Never Bet with Your Ego

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Man lets his ego dictate and makes a bet he may regret.
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Part 1 of the 2 part series

Updated 06/08/2023
Created 05/31/2016
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ShinyPaul
ShinyPaul
24 Followers

Chapter 1

"Really, You would with Sandy"? she asked. We'd been engaging in a rather heated session and Chrissy my wife of 22 years had been asking me about people I fantasised about. In my aroused state I'd just blurted out the name of her best friend and was now inwardly cringing and wondering how much trouble I was in store for.

"Well" I said, "I don't know why I said it dear, she was just the first person that I thought of". "Oh come on, I've seen the way you look at her sometimes when you think I'm not looking, It's quite obvious you have a little bit of a thing for her. I don't really think you're her type though".

Male pride or ego I don't know what it was, but I bit and had to ask. "What do you mean, I'm not her type"? Now I'm no male model, I'm a little over 6ft tall, keep myself in good shape and like to think I'm good company and make women laugh. I'd always got on well with Sandy and on certain occasions had flirted a little with her and she seemed to reciprocate, unless It was just my imagination. As wives best friends go she could have been a lot worse, especially when I heard some of the stories my friends would tell me about their partners friends.

As I mentioned earlier Chrissy and I had been married for 22 years and together nearly 25. We'd both been virgins when we got together and had always had a fairly active sex life, we both knew what each other liked (or thought we did) sexually. Chrissy was still a knockout and had a fantastic figure and legs that I still caught men 20 years younger checking out regularly. She very rarely initiated sex, this was virtually always left up to me and a lot of the time if I'm honest it did feel a little like she felt she was performing a duty and going through the motions.

"Oh, I think she'd eat you for breakfast. You should hear some of the stories she comes out with on our girls nights out". "Oh I don't think she'd have any complaints" I said. "I am very interested in hearing some of these stories though". I'd heard a few of the stories myself at dinner parties and summer BBQ's when a few too many drinks had been consumed and tongues had loosened. But I was well up for hearing some more.

"Oh I don't know if I can, us girls like to keep each other's secrets. How would you like it if I told her all about what we get up to"? I didn't dare admit to her I'd actually quite like it if she did and adjusted myself slightly just in case I got aroused at this line of conversation. "Oh come on, you can't do that to me. Just tell me a couple of little things". I could see her struggling with the idea and biting her bottom lip, "Well I guess I could tell you a couple of things but then it would only be fair for me to tell her a couple of things about you in return" I could feel my arousal growing and made to move like I was uncomfortable and rearranged the bed clothes to cover the swelling that seemed to be starting in my groin. Before thinking of any possible negatives I'd said "Seems fair enough to me, tell her whatever you like"

She looked me in the eye, "Ok then, well where do I start and what do I tell you that won't get you overexcited" This sounded good to me and I was beginning to hang on every word. After a brief pause she started "Well she likes big men, that's one thing I can tell you" This seemed a little tame, but I guessed she was just getting warmed up. I also felt a sense of excitement as I was a big guy and maybe she would like me? I couldn't help but blurt it out, "Well I'm a big guy, you think she'd like me"? "No, no, you don't understand. She likes men who are really big, you know, down there" she said motioning with her eyes towards my groin. Her eyes stopped for a second on the sheets covering my dick before returning to meet my eyes. "Well I said, I don't think I'm too badly endowed in that department. You've certainly never had any complains" I couldn't help but add a little "have you"? on the end.

She broke eye contact "Of course not silly, we do ok, and you're really good at other things anyway" This was the first time I'd ever detected any sense of dissatisfaction, Maybe I'd just grown complacent and maybe I'd read too much into her comment about being good at other things and her not wanting to meet my eye.

"I just don't think she'd go for someone like you, some of the men she talks about sound huge and I think she must be exaggerating or just confuses inches with centimetres"

"I'd do fine I insisted maybe a little forcefully, there is no way she'd end up unsatisfied with me". "Ooh, hit a nerve did I" she said with a slight smirk on her face. "Anyone would think you were protesting a little too forcefully to overcompensate for something" and grabbed for my dick under the covers. Her eyes went wide when she felt how hard I'd got after only just finishing the deal a few minutes before. "You little pervert, this is turning you on isn't it" I smiled a little awkwardly. "Sorry, don't get upset" I said. "It's all just fantasy and I'd not really ever do anything, well not without your blessing" She grabbed her pillow and hit me with it. "Ha ha, very funny, But I know you'd not be able to satisfy her with that" and pointed at my now twitching dick. "She'd probably laugh you out of the room"! My ego was taking over "Well I beg to differ, I'd bet you whatever you want to bet that I could". She raised her eyebrow and was quiet for a few seconds. "You'd bet whatever I want"? My mind started to race, was she really considering this? "Um, yeah. Sure. How about a $2000 handbag" every woman seems to fantasise about those these days. "Nah, not really my style. I guess if it's good enough for you then it's good enough for me. If you can't make her cum then I get to experiment with one of her past conquests and see if they are as good as she says".

I was a bit taken aback by this "Wha, what"? I managed before trailing off. "ha ha, you should see your face. Worried are you"? I quickly regained my composure, it wasn't like this was ever going to happen anyway! "If that's what you want, then go for it" I said and held her gaze for what seemed like forever but must have in reality been only 3-4 seconds.

"Want me to call her right now"?

