Yet Another Halloween Story

By fawn embers

Published on Dec 10, 2002

Transgender

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Yet Another Halloween Story By Fawn Embers Copyright 2002, Fawn Embers

Disclaimer:

This is fiction. If you can't deal with erotica, then you should go visit someplace else. This story involves graphic encounters between men and women, men dressed as women, M-M-F Bisexual sex, and solo sex. If these things don't turn you on, then this story isn't for you.

Prelude:

Yes, I know that Halloween Stories are a dime a dozen. But this was my first experience in dressing in public. Chances are most people's first public outing is Halloween; since it is one of the few times of the year that public taboos are particularly loose. Anyway, I hope you enjoy this little story, and I'd love to hear your responses. You can email me at fawn_embers@yahoo.com. Don't be shy, but flamers will be deleted.

Chapter One: Getting Ready

It started innocently enough. I'm pretty famous, at least locally, for my Halloween costumes. Most of my friends wanted to know what I'd be dressing as this year. Usually I'm a monk, or death, or something robed, mainly because it was the almost like wearing a dress I felt comfortable doing in public. But I always went all out, making the costume, makeup, props and the whole bit. This year I hinted that I would be coming as a woman of some sort.

Well, one thing leads to another, and I'd been talked into dressing like a French maid. Mind you, it wasn't a difficult job convincing me. It has always been one of my deepest fantasies. That, and a schoolgirl. Yes, I know. That's terribly predictable of me.

As Halloween got closer, and the annual bash loomed larger, I got more and more afraid. I wasn't sure I could go through with it. In fact, I pulled out my "Angel of Death" costume from a few years ago, all black and leather and winged and safe. But I continued making the French maid outfit. Just in case.

In the week before the party several of the women I know (and occasionally talked into a date) called me or stopped by the house. They wanted to know how the costume was coming. I got a few pointers, lots of suggestions and tons of encouragement. Thanks to them I actually felt like I could pull it off. So by Halloween, I had a completed costume that I felt comfortable wearing in public, at least to the party. And I'd talked my friend Donna into meeting me at the party a little early to do my make-up. All was good.

Before heading over to the party, I did a little preparation at my apartment. First I slipped on a black garter belt. Then I slid on a pair of fishnets, clipping them to the garters. Originally I was going to wear panty hose, but Donna talked me into the garter belt and fishnets. I'm glad she did, it felt wonderful and defiantly got the attention of my cock. By the time I had the hose all gartered and situated, I was sporting a raging hard on. I tried to ignore it, and started to slip on the black lacy panties with the white ruffles that I bought for the evening. But before I could get them into place, I noticed that I had already started leaking. Not wanting to stain my panties this early, I decided to relive the tension first.

While I might have been worried about dressing in public, there is one place where I'm often seen dressed. Not wanting to relieve myself alone, I logged onto my Yahoo! Messenger, and logged into the Men In Panties chat room. I turned on my web cam, and set it to automatically connect to whoever wanted to look. As I sat back in my computer chair and started rubbing my insistent shaft, I couldn't help but smile as more and more of the guys in the room started to tune into my cam. I slowly teased myself while the various instant messages popped up telling me how cute I looked, and how much people liked my hose or my panties or both. I don't know how much you can believe horny men, but it still boosted my ego quite a bit.

As I got close to orgasm, I grabbed some tissue to catch the mess. Normally I try to catch it in my hand so I can show it to the cam, but I was trying NOT to make a mess tonight. As I dropped a large load of cum into the tissue I was flooded with request to see me eat it. I'd never done that before, and wasn't about to do it out of a Kleenex. But a large glob landed on the back of my hand, and I figured why not. Get into the spirit of the outfit. I leaned forward and licked the slimy mess off the back of my hand, much to the enjoyment of my watchers.

Then I stood up, cleaned off my rapidly deflating dick with a fresh tissue and tucked the whole package between my legs, quickly pulling up my panties. I had yet to swallow the cum I licked up as I was trying to decide if I liked it or not. As I swirled the sticky solution around my mouth, I decided that I didn't mind it, but that I wasn't about to become some glory hole slut. I was far from addicted to it.

