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My Best Halloween

Category: Group Sex
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Halloween is a great time of year. Grown-ups get to play dress up, and more importantly get to wear masks. I don’t know what it is about masks, but inhibitions seem to disappear when the masks go on.

Last Halloween, I was invited to a neighbor’s costume party. I could hardly wait, but it was a busy time for me. Party night came, and I hadn’t even thought about a costume.

Not deterred, I remembered all the last minute costumes I had ever rushed to invent, pirate, hobo, recovering alcoholic (ok, I just came in my regular clothes), and then I remember that film classic, “Animal House”. “Toga”, “Toga”, “Toga”. Nothing says Halloween like near nudity!

I stopped after work to pick up a mask. I just grabbed a basic mask in black. At home, I pulled out an old white sheet and an old tie. The big debate followed, underwear or commando? Not wishing to be shunned by the neighborhood and not knowing the neighbors that well, I wimped out. At least I picked black bikini briefs. Maybe a little scandal wouldn’t hurt.

I wrapped the sheet around me, dr*ped it over my shoulder and tied it at my waist with the tie, the hem at mid-thigh. I put on the mask and checked myself out. “Not bad,” I thought, “Skin without obscenity.” The outfit screamed “Party”. I grabbed a couple of wine bottles for the host and headed down the street

The outside of the party house had the right amount of spooky lights, fake cobwebs and foam tombstones. The doorbell chimed a creepy tune and the person who answered the door was the obligatory Dracula in cape and fangs. I was ushered in and introduced by first name to many other first names. Some were neighbors, some were unknown to me, and some didn’t remove their masks, so I still don’t know. I grabbed a drink and wandered into the room with the blaring music, black light and dancers.

I stood on the side watching the crowd bounce to the music . . . and I mean bounce. These guys were wearing the costumes that made Halloween so popular with me; kitty cats (or is that pussy cats) in black tights with very low necklines barely containing a variety of lovely breasts, a couple of French maids with legs all the way up (Oui! Oui!), several in bondage attire with varying degrees of coverage, guys in leather wear, guys in drag, and even a girl in gangster drag.

I like my neighbors.

A petite young lady in Elvira attire (but a short, short skirt), long black hair and a red mask stepped up beside me and handed me a tequila shot. She downed one of her own and motioned for me to do the same. A gentleman always obliges. She reached up and placed a slice of lime between my lips. Her hand and forearm continued to rest on my chest as she turned to watch the dancers.

I tried discreetly to figure out who this lovely lady was. She was only about 5’2” and I am 6’, and as I peeked down at her, I got view of a beautiful swell of breast in the plunging neckline of her costume. She caught me looking. She smiled and shifted to give me a better view. She was a nice C cup with big round and brown nipples. I wanted to bend down and suck them right there

She pulled me down and cupped her mouth to speak in my ear. “Here alone?” she asked. I nodded.

“I’m Nina, I came with friends”, she said, and then “I like your costume. It’s easy access.”

Not certain what she said, I gave her a quizzical look. Then I felt her hand slide up my thigh to my ass.

“You’re going to have to lose these,” she said.

I think I blushed, but I definitely nodded yes. I guess a lady always obliges, too, because her hand slipped into the waistband and began to pull my briefs down.

Alarmed, I looked around to see who was watching. I realized all eyes were on the dance floor, and we were in the shadows at the edge of the room. I slid my legs apart and let the under wear drop to the floor. She smiled. “That’s better,” she said, and caressed my ass.

I downed the remainder of my drink (the first one) and set the glass on the shelf behind me. I put my arm around her, and we turned slightly to get a better look at each other. Her hand never left my ass. My dick was at full attention and making a tent in my toga. She looked down and then pulled me to her. My cock was pressing into her firm and flat midsection. “Ah,” she said, “That’s the reaction I was looking for.”

She took her hand from my ass and grabbed my cock. Her hand was small but her grip was firm. She stroked from belly to crown. “Nice” she said, “I like your size, big enough to make me squeal, but not too big.”

I swallowed hard and mumbled something. I think I said “thank you.”

Nina tugged at my cock and said “Follow me.” I looked at her with fright in my eyes. I thought she was going to drag me through the room by my dick.

She must have understood, because she laughed, and with a twinkle in her eye, let go of my erection and grabbed my hand. She walked me across the room and into a hallway. I watched her ass closely as she pulled me along. Her dress barely covered her, and I wished it didn’t. Her ass was a perfect little heart shape under the material and it looked so inviting. Her legs were tanned and firm and covered with black spiderweb fishnets and apparently a black garter belt.

