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Telling Mom I'm A Cross Dresser part 18: Missy's Halloween Party

Part 18 is about halloween. Hope you all enjoy despite i was a little rushed for this one.


I had enjoyed my week of sex with Thomas and Lemar but in the end it left me sore and used but not like I was complaining. It was now getting close to Halloween and mom and I were making plans to go to a Halloween party a few city blocks away from us. Yeah, sounds kind of boring I know but it was no ordinary party with costumes and drinking alone. It was an orgy for bisexual people.

It was only a few days away and Mom and I decided to go costume shopping both online and in the local stores to see if we could find something sexy and still be mysterious so people wouldn’t know who we were and add to the excitement.

The day of the party came and we were getting ready to leave soon. Of course we began with our normal ritual of shaving and applying makeup. The costume I picked out was a lingerie model and wore a Extravagantly embellished one piece teddy. Honestly it seemed kind of slutty even for me as it had only enough to cover my nipples and goes down into a thong that looks simply like a band that goes from my belly button to between my legs. Then up to a lace band that went just above my hips and all the way around and back to the front again. One last lace band went just under my tits and around my body as well to meet the straps over my shoulders. The part I thought was the cutest was how it had bows that were on my crotch, just above my ass and on each of my nipples. The thing that had me the most nervous was how my cock fit just perfectly fit in the strap but was still worried on if it would come out or not. I finished with my wig and my heels before my “costume” was complete.

Mom’s costume that I picked out for her was like a sexy leopard cat girl costume. It had the cute cat ear head band and long leopard print gloves and stockings that fit nicely to her skin. The last thing I got out for her was a sexy piece of lingerie that was black and see through but had a leopard print going all the way up the front and cupping her big tits nicely into sex appeal that no one could resist. The final touches were a kinky leopard’s tail butt plug that fit into the hole of her booty shorts that matched the rest of her outfit.

When I saw mom in her costume I thought I might have some competition as her outfit would easily attract a lot of attention but then again what I was wearing would catch a few eyes as well.

Just as we were we hopped in the car and drove to the party. I looked in the back to find there were two duffel bags. I asked mom what they were and she said they were extra costumes she picked out for half way through the night. I wanted to ask but I thought it would be more fun to just let it stay a surprise when the time was right. When we finally got there, I looked around and saw a lot of couples walking to the house. Some were dressed in slutty costumes like us and lots of different kinds of couples together from straight and interracial to homosexual and groups.

At first I was nervous to go in dressed like I was but after seeing the couples together I started to think there was more to this party then mom was telling me.

“Yep you guessed it sweetie, this is an orgy and we are going to have some fun tonight!” she said with a cheer and delight in her tone.

I have to admit that I got a little excited to but tried to contain it as we got out of the car and made our way inside. We got to the door and mom knocked on it. A man opened the door in a Tarzan costume wearing nothing but a loin cloth over his cock. He was very well built with big muscles and about six foot tall. He had short dark hair and as he moved around I couldn’t help but see that his huge package was falling out the sides because of how small the loin cloth was and how big his cock had been. He looked at both of mom and I and asked us a rather odd question.

“Where did Alice want it?” he asked

“In her rabbit hole while she licked the queen of hearts.” Mom said without missing a beat.

I recognized it from one of the versions of Alice in wonderland and I guess it was some kind of pass phrase to keep from anyone just showing up.

He smiled at both of us then looked at mom then at me as he said “That she does, and I hope both of you do to.” He said teasingly.

Mom and I walked past him as we both smiled.

“The night is young my big strong ape man.” Mom said running her fingers over his bare chest.

I just giggled as girly as I could as I let the palm of my hand brush against his big package like I was going to play with it but just teased as I walked by and wiggled my hips like mom did.

I followed mom inside as I casually took in all the sights on the way. The bathroom had a woman giving a man a blowjob in a bikini while the next bedroom we past had a slutty police girl and slutty fireman girl making out and fingering each other on the bed. I could feel my dick starting to leak and twitch in my lingerie but I was able to keep it under control and hidden away, at least for now.

