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She was CERTAIN she could not lose this bet. And, I knew that she felt that way. I also knew she was dead wrong. I knew I would win.
So, I shouldn't have... but, I did. I made the bet for the biggest things I wanted from her and could never get. Things she really didn't want to do. Regarding sex.
I know. I'm a bad husband. And, I shouldn't have let her honor her wager. But, she never welches on a bet. So, she kind of made me do all these things with her. I say "all" because the bet wasn't for one single prize. There were 5 prizes I won. Here they are, in no particular order:
1: One blowjob, no deepthroat, with a condom. Time and date jointly worked out.
2. Perform 3 new (to her) rear-entry into pussy sex positions. She had to initiate sex and use one position each time. The three were: a. magic mountain, b. a different position with rear pussy entry, presented as a surprise sex session and c. rear entry bent over the dining room table.
3. Anal sex, once Time of her choice, slow entry. I'm not huge, so not SO bad. (Easy for me to say)
4. Sit on my face, I eat pussy. Having her pussy eaten doesn't do anything for her, so we don't do it anymore, once I found that out. Actually, it's worse than not doing anything for her. If I get her fairly turned on by kissing her, sucking on her nipples, fingering her clit etc., then go down on her and start licking her pussy and clit, it actually kills the mood for her, deader than a doornail. She doesn't really know why, but it always does that. So, in my best interest, I don't go down on her. She didn't share that for years though. We can have sex afterwards, if she wants, in any position she likes.
5.Peg me. I thought after doing all the other things, she might kinda enjoy this, to "get back at me", so to speak. I was up to try it once, at least.
So, no threesomes, no 'fuck the neighbor while I watch', no bondage, masochistic shit, etc. FAIRLY straight-forward (from my perspective). I told her she really didn't have to do any of this, but she said "A bet is a bet and it's a one-time thing, so I can get through it. SOME of it, I might even enjoy, once we get started. Not the anal. That's just gonna hurt, I think."
Dinner is served
I guess she decided to get all these "tasks" over as quickly as she could and be done with it. The very next night, I came in for lunch and the table was set, but not the way it usually was. There was a spoon on the left and a dildo on the right. In the middle, was my very athletic, hot wife, wearing a bra with the nipples cut out, sexy stockings and a garter belt to hold them up, NO panties. She was lying on her back on the table with her legs spread.
"Are you ready for lunch?" she said. "It's hot and ready for you. The first course is: pussy pie, with strawberry flavored lube and whipped cream. No cherry. Gone long ago." My jaw dropped 2 feet and my eyes bugged out. This was a 20 year marriage, mostly missionary sex. This was NOT like my wife, at ALL! But, I wasn't complaining, to be sure.
"After the first course, if you like sir, you may fuck me from behind, on the table. Pussy only, please. Anal is not on the menu today." I nearly blew my load right there in my pants.
"Well, don't just stand there! You need to eat it while it's hot. If it cools off, I'm throwing it out...for good!" I immediately undid my belt, dropped my pants, socks and underwear, took off my shirt and pulled a chair up to the table between her legs. I could see she was shaking a bit from nervousness and excitement for what was to "cum". I started by applying the strawberry sex lube to her pussy lips, both inner and outer. It was a little cold so she yelped a little when my finger first touched her. Then, I leaned in with my elbows on the table and kissed around her inner thighs, all around. I kissed her mons above her slit, then worked my way down to her inner lips. They smelled of pussy musk and I pushed my face fully into her, flicking my tongue on the way in. She moved her hands down to each side of my head and guided my movements to give her the most pleasure (if this was pleasurable at all for her). Even if this wasn't a turn-on for her, at least it could be relaxing.
I'm sure she was planning and thinking about this all morning, so her pussy was involuntarily preparing for the sex surely ahead. it was very wet from my eyeball to pussy position, I could see that her pussy hole was relaxed and open just a bit, expecting and desiring cock to be slid into it.
I worked her inner lips and her clit hood, sliding a finger into her pussy hole a little. Then I tongued her pussy opening as far as I could penetrate. She seemed to react to this positively. Her breathing quickened a bit. I applied more lube directly on my erect cock, then stood up and touched it to her clit. She thrust up to meet me a bit and I pushed down, inserting the head into her love box. She moved her feet behind my butt and pulled to get me into her further. She didn't like oral sex, but she DID like to have a cock inside her, moving in and out!
I pushed in a little more, then she pulled me all the way in using her legs. I stopped there to let her pussy get accustomed to the fullness, then moved in and out several times. I didn't continue for long, because I wanted to cum in the rear-entry position so after just a bit, I pulled out and asked her to turn over. She grunted and reluctantly got off the table, then turned around, pushed the front of her thighs against the table edge and dropped her torso down to lie tits to the table. I rubbed her back some, then moved my hands around to cup the sides of her breasts. I pressed in with my very erect, lubed cock, up between her ass cheeks and slid up and down a bit.
Although she didn't want anal today, apparently she liked the feeling of this, as she pushed her ass up and back and gripped my cock with her ass cheeks. It actually felt VERY good to me also, but I wanted to be inside her pussy in the worst way, so I stepped back a bit and tapped her two ankles to get her to spread her legs. When she had done so, I dropped down a little and pushed my cockhead up into her wet hot pussy hole again. She was so wet from all the prior foreplay that I accidentally slid all the way inside, in one swift motion! She made a small grunt, but was quite ready for me, as she immediately clamped down with her kegel muscles around my dick and held me inside her. Her breathing had quickened considerably and she let out a little moan each time I pulled out and thrust back into her. I bent my knees a little and pushed up to hit her G-spot and I apparently did, because her groans became much louder. It didn't seem like she was mad for losing the bet at this point. Maybe for the other "payments", but it seemed she was THOROUGHLY enjoying this particular payment.
As I sensed she was about to orgasm (fairly rare for her, typically), I sped up just a bit, then pushed my lubed thumb into her ass half-way. It was right there in front of me, winking at me, pulsing tightly closed, then opening a little, just asking me to put a finger in it.
She pushed back against my thumb to push it deeper into her, while her pussy muscles pulsed around my cock. I exploded inside her as she climaxed with great rapid huffs. I removed my thumb, but left my cock in place as it shrunk inside her.
As she turned over and got off the table, she hugged me closely, then whispered softly in my ear "I'd like to do that again sometime. Ok?"
I kissed her passionately on her perfect mouth and replied "I suppose. If you want."