Holiday Ch. 01

Sorry, I wanted to get it out for Halloween so it's a little rushed.

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Halloween is one of my favorite holidays; Trish, my wife, and I always get invited to the best parties.

"Honey, I'm home!" shouted Trish, my wife.

It was Friday and I just got home from work myself.

"What did you buy?" I asked as I walked into the living room.

"My boss is throwing a Halloween Party and I stopped by and got us some clothes to put our costumes together," she said as she put the bags down on the living room couch.

"We made plans to attend Paul's party..." I began.

"I know but my boss basically insisted that we all attend... besides...you know I'm bucking for that new management position," she explained.

"But I promised..." I started.

"I always tag along with you to your friends parties," she said.

"You always seem to enjoy yourself,"

"I do but this is important to me, to us, come on," she pouted.

"Fine..." I began.

"Great!" she exclaimed.

"What am I this Halloween?" I asked in my usually enthusiastic manner.

"Pocahontas!" she said excitedly.

"What?" I exclaimed laughing.

"Pocahontas...something's wrong?" She inquired.

"You want me to be Pocahontas?" I asked.

"Are you seriously asking me that?" she asked upset.

"I'm not going to be Pocahontas,"

"Really, how many times did I have to go as your side kick?"

"Come on!"

"No, you come on!"

"Trish..."

"We were Bonnie and Clyde, Sonny and Cher, Scarlett O'Hara and Rhett Butler, Laurel and Hardy, Dr Jekyll and Mr Hyde, and Beavis and Butthead. I don't think asking you to be Pocahontas is too much to ask," she remarked sarcastically.

"Why don't you be Pocahontas?" I asked.

"Because I'm a 60's Air Line Stewardess!" she answered.

"But we agreed..."

"No, I didn't have a choice...everybody had to pick their characters out of a bowl. Yours came up Pocahontas; live with it because they'll be checking us in at the door," she clarified.

"Wasn't there a male and a female bowl?"

"No,"

"You're not kidding?"

"No,"

"Really?"

"If you're not Pocahontas the only pussy you'll be getting is from our cat," she said nastily.

"Fine,"

"Thanks!"

"I figure if you can be Hardy, Hyde, and Butthead I can be Pocahontas for one night," I told her.

"Here's your costume," she said pulling it out of the bag.

It was a goldish dress that probably reached to mid-thigh. The dress had blue trim from shoulder to waist and had tan fringes around the bottom; it also had a brown string belt and high calf brown moccasin boots. To top it all off she pulled out a black wig with a brown headband and red arm band.

"Go try it on!" she said excitedly.

"I'll try it on here," I started undressing.

She laughed.

I took the dress.

"Wait, all your clothes,"

"Why?"

"Didn't you make me wear briefs playing those characters?"

"Yes but..."

"Then you have to wear panties and learn to tuck your penis and balls to play Pocahontas," she said pulling out panties, a gaff, and a cd from one of the bags that were labeled Girly Boys.

"What's this?"

"Panties, a gaff, and a cd to teach you how to tuck your junk correctly, so get to it Pocahontas or get use to a different type of pussy," she enlightened me.

I had a feeling she wasn't kidding, she placed everything back in the bag and handed it to me.

"Oh!" she exclaimed, "don't forget these."

She handed me a set of fake boobs.

"Breasts, they slide into the pockets on the inside the dress, I'm sure you'll find where they go,"

I was off to the computer; I practiced until I was finally able to push my balls into my sacks, tuck, and slide on the panties. I put on my costume and went to Trish.

"Awesome...you look just like her! Now take this cd and learn how to talk like a female, range and intonation,"

"And what if I can't?"

"Get use to a furry pussy that actually purrs; if you know what I mean?"

I knew what she meant; I took the cd, grabbed a couple of ice coffees, and went back to my computer. I spent all night on voice training until I felt confident in myself. I looked at my watch; it was two in the morning so I hit

the sack.

"Good morning sleepy head," Trish said as she shook me awake.

"What?"

"If you're sleeping you must have nailed the female voice,"

"Yeah,"

"Show me!" she said excitedly.

I cleared my voice.

"I'm waiting,"

I sat up and grabbed the bottle of water from my nightstand,

"Well,"

"You're very impatient," I said in my best voice.

"Not bad!" she exclaimed.

