Edward’s Halloween Costume – Exhibitionist & Voyeur – Free Sex Story

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Everyone in this story is 18 years old or older.

Janet, Edwards mother, was a stickler for authenticity. This became obvious while she was describing the plans for her Halloween costume party. “Every detail must be perfect down to the last one. Oh speaking of details, Mrs. Webster, the best seamstress in town, has been under the weather. She will be unable to come here to measure you to make your costume.”

“Since you couldn’t be bothered to be here when the rest of the family was measured, fitted and already have their costumes, you will need to go to her for that,” Janet informed him.

“Oh I’ll pick something up at the store to wear,” Edward stated.

“Like hell you will,” Janet replied. “I’ve invested too much time and money to make everything perfect for you to mess things up. Our themed family costumes will be coordinated down to the thread color.”

Edward gave his mother a snide eye as if, whatever. “Well if you’re going to throw one of your hissy-fits then I’ll go. You know she lives on the ‘other’ side of town, right?” He asked.

“I know perfectly well where she lives. You know you’ve grown up to be quite the snob young man. I don’t know where you get the idea that we are better than anyone else. True, we’ve had advantages over others but that’s no excuse to look down on anyone,” his mother said. “And just because her house isn’t as nice and it is located in a less desirable neighborhood should not make any difference.”

“Ok, ok, get off my back, I’ll go, mainly just to shut you up,” he said in his best superior tone.

The next day Edward hopped in his convertible sports car and raced to the ‘other’ side of town to Mrs. Webster’s modest ranch home. After knocking on the door several times he was turning to leave when the door opened.

“Hello, can I help you?” A girl, similar in age to his 19 year old self, said.

“Yes I’m Edward Van…” She interrupted him saying, “I know who you are and mom is expecting you. I’m Cora, her daughter,” she said, introducing herself. “Please come in, moms not been well so that’s why I answered the door.”

“Oh I’m sorry she’s been unwell,” he said, but she could tell it was just as a courtesy, it had no real meaning.

“Please follow me to mom’s sewing room. She does everything there. I mean measuring, fitting, sewing, everything.” Cora informed him as they made their way through the house. Upon entering the room he noticed how bright it was. The outside wall was nearly all windows. One wouldn’t need electrical lights except at night it was so filled with natural light.

Seated at her sewing machine Mrs. Webster was busy at work. She was probably in her late fifties, from Edwards determination. She was not overweight but pudgy. She sported a kind face but it was worn from time.

She turned and greeted Edward, “Well here you are. It’s about time. I was beginning to worry we were running out of time to get you costumed up for the party,” she said. “I’m sorry you had to come to us. It’s a shame you couldn’t have been available when the other family members were at your beautiful home for their fittings.”

“Oh me too, I hope this isn’t too much of an inconvenience for you,” Edward said again in such a nonchalant tone, nobody bought it.

Just then another girl burst into the room. “Oh Edward, this is my other daughter Beth. Of course you met Cora already,” Mrs. Webster said. Cora was a 20 year old girl neither gorgeous or ugly, she fell somewhere in the middle. Beth, the 18 year old was the more attractive of the two. Both were “common”, at least that’s the term Edward would use to describe them.

“It’s so nice to meet both, well all three of you lovely ladies,” Edward said again in the same condescending tone as before.

“Well girls now that all the introductions are over scoot on out of here so I can get started with Edward,” she said. “I’m sure you’ve got better things to occupy your time. But don’t go too far just in case. I’m still not 100% well, as you know.”

Edward wondered this a bit strange but then he wasn’t acquainted with how Mrs. Webster worked so the wondered left as quickly as it appeared.

“You know of course you’re to be a young caveman to match your mother, father and Sister, right?” she asked him.

“I had no idea what kind of costumes mother had picked out this year. I do know she likes the family’s costumes to have the same theme,” he answered. “It makes no difference to me what ridiculous costume she chooses,” he said in an insulting manner, or that’s the way Mrs. Webster heard it anyway.

“Well this years ‘theme’ is cavemen family’s,” Mrs. Webster noted.” Now let’s get started. Please stand right here,” as she pointed to a spot in the center of the room.

Edward strode over to the spot and stood there uninterestedly looking around the room.

