“Men prefer long hair,” she complained to her husband one night, not long after she made the dramatic transformation. But despite his constant reassurances, she still felt the need to turn up the heat. Feeling sexy was important to her, especially as she aged and became more acquainted with her own sexual desires.
It was from these conversations that the little bet came about.
“I think you are missing what the guys are really looking at,” he said one night. “I bet more guys are looking at your hot body and killer legs than your hair. You’re just too focused on your new hairstyle to see that they are lusting after you like they always have.”
“Are you trying to tell me that I’m just not noticing being noticed? I’m pretty sure you’re delusional about your thoughts on what other men think about your wife,” she retorted. “No one, except for you, is lusting after me.”
“Let’s say we put something on this … a wager, so to speak,” he said to her. “A simple bet that will prove once and for all that you are still the same gorgeous and delightful distraction you have always been – short hair or long.”
And so the deal had been set: for one week she would carefully take note of any untoward flirting, blatant ogling and outright compliments. The magic number was set at a grand total of 12 different men in her life. If Andee won the bet – meaning less than 12 guys made any kind of flirtatious remark or obvious glance her way throughout the week – her husband would have to plan one the most romantic weekends away, no children allowed … but if she lost the bet and more than 12 different men said anything about her looks, she would have to leave her panties in a certain coworker’s office that she had been lusting after for some time. How she managed to get that far would be entirely up to her. In her own mind, she figured either way she would be winning in some sort of fashion.
Come Monday of the start of the bet week, Andee complained to her husband that the whole thing was silly. Over breakfast, she explained how she could easy manipulate the outcome, or outright lie about what happened each day with the men she encountered throughout the day.
“But what fun would that be?” he asked. “If you cheat, then what’s the real point? Don’t you want to see the results – bet or not? Besides, I think you’re too competitive to take the easy way out this.”
Andee had to concede that her husband had a point: it wasn’t so much about the consequences as it was about finding her sense of “sexy” once again … and she had the opportunity to exploit it, with permission. And she was extremely competitive.
She made it through the week, and had managed to clock in an honest 10 points in the bet without having to resort to any exceptionally naughty tactics. During afternoon break on the Friday, she was feeling a little let down despite knowing that if she won the bet she was still getting an amazing adults-only weekend with her husband. Her friend Paul noticed that she wasn’t being her usual self and asked what was going on.
Without letting on too much about the conditions to her bet, she told him a bit about what had been going on all week and why.
“I guess my compliment may only get you one closer to winning, but you do look amazing – you have all week and I know that a lot of the guys here do think you are incredibly sexy,” he said. Paul gently stroked the back of her hand with his, sending an electric buzz straight through her body. She had long relished his touch and often flirted madly with him, but this time he initiated the sincere gesture. She watched his nice ass as he walked away, and was suddenly struck by the irony of the moment – here she was ogling him from behind and he wasn’t even aware.
She got up from the table and ditched her coffee cup into garbage can before heading back to her department to finish her shift. As she walked towards the elevator, she passed by a couple of the guys from finance.
“You look very lovely today, Andee. What’s the occasion?” one of them asked. Andee smiled and politely replied, wondering to herself that she might have just been set up by her coworker, to whom she had just confided. That compliment was 12 for the week, the magic number.
Andee stepped into the elevator and waited for the door to close. One of the hospital porters jumped in at the last minute and smiled politely, pressing the button for one of floors and sidled up the back of the lift, just slightly behind Andee. As the elevator slowed down as it reached her stop, she felt him lean very close to her ear.
“Forgive me for being so forward,” he whispered. “But you look so fucking delicious for a Friday …”
Andee blushed and smiled as she stepped from the elevator, knowing she had been had. She knew the man and he had never spoken to her like that before.
Later that night at home, her husband seemingly avoided saying anything about the day or the bet in general. As they were getting ready for bed, Andee asked him if he was even curious about how things had gone. He explained that it wasn’t so much about winning or losing, long hair or short, but that she came to realize that she was still the desirable woman she had always been.
“And 13 men agree,” she said bluntly, signaling defeat. That night, Andee and her husband fucked like they hadn’t in years; and again in the morning.
