Tricked Then Treated

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Teen boy can't resist the temptation of his boss's wife
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JackKing
JackKing
1,694 Followers

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.

************

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?"

"I just sent him home," He replied, "Unless he has to stop and jack off before he gets there, what were you doing in there to cause him to have to start playing with himself right here in plain view, and on his first day on the job?" Will laughed as he pulled his sexy wife close to nibble on her neck and ear.

"Why, I don't even know what you mean, I was just trying on that lil' ol monster costume." Jessie drawled out her best innocent southern belle accent, batting her long eyelashes at her husband before breaking out in laughter.

"Was he really playing with himself?" she asked, barely able to contain her excitement. "I had hoped he would look, but I never expected him to actually start jerking off like that."

"You don't even know the half of it," Will said as he pushed his wife's hand down to his now hard cock as it pressed outward against the fabric of his pants.

"Mmmmm, perhaps I can convince you to tell me." Jessie cooed as she slowly dropped to her knees and began to unzip Will's pants.

Will knew he should lock up, or at least move Jessie back into his office, but he also knew Jessie liked taking chances with public sex like this, plus she already had her lips wrapped tightly around his swollen cockhead, kissing and licking like she was desperate to taste his jizz as soon as possible.

Jessie stopped sucking long enough to say, "So, are you going to tell me the half I don't know, or do I need to stuff this back in your pants and go on home." She looked up at him as she waved his erect dick around with her well-manicured hand.

"Well....you remember last week when we rented that XXX movie, and I joked to you that you couldn't compare normal men to all the guys in the movie because they used special lighting and trick camera angles?" Will asked.

Jessie stopped sucking Will's cock and simply stroked it with her hand, occasionally rubbing his pulsing and saliva coated head against her cheek, as she looked up into his face, saying "Uh huh, I remember."

"Let's just say that if working at the pro shop doesn't pan out for your new admirer, he should have no problem making it BIG as an adult film star." Will said, feeling his wife squeeze his shaft even more firmly as he revealed his discovery to her.

Jessie began to stroke his cock faster, licking, kissing and sucking the head past her soft lips, even as she managed to say, "That makes me so hot, you know how exciting it is to know a teenage boy was playing with his huge cock only a few feet from me, probably thinking about how he'd like to pump his long, fat dick in and out of my tight pussy."

Hearing his beautiful wife talk so dirty was pushing Will to the edge, and within seconds he was spewing his hot cum past her lips and down her throat. They went home that night and had the best sex in years, the entire time talking about how Jessie had teased Andrew and how he must being home dreaming of fucking her.

**********

That had been a week ago. And every day since, Will and Jessie had had sex. Even when they didn't talk about Jessie and Andrew's big cock, Will was certain she was trying to imagine it as she squeezed her eyes shut while Will pounded into her over and over again.

But it was actually during a time when they were arguing, not making love, that the idea first came to Will.

"I still don't know why you thought getting two goofy looking monster suits was a good idea for our costumes this year. I liked the Genie and Harem Girl getup from last year just fine." Jessie said, put out with Will for this uncharacteristic desire for restrain her from taking advantage of the best exhibitionist holiday there was. Halloween was the perfect excuse to wear a sexy outfit and get away with it.

"Look Jessie, I love to show you off as much as you do, but I have to think about my job at the club. Letting your nipples poke through your tennis outfit is one thing, but I've heard form Jerry and Stan that Mrs. Rothstein and some of the other old withered up bags on the board made quite a fuss about your attire at last years party. You have to admit it was pretty daring, especially as you kept removing veils as the night went along." Will said, trying to remain calm.

"Okay, I guess I can see your point, but why those damn fur balls, I mean surely there is some room for compromise here. Really Will, those things are so big and bulky you could almost fit two people in there."

"Come on Jess, just don't make such...." And then it came to him. Will didn't know exactly how they would pull it off, but he knew they could do it some way, "Jessie, maybe we can reach a compromise after all."

*********

Will looked up to see Andrew coming in the shop, as planned. "Sorry to ask you in on Halloween Andrew, but we need to finish up the monthly inventory count today. Hopefully we'll finish up in time so this won't intrude on any big plans you have tonight."

"Oh, no sir, I don't have any plans anyway. But isn't tonight the club costume party?" Andrew asked.

"Yeah it is, I just hope I feel up to going, I have been staring at this damn computer screen and all these numbers for so long, I feel a real bitch of a headache coming on." Will lied, laying the groundwork for his unfolding plan.

Andrew was still diligently counting the boxes and boxes of gloves, balls and tees in the storage room when he heard the bell on the front door ring, indicating someone had just entered the shop. Soon he could hear Mr. and Mrs. Braxton talking through the thin walls of the office. "You don't look so good honey." He heard Mrs. Braxton say.

**********

Will was admiring his wife's shapely form, even as she stood before him in a set of baggy sweat pants and sweat shirt. "It's just this damn audit. It has my head pounding." He smiled as he spoke, grabbing his semi-hard cock with one hand and inserting his free hand past the waistband of Jessie's sweats until he could feel her lacy silk panties and the heat being generated by her expectant pussy.

"Maybe we should just skip the party." She said, squirming beneath her husband's fingers.