We wandered into the master bedroom and then into the bath. Nina pushed me against the wall and dropped to her knees. She lifted my toga and grabbed my cock. She licked the tip of my cock with the tip of her tongue. She ran her tongue around the base of the head, and then down the shaft to her hand. She sucked the head into her mouth and stroked with her hand. Her other hand grabbed my ass, her fingers in the crack and brushing the rim of my asshole.

I reached down and caressed her hair. She grabbed my ass with both hands and dove on my cock. Her head bobbed. It was incredible. She took me deep and then slowly back out to suck on the head of my cock. I couldn’t help it; I was bucking and thrusting into her mouth. She squeezed my ass hard. Then she buried her middle finger in my asshole. I jerked away in surprise and my cock jumped. She pulled me back and took me all. My balls were against her chin and my cock was down her throat. Her tonguing and finger-fucking were too much. My cock got even harder and rigid. I gurgled, “Oh, God.” I heard Elvira moan as I started to cum and cum and cum. I swear she sucked me dry, and as I started to go limp, she stood up.

She looked up in my face and smiled, cum dribbling at the edge of her mouth. She stood up and pulled me close to kiss her. Her tongue darted into my mouth, and she left a huge load of my own cum. In surprise, I swallowed and gulped. She laughed and started kissing me again. She jumped back and said, “My turn.”

She hopped up on the edge of the vanity and lifted her dress. She was not wearing underwear. I was staring. She was neatly trimmed and the dark triangle was inviting me in. I could see her clit poking from her pussy lips. It was large and firm and insistent.

“Well?” she said.

I was immediately on my knees. I spread her legs gently.

“You don’t have to treat me like a porcelain doll,” she murmured. “I like it a little rough.”

I attacked her clit with my tongue, and this time not so gently. She moaned and hissed, “yesss…”

I licked her clit and then the outside lips of her pussy. I pushed the tip inside her lips and she was very wet and slick. I drove my tongue in as far as it would go and sucked at her whole pussy. Her taste and smell were intoxicating. I fucked her with my tongue. After a bit, I put my hand in the crack of her ass with my thumb at the back of her pussy, rubbing from her ass to pussy. I pressed my thumb into her pussy and she shuddered and groaned. I sucked at her clit and grazed it with my teeth as I fucked her with my thumb.

About that time I heard a knock and a man said “Holly?” as he opened the door. Nina squeezed my head with her thighs and held it in place with her hands. “Not now, Sam!” she replied in consternation.

“But we want to go to the other party now,” Sam whined.

“If I can bring him with me,” Nina pouted, and Sam assented.

I heard him leave and Nina pulled me up by my ears and kissed my pussy-wet face. She looked in my eyes and stated without question, “You are coming with me!”

I nodded dumbly. No way was I going to be anywhere else.

We slipped out quietly and hopped in the back seat of a black Mercedes parked halfway down the block. Three others got in with us. All of them kept on their masks, but it was clear that they were all young and fit . . . and not overdressed. The costumes included the lady in gangster drag I had noted earlier, and two escapees from the Rocky Horror Picture show, including Sam as the Transylvanian transvestite. They were murmuring in hushed tones, and with an air of anticipation.

Nina was between me and the gangster girl, a strawberry blond who was finding it hard to conceal her rather large chest beneath her pinstriped, double-breasted suit (no pun unintended). Nina was running her hand along the inside of my thighs. I was getting excited again but the movement made me remember my underwear. I couldn’t help but wonder who would find them lying on the floor.

Nina’s movement was lifting my toga and airing my stiffening member. I surreptitiously glanced at gangster girl and she was watching my groin with interest. Ok, I couldn’t tell what she thought but I hoped it was interest. I started to cover myself, but Nina pushed my hand away. “Ah, ah, ah”, she whispered, “I want you ready for the party.”

I didn’t know what that meant, but the party was sounding good. I looked at gangster girl. I was surprised to see that she had opened her shirt and was fondling one large and lovely breast. She was rolling the long pink nipple between her fingers. Nina was caressing my balls as my dick stood at attention. “You look ready,” she whispered, “I think I’ll help Holly get ready.” With that, she turned and took Holly’s tit in her mouth. Holly laid back and smiled. She pulled her arm free and slipped it across Nina’s back. She lifted Holly’s skirt, and slid her fingers between Holly’s butt cheeks. Nina moaned, and I did, too.

The girl in the front seat turned back to watch. She looked at me and winked. She reached back and patted my knee, deliberately brushing my cock with her hand before turning back to the front. She had her arm around Sam. She bent over and began kissing Sam’s neck, her hand obviously massaging his thigh..