“Ok Edward, I’m going to take some measurements. Relax, this will only take a few minutes,” she said. She started with his neck and arms, stopping only to write down her findings. When she was measuring his chest she felt something odd. “Edward are you wearing a unusually thick shirt?” She asked.

“No not really but I am wearing several layers of shirts. I’ve got my t-shirt, a pullover polo and then my button up oxford cloth on top,” he answered.

“Oh dear, that’s a problem,” she replied. “I need a more realistic measurement if your garment is to fit the way your mother likes.”

“Is that really necessary,” he asked.

“Well, yes it is. If I don’t get accurate measurements, the costume will not fit correctly. And we know your mother would not be pleased, with either of us, if that were to happen,” she emphasized.

“What do you need me to do so that your measurements are ‘accurate’?” Edward asked.

“For the very best results I’d prefer you to step behind that screen, as she nodded toward it, and disrobe down to your underwear,” she answered.

Edward somewhat taken a back said, “Is that really necessary? Do your measurements need to be that precise?”

“As you are aware your mother is a very detailed and exacting woman. She uses my services because she knows she can depend on my ability to please her. I must have the correct measurements to do that.” Mrs. Webster said.

“Fine, let’s just get this over with,” he spouted and huffed off to behind the screen. It took him a while to take off all the garments he was wearing. Before stepping out from behind the screen he looked down to observe himself.

He’d worn a pair of white bikini briefs. Why oh why had he not wondered about it and worn a pair of boxer briefs. That would have given him more overall coverage. But it was what it was, so off he trekked back to his spot in the center of the room.

“Ok let’s get this done and done,” he’d blurted out. He realized now he was standing in a woman’s sewing room, he barely knew, in just his briefs. This realization made him shudder for a second.

Mrs. Webster restarted her measuring duties again with his chest. The tape measure felt cool against his warm tanned skin.

“Oh dear,” Mrs. Webster remarked. “It’s a good thing we did this. I’m getting a significant difference from before with your clothes on.” She smiled up at Edward thinking he would be pleased. His resting bitch face indicated he could care less.

“Can we just get on with this…it’s somewhat uncomfortable standing here dressed, or more accurately undressed like this.” Edward said.

“Goodness, a grown boy like you, still getting embarrassed in front of an older woman like me. Thank you, that’s a backhanded compliment, even if you didn’t realize it,” she chuckled.

“I can understand some boys shyness about their body’s but you have developed inti quite the athletic handsome young man. You should be proud of your physique. It’s really no different than if you were standing here in a speedo swimsuit.” She said.

She continued trying to ease his anxiety by saying, “Besides I’ve seen young men in here in much less than you’re wearing,” she chuckled.

“WHAT?” He quipped back at her. “Anything less would be…they would be…naked!” Edward said questioning what he had just heard.

“Yes dear, there have been instances in which they would need to be completely undressed in order to fit their clothing properly. The fact that people have to completely undress at times is overstated. Take models during a fashion show, they don’t even wear undergarments most of the time. They are naked backstage while changing outfits during a show.” Mrs. Webster explained.

“Oh…I see,” Edward muttered. This still didn’t quell his anxiety about standing there only clad in his bikini briefs. He concentrated on being finished, dressed and out of this situation.

Mrs. Webster continued measuring his waist and hips. He squirmed somewhat while she took his hip measurement. Her fingers were uncomfortably close to his privates. Being a 19 year old boy, any activity that near his groin produces a reaction.

He felt his penis twitch while she fiddled with her measuring tape. His attention suddenly switched when he witnessed Cora and Beth casually walk into the room. He quickly moved his hands to cover himself, swatting Mrs. Webster’s hands away.

“Oh goodness, what happened?” Mrs. Webster asked. “I haven’t got the final measurement yet Edward.”

“Your daughters just walked in and…I’m…im in my briefs,” Edward announced.

Mrs. Webster laughing said, “Oh that, my daughters are my employees. They always help me in my sewing business. Cora has become just as proficient as me. She takes over for me at times when I’m under the weather.”

“But they have no right to just walk in on me when I’m not dressed,” he complained.

“Well they are a part of the business and this is their home,” Mrs. Webster replied. “I’m sorry if you weren’t aware of that but if you check with your mother she’d tell you she knew. The girls have worked along with me and your mother on several projects. She was very pleased with everything they worked on.

