The Bet

My name is Cole Bryant and the story I'm about to recount for you is my first three way.

I was in the family room of a good friend of mine named Tyson. We were playing Rock band on his playstation 3 and having an all around good time. When the conversation turned to sex, as it most often did. One of the avatars on our band was a rock chick; Tyson and I were making nasty jokes about how if we were a real band how we would be fucking any and all female band mates rotten. Tyson said I would be to afraid to have a three way with a girl and another guy, said I was all talk and no action.

"Wanna bet?" I said getting a little angry; to tell you the truth I'm surprised I'm not dead with how quickly I jump into situations with out thinking.

"Sure!" he replied. "What's the wager?"

"I don't know how about a flat of beer, winners choice."

"Fine but how are you going to prove you did the deed?" Tyson asked, now really getting into the bet. I thought about it for a moment then it hit me, my closet doors have slats that a person can see out but it's next to impossible to see into the closet. Provided he was very quite it should prove to be a good viewing spot. I told this to Tyson and he gave a laugh. "You really want to go through with this?" he asked mockingly.

"Fuck ya I'm secure in my sexuality, in fact the only problem I see is finding the couple!" I said confidently.

"No problem!" Tyson said with a wave of his hand. "I've got the perfect couple in mind!"

"Is she good looking and disease free?" I asked not believing my friend. After all it's not like couples normally make it common knowledge that they're looking for a third person to bring to bed. "Who?"

"My aunt Sara and her husband James! They're always going on about how they swing and like three ways and shit like that. You've met them she's a fox!"

"Are you sure it wasn't just talk?" although it was true she was very good looking in fact I had masturbated thinking of her a few times, I still didn't believe that he could deliver.

"Tell you what! If I can't at least get them to talk to you about it I'll buy you the beer of your choice!"

"You're that sure they'll go for it?" I asked amazed at his confidence.

"Yes I'm sure! But I'm even more sure that when they say yes you'll back out like the pussy I know you are!" he laughed. I told him he was on. Then we went back to the rock band.

It was a week later when I got a call from Tyson telling me to meet him at local coffee shop. I met him at the specified time, I sat down and ordered a coffee.

"Ok they want to talk to you about it!" Tyson recalled the conversation he had with them, and how they were excited at the thought of it. He told me that Sara remembered me to be a good-looking guy and a nice guy! Then he said it. "But we have a problem! They want it to be at a hotel or they're house they won't do this at your apartment!" he continued. I had mixed feelings about this, but I looked disappointed. Then Tyson went on "But I figure since I'm already in the loop this much I think they'll tell me that you chickened out. Or if by some miracle that you do go through with it that I will find that out to." We sat and talked a little more, Tyson filling me in on some important dos and don'ts with regards to Sara and James. Most notably never call her degrading names even if you hear him do it. I nodded, never asking how he knew this about his aunt. I sure as shit didn't know this much about my relatives.

After about half an hour we saw a couple walk in to the café, it was his aunt and uncle. Sara was a short bubbly blonde with big fake tits and a skinny ass. She was very thin almost to the point of looking unhealthy, I knew that she treasured her thinness like most women but she could certainly stand to gain a few pounds. Still she was very good looking with her full lips and cute button nose. Imagine Meg Ryan with wonderfully large tits. She was wearing a long gray skirt and a black sweater with a turtleneck. As well she had on a pair of high-heeled black leather boots. She was in my opinion wearing too much make up but she wore it well. All in all for a woman pushing forty she was very hot. She gave Tyson a smile and came and gave him a hug. James was a bit taller and little on the chunky side not to fat just a little big. He was balding but it didn't look too bad on him. He wore a polo shirt and a pair of jeans and sandals. He shook both our hands and the two ordered coffee's.

At this point I was starting to get nervous. This was farther then I thought it would get. Sara kept looking at me and smiling a few times I felt her foot caress my calf. The conversation went smooth and we all got along well enough. James was a very funny and a genuinely friendly guy; I could see why Sara liked him. That and I heard he was very well off and not to cast to dark a cloud on Sara but as Tyson put it she was as materialistic as one could be. Finally we made plans to meet for dinner at the Sparks steak house and then we would go to the hotel from there. Then we said a dues and everyone went their own way.

Back at my apartment I was freaking out thinking I should just back out now before it gets to far. My mind was flooding with thoughts, like what if he has a monster cock. Or I can't get it up or maybe she likes it a certain way and doesn't like the way I do things. 'Pull it together man!' I told myself. 'You're going to do this and you're going to win that beer'. Beside I thought I'm an uber jock in peak physical condition I have a six pack and girls are always satisfied when I'm done, you'll be fine. I reassured myself

On the night of the event I wore a blue suit with a white shirt and a yellow tie I had gotten my hair cut and was as clean as a whistle. I even spent extra long cleaning my ass just in case she was into that sort of thing. I got to the restaurant early and had already had four drinks by the time they got there.

