This year for Halloween I planned to dress like a slutty secretary. I wanted everyone to be shocked it was me. It was to be my ultimate costume. Cause nobody would ever expect it. Nobody knows about my alone time. That I like to dress up and play with my boy hole! I set the plan in action months before. Watching makeup tutorials I mastered the seductive look. I worked on my voice and practiced walking in 6” stilettos.

On the outside I’m a mans man. I have a long 3 year old beard, tattoos, I fart and drink beer . I drive a jacked up pickup truck and wear camouflage. Nobody would ever expect this. The day before the Halloween party I shaved my beard and all my body hair. I was silky smooth .I did my makeup and got dressed. I was hot so hot I turned my self on and needed to be fucked lol. So I changed not to mess up my clothes. Just slipped into a white silk nightie and grabbed my purple 10” dildo and fucked myself all over the house with it, into the late night. I woke up the next morning and I looked in the mirror. My cock grew to 7” and I was so turned on again. I sipped my coffee and bounced my little bubble but up and down on my dildo. In no time my cock was squirting. Not to waste my seed I came into my coffee cum . Nothing like a little slut creamer lol.

So the party was at 8pm . At 6 I started getting ready. One thing I didn’t want to wear panties, but my cock would show, so I had a plan. I sat on the bed and got my tape .
My cock soft is only about 1 1/2” so I pushed it inside me and pulled the skin of my balls up over everything. And taped it, it works well until you have to piss. But I just brought extra tape already cut to fit.
I wore my cock taped while I got ready so I would pee before I left and make sure it was easy. I put my makeup on , Smokey black eyes and red matte lipstick finished it off. I bought new secretary glasses. Put my black layered wig on and got dressed. Black thigh high stockings with a matching garter and lace bra. I got some of those silicone breasts to pack out the bra. A black pin stripe knee length pencil skirt with matching blazer. Underneath a white button up blouse that you could see my bra through. 6” black stiletto heels, a tennis bracelet. Earrings and of course my nails were French tipped.

I rented a car for the event and I even tricked the guy at the car rental, he asked me out and I was like it’s Halloween buddy in my guy voice he was shocked.

I pulled up to the house party at 9 pm fashionably late of course. As I walked in the house I heard people whispering, damn that’s a sexy secretary, who’s that? , she’s gorgeous.
That sky rocketed my confidence. I walked in and demanded attention, my ass and legs looked amazing . I walked and stood by my friends and they had no idea. They were actually checking me out. I even chatted with them and they were clueless. I kept the character up for over a hour till my one friends wife says where the hell is chris at?

I giggled. I’m right here!
Jaws dropped to the floor. I cracked up laughing I got y’all!
One friend was like dude a was trying to fuck you, I replied with yeah well your game could use some work.

We all partying together for a while I decided to head home and drink. I walked to my car and was bent over digging in my purse looking for my keys when I felt a pair of hands rubbing my ass. My skirt slid up my thighs and over my bare ass. The street was dark and I was at a bad advantage. I turned my head to see my best friend John smiling.

It was so quiet I heard his pants unzip and felt the head of his cock brushing my asshole. I felt his spit soaked fingers rub over my hole, and in my ass. He held my hips firmly and pushed his thick cock balls deep into my asshole. I muffled my moans with my own hand as he pounded away at my back door. Now your a real girl baby he whispered .
His balls slapped my taped genitalia over and over. I felt his cock twitching and filling me with his juices. I never felt so sexy in my life. He pulled his cock out of my dripping hole and pulled my skirt back down. I got out of the car and squated down taking his ass soaked cock in my mouth, sucking him clean. Then put his cock away and sat in my car.

Want some company tonight ?he smiled
Depends I laughed
I looked at his cock” he got any more in him?”
Oh yeah all night long he laughed
Meet me at my house, I smiled and drove away.

I got home and pulled my tape off I had to pee so bad. I was walking to the fridge when a knock on my door. I opened it to see John. Come in!
Want a beer?
Of course!
We sat there drinking, god your hot he laughed.
He sat on the couch and I said I was gonna get changed.
Leave the stockings and heals he grinned.
I got undressed and slipped into a black silk nightie and walked back out. He smiled and a straddled his lap sitting down. His hands ran up my belly feeling my tiny tits. I grinded my ass into his lap. I bit my lip and he pulled me close and we started making out. I unbuckled his pants and released his hard b**st. I lifted my ass and lowered down, his cock slid deep inside my cum coated ass. We made out for a hour as I slowly worked his cock in and out of me.

His hands pulled up my gown and he grabbed my soft cock. Why ain’t you hard? He asked
I giggled it’s not about my cock just yours !
It’s tiny he smiled, I wanna suck it!
He lifted my nighty over my head and threw it away, his mouth sucked My nipple I moaned. He jerked my cock between his fingers, I continued to rock my ass on his cock. My fingers running through his hair it was pure bliss. Let’s go to your bed he moaned.
I lifted off of his wet cock and leaned down sucking it clean. Mmmmm I moaned and pulled him to his feet. Grabbing his hand I led him to my bedroom. I laid on my back my legs spread wide open. He lunged at my crotch, pushing my legs up and he licked my cummy asshole. I felt his tongue inside me. Omg I moaned. As he tongue fucked my tiny hole. He licked up my balls and lowered my legs, taking my tiny cock into his mouth. My cock grew to 7” and he sucked me hard.
Fuck me ! I begged
His tongue teased and licked my entire body. Finally he gave me what I needed that big cock. I laid on my back, he was between my legs, my heels in the air he pounded me hard. My cock started squirting all over my belly and nipples. I moaned as he slammed away at my back door. He switched up to doggie style and his balls slapped mine. He pushed me down to my stomach and pulled his cock out just to eat my asshole like dinner, he slammed back in and jackhammers my boy hole. He laid back and i cowgirl fucked him hard my cock flopping in his face , he watched with excitement.
He grabbed my hips and flipped me to my back. He thrusted hard until he roared a felt his cock flexing and I squirted yet again as he filled me.

John exhausted flips to his back. “Sit on my face!”
I straddled his head and sucked his cock . I thought he was gonna suck me but he pulled my asshole to his mouth and started eating his cum from my ass. I got the hardest cock from this. After I cleaned his cock I turned to look at him. His face covered in cum I had to kiss him. We made out with his cum.

He scooped some cum in his fingers and coats his asshole. Fuck me! I wanna feel it!
My hard cock pressed against his asshole and I pushed in. He whimpered as my shaft slid deep. Slowly i fucked him . It wasn’t long and I came. It’s a good thing cause he was crying like a bitch.

John spent the night and rocked my world in the morning and afternoon. He was gonna leave but didn’t we spent the entire weekend together, never leaving the house.

That work week we went back to our normal life. He did come over Wednesday night, luckily I was dressed. He slammed me over the kitchen counter and headed out. The following weekend we stayed in all weekend for a repeat of the first weekend. Except I didn’t fuck him. I’m the girl baby I get fucked! God I’m horny I wonder what John is doing?

Hmmm I’ll give him a call…

Halloween cross dresser

Write A Comment