Nat with Cindy

Ok, here are the details of the one and only encounter between Cindy, my wife at the time, and my best friend's sister Nat, current girlfriend.

Cindy's parents had a house in the Florida Keys that we would all spend almost every summer weekend at. Sunning, riding wave runners, boat trips, and relaxing were the typical events. We would always end up inviting friends to come and spend a day or two with us since there was always plenty of food and room to spend the night.

On one weekend, we invited a few friends including Rick, whom Cindy had been sleeping with on occasion, and Nat, his sister....

Everyone came down on Friday night and we started to party early. A few of our friends had vacation trailers nearby and tonight they all ended up at Cindy's place. We had plenty of drinks and the house was all ours … Cindy's parents didn't come up that weekend. Most crashed over and the festivities went well into Saturday.

Late Saturday, most everyone had to take off back to Miami for one reason or another. The only ones left were those who actually had a place down here. At our place was Cindy, her sister and boyfriend, and Nat. Two other couples also stayed the entire weekend at another trailer down about a mile. And last but not least, was a guy who we'll call 'Bill' for this story.

Bill lived two streets over from Cindy's place in the Keys. She had seen him endless times at the Keys when she was younger. He was the first to have a jet ski when they first came out and then a wave runner … and he used them to his advantage. Since everyone in that community pretty much knew each other, he would let Cindy go riding and he would go with her. Cindy doesn't think he ever tried to make a move on her but she was sure, looking back, he got a feel here and there … but she was young and illegal and he was much older.

I actually met him before we were married at Hog's Breathe, a local saloon and a great place to visit if you ever come to the Keys. Cindy had slept with him way back then in one of our 'see if she could get picked up' dates where he ended up being there and took the bait. Since then, we've spent many days and nights at his place whenever we would come to spend the weekend at her parent's. He actually was the one who got her to do daring things in front of his friends and expose her in public. Luckily none of his friends lived in the neighborhood or knew her parents.

Anyways, back to this story.

Saturday night we ended up going to Hog's Breathe Saloon and, on the way, picked up Bill. We spent most of the night continuing our drinking and debauchery. Finally, Hajim wanted to go home so we tried to figure out who was most sober … and that was Bill. He drove us to our home and we chatted for a bit inside as the rest got ready for bed. I knew that he had already taken some feels off of Cindy at the bar and as we walked from the car, and I was horny as could be. Bill said he was off if anyone wanted to go over and have some more beers at his place. Everyone was pretty much done for but Cindy and I jumped at the opportunity. We figure we'd be safe with everyone going to bed .. so we left walking with Bill to his place.

On the way Bill would walk up behind Cindy and lift her skirt to get a peak and she would slap it down and saying that people around here might see … and she knew them all.

When we got to his place there was not much foreplay. He threw me a beer, turned Cindy around and began making out with her but in the spin she almost fell to the floor, most likely from all the drinking. I plopped on the couch and just watched them. As horny and in the mood as I was, the alcohol was taking its toll on me and I was just fine watching.

Bill is a tall guy at about 6 feet. He is a burly man with tattoos, a bushy beard, and a decent gut … but Cindy always found him attractive in a rough sort of way. I swear you could put a biker's jacket and put him on a cycle and he would fit the part. The other thing which I know Cindy enjoys is his thick cock … not long at all, but quite thick. The funny thing about him was the he was always very gently when he was with her which, once again, by looking at him you would never picture it. It wasn't until Rick took control of her that she began wanting things a little rougher. It was never really me and even though I would try, others could do it much, much better. The last few times with Bill she would tell him to be rougher, harder, and nastier … and he was. I guess he was just afraid of scaring her off at the beginning but now he seemed quite natural at it.

