Will sat silently in his plush recreation room, waiting for his wife to return from the Country Club Halloween Party. His mind was still reeling from the fact that he and Jessie had actually gone through with their plan, at least as much of the plan as he had been involved in. The remainder would have been up to her and how daring she would be. His hard cock wavering between his legs was the telltale sign of how eager Will was for her to get home and tell him how the evening had played out.
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It had all begun about a week ago. Will is the golf pro at the club, and Jessie his trophy wife, tall and blonde with an athletic body that just screamed to be noticed. She did little to tone down the responses she got, often wearing tight tennis outfits around the club that accentuated her curvy form. After taking advantage of a lovely Indian summer afternoon on the tennis court, Jessie had stopped by the Pro shop to see Will. She was surprised to find a new face working behind the counter, a youngish looking boy.
"Hi, I was looking for Will, .....do I know you?" Jessie blurted out, tact never having been one of her strongest traits. As the boy began to reply, she noticed how his eyes kept darting down to her breasts. She had worn one of her thinner bras that allowed her erect nipples to poke through her cotton top, and she was getting a kick out of his clumsily obvious reaction to her appearance.
"Ah....no...I'm Andrew and I just started working today, my brother worked here all summer, but he started his new job this week, so Mr. Braxton asked me to help out after school, until the weather turns." Andrew replied while trying not to get caught peeking at this ladies boobs. "He should be back soon, do you want me to leave him a message, or could I help you in any way?"
"Well, you can't help unless you know if Mr. Braxton picked up our costumes today," seeing Andrew's confused look, Jessie continued, "I am Mrs. Braxton, and we were supposed to see if some crazy monster suits he picked out would work for the party.'
"Oh, yeah, I saw some big hairy thing laying across the couch in his office, that must be it." Andrew replied.
"Good, I will check it out." She said, pressing herself a little more than necessary against Andrew as she squeezed behind the counter on the way to her husband's office, noticing the way he averted his eyes and nervously attempted to avoid her touch.
Jessie had been a tease for years, and was thankful Will was not only tolerant of her behavior, but actually encouraged it. As she shut the office door, Jessie noticed the broken segment of mini blind that hung over the glass window in the door. She had been on Will for weeks to get it replaced, but right now, she realized his procrastination provided a perfect opportunity to indulge some of her exhibitionist desires.
As Jessie began to slip out of her gray tennis outfit, Andrew leaned closer to the door, peering intently between the broken blinds. He thought she was just about the sexiest woman he had ever seen. As her tennis outfit hit the floor, Andrew turned to examine the shop. All the carts had been returned and it was starting to get dark. He decided to take a chance and he quickly slipped his aching boner from his trousers to alleviate the discomfort brought on by the sight of Mrs. Braxton standing there in her bra and panties. Even though Andrew had done as instructed and told anyone asking for Mr. Braxton that he would be back soon, he knew Mr. Braxton was at the bar and had told him to lock up. Feeling fairly confident he would not be interrupted, he began to quietly stroke his hard cock as Mrs. Braxton bent at the waist to pick up her discarded skirt and top.
********
Will zipped down the drive in his golf cart. He had been half way through his fourth gin when he remembered Jessie and that damn costume. He saw her cart parked out front as he wheeled his in next to hers. Just before he opened the door, Will happened to notice his new employee obviously peering through the blinds on his office door.
"Well, that little shit," Will whispered to himself, halfway chuckling at his wife's ability to find ways to display her exquisitely displayable form to other men, or boys for that matter. Rather than barge in and interrupt Andrew's opportunistic view, Will quietly slipped around to another window that would afford him a better vantage point to the unfolding scenario.
*********
Andrew was watching intently as Mrs. Braxton carefully folded her tennis outfit and placed it on her husband's desk. Then, instead of trying on the costume, she went to the mirror and began to examine her reflection, turning and posing as she seemed to assess each and every lovely curve on her body. Andrew's cock was rock hard, and he continued to steadily stroke it as he took in what he thought to be an unintended display by his boss's wife.
***********
The last thing Jessie wanted to do was cover her body with that big bulky excuse for a Halloween costume while she was presented with such a perfect opportunity to do what she loved most, 'accidentally' tempt an unsuspecting male. The fact that her audience happened to be a teenager excited her even more. She had been prancing and posing before the mirror for several minutes, and was about to unhook her bra and really give him something to remember when the phone began to ring.
**********
Will couldn't believe his eyes. From his new vantage point, he was able to clearly see Andrew as he peered through the window of his office door. The boy had actually pulled out his cock and was rapidly stroking it. What caused Will to do a double take was not the mere fact that the boy was jacking off to the sight of Jessie, hell, most any man in the same situation would be tempted to do the same, rather it was the size of the prick jutting out from Andrew's pistoning fist. Will had always prided himself on having a nice sized cock, but he would come in a distant second in both length and girth to this kid. He watched for a few seconds longer, imagining the look on Jessie's face when he told her a kid with such an impressive cock and been stroking it while spying on her. He was certain Andrew was going to blow all over the door. Just then he noticed Andrew jump at the sound of the phone ringing on the counter next to him.
Will then heard some of the other guys leaving the clubhouse bar, and decided he should take the opportunity to breakup Andrew's private peep show before someone else came by and saw what was happening.
Andrew was still speaking to one of the members when Will entered the shop. He noticed Andrew had evidently stuffed his prick back in his pants, but was still taking extra care to hide his crotch behind the counter as much as possible.
"It's Mrs. Rothstein," Andrew whispered, while covering the mouthpiece with his hand.
"I'll take care of her and I'll lock up too, you did a fine job today, now go on home and I'll see you tomorrow." Will said, barely able to stifle his laughter as the boy almost fell over himself trying to get to the front door without displaying what was certain to be a still substantial bulge in his trousers.
As Will finished confirming the tee time for Mrs. Rothstein's husband, Jessie stepped from his office, completely dressed again in her gray tennis outfit. He hung up the phone as she said, "Hi honey, what happened to your new worker, Andrew?"