"Was it really that important for me to speak female?"

"You made me speak male didn't you?"

"Touché," I remarked.

"You know, I think I'll take back my outfit and head down to the Antique Clothing Store to see if they have a genuine 60's Air Line Stewardess. In fact, get in costume, you're coming with me," she told me.

"Wait a minute..."

"What's wrong; we usually spend time together on Saturday?"

"It's just...I mean..."

"Yes,"

"Do I really need to be in costume?"

"I didn't complain when I had to..."

"Touché once more," I said as I took a quick shower and got in my costume,"

"You really look good as Pocahontas; did you shave?" she told me as I approached her at her vanity.

"My whole body; I didn't want to get any funny looks,"

"Bend down and pucker up," she said.

I did as she asked.

"Close your eyes,"

I did.

"Hold that pose," she said as she put lipstick on me.

"Why did you do that?" I asked opening my eyes.

"Look in the mirror," she smiled.

I turned my head back and forth; I looked good.

"Sit," she said as she got out of her chair.

I sat as she plucked my eyebrows and applied makeup.

"Now look in the mirror,"

"I look like a girl,"

"Okay Pocahontas it's my turn,"

I got up feeling good about Halloween and my costume.

She finished her makeup, got dressed, and we left for the store.

We entered the mall and went to the store to take back some of the items she bought for her costume.

"Hello," smiled the woman at the returns desk.

"Hi," my wife replied with a smile.

"Anything wrong with any of these items?" she asked.

"No, just decided to do something different,"

"I love your costume; Pocahontas?" she asked me.

Trish looked at me waiting for me to reply back.

"Yes," I answered in my best female voice.

Trish smiled; I passed.

"Perfect," she said as we left the returns desk.

"Thanks...I think,"

She walked directly to the frozen yogurt and ordered a pint of double chocolate fudge then looked at me.

"I'll have a pint of your banana strawberry please," I told the girl at the counter.

Our order was quick and we sat at one of the tables at the center of the mall to enjoy our treats.

"Beware, the vultures are coming," Trish spoke softly.

"Hi, my name is Josh; my friend here is Michael," Josh introduced with a smile.

They approached from behind me; I was shocked when they suddenly appeared.

"Hi," Trish replied as I looked on.

"We were wondering if we can buy you lovely ladies drinks later at Knock Outs,"

"That's very tempting but my husband may not like the idea of me going out with two hot studs for drinks and mischief," Trish told them then flashed her ring at them.

"Pocahontas; buy you a few drinks tonight? Michael inquired.

"Sorry, I'm into girls only," I replied.

"It's been a pleasure; enjoy your ice cream," Michael said as he nodded and walked off with Josh.

"Thank you," we said in unison.

"That went well," I said.

"I think Michael liked you," Trish whispered.

"He was cute but like I said I'm into girls only,"

"Are you sure about that?" she asked.

"Why wouldn't I be?"

"You are dressed like a girl," she laughed.

"You might have a point there,"

"You could have said no,"

"Are YOU sure about that?" I emphasized.

"Yes,"

"I didn't want to sleep with the cat, besides, it isn't a big deal; it's a Halloween costume,"

"I guess so," she said as we giggled.

"It is!"

"I forgot to mention my boss is giving twenty-five thousand to the best "believable" character so keep doing what you're doing and you'll win,"

"We really don't need the money but..."

"Do it for me or..."

"...I'll be sleeping with the cat,"

"Exactly, are you ready to move on to the antique store?"

"Sure,"

We head to the antique shop to try to find a 60s Air Line Stewardess Outfit for Trish. Once there a lady greets us as we walk in.

"Hello, May I help you?" she asks sternly with a smile.

"Yes, I'm looking for an Air Line Stewardess Outfit from the 60s," Trish responded.

"Yes, this way," the lady announced.

"Great!" Trish exclaimed excitedly as we followed her to a rack.

The sales woman pulled out a medium blue outfit.

"It's perfect!" Trish exclaimed.

"I believe this is your size; the changing room is right behind you," the sales woman pitched.

Trish returned dressed in the uniform.

"Wow, you look great!" I exclaimed.

"I think so too!"

