tagRomanceHalloween Damsel in Distress

Halloween Damsel in Distress


Author's Note: If you are looking for a graphic story, this is not the story for you. If you are looking for something fun, teasing, and even quite silly at times, I think you will enjoy this one. But please do know going into it that it is pretty tame compared to my usual stories. This idea popped into my head, and I had to get it down on paper. It just so happened to coincide with the Halloween contest going on. I had incredible fun writing this short tale and hope to do a few more like it in the future. Please enjoy and don't forget to vote!


Ding dong!

I adjusted my cowboy hat and hooked my thumb in my front belt loop, with my other hand resting on the plastic six shooter in its holster as we waited for the door to open.

"Trick or treat!" My son screeched before the door fully opened. I couldn't help but laugh at his enthusiasm.

"Aren't you cute!" Maria squealed from seeing Billy in his adorable robot costume and tossed some candy into his bag.

"Is Tommy ready to go with us, Mrs. Schmidt?" Billy said, loving every minute of this holiday.

"Almost, he's just finishing up putting on his costume. He'll be down in a minute." She said cheerfully and looked at me for the first time. "Hey, Jack! What happened to Lucy? I thought we were going to go together like we usually do."

"Beggin' your pardon, ma'am. But it would be my great honor to accompany you on this trick or treat chaperone excursion on this very fine, fall evening." I said with my best western accent as I tipped my hat to her.

"What is the matter with you?" She giggled and brushed her auburn hair behind her ear.

"Just tapping into my inner Halloween cowboy spirit. Lucy's actually not feeling so great, so we switched roles this year. She's passing out the candy, and I'm on daddy patrol. Hope you don't mind?" I said politely.

"Not at all. But you have on a costume. Jeez, I feel like slacker parent of the year." She said jokingly.

"This was hardly a time-consuming costume. It's basically a hat and toy gun on top of the flannel and jeans I usually wear." I said lightheartedly.

"Billy!" Said Tommy as he ran down the stairs in his ninja turtles costume. Both kids immediately started making exaggerated explosion noises and were instantly off in their own make-believe world.

Maria smiled at the boys having fun. "Aren't they lucky? So quick to use their imagination and dive into another world."

"That's what's so great about Halloween. You get become another person and escape into a fantastic new world filled with endless possibilities, if only for a little while." I said.

She nodded her head, quickly brushing off the idea.

"You could do it too. We just needs to find ya the proper outfit." I said returning to my goofy western accent.

"I really have no costumes waiting for me." She said, still laughing at my character.

"You just need to use a little imagination." I offered politely.

"Boys, why don't you go run and catch up with the Robinsons. I see them down the street. I'm sure you can tag along with them for bit. Mommy needs to find a costume." She said and gave me a playful wink.

The kids took off before she even finished her sentence.

She chuckled and watched them run off, giggling the whole way. "Why don't you take a look at what I have lying around in my closet. Maybe you can come up with something creative."

"T'would be my honor, ma'am." I said and tipped my hat once more as I walked through the door.

"You can stop with that silly voice." She giggled.

"Sorry, it's easy to get carried away when you're having fun." I said as I followed behind her. As polite as I was trying to be, I couldn't help but notice the way her jeans hugged her incredible, round behind that was right in front of my face as she led the way up the stairs. I saw their family pictures on the wall and reminded myself to snap out of it.

"Where's Greg, anyway?" I asked.

"He's on a business trip. Gets home today, but not for a while." She said as we walked into her bedroom.

She turned on the light in her large, walk-in closet and started to rummage through the hanging clothes.

"Do you mind if I use your bathroom first?" I asked thinking I better go now while I had the chance. "This cowboy drank a lot of moonshine and it's Slim Pickens for an outhouse out on the trail."

She giggled and covered her mouth, trying to conceal an even bigger laugh. "I thought the whole trail was a cowboy's outhouse?" She joked. "It's right through there, bronco." She pointed to the other side of the closet.

This was a newly built home, one where you had to walk through the closet to get to the bathroom. I headed over to the bathroom and should have guessed it, but there was no door to close on that side of the closet. There was one door to close the closet, but it did no good if someone was already in the closet. I walked in further and the toilet was around the corner, hidden from her view so I figured I had enough privacy. I lifted the seat, unzipped my pants and pulled out my penis. I kept thinking how little privacy I actually had. There was no door, no sound barrier. Snap out of it, she can't see you. Just pee and get out of here, I thought to myself.

