A Very Friendly Wager

by Wayne Gibbous

Copyright© 2009 by Wayne Gibbous

Erotica Sex Story: Have you ever bet who would have the most orgasms during a dirty weekend? This forty-five year old widow wagered she could out do two younger guys put together. Guess who won? You ladies already know, don't you.

Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa   Consensual   Heterosexual   Oral Sex   .

Chapter 1

My husband, Charlie, died three years ago, leaving me, at age forty-five, with a lot of years left. At least I expect (and hope) that's the case.

And, he left a very horny widow. He should know. I dragged him into the bedroom at least every other day, often every day. He never complained and I never was completely satisfied, either. I am one of those women, rare, if you listen to guys talk, common, if you hear divorced wives talk about them, who just love sex. I was twelve when I first had intercourse (I know, shocking, huh?) and I haven't slowed down since.

Well, actually, yes, I have. I mean I have three grown children so I can't just play the slut and get all I want. So, I have a few gentlemen friends that cater to my needs, at least some of my needs.

There are two, in particular, Gene, twenty-seven, tall, wavy ash blond hair, and Calvin, or Cal, thirty, brown hair, cropped short. Both are attractive and gentlemanly.

Gene is the taller one and has a slightly larger cock. Well, you want to know what's important about these two guys, right? They are both wonderful in bed. Very skilled as am I.

Of the two, Cal, I think, is the better with his tongue, while Gene gets a slight nod in the intercourse competition. But, really, both are wonderful.

I met Cal first about a year after Charlie passed on and we were soon in bed with him trying, rather desperately, to keep me satisfied. I told you, I am a lust-filled woman. The truth is, I love to fuck. I would be a prostitute if I could do it without risk.

Then about six months after I met Cal, I was introduced to Gene at a party. I took him home that night and we made love four times and he gave me oral sex twice before he left the next morning. He told me I was the most sexually voracious woman he has ever met and that I could expect to see a lot of him in the future. What a nice man.

So, I have two nice men to take care of me and they were introduced to each other about two months after I took Gene to bed. I talked to each one about the other, carefully explaining that I had needs that were rather extraordinary, and that, if they both were interested, we could do a threesome any time they wished.

Pretty slutty, huh?

Well, it's something I'd never done before though I had dreamed about it often. Very often. Very, very often. And, they both thought it would be fun.

So, I had both over for a nice meal and I wore a very low cut dress with a slit up the side that Charlie had bought me for a party years ago. Yes, it was pretty slutty but fun.

As I served both my guests, I told them that they were not to grope the server unless they wanted dessert. I was immediately fondled and caressed much to my pleasure. Nice start to any meal.

After we ate, we took brandy into the living room where I was stripped by two very interested men who proceeded to pleasure me top to bottom. I had a can of whipped cream that decorated their dessert though it did leave some stains on the sofa that I had to sponge off the next day.

Now, when I say that I'm a widow, yes, my husband did pass away. And, I'm forty-five. But, I'm trim, still have a waistline, a pretty flat stomach, and breasts that look pretty good. The truth is, Charlie wanted me to have my boobs done and I did it for him. Oh, not made bigger, they were just the right size for my frame already, just brought back up to specs, you might say. Um, eighteen-year old specs. I can wear a bikini and get a lot of looks, though I just can't do thongs. Sorry, guys.

I do shave (yes, there) and like the look and feel of it.

So, the last time we had a threesome, our conversation got around to sex (surprise!) and something that I had said jokingly over dinner.

I had remarked that I could easily outlast both of them in a sex contest. Gene asked, "Were you serious about being the winner of a sex marathon against the two of us?"

Hmm, I thought, I've really never, ever have had enough. Even with the help of 'the little blue pill, I was pretty sure my pussy could outdo both their cocks, so I said, "Yeah, I'm serious. Sure. And I've got the Viagra."

I did have several bottles of the stuff from when Charlie was active and also for a few older friends who I like to entertain at times.

So, Cal said, "I'm in, how about you, Gene?"

"It's a bet. What's the payoff?"

"Well, whoever wins, gets to pick the next place we hold the marathon."

"Oh, Rita, you're on. It's a deal."