After mom and I had walked through the entire house and saw some of the action, we stopped at the living room where people were mingling and having a few drinks.

Mom stopped me then brought me in close to whisper in my ear. She told me that she was going to split up from me for a while so we could have some fun but she would find me later. I told her ok and she went over to a group of women by the wall and gave them a hug. I guess she knew a few of them but that was alright I wanted something to drink anyway.

I strutted my way over to the table where the punch with whiskey was and the little assorted snacks all over the massive table that was set aside. So I started to eat and take in the scenery as I got into a bit of small talk with some of the other guests while I tried to find someone to have some fun with. Eventually I saw mom talking up the man who let us in in the Tarzan costume and a petite younger girl in a sexy French maid outfit before she took both their hands and lead them upstairs to which I can only assume was one of the “play rooms” for when couples got together.

I have to admit I was a little jealous of mom getting some action before me but I was soon to get my fun as well. Soon I found a sexy guy in a fireman costume and decided to make my move. I strutted over in my sexiest manner with an extra drink in my hand to offer him to try and break the ice and get the ball rolling for a conversation. We got to talking and I have to say he seemed very interesting and loved the idea of a sexy crossdresser like me but it was only on a few conditions.

“First of all, I don’t like to suck cocks and I don’t like them in my ass so if I fuck you that’s just how it was going to be. Secondly, my girlfriend over there in the slutty Irish bar wench costume wants to join us in a threesome and if you need to use your cock it is for her. Finally when we get to the cum shot, my wife doesn’t swallow but she does like to taste it so I hope you don’t mind taking over that part.” He says with a wink and pointing to a beautiful red head with a short green skirt and black top.

I told him that I loved that idea and would love it if she joined us. He called his girlfriend over and we introduced ourselves to each other before heading upstairs. I could hear moans from one of the rooms and was wondering if that was mom or the other girl that was having so much fun. I couldn’t wait for my turn so I tried to hurry our pace a little so we could get there sooner.

Finally, we reached the bedroom and I have to say it wasn’t much but it was a great room for the purpose it was about to be for. I grabbed the girlfriend, whose name was Amanda and pushed her onto the bed so she was on her back. Then I jumped on top of her and lifted her legs up and bent my legs so it was like we had two naughty pussies rubbing together that was just perfect for the fireman (whose name was Todd) to rub his big fire hose between. The girlfriend Amanda had a wonderful body as well, her ass was nice and curvy but she didn’t have as big as one that I normally like and she had a nice set for B cup tits that were amazing soft and perky. Her skin was white as snow and it made her bright red hair stick out that much more. I started to make out with her and touch all over her amazing body. Todd was slowly stroking his cock as he watched and soon I had Amanda out of her panties and slowly fucking her pussy with my two middle fingers. Her body quivered and she moaned wildly as I could feel her pussy drool with juices and grasp my fingers as tightly as they could hold them. I couldn’t hold my excitement anymore as my cock finally emerged from its thong prison. I moved it to the side enough so I could position myself between her legs. I had to stop for a minute because one of the rules to the party that I found out is that everyone needs to wear a condom when they have sex. I was just glad that rule didn’t say anything about the facial cum shot at the end. So I rolled on a condom and started to fuck her in her sopping wet pussy. I started out with slow thrusts and built my way up to a good pace when Todd got onto the bed just beside my head and stuffed his 7.5 inch cock in Amanda’s mouth.

We took turns sucking on Todd’s cock until his shaft and head were glistening and soaked with saliva. He rolled on the condom and I begged for him to fuck me first which he gladly obliged. Todd got behind me and stuffed his massive member into my ass and began to ram me with all his might, sending the shock waves right through my body and into his girlfriend Amanda.

We continued to fuck like that for a while before switching up our positions. Next Amanda rode me while Todd took her in the ass and we pounded her pussy as hard as we could, making her squirt into another orgasm as well as Todd and I. by the time it was over, Amanda and I were both covered in cum as we laid there panting from the great fuck we just had.

