better this year than your team," she threw back at him.
Paul laughed at the notion, and then said "You're on."
"We'll settle the terms next week ... that should give you some time to carefully consider just what you have gotten yourself into."
The week passed without any indication from her friend what he thought the payment should be. Andee, despite her initial bravado in making the bet, knew she didn't really stand a chance of winning. When she asked her co-worker if he had made up his mind, he suggested they wait until closer to the end of the season, and then the real stakes would be a bit more obvious - plus it would leave some intrigue to the deal.
All season the pair bantered back and forth, as Andee's team flirted with a promising run at making the playoffs this year; but in the final week of the regular season slid just shy again. She waited until the following Monday, wondering what Paul had in mind for some payback.
"I have some ideas, but let's be honest, we both know that anything more than you buying me a coffee is out of the question," Paul said that afternoon.
"Well, that's not really fair. You won the bet, and I should be the one to decide if your 'payment' crosses the line. So, come on, spit it out."
"Something that requires you to be wearing stockings and garters."
"At work? That's easy enough ... and hardly anything really you can count as consequences for losing a bet. How do you I don't wear them now? Or did you mean something silly - like those things you guys wear under your hockey gear?"
"True enough," Paul replied with a thoughtful expression on his face. "Photos ... I want to take a photo of you wearing nothing but a garter belt and stockings. The sexy lingerie kind, not 'hockey socks.' You once told me that you let your husband take naughty pictures ... This could be something that I can look back on when my team wins. Call it a victory parade as you pose for me."
Andee was slightly shocked by the suggestion. She had long forgotten the time when she had told Paul about how her husband and she played around with his new digital camera.
"That is unless you can't deliver on your debt," he said with a teasing - but still serious - tone.
"Um ... No, I'm not about to welch on my bet. But I'll need a bit of time to make the necessary arrangements for payment," Andee replied. Her stomach had butterflies, despite how excited the idea made her.
All the way home on the train that day she ran over how she would explain the situation to her husband. Not telling him wasn't her style, especially when she knew there would be some photographic proof out there. At home, she set to work on setting up the perfect moment so she could discuss it with her partner. She ordered some pizza and put a movie in for the kids, so they would be properly distracted from the private conversation.
"What's the occasion?" her husband asked.
"We need to talk about something that happened with me at work," she began, proceeding to explain the whole situation.
A glass of wine later, her initial fears over what her husband would say when she confessed to the arrangement vanished when he laughed and replied, "You and your competitive nature. I told you someday you would end up in trouble because of it. Well, I guess this is OK with me, but with one condition: only if I get to watch."
The following day she caught her friend in the hallway. "I explained things to my husband."
"Let me guess, he put the kibosh on the whole thing."
"No ... he's all for it," Andee explained. "But only if he gets to be there ... to watch."
By the next day Andee had put together the whole scheme. She would wear what she would be modelling in for Paul on Friday. Throughout the day, she would ensure he was properly teased so that by the time the photo session rolled around after work his imagination would be spinning. She had booked a room at a hotel not far from the hospital and ordered in some food.
Andee arrived before either of the guys and checked in. She quickly texted each of them the room number and set to work on getting ready. She slipped out of the panties she had been wearing all day - a strategic move because of how wet and turned on the day of flirting had made her. She also touched up makeup and hair before slipping into a skimpy, not-suitable-for-work dress.
And then she waited to see who would show up first...
Andee's heart jumped when she heard the knock on the door to the hotel room. She took a peek through the security hole before opening it. Paul stood in the hallway momentarily as he scanned her from head to toe.
"Fuck me," he muttered. "You look ... amazing."
Andee had hoped for this reaction. She had been very careful to select a sexy black wrap-around dress. The hem hung just below the lace top of her sheer black stockings so not to give it away on first look. The front revealed a bit more cleavage than she was used to showing with her nice 36B breasts, but the intent was really for the dress to be coming off soon. She added a pair of sky-high stilettos to the outfit, the kind she would get way more use from by having them pointed at the ceiling instead of treading on the carpet.
"Not too much? I debated if I should wear the stockings that have the seam running all the way up ..." she said flirtatiously, giving a little pirouette.
