Halloween with Sinnndy

It's been a while since I have found the time to write a story, so here is a small recap of what is happening in my life right now. I am 20, Billy and I are engaged to be married next Labor Day weekend and my girlfriend Jodi will probably marry Billy's brother Josh. Jodi and I still spend a lot of quality time in and out of the bedroom with each other. Josh started working for Billy a couple of months ago and is still learning the business. Both of them go out of town almost each week leaving Jodi and myself behind to fend for ourselves, so we do what comes naturally to both of us, we fool around and hang out together.

My kinky sex life has slowed down quite a bit since I became engaged, not for the fact that I am engaged, but I think it was just a progression of where I am headed in life. There was no way I could keep up the pace that I was at, and I lost another online Master. Our club on MSN started taking too much time from his life, so now we are looking for someone else to run the club. I'm actually happy for the slowdown, I can concentrate on my business more, and it is really booming. For those who haven't read my previous stories, I was a personal trainer at a health club and enjoyed working there, but they wanted to mess with my schedule expecting me to work more hours than I wanted to. Billy built me a gym in his basement so I took my good clients with me and started my own business working out of our basement. I love it, I can work as many or as few hours as I want to, and I don't have to worry about any commission.

Billy always has a Halloween party every year, and it is usually pretty wild. We decided to really go for a stretch with our costumes this year; I was going to dress as a slave and Billy as my Master. I was dressed in all leather, a tight vest and a short skirt, no panties of course, and I donned my collar with leash attached. Billy always has a scheme in mind for me, and I always love what he has planned. I was really curious as to what he had in store for me this year, most of the time; I have some idea, but not this year.

Billy and I always greet the guests as they first enter his house. There were the usual wild costumes, a lot of them BDSM related, slaves, Masters and a lot of leather. There was a lot of the regular Halloween wear, men dressed as women, women dressed as schoolgirls, ghosts and goblins. Most people really took the time to get their costumes together, we were quite pleased. We always have a great spread; Billy hires out a caterer who did an awesome job as always. We had huge pieces of shrimp, chicken wings, quesadilla's, and my favorite, sushi.

Billy and I started mingling with the guests, I ran over and gave Jodi a big kiss hello, she was dressed as a schoolgirl, her hair in pigtails, short plaid skirt, white shirt, she looked sexy. Billy and I then started talking to one of his business buddies, Peter who introduced us to his date, a stunning tall blonde named Tanya. She had long straight flowing hair, long lean legs, beautiful white teeth, nice firm "B" cup breasts and a great looking tush. She was also dressed as a slave, leather vest and short skirt, almost identical to my outfit except that she had knee high black boots.

Billy informed me that Tanya and I were going to be involved in a contest that evening. Peter had bragged to Billy that Tanya was the biggest slut he had ever seen and the best oral artist he had ever experienced, and that I was no match for her. Billy knows better, that while I hadn't been as sexually active as in the past, that nobody gives better head than I do, and no one is a bigger slut. It would be a simple contest in a best of three categories. The first category was to see how many people we could give oral homage to in a three-hour period. We would then give a card to the lucky person and tell them to give us a rating of 1 to 10, with 10 being the highest. There was a box in the front hall that they were to turn the ratings cards in to.

If we split the first two parts of the contest, then the third part would be for the two of us to try and get the other one off faster. I knew that Tanya would be stiff competition, no man or woman would say no to her. I hate women with long longs, it isn't fair. The contest was to start in 5 minutes, which would make it 9, and end at midnight. Billy and Peter were off limits as was Jodi for me; it had to be people that we weren't regular lovers with.

I didn't even have the advantage of knowing more people than Tanya because she knew almost as many people there that I did, but that was ok with me, it would be a fair contest and I love competition. It would also be nice to know whether I had lost a little of my touch, but I was confident of one thing, she might get more people to allow her to give head to, but my average rating would be higher than hers, I just knew that.

