Win or Lose Ch. 02

Some folks have been waiting a long time for chapter two. Thanks for your patience.

*****

It had been over a year since Janice made her bet with me that I couldn't last long enough to make her cum before I blew my load in her pussy. I lost twice the first night, and I lost every time since then, but I still held out hope that I could win. My prize? If I win my wife will, for the first time ever in our relationship, willingly suck me to completion and swallow my cum. My penalty? If I cum first, I have to go down on her and get her off with my tongue. In the process I end up eating all the cum I shot into her pussy.

Since that first night I have lost countless times and been 'forced' to eat the creampies I've made. Other than some slight wear and tear on my ego at first – both because of the frustration of my premature ejaculation and the disappointment of continually losing this running bet – it's not all a bad thing. First and foremost, we're now having sex practically every night sometimes two or more rounds, and have been for over a year! For a married couple in their fifties, that's pretty incredible in my book. Janice hasn't been a 'bad winner' at all. There are no cruel remarks about the way I always cum before she does. She doesn't try to make me feel like any less of a man for not lasting longer or for the willing way I slurp my juices out of her. She only teases me a gently about how much I like the taste. In fact, because gets so turned on even thinking about me sucking up a big load of my own ejaculate from her pussy, she spends most of her time in a very horny state. She's usually the one that initiates sex now, which is a big change from most of our earlier married life.

I have to admit that the thought of licking my own jism from my wife's cunt turns me on as well, partly because it's kinky as hell, but also because I've developed quite a taste for my own semen, and don't consider my 'penalty' much of a punishment anymore. A lot of nights the act of licking her clean after sex gets me hard enough that we go a second round. Even then I lose, but I don't really mind.

It's almost as if I need the taste and feel of my own cum in order to feel all the satisfaction that comes from a good orgasm. In fact, there was one that I almost won the bet – Janice and I climaxed together – and she told me I didn't have to eat my cum since it was a draw this time. I went down on her anyway. She was too sensitive in her post-orgasmic state for me to continue for long, but I did clean up most of my mess.

Further proof that I like the taste of my own cum is that when I do masturbate – which really isn't that often any more – I always catch it and lick it off my hands, savoring every droplet of tangy goo that my nuts produce. Most of my jack-off sessions these days are done while watching porn videos that involve some kind of cum play. My favorites, naturally, are the ones where the guy dumps his load in the girl's cunt and almost immediately goes down on her and licks it all up, but I also enjoy the ones where the girl sucks him off and then 'snowballs' it back to him in a messy kiss.

Even though I love seeing a creamy load getting licked up as it oozes from a freshly-fucked vagina, I'm actually turned off by the videos that feature a cuckold being forced to clean up after his 'hot wife' has fucked her 'bull' and been creampied. I suppose it's the humiliation that makes my dick wilt. I'm certainly not turned off by the idea of licking another man's cum out of my wife's pussy. There are a rare few videos out there where one man creampies the girl and the other guy willingly does clean up. I cum really hard when I watch one of those, but even though that would be hot, I doubt Janice would ever go for such a thing.

Maybe some folks would be disgusted that I actually like the taste of my own cum as it oozes from her freshly fucked pussy. I wonder if any of those people, especially most men my age, can say that they are having as much sex as I am. I think not. I'm sure that a lot of women out there can't brag that their husband always makes sure they cum. Perhaps the only complaints I could lodge are that I still haven't been treated to the delights of a blowjob where my wife willingly swallows all my cum and that Janice adamantly refuses to kiss me after I've gone down and cleaned all my cum from her pussy.

That's the only part of our sex life that's been frustrating – trying to win this running bet with my wife. I've tried lots of different things to delay my own orgasm, but none of them has really helped much. I tried eating Janice's pussy before I fucked her, hoping that she would cum quickly once I entered her but I would get so excited licking her tasty lips and sucking on her swollen clit that I couldn't hold back once my over-eager rod slid into her creamy depths.

I also tried various desensitizing creams, but they were universally disappointing. One of them made me so numb that my hard-on totally wilted. Another cream I tried helped me last a bit longer, but I still came too soon, and it tasted so absolutely vile that I had to resort to using my fingers to bring her to a climax. Janice and I were both frustrated that night, she loves the orgasms she has when I'm sucking my own cum from her pussy, and I love the taste of our combined juices so much that I've wondered at times if I really want to win this bet.

I even tried Viagra. The result was that I 'lost' four times that evening because I remained hard even though I still came too quickly. Both of us were sore the next day from all our gymnastics the night before. I still have a few of the little blue pills, which we save for special occasions and times when neither of us has to work for several days afterward.

