Being in the military, I’ve met friends from all over and we often get into discussions about which football team is the best. My good friend Rick is a die-hard Chicago Bears fan and I’m a hard-core Oakland Raiders fan. We often give each other a hard time about how well our teams played that week.
This friendly competition progressed until we began putting a bet on each season. The guy whose team had the worse record had to buy $50 worth of football memorabilia for the winner.
For the last couple of years my Raiders, while not playing championship ball, were at least outplaying the Bears. This had earned me a lot of stuff, as well as bragging rights.
At the end of last season, I was over at his house, harassing him about another losing season while we drank beer and joked. His wife, also a Bears fan was getting a little tipsy and said that next year would be different; her team would win for sure. I asked her if she was looking to lose a bet along with her husband. She said she’d love to earn some free Bears stuff.
Joking with her, I said that her team sucked so bad that I already had all the Raiders stuff that was made, but that if she was interested, we could make the bet a little more interesting.
When she asked what I meant, I told her that if I won, she would have to wear nothing but Raiders stuff one night, and do whatever I said for that night. She thought about it for a moment and then agreed. She looked over at her husband for his permission and he smiled and said it was fine with him. The bet was on.
Fortunately, that was the season that the Raiders decided to show the league they knew how to play ball, while the Bears kept up their recent mediocre play. As the season wore down, I started getting everything together that I needed. When it was obvious that I had won I went over to their house to collect my prize.
Rick’s wife Sandy is a petite little brunette with a dynamite body. I’d always lusted after her in silence and envied Rick, but tonight I was going to do more than lust after her, that is, if I could actually get away with it.
After exchanging pleasantries, I reminded Sandy that tonight was the night she had to pay up her bet. She tried to get out of it by claiming that she’d been drunk that night and therefore didn’t have to pay up. But Rick surprised me by stepping in and telling her that a bet was a bet and it had to be paid, no matter what. Finally Sandy relented, but asked if we could all have a couple of drinks first.
As we each finished our second drink, I told her it was time to go get dressed. She asked what I wanted her to put on. I told her that I’d accompany her to the bedroom to help her get dressed so we could surprise Rick.
Sandy looked at her husband pleadingly, but Rick just grinned and told her to get on with it.
As we entered their bedroom, I opened the gym bag I’d brought with me and told her to get undressed. As she slowly took off her shirt and pants, I couldn’t help but admire her firm stomach and small shapely ass. She stood there in her g-string panties and bra waiting for me to give her the clothes.
I took my chances and I told her to get completely naked. After a momentary pause, she complied. Standing there with her small tits staring me in the face and that small patch of curly pubic hair over her pussy she was nearly driving me nuts, but it was a long night, and I had a plan all worked out. I hoped.
I pulled a black g-string, boxers, t-shirt, socks and complete sweat set (all with Raiders logos on them) out of the bag and told her to wear as little or much as she was comfortable wearing.
She started to reach for the clothing when I said, “But first, we need a little ornamentation.” I pulled a pack of temporary tattoos out of the bag and told her that she needed to be a complete Raiders fan for the night.
First I applied a small tattoo to each of her tits. As I started to rub them on, her nipples got very hard and so did I. Then I told her to bend over, and I placed two larger tattoos on her magnificent ass cheeks. My hands were shaking as I applied them. I was no longer sure I could control myself, but somehow managed it.
Now properly adorned, I told her to get dressed and come out to the living room. I left her standing there looking a little relieved and surprised.
I told Rick what had happened so far and what I wanted to see happen. I was happily surprised when he said that my plan was fine with him, and that he would do his part to help. What a good friend!
Minutes later Sandy came out covered from head to toe in black Raiders attire.
After some good-natured ribbing, I told her to get us all a round of drinks while we watched some TV. After a few more drinks, we put on some porn videos that Rick had bought.
Sandy was embarrassed but I made her sit between her husband and me and I could tell that the temperature in the room was rising. Then as planned, Rick told Sandy that he see her to take off her top.
She looked at me and then back to Rick. Then to my surprise she smiled and seductively started to remove her sweatshirt. But to Rick’s dismay, she had the T-shirt on underneath. But the film, alcohol, and everything else had her nipples poking through the shirt. For someone with such small tits, her nipples were pretty large, I thought to myself.
Then reminding her that she was to obey me, I told her to remove her pants. Again she pranced around till she dropped them to reveal her boxer shorts. Even in them, she was a sight to behold, and I wasn’t going to be able to drag this out much longer without coming in my pants.
After another drink and some more of the porn video, I told Sandy to take off the boxers and T-shirt.
Willingly she complied and was left standing there in only the g-string which disappeared between her ass cheeks, revealing to Rick her new tattoos.
