Some bets are worth losing


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Tags: oral, relationships, public

Added: 27 Nov 2012 Views: 5941 Avg Score: 4.88

A bet with a sexual prize is finally won a year after it is made.
Don’t get me wrong - it’s not that I’m not normally a competitive person. I am. Sports, business, gambling, hell even playing chutes and ladders with my nephews I always want to win. So I absolutely am competitive. It's just that whenever I get together with Sherry, those competitive juices go into complete overdrive. To be fair, she's the exact same way with me, and this often makes our relationship - well, let's just say interesting.

On those occasions where we run together we might start out at a casual gate, but by the end we're sprinting so hard that it takes about ten minutes before we can speak without sounding like we're going to hack up a lung. Friends have been known to invite us both to dinner and ask us each to pick up a bottle of wine, and then casually mention that the other is picking one up as well; they know we'll both bring something both amazing and overly expensive, each vying to be told ours was the best. I once lost my shirt (both figuratively and literally) to Sherry in a ridiculous poker hand because I refused to fold first.

We’ve had some very loud discussions about the rules of darts in bars.

We first met two years ago, when her roommate Cheryl invited me to a party at their apartment. I'd gone because I had a bit of a crush on Cheryl and had been hoping to get her alone for five minutes, charm her with my dazzling array of unfunny jokes, and get her to say yes to dinner after one too many glasses on wine. So I brought a lot of wine with me, and presented the bottles to Cheryl in the kitchen. At her request I began to open a few for the guests.

"What the fuck is that?"

I turned and saw a half dozen or so people at the kitchen table, playing poker. I was a little taken back with the woman who had asked the question. She was right about Cheryl's age, late twenties, and her thick auburn hair seemed to exist for no other reason than to accentuate her emerald green eyes and her perfectly tanned and unblemished skin - and quite a lot of skin there was. It was the middle of both January a cocktail party, and yet she was wearing khaki shorts and a wife-beater that was clearly a size or two too small. Her "outfit" left no question as to what that body would like naked, and what that body would look like naked was perfect. I was instantly smitten.

"I said what the fuck is that?" she motioned with her hand to the bottles I'd placed on the counter.

"Um... Wine?" I tried, unsure of her meaning.

"Yeah, well let me know when you're ready to start drinking like a man," she drawled, lifting a half-full bottle of Basil Hayden. She did it with a grin, and looking back it was the grin that got me: playful, sexy, full of illicit promises - that grin was the downfall of angels. I left the wine and my hopes for Cheryl behind, pulled up a chair and a shot glass, and began to drink in the Basil Hayden and her citrus-musky scent. It was only 6:30 at night, and she smelled like the promise of sex. I got hard just talking to her. Half an hour later we were in the stairwell, her shorts at her ankles and her hands braced against the wall. My hands clutched at her hips as I pushed deep inside of her. Her attempts to be somewhat quiet made her moans sound like growls, exciting me and making me thrust that much harder. When she came it felt like a wave hitting me. I pulled her back to my chest, and found I too was exploding. I bit her shoulder to keep from yelling out, and I can still taste the saltiness of her skin at that moment. We stood there for a minute or two, her leaning back against my chest and me still hard and inside of her. When she finally spoke it was with a breathless, almost far away voice.

"Where do you live?" she whimpered. I told her. "Wait here. I'm grabbing my purse, and then we're going to your place and we're going to do this again a few more times. Don't leave."

Like I was really going anywhere without her.

As we began to see each other over the next few months, three things became clear: We were better as friends than as a couple, the sex was athletic and inspiring, and - as I said before - whenever we competed, we competed to the death.

And you need to know that to know this:


"Have you ever been a selfish lover?"

We were sitting at a downtown bar drinking Manhattans. It was a Tuesday evening and each of us had worked late, agreeing to meet for a drink in that bar nether-time that occurs between Happy Hour and the after-dinner crowd. She was sipping her drink and looking out into space; the fingernails of her other hand were under the table, leisurely tracing the outline of my cock.

"Sure," I answered. "I think everyone's a selfish lover to some degree."

"No," she shook her head, but her eyes were still somewhere far away. "I mean, totally 100% selfish. Have you ever been that?"

"I've cum before my partner, yes."

She finally turned and looked me in the eyes, all business. Her hand came back to the top of the table, I noticed sadly.

"Even then you're not really selfish, you're still working to pleasure the other person. What would it be like to just sit and be pleasured with no concern at all for the other person? Would it be amazing, or would it be dull?"

I smiled. "I think what you're describing is a blow job. And yes, I've had those too."