I quickly logged off Yahoo and finished getting ready. I pulled on a pair of nylon running pants, which felt awesome over the fishnets, and a pair of running shoes. I threw on a t-shirt, and grabbed up the garment bag with my costume. As ready as I could be, I headed out the door.

Chapter Two: Setting Up Before I finished out the costume, I helped the host set up for the party. Linda and her husband Steve always set up a nice spread for the annual party. Steve was on assignment across the country, so I offered to come in early and help Linda set up. I conned Donna into coming over early to help, so there would be plenty of time for my makeover later.

Linda teased me about serving drinks all night long, and I laughed and said sure. After all, it would fit in with the character I was trying to create. In no time at all we had the place looking sharp, and I headed up to the guest bedroom to get ready. About the time I got down to just the fishnets, garter and panties, Linda and Donna came into the room. I froze, embarrassed and afraid of their reaction.

"You look great!" Donna exclaimed. "I wish my legs looked as good in fishnets as yours!" I knew she was just trying to give me some extra confidence because Donna is one hot lady. She easily has the best legs in town.

"You lair. You've got awesome legs, but thanks." I said. It made me smile.

"We'll, I'm jealous." Linda said. "They do look good. I can't wait to see them in heels."

"Yea, let's see the shoes!" Donna ordered. I reached into my bag and pulled out the three-inch heels I intended to wear. "Oh no, you can't do that." Donna said. "Those are open toed. We'll have to paint your toenails."

"I've got the perfect color!" Linda yelled as she dashed out of the room. I started unclipping my garters and rolling down the fishnets. About the time I got the first one off, Linda returned with a bottle of nail polish. Vivid Red it was called, and it was so bright and shinny it was almost blinding.

"I'm not sure about that..." I tried to say, but Donna screamed, "It's perfect." The next thing I new Donna was kneeling on the floor applying the polish to my unclad toes. I rolled the hose back on my leg, clearly loving the feeling. I must have moaned, because Linda and Donna started giggling.

"I think he likes wearing this stuff." Donna smirked.

"Yea, imagine that. He loves wearing the stuff we hate." Linda giggled.

"Speak for yourself girl, I love dressing sexy." Donna laughed.

"Yea, but you're crazy."

I must have blushed seventeen shades of red. That sent the girls into another round of giggles. I was starting to feel pretty embarrassed.

"We won't tell anyone your secret," Linda told me. "Now, let's get that other foot done."

I let them pull the other hose off and paint my remaining toes. Even with the hose back on, you could clearly see the bright red polish. I slipped into my heels, and had to admit that it looked better than without the polish. I teetered around on the heels for a few minutes before I got the feel of them. Once I did, I noticed that Linda and Donna were staring at me. "What?" I asked.

"You got used to those shoes awfully quick," Donna said.

"There is no way this is your first time on heels," Linda agreed.

I didn't know what to say. I'd been caught. I just stood there and blushed.

"You like dressing up, don't you." Donna stared right at me. I could only nod. "How long have you been doing this?"

"I don't know. Forever, I guess. Since I was a kid."

"Who else knows?"

"Nobody..."

Linda walked over and hugged me. "Don't worry, we won't tell anyone. It can be our secret until you decide to let people know. I won't even tell Steve." I smiled and hugged Linda back.

Donna joined in a group hug and said, "I'll keep your secret, as long as you let me dress you up now and again."

"Anytime," I said, and gave her a kiss on the cheek.

Linda pushed us away, "No fair, I want to play dress up too!"

Donna and I just giggled. "You can play too," I promised.

"We'll, we need to get YOU dressed up before the guests arrive. I want my maid to look pretty for the party," Linda announced. "I think I'm going to like having a maid!"

"Oh no, now I'm in trouble." I reached into my bag and pulled out the petticoats I'd bought for the costume. They were very full, and a little hard to get into. Linda and Donna helped, and soon my cute panties were buried under the fluffy material. Following the petticoats was a black strapless chincer with a built in bra. Into the cups of the bra section went two breast forms. Over it all went the little black maid's uniform, very tight in the bust and flaring at the hips. It was heavy and long enough to take weigh down the petticoats a bit, falling about half way down my thigh.