“It’s still very uncomfortable for me…like…like this,” he said.

Cora jumped in with, “Don’t be so self conscious. I feel the same way whenever I go to the beach. I’ll be wearing a tiny bikini, it seems like I’m not wearing anything,” she laughed. “We all have similar feelings about that stuff.”

Beth, standing next to her Sister, simply nodded her head in agreement.

Mrs. Webster spoke up insisting, “I know one thing for sure, I’ve got to finish getting your measurements,” as she as she gently pushed his hands apart and away. This gave the girls an unobstructed view of his package inside his briefs.

“Wow, those fit you like a second skin,” Beth commented looking at his briefs. “You could wear most anything with a nice create like yours,” she continued with her compliments.

Edward was loving the compliments but still uneasy with the whole situation. Finally Mrs. Webster said the magic words, “We’re done, you can get dressed now.”

As he turned and headed for the screen the girls noticed his bikini briefs revealed the top of his Ass crack. They looked at each other with a smirking chuckle.

“I’ll need you back in a few days for your first fitting,” Mrs. Webster announced as he dressed behind the screen. “I will let your mother know what day.”

Edward asked, “First fitting?”

“Yes as particular as your mother is about these things, I will need at least a few fittings to get things perfect.”

“I guess if it’s absolutely necessary, I just hope there is no conflict with my previously scheduled activities,” Edward smugly answered.

Three days later Edwards mother informed him that Mrs. Webster had called and was ready for a fitting. “Oh crap, do I really have to go back there?” Edward asked.

“Indeed you do. You’re not screwing up my perfect party. I’ve put a lot of work into this thing, and your custom costume goes along with ours,” Janet said. “Mrs. Webster asked if you could be there tomorrow at 2:00 pm.”

“Ok, ok I’ll go,” he said. “I just don’t like leaving my car unattended in that neighborhood. And those daughters of hers are creepy, if you ask me.”

“Now it’s not that bad of an area and besides Mrs. Webster is doing me a favor. She’s working you in because you were too ‘busy’ to get yours done with the rest of us.” Janet said. “Her daughters are a great help to her. They step in when she needs help and the older one is nearly as proficient as her mother.”

“Fine, I’ll go but mainly to get this silly thing over,” Edward said.

The next day he arrived at Mrs. Webster’s home just after 2:00 pm. Before he could knock on the door it opened. Beth, the younger daughter, greeted him saying, “Hi again, mom’s in her sewing room waiting for you.”

Edward followed Beth through the house and into her mother’s sewing room. “Aha Edward, it’s nice to see you again. How have you been?”

He acknowledged her and gave her the standard answer, “I’m fine, thanks.”

Mrs. Webster handed him the costume and began to explain its make up. “As you can see the caveman theme is clearly evident,”she giggled. “The costume is made from fake animal skins designed to mock the real skins. There’s a built in hidden undergarment. You couldn’t wear regular underwear underneath the flaps, it would show.”

Edward scanned the costume and saw that there wasn’t a lot to it. It consisted of a sash, similar to a beauty queens sash but in animal print and a bottom which was only two flaps. He presumed one flap for the front and one for the back with the sides open.

“I’m supposed to wear this?” He asked. “This is what my mother chose for our ‘themed’ costumes?”

“Yes, your family’s costumes are very similar. You’d know that if you had been there when we did them,”Cora popped in to say.

“Come now, let’s see how the fit is,” Mrs. Webster announced. “Take the costume behind the screen and try it on Edward.”

Behind the screen Edward stripped down to his boxer briefs and slipped the costume on over them. He stepped out and before he made it back to where they were, Mrs. Webster stopped him. “Edward, I told you the underwear is built into the costume.”

“I heard you but this is just a fitting. I figured I could wear my regular stuff underneath for this,” he responded.

“Well you figured wrong,” she laughed. “A fitting is just that. I determine the fit of the costume and just the costume. What you’re doing is like wearing a sock to try on a sock to see how it fits.”

“Well fuc…damn, ok,” Edward grumbled. He stepped back behind the screen and stripped naked. It felt very odd to be standing in a room naked with just a screen separating him and three women. He quickly slipped the costume on without his briefs and returned back out into the room.