There was Cindy in her tube top-style shirt and flirty skirt on her knees giving him a blowjob and me on the couch; his hands gripping her hair and head while shoving her into him. Nice …

The next thing I remember was opening my eyes and they were gone. Just my luck, I passed out but it wasn't that long because my beer was still in my hands and pretty cold. Then I heard them faintly in the bedroom moaning and going at it. All I could do was smile. I wanted to go there but I was so exhausted … and started to fade out again. In the blink of an eye I sprang out of that couch like I the devil himself slapped me.

The trailer door squeaked open and that is all it took to get my heart into my throat and be as sober as ever. Nat came in the door and walked right to me in her Pajamas, flannel-like pants and a shirt) … nothing very revealing but still nice. She started to tell me that she came out of the shower and we were gone so she asked Cindy's sister which house it was and decided to find us and have some more beer. All I could think about was how to get either her out of the house or tell Cindy she was here.

She asked me where they were and I'm sure I said something stupid like … "picking flowers" or "he's showing her his furniture" but whatever it was she bought it. I got her a beer out of the kitchen hoping to see down the hall and catch someone's attention but the doors were closed. So I gave her the beer and said I would go find them.

I quickly opened the door and told them that Nat was here. My wife was on the bed with her legs nearly at the side of her head as he held them down and stopped inside of her as I interrupted them. Cindy's eyes were closed and her hands her wrapped around her legs. Bill sprang off of her and started to get dressed and Cindy did the same. I went ahead out and sat with Nat and a few minutes later they both came up. Luckily, the only really sober one was Bill and Nat didn't realize anything like Cindy's messy hair or his sweating profusely.

We must have had about 1 more beer each and then Bill came out with the game of a lifetime … quarters. I don't know who came up with it but it was the first time I played it. Yes, I know…not much of a college life I had.

This went on for a few shots and then Cindy said she really couldn't have any more to drink or she would get sick. Nat, I, and Bill were still ok, so Bill said that if she couldn't take a shot she would have to loose a piece of clothing. It was her choice. Cindy stood up to go to the kitchen to see if there was anything lighter like wine coolers. Bill went after her. I looked over and Nat had her head back on the couch and was licking her lips … what a sight.

They returned after a long few minutes and my heart began to beat faster. I know how Bill loves controlling her and he said she could either strip or do something he told her to do, like a dare… and I knew where this was heading. A lot of what happened that night is even now a little hazy but I did remember thinking that, although Bill had met Nat only a few times, he wasn't a very shy guy especially since he had already exposed my wife to other people when she wasn't even drunk.

Ok, so now we are playing Truth-n-Dare-Strip-Quarters without the Truth. There is a new game. After several rounds Cindy had taken her shoes, socks, and shirt off. All that was left on her was her bra & panties and her skirt. Nat had done one round as a strip option but took off her shoes and socks and then went back to drinking. Bill and I also took our shoes off … it was sort of a rest between rounds.

The next round Cindy didn't want to strip so Bill told her she had to give one of us a lap dance. She came over to me and did her dance while Bill and Nat watched. When she sat down, it was between Nat and I. I looked over at Bill and noticed he had his hand on Nat's lap and her head was leaning on his shoulder … she was quite toasty but wanted to keep going. The next time Bill told Cindy she had to kiss Nat.

Nat looked up and laughed but didn't really say anything. Cindy leaned over and gave her a quick peck on the lips. Bill and I started to say it didn't count and before you knew it they were making out. That was the only time I've ever seen her kiss another girl and I was in heaven.

Somewhere into the night, I found Nat leaning back against the sofa with her eyes closed. It was on this round Bill lost and took off his jeans. It was obvious his boxer shorts weren't made to conceal anything. Then it was Cindy's turn but she took off to the bathroom and Bill and I kept looking over at Nat and each other. Bill reached over and brushed his hand on her leg pajamas and I guess since she didn't make a move he ran his hand up her side and over her breast for a brief second and pulled back when he heard the bathroom door open.