So, we discussed the ground rules. We kept it pretty simple. First, we were to be naked the whole time. Second, any one of us could touch or do anything they wanted to do to another but it had to result in an orgasm for me every time. We would add together the guy's orgasms and compare it with mine at the end of the weekend. The side with the most orgasms wins. We would check into a hotel on Friday afternoon and leave Sunday afternoon. The bet was on. I made a reservation at a classy hotel downtown for the next weekend. A room with a hot tub and a round, honeymoon bed. Oh, yes, fun.

Now, you might think that, well, of course the woman will win. Yeah, maybe. But I think we all didn't really care. It was just a fun idea for a dirty weekend.

We did bring robes in case we had to answer the door, like for room service for our meals, but as soon as we entered the room, each of us took off and hung up all our clothes. I then kissed each man on the lips and on their cocks welcoming them.

Then, Gene opened the first bottle of champagne that had been delivered along with some sandwiches and hors d'ouvres. We all three stood there sipping our first glass as I admired the two very handsome young men and their nice, hard cocks waiting expectantly before me.

Calvin led me to the bed and got down between my legs and began licking me all around my pussy. I asked Gene to get close so I could suck him to keep him interested while Calvin tongued me. I just love doing this, being eaten and sucking a cock at the same time. Yes, it got me my first orgasm pretty quickly.

Then, Calvin got up and pressed his cock into me and began his nice, slow rhythm that I love so much. I just put my legs up along his shoulders and he fucks me nice and deep and slow pushing down into me and leaving it deep as I circle my hips. Oh, it was delicious.

I knew that with Cal's cock deep in me and my twisting my pussy around his cock, that an orgasm would be in the offing pretty quickly for both of us. It had become our favorite way of fucking and, sure enough, we both soon got our wish.

Then, Gene wanted doggie-style, also a favorite of mine, how nice of him to ask, so I got up on the bed and he slid into me from behind, my pussy all slick inside with Cal's fresh, warm semen.

Oh, it felt so good when Gene's nice, big cock descended to my depths. He is really hard, swollen, ready. I wanted him second because I knew that after he watched Cal and I, his cock would be bursting. He gets so engorged when he is aroused and has to wait. I sometimes just suck on him slowly for a half hour or so, just to fill his beautiful cock with blood to the bursting point before I let him enter me.

"Ew, Gene, oh, baby, that really fills me up. Oh, so good. Yes, just go nice and slow. God, that feels good."

"Oh, oh, I really want this so bad. Waiting there, watching you two, oh, this is much better. God, you feel good inside. Really slippery. All Cal's cum, I guess."

"Mmm, yes, and you can add to it. That feels so nice, you like this?" I asked as I began moving my butt in a circle around his cock. He just arched his back jutting his cock out for me to twirl my pussy around and pulled back until it was just the tip of his cock that remained inside me.

Oh, this felt so good. So much feeling is near the entrance to my pussy and on the tip of his cock. And we were giving those two areas all our attention. It was so good.

Then, Gene pushed forward burying his dick all the way in me and I pushed back pressing him as far in as he could go. I flexed my vaginal muscles over and over trying to milk the cum out of him.

"Oh, Rita, that's so good. Oh, that'll make me cum, for sure."

"Then you get one more point. Are you ready?"

"Any time, hon, any time," and I moved my hips around as I continued to flex and relax around his cock and I could feel his cock begin to spasm as he filled my with his warm cum.

"OOOH, OOOH, OOOH, OOOH, oooh, oooh, oooh, oh, Rita, oh, hon, Cal, get us a towel. Rita's pussy runneth over."

I got up and wiped myself off knowing that it was only temporary as Calvin invited me back to bed. I got up over him and lowered myself on his reenergized cock.

"Mmm, oh, that's nice. From one cock right onto another. Oh, I do love you two."

Calvin began rubbing my breasts as I went up and down over him. I pushed down all the way so I was sitting on his pubic bone and then twisted my hips back and forth, rubbing his cock tip up against me deeply.

"Mmm, oh, Rita, oh, you've got me so hard. I'm gonna score another point here pretty quickly."

I know how to make men cum, that's something I've practiced on for years. In fact, my first time with Calvin, he unloaded in me in under three minutes, he told me he was never that fast. I told him, maybe so, but he'd never had me before. We laughed over that ever time he had an orgasm after that. We've laughed a lot.

"Oh, yeah, oh, Rita, oh, you've done it again, oh, yes, oh, OH, OH, OH, OH, oh, oh, oh, wow, mmm, oh, another point for me."

