Mickey

Story Info
Halloween party trick or treat?
3k words
4.43
13.4k
12
0
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
grgy56
grgy56
1,564 Followers

Mickey

It was a great opportunity to dress up for Halloween. An office VP was having a costume party at his large mansion and I was excited to go. I decided on dressing up kind of a bad version of Mrs. Doubtfire where it would be very obvious that I was a guy in drag. In reality and in private, I dress up as a woman all the time.

I could barely wait until the day arrived. I started prepping early knowing that I'd probably be distracted while getting ready. In the shower, I checked for body stubble and glided a razor over a few spots including my cock, balls and crack. I carefully dried myself off before applying some scented body lotion (a slippery finger accidentally slipped into my asshole a couple of times). My uncut six-incher was rock hard.

I didn't bother covering up with my fuzz pink dressing gown and jumped straight onto my bed. I grabbed my vibrating toy and shoved it up my hole. My fingers surrounded my pre-cum slick shaft as I tried to slowly jerk off but the hard vibes in my ass made that impossible and my gripping fist moved up and down at a blinding speed. It didn't take too long before wads arced from my pee hole and onto my face and chest.

Satisfied for now, rather than wipe up my cream, I licked up as much as I could before rubbing the rest of it into my skin.

Although "Mrs. Doubtfire" would probably have worn granny panties, I figured it would be covered up anyways. I hooked my pretty, white lace bra around my back. It had double-D cups that I would normally fill with my oversized, custom, self-adhering breast forms but in case I got caught out, I'd stuff them with something else. The lace thong was tight enough to keep my dick under control tucked but the back strap dug deep into my crack. I hooked my garter belt around my waist. While I really enjoyed slipping my smooth legs into some sexy, shiny, sheer and expensive stockings, I opted for set of heavy, beige stockings and held them up with the ten dangling straps. For that extra granny look, the stockings were very laddered and baggy.

I was very practiced donning make-up but I purposely made a mess of it. I did brush on some mascara to thicken my naturally long eye lashes and then after I painted on my eye liner, I plastered on some garish shadow onto my lids. I overdid the pink coloured cheek blush and smeared on some vibrant red lipstick and shiny, sparkly sealer. I carelessly plopped on a blond wig on top of my head. With straw like hair, it was a cheap, unkempt one; the first one I ever bought.

I slipped into a slightly shorter than knee length, front button dress. I bought it at an antique store and while the body and bodice was snug, it was dowdy enough to give me that proper look. I clipped on some gigantic, fake pearl earrings and a matching necklace then I stepped into some black pumps with a heavy wedge heel (typically I now always wore tall stilettos). I looked at myself in the mirror. "Oops! Forgot my boobs!"

When I first started to dress, I made myself some boobs out of material to fill out my chest. They started out a C's but after my bust size increased, they were slightly bigger than double-D's. When I stuffed them inside, they of course looked stupid and ridiculous and were so big that the front buttons strained to keep from popping open.

I took a cab to the VP's place just in case. When I got there, the party was already going. I saw a number of co-workers and others whom I assumed were friends of the VP. While I said my greetings to them, there was someone I didn't recognize. He was pretty gargantuan and gregarious. I could tell he thought he was the life of the party. He was introduced to me as Biff the neighbour of the VP.

"Hey. Great outfit!" He said to me. "Nice tits but I don't remember Mrs. Doubtfire having such big ones!"

I reluctantly thanked him and found an excuse to gain some distance between us. I grabbed a cold beer and mingled around. The first one went down quickly, followed by a second and third and it was only about 10:30. I tried to buffer my belly with a bit of food.

"Hey, Mrs. Doubtfire!" Biff called out to me as he approached. "Hey. I'm sorry if I offended you before. You seemed to be a little pissed at me when we met. Here. I brought you a beer. Cheers!"

"No problem. Thanks for this." I responded and tried not to be too cold. "Cheers!"

I took a long swig from the bottle and nearly finished half. For some reason, I found I wanted to drink the rest of it and gulped down the rest of the beer. I thought I was fine but about twenty minutes later, I started to feel a little woozy. I plopped down on a leather sofa. My eye lids started to get heavy but before I closed my eyes completely, I saw Biff point at me and laugh.

I opened my eyes with a start. I looked at the time and saw it was almost midnight. I did feel better after a rest and I thought to myself. "Wow! I was out for a bit!"

The crowd was a bit bigger than before. I stood up and moved around. I found some water to rehydrate. As my mind cleared, I felt different. I couldn't put my hand on it but I just felt different until I passed by a mirror. My straggly, straw hair was nicely coifed. My make-up was perfectly applied albeit heavier. My lips were a bright, sparkly pink. A closer look showed my long lashes were even thicker and longer than before. I grabbed my boobs. They were full and fleshy, not like the fake ones I had on before. I shook my head in disbelief at the reflection and dashed off to the bathroom.