On Sunday night, her husband broke the feigned silence around the consequences of the bet and asked if she had given any thought to how she was going to make good on her debt. Then, without hearing much of what she had to say in defence, opened the closet door and handed her a hanger of clothes. It was a new dress, some thigh highs and a pair of black lace panties with matching bra.
Monday morning couldn’t come fast enough …
As Andee rode in on the commuter train the next day, she could feel the excitement building within her. She intentionally let the hem of her dress slip open when she crossed her legs and carefully watched as some of the men sharing the train car were mesmerized by her legs. Andee couldn’t tell if any of the lace tops of her thigh highs were showing, but she was secretly hoping that a small hint was revealed to those who were looking. She was beginning to really feel sexy … and brave.
Walking the short few blocks to the hospital, anyone who knew her might have noticed the extra little spring in her step, and that her mood was definitely more upbeat than it had been in weeks. Andee looked like a woman on a mission – and she most definitely was. She just hadn’t figured out how it would all play out. In her mind, for quite a long time, she had created a little office seduction fantasy with her coworker – and even confessed the details to her husband during some of their steamier bedroom moments.
After being distracted by the idea all morning, before lunch she slipped out a few minutes early from her department and caught her friend Paul in the hallway. His eyes almost popped out of his head when he saw her. He gave Andee a thorough once-over with his eyes before telling her how incredible she looked.
“You look stunning. New dress?” he asked.
“Among a few other things,” she purred back. “Meet me in your office for afternoon break if you would like to see the rest of it.”
Paul gulped and Andee quickly gave his cheek a quick kiss before swaggering down the hall. She knew her coworker’s eyes would be fixed directly on the sway of her hips.
It felt like it was taking an eternity for the hours to tick away before the afternoon break arrived. Andee felt a sense of pure fear and sexual desire at the same time, wondering if she could actually go through with her fulfilling her “payment” on the debt. On her way to her coworker’s office, she quickly stopped into the ladies room to make last minute adjustments. Her pussy was beginning to heat up with the anticipation and she felt a wave of nervous excitement come over her as she lightly touched herself while adjusting the tops of her thigh highs.
When she reached Paul’s office, she quickly glanced up and down the hallway to see if anyone was watching and then slipped in. Her friend was sitting at his desk and turned to face her as she quietly closed the door and locked it.
Andee stood with her back against the locked door as he rose from his chair. She flashed a flirty little smile as he began to obviously undress her with his eyes. Paul took her hand and pulled her gently into the middle of his office and then quietly walked around her, as if he was inspecting her.
“You are so fucking sexy,” he said in a soft sensual voice. “So fucking sexy.”
Andee closed her eyes as Paul’s lips pressed against the back of her neck. It was as if he knew the exact spot to touch that would set her on fire. He reached around and cupped her breasts, fondling them lightly. She could feel his erection pressing against her buttocks as he slowly moved his hands down from her breasts to her hips. Through the thin wisp of her dress he traced the outline of her panties, almost as if he was trying to discover what type of panties she was wearing. First his fingers traced along the waist, all the while he was still kissing the back of her neck, behind her ears and all the spots that sent quivers through her.
His light touch was an incredible tease, and Andee pushed back against Paul’s hardness. She titled her head in a subtle submissive way, allowing him to nibble even more of her flesh. His fingers followed the seam along her pelvis and down between his thighs, causing Andee to jump a little.
“Too much?” Paul whispered in her ear.
“No,” she managed to reply. Andee pressed her hips forward against his touch. She reached down and grabbed the sides of her dress and started to pull the fabric up. Paul’s hand moved further down the inside of her now exposed thigh, tracing the lace top of her black thigh highs.
Andee shuffled so her legs were parted just slightly, allowing her coworker to slide his hand down across the front of her panties and to the moist spot that gave away how turned on she was. Paul gently massaged her pussy through the fabric, causing her to let out a barely audible moan. Andee was enjoying this moment.
Paul’s finger slid under the seam of her panties and across her now swollen clit. As it did, Andee moaned a little louder with the sensation of having the new man touch her there. His touch sent a sexual jolt through her whole body.
He lightly brushed across the moist opening to her cunt, not quite penetrating but teasing her enough that he could feel her hips arch slightly, as if she was trying to push herself onto his finger. He stroked along her wet pussy lips for a moment and back across her clit. Andee was now on fire and anxious to feel her friend slide his long finger deep into her.
