October Surprise

By NPhillyDogg/Scedmark

Published on Sep 25, 2002

Gay

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I'd never been to a halloween party before, so when my girlfriend told me we were invited to one at her ex-boyfriends house, I was somewhat reluctant about going. The last time I was dressed up for trick or treat was when I was 11. I went as a urban cowboy. I'm 23 now. My girl, Yolanda, wanted us to go to the party as african royalty, but I told her I wasn't intrested in going. Yolanda pissed a bitch, complaining "you never want to do anything exciting", I responded that "I don't consider dragging my ass over to your uppity ex's house for some boring ass halloween party as being exciting". Needless to say, Yolanda decided to go as african royalty without me.

I had intended on going to the party all along, but I didn't want her to know I was going to be there. I wanted to observe her and her so called EX, without them knowing I was there. I knew Raymond (her ex-lover), had wanted to get back with Yolanda again, and I knew Yolanda still had feelings for her "first love", even though she constantly denied it. Raymond was a girl's dream, nice looking, built, athletic, smart, had a good paying job, drove a decent ass car. I myself was good looking as well, have a pretty fair body, drive a second hand car, and worked pay check to pay check. I mean, I ain't nothing to sneeze at, but Raymond had it going on. Comparing the two of us, I sometimes wondered why Yolanda was bedding down with me instead of him. I knew she had found out he had been cheating on her, and I know that she's always claimed that thats the one thing that she could never forgive.

Halloween night, Yolanda looked like a million bucks with her home-made african garb on. She wore an all white bed sheet, in which she twisted, wrapped, tucked and sewed to fit her form. She accessorized it with gold chain belts, fake jewelry, and sandles. She wore her long shoulder length hair up off her neck, and wore special egyptian like make-up. She actually looked beautiful. I wouldve been proud to walk into any party with her on my arm, had I not had my own ensidious plans.

Yolanda was still mad that I wasn't going, but kissed me "goodnight" anyway. I peeped out the window until I saw her car drive down the street, then I bee-lined to the back door to let my best friend Darryl (whom was my partner in crime) in from the backyard.

"Damn man, I was wondering when your ass was gonna let me in. That nosey ass old lady across the alley kept staring at me like I was a burgler or something. I kept expecting the cops to come drag me outta the alley n'shit!"

"Shut up nigga, get your ass in here." I said. "Did you bring the stuff?"

"Right here nigga. And let me tell you, I ain't enjoy the odd looks we got when we bought this shit either playa. You gonna be owing me big time for this here shit man." Darryl said, handing me the shopping bag I had asked him to keep at his place until tonight.

I snatched the brown bag from his hands. "Nigga, just gimme my shit and shut up."

"Yo, I saw how Yolanda looked when she left man, damn thats a fine ass woman you got." I smiled knowingly. Darryl was my best friend, but I didn't doubt for a second that he would fuck Yolanda in a quick minute if she gave him 2 looks sideways. "Your ass right to go to this party to check her out. I bet that ex-boyfirend of hers is gonna be all over her big juicy ass soon as he sees you ain't there." he said, fueling my insecurities.

"Man, shut the fuck up." I said, running up the steps to get dressed. Darryl followed close behind.

"Where the hell you think you going?" I asked when I got to the top of the stairs.

"Nigga, you gonna need help gettin' that shit on." he said defensively.

"How hard can it be?" I asked.

"You ever wear woman's clothes before?" he questioned.

"No."

"Then lets get to it then." he said.

We walked into the bathroom, where I started to undress. Darryl opened my bag, and pulled out part of my costume. "Here, put this on." he oredered, handing me the size C-cup stuffed padded bra we purchased at a novalty store together (which brought us our first of several strange looks from sales clerks).

"Thanks nigga." I said sarcastically. I didn't see why I needed him here to pass me the garments. I knew he just wanted to trip watching me get ready.

I put the bra on, and Darryl helped my snap it into place behind my back. "Thats a first." he said, refering to helping someone to snap ON a bra. He then handed me the panty-hoes.

I looked at Darryl curiously. "You ain't getting excited by this, are you playa?" I asked jokingly.

"Yeh nigga-" he answered back. "-ain't nothing more exciting then watching some hairy nigga in boxers, bra and panty-hoes." he laughed, handing me the dress.

After realizing I had the hoeses on backwards (resulting in me taking them off and putting them back on), I put the one piece dress on. Darryl and I argued in the store about what kind of dress I should buy (bringing out second round of strange looks from sales peoples). He thought I should wear a dress down pass my knees, somewhere near my calves or ankles to hide my "hairy manish legs", while I wanted to buy a shorter sexier dress. I'd often been told by girls that I had sexy legs for a guy, and I saw no reason why I couldn't show them off. I mean, nobody would know it was me anyway.