I undid my dress buttons and pulled up my bra. I had tits! Real tits! Huge real tits! They way bigger than my fake ones; I'd guesstimated J or K cups. The aerola were bright red and my nipples were the size of cherries. I cautiously gave one a pinch and immediately felt a gush of wet between my legs. I slipped a hand inside my now wet panties. "Fuck! Where's my cock!?"

I pulled down my panties to verify my cock had indeed gone somewhere. In its stead was a nice shiny, slick slit. A little nub protruded from between. I touched it with my finger tip and instantly spasmed. More wet. A lot more. Juices were running down the insides of my thighs.

I tried to pull off my wig but couldn't. My hair was real. I tried to wipe off my lipstick but again, I couldn't. They were actually bright sparkly pink. Then with my panties pulled down I noticed my bum. It was much firmer and rounder than before; a perfect sissy butt.

"What the fuck is going on?" I asked myself. I needed to find out. As I got redressed, I found my entire body was overly sensitive like it was one gigantic sex organ. It took some effort to cover up without experiencing too many orgasms.

I opened the bathroom door and was face to face... Actually face to chest to the taller Biff (I didn't remember him being that much taller than I was). He looked down at me and smiled. I tried to get around him but he blocked my way. He pawed my breast and pinched my nipple through my clothes. My pussy gushed and my knees buckled. I wanted him. I needed him.

Biff took me to a bedroom and laid me on the bed. I rolled over trying to get up but found I hadn't the strength. I felt Biff flip the back of my dress up. He kicked my feet apart then pulled my panties aside and entered me. I moaned out. "Uh! Oh fuck! Yes! That feels so good! Fuck me!"

Biff was relentless. After three, I lost how many times he made me cum. It didn't matter where he stuck me with his cock: cunt, ass, mouth... I came and came and came. And I came hard!

I awoke and somehow found myself in my own bed. I laid there thinking about last night about how Biff fucked me silly and that it was a bad (good) dream. Just the thought of it started a tingling in my groin. I snaked a hand under the covers, along my smooth belly and between my legs. A finger ran through a wet slit and over a hard nub. I came. "Uuuhhh...!"

"What the...!" After I flipped off my blanket and looked between my thighs. My cock was still a cunt! I jumped out of bed and nearly fell on my face. I still had gigantic tits! I stared at myself in the mirror. My hair was still long and blond. My lashes were still thick and long. My lips were still plump and very sparkly pink. I was still the same from last night.

It took a bit before the shock wore off a bit. I pulled on a loose fitting tee and some shorts. My huge tits bulged out and my big, hard nips protruded through the thin cotton material. I did like the way my legs looked though. They were nice before but now they were very smooth and well-shaped. My bum filled the shorts out very nicely too.

I padded over to the kitchen and found a note from Izzy, a co-worker. "I brought you home last night and put you to bed. Call me."

It was late morning when I called Izzy.

"Yeah that Biff guy mickey-ed your drink with some sort of X-change that he developed. He didn't even try to hide it. In fact he bragged about it to everyone. " Izzy told me. When I asked why I hadn't changed back... "Apparently it was some sort of extended version of it that would last for a day or so."

I found out where he lived with the intent on confronting him but the angrier I got, the wetter I got. Still I needed to "discuss" things with him. I couldn't go dress as I was so after a quick shower, I changed. Actually the shower took a pretty long time. Every time I ran my soapy hands over my body and especially my boobs and pussy, I experienced strong tingling between my legs that needed to be satisfied.

One good thing about whatever he spiked my drink with was my hair looked great. My face was naturally pretty and needed very little if any make-up. I loved how my long lashes and pouty lips made me look so girlish.

None of my full cup bras would fit without squishing my boobs too much so I wore a black, demi-cup shelf bra. The lacy cups were edged with frilly lace and tickled my nips. Then I stepped into my matching boy short panties. When I pulled them into place, the middle seam not only dug into my ass crack but the crotch forced its way into my slit and made me cum. After I regains some composure, I pulled on a bulky sweat shirt and jeans to try and hide everything before stepping into my runners. Then off I went.

I arrived at Biff's and banged angrily on his front door to his huge house. It was as big as or bigger than the VP's. The door opened and I was greeted by a grinning Biff. He was dressed only in a dressing gown. "Hello, Mickey! I was expecting you. Wow, don't you look pretty this morning?"

"What the fuck did you give me?" I demanded without returning the curtesy. "What gave you the right?"

"Whoa Mickey! Why don't you come in and I'll explain everything. I'm just having some coffee. Would you like one, Mickey? I'll get you some."

"And stop calling me Mickey!" Fuming and without thinking, I stepped through the doorway inside. Biff placed his hand on my lower back and guided me. I let out a tiny moan and there was a slight gush in my panties. He told me to sit in his huge, carpeted library and soon returned with a couple of cups of coffee. He handed me one and I took a sip then another and another. Almost immediately, I felt my breathing change. It became a little heavier and deeper. I looked at Biff. My lust for him grew stronger and stronger.