I tried to force it, but couldn't quite get it started. I gave my penis a few tugs hoping to relax it. All that did was force a little more blood into it making it thicker and fuller, but not any easier to go. It felt like an eternity as I stood there in silence waiting until a stream finally formed and grew steadily.

"What about this? I could be a mad scientist?" She called out as she walked in holding one of Greg's white button shirts for work. "Oh shit, sorry." She said as she walked in on me still peeing, holding my penis out in clear view. She looked away instantly, but looked back. "I'm sorry, I thought you would have been done by now." She turned her body to the side, giving the illusion she was giving me privacy, but really, she was still looking out the corner of her eye.

"Guess I had a few too many at the saloon." I laughed, thinking we're all adults anyway and was relatively sure she didn't see too much. "I'm not so sure about that costume." I said as I was still going strong, and the sound of my stream hitting the water echoed in the quiet room.

"What do you mean?" She asked and walked over next to me to face the mirror. "I think it's a great idea." She said as she held the shirt up to her body and made eye contact with me through the mirror. Her eyes noticeably trailed downward as she looked at my reflection, but quickly returned to her shirt. "It's about as good as we can do on this short of notice I think."

My stream finally died down and I shook the last few drops from the tip. "Maybe. It's just so uninspired, though." I said as I tucked my penis away and zipped up. When I returned my gaze to her, she quickly looked away as if to show she wasn't watching at all.

"Uninspired? Who are you, the costume police?"

"No, ma'am. I'm an outlaw. I keep my distance from any kind of police." I winked and walked past her back over to the hanging clothes.

"Let's see here." I said as I mentally started eliminating several outfits right away.

"Take your time. I might as well get started putting on some make up while you're picking something out." She said as she walked back into the bathroom, out of my sight.

"Don't put on your make up now. We don't even know what you're going to be yet." I shouted and continued the search.

As I wandered around her closet I noticed a few bras on the floor, and a pair of purple panties clearly worn. They were turned half inside out, and you could just make out a slight discoloration on the part that would snug up to her most intimate areas. Without realizing it, I had picked them up and felt the soft texture in my hands when I heard her call out from the bathroom, "Find anything good?"

"Uhhh, no. Still looking." I said and tossed the dirty panties in the corner. What is wrong with you, creepo? I asked myself as I tried to remain on task.

"Wait a minute, wait a minute!" I called out as I grabbed a red dress that had a collar and some buttons on the top half and quickly ran into the bathroom. "I got it!"

"Jesus, Jack!" She yelled as she squeezed her legs together and slightly bent over to cover herself while she was now on the toilet.

"I thought you were doing your makeup?" I called out, only half looking look away.

"You told me not to!" She laughed and shook her head as she grabbed a wad of toilet paper. "Suppose it's only fair after I just walked in on you." She joked as she lightly parted her legs, just enough to reach down and wipe her slit that was hidden from my view.

I was silent and did my best to look away, but still snuck in more than a few peeks out of the corner of my eye.

"What is this wonderful idea of yours anyway?" She said and waited until I was looking at her before she stood up leaving her thick, but trimmed patch of hair on display.

My jaw practically dropped from watching this strangely intimate show. Did she want me to see that?

"Jack! Snap out of it, I was just peeing. We're both adults here." She said and couldn't hold back a bashful smile as she pulled up her panties and jeans slowly. "Now why do you have my old red dress from years ago? I actually forgot I still had that thing."

"This incredibly outdated dress is perfect." I said practically grinning from ear to ear.

"It's not that outdated." She said almost insulted. "What am I going to be?"

"Why, a damsel in distress of course." I smiled. "And I'm your cowboy hero here to save you, ma'am." I said returning to my accent.

"What makes you think I need saving?" She snapped.


"I'm only kidding. I think it's a cute idea." She laughed and grabbed the dress from me. "I'll try it on and you can see what you think."

I nodded and stood there waiting. She looked back at me curiously.