I put the dress on, and Darryl helped my accessorize it with some belts and stuff from Yolanda's closet. I made sure to buy a dress that covered my chest so noone would notice my chest hairs, but I allowed my back out, expecting noone to be able to notice the difference from behind.

I had shaved eariler before Yolanda left, so my face was smooth as a cute baby's butt. I applied lipstick, rouge, and eyeshadow (as best a straight man can whos never held make-up in his hand before). Darryl handed me the big curly wig (which brought our third strange look from clerks), and helped my arrange it on my head just right. Then he handed my the size 10 pumps with a snicker in his voice.

I walked (cautiously) into the bedroom to view myself in the full length mirror. Darryl followed behind, the laughter in his voice disappearing somewhat. "You don't look too bad." he complimented.

I stood infront of the large mirror, and agreed. The make-up was passable, the hair was abit much, but it WAS holloween afterall. I'd have to get used to the pumps, but I felt I could manage. The dress clang to my hips, and being that I had a big butt to start with, it definately looked like a woman's ass in that dress. I was thoroughly surprised at how attractive I looked as a woman. Even with the above the knee dress.

"Told you I had nice legs." I said, staring at myself in the mirror.

"They aiight." Darryl said.

"They better then alright nigga. You know you'd want some of this if I was a real woman." I joked.

Darryl came up behind me and grabbed 2 hefty handfulls of my fat booty. "I just might TAKE some anyway." he said with a laugh.

I smack his hands away. "Look, but don't touch!" I teased.

I grabbed up one of Yolanda's matching handbags (something I forgot to buy), and had Darryl drive me to the party across town in his car. Darryl lite up a joint to relax me, as I got more nervous the closer we got to his house, "I'll call you on my cell phone when I'm ready to leave, okay?" I told him, placing the celly in the purse.

"Aiight. But I'm gonna be expecting something for my inconvenience." he joked. "Anybody ever tell you you got sexy lips in that lipstick?"

"Fuck you!" I laughed, getting out of the car. I walked up the steps to the party, and rang the bell. Someone dressed in a cat-suit opened the door, and I waved Darryl on.

"Hi. I'm Donna, catwoman. Who are you supposed to be?" the woman asked, trying to figure out my outfit.

"I'm a woman." I said in my deepest masculine voice.

The woman jumped in surprise, not expecting a male's voice. "Oh, nice costume! You're sure to win first prize tonight, I'm sure." she said, inviting me in.

I could hear the music blasting from the sidewalk. The place was packed wall to wall with people dressed in every character namable (all black of course). I saw, Mae West, Diana Ross, MC Hammer, Cleo Patra Jones, Batman, Superman, Spawn, Marilynn Monroe, Janet jackson, Peewee Herman, Jessie Jackson, Michael Jackson, Al Sharpton, Jason , Michael Myers, Leatherface, Aliens, Wizzards, Witches, Hookers, Pimps, Zombies, Bums, Crackheads, Boat Captains, Military officers, Nurses, Doctors, NFL Players, Rappers, Clowns, etc....

I found Yolanda about a half hour into the party, laughing and joking with her ex-(whom was dressed as the Scorpian King). He wasn't quite a buff as the Rock, but he pulled the costume off very well. Yolanda seemed to enjoy it, as she threw her head back in laughter at whatever stupid joke he said to her.

I parked myself across the room, fighting off drunk men and nosey women in the process, as I eyed my woman and her ex-loverboi. Through the course of the night, Raymond didn't leave Yolanda's side once. The two acted as host and hostess to all the party guests. I drank drink after drink, spying on the handsome couple, getting more and more angry as I watched him try to steal her away from me while she acted as if she was a willing victim. When I saw the two of them slip upstairs to be alone, I was sure to follow.

I crept down the hall, pretending to look for the restroom, and parked myself outside his half closed bedroom door. He took her up to his room, supposably to "talk to her in private". I peeked inside, and saw them standing in the middle of the room, right beside his king sized bed. I could just barely make out what they were saying.

"You look so beautiful tonight." he complimented, looking her up and down as if she were dipped in hersey's chocolate.

"Thank you Raymond. Your outfit.......is good too." she said, looking him up and down as if he were made of diamond. I knew diamonds to be "a girl's best friend".

"Well, I worked hard to fit into this costume." he said.

"And it barely fits." she laughed, refering to his skimpy underpants.