Andee lifted one leg and placed her foot on the office chair, allowing Paul unrestricted access to her dripping pussy. He pulled his hand out from the side of her panties and then slid it down under the waistband, all the way back to her wetness. He toyed with her clit for a moment, and then pushed his middle finger right into her cunt. Andee let out a gasp of delight and titled her head back. She was in heaven.
Paul continued to finger her as she slid her own hand down under her panties. She stroked her clit as he kept up with the internal massage, sending her mind and body in a million different directions. As Andee’s thoughts eased back to reality, the notion of having her coworker fingering her was just enough to put her over the edge. Paul could feel the orgasm building inside her as her cunt muscles squeezed hard on his finger and Andee began to rock her hips faster and faster.
Finally, she shuddered and twitched as waves of sexual release came over her. Paul could feel the flood of her orgasm, the wetness of her pussy becoming even hotter.
Andee stayed in this position for just a few more minutes, holding onto his wrist so his finger remained buried in her cunt. He could feel her flexing as she basked in the last few sensations of her orgasm. Then, she gently removed his hand from under her panties and turned to face him.
She dropped the hem of her dress and began to unbutton the front. It was obvious that this was the kind of moment her husband had envisioned when he planned a button-up style. Once she had it completely undone, Paul could run his hands on her hot skin. She undid her front-clasp bra, exposing her hard nipples to his touch. He fondled them until her nipples were hard, and then leaned in and sucked on each one. The sensation of Paul’s lips and tongue sent orgasmic jolts straight down to her still twitching pussy. It was an incredible sensation.
Paul stood back and watched as Andee hooked her thumbs into the waistband of her panties and slid them down past her knees and let them drop to her ankles. He could see how wet she had been from what had just happened, the glistening moisture from her pussy soaked into the crotch. She stepped out of them, leaving them on his office floor for the moment.
She took her friend by the hand and directed him to sit in his office chair. “Your turn,” she whispered into his ear and she leaned in to kiss him.
Andee knelt before him and slid his pants down to his ankles. His erect cock jumped as she did, pointing directly at her. Paul was built nicely for his age, slightly larger than her husband and extremely hard. She wrapped her left hand around it, knowing that when Paul looked down he would see her wedding ring as a reminder that he was enjoying the pleasure of someone else’s wife.
She stroked him for a few moments, getting the sense of the new cock 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. His pre-cum had a slightly salty taste. As she did, he flexed his erection hard and let out a deep breath.
Andee took his erection back into her mouth and worked her tongue with even more ferocity. Every now and then she would change the pace, or let Paul’s rock hard dick slip out of her mouth and would just flick the little spot under the head with her tongue. The tease would drive him wild, and he would clutch at her head with his hand to try to direct her back to sucking on him.
She could tell when he was close to coming, so it wouldn’t take much to get him to explode into her throat by the time she got him that worked up. Paul grabbed her hair and began to force his cock in and out of her mouth aggressively.
Andee put her hands on his thighs to brace herself against his face-fucking. It was a huge turn on for her when guys did that. It made her feel that she had taken them to the point in the blow job where they could no longer control their animalistic desire to have her swallow their cum. It was in that moment when she knew she had control over the situation.
She felt Paul’s cock swell even more. He was now steel-hard and Andee’s experience told her he was about to lose everything. The thought had hardly crossed her mind when she felt Paul’s cock twitch in the way she loved and his hot cum shot into the back of her mouth. She moaned loudly as he pulled her hair hard, grinding her nose into the flesh above his cock, forcing all of himself deep into her mouth.
He held Andee there until he had finished shooting his cum into her mouth. She gently slithered her tongue around the slowly shrinking cock, tasting every last bit of him before finally letting him pull out. She remained between his thighs, gently stroking him until he was totally drained and flaccid.
Paul leaned back in his chair, completely spent from the incredible blowjob he had just received from his sexy coworker. He opened his eyes and watched Andee put herself back together, buttoning her dress back up slowly as if to tease him even more. He watched silently as she picked up her panties from where they had been left.
“I don’t want to see these hanging from the mirror in your truck,” she said jokingly as she squeezed her panties into the palm of his hand. “But you might want to think of a way for how I can win them back.”