I didn't really know what to say, was she testing me? I struggled to keep eye contact, It's not like Sandy would say yes anyway. Would she? I couldn't make myself say the words, I just kinda pulled a strange face and shrugged the one shoulder I wasn't leaning on.

She looked down at my groin, "you might as well go and sort that out, I've got a phone call to make". And with that she jumped out of bed, grabbed her phone and went and locked herself in the bathroom.

Chapter 2

"Hello"?

"Hi Sandy, It's me"

"Hey girl, How's it going? What's the matter you sound... Excited"??

"Well, I've just spent an hour in the sack with my husband"

"Ooh, lucky girl. I've not had any for a couple of weeks. You trying to make me jealous"?

"Would I do that? Hey we're best friends and I was always taught to share"

"Well what time you want me round girl? Haha"

"To be honest I don't think he could go again so soon, he can't usually. Although he was quite excited by what we were just talking about"

"Ooh, now you've got me interested. What's with this sudden phone call and excitement"?

"Well we were kinda right in the middle of it and talking sex stuff and he admitted to fantasizing about you, the dirty little sod"

"Aah, really. Aw, that's kinda sweet if slightly awkward! But hey who can blame him, I'm not too shabby you know"!

"Oh yeah I know, but the thing is our convo kinda escalated and he ended up betting me he'd be able to satisfy you, you know sexually..."

The phone was silent for a few seconds

"Are you kidding me? I mean it sounds like you want me to fuck your husband! I mean I'm a game girl but I don't want to go and ruin our friendship over a bit of dick"

"Well the thing is, we've only ever been with each other and it's kinda like going through the motions sometimes. I've wondered about other men especially when you tell some of your stories and he made a little bet with me"

"A bet? What kind of bet"?

"He bet he would be able to satisfy you, but if he failed that I could maybe have sex with someone else. Maybe someone you could recommend who is ... You know. Hung"

"Well I sure know a few of those, I love me a big dick as you well know. So tell me, Paul's a big guy. Is he big all over"

"Oh Sandy, you are so bad! He's ok I think, It's not like I've ever gone to bed with a tape measure or anything. And he's the only guy I've ever slept with"

"I can't believe you don't know how big your own husbands dick is Chris, I'm pretty good at that sort of thing. I can usually guess to within half an inch just by looking at a hard one" "I've even made an excuse or two if they look too small, or maybe "Accidentally" finished them off with an overenthusiastic handjob" "The thing is do you think he's going to be able to satisfy me, because by the sound of your arrangement if he does it means you have to go without"?

"Well, I don't really know to be honest. He hardly ever makes me cum. Not with his dick at least. I've gotten into telling him my favourite position is the reverse cowgirl. That way he doesn't see me with my hand down my panties rubbing myself off.

"Aah, you're a hook your panties to the side kinda girl huh. Haha, A girl after my own heart"

"Well kinda, he has a thing for satin panties so if I wear them he becomes transfixed on my shiny butt rocking back and forth on him and doesn't even notice me flicking away like crazy to bring myself off. Come to think of it he actually congratulates himself sometimes on his prowess when I cum and start bucking on him.

"So for this to work it means he needs to NOT make me cum? This sounds like a bit of a shitty deal for me to be honest, haha"

"Yeah, well I guess it is a bit difficult to sell something like that. But you know what maybe we could trick him somehow. I'm not 100% sure but I don't think he realised I meant he had to make you cum with his dick alone. No oral allowed as he's very good at that"

"Hey Chris, I'm only teasing you, what are friends for eh? I'm sure I can take one for the team. In fact I'm gonna go all out to have him cumming as soon as possible so you get to sample some monster cock" "You're gonna have to tell me a few things that get him off tho. You've said about the panties which has already given me an idea but I need to know a few other things he likes, to see if I can't speed him along a little"

"Shit, I'm sorry but my phone is about to die. I'll call you back after I've given it a charge and let you know some dates times and let you know what to wear for maximum effect"

"Ok Chris, I was just on my way out anyhow. I'll speak to you soon babe, Bye"

To Be Continued...

ShinyPaul
ShinyPaul
24 Followers
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  • COMMENTS
13 Comments
EzrollinEzrollinabout 6 years ago
Nice start!

Nice start for a two-part story, captured my interested and well written other than a few errors. If I find a story interesting enough to read it through, it gets at least four stars...believe me there's been a few I didn't get past the first few paragraphs.

Tootight1Tootight1over 7 years ago
good story

why, because it shows how not to have a marriage. A wife that smirks at your package, then makes a bet so that she can play around on you. She is holding all the cards. She knows everyone involved and he doesn't. He has to initiate all the sex, then she says he has other talents instead, yes, like a nice pay check, or bank account. Finding out all this in one night, wow, and he is still stupid enough to go through with it. How dumb is this guy? Love is : giving your self to your partner for their happiness, and vice versa. I don't want to read the next chapter, but you know I will.

chytownchytownalmost 8 years ago
Good Start****

Very entertaining read so far. Looking forward to next submission. Thanks for sharing.

amyyumamyyumalmost 8 years ago
Cute & original

Now don't fuck it up -- and be sure to use more paragraphs! 5* from me so far.

amischiefmakeramischiefmakeralmost 8 years ago
Why did I rate this a 5?

The story is poorly written, and you have to stop putting quotes from two different people in the same paragraph. However, it is original and the thought of what could happen intriguing, so I gave it a 5. I guess I'm a perv.

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