The Sure Thing

by Just Plain Bob

Caution: This Sex Story contains strong sexual content, including Ma/Fa, Consensual, Heterosexual, Cheating, Gang Bang, Slow, .

Desc: Sex Story: He and his buddy would bet on anything.

I'm a gambler. Oh, not a high roller by any means, but I do love to bet on things. Once, in Houston at the Hyatt Regency, a couple of us sat in the lobby and bet on the elevators; which one would get to the top first, get down first, or if it was stopped at a floor would it go up or down. Not big bets, but bets just the same. I'll never put myself in the poor house, or lose my house for that matter, but I will bet on almost anything. Sometimes with some very surprising results.

I am also one of those men who would like to see his wife make love to another man. It is a desire that my wife has steadfastly refused to honor ("what a disgusting idea" - how can you say you love me and suggest something like that" etc., etc.) so I had resigned myself to the fact that it was never going to happen.

And then one day --

I was sitting in the Dew Drop Inn (no kidding, that is the name of the place) with my best friend Todd and we had just watched two women enter the ladies restroom. Todd bet me a drink that the one in the green dress would come out first and, naturally, I took the bet. The blue dress came out first so I offered Todd a chance to get even. I bet him the girl in the blue dress would be asked to dance before the girl in the green dress and when Todd took the bet I got up and asked the girl in the blue dress for a dance. Todd was shaking his head when I got back to him, "I guess I fell for that one" he said, and I laughed and told him that I dearly loved to bet on sure things. He snorted and said that there was no such thing as a 'sure thing'.

I fired back with "Sure there are. The sun always rises in the East, everybody dies, the IRS always gets its money and Betty (my wife) is 100% faithful."

At the mention of Betty Todd perked up. Betty, Todd, and I had grown up together and had known each other since the first grade and at different times Betty had gone steady with both of us. After high school Todd had gone into the Marines, I had gone into the Army, and Betty had gone to college. Betty had married, become a widow, and when I was discharged we began seeing each other and eventually married. Todd came home from the Marines in time to be my best man, but he had never lost the hots he had for Betty. I kidded both Todd and Betty about his 'puppy love' but they both just ignored me. Anyway, Todd couldn't resist taking a dig at me, "You are absolutely certain that Betty is faithful to you?"

"Of course" I replied.

"You willing to be on it?" asked Todd.

"In a heart-beat" I told him.

"Tell you what," Todd said, "I'll take that bet."

Talk about a can't lose situation. I was tempted to go for some big money on this bet, but at the last second I reined myself in - I just bet for the enjoyment of it, not to get rich. "You are one," I said, but only on one condition. I won't just take your word for it, I have to see it for myself."

"OK," Todd said, "but I have a condition too. You have to promise me that Betty never finds out that you watched us."

We shook hands on the deal and I asked him how much time he thought he would need. Todd laughed, "How about noon tomorrow? Can you be at my place by 11:45?"

I was stunned into speechlessness. I stared at him for several seconds before saying, "You can't be serious!"

Todd gave me his biggest smile, "Be there or be square" and he laughed again.

The bet? Loser springs for lunch.

The next day I was at Todd's apartment at the appointed time and Todd had me get into his bedroom closet. The closet was cedar lined and the door had louvers in it to allow the air to circulate so I had a very good view of the bedroom. Todd undressed and lay down on his bed while I stood in the closet and wondered what the hell was going on. About five minutes after I entered the closet I heard someone running up the stairs. The bedroom door opened and in walked Betty. She didn't say a word, just started taking off her clothes. When she was naked she walked over to the bed, bent over Todd and took his cock into her mouth. After several minutes of sucking his dick she got up on the bed, swung over him and the two of them settled into the sixty-nine position.

I watched in absolute amazement as my wife, the same wife who told me I was disgusting to think she could ever have sex with another man, enthusiastically sucked my best friends cock. The thing that did not surprise me was my reaction. I got stiffer than a board seeing my fantasy come true, it was every bit as exciting as I had thought it would be. I toyed with the idea of coming out of the closet and joining in, but I had promised Todd that Betty would never find out that I had watched, and a promise is a promise.