"Yes, I developed a different version of X-change. I wasn't going to use it on anyone but when I saw you dressed up, something just clicked in my head. At first I did it as a prank, but after you changed, I found myself falling for you." Biff Admitted. "You see a couple of years ago before I moved here, I was married to Mickey... Michelle actually, the most wonderful, the most beautiful woman in the world. She was the most perfect wife. Then she was killed in a drive-by shooting and it devastated me."

I nodded my head but started to find concentrating on his admission was getting more and more difficult.

"Like I said, it was a Halloween prank but the more I looked at you, the more you reminded me of her, the more I wanted you." Biff told me.

He continued talking to me but I didn't hear a word. My breathing was now more of a panting. My pussy was sopping and aching. I fell to my knees and crawled over to where Biff was seated. I undid the sash holding his robe closed and flipped it open. He had a beautifully athletic sculpted, hairless body including his crotch area. His cock was semi-flaccid but was seven uncut inches long and growing bigger. I took his heavy manhood into my hands and stroked him until he was over eight beautiful inches hard. I carefully pulled back his foreskin and exposed his red knob. A big droplet of clear pre-cup oozed from his piss hole which I eagerly lapped up. It was quickly replaced with another bead that I also lapped up; then another and another until it was almost free flowing. I surrounded his head with my plump, pink lips and lapped him with my tongue.

My head automatically started to bob up and down as I took more and more of him into my mouth until I found my lips around his base. I sensed he was deep down my throat but I had no gagging reflex. Biff placed a hand on the back of my head to hold it there but did not force it down. I did that by myself. I lost how long I sucked on his hard shaft. Biff pulled me off then reached over and pulled my shirt over my head. "Mmm... I gave you beautiful tits, didn't I Mickey?"

I leaned forward and sandwiched his erection between my massive mounds. Each time I move my boobs up and down, his cock hit against my chin. I lowered my head and sucked his knob as I continued giving him a tit-job.

I found that I had somehow undid my jeans and pushed them down to my knees. Biff brought down a strong slap onto my cheek. "Nice ass too, eh Mickey?"

I stood up before him and was about to push down my panties but Biff stopped me and guided me on top of him. He held each breast in his hands and in turn, sucked on my sensitive, engorged nipples. I grounded my hips into him so that my covered pussy rubbed on the underside of his dick. I pulled my panties aside and slid my slick slit on shaft. It felt so good but I wanted him... I needed him inside.

I raised my hips until his tip popped into place and impaled myself on him. His thickness stretched me as he entered. I was overjoyed when he told me. "Oh, Mickey! You're so tight!" I squeezed him even tighter; he moaned loudly. I came.

I hugged my arms around his neck. Still inside, he cradled my bum, lifted me and then carried me to his bed. Each step drove him in deeper. I came four or five times before he laid me down. With him between my thighs, I wrapped my legs around his waist and pulled him in. My heels dug into his firm, muscled ass. He fucked me gently at first but as I spurred him on, he fucked me harder and harder. I came and came and came.

I'm not sure when he filled me with his wonderful cum. I awoke sometime later. Asleep, Biff was quietly breathing beside me. My pussy was soaked and sore but a good sore. I used a finger to swipe my slit and collect our leaking juice and sucked it off before I nodded off again.

I awoke to find myself alone in bed. The clock told me it was late afternoon; almost evening. My body was still Mickey. I smiled to myself while thinking how Biff made me feel.

When I arose, I found that Biff had laid out a red silk dressing gown for me. I slipped it on and tied the sash into a bow. The gown fit beautifully and I loved the black lace trim and embroidery on it. There was also a pair of four inch mule slippers for me to wear. I stepped into them and went to find my lover.

I finally found Biff sitting by his lonesome in his enormous kitchen. His head was down and seemed to be sobbing. "What's wrong, Biff baby?"

"I'm sorry. I miss Mickey so much." He started. "I'm so sorry. I've taken advantage of you for my own purposes."

"Oh no! Don't be sorry." I went over and gave him a warm hug. "I've actually really enjoyed being your Mickey. I know it's not the same but if it made you happy... makes you happy, I'd love to spend the rest of the weekend as Mickey and with you."

grgy56
grgy56
1,564 Followers
Please rate this story
The author would appreciate your feedback.
Share this Story

Similar Stories

Shemale Sister-in-Law Man gets massage from sister-in-law with shocking results.in Transgender & Crossdressers
Teacher Surprise College student bumps into his high school teacher at a club.in Transgender & Crossdressers
Summer Camp for Naughty Husbands Ch. 01 Steve learns more about his loving family.in Transgender & Crossdressers
Mommy's New Daughter Pt. 01 Mother and friend think of an unorthodox punishment for son.in Transgender & Crossdressers
The Halloween Sissy Party - Pt. 01 Hot wife, Carla, convinces hubby to become a sissy.in Transgender & Crossdressers
More Stories