Suddenly I heard a knock on the door and mom’s head popped through.

“Sorry to bother you guys, I just had to talk to my… daughter for a moment.” She said with a smile.

I left the room and the couple just laid on the bed as they kissed and cuddled. I felt like I had truly brought them closer together which gave me a sense of pride.

Mom looked like she had quite a time as well. Her costume was all in disarray and her makeup was smeared like she had tears running down her face and her lipstick was simply a mess.

She pulled me out of the room because it was almost time for the competition and for a change of costume. It turned out that whoever had the best couples costume that went together and looked the best each one a 5000 dollar gift certificate to a love apparel and sex shop called “Horny As Fuck”. This got me excited and very determined to win and mom had the best idea of how to do that. I looked down and she had both of the bags from the car with her and I picked one up before following her to the bathroom to change.

When we came out, I felt so confident in our costumes that I just knew we would win. Mom was in a slutty police girl uniform with cut off shorts that let her ass hang out the bottom and were crotchless that had a nice slit that exposed her pussy perfectly and went all the way back to past her asshole. She also had on a strapless thong which was only the part that covered her pussy and went between her legs and up her ass. It was like the only thing that was needed to cover her goods was used and nothing more. When I first saw it I wondered how it would stay up but I soon found out it had a wire built into the fabric to bend it to the shape of your body and fit it without the need for the straps to hold it on. For her top it was nothing but two badges with strings that she used to tie behind her neck and her back. Finally she finished her outfit with a cop hat, dildo baton that was a good nine inches with handle and strappy heels. One last thing she did was tie her hair back into a pony tail to give her that powerful police woman look she wanted.

My costume went with hers nicely. I had on a short pleated skirt and thong with a top that was like a short sleeve, button up shirt that covered my shoulders and chest but stopped just past where my bust would be. I put in some breast forms to give my chest a sexier appeal and a nice D cup. The entire outfit was a bright orange like those jumpsuits you see in some prison movies and even had a prisoner I.D number on my chest to make it look even more authentic. I put on a blonde wig and finished with some strappy heels like mom and a tramp stamp on my lower back that read “Prison Bitch” just above my ass.

I felt it was great and we looked amazing but mom stopped me and said she just had an idea for something a little extra and told me to lean against the wall and spread my legs a little. Soon I felt mom begin to write on my upper thigh and below my ass. It was a little heart and she wrote “Anal Slut” below it. I thought it was perfect but then had an idea of my own. I told mom to take out some cuffs she had in the bag and cuff my hands behind my back and walk me to the party. Needless to say she loved that idea and we did just that before walking into the party again. As soon as we got there, I noticed all the people at the party watching us. It certainly drew their attention as I figured it would the judges as well.

Everyone took turns going into the middle of a big circle and showing off their costumes. When it came to mom and I’s turn, we made sure we gave a show to improve our chances and that we did. I strutted into the middle of the circle with mom saying commands like a police woman would and calling me “slut” and “dirty little cunt” before dropping me to my knees. She slapped my face with the dildo baton and I stuck my tongue out to lick it up like a real cock. As I did this, mom would bend over and slowly move her hips back and forth while we conversed together like it was really happening but with lots of sexual innuendo like:

“You want this tool don’t you? You want to use it on me and make me feel like your bitch like I make you every night! Go on say it! I want you to tell me what a dirty little cunt like you wants from a hard cop like me.” Mom said with a smile and running the dildo baton around my lips.

“Yea I want it. I want it bad! I want to use that tool and by the time I’m done you will be whimpering and begging for me to stop, but I wont! I will take that tool and put you on your knees where you should be!” I teased back as I spit on the dildo baton and making it run with a bead of liquid from the tip and down the shaft to the handle where mom’s hand was.

It wasn’t long by any means but mom did spank my ass with the baton a couple times before hauling me to the couch to the side to end our little performance. Everyone clapped and I could tell that the next couple was a little nervous as of how to follow up on that. However it was exciting and lots of fun. By the time the show off part of the competition was over everyone was hotter and hornier then a room of rabbits in heat.