"I'm not finished, yet," I said as I pushed down hard on him and twisted back and forth. Oh, yes, this always works for me, especially if the guy has a cock long enough to get really deep in me. My husband, Charlie, when he was younger could send me up like a rocket.

"Mmm, oh, yes, that's getting here, yes, oh, yes, yes, here it comes, UUH, UUH, UUH, UUH, UUH, uuh, uuh, oh, oh, yes, wonderful, mmm, oh, Cal, you make me so happy. Thank you, dear," and I gave him a big kiss as I flexed my pussy around him still inside me.

I was wondering what, if anything, Gene had in store for me as I got up off Cal and lay down next to him.

"I've got the hot tub ready," he announced. I looked over at him and it looked like he had more ready than just the hot tub. Mmm, how nice.

We all got into the tub, it was just right, just nice and warm like I like it, not too hot. I sat between my fellow contestants, a cock in each hand.

"Oh, this is nice. And, look what I have. Two of my favorite things."

"Well, mine would like to be inside you rather than in your lovely hand," Gene said, so he stood up and knelt down in the water in front of me as I spread my legs for him. He got up close and I could feel his cock push right up against my slit. I reached down to spread myself and he pushed right inside.

"Mmm, oh, Gene, that is what a hot tub is for, fucking in warm water. Lovely."

"Fucking you anywhere, Rita, is pretty damned fine."

"I agree completely," I answered as he pulled back and forth.

I raised my butt up out of the water so Gene could get a better angle and, yes, it felt better right away. Somehow, the hot tub designers need to do a little more design work on what I believe is the most popular use for hot tubs. Just a suggestion. I would willingly be a test subject. Just think of all those engineers. Mmm.

As Gene fucked me, my right hand was rubbing Cal's cock which was showing interest in becoming more actively involved.

I put my head back as Gene went in and out, oh, yes, it felt good. I just surrendered to the wonderful feelings. He was nice and hard and when he started taking good, long strokes, it began feeling better and better.

"Mmm, oh, just like that, Gene, oh, yes. Is it good for you?"

"It's always good for me when I'm inside you, Rita. I just love fucking you."

"We both do, sweetie, we both do."

I lifted my legs up over his shoulders and he began fucking me direct and deep and it felt so good. Then, he just pushed in as far as he could go and I wiggled up and down which made his cock stay deep but move up and down just a bit. Oh, was my pussy a happy one.

"Oh, Gene, that is so good. Ew, just push in, oh, just like that. Here," and I moved quickly back and forth until we both had orgasms. We slumped into the warm water as Gene kept his cock moving gently inside me as we hugged and kissed.

We all got out of the hot tub and dried off and poured another glass of champagne.

"I'm ready, guys, who's next?"

They both said they'd wait a while and finish their bubbly so I sat on a nice, comfy stuffed chair and put my legs over the arms and they watched me masturbate until I had a nice, solo climax. Score one for Rita.

Chapter 2

Refilling my glass, Calvin asked if I was ready for a little sex out on the balcony. It was still light out and I was a bit apprehensive, not wanting to fall afoul of the law (I can just see my children coming down to bail out their mother), so went to look over the layout and decided that we could get away with doing it, though we may be seen by people on the upper floors of the building across the way.

So, champagne glass in hand, Cal and I went out and he lay down on the chaise and I swung my legs over him and lowered myself onto his cock, leaned forward and gripped the top of the back of the chair and began going up and down. My back was to the street but Cal could see across the building across from us. At least so far, we hadn't drawn a crowd.

But, I must say, the exposure of it all added a certain thrill to the proceedings which aroused me even more. Cal's hands and lips on my breasts were even more appreciated as we went on.

"Mmm, it's cool out here but this is such a nice way to keep warm. You really feel good in me."

"You're doing all the work, Rita, I'm just laying here enjoying it all."

"Yes, you do look pretty happy."

"Mmm, yes, and you've got me close to cumming, too."

"Oh, good, I'm close, too, this really feels good. Is anyone watching us?"

"I can't see anyone but I do think there was one window over there with people watching a few minutes ago."

"I'm waiting for applause," I said as I continued fucking Cal on the balcony.

"Oh, yes, it looks like three people at the window over there and, oh, for sure, they're watching us. The woman is even waving at us."

"Well, wave back."

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