When Cindy came back he grabbed her legs, stopping her next to him, and slid his hand up her skirt and from my vantage point I could see that she had never put on her panties and he was fingering her. She looked at me and Nat and closed her eyes. He pulled her skirt off and pulled her down and pushed her head into his lap as he slid his cock out of his boxers. There they were amidst a BJ and I was sitting next to Nat as she slept. Then he sat her on his lap and she straddled him with her legs around and moving up and down slowly. He ripped her bra off and began to suck and bite her tits.

I was getting hard again and I remember this part well because liquor and getting a hard on don't go hand in hand. I got up to remove my jeans and as I pulled them off my last leg I ended up off balance and fell back onto the couch.

So now we have Bill facing me, my wife on his lap facing and fucking him, Nat against the couch facing them after me landing on the couch and waking her up. I'm sitting next to Nat without a shirt, a pair of pants in my hand, and a hard on. To this day I still laugh at her expression but she kept looking as if in disbelief. She looked at me and then at my hard on and then back to them. I really didn't know what to say but I know what I wanted to do … so I leaned over and as she looked at me, I kissed her and she returned the favor. This is the only part Cindy never knew about because she wasn't looking but we kissed for a few minutes and I even ran my hand down her breasts and between her legs.

We stopped when Cindy started moaning louder as she was about to cum. Bill pushed her off of him and against the couch and bent her over. She was a hands reach away from Nat, but I don't think Cindy even noticed Nat was awake at first until Bill started to do her from behind and she looked over and was partially startled but didn't stop. Bill reached over and began to caress Nat's breast.

When I spoke to Nat about this today she said that she was in such shock she didn't really know what to do or say. It wasn't that she even wanted it … just didn't have any idea what was going on.

Well, I laid back on the couch and watched as Bill fucked Cindy, slapped her ass from time to time, and groped Nat. He took Cindy's hand and placed it on Nat's breast and started to feel her up (wooohooo, her second time feeling a girl up). Bill finally came inside of Cindy and leaned over her, kissing her back and rubbing her hips. Cindy stayed leaning on the couch for a few minutes and then slumped to the floor, breathing heavily and sighing to herself, her eyes closed.

After a few minutes, I was almost done stroking myself when Bill crawled in front of Nat, leaned into her and began to kiss her. He pulled off her shirt and he then began to pull her pajama bottoms off and then her panties. This guy was quick and Nat didn't say a peep. He dropped between her legs and began to eat her out and finger her.

She was and still is one of the loudest moaners I've ever met. Cindy looked up and smiled at me and then dropped her head to the floor again. I went over to her and began to kiss her and feel her warm body. I had Cindy give me a hand job as I watched Bill and Nat. It took a while but Bill finally got hard again and in no time, picked her up onto the couch and began to pump her. She moaned and groaned even louder. I came instantly and began to kiss Cindy passionately. God, I was turned on big time. I admit I really wanted to join in but since this had never happened and Cindy was pretty much gone, I didn't feel right. Ultimately, I ended up with Nat … but, incase you are wondering, it wasn't the reason Cindy and I are no longer together.

Anyways, Cindy and I collapsed on the living room floor. I don't even remember seeing Bill cum with Nat. The next day I was the first to wake up with the sun beaming into the room. I got up and went to the bathroom and saw Nat and Bill in his bedroom completely naked on the bed cuddling. She looked amazing, bronze skin, great body, long dark and silky hair (and I'm not just saying that because she'll read this.)

I finished, got dressed woke Cindy up to leave. We walked to our house and she asked me all the details about last night because she didn't remember much. I told her she kissed and felt Nat and she hit me thinking I was lying. All I could say was she could ask Bill later and she did.

The only bad thing was that I felt really awkward seeing Nat later that morning after all that had happened. She never said a word to me but when we started dating she brought it up and said she never wanted to do the whole 'swinging or sharing' thing like Cindy. I agreed and told her I had no problems with that. Then came the day with Cory and it was her who brought it up … isn't that convenient.

I also found out years after that Nat had ended up dating Bill even while he slept with Cindy. Nat didn't know he was cheating and we didn't know Nat was involved.