He laughed at the sight of them. Then Sandy sat down between us on the couch and we began to explore her body with our hands, rubbing her slim shapely legs, her small firm tits, and her very wet pussy. There was no turning back now. The fact that she was letting me finger her was making me crazy.
I told her that she needed to accompany me back into the bedroom to continue what we had started. She looked at her husband, then asked, “What about Rick?”
I told her that his team hadn’t won, so I would be the one getting the grand prize.
When Sandy looked at her husband, he said it was only fair, and went back to watching the film, while I led her down the hall.
Once inside the bedroom, I began kissing her passionately, while grabbing two handfuls of that awesome ass of hers. After a few minutes of tongue hockey, I pulled back enough to start to remove my clothes, and told her to remove the g-string.
I laid her down on the bed and lay next to her, kissing and fondling her hard body. My hands and lips roamed over her tattooed tits, her firm tummy and down to her wet cunt. I could feel her excitement and rapid heartbeat as I eased a finger into her tight little pussy. She began to slowly move her hips in rhythm to the finger fucking I was giving her.
After a few minutes of this I said, “Baby, I’m going to have her every which way tonight.”
She asked what I meant by that. I told her to start by giving me a blowjob and she would see. I lay on my back, and she got on her hands and knees next to me and engulfed my cock in her mouth.
I couldn’t believe that she was doing this. I’d never even dreamed of her doing this and thought she would refuse. But she was fantastic at sucking a cock. She sat there with my dick sliding in and out of her lips and her ass up in the air next to my head. I was wishing I could be enjoying this tongue bath and fucking her at the same time, but that would have to wait.
I reached over and again stuck a finger into her moist pussy and began to massage her clit. This got her sucking my cock even harder. Soon there was no holding back and I shot a huge load of cum into her mouth. She responded by drinking down every drop like she hadn’t eaten in a week. I was in fuck heaven.
To allow myself to recover, I pulled her leg over my head so that her sweet cunt was just above my face, and pulled her ass down so that I could start to dart my tongue into her juicy pussy. She continued to lick and massage my cock, as I tasted the sweetness of her cunt. She began to moan softly, and then more loudly as I alternated between flicking my tongue across her clit and dipping it into her tight little hole.
Soon she had my cock standing back at full attention as she ground her pussy up and down on my mouth. Within a few more minutes, she began yelling, “OH YES! Eat me you bastard. Eat my pussy raw!” Then I felt her whole body shake as she flooded my face with her warm wet juices. I’d never seen a woman cum so much in my life.
As her orgasm subsided, I rolled her over onto her back and pulled her legs up and bent them until her knees were up against her chest and spread wide apart. Slowly I began to sink my dick into her hot cunt. She was so wet, but so incredibly tight that I was having trouble going slowly. After inching about half way into her steamy cunt, I sank the rest of my dick all the way into her with one thrust. She reached up to grab my ass and pulled me into her with each stroke. I kissed her and roughly pulled her nipples as I pounded her hot little box.
Having just cum, I was able to maintain the pace for a while before I felt that familiar tingling in my balls. By now she was thrashing around deep in her second orgasm, growling for me to fuck her harder, which I willingly did.
Then I took one final thrust deep into her pussy and blew another load of cum up inside her hot cunt.
We lay there panting for breath for a few minutes to recover from the moment before I pulled out of her and let a trail of sticky cum follow my semi-hard cock out and up on her well trimmed patch of pubic hair.
She told me that she enjoyed that, and I told her that we weren’t done yet. She asked what I meant, and I told her that I’d only been in two of her holes so far…there was still one to go. She said that she’d only let Rick in her ass twice, and wasn’t sure it was such a good idea.
I reminded her of the bet, and told her it was time to get my dick ready for action again. She resigned herself to her fate and got up on her hands and knees to start cleaning our combined cum from my cock. Within a few minutes I was hard and ready for action again.
She told me they had some KY in the nightstand, so I reached over and grabbed the tube. I put some on my dick and then began to spread some around her asshole. Then I put a little more on my finger and began to slide it up into her ass to make sure she was good and lubed up. As I got into position behind her upturned ass, I could see the two Raiders tattoos on her cheeks and smiled.
Slowly, I started to feed my cock into her extremely tight ass. As the head popped in, I stopped to give her time to adjust, but the sensation was driving me crazy. Her ass was gripping my cock like a vise and I was loving it.
Soon I had it buried all the way into her ass, and began pumping her butt slowly. Then as she began to get into the rhythm, I speeded up. Because of the enormously tight feel and grip on my dick, it didn’t take too very long before I again shot a load deep into her ass.