"Hope you weren't waiting long?" James asked as he and Sara sat down. He was wearing a sport coat and blue jeans with a mock turtleneck shirt. Sara was in a tight navy strapless less dress that was very short and showed off her ample cleavage. I could tell she was wearing a garter belt and thong panties. To my pleasure she wasn't wearing too much make up. The dinner was nice and the conversation flowed well. During dinner I polished off four more vodka presses, or vodka and water. I was a little ashamed when James grabbed the bill and saw my drinks cost more then the meals. He smiled and said not to worry and that he was nervous his first time. We hailed a cab and went right to the hotel while on route they explained some rules. One no calling Sara names, two no violence towards anyone, and three if anyone at anytime says stop then we all stop. "Agreed?" Sara asked I agreed and started to feel a lot better.

Sara began to caress my in inner thigh as well as James's. James already had his hand in between her legs and was as I could tell really working her pussy. Sara leaned over and gave me a passionate kiss sliding her pierced tongue into my mouth; this was an added bonus, as I love pierced tongues and nipples. It's not to often you find women over thirty with tongue piercing. James was now kissing her neck and shoulder. The cabby almost got into three accidents as he was paying more attention to us then the road. I felt Sara's hand on my crotch and through my slacks she began to massage my hard cock.

"My god you have a big cock!" I smiled at this. As did James witch was a little unsettling. We pulled up to the hotel and James paid the driver we walked in and James checked us in. once in the elevator James unzipped his fly and pulled out his semi hard cock. Which Sara began to stroke it. As I was feeling no pain now, I pulled her dress down enough to expose her big tits; she was wearing a strapless bra that was cut just below her nipples. I leaned over and took one of the hard red nubs into my mouth and began to lightly bite and suck on it when the door opened we were at our floor and to our shock were standing three young women they looked like they were in their early twenties. Were wearing matching tracksuits.

"Like get a room. Pervs!" one of the girls said.

"Like go fuck you self!" I replied with out thinking. Sara gave a laugh and we walked by them to our room. Sara never pulled her top up and never took her hand off James cock.

We closed the door behind us and James and I continued out assault on Sara's body. I helped her out of her dress asking that she leave the rest on including her stiletto shoes. I got undressed, as fast as I could and once done I was very proud to notice that I was much longer and thinker then James. That coupled with the fact that I was young and buff helped my ego. When James was naked we went to the bed.

Sara instructed us to lie down, which we did. Then crawling up on the bed proceeded to take turns sucking our cocks. Sara had a very talented mouth and had no trouble deep throating my cock, something none of my other partners could do. Up and down her hot mouth went and when she wasn't sucking my cock she was jerking it off with expert form. I watched as she was giving James his turn she would concentrate on the head swirling her tongue around it flicking the tip of her wet tongue on his pee hole, and she would just hold it steady with her hand and not jerk it off. When she was on mine she was much more animated first she would deep throat me then she would suck the head for a bit then back dawn she would go. The whole time she would make loud moaning sounds

After a bit she started to work our balls first James then me. That's how it went always James first. I can certainly understand that. Sara was an expert in my opinion at sucking balls. But what I found most enjoyable was her tongue stud, it felt great on my balls, she had the ability to swab my entire sack with out saliva dripping off of it.

Then she got us onto all fours and was now stroking our hard members much like you would milk a cow, her strokes were slow and deliberate every once in awhile she would stop and massage our balls, this whole time there was next to no talking. I was certainly enjoying myself too much and I was afraid if I opened my mouth I might ruin it. She slowed her pace even more and I looked over my shoulder and too my surprise she was tonguing James's asshole. He was letting out little moans of approval.

Then it was my turn I felt the tip of her hot tongue circle around my a-hole slowly working her way to the center I felt her put both hands on my cheeks and gave them a light spread. My ass gaped a little and that was when she shoved her tongue in, the sensations exploded through my body I began to shake and shiver. I let out a very audible. "Holy fuck!"

"Nice isn't it I love the way she eats ass!" James said, I had almost forgotten he was there, James was now lying on his back jerking off to the sight of his wife eating my ass. Sara was tongue fucking my ass with real passion. I felt like I was going to explode hot cum all over the bed. She withdrew her tongue and inserted a finger, I had never had this happen to me, I had, had a girls tongue lightly dance around my ass but never have I been fucked in the ass by either a tongue or a finger. It was awesome. Now she was really starting to work on my ass I could feel her dribble spit on to my ass to give it more lube. I was also amazed at how comfortable it felt, her fingering it like she was.

She stopped her assault on my asshole, stood me up and laid down on the bed so her head was off the edge then James positioned himself between her legs and began eating her out. Sara had a hairy bush by today's standards, not seventies hairy mind you but certainly more then the average woman. She must have seen me looking. Just before she positioned me she said. "James likes thick bush. Don't worry it's just the top bush. The rest is bald as ten year olds. I want you to fuck my tits!" she said as she striped off her bra and poured some lube between her tits and rubbed some on my cock. Where she got the lube from I have no idea, then again between how drunk I was and how shocked I was it's not surprising I was missing some of the details. Sara guided me forward until my cock was right between her big tits. I held each of her tits and pressed them together and began to slide my cock in and out of her marvelous mounds.