"If you bend over to much, you'll be showing your panties!" Linda said. "You're going to drive the guys crazy!" I blushed at that. Then the doorbell rang. "Well, damn. My guests are arriving and my maid isn't ready. You two finish up and join the party, I'll go get the door." And with that, Linda left.

Donna giggles, and pulled out her makeup kit. "Let's get to work." She started in on me, and in just a few minutes had turned my softly masculine face into a stylish, but somewhat slutty, feminine one. I had to admit that her skill with a brush was better than my previous fumbling with make-up.

"You're going to have to teach me how you did that," I said. Donna just smiled.

"Okay, you're going to have to finish up on your own, I need to get ready too." Donna said as she shooed me away from the mirror. I went over to the bed and pulled out the little white apron and the little white hat. One I had them on, I asked Donna to check me over before I headed out. She was half way through putting on her vampire makeup.

"You look good, but let me do something, okay? Don't freak." She reached up underneath my petticoats and ran her hand over my crotch. "I thought so," she said. She reached into my panties, and grabbed my quickly growing cock out from between my legs and let it loose inside the panties. "That'll be more comfortable, and your petticoats will hide any excitement you may experience." She giggled.

I was stunned. I'd been out with Donna several times, but we became friends and had never done more than kiss before. She'd been seeing Charlie for several weeks now, so this was totally unexpected. When I didn't turn and leave, she ran her hand back under my petticoats and wrapped her hand around my silk encased hard on. "See, I couldn't tell by looking that you were tenting out those panties. Now, go downstairs and have some fun."

Chapter Three: The Party Still slightly stunned, but ready to have some fun, I headed downstairs. Several couples were already in the party area, and I stopped long enough to say hi. Linda quickly waved me over. "I've got to get ready," she said, "you answer the door and keep the drinks flowing." With that, Linda bolted up the stairs.

The doorbell rang again, and I strutted over to the door. Several of the women let out catcalls as I walked across the room. I opened the door to find Charlie waiting. I smiled as he entered. He just kept staring at me. "Wow. I can't believe it's you." I smiled back. "Donna is upstairs getting ready. She should be down in just a second. Do you want a drink?" Charlie just nodded, his devil horns bumping the doorframe.

I walked back into the party, leading Charlie to the drink table. In my worst French accent I asked, "Wine, mon-sure?" Charlie just smiled and nodded again. I poured him a glass of the house's best boxed red, and handed the plastic cup over to him. I also took a second to check out his costume. Red long johns with a red pair of briefs over them, red face paint, red gloves and plastic horns on his head; a decent devil.

Charlie spotted a couple he knew and wondered over. She was dressed like Morticia Adams and he was done up like a gangster. I was watching Charlie walk when I heard the doorbell again. I walked to the door and found a set of three policemen handcuffed to three hookers. The girls looked like real sluts, two in short skirts and one just in modest but sexy lingerie.

Shortly after the hooker patrol arrived, Linda came back down in a pretty princess outfit. She glided over to me and thanked me for taking over, then ordered me to enjoy myself. I marched over to the table and got me a Jack Daniel's Hard Cola and found a perch. Charlie came over and sat on the sofa next to me. "You really do look convincing. I think some of the guys haven't recognized you yet."

"Well, you just keep your mouth shut then, so far they are all coupled up and don't need to know I'm anything they wouldn't be interested in." I laughed.

"Well, maybe I can keep quiet, for a price..."

"Charlie, are you flirting with me?"

"Maybe."

"Well, he better not be flirting with you too much, that's my job." I looked up to see Donna standing over us. She looked fantastic in a short black latex dress that left little to the imagination. The dress was so short her garters showed when she was standing, clipped to sexy seamed black hose. Six-inch high heels in come fuck me red made her legs look good enough to eat. The neckline on the dress plunged to her navel, showing plenty of her nice, firm breasts. And she sported a pair of mean looking fangs.

