The Princess, The Pirate, The Witch

This is my entry into the 2023 Halloween contest. I always like to reinforce that (like my author name say), all of the stories I tell here have a basis in truth and are always based on actual events from my life. That being said, I do like to add some twists & embellishments to keep them interesting for the readers.

Please remember, authors & our stories thrive on ratings. We get better with feedback, so PLEASE leave your comments on our stories. I also love when people guess in the comments what parts are "Truth" and what I added for "Twists"

Everyone in the story is 18 years of age or older.

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My wife Sherri was the Assistant Principal at a private school that held an annual fundraising event every fall. The Fall Ball was when parents and donors would pay for tickets to attend a night of drinking, dancing, entertainment as well both silent and live auctions. Because the function was usually held a hotel, a lot of parents would book a room to avoid driving after an alcohol-fueled night. One year, the event was scheduled for the weekend before Halloween, so the PTA committee decided to make it a "Costume Ball" for the first time.

Part of Sherri's job was to be the faculty representative on the PTA and as a result she was heavily involved in the planning. The rest of the committee consisted of volunteer parents, mostly mothers, who managed everything from donations to ticket sales to the event itself. Somewhere in the planning stages, the committee members decided it would be fun to do a "group themed costume" and their pick? Disney Princesses.

Sherri came home one night after a meeting and I was waiting with a glass of wine thanks to her text, "Holy Fuck. You better have wine ready for me after this meeting." When she came in, she kicked off her work heels, fell into our cushioned sofa and started to recap the meeting for me.

"The problem is these women all need a hobby - besides this event" she started. "They debate EVERYTHING from the color of the cocktail napkins to whether we should have Sharpies or regular pens at the auction tables."

She continued to talk about the meeting until she got to the crux of her story, "And then ... we had to decide who was going to be which Princess. June immediately claimed Cinderella and said that we couldn't have two of the same princesses. Kiley got upset and said that she is a NATURAL blonde, so she should get to be Cinderella and June could be Aurora. Well, that pissed off Marie who wants to be Aurora AND it pissed off June who didn't like it being pointed out her hair isn't natural."

"Ha!" I interjected. "What happened from there?"

"Well, then Laurie said she was going to be Princess Leia and June told her that she's not a Disney Princess."

"Well, technically ... Disney owns Star War..."

"Shut up, nerd. Let me finish. So THAT went on for a few minutes. At one point, I had a few grown women screaming at each other, two women crying and the rest of us wishing we had stayed home. Oh, and one very confused father who regretted volunteering to put together the slide show."

"Poor Lenny. So how'd it end?"

"I ended up pulling rank and making the decision for everyone. Basically, I said it's supposed to be a fun event and if there are two Cinderellas or ten Cinderellas it won't matter."

"Nice. So which princess are you going as?"

"I have an idea, but I'm not telling anyone, including you, yet!"

"C'mon! You can tell me! Slutty Snow White? Maybe a sexy Moan-ana? Dress up so I can Poka-your-hontas?"

My wife picked up her wine and heels and left the room shaking her head, "There's something seriously wrong with you, you know that, right?"

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Weeks went by and on the day of the event, Sherri went to the hotel where it was taking place early in the day to help set-up. I followed later and checked us into our room that we had booked. (Our young daughter was spending the night at the house of one her friends.) In the time that had passed, I decided to stick with the Disney theme, but I went in a slightly different direction - Captain Jack Sparrow! I thought it was a fun costume, kept in the spirit of the night and would let me drink and stagger around, all in character.

I went down to the ballroom to check on the preparation for the event and saw all the volunteers bustling around setting up decorations and auction items on various tables. Sherri handed me the keys to her car and asked if I could grab her bags and bring them up to the room while she finished some last details. I unleaded her suitcase, a huge garment bag, plus a big box that held what I assumed was her costume. I was tempted to peek but decided to just follow instructions, then settle in to watch some college football until it was time to get ready.

The hotel room we booked was a small suite divided into two parts. When you entered, you stepped into a small living room area with a pull-out sofa-bed and a desk there was a little half-bath by the door. The bedroom and bathroom were through a separate door across from the sofa.