The contest had begun, so I started checking out the crowd to see who would make good candidates. I saw three of Billy's basketball buddies chatting together and walked over to say hi. All three are black and in wonderful shape, James, Ronnie and Horse. If you read any of my past stories, Horse is nicknamed that because he has a 14" dick. One of the rules of the contest was that at first, we couldn't tell the men or women that it was a contest, if we did, there was a section on the card that would give it away if we didn't play fair. I just came out and told the guys that I was horny and thirsty for their man juice. Most men would probably be shocked, but the three of them knew me quite well, so off we went to my bedroom.

I told the guys that I was having my period, so I could only give them head. They had no problem with that of course; after all, they were men. I had them drop their pants, Ronnie and James were about 8" each, James a bit thicker than Ronnie, and of course Horse is just massive. I started sucking on James' cock while stroking the other two. I took turns sucking their cocks and stroking them as I really didn't have a lot of time to spare, but I also wanted it to be good for all of them. I started to alternately deep throat Ronnie and James, I would take one of them all the way into my throat and teasingly go up slowly while slithering my tongue on their hard cocks, then I would do the same to the other one. I always kept two in my hands; this really helped get them off quicker. I decided that James would be first, so I really started working on him, sucking him all the way up and down. I released my grip on Horse; I had plans for him after I was done with the other two. I used my free hand to stroke James while I sucked and bobbed my head up and down and was rewarded with a nice creamy deposit straight down my throat. I then went to work on Ronnie, using one hand to stoke his cock firmly while moving my head up and down on his cock and sucking him like a Hoover. He didn't last too long, but pulled out and shot his load all over my face, which I found to be a waste. I then explained to them about filling out the cards and where to deposit them and dismissed the two of them kindly; I had other ideas for Horse.

I knew this was a contest, but I wasn't going to waste being around his massive manhood, and I had Billy's ok to play. I had two goals in mind, one, to give him head for the contest, and two, to get his monster all the way inside of me. I slowly teased and swirled my tongue around his cock, completely coating in with my saliva as my fingernails tickled his testicles. I was driving him nuts, I looked at his face, his eyes were closed and he had a huge smile on his face. Horse is a sweet gentle mountain of a man at around 6-8 and over 300 pounds. He had always had women problems because let's face it, most women would freak whenever they saw his cock.

I knew I had to get this over a bit quicker than I really wanted, so I started pumping his cock firmly with one hand and sucked as much of his head that I could fit into my mouth. I also would suck on his shaft and really quickened my stroking. Horse was close to cumming, being the nice guy that he is, he tried to pull away, but I wouldn't let him. I stroked his cock firmly and placed my mouth over his head, awaiting my creamy dessert. I wasn't disappointed as he shot a monster load into my mouth. I swirled it around on my tongue showing Horse his load on my tongue, and then swallowed and opened my mouth showing him that I did just that.

I kept stroking and licking his cock, I wanted him hard for me now. He went limp for a while, but I started talking dirty to him telling him how much I need his big cock and how badly I wanted his cream shot up high inside of my pussy. It didn't take long for him to get hard again, and when he was, I playfully pushed him down on the bed. I was really wet and extremely hot and horny, this man had the perfect cock and I was going to milk it dry. His massive head went in with a pop, and I slowly slid down on the first 7" of his cock. Men have told me how good it feels to have a woman slowly drop down on their cocks, and I could tell that was true by the smile on Horse's face. I slowly lifted my body, and then went back just as slow on the way down. Each time I went down, I could feel him going deeper inside of me, if I could guess, I would have said that I had about 10" inside of me. I felt so full at that point and decided to start riding him a little faster, that way more and more would go inside of me naturally and I wouldn't have to concentrate so hard on taking the whole thing.

So ride I did and while riding, I grabbed Horse's hands and placed them on my hips, urging him to pull me down on my downward thrusts. I usually don't cum while fucking, but I felt an orgasm coming on. On one downward thrust I went down as hard as I could, and I was there, Mount Everest, his entire cock filling my hot little pussy. I saw stars, there was intense pain at first, and then a wonderful warm rush in my loins as an intense orgasm swept through my body. I was in a wonderful place in time, completely filled and one of God's gifts to women causing my body to shudder and shake.