Again, it was medium blue, the skirt reached to the bottom of her knees, the jacket flared around her hips and the sleeves came to mid forearm, the jacket had large lapels as did the blouse that folded over the jacket. The outfit came with a matching hat, white gloves, blue two inch heel shoes, and a gold winged pin.

The sales woman returned.

"How much is everything?" my wife asked the sales woman.

"Seventy-five hundred dollars," she answered.

"Wow, why so much?"

"It's brand new; it's never been worn," the sales woman replied.

"I'll take it," Trish said.

"Fine, I'll wrap it up once you change; is there anything else I can help you with?"

"No, I'll be right back,"

They went their separate ways while I looked around.

"Find anything you like?" Trish asked.

"Just looking,"

"I mean while we're here..."

"No I'm fine," I said now realizing I was still on the woman's side of the store.

We made small talk on the way home.

"Are you hungry," I asked once we got inside.

"Yes, but first get out of your costume before you get it dirty,"

"Damn, I forgot I was wearing it,"

"Use your girly voice so you won't forget at the party,"

"You're right,"

"Oh, and you better wear your gaff and panties too so you don't forget how they feel; we wouldn't want you grabbing yourself all night,"

"Good idea,"

"Feel free to use my panties since they fit you but only with the gaff,"

"Okay,"

I went and changed to shorts and a t-shirt keeping my gaff and panties in place. Every day it was the same thing; girls voice only, and gaff and panties at all times. I even took the week off and wore my costume around the house so I would feel comfortable wearing it.

The week went by quickly.

"You ready," Trish called out.

"Are you going to do my makeup?" I asked.

"Sorry, I forgot, come here and I'll do it for you,"

"Coming," I rushed to her and she quickly did my face then we rushed out.

Again, we made small talk in the car. We pulled into his driveway to a huge house.

"Damn Trish, this has to be twenty thousand square feet or more,"

She rolled down the window and gave the security officer her invitation.

"Pull straight ahead," the officer said.

We pulled straight ahead; two gentlemen on either side of the car opened our doors for us.

Trish seemed eager as she rushed us inside. Her boss, Mr Hutchinson, met us at the door.

"Trish, glad you could make it," he said kissing her on her cheek.

"Thanks," she said.

"60s stewardess,"

"Yes,"

"Nicely played Trish,"

"Thanks,"

Flirting...

I'm just being jealous.

"And whose the lovely lady you brought with you," He asked.

"Pocahontas," she replied quickly.

"Nice to meet you Pocahontas," he said kissing my on my cheeks.

"Thank you," I said in my best girly voice.

"Go mingle and have some drinks," he told us.

"Thanks," we answered in unison.

"I'm sorry, I have to run to the restroom, can you manage by yourself?"

"Of course," I answered grabbing a drink from a maid passing by.

I met a lot of people as time passed and was having a lot of fun as Pocahontas. I got with a group of outrageously gorgeous women and learned what it was like to be on the other side of the fence. Guys pampered us by bringing us drinks; in fact, I was pretty wasted along with my new found girlfriends.

Trish finally showed up.

"Hey Trish,"

"Sorry, there must be at least two-hundred people here and half of them wanted to talk to me,"

"That's okay, I understand,"

"Thanks, you look pretty wasted, are you okay?"

"Yes,"

"Hey, let's go get high again," Millie, one of the girls in my group said.

"Trish?"

"No thanks, you go ahead; Mr Hutchinson wanted to talk to me about a problem at work,"

"Are you sure, it's the only night we allow ourselves to get stoned,"

"Excuse me; may I steal Trish for a little while?" Mr Hutchinson asked.

He was a good looking guy, early thirties, black hair, blue eyes, and rich. I was jealous but what could I do?

"Sure, just bring her back she's my ride home,"

"See you later," Trish said as she left with Mr Adonis.

"Are we getting high or what?"

"Sure," I answered.

She took my hand and led me outside toward the one of the three pool houses where we smoked a joint earlier.

"I'm wasted," I admitted to Millie.

"I'll take care of you," she said as she light up a bowl which we finished.

"I'm totally wasted Millie," I confessed.

"Really," she said as she kissed me.

"I'm married,"

She slides her hands behind my back and cuffed my wrists...then pushed me onto the bed. I instantly became disoriented staring up at the ceiling.

"You're cute," she told me as she mounted me and kissed me.