I was sitting on the sofa, with a beer I grabbed at the bar, when I heard voices outside the door. The electronic lock triggered, and I looked up to see Sherri entering with someone close behind.

"Hey Babe! You decent?" Sherri called out. "Grace is with me!"

I looked past Sherri and saw Grace walking in behind her. Sherri stood at 5'5" and Grace seemed to stand a bit taller, but this may have also been an illusion caused by Grace's mane of curly red hair. She was obviously of Irish decent with bright green eyes, pale skin and tendrils of dark red hair spilling down over her shoulders, nearly reaching the middle of her back. Grace had on a pair of skinny jeans and tight black top that clung to her, showing off her toned body. Her chest was small, but when she turned, I got a look at her solid filling out her jeans. She was a natural beauty who could always light up a room with her smile and laugh. She had on a pair of calf-high boots that women love to wear in Autumn and I gave her an appreciative look as she walked in dropping her bags on the nearby chair.

We had hung out with Grace and her husband, Andrew, a few times over the past few years. They were both easy to socialize with and the nights were always fun. Grace and I had a fun, flirty rapport that usually caused our spouses to roll their eyes at us. Unfortunately, in January, Sherri came home and told me that Grace and Andy had separated. Turns out, he had been hiding a gambling problem and had done some serious damage to their savings. It all came to a head over the holidays, and she threw him out. Since then, Grace had to get a job teaching at a different school just to keep her head above water. Her mother moved in with her to help with her son and the expenses.

"Hey Grace!" I called out as I stood. "What's going on?"

"Not much, Jay! Thanks for letting me crash your suite."

"I told Grace she could get changed here. That way she doesn't have to drive all the way home and then come back." Sherri added.

"Sure! No worries. I'm happy to help either or both of you into your costumes." The comment earned me an eye roll from Sherri and a giggle from Grace. Her bright white teeth spread open in a big smile as her crimson mane followed her into the bedroom. My wife spoke up,

"You're an idiot. Why don't you really make yourself useful and go get Grace and me drinks at the bar."

Again following instructions, I ran down to the hotel bar, grabbed a bottle of wine and a couple of glasses, and then returned to the room. The three of us sat and chatted since we had time before we had to get ready. After an hour or so, we realized it was time to start getting dressed, but adding a third person to the room caused some logistical issues.

"Babe, do you think you could get ready in here if Grace & I use the bedroom and bathroom?"

"Not a problem. Just being able to tell everyone that I had two hot MILFS getting naked in my hotel room is a story I'll be telling for years."

The door to the bedroom was closed firmly in my face telling me it was time to focus on my own costume. I spent nearly an hour getting into costume, adding a beard and eyeliner, fake tattoos and what seemed like a ton of accessories. By the time I finished, I was a passable substitute for Captain Jack. I was making final adjustments when the bedroom door cracked open, and Sherri's head peeked out.

"Can you give me a hand with the last of the costume? Grace is finishing up in the bathroom."

When we were first together, Sherri was a tall, thin blonde with small perky tits, tight ass and long lean legs. There was an old store, "bebe", that Sherri could have been the perfect model for. But age and motherhood does change things. Over the years, she had filled out in a good way. Her breasts were now larger and fuller and were just as sensitive before which gave me more to grab, lick and touch. Sherri's long blonde hair was gone, she now had a close-cropped platinum cut that was in style. Her ass was larger, too, but her workout schedule had it toned and looking full and sitting high on her frame.

Sherri opened the door and stepped into the room, encased in a long black gown with flowing sleeves and a low-cut neckline. There were purple details in the sleeves and around her neck and flashes of purple in the long slits up the sides of the gown. I was surprised at the way her breasts were supported and showcased especially for a school function. They were round and firm with protruding cleavage over the top of the dress. She had darkened the makeup around her eyes, had on long fake eyelashes, and had created some sinister angles at the corners with green and purple eye shadow. Lastly, her lips were coated in a deep red lipstick making them look wicked and sexy at the same time.

"Holy shit. You look amazing! Maleficent? That's your princess?"

"Yup" she laughed. "I figured since the kids all think I'm evil and I had to yell at all the princesses, it would be the perfect choice!"

"And you look hot in that. You really going to wear that in front of everyone?"