Donna sat down on Charlie's lap, kicking her legs up into mine. The dress rode up, clearly showing her red panties to anyone who wanted to look no matter how modest she tried to sit. She gave Charlie a big kiss.

We sat around chatting while more guests arrived. I remember seeing a Bettlejuice, several other vampires, another devil or two and plenty of police and firefighters. Sluts were out in force, and plenty of leg was shown. As the crowd grew, so did the flow of drinks. Before long, I was feeling little pain and Linda was starting up the music for dancing.

Donna and her red panties jumped up and pulled Charlie out onto the dance floor. That seemed to be the cue for everyone else to start dancing. Before the crowd hit the floor, I couldn't help but notice that Charlie was sporting major wood. Seems he enjoyed the scantily clad Donna squirming on his lap. He didn't bother hiding it, not that he had anywhere to hide that monster. He started rubbing it against Donna, who didn't seem to mind. Now I had a clear view of Donna's panties for the last half hour, so I was sporting a woody myself. Of course you couldn't see mine, thanks to the petticoats.

The floor was quickly crowded, and since I didn't have a date, I headed out to the kitchen to see if Linda needs a hand. Linda was busy plating up some more snacks. I jumped in to help, and the two of us quickly got the snacks out to the hungry dancers. As we returned to the kitchen, Linda gave me a hug to thank me for helping. She held on a little longer than I thought she would, and I felt something moving my petticoats. Suddenly I felt Linda's hand on my hard on. I was shocked, but it felt so good I didn't move.

"Donna told me you had a snake hiding in your petticoats. I had to check for myself." She gave me a brief kiss. "You really look good. I'll have to dress you up for Steve when he gets back. Maybe that will convince him to give girls clothes a try."

I was shocked. "You want Steve in girls clothes?"

"Yes, it's always been a fantasy of mine. You've got this princess really turned on, so let's go dance in public where I'll have to behave." Linda led me out to the dance floor where we danced close, but safe. Occasionally she'd turn around and rub her ass against my hidden shaft, driving me crazy. We were getting lots of looks, two girls dancing seductively on the dance floor.

Before long, Charlie and Donna danced over to us. Donna leaned in and asked Linda if she knew what she was doing. Linda blushed and said, "Yea. I'm leaving him with you two before I make a mistake. I'll be back later." Linda headed to the back of the room and up the stairs.

I felt awful, but I didn't know why. I wanted to apologize to Linda; I didn't mean to let it go as far as I had. Donna must have read my mind, because she stopped me. "Don't follow her. She's fine. She just needs to go relieve the tension. She'll be back after she calms down. You really are hot all dolled up like that. I don't think Linda will want to dress you up. I don't think she could keep her hands off you."

I blushed, and Donna pulled me into the dancing with her and Charlie. We made a Donna sandwich, and started to really bump and grind. I kept fetching us all drinks as we danced and partied and frankly I don't remember a good part of the evening. When I started remembering again, I found Donna rubbing up against my front, and Charlie rubbing up against my back.

This is odd, I thought. I could clearly feel Charlie's very erect cock rubbing under my petticoats and across my panty clad ass. Be it drink or a night of arousal from my sexy clothes, I'm not sure. But the result is that I didn't mind. Having Donna rubbing her red panties against my petticoats didn't help me decided. I was so horny I almost made a mess in my new panties.

I decided a scene where I pushed Charlie away was less desirable than the rather pleasant feelings his rubbing caused, so be it drink or lust I decided to go along for now. Donna was all but impaling herself on my hardly hidden erection, pushing me with great force back into her boyfriend. I became an almost passive member of their dry hump festival.

As time and a little sense returned to me, I looked out from my enjoyable position to see that the tree of us were among the last to leave. Batman lay passed out on the couch. Fat Albert was munching at the remains of the snacks. Our princess hostess was nowhere to be seen, but odd splashing noises in the direction of the kitchen hinted at a possible random act of dishwashing.