She lifted my dress around my breasts and figured out they weren't real; she reached between my legs. Millie slid off my body and reached between my legs and giggled. She kissed me again as she released my cock and fondled it.

"Millie," I said as she pulled away.

"Yes,"

I lost my mind and just giggled.

Mary and Jane from the same group walked into the room.

"Wow, what are you guys smoking in here?"

It seemed as though I couldn't speak so I watched as Mary and Jane stripped to their panties. I raised my head to see Millie had pushed my dress up, removed my panties and gaff and was sucking my dick. When I turned back Mary was on one side of the bed and Jane was on the other. One then the other pushed their nipples into my mouth so I could suck them.

Time passed as I came in Millie's mouth.

"Mmm," she said as she raised her head and slid up my body.

She kissed me as I tasted my salty jizz slide down my throat as I swallowed unintentionally.

"It's time,"

Mary and Jane both reacted and raised my legs up and over my chest. Millie started sucking my dick again and inserted a finger into my ass.

"Mill..."

Mary kissed me; then Jane. They confused me.

"Mar...Jane,"

Then I felt it; something penetrating my ass.

Millie mounted me once more and was fucking me with a strap-on. I was so fucked up I couldn't even bring my legs down so I closed my eyes and enjoyed the sensation, moaning, until she withdrew.

"Mary," Millie said.

I opened my eyes to find Mary between my legs as I felt her penetrate me.

"Ah...ah...ah...I moaned with her strokes as the sensation mounted.

Millie kissed me...then Jane kissed me. Millie turned my head her way again and pushed a cock in to my mouth. I played along and sucked her strap-on as Mary continued fucking me.

"Jane," Mary said.

They switched places, I felt Jane enter me; I moaned as Jane fucked me harder and faster than Millie and Mary did.

"Ah...mmm...ah...ah...I continued as Jane fucked me.

Suddenly I felt a warm sensation in my mouth and heard Millie moaning.

Mary turned my head toward her and again I took a cock in my mouth.

"Ah," I continued as Jane planted the strap-on deep inside of me and moaned loudly.

Again I felt a warm sensation in my mouth.

Mary pulled out as Millie kissed me passionately.

I swallowed feverishly as her tongue attacked my mouth.

"Thanks sweetie," Millie said as she planted another kiss on my lips.

Millie and Mary released my legs; I was too spent to move from the drinking, smoking, fucking, and sucking.

Millie and Mary stood and I saw that neither one was wearing a strap-on but had real cocks, shaven cocks to be precise.

"Thanks," Mary said as she kissed me.

"Thanks," Jane said as she came around and kissed me.

They were transsexuals...

I didn't know...

I couldn't...

They looked and acted like women.

Did I really care?

No, I was too wasted to care.

I definitely wasn't going to tell Trish about my encounter. She would be pissed...maybe she would think I planned this...and maybe retaliate with an encounter of her own.

"Pocahontas, we'll have to do this again, I'll call you," Millie said as they all left.

I was spent and fell asleep.

When I awoke my head was clearer, my cuffs were off, and my gaff and panties were in place.

I got up to find the party was in full swing. I just hoped Trish wouldn't find out.

"Hey, what's up?" Trish asked me.

"Trish,"

"What's wrong?"

"Nothing,"

"You're acting awfully suspicious,"

I laughed.

"Are you ready to go?"

"What time is it?"

"Two am,"

"Wow, what were you doing all night?"

"The same as you...

Oh shit!

"...talking, drinking and having a good time," she answered.

"This is the first Halloween or holiday we haven't spent together," I said.

"Well, I couldn't find you,"

"Yeah, my girlfriends and I were walking the grounds getting stoned out of our mind," I lied.

"Yeah, I got tied up with my boss so it was really uneventful but I did find time to mingle and drink some,"

"Let's go home," I said.

"I'm ready,"

We said our thank you and goodbye to Mr Hutchinson and left. Still, I felt something between those two... but...it's probably just jealousy.

Once home I asked, "Are we going to have our traditional spooky sexcapades?"

"I'm sorry but I'm really tired," she said as she kissed me and landed in the shower.

"That's strange, she always initiates sex on holidays. I guess it's for the best because I would need a shower before she smelled sex on me," I whispered to myself.

I made my way to another shower in the house and got in bed. I tried to hug her but she turned away.

Interesting!