They switched positions and Betty swung over Todd and lowered herself onto his stiff pole; she began rocking up and down and as I watched her tits bounce and her long dark hair fly about her head I fished my own pole out and began to stroke it. I heard Betty utter the little cries that indicate she is cumming and I shot all over the inside of the closet door. Betty got off Todd and swung around to lick the juices off his cock and kept working on it until he became hard again. She rolled over onto her back and spread her legs open for Todd and he wasted no time in moving between them and driving his cock into Betty's wet cunt.

As I watched them go at it I noticed that I was hard again also (or maybe it never got soft after I came, I'm not sure) and I began to whack myself off in time to Todd's thrusts. By the time I was ready to shoot again Betty had gone through several orgasms and was imploring Todd, "Cum for me baby, cum for me, let me have it."

Todd said "Here it comes, I'm cumming, I'm cumming" and I did too. Only this time I turned and shot all over Todd's clothes (a little vindictive I admit, but the man had obviously been fucking my wife for some time now).

Betty did not stay around and snuggle or cuddle the way we do when we make love, but got up and left immediately. Todd came over to the closet when she was gone and gave me his big smile, "Like you said the other night, I sure do love a sure thing. I want lunch at Benny's."

"I don't know about that" I replied, "I'm not so sure that I came out a loser on this deal. Oh, by the way, you have a bit of a mess to clean up in your closet."

Todd and I were sitting in the Dew Drop Inn drinking beers, making bets, and talking about (what else) my wife Betty and my mistaken assumption that she was faithful to me. Todd had proved me oh so wrong on that. We had just bet on what the next person to sit down at the bar would order, I said beer and Todd said mixed drink, when I asked the Burning Question - "Just how long have you and Betty been getting it on?"

Todd gave the question a few moments of contemplation before replying, "Just a little over two years now."

Two years! And I never suspected a thing. But then, why should I have? Betty and I have what I consider to be a great sex life - three, four, and even five times a week, and there is more to it than just frequency; we do it all and in all the positions you can think of. Todd's answer to my first question naturally led to the next two, "How did it happen, and why?"

Todd gave me a rueful smile, "I knew when we made the bet last night that we would end up having this conversation and I've spent the last twenty-four hours thinking about what I was going to say. I decided that it would be best not to sugar coat the pill. I'll give you the why first; I don't think you are going to like this, but here goes, Betty is a slut. She loves to fuck and she will fuck just about anybody if the time and place are right. What that means is when you are at work, out playing golf, or out of town on business, Betty is somewhere getting fucked."

I sat there practically speechless. I was having a hard time accepting what I was hearing, but after seeing Betty and Todd together I had to believe it.

Todd continued, "But there is more to the why than that. Betty needs more sex than the average woman, and even though she gets a lot from you, it just isn't enough. She told me about your fantasy and I have tried to make her see how advantageous it would be for her to agree to do it. It would give her the chance to get all she wants with your approval, but she loves you and is afraid she will lose you if you ever find out just what a cock crazy slut she is."

I was so distracted by his story that when the next person to sit down at the bar ordered a beer I didn't even point out to Todd that I'd won the bet. That left the last question, "How did it get started?"

"First" said Todd; "I want to be up front about one thing. I don't regret for one minute that I'm fucking your wife. I've known her every bit as long as you have and if things had gone my way I'd be married to her instead of you. And, I'd like to think that by fucking her and seeing to it that she limits her fucking to a select group of our friends that I help keep her from getting a disease or from getting into dangerous situations."

His "select group of our friends" caught my attention and I asked him, "How many and who?"

Todd said he wasn't ready to name names, but that there were nine of them.

"The reason I took the bet last night was that I have become more and more certain that it will benefit both you and Betty if we can get this thing out in the open. Am I right?"

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Story tagged with:
Ma/Fa / Consensual / Heterosexual / Cheating / Gang Bang / Slow /