tagFirst TimeAn Upset Halloween Plan

An Upset Halloween Plan


Everyone in the story is over 18 years old. This work of fiction is a product of the author's imagination and the characters, incidents or dialog are not to be construed as real. This story includes scenes of graphic sex and should NOT be read by minors or anyone that might be offended by such filth. No one should publish or post this story anywhere else without the author's written permission.

This is my submission to the Halloween Contest.

The length of this story is around 7,300 words and takes up 2 pages on Lit.

Tags used on this story are: first time, pussy eating, panties, milf, infidelity, blow job, nipples, big tits, costume, cougar

Category: First Time.


It was a late season BBQ in the Davidson's back yard with just their Son Todd and their next door neighbors Ron and Wendy Meyers. As was usual for these two couples, the wives were in the kitchen getting salads and condiments ready while their husbands and Todd were out by the grill, chatting and keeping an eye on the Meyers' younger toddlers playing on the lawn.

John Davidson came out of the house with two beers in his hands heading for the barbeque where Ron and Todd were standing near the grill.

"So Ron, I overheard Wendy telling Betty about some sort of game you two are going to be playing at the big Charity Costume Ball this year."

Mr. Meyers, Ron, gave his characteristic throat clearing, "hmm-hum", then looked back and forth between Todd and his Dad with a grin on his face.

"Well, the official version is that we are going separately, she's coming home from work, then going over to the hotel. I'm going to be at the office late and will go directly there."

"And the real version?"

"She thought it would be romantic if I found her there in costume and mask and acted like I was some guy trying to pick her up. And to top it off I'm not supposed to talk much, at all." Ron said wryly.

"What if some other guy shows up and tries to actually pick her up?" John asked.

"She picked out my costume. I told her that there's lots of Zorro costumes around, but she thinks it will be fun. On top of that I don't know anything about her costume, except that it's yellow." Was Ron's answer.

"You could have some fun chatting with other women for a while. After all everyone is supposed to wear a mask. You know, tell her you've been doing research, or thought they were her or something." John said as Todd's mind played with the erotic possibilities.

"Yeah, that would be great, not. What if I ran into Betty, or Fred's wife, Helen. That could get dangerous." Ron answered.

"Hey, Betty would flirt back at you for hours, but get too touchy-feely and she'd faint." John laughed.

"Yeah, but Helen would grab me and try to rape me on the floor." Ron chuckled and cleared his throat. "Hmm-humm.

"Yeah, with Fred watching the whole time." John was practically laughing now.

"He'd stand there and stutter, H' H' H' Helen, H' H' H' Honey? W' W' W' W' What are you doing, c' c' c' can I help?" Ron laughed again.

Todd was red in the face. Helen Rodgers was well built with huge tits, but a face that naturally seemed to scowl. He'd always thought she was cold and mad at the everything. This was a whole new world that opened up ever since he turned eighteen and his Dad and Mr. Meyers, started including him in their conversations.

From that comment and others it seemed that Helen bossed her husband unmercifully and had a reputation for being a nymphomaniac who tried to seduce other men constantly, and possibly succeeded occasionally. He filed that information away for future reference.

He had dated, and parked with several girlfriends in High School, but now, at nineteen, he was still the virgin his mother thought he was. It was a condition that Todd himself was ashamed of and tried to hide from his buddies. He tried just as hard to change the situation but so far things hadn't worked out.

He almost said something about the Zorro costume though. He had one as well. He had been at Hollies Costumes when Ron and Wendy had come in to get their costumes. He had come out of the fitting room after trying on his Zorro costume and saw them looking at the several Zorro outfits left.

There were a few variations in style and cut in the Zorro costumes, and Todd had picked the one that he thought was the best of the lot, and there was only one other of that variation left. He ducked behind another rack of costumes because he didn't want them to ask him to babysit their kids again this year. He did see that Ron had gotten the exact same type of costume he had.


"Todd," Ron said a little louder the second time.

"Yes sir?" Todd looked up startled, he hadn't been paying attention to the conversation.

"I assume you'll be relieved that we won't be asking you to babysit our kids this Halloween."

"You won't?"