"Fucking perfect," her co-worker growled back.
Andee grabbed his hand and pulled him into the room. She kissed him deeply as she quickly stripped his jacket off of him. Her body came alive as Paul's hands ran over her back and down across her ass as they continued to kiss.
Finally breaking their embrace, Andee led her friend into the hotel room and forced him onto one of the beds.
"The guy bringing the camera isn't here yet," she said in a sexy whisper as she straddled his lap. Andee could feel Paul's growing manhood against her crotch as she ground against him.
Andee slid a hand down to his belt and unbuckled his pants as she continued to kiss him. She worked his zipper open and wiggled her hand into his underwear and wrapped her fingers around his swollen cock. It was very hot to the touch and she could easily tell Paul had a very nice size between his legs.
“I remember this,” she said playfully and squeezed his erection. “And I want it …”
She felt her friend slide his own hand along her thigh and under the hem of her dress. He gently stroked her inner thigh, just above the lace top of her stockings, using his thumb every now and then to brush across the thin wisp of panty that was getting wetter and wetter. He could feel her pussy reacting to his touch.
Andee was just about to change the circumstance between them when she heard a knock at the door.
"Crap," she muttered in sexual frustration. She looked at her friend with a mix of excitement and disappointment at having to stop their passionate make-out session, then shuffled off the edge of the bed and straightened her dress before she went to let her husband in.
"Looks like you started without me," Andee's hubby said with a wink and nuzzle as his hand slipped under the hem of her dress and across the moist crotch of her panties. He gave her a quick peck on the cheek and walked into the room.
The two men made quick small talk as if they were old buddies and the situation was an everyday encounter between them. Paul got a quick lesson on how to work the camera and then it was back to the business at hand.
"Most importantly, don't let me stop you. Pretend I'm not even here ... I'll just sit over here in the corner ... quietly," Andee's husband said as he settled into a leather chair in the corner of the room.
Andee started with a few casual poses, just to allow her friend the chance to get used to the idea and settle into things. She could tell by the way he fumbled with the camera that he was still a bit nervous, likely because just a few feet away, her husband was sat watching intently.
As she got into the mood a bit more, and her mind wandered back to the sensation of having Paul’s rock hard cock in her hand just a few minutes earlier, she started to turn on the sexual heat. Each new pose, she would flash Paul a bit more of what she wore under her dress, noticing that his pants grew tighter and tighter.
After a few more poses, she strutted over to her new photographer and placed her arms around his neck.
“So now that you’ve taken about 20 pictures of me in some pretty tame poses, let’s say we really get down to something a little more … no … a lot more sexy?” she whispered in a very low tone in his ear. As she backed away, she lightly swept her hand across his crotch.
She took up a spot in the middle of the room facing the two men, and began to untie the belt around her waist. Paul kept clicking away as she seductively let the dress slip off her shoulders and eventually onto the floor at her feet. She was now down to just the lingerie she had carefully selected for the moment.
Andee continued with the torment by sliding a hand under the waist band of her own panties and massaging herself with her fingers. She could tell Paul’s cock had reached its rock hard limits in his pants. She pulled her wet finger out from between her legs and slid it into her mouth. She smiled seductively as Paul’s eyes were fixed on her finger sliding across her tongue.
With a wicked wink at her husband, Andee then said, “You know, when my photographer at home shoots these kinds of photos, he makes me feel comfortable about getting naked by removing some of his own clothes.”
Paul couldn’t muster much more than a boyish giggle and an “um” in response. Andee upped the ante a bit more by reaching behind her and unhooking her bra, letting it fall slowly off her lovely 36B breasts.
"He's not here, remember," Andee said with a devilish smile on her face. She sat on the edge of the hotel bed and began to stroke herself under her panties.
“Time for some money shots,” she purred, pulling her panties to the side and revealing her soaking wet pussy.
"God, that looks delicious," Paul managed to gulp.
"Then come and have a taste." Andee shuffled back on the bed and propped up her legs, spreading them in an invitation for her co-worker to get physical. Paul set the camera down and knelt between her legs.
