I had some hotel and airline points to burn, and a family member offered to take our kids for a weekend, so it was off to Vegas.

We landed early Friday morning, and we were hitting the strip by noon. After a few hours of gambling, but my wife and I were doing pretty good, up a few hundred each. I joked about we should make a competitive bet about who will win the most for the day. She asked what I wanted, and I said she had to go to dinner the following night in her sluttiest dress and a butt plug in. She pointed out that she didn't have a plug, and I told her "It's Vegas - we'll find one."

"Deal. But if I win, you're wearing the plug to dinner."

I took that bet.

It was getting late and she was up close to $1,000 on me. She was making jokes about how I should sit down now, because I won't be able to later, etc.

We were playing roulette, and she was getting whacked, and made a big bet on red to recoup. I decided to put my whole stack on black... and it hit! I not only doubled my money, but she set herself back heavily. This was the turning point, and my win was guaranteed.

The next day we jumped around day drinking, and made sure to hit one of the sex stores. We found a plug she felt she could handle, and a bottle of lube.

Later on we got to the room to get ready for our fancy dinner, I couldn't wait and pushed her on the bed, pulled off her panties from under her skirt, and started to eat her out. I was 100% focused on getting her off. She doesn't squirt, but she'll "leak" grool pretty heavily when she cums. My fingers were in her, my tongue was pressing on her clit, and I loved the moment her legs squeezed my head as she reached climax.

I gave her a minute to catch her breath, and then told her get naked and roll over.

"Yes, daddy."

She was with her ass in the air, and I could see her juices and dripped into her asshole just as I hoped. I dove in, tasting everything, and started to press my tongue into her asshole. She moaned as I rimmed and tongue fucked her ass, all while rubbing her clit with my thumb.

As if we were reading each other's mind, she said, "Get the lube and start with a finger."

I got her ass ready to go and started to slide a finger into her. There was a little resistence, but it popped in and she said "Oh fuck." I went slow until I felt I could go deeper and faster. I had her roll on her back, and then resumed fingering her ass while I ate her out again. If she was wet after the first session, she was a goddamn ocean now. I had a finger in her ass, two in her pussy, and she came to hard that she shot backwards off my fingers, with an audible "pop" and queef. She twitched for a bit and I took the time to get the plug.

This time I had her bend over the edge of the bed. I added more lube to her asshole, put my finger back in for a bit, and then lubed up the plug. I was on my knees, eye level with her ass, and it was so fucking hot to see a mixture of lube and cum dripping down her ass and thighs.

I started pressing the tip of plug into her and it went about a quarter of the way in, so I pulled back and listen to her moan more and tell me deeper. I did this a few times, getting to the thickest part of the plug before pulling back. Seeing her tight little asshole stay spread out for a second before closing back up was the sexiest thing to witness. The next push, her starfish spread out and the plug slid in.

Without missing a beat, I stood up, dropped my pants, and my cock slid into her pussy without any effort. She was so fucking wet and warm that I knew I wouldn't last long. In fact, she came almost instantly and I saw the plug start push out and get sucked back. Seeing that, feeling her cum, and feeling the extra pressure from the plug, I came so hard. It was literally 3 pumps for me.

After that, we showered and got ready. Having the plug in her all dinner was awesome to experience, as she kept saying that all she felt was how wet she was.

By terms of the bet, she pulled it out after dinner. But when we got back to the hotel room, she rode the fuck out of me and begged for an ass in her finger when she was close to cumming.