Nina was grinding her ass into Holly’s hand and my thigh. “What the hell,” I thought and reached in to caress Nina’s breasts. Nina had unzipped Holly’s trousers and pulled them to her knees. Nina was rubbing Holly’s clit with her palm and finger-fucking her deeply from the looks of it. Holly began to whimper, “Oh God, oh God, oh God, oh God.” Her back was arching and she was humping Nina’s hand. I was afraid that I was going to cum, too.

Holly slumped and moaned. Nina kissed her slowly on her lips. Nina licked her finger, turned to me and kissed me. Then she pressed her fingers into my mouth. They tasted good. I sucked them, and Nina moved them slowly in and out of my mouth. “You’d be a pretty good cocksucker,” she grinned. I stopped licking, and she laughed.

I hadn’t been watching as we drove, but we were in a rural neighborhood with big homes on secluded lots. The car pulled down a long drive and behind several nice cars. We all piled out and headed for the front door.

The group rang the doorbell and yelled, “Trick or treat!”

The door opened to a dark room, and a tall gentleman in a cape and black mask stepped into the light. “Velcome,” he hissed through fanged teeth, “Come in.” Nina caught me staring and whispered, “They’re caps.” Dracula spread his arm an cape, inviting us in. He was naked under the cape, and impressively so.

We stepped inside, and let our eyes adjust. There were several other people inside, and momentarily, it became obvious that they were all naked except for masks and odd costume bits.

“Please make yourselves comfortable,” vamped our host, “You’re right on time.” He pointed to a door just inside the near hallway, and the group headed in that direction.

I spied piles of clothes and costumes along the hallway. By the time I got into the room, the rest of the group was half undressed, and that caused me to pause. Nina grabbed my waist and yanked the sash free. With her other hand, she pulled the sheet from the rest of me. “Better,” she said, loudly enough so that the others looked up.

My cock had reacted immediately to Nina’s rough treatment. “Nice,” I heard in tandem from the nearly-naked Transylvanian rock stars. I notice that Sam had jumped to attention as well. His friend introduced herself as Janie, and Sam formally introduced himself as well. I wasn’t sure if I should shake hands or something else.

Nina’s Elvira dress was open to the waist already. She undid a couple of clasps, pulled it open in the front and it dropped to her feet. Her body was petite and beautiful. She grabbed me –my hand this time – and said “Come on!” Nina, now naked except for garter belt and stokings, grabbed my other hand.

I followed them into the party, feeling self-conscious, but really excited – in every way. Sam, behind us, said, “Play room!” Holly and Nina nodded and turned the other direction down the hall to stairs going down. We descended into a large, dim walk-out basement that seemed designed just for this party.

There were a couple of contraptions I took to be sex swings. I deduced this from the fact that one was occupied by a voluptuous redhead lying back in a sling with her legs in the air and a head in her crotch. Her friend had his mask pulled up to the top of his head, which made it look like he was facing upward, but the action indicated otherwise. She was tugging at his ears and moaning loudly.

Holly and Nina led our party to the center of the room, an old-fashioned “conversation pit”. There was not much conversation going on. The pit was filled with a huge round mattress at least twice the size of any I had seen before. There were two couples fully intertwined on one side. I noticed that the men’s masks were still in place. There were legs and arms everywhere. It looked like the two women were in a tight sixty-nine and the guys were fucking them in their asses, but it was hard to tell.

We all dived on the mattresses near them. One of the guys looked up and smiled before returning his attention to his friends. Holly and Nina immediately went into a sixty-nine. Sam looked at me and said, “Join us.” Janie nodded.

I got my first good look at Janie and Sam. Janie was a sparkling, petite redhead, with ample breasts and very pink nipples. Sam was also about 6’, average build, and he had a good-sized hardon. I was surprised that my cock seemed to react equally to both, and very favorably. I was too far gone. I hoarsely said, “Sure!”

Janie pressed me on my back next to Nina and Holly. Their naked bodies were moving rhythmically. Janie moved between my legs and rubbed her palms from my waist to my nipples, and lowered her mouth to my cock. She took the head lightly in her lips and ran her tongue up my shaft. Sam slipped behind Janie. He put a hand on her back and one between her legs. I think we both moaned at the same time. Janie held the base of my cock in one hand, my balls in the other and sucked vigorously at the head. She was stroking me as she sucked. Her stroking stopped at intervals, apparently as Sam hit the right spots.