As I studied on my situation, there were three things that seemed to be the keys to holding back my orgasm:

First, Janice loved to talk dirty while I was fucking her. Since the first night of our running bet, she's been a non-stop flood of dirty words; most of them are variations on the theme of me licking my sticky white load out of her overflowing quim. She says it a thousand different ways while I'm fucking her and every one of them causes my balls to tighten and spew their contents into her.

Secondly, she's found every place on me that she can reach and make it hard for me to control myself. Whether that's raking her hands up and down my sides where I'm slightly ticklish, or a sneaky finger finding its way to my butt crack, or the way she gently bites my nipples, Janice does everything she can to break my concentration and make by balls unload.

Finally, there's the whole issue of not being able to restrain my ejaculation once it begins. I started researching ways to do that and there turned out to be fairly simple solution; so simple that I couldn't believe it. A cock ring! After looking around at the local adult bookstore one Friday when I was off from work, I settled on the type that has two elastic cords with beads that can be moved up and down to control the tightness. That also made removal much simpler.

I brought it home at lunchtime. Since Janice was still at work, I knew I had the entire afternoon to myself and tried out my new toy while watching a porn video I picked up at the same visit. (Yes, the video featured men eating creampies, mostly their own, but a couple of scenes featured men willingly cleaning up after another man.) I stroked myself, sometimes quite vigorously, during the entire two-hour video but didn't spill a drop of cum.

When the DVD ended, I backed up to the final scene again, and just as the male star began to lick up the cum he had pumped into the woman's pussy, I released the cock ring and immediately came. That was one of the most amazing orgasms I've ever experienced. It was also the biggest and most powerful load I could ever remember shooting. Most of the first two shots went over my head splattering noisily on the hardwood floor behind me. The next few streams landed on my face. The rest of the jets, and I swear it felt like a dozen of them, painted my upper chest and my belly. I was covered in my own cum. Yes, I scooped up a lot of it and eagerly drank it down. I truly am addicted to the stuff. I decided that I would surprise Janice with the cock ring later, after I'd had a chance to replenish my sperm reserves. It was also going to take a little preparation so that all the obstacles to my outlasting my loving wife could be overcome at the same time.

I got everything cleaned up and put away and was firing up the grill when Janice came home that evening and we enjoyed steaks with some grilled vegetables and a nice bottle of wine. That night we made love like we usually do and, thanks to her squeezing pussy and dirty mouth, I was quickly on the edge of an orgasm. When her sneaky finger teased its way down my butt crack, I lost again. I was so drained from the jack-off session earlier that day that there was very little of my own taste to be found when I went down on her. I was almost disappointed.

I was gone most of the next week, travelling for work. Though Janice and I engaged in a little phone-sex-style teasing each evening, we didn't let ourselves get off from it. We had promised each other to save it for when I got home. Our phone call on Thursday night was hot enough that we almost didn't keep that promise with each other.

We were telling each other, in detail what we were going to do to each other when I got home, and Janice was taking her dirty talk to new heights. "I want you to have a huge load for me," Janice moaned in her sexiest voice. "I want you to flood my pussy with so much cum. Ooh, you're gonna love cleaning up the huge mess you make in my little cunt."

"But what if I win, baby?" I teased right back at her. "What if you have to suck my sticky cock and drink down the huge load of sperm I've been building up?"

I had been stroking my erection and I know she had been rubbing her clit while we talked. When I mentioned that she might have to swallow my load, I could hear her breathing get really erratic for a moment and I was pretty sure she'd had to fight to keep from cumming. Was she that turned on by the thought of taking my cock straight from her wet pussy and drinking down my semen? I had to pull my hand away from my rod and fight that same battle myself at the mental image of my wife's beautiful mouth being flooded with jism. My cock was throbbing and my balls were drawn up tight. I could feel my prostate readying itself to squeeze and send its potent mixture rocketing out to spray onto my belly. It took an almost superhuman effort, but I held back.

After a moment of listening to each other's hard breathing, Janice groaned. "Whew! That was close."

"Yeah," I muttered. "I almost had a mess to clean up, myself."

"Would you use a Kleenex or would you just eat it? Janice giggled. "I know how much you love the taste."

"Go ahead and smirk," I told her. "You're the one that's going to be tasting this load, not me."

"You're all talk, honey," Janice poked back. "Your win-loss record is proof of that. Plus, you haven't cum all week, so you'll be lucky if you even get your hard-on inside me."

"We'll see," I said. Janice didn't know what I had in mind for when I returned. She'd find out soon enough.