“Now that’s better,” Mrs. Webster said. “Let’s see what needs to be done here.” She started looking, touching, adjusting, moving everything. She made the rounds from front to back making notes at every stop.

“How does it feel? I mean is it comfortable? Are there any places where it feels too loose or too tight?”Mrs. Webster asked in rapid fire.

“I guess, it really doesn’t matter. I don’t plan on having it on for long, if you know what I mean,” Edward smirkingly answered.

“Ok then, I just need to check a couple of more areas to complete this fitting.” Mrs. Webster said. Without warning she flipped up the front pouch revealing the built in underwear. Edward jumped in place when he realized what she’s done.

“I’m sorry dear I didn’t mean to startle you. I just need to check the fit of the built-in support garment front and back.” She then proceeded to stick her fingers all about the pouch. Through the thin cloth she grazed both his penis and balls in the process. This of course caused the normal reaction in a 19 year old boy. His member began to swell.

Just as Edward was about to start to stress, Mrs. Webster instructed him, “Now turn around so I can check the fit in the rear.” He was never so happy to accommodate her command. His penis was now semi hard but not visible under the front flap. After her inspection of the rear fit she allowed him to go and get dressed.

Before he started out Mrs. Webster said, “Great, we’re almost done. I’ll need one final fitting in a few days. I’ll let your mother know when.”

When he was just outside the front door his phone rang. He answered and stopped outside on the porch to talk. “You wouldn’t believe where I am,” he said into the phone. “I’m in a dump on on West St. My stupid mother insisted I come here to get my Halloween costume made. There’s this old creepy lady and her two nasty low class daughters,” he laughed. “It’s a fucking freak show. They are fucking skanks dude. They make my skin crawl.”

He was unaware that both Cora and Beth were close enough to hear every word he spouted. They were not happy with his demeaning description of them or their mother. They now confirmed what a spoiled brat he really was.

Before he was to have his final fitting Cora and Beth told their mom that they had done some extensive research on what actual cavemen wore. They explained that the younger males of the family had to dress differently from the elders. They needed more freedom of movement since they did all the hunting, fishing and gathering. In order to give them the ability to do all this, without hindrance, their animal skins needed to be much, much smaller.

They were so convincing to their mom she got in touch with Edwards mother and relayed her new found information. Janet listened and replied, “That’s wonderful and I appreciate all your daughters extra work on my behalf. If there’s anyway you have enough time to make the changes please do. You know how accurate I like things to be.”

Mrs Webster assured Janet she could accomplish the alterations with her daughters assistance. Mrs Webster told her that they would need an extra day to prepare but to have Edward be there at 1:00 pm the day after tomorrow.

It was an unusually Hot day for late October. Edward arrived at Mrs. Webster’s home with his sports car convertible top down. Somewhat wind blown he knocked on the door. Cora answered the door and welcomed the young man inside.

On their way to the sewing room she announced, “Unfortunately mother has been taken ill yet again. She’s been in bed since late yesterday afternoon. But never fear, both Beth and I have stepped in many times before and finished her projects.”

It could matter less to Edward, as long as the work got completed. “Well I guess that will have to suffice,” he said with a snobbish smirk. “Let’s just get this clutterfuck over and done with.”

Beth was waiting for them in the sewing room. “Great you’ve arrived, I hope you like the changes we’ve made,” Beth said.

“Changes?”, Edward asked. “Oh you mean the alterations from the last fitting I assume.”

“Didn’t your mother tell you about the last minute changes she had us implement?” Beth asked. Cora jumped in with, “Maybe she was just too overwhelmed with last minute party details to remember to mention them to you.”

“Whatever, no big deal as long as she gets what she wants,” Edward said. “You know how difficult she can be if things are not just as she expects.”

“Oh we know. She is the perfectionist of perfectionist,” Cora joked. With that said she handed Edward the costume as he walked toward the screen to change.

Once behind the screen he once again stripped naked. When he picked up the costume he noticed how light it felt in his hands. “That’s odd,” he wondered. As he slipped it on he noticed the fit was completely different than the last time. After it was on he looked down to find there was not much of the original costume left.

The very first thing he noticed was that the built in underwear was gone. His privates were just covered by the flaps, front and back. And the flaps were significantly smaller than before. There was less of everything. In fact there was barely any costume at all.

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