One of Drew and I’s favorite aspects of the lifestyle had been trying new things and pushing our boundaries. We like to talk through fantasies, hear what other people enjoy and pick things to try for ourselves.

Several years back, we decided to create a bucket list (we call it our Fuck-it List) of things we want to try. The list ranges from pretty wild (like participating in a gangbang at a swinger club) to pretty mild (flashing my tits at a store). Sometimes we plan what we want to try, and other times we will challenge each other spontaneously.

Drew and I were on a business trip in Florida, and decided to stay over for a couple days at the beach. We stayed at a Hilton right on the beach. After a few hours of beachtime, we had dinner at the hotel before heading up to our room to get ready to go out. I was in the mood to play with a single guy, and we had found a club across the street. Drew and I agreed to try to check off “pick up a guy at a club” from our list. We were alone on the elevator ride up to our room, and I flashed Drew right before the doors opened.

Drew: I bet you wouldn’t be brave enough to do it when the doors open.

Me: Sure I would!

It was a moot point because we arrived on our floor and headed to our room. We showered and I slipped on a dress. We headed out and got into the elevator. Drew laid down the challenge again.

Drew: I bet you won’t flash the first guy to get into the elevator. Just make sure it’s not a kid or anything. (He laughed)

We were on the 9th floor and the elevator stopped on the 5th floor. A handsome black man stepped into the elevator.

Me: So my husband and I have a bet.

The guy: Oh yeah, what’s the bet?

Me: He bet me that I wouldn’t flash the first guy that got into the elevator.

The guy: Well that sounds like a great bet and I hope you win!

I pulled down my dress and showed him my tits.

The guy: Well those are very nice! I love those pointy nipples! Do you mind if I get them a little kiss?

Me: Go for it!

He gave my boobs a little caress and kiss just in time for the elevator to reach the lobby. We exited the elevator.

Me: Can we buy you a drink for helping me win our bet?

The guy: I would love to join you for a drink.

We went to the hotel bar and had a drink. Our new friend’s name was Isaac and he was in town for work. He asked about the bets and I explained the bucket list. He explained that he was on a few lifestyle websites himself. This wasn’t his first rodeo with a hotwife.

Isaac: Well if there are any other items I can help you check off, I would love to help!

I gave Drew a look and he nodded with approval.

Me: Hmmm. Well, I was in the mood to play with a single guy tonight. Would you want to be that guy?

Isaac: Sign me up!

We paid the tab and headed back to the elevator. It was a lot busier on the way up, so we had to behave. Isaac did give my butt a little squeeze a few times. We got to the room and Isaac asked if he could play with my boobs again. I said of course and he reached around behind me and put his hands down my dress. I leaned back and kissed him.

He lifted the dress over my head and we continued to make out for a bit. I told him I had to pee, so I gave him a quick kiss before I left the room. When I came out, he was laying on the bed, stroking his beautiful thick 9 inch cock. I immediately crawled in the bed and bobbed my head up and down on his rod, stroking, licking and sucking every inch.

After a bit he asked me to sit on his face so I lowered my pussy onto his mouth. He sucked on my clit and teased it with his tongue. I was getting close to my first O, but I couldn’t quite get there in that position, soI turned around and moved into a 69. That did the trick, and shortly afterwards I had my first small orgasm. I rolled over onto my back and he moved over to my side. I sucked his cock while he fingered my slit.

He grabbed a condom and rolled it half way down his shaft. He spread my legs and impaled me with his massive sword. I was dripping wet from all the anticipation, so it only took a few thrusts to take him all in. The stretch felt so good! He hammered away for a bit when I decided which challenges I wanted to complete.

Me: Do you want to bend me over and spank me?

Isaac: You like it rough?

Me: Nothing crazy, but a little bit is nice.

He continued to rail me and put his hand around my neck, applying the perfect amount of gentle but firm pressure. I smiled in ecstasy. He flipped me over on my side and fucked me on my side for a bit. He swatted my butt a few times. It felt so good. I found a good spot and grinded hard in his dick. He flipped me all the way over to my hands and knees and really unleashed.

He continued to spank me until my booty was red. Each spank stung a little, but in a good way. As I got a little nosier, he thrust a little faster. He finally pushed me over the edge and my body shook with an orgasm. I was breathing so hard that I was barely able to get out a question.

Me: Hey Drew, so you want to get ready to help us with another challenge?

Drew; Sure!

Isaac: What’s next?

Me: Two guys cover my ass with cum. You’re up first!

He quickened his pace until he pulled out and sprayed my ass with cum. Drew was ready to take over and he took the spot behind me and went pumped hard for a bit. It didn’t take long until he pulled out and hosed down my butt with a second coat of jizz.

Drew took some pictures before I got cleaned up and thanked Isaac for helping us to complete three challenges. Not bad for one night of work!