"No, I know you've been looking forward to this all year, let me just take some more aspirin and try and outlast this pounding between my ears." Will continued to speak loudly enough to be certain Andrew would hear them.

"Well, not to hurt your feelings or anything, but .....well, I don't think you will be much fun if your head is hurting so bad, and given our costume, I don't think I'd have much fun cooped up with you, and I can't make it work without you, so let's just call it off."

"You may be right honey, I just hate for you to miss.....hey, hold on a second, I have an idea, just wait right here." Will gave Jessie's pussy one last stroke as he kissed her deeply, whispered to her that he loved her, then stepped from his office.

"Andrew, can you come here please." Will worked hard to look as if he felt like shit as Andrew came around the corner. "Andrew, I have a favor to ask of you. My headache is worse than ever, but I don't want Jessie to miss the party. The problem is that we have one of those two part costumes that requires two people to make it work properly. Would you mind filling in for me tonight at the party?" Will asked.

"Ah, well, ....yeah, I guess, if you really need me to I will." Andrew replied, uncertain as to exactly what he was agreeing to do, but hesitant to deny his boss's request.

"Great, Jessie just got here. We were going to get dressed here then go on over to the clubhouse. Come on in and I can help you two get in the costume." Will said, watching Andrew's eyes dart quickly over his wife's modestly attired yet well-defined figure.

"Good news Jessie, Andrew here is going to fill in for me so you can still go and have a good time." Will started to introduce them, but Jessie interrupted him to say they had met a week or so ago. She thought she noticed Andrew's face flush slightly at her reference to their earlier meeting.

Jessie took charge, "That's very nice of you Andrew. Don't worry, about anything, no one will ever recognize who is in this costume, so you won't have to even speak to anyone if you don't want too, just grunt like a monster is all you need to do." She laughed to try and ease his obvious discomfort, but he still seemed wound rather tight.

"We need to get dressed if we plan to be on time." She handed Andrew some sweats, saying, "I brought these for Will, er I mean Mr. Braxton. Go change into these then come back and we'll get into the suit."

Andrew walked past the bunched up brown fur, which he assumed to be their outfit as he went back into the storage room to change. He came back a few minutes later to find Mr. Braxton laying the costume out along the couch.

"Okay Andrew, I need you over here first." Said Mr. Braxton. He had Andrew step into the feet of the monster suit.

Will was quite pleased with the job his tailor had done on the costume. He had kept his plan from Jessie until the suit had been fully altered. She had thought he was joking at first, but the more they talked about it, the more she realized he had been completely serious. And then as the date approached, they had begun to scheme and plot how they would carry out the seduction of their well-hung and unsuspecting victim.

"Now, Jessie, you come over and stand right in front of Andrew. Good, you two are about the same height." Will and Jessie both behaved in a completely innocent manner, even as Jessie pressed her bubbly firm ass into Andrew's crotch.

Will positioned their feet inside the extra wide monster feet, directing Jessie to place each foot against the inside of each of Andrew's feet. When she was in the proper position, Will produced a Velcro strip and wrapped it around their ankles, firmly securing them together. He explained to Andrew this would enable them to walk in a cohesive manner, even as he wrapped another Velcro strip around their calves and then their thighs.

Andrew could smell Mrs. Braxton's intoxicating perfume on her bare neck, only inches from his nose. Her blonde hair was pulled back in a ponytail, leaving her ear free to randomly brush against his smooth cheek. And then there was her ass. It was pressed firmly against his dick. The way Mr. Braxton had fastened them together, he could not retreat from the pressure of her lovely cheeks. He pictured how she had looked in her bra and panties that day in the office, and he felt his cock begin to grow. He was petrified of how she might react.

Will helped Jessie zip up the front of the suit and slip each head up and over first Andrew, then his wife. Andrew extended his arm through the right sleeve of the costume and Jessie did the same to the left. Will stepped back, managing to conceal he already growing erections, and admired their outfit. The modifications Mr. Neilson had done were perfect. The positioning of the shoulder pads and the angle at which the heads had been attached, coupled with the bulk of the furry material, made it difficult to know whether there was one or two people inside the costume.

"Why don't you two let me help you walk to the door. It will probably take you a little while to get the hang of coordinating your movements." Will cleared a path for them as the two-headed monster lumbered through the pro shop.

Mrs. Braxton's ass pressed relentlessly against Andrew's crotch. His cock, already half hard, was poking firmly into her right bun. Andrew couldn't believe Mr. Braxton had literally strapped him to his incredibly sexy wife. He was trying to think of anything and everything but the sexy older lady and the way her body swayed rhythmically against him with every step they took. Despite his sincere intentions to dissuade his body from reacting, Andrew was very doubtful they would be able to clumsily walk to the clubhouse without him attaining a complete erection.

**********

That had been the last Will had seen of his wife and Andrew before he left for home more than 4 hours ago. He had given up trying to think of anything but what might have happened, or still be happening with Jessie and Andrew.

Finally, Will heard the key in the front door and then Jessie's soft footsteps coming down the stairs to join him. She entered the room, still wearing the same sweats he had last seen her in. She looked in him the eyes, and then dropped her gaze to his painfully erect cock.

JackKing
JackKing
1,694 Followers
12