"Not the way I'm thinking, you haven't. Or at least I don't think you have. Admit it, when you get a blow job, part of you is thinking about what you can do once its over to repay the blow jobber, right?"

" "Blow jobber?' "

"You know what I mean."

I thought about it. She was right. Sex is always both the yin and the yang, even in the privacy of our own heads.

"I think we should do an experiment, where we try being a selfish lover just to see what it's like." She was talking faster now, her mind clearly on a track it was not going to leave anytime soon. "You wanna do that?"

I shrugged. "Sure, but who gets to be the selfish one?"

"Both of us. One will be the selfish one tonight, the other will get to be selfish next time."

I shook my head. "No, because then it's not really that selfish if we both get to do it. It's just a trade over time."

She thought about this for a minute before concluding, "You're right. Only one of us can ever get the selfish experience, and then they'll have to tell the other what it's like." She slapped her palm against the table, her mind made up. "That's what we're doing. Oral sex, one gives, the other cums, and we say goodnight."

"I thought we agreed neither of us had time to play tonight?"

"We won't need time," she grinned. "Pants down, hard hat on, go to work for a bit, and we're done."

I cocked my head. "So let me get this straight. You want us to finish our drinks just early enough so that one of us can sit slug-like while the other gets us off. You're thinking of all the things we might do in the next half hour, the best option is for one of us to sit and be the Jabba the Hutt of sex."

"Please?" And then she flashed that grin, and it was over. It didn't really sound like great sex, but it did sound better than no sex and so I nodded.

The question, of course, was who got the plum job and who was sent to work in the mines. We play-argued for a bit, and the she yelped a little too loudly, “Let’s bet!” A few of the people sitting near us glanced over. "Loser has to pleasure the other orally and get nothing in return - in fact, they have to agree to go without sex at all for a week after." Many, many more people turned and looked.

Of course, we never figured out a bet that we were willing to make. Like I say, we're just too damn competitive. Sex is sex, but neither of us wanted to lose. Eventually we decided to table it for another time. As we finished our drinks her hand disappeared again under the table. There were more than fingernails this time, and the movement was more purposeful. Nearing the inevitable, I whispered, "Careful, or I'll really cum."

She looked me in the eye and said, "Good. I want to watch you try to keep a straight face when you cum." And then came the grin, and of course the grin finished me. As I tried to put my overcoat on in a way that would hide my bulge and the newly wet spot on the front of my slacks I said, "Wait - wasn't that selfish?"

She shook her head as she pulled her own coat on. "Not at all."

"How come?"

She leaned in and lowered her voice. "Because now you're going to walk me to the parking garage and we're going to get in my car and you're going to show your appreciating by fucking me."

And appreciative I was.

Under her skirts, as my hand would discover when we got to her car, her upper thighs were already slick. They were so wet and so hot that I knew before my fingers finished their slow trip up her legs that I would not find panties. And hey, yin and yang, right? So as we made out in the dark of the bucket seats I repaid the favor in the bar with my own hand. She threw her head back and cried out when she came, and by that time I was hard again. I pulled her over to the passenger seat and positioned her pussy over my cock. Now was not the time to be selfish, and making me come in the bar deserved a better reward than being fingered.

I held one of her ass cheeks firmly in my left hand. As she leaned down to kiss me I pushed up with my hips and entered her. She rewarded me with an amazing gasp. My right hand pushed gently at her clit as I moved up and down, slowly at first but eventually jack hammering up into her slick and dripping kitty. Her face was just inches away from mine, and I could see that her eyes and mouth were clenched shut as she grabbed my hair for dear life. She looked like she was trying to keep every bit of herself locked inside, and her moans became a constant, desperate humming. I was holding her ass up in the air with one hand, and realized her beautiful cheek was about to slip out of my sticky grip. I pushed up hard, and as her body went up I quickly flexed my hand and grabbed the cheek again. This time, however, I'd reached over farther than I had the first time, and as I closed my grip I could feel my fingertips had gone from being firmly on her backside to deep in the crack between her lovely apple shaped ass cheeks. I worked my middle finger around until I found the soft rise that marked her asshole.

Picking up the tempo with my other hand and my thrusting, I leaned my head forward until my lips were at her ear. My voice was low and husky as I began to growl, "Cum for me, baby. Cum for me. Cum on my cock. Come on baby, cum on my cock." I'd been with Sherry many times, and so there was no doubt where that cliff was. As she got closer to flying over, my fingers continued their work on her clit and the swelling of her anus; my voice faster and more guttural. As I felt her begin to fall, I pushed my cock up all the way inside of her and held it there; the finger on her clit was instantly replaced with the heel of my palm pressed against her pelvic bone. The finger on my other hand shot into her ass, as if trying to reach through and touch the other hand.

