Win or Lose - Cover

Win or Lose

Copyright© 2014 by OldBillyBob

Chapter 1

Erotic Sex Story: Chapter 1 - Here's the bet: If he can outlast her and not cum before she does, she'll suck him off and swallow. If he loses, he has to clean up after himself.

Caution: This Erotic Sex Story contains strong sexual content, including Ma/Fa   Consensual   Romantic   Heterosexual   Fiction   Oral Sex   Cream Pie  

I guess it's a case of 'be careful what you wish for' but I'm not really complaining, since what I wished for, ultimately, was a better sex life. I certainly got that, but it wasn't exactly what I thought it would be when I was wishing for it. My wife, Janice, and I have been married for a long time and during all our years together she's never, willingly swallowed my cum. I've gotten lots of blowjobs, but she's always pulled away at the last instant and finished me off by hand.

At one point, early on, I tried asking, that turned to begging. When begging failed, I tried stealth Ð not giving her any sign I was cumming Ð but when I exploded in her mouth, she would jump up from the bed, run to the bathroom and spit in the sink. After she'd brushed her teeth, she came back to bed and turned off the light. Our night of fun was finished. It was a couple of months before she offered to suck me again and I knew I'd better follow her rules or it could be the very last time her mouth was on my dick.

Don't get me wrong, we've always enjoyed sex and neither of us would go outside our marriage looking for whatever might be missing. Even after all these years, we still talk easily about fantasies, little variations we'd like to try, etc. During one of these pillow talks several years back, Janice expressed her frustration that I didn't last as long as she wanted and that she was often left 'high and dry' when I shot off, wilted and rolled off her. When we were both younger, she said, this wasn't a big problem, since I could usually keep a hard-on and fuck her long enough to satisfy her. Now that age is starting to catch up with me, she felt that frustration beginning to build as I became more and more of a one-shot wonder. After that I was careful to remember to help her reach her own climax. Mostly that involved masturbating her sopping pussy with my fingers until she came. (Janice had never been able to reach multiple orgasms in all our years as a couple.)

This whole routine, brief sex until I climaxed and then stroking her pussy until she reached hers, worked pretty well for a couple of years, but one night she just couldn't get there, no matter how skillfully I manipulated her clit. As my hand was starting to cramp and I was thinking, 'Just cum, baby. Hurry it up!' Janice grabbed my wrist and pulled my hand away from her mound.

'This isn't working, Rob, ' she whispered. 'What I really need is your tongue there.'

'No way!' I protested. 'It's 'lick then stick', not the other way around'

'But Rob, ' she whined. 'I need to cum, and your mouth is so talented, and it's just what I need.'

I continued to protest. I really wasn't keen on licking my own cum out of her, as most men aren't. Our fear of being turned into gays is probably the reason. Janice rolled away from me at that point and I knew our nighttime frolic was over.?

A couple of days later as we were going to bed, Janice seemed a bit nervous about something. I asked what was wrong and she muttered that it was nothing. When we got under the covers, she turned to me and kissed me. It was a very hot kiss. Janice was on fire. She moaned when I kissed her taut nipples through her nightgown, and then pushed me away briefly while she sat up and pulled it over her head. Taking her hint, I discarded the t-shirt and boxers I usually wear to bed and rejoined her under the covers.

As we kissed, Janice began to moan and thrust her hips against me, making motions like she was fucking me Ð and this was only shortly into foreplay, which I know she likes to last a while! She broke away from our kiss, panting.

'Rob?' she breathed. There was a bit of that nervousness from earlier mixed with the arousal she was showing. 'I want to try something a little different.'

I assured her I was up to a little something new and asked her to continue.

'I want to make a bet with you.'

'A bet? What kind of bet?'

'Well... ' she stammered. 'I know how you've always wanted me to swallow when I suck you off and, well, I was thinking... '

My cock throbbed as the mental movie of her swallowing my cum played in my head. Janice reached down and felt my cock. My balls were drawn up tight. I think if she'd put my overexcited cock in her mouth at that moment, she'd have been swallowing in no time.

'What?' I urged.

She started to talk fast, as if she had to say it all at once or lose her nerve entirely. 'I'm going to bet you a complete, and I mean totally complete Ð swallow and all Ð blow job if you can outlast me.'

'Outlast you?' I was puzzled but it soon sank in. 'You mean, if you cum before I do then you'll suck me off and swallow?'

'Yes!' she beamed wickedly at me. 'In fact, I'll pull you right out of me and finish you on the spot. Kinky, huh?'

'It's a nice kind of kinky, ' I assured her. 'But what if I lose?'

'You'll see.' she winked. Rolling on her back, she spread her legs and pulled me toward her. 'Now get in here and fuck me.'

I slid into her with one thrust and she arched her back and drew me in even deeper, wrapping her legs around me and digging her heels into my butt as if to spur me into action. I began to thrust into her, slowly at first, trying to pace myself, since Janice's not known for cumming quickly. Tonight I thought I might at least have a chance, as she seemed so aroused. Despite how wet and loose she was, her walls still gripped my shaft as I plunged in and out of her. When I bent my head to suck on one of her nipples, which was so hard it had wrinkled itself into a big pink prune on her breast, I could feel her squeeze me. That, combined with the way she rolled her hips and the mental movie of her pulling my shining wet cock from her pussy and sucking my load down her throat, made me blast off inside her without warning.

'Looks like you lost, ' she smirked at me when I opened my eyes. 'Now for the consequences. Roll onto your back.'

I rolled off Janice and she snuggled up to me, whispering sweetly in my ear, telling me to close my eyes and relax. 'Trust me, ' she cooed. 'Now, put your hands over your head.

I complied. I think I was in a bit of awe that Janice was so assertive this evening. Usually, she's not the instigator in sex, but this was apparently a special sort of night. I realize now that it was the turning point in our sex lives and there's been absolutely no going back. When I'd put my hands back over my head, Janice quickly produced two pairs of handcuffs from her bedside table and secured me to the wrought iron headboard.

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