He laughed. "So, where's your boyfriend......whatshisname?"

"Karlon."

Yes. Karlon. Where's he tonight? Do he know how dangerous it is to let such a beautiful woman out of his sights like this. Especially when she's looking so particularily.......scrumpious."

Yolanda smiled. "He trusts me." she answered.

"Apparently. I don't know if I'd be so trusting." Yolanda's eyebrow raised. "Oh, I don't mean that against you, I mean...." then he stepped forward. "....I wouldn't trust these men out here. They don't respect relationships. They'll move in regardless of if you have a man or not." he said, wrapping his sneaky hands around Yolanda's waist and pulling her in closer.

"So I see." she said, trying to wiggle out of his clutches.

"Come on Yolanda, you know you and this Carlson guy ain't kickin' it like you and I did back when." Yolanda didn't say anything. "I know you still love me. And youre the only woman I look back on with regret." he stated, sounding like a bad soap-opera

"Raymond....."

"I know I messed up, but that was over 2 years ago. People change Yolanda. We had a good thing going. We can have that again."

"I HAVE a man." she stated clearly.

"Where is he? He ain't here." Yolanda hesitated. Raymond used that opportunity to reach in and kiss her. Yolanda didn't fight it. She let Raymond's mouth meld to hers as he wrapped his arm around her waist, and slip his tongue into her mouth.

I felt my blood pressure rise. I fought the urge to rush into the room and shoot the two of them dead. It seemed as though they were kissing for hours, where as it only lasted 30 seconds tops. Raymond broke the kiss, and studied Yolanda's face for a reaction.

{WHAM} she slapped him across his cheek. Raymond stepped back, holding his bruised face.

"I told you before Raymond, I HAVE A MAN." she said angrily, as she stormed past him.

Raymond grabbed her arm. "But...."

"And he's more man than you will EVER be!" she snapped, yanking her arm from his grasp.

I ducked into the next room, just in time as Yolanda flung open the bedroom door, and flew past me on route down the stairs and out the front door to home. I laughed to myself, then suddenly felt bad for not trusting her in the first place. I had to call Darryl on my celly so he could pick me up. I had to get home and make it up to my woman. Just as I was about to reach into my bag, Raymond walked out of his room, and spotted me standing in the empty room next to him in the dark.

"Oh, I didn't know anyone was there. Can I help you?" he said, distracted.

I held up the cell phone. "I just needed somewhere to make a private call." I said, in my softest feminine voice.

"Oh. I'm not disturbing you am I?" he asked, coming into the room with me.

"Uh....uh-ah." I whispered.

"Good. Cause a pretty woman like you shouldn't be left alone in the dark....without a male escort." he flirtted. I couldn't believe this guy.

"Well, all done." I said, trying to walk out past him.

"Why in such a rush?" he asked, touching me on my arm. He felt the definition of my bicep, and drew a breath. "So you work out, I see. So do I. Feel." he said, taking my hand and putting it on his much larger arm. Involuneetrily I squeezed the muscule.

"Like that?" he asked, flexing it for my benefit.

"Yes." I whispered, trying again to get away.

"That's not my only hard muscule." he said, taking my hand and moving it down to his crotch. Involunteerily, I squeezed that muscule too. It pulsed under the touch, and I instantly pulled back my hand.

"Don't be scared. We all alone. Its cool." he said, pulling me in closer to him. One hand held me in place by the arm, and the other hand traveled down my back, and landed smack dab on my butt. He squeezed my ass with his big strong hand. "Ummm, thats nice. You got a nice ass." he said, making me blush. This was the second time tonight a man openly squeezed my ass.

Raymond pulled me in closer. I could feel his breath on my face. Our lips touched, and suddenly, Raymond's thick wet searching tongue was in my mouth. I gasped at the shocking kiss, and struggled to break free. I could feel his front pressed up against mine. His harding piece was starting to poke out of his skimpy loin-cloth, and press into the crotch of my dress. I was scared his dick would feel my dick, and paniced at his possib'e reaction.

"Where you think you going sweetheart?" he asked, holding me tighter as I finally succeeded in breaking our kiss. "Don't you want to have some fun?" With his hand still on my ass, gripping it harder, Raymond's other hand reached up and started molesting my fake tities. "You so pretty." he said, obviously a tad drunk.

"Please...." I struggled and squirmed, losing my footing in thos size 10 pumps I was wearing. I stumbled out of Ray's arms, and onto the floor beneath me.

"You okay?" he asked from somewhere over top me.

"Yes." I whispered, still disquising my voice. I looked up, and saw Raymond's hard dick staring me straight in my face.