"Oh, shit. Changing. Right, I'll give you some privacy." I chuckled as I turned around and left the bathroom.

I looked around the closet as I was killing time, seeing more panties and bras lying around. It felt strangely intimate seeing them like this.

"What do you think?" She called out.

"You look great!" I said enthusiastically as I walked back in the bathroom.

She was staring at herself in the mirror, giving a few twists to view all angles. She had a great figure with impressive natural curves, but still had an overall petite frame.

"Hmmm, it still kind of feels like just a girl in a dress." She said and added, "If we're going to play up this role, I think we'll need to bump up the cleavage. What do you think?" She asked and turned toward me, as if to give me permission to look at her chest.

"Uhh, I think your cleavage is fine?" I said nervously. Seemed like an easy question to get wrong, so I played it safe.

"That's sweet of you, but I'm nowhere near damsel level yet." She looked back in the mirror and cupped both of her breasts, pushing them up and together creating cartoon like cleavage. "Can you look in my bottom drawer and find my pink push-up bra. I think it's the only pink one I have."

"Sure." I said uneasily, but still excited for the intimate task. Frankly I couldn't believe she was allowing me to go through her personal things. There was an incredible amount of trust there.

The drawer slid open easily and was a mess of tangled up clumps of panties, thongs and bras. My hands slid things from side to side, sifting through the array of intimate undergarments. There were so many kinds of panties in various shades of pink, it was not easy to find the sole pink bra.

As my hands dug deeper into the drawer, I felt something hard. My hand grabbed it, feeling the almost rubbery texture as I pulled it free. I had to restrain myself from laughing out loud when I saw I was holding a huge dildo. It was the kind that looked just like a penis with an engorged tip, complete with balls on the other end. It took me a moment to stop laughing, and I started to wonder if she wanted me to find this?

"Need any help?" She called out, probably wondering what was taking so long.

"Nope!" I said startled and dropped the dildo instantly. "I think I found it." There was a pink bra strap on the very bottom, far corner that I grabbed and pulled out a large, pink bra attached to it.

"Is this the one?" I asked as I returned to the bathroom, handing her the bra.

"Yes, thank you." Her fingers lightly touched mine as she grabbed it from my hand and quickly turned around. With her back facing me, she unbuttoned the top half of her dress and shimmied it down to her waist.

I watched, fascinated by the sight. I couldn't really see anything, but found it incredibly erotic seeing her bare upper back exposed. She quickly reached behind and unhooked her bra strap, removing it entirely. I couldn't help but feel slightly turned on at the thought of her being completely topless in front of me, even though her breasts were not in view.

She effortlessly slipped on the new bra, and readjusted her dress. As she turned back around, I noticed an immediate difference.

"Wow!" I blurted out, gazing at the newfound cleavage popping out of the center of her mostly buttoned up dress.

"Thanks." She said as she blushed. "So is this it? I'm still not sure it's right. Now I kind of just feel like a girl with bigger boobs in a dress. Am I just overthinking this?" She asked.

"Hmmmm." I said as I eyed her up and down. "It needs a few adjustments. May I try something?"

"I guess so." She said tentatively, but with a hint of excitement.

I felt like a tailor as I walked up to her, eyeing her proportions and noting where the dress was falling. "I think this might help." My hands slowly moved toward the top of her dress, and pulled the collar to the side a little more. My fingers were nearly shaking as I decided to unbutton her top button.

She watched carefully as my fingers got dangerously close to touching her exposed cleavage. I undid the next one, revealing even more of her cleavage, as her mouth gaped open as if to tell me to stop. But she just watched as I undid one more button. The dress was now undone to the middle of her stomach and most of the bra was completely visible.

"I can't go out like this..."

"Shhh..." I said jokingly as if to say that I wasn't finished. Truthfully, I'm surprised she let me go this far. I grabbed the top portions of her collar, and pulled up the dress a little higher so I could pull the whole collar down and over the sides of her shoulders. Now the top cut of her dress rested in line with the top of her bra. There was still ample cleavage spilling out, but it looked purposefully done. The bra straps almost looked as if they were straps from the dress. The new adjustment also raised the bottom of her dress a few inches, showing more of her smooth and toned thighs.