She exploded. Her eyes finally opened, wide, and her mouth ceased to clench and she let out long, loud yell. She shuddered, and her fingernails drew blood at the back of my neck. It lasted a while, and in the end she was slowly grinding on me, humming some song I did not know. This went on for about five minutes, her slowly grinding in circles on my cock as she smiled and hummed. I watched her, her hair now stringy with sweat, and realized for the first time that she was still wearing every piece of clothing she's started with - even her shoes. Like the first moment I saw her in her kitchen playing cards, she looked perfect. I smiled.

"Can I cum?" I asked.

"You may cum," she said, and grinned. And of course, the grin did it.


The Bet, as it came to be known, was one of those things often discussed but never acted upon. We just couldn't find the competition we both thought was fair. Then this past spring she started seeing someone that was better as a couple than a friend; this summer I followed suit with my own relationship. We wanted to stay in touch, but that becomes hard to pull off when so much of your shared past is sexual one. She heard about my girlfriend and sent me an invitation to a barbeque she and her boyfriend were having last July. "It'll be fun," she wrote in her email. "I know Dan would like to meet you, and I'd love to meet this Lucy person you're seeing." I wrote back and said that yeah, it would be fun, and we'd probably be there. But of course we didn't go. And life went on, because that's just what life does.

This past week I was surprised to receive an email from Sherry. The subject heading was The Bet.

She had heard from friends that I had recently broken up with Lucy, and she in fact had broken up with shortly after their barbeque. "It feels like too much moving on has happened, so I'm not proposing we go back to the way it was. But I do think we have one last piece of unfinished business."

Her alma mater, Stanford, was playing the number two ranked team in the country, and she wanted to put The Bet on the game. I don't know that much about American rules football, so I called a friend he does. "Take the bet," he said. "Oregon is a lock." Except, of course, that they weren't. They lost, and so did I.

I met Shelly for a cocktail a few nights later, and after some catching up she took me back to her place and put on some sultry blues. It's a funny thing to be intimate with a person you know you'll probably never be intimate with again, and so I took my time undressing her. It's hard to believe you could ever really forget a body like that, but I took the time to soak it in just in case. By the original rules set a year ago, I kept my clothes on. I took her by the hand and led her to bed, laying her down as I kissed her neck. Necks lead to breasts, of course, and breasts to stomachs. But they don't have to do so quickly, and so I took my time and savored each millimeter of salty, tanned flesh.

By the time my mouth had worked my way from her feet to her thighs, she looked as though she might have been asleep. She seemed perfectly relaxed, eyes closed, and though deep her breathing was slowed. I stopped for a moment to watch those perfect breasts fall up and down, hard nipples riding the crests of a gentle surf. Smiling, I ran my tongue to its intended destination. The heat and moisture that met me was the first tangible proof I had that wherever Sherry's mind was, her body - at least for the moment - was still very much mine.

I will spare you too much detail. She tasted like the most beautiful woman I had ever seen, and as my tongue gradually picked up it's pace so did her moans. I let my hands take in the curves of her body as I tongued her, letting my fingertips take their last snapshots of this body I had so often touched, and so often touched myself remembering. When she finally came, my shirt was drenched with her juices and my sweat. I glanced at the clock; thirty-five minutes had passed since I first kissed her neck. It felt good. I decided then and there that I was glad I lost the bet. For me, hearing her cum was my selfish gift to myself. And once I realized that, my next objective was clear. I moved up and kissed her gently on the lips, and then repeated the whole thing again. Twenty minute later when she came again, I had to eventually reach up and pry her legs apart slightly - they were crushing my head.

I got up and gazed at her lying there, her eyes still closed. I kissed her, whispered good night, and walked out of her bedroom.

"What the fuck is that?"

I turned and looked back into the bedroom. Her eyes were open, and she was propped up on one elbow.

"I'm sorry?" I asked.

"What the fuck is that - you tongue me and then you slink off like some skank? What the hell kind of lover are you?"

I walked back to the bed and smiled. "Rules. You made them, you made me promise to follow them not matter what. Remember?"

She grabbed my belt and began undoing it. ""Yeah, screw the rules. All I know is that I won, and you lost, and now I demand an evening of fucking you silly."

And I was about to object - I really was. But she grinned, and... well, you know.

[Note: This is my first post here, so any feedback, suggestions of criticisms would be most welcome.]