Soon the judges took the middle of the room and I was amazed to find that two of the four judges were Amanda and Todd and one of the other judges was Tarzan who let us in and went with mom and the sexy French maid upstairs earlier.

“And the winner is… Slutty Police Woman and Prison Bitch!” one of the judges said with excitement.

Mom and I were so excited we rushed to the middle to get our prize and our little trophy. Mom and I hugged and the crowd applauded but I could see that there were a few people that were really hoping to have won but weren’t overly angry and jealous. Then another announcement was made after we got our prize.

“Now for the main event of the night. Ladies and gentlemen, it’s Orgy Time!”

With that everyone grabbed a partner whether it was man or woman and began to make out and take off clothes. Mom grabbed the fireman Todd, I was with and I went over to Tarzan.

“Want to make me your jungle bitch Tarzan?” I said seductively.

He just grabbed my ass and held me close as he started to kiss and suck on my neck. I could feel his hand massage and tease my hole and his cock growing bigger. I reached down and it was a good 9 inches and an average width. He laid me down on the couch with my head over the arm rest. He moved his loin cloth and out popped his erect and twitching cock as he wasted no time in putting it in my mouth.

He started to push his cock slowly down my throat like he was testing to see how far I could deep throat him which I have to admit was very thankful for as I love to savor the taste rather then gobble it down before I know how I can handle it first.

It wasn’t long before he had a steady pace going and was fucking my throat. It tasted so good and I could feel his slimy precum coating my mouth each time he pulled out enough so just the head was in my mouth. Suddenly I felt someone pulling down my thong and freeing my hard cock once again. It was the French maid and she was getting on my cock to ride me while I sucked the cock. I guess it turned her on to watch because she wasted no time before she was bucking her hips wildly on my cock.

We continued like that for a while before the two of them traded off. Now the French maid was sitting on my face and I was driving my tongue in and out of her wet pussy and sucking on her clit while Tarzan filled my ass with his jungle meat. I pushed my tongue in and out, swirled up and down her lips and her clit as I tickled my nose on her ass hole.

Soon she orgasmed and pulled her pussy off my face. I was gasping for breath and Tarzan was reaming out my hole good and pounding me like he was waiting for it all night. I guess this is why mom looked so worn out when I seen her earlier.

I was able get a chance to look around and by now the entire party was having sex. It was a huge collection of people fucking in every position and even getting together for a group to whoever was closest. I seen men fucking girls doggy style with the woman eating out another girl on her back while that girl sucked off another guy. I even saw several girls with strapons fucking each other like a train of dildos inserted into the next pussy ahead of them.

Just then the French maid got back on top of me and started to ride me again but this time she faced Tarzan and started to make out with him as they used me like a little sex toy. I looked over and saw mom using her baton on a girl in a school girl costume.

This continued for a few hours and we traded partners fairly regularly, I felt by the end of the night mom and I had been with almost every person at the party. Some people had passed out from either exhaustion or from drinking too much but others collected their clothes and were ready to go home. By then I was laying on my back on the kitchen table covered in cum and mom was looking for me. She was looking fairly sticky with dried cum as well and her top with the badges were in her hand with the baton. My skirt was half way up my body to my stomach and I had lost track of my thong over an hour ago.

“Ready to go home sweetie?” Mom asked.

“yea, this was a great Halloween mom and I’m glad we came.”

“Me to sweetie.” She said.

We collected our prize and our bags and left the party. When we got home I took my dirty clothes and put them in the special hamper I had for my dirty Missy clothes. Mom had just gotten out of the shower and had only a towel around her head as she came into my room. I was naked as well and just waiting for my turn with the shower.

We talked for a bit and mom told me that she got a few numbers from a few of the people we were with and next week we could cash in our gift certificates at the shop. I was happy but utterly exhausted as I went to take my shower.

To be continued

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