"Now Ron, it's OK, he'll be happy to." John said with a smile at his son. Todd was trying to send urgent telepathic messages to his father to shut up.

"Nope, not necessary, we're giving them to Wendy's sister for the entire weekend."

"That's great Mr. Meyers."

"As I said earlier, it's Ron now, you're legal to vote now, you should call me by my first name."

"OK, uh Ron." Todd said a little hesitantly.

"You'll get used to it." Ron said with a smile on his face.

Todd blushed but was secretly proud to be allowed to listen to his Dad and Mr. Meyers as if he was just one of the guys. It made him feel grown up. Heck, he was well over eighteen now. He could vote. He took a quick glance at Wendy, Mrs. Meyers, as she and his mom came out with the salad bowl and a tray of condiments. He admired Wendy's figure. He'd had a crush on her for years.

A little spark of fantasy occurred to him, what if, what if he was in the same costume as Mr. Meyers, and he was at the party ....He would have to explore that fantasy when he was alone in bed tonight. He gave a little shiver.

"I hear Hollies has got a huge load of costumes, some pretty good quality ones, this year." Said John.

"Yeah, after the fiasco a couple of years ago he must have lost his shorts. He can't do too much just selling sports outfits and menswear all year. There was a lot of choices, heck there was a whole rack of 'Zorro' outfits, must have been two dozen."

"Yeah, Betty and I are going down Monday after work to find something. Todd, do you want to come too, aren't you going to that costume party at the Community College?"

"I already got one Dad, I stopped by earlier this week. There's a party on campus and I've got a date, sort of."

"Sort of? What kind of date is that son?" Asked John.

"Well, I asked her to go, and she said she wanted to, but her parents have something planned, and she'll let me know later if she can get out of it."


The few weeks before Halloween went by quickly with only a few things of note happening. Todd found out that his date couldn't get out of her prior obligation. He half suspected that the story she told him earlier was a stall in case someone else asked her out. He knew he had to go with a student there, and he didn't know any other girls that went there well enough to ask if he could go with them.

While he intended to start college there next year, he was earning money to help pay for it during this 'gap' school year. He thought about taking the costume back, but never got around to it.

The other thing was that on the Wednesday before the Ball, when he got home from his job. He saw both his Mom and Mrs Meyers dressed in their costumes. Both were dressed in early nineteenth century 'empire' waist costumes, they could have stepped out of a Jane Austen novel.

Mrs. Meyers in particular was stunning. The pale yellow gown flowed to the ground from where it was gathered just below her breasts. Its simple lines gave hints of her body as she moved. He fixated on the thought that she might actually be bare underneath.

It was hard to imagine this gown way back then, but he had seen pictures of paintings in books on the coffee table for months as the two women talked about and made their own costumes. The bodice was low and seemed designed to show a hint of cleavage. He thought they were as sexy as anything he had seen at prom.

As he got a glass of water in the kitchen he heard Wendy Meyers discuss with his Mom the game she was going to play with her husband.

"You be careful Wendy, there might be other Zorro costumes there and what if you find out that your Zorro is the wrong one." Betty said.

"Oh, that will be part of the fun. I can always scream and Ron will come running." Wendy laughed as she said this. Then she continued.

"In fact, that's part of my plan. Ron's been so busy at work the last six months that he's missed half a dozen date nights with me. Several times he didn't even call and tell me. I sat around waiting for him so long one time that I kept getting hit on. I was so mad I nearly went off with one of them."

"You wouldn't! Would you?" Exclaimed Betty.

"It would serve him right. You know he cheated on me once don't you?" Wendy went on, in a slightly lower tone of voice. Todd just froze, he was quiet as a church mouse hoping to hear more. He was glad he had been quiet about coming in, hoping to make it up to his room before his Mom could ask him to do any chores.

"You didn't really, but once you let some hints drop, what happened?" Betty asked.

"It was a mix up, sort of, and I told him I forgave him, but I didn't really. What happened is that a few years ago he was spending a lot of time traveling for the company, a lot of nights away from home."

"I remember that," said Betty, hoping to keep the conversation flowing.

"Well, we had a fight, a real knock-down-drag-out. He went on a trip and the first night he was there we got in another fight on the phone. To this day I can't remember what it was all about."