"Sort of. That's why I need your help." She handed me a big black cloak with a purple collar designed to spread up and around her neck. I took the cape and helped her secure it around her neck. When it fell around her, I could still see the details of her gown, but she was much more covered, especially her breasts and cleavage. She pulled on a pair of black boots, then went back to the bedroom and brought out the horned headpiece that would complete her look.

"I like the evil you!" I said using a terrible Jack Sparrow accent. "Can't wait to let you cast a spell on me later tonight, savvy?"

"Well, in that case, I'll give you a quick peek at the hidden treasure." She spread open her cloak and lifted her gown at one of the high side slits. As she did, I saw that her black stockings ended at her thighs and were being supported by garters connected to a lacy garter belt. A miniscule purple strip of shiny satin covered her shaved pussy leaving all but her slit visible.

Before I could say anything, we heard an awkward gasp from the bathroom door and saw Grace standing there, staring in our direction, a blush rising on her pale cheeks.

"Oh! I'm so sorry" she blurted trying to turn away. Even in the awkward moment, I saw Grace was wearing a perfectly suited costume to her looks. She was in a long, velvety, emerald green dress with long sleeves that covered her arms. There was a leather belt cinched around her waist that highlighted her figure. Her long red curls flowed around her face and over her shoulders to her exposed collar and chest. Slung over her shoulder and back she had a plastic bow, and quiver of arrows to complete the look: Merida from Brave.

Sherri dropped her gown and cloak and smiled back at Grace. "Don't be embarrassed sweetie! I'm pretty sure you saw me pull them out of the bag earlier. You just got to see them on me, too!"

Grace smiled, but I could still the flush of embarrassment in her cheeks from unintentionally interrupting us. I helped Sherri secure the headpiece on her head and we all went to the party.

Without going into a ton of detail, the event was a great success. Everyone ate, drank, and bid in the auction. The Princesses all took a picture together, with the evil Maleficent in the middle of them all. The magician they hired was amazing and just cheeky enough to entertain the adult audience. Of course, with that many adults being out without their kids, we all took advantage of the bar. As the night started to end, we were all pretty tipsy, including Grace who was laughing and giggling with some of the other moms.

I checked out at the auction table and quickly found out that in my buzzed efforts to support the cause, I had purchased more than my share of prizes and baskets in the auction. I had to run to the lobby and ask one of the bellmen to bring a cart and transport it all up to the room for me. After close to 30 minutes, I stumbled (allegedly just in character) back into the ballroom to find that most of the guests were filtering out.

Sherri and Grace were sitting with some of the other parents as I sauntered over, taking a seat at the table.

"Avast wenches! Be there any room for Captain Jack Sparrow?"

"Only if he's going to get us all a round of drinks"

"Aye. M'lady." I went to the bar where I got one last round and brought them on a tray back to the table. After handing them out we all toasted a successful night.

"Drink up, me hearties, Yo Ho!"

The group started to break up when Sherri leaned over to me, "I don't think Grace can drive."

"Is she that gone?" I asked.

"Yeah. She's been drinking quite a bit all night. What should we do?"

"Tell you what. Take her upstairs, since her stuff is up there, anyway. Let me talk to the desk and see if they have any rooms."

"Babe. I'm not sure she can afford one."

"Don't worry about it. With what I spent tonight, one hotel room won't break me." I stood up and headed to the lobby.

"Wait! What do you mean 'with what you spent'?'" she called after me.

15 minutes later, I was in the elevator feeling defeated. The hotel was completely sold out because of the events being hosted. I quickly realized that my night with an uber-sexy witch wasn't happening with a guest sleeping in our room.

When I entered our room, I saw the pile of baskets and packages stacked against the far wall. Somehow, in my inebriated state, I had collected quite the array of prizes. Sherri and Grace were looking through my treasures with amused looks on their faces.

"What in the hell did you buy?" Sherri asked. "And did we really need a kids' gardening basket?" Both women giggled as I joined them in looking though the pile of cellophane and tissue paper. As I opened one, my face lit up.

"Yo ho ho, and a bottle of rum!" I exclaimed as I pulled a bottle of expensive rum from one of the baskets. "Anyone want a nightcap?"