After a bit, Janie sat up and turned around. I glanced over and saw that Holly was on her back, and Nina’s head was buried between Holly’s legs. Holly was thrusting against Nina’s face. Before I could see more, Janie crossed her leg across my head and lowered her wet pussy to my tongue. She promptly returned to sucking my cock. I was buried deep in her pussy. It was wet and sweet. Her pussy was framed by a full bush of dark red. I drew my tongue along the inner lips and flicked her clit. I held her ass with one hands, the other squeezing a soft, round melon of a breast..

Janis and I were both enjoying our ministrations to the exclusion of everything going on around us. I remembered the others when I felt Sam’s hand slide between us to grab Janie’s other breast. I could feel him kneading her breast and tweaking her nipple. Then, unexpectedly, he moved his hand and tweaked my nipple between his thumb and forefinger. My cock jumped, and Janie noticed, stroking me more rapidly. She moved her hand from my balls and began to tease my asshole. I was enjoying this immensely when I noticed another hand stroking my balls. It was large and a little rough, but it felt good. I realized it was Sam, and I was a little freaked but no way was I going to stop Janie’s fantastic work or leave her delicious pussy.

Janie never stopped sucking, but Sam’s hand moved up to replace her hand on my cock. His hand covered more of my cock but he stroked firmly and with a soft twist, and Janie matched his movements with her lips and tongue. It felt really good. Janie moved and Sam replaced her mouth with his. Janie’s pussy never left my face. I didn’t know what to do, so I kept doing what I was doing, flicking my tongue on her clit and dragging it in the folds of her pussy.

Sam was really good on my cock, dragging his tongue around the head and sucking it deeper and deeper into his mouth until I felt his chin against my balls. By this time he had both hands on my ass, pulling me into his throat. His head bobbed up and down. His finger massaged my asshole. I began to arch my back. I knew I was going to cum, but I couldn’t say anything. Janie was now fingering her clit as I tongue-fucked her and sucked her pussy lips. She must have known I was close to cumming, because she began to rub against me hard and fast. Her finger joined my tongue, jabbing in and out of her pussy. Sam also must have known I was close to cumming because his head began to bob more rapidly and he sucked hard. Just as I was about to cum, Sam forced a finger into my asshole. That sent me over the edge, and I pushed hard down his throat and shot load after load. He took it all. Janie, too, began to buck and moan and her juices were running down my face. I finally slumped and Janie slumped across my chest. I felt two tongues licking my softening cock and even my asshole, causing my softening cock to jerk in pleasure.

Janie rolled off, and it was then that I saw Holly sitting up with Nina leaning against her. When I looked at them they clapped appreciatively. “Nice. Very nice,” Holly said.

Nina asked, “Are we going to see another cocksucker in action?” I mumbled incoherently.

Sam looked at Nina and said, “It is my turn.” She smiled and crawled toward him. She pushed him back and started sucking his cock. She leaned back for a moment and asked, “If you get what you want, do I get what I want?”

Sam smiled knowingly and said, “Of course.”

Nina climbed up and mounted Sam. Her taut body was small against him, but she took him all, slowly and deliberately. She moved up and down on his cock. Her tits, with those beautiful, big, brown areoles and long hard nipples, rocked in time to her motions. I was getting hard again watching. Holly moved behind Janie and began to softly stroke Janie’s breasts with special attention to her pink nipples. Neither of them removed their eyes from Nina and Sam. I began to stroke my hardening cock. Janie put her hand over mine and stroked with me.

“I’m cumming,” Sam said. Nina pulled off and grabbed Sam’s cock, aiming it to shoot on her tits. It was the first time I ever saw another guy cum. He must have shot seven or eight times, and cum was dripping from Holly’s nipples. She pulled Sam up, and he licked his cum from her left tit. Nina motioned for us, and Janie and Holly moved to her right nipple, licking together. Janie still had my hand and pulled me with them. Nina reached out and pulled me to her for a kiss. Then she pushed my head between Sam’s and Janie’s, and then between her breasts. I had my first taste of cum. Well, I had tasted my own to satisfy my curiosity, but this was different. It was another man’s cum. I lapped up my share and joined Janie and Holly on the same nipple.

Nina pushed Sam back and playfully said, “Toy time!” She ran to a corner of the room, opened a chest and returned with several items in her hands. When she dropped them on the mattress, I noticed a big bottle of lube, couple of dildos – one large, one average, and a couple of harnesses. I couldn’t quite get my mind around the scene.

Nina grabbed a harness and the large dildo and slipped them on. She had to tighten the harness a lot to fit her slim body. Nina nodded to Janie and said get him ready. I looked startled and the girls laughed. Even Sam smiled. He was still on his back and Holly suck his soft cock as she rubbed lube in his asshole, eventually slipping in one and then two fingers. Sam got hard with all this attention. Nina said, “Here I come.”