"Oh I hate those, but everyone has a fight now and again." Betty soothed.

"I know, but I said something like, 'if you aren't happy with me you should find someone else.' and he said, 'I just might,' and slammed down the phone." Wendy said.

"Wow. And he did?"

"Yeah, but I didn't find out until much later. He was real sheepish when he got home. We made up and it was all forgotten. Then a year or so later he was supposed to go to the same city, and he refused to go. I never would have know but he made some excuse about planning something with me, and his boss called me to apologized and tried to talk me into letting him go." Wendy continued.

"And you didn't know anything, so you asked him about it." Betty prompted when Wendy got a far away look on her face.

"Yup, and he broke down and cried. He said he never wanted to go to Atlanta again because it reminded him of the bad feelings he had, and also what he did about it. I had no clue what he was talking about." Wendy continued.

"Wow, what happened." Betty asked.

"The poor sap got down on one knee and confessed and asked me to forgive him. It was with someone that works in the Atlanta office. And I have to say he's been much more attentive since then. But lately he's been having to take more and more trips." Wendy said.

"So you forgave him." Betty asked.

"Yes, that's what I told him. But I also told him that I owed him one night out if I ever got that mad at him again. The guy was so cowed he even agreed to what he called get-even sex." Wendy was looking a little distracted as she said that. Todd noticed that her nipples were poking through her dress as he peeked around the door.

"You wouldn't really do it though. Oh, that's so exciting though, like a free pass," Betty whispered.

"No, I don't think I ever will. We're past the bad spot, still, there's time when I'm alone with my battery operated friend and I daydream about it." Wendy confessed.

Both women giggled, Todd was fully and uncomfortably erect in his jeans, he peeked though to the living room again and his eyes fixated on Wendy's erect nipples. Then Wendy spoke again.

"He promised he wouldn't go away as often, and without telling me ahead of time, but he still goes away sometimes, I still get lonely, and sometimes I think of things I shouldn't." Wendy had the far away look in her eyes again.

Todd crept to the back door and opened and closed it loudly before practically running up to his room, his face red. He took a quick glance at the two ladies and noticed that Wendy was facing away and it looked like her hands were over her breasts. His mom was right next to her.

Then, just two days before the Costume Ball on Friday night. The evening after Todd had eavesdropped on his mother and Wendy, their phone rang right after supper.

Betty's mother called. Betty's father had fallen off a ladder and she asked if Betty could make the 3 hour drive on Saturday morning and stay the weekend to help out.

Betty agreed, and did better than that. She insisted that John go with her, and that they leave Friday morning so John could help around the house and help his father-in-law get settled in with his broken leg. He could also take care of any 'man' chores around the house. They would leave Todd home alone, and asked him to tell the Meyers' that they wouldn't be at the party.

They spent the rest of the evening packing and discussing plans, and telling Todd that he was old enough to be left alone. They left him money for emergencies and Betty briefed him on what supplies were in the kitchen for him to prepare meals with.

Later that night, when Todd was alone in bed, he had some wicked ideas, he realized that his parents hadn't thought to cancel the hotel reservations they had for Saturday night. It felt like a perfect storm of happenstance that would get him into the big party without parental supervision. A ball supposedly for only adults over twenty-one, with a cash bar.

Very early the next morning Todd's parents left, After helping load the car with their luggage, Todd hugged his mom and shook his Dad's hand, and watched them drive off. He went back to bed for a couple of hours.


As Todd headed out to get into his car later that Friday morning to go to work, he saw Mr. Meyers' car backing out of their garage. He waved and saw Mr. Meyers stop. He walked over to the car window.

"Hi Todd, your folks all ready for the party tonight?"

"No sir, they left early to help out my grandmother. Grandpa fell and broke his leg, they'll be there all weekend."

"Your Grandpa going to be all right?"

"Oh yeah, he's getting out of the hospital this afternoon. But he'll be off his feet for a while." Todd said.

"Well, take care of yourself, and stay out of trouble. We won't be around until Saturday afternoon, we're still going to the costume ball." Ron told the nineteen year old.

"I'll be fine, Mom and Dad left money to get by on, and there's lots of stuff in the kitchen, I'll be fine." Todd assured his neighbor.