As I pulled my cock out of her ass, I could see cum leaking out of both of her holes now. She asked if I was through now.
I looked into her pretty eyes and said, “Now you have to go out into the living room and tell Rick exactly what has just happened.”
She got this nervous look on her face. It was almost as if she’d forgotten all about him. Then I told her that not only was she going to tell him in every nasty detail what we had done, but that she was going to do the same thing for him while I watched.
By now I guess she figured, what the hell. So she got up to go to the bathroom and clean herself up. I stopped her and said, “Uh, uh, you have to go out cum and all.”
She didn’t say anything; she just turned and walked out of the bedroom and down the hall. As Sandy walked into the living room, naked with my cum running down her inner thighs, I began to get hard again from the sexy sight.
She walked over to Rick and gave him a big wet kiss. Then as she massaged his dick through his pants she said, “Don’t be mad at me, but I have something to tell you. Dan is making me tell you.”
Rick just sat there enjoying her touch and waiting for her to continue.
“As soon as we went into our bedroom Dan took off his clothes and started feeling me all over my body. I didn’t want to cheat on you, but I was so horny, and I didn’t want to welsh on the bet.” She hesitated while she unzipped his pants and released his hard cock. He was circumcised just like me.
Massaging his swollen dick in her small hand she continued, “After he got me really wet by fingering me, he made me do this.” With that she lowered her lips to the head of his dick, and slowly took the whole thing into her mouth and began to give him a great blowjob.
I watched as Rick leaned back and just started to enjoy her expert mouth and tongue. Before long, he blew his load down her throat. I guess the combination of the porn flicks and knowing what she was going to do to him really excited him. He came so much it began to dribble out of the corners of her mouth. What was even more amazing was that he never lost his hard-on.
Then she told him how I had eaten her out, and he placed her on her back and cleaned her pussy of our combined juices, helping her to two more orgasms in the process. Without her giving him instructions, he then mounted her and fucked her missionary style. I’ve seen a lot of fuck flicks, but before now, had never actually watched two people fuck live right in front of me. It made me so hard that I was almost in pain.
Rick was pounding into her while she begged him to fuck her harder. I watched as his cock pulled almost all the way out of her tight twat and then slammed back into her. After what must have been 10 minutes, he thrust one last time and held himself deep within her and his body jerked a few times.
After a few moments, he pulled out and their combined cum was evident from her pussy. Rick said that he needed to rest. I told Sandy to stroke him while she told him what else had happened. She took his wet dick into her hand and began trying to pump him back to life while telling him the rest of the story.
“After Dan came in my cunt he made me lick him clean and told me he was going to fuck my ass. He was nice enough to use lube, but my ass is still sore from the pounding he gave me.”
Rick was growing harder, but not there yet. While I on the other hand was hard as a rock. I told her that while Rick was recovering she could do me one more time. I got down on the floor and told her to climb on and put my dick in her dripping hole. After giving Rick a kiss she moved over to where I was and straddled my hips.
She looked over at her husband one last time and then slowly sunk down and grabbed my cock. Then she guided me into her sloppy wet cunt. Then in a slow rhythm she sat straight up, fucking herself with my cock.
After a couple of minutes I saw Rick moving toward us. I pulled Sandy down to my chest and held her with her tits pressed against me. Rick moved up behind her and spread her ass cheeks. She was startled for a second, but never lost her rhythm while we fucked. Slowly Rick started to enter her upturned ass. I could feel his cock as he entered her ass while I was in her pussy. I had heard that this was a really erotic experience for all three involved, and at least for me, it was true.
Finally, Rick got all of his meat into her ass and then began matching my thrusts, while Sandy began moaning and saying “Oh God, oh yes, oh please fuck my brains out!”
We were only too happy to oblige her. We continued our assault on her two holes, me from below in her cunt and Rick from behind in her ass. The sounds and smells of sex in the room were almost overpowering. She had what must have been her 5th or 6th orgasm and screamed at the top her lungs that she was cumming. That sent Rick over the top and he came deep within her ass.
That chain reaction continued with me as I once again filled her pussy with my seed. We all stayed right there with all of our combined cum leaking out of her and onto me and the floor.
After a couple of minutes, we managed to pull ourselves apart and Sandy walked awkwardly toward the bathroom to clean up.
Rick and I smiled and followed her in. After she was in the shower, we both walked in to the shower stall and helped her clean all of our combined cum off.
After toweling her off, we led her to the bed and went to sleep with her in between us.
All of her Raider tattoos, although somewhat faded and smeared, were still plainly in sight. As I looked at her body I thought to myself, “That was the best bet I’ve ever made.”