I poured us three glasses of the amber liquid over ice, then excused myself to the bathroom where I used some makeup remover to take off my fake beard and makeup. I removed the heavy accessories to my costume and went back out into the living room in just my baggy pirate pants and shirt.

Sherri and Grace had similarly removed some of their costumes. Sherri was sitting on the coach, still in the black and purple gown. Her boots were on the floor, and I could see her nylon-covered feet tucked under her. Grace was in a chair and had taken off her shoes, quiver and belt and was sitting with her big green dress tucked around her. I settled in next to Sherri on the couch and she leaned back to rest against me.

We all toasted and chatted about the event, the various people and all the gossip that came with an event like that. At some point, I refilled all our drinks and we continued to chat and relax. As expected, the conversation turned to Grace and her situation. She got emotional talking about what Andy had done and how much her son missed having his dad around. Sherri and I were very careful not to criticize nor comment and basically just listened. Whether it was the liquor or emotion or a combination of both, Grace eventually had a stream of tears streaking her cheeks as she talked about how lonely she was.

"I'm sorry." she whimpered. "I didn't mean to bring you guys down. I'll be right back." With that, she stood up, staggered a bit, and walked to the bathroom in the other part of the suite. Once the door closed, Sherri rolled slightly to her side so we could talk quietly.

"I feel so badly for her" she started. "Andy really fucked her over."

"No shit. I had NO idea how much money he blew and how much he left her in the lurch." As I spoke, I looked down to see that when she shifted, Sherri's Maleficent gown had opened slightly up her extended leg. I could see the top of her black thigh highs and some of her exposed skin. I could see the curve of her thigh and her bare ass cheek peeking through the open slit of the dress.

Sherri must have felt me slightly harden at the sight of her because she slumped her head against my shoulder and half-whispered, "I'm so sorry babe. This isn't what I had planned for tonight. But she has nowhere else to go and I feel so sorry for her."

"I get it." I replied. "It definitely sucks, but maybe you can save this outfit for when my birthday rolls around." I shifted my hand slightly and ran my palm up and down her skin, opening her dress a little more.

Sherri nipped and nibbled at my neck, sensing my building arousal. "Up to you. I was going to go with sexy cheerleader for your birthday, but I can do evil witch instead." She then leaned up and planted a kiss on me. Just as she started to pull away, we heard a sound from the door.

"Shit! Shit! Shit! I'm such an idiot." Grace cried out. She had washed off her makeup, but her eyes were still red and puffy from crying. She was staring down at us and had a clear line of sight to my wife's exposed thigh and ass and her long nylon-covered leg. Our body positions gave away our actions and there was awkward silence for a few seconds before she continued.

"You guys had a whole romantic thing planned and I ruined it because I got drunk and can't drive! I'm so sorry." Tears were now running down her face again. "I'll get out of here and give you some privacy. I'm so sorry. Shit."

Sherri stood up and moved toward Grace, "Grace, honey, it's ok. You're not going anywhere. You can't drive and Jason checked already, there are no other rooms."

"Fuck. It doesn't matter. I couldn't afford a room anyway. And if I go home, I'm sure my mother will give me lecture." A humorless laugh left her mouth. "Fucking perfect. 36 years old, separated, single mother, and somehow still going to get scolded by my mommy."

Sherri wrapped her up in her arms a bit tighter as she started to sob even more. "Bad enough I've fucked up my life, now I'm messing up yours. I'm so fucking cursed that even though I haven't had sex in close to a year, now I'm taking it away from others. I'm like a black hole of romance."

My wife continued to hug and stroke her friend's back in their embrace, "Honey, it's not your fault. Stop blaming yourself. You've been stronger than 90% of the women I know. Supporting yourself, digging out of debt, taking care of your son. You're an amazing, strong woman."

Grcace's breath started to calm down as Sherri rubbed her back and started to stroke her long, red hair. I saw my wife glance over at me for a brief second before she continued with, "But not having sex? That's unacceptable. Turn around."

Grace pulled away with a confused look on her face, "What? Why?"

"Because the way I see it, you have two options. Lay out here and cry yourself to sleep on a pull-out sofa bed, or..." She turned her friend around and reached under her hair to the top of her zipper, "Let us show you just how attractive and sexy you are."