"O.K., I've got to get to work, Oh, uh, you heard me tell about the game Mrs. Meyers and I are playing didn't you?" Ron asked.

"Yeah, at the cookout in our yard," Todd answered.

"Well, the thing is that as part of the game, Wendy is going to leave her cell phone off, in fact she might not have it at all. So if anything happens you have to call on our home phone, or call me," Ron said.

"That's OK, I don't know your cell numbers, but really, I'll be fine." Todd assured him.

"I need to give them to you when I get home, but I've got to get going, see you later on, Wendy or I will check our home answering machine remotely just in case," Ron said as he put his car in gear and backed out on their road and pulled away.

Todd had a normal day at work, and eventually it was over. It was strange coming home to an empty house, knowing it was going to be empty all weekend. In fact he took his time, and got home a little later than usual, with a meal from a fast food restaurant beside him in the car.

As he got to the door he heard the house phone ringing, but didn't get to it before it stopped. Later he thought to check the answering machine. He played back the message, it was from Ron, Mr. Meyers.

"John and Betty, and I guess Todd since your folks are out of town. This is Ron. Look I've done something stupid, I left my cell phone at the office and I'm calling from the airport. I can't get hold of Wendy. Please go over and tell her I'm all right. I've already left a message on our home phone, but she might not check it.

"I got word last minute this afternoon that I have to take a flight to Chicago for an emergency meeting with a customer. They aren't happy and I'm the go-to guy to sooth ruffled feathers. I'll get a temporary cell in the morning and call then. Got to go they're calling my flight."

Todd went next door and knocked but Mrs. Meyers wasn't there. He figured that she had left to go to the party, probably left early to get dressed in her hotel room. He hurried back home and wrote a note explaining and slipped it under their door.

He didn't know either of their cell numbers, just their home phone, and he knew that Mr. Meyers had already done it, but he left a message just the same. Then he had an idea. Go the ball. Why not? His parents had tickets. They had a room reserved didn't they?

Whenever they called to check on him, they called him on their cell phone, hardly ever on the home phone. they would never know if he wasn't home! He walked into the kitchen and the tickets where still there, stuck to the refrigerator door with a magnet advertising a local dentist.

And if they did, he could tell them he was trying to tell Wendy Meyers that her husband had left town. He had to get into his costume to get into the ball to find her. This way he could buy a few drinks, only over 21 types ever went here. He'd leave the mask on and no bartender would ask for ID. And even if he didn't drink, he could have fun.

It went as planned. Even his nervousness checking in at the hotel didn't phase the hotel clerk. Todd was asked if the room was going to be on the credit card they had reserved it on, and he said no, and gave his own card. It didn't have a very high limit, but he always paid it off, and there was no problem with the different first name.


So a few hours later Todd wandered through the hotel ballroom dressed as Zorro, complete with mask and sword. He had no fear about his parent's finding out, and if they did, well he was sure he could talk his way out of things if he didn't get into any trouble. He had a few beers, illicitly, in high school and he knew his limit. He would stay under that. Mostly he just wanted to see what went on.

Once in the ballroom about the only thing the nineteen year old was thinking about was how all these supposedly ordinary housewives had transformed themselves into gorgeously costumed seductresses. He guessed it had something to do with the masks everyone had to wear. That and the very low bodices that some had, as well as very short and revealing dresses that others had on.

The ballroom was huge, and there were several rooms that led off of it, he could see that several meeting rooms had been opened up to create the large space. There were several hundred people, a live band playing old classical style dance music. Well if he had to he knew he could handle it, his Mom had forced him to learn to waltz and to foxtrot.

There were three cash bars and several tables with nibbles and non alcoholic punch, ice tea and water available. He had already downed a beer but at a steep price. He figured part of the profit had to go to the charity. He had even bought one of the raffle tickets. He didn't see anybody he thought he recognized.

People were grouped together in clusters that obviously knew each other, and others were wandering around alone like he was, or in pairs, just people, or perhaps costume, watching. Not much was happening except on the dance floor. He mentally shrugged and headed that way.

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by49greg© 8 comments/ 60472 views/ 21 favorites

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