Meanwhile James was licking her clit as he pushed three fingers in and out of her pussy. Sara was tonguing from my balls to my ass with each thrust of my cock. Her tongue felt magical and looking down on her perfectly augmented tits I couldn't help but think this was all a dream, and that was going to soon wake up. I lightly twisted her hard nipples and gave them light pulls.

James stopped fingering her and switched positions so Sara was on her hands and knees she began to give James head. I went to my wallet and retrieved a condom I slid in on and positioned myself behind Sara. Do to how skinny she was I could make out every detail of her pussy. Her lips protruded quite far, I didn't think I would like the sight but it really turned me on. I crawled on to the bed behind her and positioned my hard cock at the entrance of her hot wet pussy.

Her head was now bobbing furiously on James cock. He had his hands on the back of her head and was helping her along. With one long push I buried my whole 8 inch cock into her waiting pussy. Her back arched and she pushed back against my cock almost as if she was challenging me to fuck her hard. I wanted to call her a whore and a slut, I wanted to pull her hair and try and make her submit to me through sheer force, but I remembered the rules and thought that there would be another time and place with another girl for that.

I grabbed her bony hips and began to thrust my cock into her. Her panties were already removed but she was still wearing the garter and stocking's were still on as were her fuck me pumps. Do to the fact that she was lighter then my cat I had no problem pulling her to and fro, as I fucked her harder and harder. My balls were slapping against her clit and her ass was bouncing off my stomach, looking down at her little puckered asshole I felt my balls tighten a bit. I knew I wouldn't last too much longer at this pace. I looked up at James whose eyes were glued on my cock fucking his wife. He was smiling at me, which to my luck seemed to delay my orgasm. I pulled out much to the annoyance of Sara. Who looked back and asked why I had stopped. I didn't answer I just bent over and started to tongue her asshole. She pushed her ass against my mouth and seemed to like what I had in mind. I could see her now slapping James cock on her tongue and that was also the first time I heard any talking between them.

"I love the way you fuck my mouth with your cock honey!" Sara said as she went back to throating his member. I was driving my tongue into her ass as far as I could get it. I have always been an ass man but I had never gone beyond mild licking I certainly never jammed my tongue all the way in there. It was magical I was hooked I now knew I would do this to every woman who let me, and the ones that didn't I don't think I would be able to date them.

Sara straightened up forcing me to as well she turned to me and put her arms around my neck and began to passionately kiss me I could taste it all and I loved it, I devoured her tongue I had forgotten that James was even in the room, again. I picked her up while we still kissed; I carried her to the chair and sat back in it. I easily lowered her on to my prick. She grabbed my shoulders and began to ride me on the chair. I looked at her tits as they bounced up and down, for fake tits they sure bounced like they were real. She slowed down and I saw James come up behind her, he lowered himself enough to move his cock into striking position of her ass. I saw him rub lube all over his hand then he rubbed his cock and guided it in to her ass. With in seconds we were rhythmically double stuffing Sara. Her eyes were shut as she bit her lip and moaned I was thinking, would I get to fuck her in the ass next.

I grabbed her tits and began to massage them; I could feel James's balls hitting mine every so often. To my surprise this didn't bother me. James reached around and turned her head so she was facing him their tongues danced and fought with each other's. I could feel my balls tightening up and knew I would not last too much longer.

"Ughh I'm gonna cum." I said as I bucked my hips up in to her breaking our rhythm Sara let out a wince as both James and I thrust into her at the same time. James pulled out and she got off me. She pulled the condom off me and James sat in the chair. Sara quickly positioned me in front of James. I was still just going with the flow until Sara got behind me and started jerking me off. Normally I would be all for this, only this time my cock was aimed right at James who had a knowing smile on his face.

"What the hell are you doing?" I asked in protest.

"Just go with it sweetie!" Sara said. I was so close to cumming that I didn't even have time to react with one last jerk cum was flying out of my cock and all over James's crotch and stomach. Sara came around and got on to her knees in front of James and eagerly licked and ate my cum off of him. Then she swallowed his cock and jerked his load into her mouth. Sara stood up and spit his load back into his mouth. Which he swallowed with glee.

She turned to me and kissed me on the mouth and thanked me, hoped I had a good time. I was still in shock as to what I just saw and took part in I couldn't get two words out of my mouth. This had been my first three way with another male. I have to say I don't think it will be my last. Sara lit a smoke and sat on the bed. I got dressed and thanked them for a lovely evening. I wasn't sure if there would be a round two and the way they were acting I didn't think there would be.

As I walked out I over heard James. "Now I'm really going to punish you, you filthy whore!" I was about to turn and see if there was a problem but then I heard Sara.

"Oh ya, I've been a nasty slut and I need you to punish me!" I smiled and walked to the elevator. While I waited for it to arrive the young girl I told off in the tracksuit walked up to the elevator. She looked me over.

"Have fun?"

"Yes I did! Say can I buy you a drink?" I asked looking her over.

"You still have life in you after all that?" she asked, now sporting a sly smile.

"I can go all night baby!" she bit her lip and replied, let's go then, and we got into the elevator. But that story's for a different time.