My own mouth dropped as I admired my work. I couldn't believe my idea actually turned out okay.

"Wow!" She exclaimed. "I actually do feel like a damsel in distress."

"It suits you." I said.

"Now let's add a little to yours." She said, starting to get into it.

"Mine? I thought I was good to go?"

"Almost, but you need just a little touch to really put you in the cowboy mindset." She flipped through some things hanging in the closet. She started to push in her bra drawer with her foot tomboy draw attention to it, but the dildo was sticking out preventing it from closing.

I tried not to laugh, but seeing the top half of a fake dick sticking out of a drawer was a funny sight.

She bent over and picked up her dirty panties that I tossed in the corner earlier and stuck them in the drawer and adjusted the dildo so it would close all the way.

She gave me an embarrassed look. Neither one of us said anything, but we both slightly giggled. She returned to looking for my extra piece of cowboy flair.

"Aha!" She handed me a black vest from Greg's side of the closet. "Here try this on. It should fit. Greg's almost the same size as you...in most areas." She said with a playful wink and glanced suggestively at my crotch.

I slipped on the vest and she walked toward me.

"Hmmm." She reached up and undid the top few buttons on my flannel shirt. I normally wear a T-shirt underneath my flannels, but for some reason I didn't today. As my exposed pecs came more into view, she raised her eyebrows and undid a few more until you could see just a hint of my toned abs.

She buttoned the vest, but still left my chest and abs visible. As much as I found it erotic to unbutton her dress, this was somehow just as intimate as I watched her carefully insert each button in its hole as she worked her way down from my chest to my waist.

"Perfect." She said as we both went into the bathroom to admire our homemade creations in the mirror.

"Well I'll be damned." I said. "We look like we belong on the cover of a cheesy romance novel."

"I think these bra straps showing might be a tad bit slutty." She joked.

"Maybe that's a part of your character." I said playfully and enjoyed the chance to take in the guilt-free view of her cleavage again.

"Maybe." She said with a playful smile and it was as if something clicked in her head. "Now I just need my big strong cowboy to come to my rescue." She said trying out a new playful drawl as she was starting to see the character come alive.

"What seems to be the trouble, ma'am?" I asked in a deep, raspy voice.

"Oh I couldn't...I could never tell you." She placed the back of her hand on her forehead and ran out of the bathroom into the bedroom in an overly dramatic fashion.

I followed behind her swiftly.

"Dontcha see? They're trying to run me outta town!" Her drawl got stronger the more she got into character.

"What makes you say that?"

"They don't understand. They'll never understand me." She said as she pretended to cry.

Even knowing it was all an act, it was hard to resist trying to help her. I grabbed both of her arms and pulled her in quickly to my chest. "I won't let that happen to you."

"Oh my stars." She broke free from my grasp and ran to the window.

"Why are they after you?" I asked as I caught up and stood behind her.

"Oh I wouldn't dare tell you that. You'd never look at little ol' me the same way." She said in a strangely endearing voice.

"Trust me ma'am, I've seen a lot of things in my day. You can tell me." I said in an exaggerated, raspy voice.

"Ohhh, they say I've slept with everyone in town! The sheriff, the barber, the bartender, the blacksmith, even the priest! Oh my!" She fanned herself dramatically with her hand.

"That's a lot of men." I joked trying to remain in character.

"It isn't true!" She gasped. "Ya have to believe me. I could never handle that many men having their way with my delicate body. The thought alone makes me tremble." She fanned herself again, hamming up her distress.

"I've only ever wanted just one, strong man to keep me warm on the lonely nights." She said resting her head on my chest. "A woman has needs ya know? That's how this whole thing started."

"How do ya figure?" I asked, slightly confused but gladly playing along.

"Now I never claimed to be a saint, ya hear?" She added.

"Believe me ma'am, I've done enough sinnin' for the both of us. You won't find no judgement here."

"Very well then, you see I was caught doing something...but not with another man." She said as if letting out the biggest secret she had.

"Another woman? You little...." I was interrupted with a playful and soft slap in my face.

"Don't you go gettin' the wrong idea about me. I wasn't caught with no woman. I was caught with myself." She said, sounding distressed and playing up her embarrassment.

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