We stayed that way for a little while until I could catch my breath, it was quite an intense feeling and as it subsided, I had Horse roll over while still buried inside of me until I was on my back. I then laid back and let him do the work. No woman had ever taken his whole cock in their pussy before and knowing me well, he started pounding me hard, slamming his 300 plus pound body into me. I loved every second of his pounding, and I started giving him some dirty talk to keep him going hard. I then placed my legs around his shoulders giving him even deeper access and adding to the pleasure of his huge tool slamming in and out of my hungry pussy. I could feel his big balls slapping against my butt cheeks, so I reached underneath to playfully claw at his balls with my fingernails. He was really pumping me hard, and I could see he wasn't going to last too much longer, so I placed my finger in my mouth to moisten it, and slid it into his asshole. His eyes opened wide, he then grunted and started shooting a massive dose of cum into the deepest depths of my pussy, and then he collapsed on top of me, his cock completely buried inside of me.

We got cleaned up and I gave him a big kiss explaining to him that I had some catching up to do in the contest. I decided that I had to work fast, so I scanned the crowd for single men and spotted a couple of guys chatting away. I walked right up and introduced myself, their names were Rich and Marty, two business associates of Billy and newcomers to one of Billy's parties. After a little chitchat, I told both men that I was a cum slut and needed to suck them off. They were taken aback by my straight forwardness, but of course, they were men, so getting them to play along was easy.

I took Marty, a 40ish gray haired man in the bathroom and quickly pulled his pants down and took his hardening cock in my hand, then steering it into my mouth. He had an average sized cock, around 6" and I deep throated it quite easily. That brought a shocked sigh from Marty, after all, most women cannot deep throat most men, they are either afraid or don't know how to work past the gag reflex like I can. It was now time for business, no time to fool around, so I licked his cock all over to get him nice and hard. I then started sucking him all the way down my throat and on the way out; I gave him a good solid stroke with one hand while fondling his balls with the other hand. Marty was in heaven, his eyes were shut and he had that "damn, this feels great" look on his face. Marty didn't last too long; most men can't when I put my mind to it and really concentrate on getting them off. He pulled away and shot a huge load all over my face and breasts. I then told him about the contest and handed him the rating card. I cleaned up and went out to repeat the same procedure to Rich, who like Marty, had a nice average cock and really enjoyed my performance.

I picked out men very carefully as I didn't want any wives ticked off at me, unless they were swinging friends, that way I knew it was cool with the ladies. It was getting close to the bewitching hour, I had about 30 minutes to go and the male candidates were dwindling. I scanned the people at the party and went from room to room until I spotted the perfect candidates. There were three stunning women from Jodi's exotic dance club that I knew pretty well, knowing also that they were bi-sexual. I walked up to the three hotties; there was Gina, a dark haired and skinned Italian woman. She was in her mid 20's, about 5-6 and approximately 110 pounds. Jenny was a shorthaired blonde, 5-8, about 120 pounds with huge, but fake breasts, I prefer mine real. Jessie was also a brunette, but she was a tall curvaceous Amazon type without an ounce of fat on her, you could bounce a quarter off of her abs.

I told the three of them that I wanted to try a new technique out on Jodi, but that I wanted to test it first and asked if they would help out. They had been at the party and were very loose by this time; they were dressed as the Powerpuff girls, Bubbles, Blossom and Buttercup. They were pretty game so I led them into my bedroom and helped them undress, which was a real pleasure. It was like a dream scene, four hot, sexy, horny and naked women in my bedroom, I had to pinch myself to believe that it was really happening. I had them lay next to each other and decided to start from left to right. I really didn't have time for a lot of foreplay, but I knew I had to warm them up. I started with Gina first; she was mostly shaven with her pubic hair trimmed like a little heart.

We started kissing, lightly at first, tongues swirling in each other’s mouths as my hands wandered to touch her breasts and quickly worked their way down to her moist pussy. I dipped my index finger in and bought it to her lips. She sucked on my finger like it was a cock as I slid two fingers from my other hand deep inside of her and started twirling them in a washing machine motion, back and forth. Meanwhile, Jenny and Jessie decided to start their foreplay without me, which was cool since they would be nicely warmed up by the time I got to them.