Andee shuddered with erotic anticipation as Paul gently pulled her panties to one side. She could feel his breath on her pussy as he slowly began to run his finger up and down her lips, massaging her clit each time he passed over it. Her body was responding quickly to his touch, and she could sense how wet she was getting. After a few long minutes of this teasing, Paul finally slid his middle finger deep into her.
A small moan escaped from her, as she lightly pressed down against his penetration. Her cunt felt like it was pouring now, she was so wet. She wanted him to make her cum again, just like he had a couple months ago in his office. She wanted to feel him stroke the sensitive spot just to the right of her clit that would bring about an orgasm in a matter of minutes … only this time with his tongue. She wanted him to lick her until she couldn’t cum any more.
Thankfully, she didn’t have to wait long. She felt Paul edge closer, his breath sending a tingling straight through her clit. Then, just as she was about to open her mouth and beg, she felt his tongue flick across her swollen pussy.
Andee let out an “ahhh” as he did and arched her back to push her cunt against his tongue. She had listened to him brag about his oral talents for some time, claiming to have learned a special technique that would guarantee an orgasm for just about any woman that would let him between her thighs.
It only took Andee a minute to realize that he wasn’t stretching the truth. His tongue seemingly worked magic along her pussy and clit, drawing her closer and closer to cumming. After a few minutes of his oral torment, the combination of his tongue and fingers sliding across her g-spot were too much for Andee to hold back against any longer. She could feel the wave of orgasm starting to build deep inside her hot cunt. Then, with a few more licks across her swollen clit, she was gone - past the point of being able to control it any longer.
Andee grabbed Paul's hair with both hands and bore down against his face. Her back arched as she launched into cumming. She groaned loudly in between the "Don't stop" instructions she was giving him ... as if he might. Her face flushed and she gritted her teeth, letting out a deep sexual growl as her cunt exploded with her orgasm. Her swollen clit was now on fire as every minute nerve ending came alive. Her vagina clenched involuntarily at his fingers and then throbbed as it joined the release.
"Oh my god," she muttered repeatedly as she started to come down from her sexual high, Paul remaining between her thighs and lightly stroking her soaking wet pussy.
Andee lay still for a few minutes, her mind drifting through the incredible sensations she had just enjoyed and slowly back to reality as she heard a couple clicks of the camera. Paul had picked it up from where he had left it and was snapping photos of Andee sprawled across the bed, sweaty from her orgasm. She smiled and shifted to give him a few different angles.
"Your turn," Andee said as she pulled Paul's pants and underwear off.
As he lay back on the bed, his erection bounced up and down. Andee licked her lips in anticipation before wrapping her fingers around it. She bent over and licked the glistening pre-cum off the head. He had a slightly salty taste. Paul closed his eyes and let out a deep breath.
Paul was built nicely for his age, slightly larger than her husband and was now steel hard. She wrapped her left hand around his swollen dick, knowing that when Paul looked down he would see her wedding ring as a reminder that he was once again enjoying the pleasure of someone else’s wife.
She stroked him for a few moments, getting the sense of this hard cock that in her hand. Andee looked up into Paul’s eyes, trying to convey her desire without saying anything. Her husband would often tell her that the greatest part of her blowjobs was the look in her eyes and the excitement in her expression. Andee slid her tongue out of her mouth and licked the tip of Paul’s cock.
Andee took his erection back into her mouth and worked her tongue up and down his shaft, spiraling left and right to heighten his sensation. She knew he was close to cumming, so it wouldn’t take much more to get him to explode into her throat.
Andee moaned as Paul grabbed her hair in his fingers. She felt his hips begin to match her own motion on his cock. He was close.
Andee looked up into Paul’s eyes just as he unleashed a flow of hot cum onto her tongue. He groaned as he pumped himself in and out of her mouth as his cock slowly became soft. She kept her lips wrapped around him, enjoying the taste of his cum.
She lay on top of her friend for a few minutes, both of them exhausted from the experience and drained. After a few minutes, Paul got up and put his pants back on.
“I don’t want to be the one to remind you of this, but I’m starting to think you make bad bets on purpose,” Paul chuckled as he sat on the edge of the hotel bed.
Andee, still on her back in the middle of the bed, rolled towards her grinning husband, and with a familiar sexy purr said, “Your turn …”
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