"You sure you alright?" he asked, moving in closer. His dick touched my nose. I tried to back up, to get it away from my face so I could get my barings and get out of there, but Raymond put his hand on the back of my head, and shoved his pelvis forward into my face. His dick head slapped onto my painted lips.

"Come on baby, suck it for me." he whispered in a low voice. He sounded desperate, but I knew I wasn't the one to help him out with his dilemma. I put my hands on his thighs, and tried to push him out of my way. Raymond grabbed the sides of my head, and forced his dick back into my face, the head actually pearced my open lips. It didn't take him long to start feeding me the shaft too.

(Huggggh} I gagged, trying to get it out.

"Come on baby, work that dick for me. Nobody will know." he said, as he sawed the hard wood in and out of my mouth. I couldn't believe I had a dick in my mouth. An actual dick. Some guys DICK. Raymond was moving his hips back and forth, and his meat was sliding along my tongue with them. Everytime he'd push his hips forward, his dick would be shoved into my mouth, and my lips would stretch wide around the shaft to make room in my mouth.

My mind was telling me I was crazy. Crazy to be in a wig and a dress, on my knees in my girlfriend's ex-boyfirend's house, sucking his dick upstairs at a party while noless then 50 party guests crowded around downstairs. Ray was shoving his meaty tool in and out of my mouth at a fair rate. I was taking half his dick into my stuffed mouth. I couldn't believe I was doig this. It had to be a combination of the alcohol I drank tonight, and the weed I smoked in the car on the drive over here with Darryl. Ain't noway I would have ever been caught dead in a situtaion like this under normal circumstansces.

"Ummmm....damn girl...." Raymond moaned, signaling that I was doing a good job on his dick. Strangely enough, hearing him moan his approval made me want to do a better job for him. I kind of figured, if I already had his hard dick in my mouth, why not give in to curiosity, and suck on it forreal. I know alot of men secretly wondered what its like to suck dick. At least I do. Or did. Or so I've read.

I looked up at Raymond's brawny body towering over top me. It was still dark, but my eyes were able to distinguish his flat wash board stomach, and his heathing chest through the darkness. He held his head back, and his eyes were closed, as he stood there fucking the face of the man he thought was a woman. Decisively, the anomaly of being a woman, gave me the anonymity I needed as a man to forfill my curosity to suck another mans penis. It was strange. If I hadn't come to this holloween party as a woman, I would never have had the opportunity to let my inhibitions out. As it was, there was noway for Raymond, or anyother party guess to know that the woman on her knees sucking dick was really me. A man. I started sucking Raymond's dick with heart and soul, and he noticed the difference immediately.

"Yeah. Yes. Thats it baby. Suck daddy's big dick for him." he cooed, stroking my tangled wig as I labored over his thick tool, sucking it as Ive always liked mine sucked. I tried taking Ray's long fat piece into my throat, taking it three quaters of the way into my mouth. I sucked greedily, like I hadn't tasted meat in days. Spit dripped from my lips and along his shaft, down the front of my dress, soaking my fake tits. Raymond "ooed" and ahhed" as I washed his dick in spit, and slurped up the saliva like milk shake.

"Damn girl, youre good." he said, trying to shove his dick into my throat. My eyes teared up, and began to streak down my face. I knew I wouldn't be able to get it all down on the first try. I'd need plenty of practice if I wanted to learn how to deepthroat correctly. That last though made me stop in my tracks, as I repeated it in my mind. Was I actually considering learning how to deepthroat? Was this a skill I needed to know? Was I planning on sucking any more dicks in the future?

Raymond's dick was still in my mouth while I was contemplating these thoughts, and didn't realize I had worked it up to such a frenzy. Ray groaned a rather loud moan, and then his dick started spitting thick burst after thick burst of hot pan cake battered cum into my mouth. I felt the dick hosing my mouth down, and tried to remove it from my mouth. Raymond placed his huge hands on my head, and pumped his hips so that his dick inched into the back of my mouth. A large wad of sperm shot out, and jetted its way straight down the back of my throat. I gagged on the clog, and when my throat opened, Raymond shoved forward. My windpipe closed instinctively around the invading muscule, and Raymond let loose about 4 or 5 more ropey strings of batter straight down the back of my throat into my stomach.

"Oooooooooooooo yeeeeeeeeeeah." he moaned, satisfied. He pulled his now spent penis from my throat, the wet head dragging across my tongue, leaving cum residue for my tastebuds. I swallowed what sticky goo was left in my mouth. My dick began to harden.