I kissed my way down Gina's toned body and went to work licking her pussy, sucking on her outer lips while working on her G-spot with my fingers. I lightly licked her clit, which sent shivers throughout her body. I ignored her clit for another minute, paying attention to the rest of her pussy, and then her hands went on top of my head pushing me closer to her, signaling to me that she wanted me to make her cum. I started in on her clit, licking in circles and up and down, gently sucking and nipping at it until I found the right combination, which drove her wild. Her legs were thrashing around as she pushed me in even closer while moaning loudly, that turned me on. I continued my assault on her G-spot with my fingers and her clit with my tongue and mouth until she started screaming and bucking, telling me and whoever else was in Lake County that she was cumming.

Gina finally calmed down and I went straight to work on Jenny's pussy, no teasing, right to her clit as my fingers searched for her G-spot. Jenny was quite ready for me; she was wet and had the same heart shaped pubic hair as Gina did. Jenny was very sensitive to my touch, like she would jump out of her skin every time I tried a new technique. I worked fast and when I sucked her clit into my mouth, she put both hands on my head and actually shot a creamy and tasty deposit into my waiting mouth.

I looked over at Jessie; she had big beautiful hazel eyes, which were lustfully glancing at me. She could tell by the way that her friends had just cum that she was in for a treat, and I didn't let her down. She was a real moaner and a dirty talker, urging me on by calling me her slut and a little whore. She had a bit of Dominance in her, and of course, I liked that. She told me what to do, when to slow down and when to speed up, she wanted to control me and I believe by my body language that she knew I was a submissive. She grabbed my hair with both hands and pulled it up and down as I tongued and sucked on her clit while fucking her pussy with two and then three fingers. I stuck a fourth in, and before I knew it, my fist was in her and I was pushing it in a couple of inches past my wrist. She was really bucking and moaning, pulling my hair, telling me to go deeper and deeper. I didn't want to hurt her, so I pushed in a little deeper and started twisting my hand. I then sucked her clit into my mouth and licked it with the tip of my tongue, which brought her to a hard and long climax.

I then explained the contest and the rules to them, telling them that I hoped they weren't mad because I kind of used them. They weren't mad, in fact, all three of them wanted to get me in bed, but respected my relationship with Jodi, so they left me alone. Before I left the room, Jessie came up to me and told me that she hoped we could play again sometime, and I told her that it would definitely happen and that we would talk later.

It was now midnight, Billy and Peter went into a room to tally up the scorecards and came out after about 10 minutes while about 20 onlookers watched and waited. Neither one of us had any idea who was the winner, or if the tiebreaker would be necessary. Peter announced that by a score of 25 to 23, and an average of 9.5 to 8.5, that I was the winner. I jumped up and gave first Peter, then Billy a big kiss. I then went over to Tanya, shook her hand and gave her a big hug. We looked into each other's and went into a deep, sloppy kiss. We were both competitors and wanted to see who could get the other one off first and to pleasure each other, there was definitely mutual attraction.

Tanya had not paid oral homage to a woman yet that evening, so I really had the upper hand. I pushed her onto her back on a couch and placed myself so I was looking face down at her bare pussy. I dove right in licking her pussy all over while grinding my also bare pussy into her face. I found out later that she had not been with a lot of women, but I wouldn't have guessed that because she ate me like a pro. She followed a lot of what I was doing. While I was searching for her G-spot, she followed suit. When I licked her in circles she did the same; she was smart and a natural. She couldn't keep up with me however as I was always a step ahead of her, and when I stuck a finger into her ass and sucked her clit into my mouth, she moaned, bucked and came hard, squeezing her thighs around my head as she screamed out loud that she was cumming.

I gently licked and slurped at her pussy as she went back to her assault on my pussy, and like her teacher, she stuck her finger in my ass and sucked my clit into her mouth, causing me to shake and moan, bringing me to another wonderful orgasm.