At this point my fear and concern got the better of me and I pulled out from the two lovebirds. It was with a bit of regret that I felt my petticoats return to cover my bottom. I noticed that the tent in Charlie's briefs had grown to a monster, and the latex skirt on Donna's dress didn't fold back down, leaving her red panties open to the world.

"Come on sweetie, we were having fun." Donna purred. "I could tell by your petticoated pole that you were having a good time!"

"I'm sorry. Reality just hit me. I think I better go." I stammered, and headed for the stairs. I dashed to the bedroom I'd changed in, hoping to throw of the costume, get into guy clothes and go home. Maybe watch some football or something. I felt a strong urge to do something manly.

I hadn't locked the door, and I heard Donna come into the room before I'd managed to get off a single stitch of clothing. Close behind here was Charlie, who closed the door and locked it.

"Come on sweetness. Let's climb onto this bed and talk for a while. All private and safe. No one can see what we do. You can trust Charlie and me."

Not really knowing what to do, I let myself be led to the bed. I was placed in the center of the bed, and Charlie and Donna took opposite sides.

"You look so good in your uniform. Charlie can't believe how good you look. I can't wait to dress you up some more!"

This just caused me to blush a deeper red than my shiny toenails.

"She's right, you do look fantastic. And your ass felt great on my cock."

And here I thought I couldn't turn any redder.

Donna slipped her hand under my petticoats and rubbed the front of my panties. I grew another inch. She grabbed my hand and guided it to her own panties, and slipped it inside the waistband. I wasted no time digging a finger into her snatch, fingering her with a passion. She was more than just wet, and the moans she made told me she liked what I was doing.

Not wanting to be left out, Charlie guided my hand to his crotch, where I could barely wrap my fingers around his massive cock. Embarrassed but excited, I moved my hand along his monster, rubbing the cotton briefs along his shaft. As I did, the head of his cock started to work its way through the fly and out into the open. Before long, I was running my bare hand along his naked staff.

I nervously looked over at his dick, erect and encased by my own hand. I marveled at how different it felt from my own. I wondered if he felt the same pleasing sensations that Donna's hand was sending into me. One look at his face told me I must have been doing something right.

About then, Donna reached under a leg band and started pulling out my own hard on. Before I knew what was happening, she had it deep in her mouth, sucking on it hard. At first my eyes rolled back into my head as the waves of pleasure her probing tongue sent through me blocked out all my other senses. The feeling of her lips and mouth and throat on my staff felt better than any blowjob I'd had before.

When enough capacity for thought returned, I looked over at Charlie to see if he was okay with this. About that time, Charlie leaned forward and kissed me full on the lips, pressing his tongue against my teeth. Donna took that moment in time to run her fingernails across my balls and toward my virgin boy-cunt. As I gasped, Charlie probed my mouth with his tongue. I melted into the kiss, and coupled with the warm, wet, wonderful feeling of Donna's magic mouth, I was afraid I was about to cum.

Donna pulled her mouth off my cock, and I thought I might die. She moved up on the bed, and replaced Charlie's tongue with her own. I could faintly taste that same sensation from earlier when I licked my own cum from the back of my hand. Somehow, tasting it on her made it taste better.

"Isn't this exciting?" Donna moaned in my mouth. If I had the ability of speech, I would have told her yes, but that ability fled me as Charlie grabbed my dick and started giving it a vigorous shake. Donna pushed Charlie away, and then laid across my lap and started blowing her boyfriend. I couldn't help but watch as Donna made that monster cock disappear into her mouth.

I started to lean over, thinking I'd get a better view. Charlie must have misunderstood because he grabbed the back of my head and pushed me down onto his stomach. I was now just inches away from Donna's mouth and Charlie's cock.

Donna's eyes smiled at me, and she pulled me closer. She pulled Charlie's monster almost completely out of her mouth, leaving only the head inside on her tongue. She pulled me close and kissed me, without taking Charlie out of her mouth. For the first time ever, and one more time than I ever thought possible, my lips were against another man's cock.