"Come on girl." he said, pulling me up to my feet. "I can't wait to taste your pussy."

'OH shit!' I thought to myself, realizing the jig was about to be up.

"Come on, I want to fuck you right now." he added, taking me by the hand and leading me into his master bedroom. Where the bright lights were.

I stopped. "Where's the ladies room?" I whispered with a smile.

"Right there." he said, pointing to the door across the hall. I didn't even look back, I went straight to the bathroom. When I noticed Raymond wasn't in the hall anymore, I quietly snuck out of the room, and down the stairs, out the door to freedom. Once outside, I high-tailed it down the street and around the corner and up the block before he could realize I was gone. I spent the rest of the night walking home, contemplating what just happened over and over in my head. I still couldn't believe I sucked another mans dick, and swallowed his cum. I couldn't believe I allowed myself to be put in that position. Why did I pretend to be a woman when he questioned me? Why didn't I just answer him in my "male" voice? I mean, were WERE at a costume party. Did I secretly want to suck Ray's dick? I thought he was attractive for a guy, but did that mean I was sexually attracted? Maybe it was just the curiosity taking over. The opporunity, the situation, and the circumstance. I mean, I KNOW I'm not gay, dispite what happened. Just because I sucked a guys dick, don't mean I'm homosexual. Does it? What was I then?

I got to Darryl's crib to shower and change clothes about 3 hours later. I had alot to think about. Darryl had alot of questions about why I walked all the way home, and why I didn't call him, and what happened at the party. Basically, I told him half the story to keep him from detecting the truth so I could get some much needed sleep. I told him I saw Yolanda and Raymond kiss, but that she told him off and walked out, and that I lost the purse and couldn't call. Ray seemed to buy that explaination, and didn't press too much further. The next morning, I had him drop me off at home, where I told Yolanda I forgot my key and had to spend the night out over Darr's. Yolanda kissed me full on the lips, and let me in. My dick started to harden as I felt her plump juicy ass under her jogging pants.

"No baby, don't. We have company." she said, jesturing towards the living room.

"Oh?" I said, looking at my watch. 'Who would be here at 9am on a saturday morning?' I wondered. To my surprise, there Raymond was, sitting on the couch with a big goofy grin on his handsome face.

"Good morning Karlon." he said, extending his hand to shake.

"g'morning." I replied back, half hearted.

"Raymond stopped by to think me for going to his party last night." Yolanda said, smiling.

"uh-huh." I said. 'More likely, to apolojize for trying to force his way on you, no doubt.' I thought to myself.

Just then, the telephone rang. "I'll be right back." Yolanda said, dashing across the room.

"So Karl, you couldn't make it to the party last night?" he asked, trying to make small talk.

"uh, no. Me and my buddy made plans." I said, trying to forget last night, and not look at his crotch.

"Oh. Too bad." he said, then he moved in closer. "Cause it was this chick there, that sucked my dick like a champion whore." he laughed. I laughed too. Had I not known who the "chick" was, I would have thought he was refering to Yolanda. Which I was sure, is what he WANTED me to think.

"Did you get her name?" I asked, knowing he didn't.

"No." he said, not surprisingly. "She snuck out on me before I could ask her."

"humm, shame." I said, uninterested.

"Funny thing though-" he added, peeking my interest. "-when I was cleaning up from the party this morning, I found a small purse on the floor of the room she sucked me in. I checked the purse to see who's it belonged to, and I found an old I.D of Yolanda's inside. And a cell phone with her name and number in it."

My heart stopped beating.

"Now, I remember when Yolanda came in, and she wasn't wearing a purse." I felt beads of sweat break out on my brow. "And when I put two and two together, I started to realize that the girl I let blow me last night had somewhat of a deep voice for a chick."

"So you think you let a guy suck you off last night?" I said, trying to de-rail this locomotive.

"Naw-" Ray said. "-not a guy, a faggot." he blunted, watching my reaction. "He was pretty good too, this faggot. I don't think that was his first time sucking dick. And I doubt seriously it'll be his last. He liked it too much."

"Oh? How you know?" I asked. Getting myself tangled up in his web.

"Cause he sucked it so good. He even took me deep into his throat. And, he swallowed All my juice too. I wish I knew who he was. I want to ask him how well did he like my nutt."

I blushed. Suddenly, a cell phone started to ring. Raymond reached into his jacket pocket, and pulled out Yolanda's small purse. He opened it, and pulled out my cell phone. "Yes?' he said into the receiver.

I stared wide-eyed as he paused, then gazed at me with a smirk. "Its for you." he said, handing me the phone.

Guess the jig is up.

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