She moved between Sam’s legs. Holly pulled a foam wedge-shaped pillow from across the mattress and slid it under Sam’s ass, raising it several inches. Nina grabbed Sam’s legs and pulled him towards her until the dildo was pressing against Sam’s asshole. She pressed harder until the tip was inside. Sam arched his back and neck, his eyes closed and he gasped. “Yes,” he hissed, “More”

Nina pulled back slightly, Sam following to keep the dildo in his ass. Nina pressed back and slipped halfway in. Sam groaned and writhed. The dildo looked huge, but Sam was pressing against it, wanting more. Nina thrust again and it was all in him. Sam began to rock against it, fucking it as Nina fucked him. This was too much for me. I was as hard as a rock. Holly continued to stroke Sam’s cock and Janie was stroking Nina’s ass. I leaned forward and took the head of Sam’s cock in my mouth. I couldn’t believe I was doing it, but it looked so good. Sam moaned and pushed against my mouth. “That’s my boy,” said Nina, stroking the back of my head.

Holly removed her hand and I took a mouthful of Sam. It was so different. His cock was as big as a corndog, but right now it tasted so much better. I could taste precum mixed with the remnants of cum. I circled the head of his cock with my tongue and licked from the base to the head along the vein on the bottom. I pressed my tongue in the tiny opening at the end. I sucked it in as far as I could and took the rest in one hand and his balls in the other. My cock was jumping.

All this time, Nina continued to pump his ass. Sam moaned and grunted and shook his head slowly from side to side. He began to tense and grunted, “Cumming.” He filled my mouth as Nina pounded his ass hard. I couldn’t swallow it all. Cum dripped from my mouth and down my chin. I sucked hard and long to suck him dry. Nina laughed, “Told you, you’d be a good cocksucker. That deserves a reward.”

I was still on all fours, and I felt hands on my ass and balls and cock. I was being lubed generously. I knew what was coming, and I didn’t resist. Holly put a lubed finger in my ass as Janie stroked my cock. I felt something cold and hard against my asshole. I looked back to see Holly in the other strap-on with the smaller dildo. She pressed into me, and I felt a burning pain. It hurt some, but it felt too good to stop her. I pushed back, taking more in me. “Attaboy,” crooned Nina. She leaned beside me and kissed me. She still wore the dildo.

Janie lay down in front of me and Nina climbed between her legs. Nina began to fuck Janie and they both had their eyes on me. Holly pushed all the way in me. Her pubic hairs tickled my ass. She started to pump my ass and it felt so good. I grunted and rocked with her movements. I felt Sam’s hand on my cock, gently stroking as Holly pumped me.

Nina pulled out of Janie, telling Holly to switch. She lubed her already glistening dildo and pushed it against my ass. It was much bigger, but she pushed it in. I dropped my head to the mattress and groaned loudly. Nina filled me completely. I thought she was going to split me in two. She started slowly, but pumped harder and faster. Sam continued to stroke me, and in no time, I exploded, shooting the biggest load I could remember. I was still spasming as Nina pulled out. I moaned, “Not yet”

Nina said not to worry. I felt pressure against my ass again, sliding in deep in one motion. I thought it must be Holly because it wasn’t so big. I opened my eyes, but Holly was still fucking Janie in front of me. Slowly, I realized that Sam was fucking me. I was definitely freaked, but it felt so good. My cock jumped to attention again. I had never reacted this often or this quickly.

His cock was softer than the dildo and warm and throbbing. He fucked me slowly and gently. His hands were on my waist, pulling me against him as he thrust in me. Nina slipped her head under my stomach and gently sucked my cock. I rocked back against Sam in time with his fucking. His strokes got faster and I could feel his cock swell and throb. My cock responded with his and Nina sucked me deep in her throat, dragging her teeth along the base. Sam cried, “Ahhh,” and jabbed his cock deep in my ass. I could feel his hot cum shooting in me. I don’t know where it all came from, but he filled me until I could feel it dripping from my ass. I started to cum again and Nina took it all. I could hear Janie screaming, “Oh God! Oh God!”

Nina pulled out from under me, and kissed me with cum covered lips. Sam lay down on my back as I slid flat on the mattress, His cock, softer, never left my ass. He reached under me and slowly stroked my soft cock. Nina lay down beside us and continued to kiss me. Shortly thereafter Janie lay down on the other side and Holly snuggled up against Nina.

Nina smiled and whispered, “We girls aren’’t through.” Then she slid her mask back down on her face.

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