Donna used her tongue to slide the head out of her mouth and into mine. Charlie had a death grip on the back of my neck, so I had no choice but to keep it there. I didn't really know what to do, so I started moving my tongue around the head. I found a spot that made Charlie moan and loosen his grip, and concentrated on that.

Keeping a gentle pressure on my neck, Charlie started to slowly push down, forcing more of his shaft into my mouth. I relaxed as best I could and let it slide in until it hit the back of my throat. When I started gagging, Charlie pulled out and then slid back in, slowly fucking my mouth. It wasn't unpleasant, but it wasn't fun either.

Donna moved to the far side of the bed, allowing me to get into a much more comfortable position on my knees. Donna climbed between my legs and I soon felt her warm mouth encase my own desperate cock. As the feelings of pleasure washed over me, my mouth began to relax. I moved more easily on Charlie's monster shaft, and suddenly I understood the pleasure of giving head, as well as the pleasure receiving it.

Charlie felt the difference as well. With a loud moan, he removed his hand from my neck. It didn't need to be there anymore, my mouth wasn't about to leave his cock. I moved my tongue and lips around that massive staff, worshiping the veins along the underside, kissing the mushroom softness of the head, and tickling the tender spot at the bottom where dick meets balls.

I was in heaven. This is what wearing women's clothes had always meant to me. The sexual release was amazing, and I dived into my newfound joy of sucking on Charlie. From my groin I could feel and hear the delicious sound of my dick deep in Donna's mouth. Charlie was getting close to release, and my own explosion was rapidly approaching. Somehow Donna knew this, and pulled my cock out of her mouth. She moved up on the bed, and pulled me off of Charlie's as well.

"Not now sweetie. Maybe some other time. Right now, I need some attention, and I have an idea I think you'll both like."

Donna told me to stretch out on the bed. She pushed my petticoats up around my waist, and climbed onto my shaft. Her back to me, she impaled her ass on my cock, using her own spit as lube. Donna was no stranger to anal sex; I slid in until her cheeks rested on my groin. Then she laid back, across my chest. Charlie climbed between our legs, and I could feel him enter Donna's sopping wet cunt. I could feel the friction as he started pounding into her. I could feel his balls slapping against my own with each thrust.

The force of Charlie's thrusts moved Donna along my own shaft, and the overall scene had me close to the edge. Donna's moans and near screams were pushing me over into oblivion. Multiple orgasms started rippling through Donna's body as the two cocks pistoned into her. With a scream, she grabbed Charlie and held him still, deep inside.

The stimulation reduced, Charlie and I didn't quite cum. We were close, so close, but not there. Donna caught her breath for a moment, letting Charlie's cock stay deep, his balls resting against my own. I could feel Donna's cunt juice running over my balls and onto the bed. I was so close, sitting on the edge wanting to go over.

Donna pushed Charlie up, having him kneel on the end of the bed. She pulled herself off my cock, nearly causing me to cum right then. She quickly stuffed Charlie's dick back in her mouth and began jacking him off with her hand. She had barely started when Charlie went ridged and started blowing his spunk into her hot mouth. As soon as she had gathered the last drop in her mouth, she spun and dove onto mine. I don't think I lasted as long as Charlie, emptying my load in her mouth in what felt like microseconds.

She climb up on me, and planted her lips over mine. As she forced her tongue into my mouth she feed me the double load of cum. Our tongues danced in the mixture for what felt like hours, then she sucked about half of the spooge back into her mouth, and broke off the kiss. She turned to Charlie and feed him the same way. It was hot watching the two of them kiss; with cum leaking down both of their chins and onto her much abused latex dress.

When they finished the sticky kiss, Donna looked over at me and smiled. "Amazing." Was all she said. The alcohol and the post sex groggies were quickly taking their toll. It was clear we weren't going home that night, so without another word, we got out of the bed and started stripping down. At Charlie's request, Donna and I kept on our bras, panties, garters and hose. Charlie slept in his red briefs. We cuddled up in the bed, Charlie on one side of me and Donna on the other.

We slept the sleep of the sexually satisfied.

(Maybe more, if you liked this story.)

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