We said our good nights, and I promised Janice that I'd keep her posted on my travels, letting her know when I got to the airport and when I was on the plane. She said she'd pick me up at the airport.

My flight was delayed and didn't arrive until well after midnight on Friday night, so both Janice and I were exhausted by the time I got home. We curled up together beneath the blankets and slept soundly. I woke up alone in our bed, the smell of coffee telling me that my love had started breakfast. My dick was rock hard, and this wasn't just morning wood. I was used to having sex with Janice on a daily basis and now that I was home, I was ready to make up for the week we'd been apart.

Tossing the covers off my nude body, I glanced down at my eager member. "Patience, big fella," I muttered. "Tonight, you're pumping yourself out into her mouth. Now, settle down. I have to pee."

Once I got the bathroom issues resolved for the morning, I threw on my robe and headed down the stairs to greet my loving wife and start the morning. Our Saturday was a relatively lazy day, we worked in the yard before it got too hot, had our showers – separately, as Janice didn't want to risk having a quickie and spoil the 'main event' that was coming later. We went out for lunch, did a little shopping while we were out, and then took it easy around the house. After a light dinner, I started kissing Janice to get her in the mood and she soon took me by the hand and led me to the bedroom where we stripped each other and crawled into bed.

Earlier in the evening, I had slipped away and put on the cock ring I'd bought so I wouldn't have to fumble with it later and give away the surprise I had planned for Janice. I didn't pull it any tighter than it needed to be to stay in place around my flaccid cock. I could easily reach down during foreplay and tighten it once my erection was up to full size.

I keep her dirty talk to a minimum by kissing her. I also held her hands above her head so she couldn't probe any of those sensitive spots. We moved through several positions that night. I think the one that pushed Janice toward her climax the most was when I was banging her doggy style and rubbing her clit. The one that sent her over the edge, however, was when we got back in the missionary position. I slipped a pillow under her butt to raise her hips up more, and then I threw her legs up over my shoulders and pounded into her as fast and hard as I could.

I didn't have much trouble keeping my wife's dirty talk to a minimum at that point. She was too busy screaming out as her orgasm crashed over her. Her contractions were so strong at that point that I had to pull out of her pussy to keep from cumming myself.

Slipping down between her legs, I sucked hard on her clit and she wailed again as her orgasm, or maybe her second one, ripped through her. She went limp after that.

My hard-on felt like it was going to explode, but there was no cum pouring from me. I continued to hold Janice's hands above her head as I crawled up to kneel beside my wife. Janice looked as if she might cry when I lifter her head and guided my throbbing erection up to her face. It was slick with her creamy pussy juices, which were also dripping from my aching balls. As she took my turgid rod into her mouth, I reached down under my ball sac and unsnapped the cock ring. Just like it had when I'd masturbated, my load instantly jetted into Janice's mouth. The forcefulness of those ropes of cum, and the huge amount of it that I was blasting into her mouth surprised her. Her eyes flew wide open in panic as I shot stream after stream of jism onto her tongue. I'm sure she would have pulled away if I hadn't gently held her head in place as I emptied my balls into her mouth. The cum soon overflowed her mouth and streams of it flowed down her chin and her jaw, creating a sticky puddle that soaked into the pillow beneath her head.

I released my grip on her head and hands and fell back onto the bed. To her credit, Janice didn't immediately jump up and brush her teeth. She didn't even appear disgusted by the taste. Neither did she appear angry with me. Instead, my loving wife curled up beside me and gave me a big kiss. The cum that had missed her mouth smeared our faces and its heady smell flooded my nostrils about the same time that she pushed a big wad of my own cum into my mouth. She hadn't swallowed my whole load and now she was sharing it with me.

"Looks like you won," Janice giggled. "But since you like the taste more than I do, I thought I'd save you some." I happily accepted the semen she had pushed it into my mouth.

"I love you, Janice," I whispered when we finally broke our kiss.

"I love you, too," she cooed as she snuggled against my shoulder.

Janice reached down and petted my wilted cock. "What is this thing?" she asked.

I explained that it was a cock ring, and was meant to hold back my ejaculation.

"It did its job," she said, breathlessly recalling the flood I'd caused in her mouth, "but those strings and little beads really did a number on my clit. I've never felt anything like that!"

"You don't think I cheated by wearing the cock ring?" I asked.

"Maybe, but since you made me cum so hard, I can forgive you," Janice purred as she settled in against my side.

I was almost asleep when she lifted her head and whispered in my ear. "Is the bet still on?"

"Do you want it to be?"

"Sure," she giggled. "After all, you can't win 'em all."