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.