After a few years of making hotwife connections with couples of all experience levels, I’ve found the best meet ups happen organically when I’m not looking that hard. Reddit seems like a better place to share stories and pursue one of my other favorite hobbies, helping new couples wrap their heads around those first steps after they’ve had ‘the talk.’ I thought I’d share this story, however, because it was one of the first times I ended up being a part of a challenge/role play the couple we’re trying out. Sometimes things progress so quickly and naturally that it’s important to take a step back and think what you both want out of this as a couple.

I was traveling for business from my home base in New England area to Chicago. I usually stay at nicer hotels and always check out the bar to enjoy a cocktail or two after meetings. Sometimes over the course of the evening I’ll connect with a woman traveling who is open to conversation, and sometimes it leads to more than that. Only once have I met a hotwife with an ‘anklet.’ On my last trip prior to NYC, a woman I spoke to at the bar ended up being an escort who I let down politely so I was hopeful to avoid a similar situation in Chicago.

As luck would have it a beautiful brunette woman was sitting by herself at the hotel bar and seemed like she was dressed for a date. I wasn’t quite sure what to make of this so I figured I’d ask her about it. Innocent enough. She laughed and said she was here for a date but didn’t know where her man was so I said I’d be happy to buy her a drink and it would be a shame if she had to sit alone watching sports news. She seemed surprisingly receptive to that. We chatted for a while about my work, her ties to the area, and who had the nerve to stand her up when she seemed to get a bit nervous before saying the man she was waiting for was actually her husband!

I said wow he really does have some nerve then … and “what would he say if you saw you sitting her talking to me? Knowing that I’ve bought you a drink?”

She said that “actually you might be surprised to hear he wouldn’t mind”

I said “actually I might not be that surprised at all but figure you still will let him sweep you away when he arrives.”

She laughed and said she’d tell him to wait his turn. And I said wait his turn for what? She said for “whatever we decide he needs to wait for. In fact, he’s already here waiting in the booth in the back.”

I said “well my rooms upstairs let’s make him wait longer.”

Then she said they actually didn’t know what would happen tonight but If it went anywhere he wanted to be in the room. I think she thought this would be a deal breaker for me because when I said “no problem” she seemed like she was unsure but ultimately waved him over.

We chatted for a bit about how this was “some date they were on.” And after a couple of shots we went upstairs. I could tell they were both excited but nervous so I offered them an edible and we all enjoyed one.

In my room, she and I stood kissing in the entry way and I stripped her down to the sexiest black lingerie. I asked what their limits were and they said they had only ever gone as far as her making out and getting fingered by a guy with a guy at a club while the husband watched. They had talked about it after and were willing to go further.

I said that before the edibles set in they needed to have an honest talk about what they wanted to be discussing in the morning and that I was going to step out while they did it. I went out on the balcony for a few minutes while they talked. I could see them sitting on the bed holding hands and finally she gave him a kiss on the cheek and came to get me.

She said she felt my cock when we were making out and could tell it was bigger than her husband’s. She told him she wanted it inside her and had permission with a condom. She pulled me back in the room by my belt buckle and dropped on her knees.

After one of the most enthusiastic blowjobs I’ve experienced, I devoured he soft pussy and then slid into her. She was completely wet with anticipation. We both looked at her husband when I was about halfway in and he just let out a sigh and a laugh with big eyes completely on her. All he said was “wow, yeah, enjoy that.”

We fucked for a while in all positions. I could tell the edible really hit for her when she was riding me because she found this rhythm on my cock and had her hands on her tits with her head back moaning with pleasure for what seemed like forever.

After she came multiple times I let myself go when she asked me too saying “cum deep inside me.”

This is where it’s key they set their ground rules. Not only did we know the condom was staying on, she knew she could enjoy the entire experience with permission from a loving husband.

They left and I made sure they got an uber and could pick up their car the next day.

I’m confident I’ll see them again, but even if I don’t, I’m happy they explored the boundaries of their relationship and can do so with this positive experience as a starting place moving forward.

Good luck out there!