The waitress at the hotel restaurant [humiliation]

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TL;DR My wife, me, and her occasional lover unintentionally gave an unassuming waitress whiplash watching our dynamics evolve over the course of the evening.

Text here. Visuals inside.
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Note: Obviously this is a true story. No sex – well the sex came later. It's a longer story, but I wanted to try to paint the picture. Enjoy if this is your thing. Apologies if it's not.

Last Tuesday evening, my beautiful wife and I drove down to the city to meet up with a gentleman with whom we had a previous encounter. It was the first time I was meeting this guy, though she had slept with him twice solo. He was her first, and her second time with another man besides me in as long as we have been dating (over a decade).

We weren’t sure if anything was going to happen physically on this Tuesday evening. We had agreed to a “innocent drink” in his hotel lobby bar, as he was in town for the night for work.

Side-note / foreshadowing: My wife, at this point in the evening, already knew she was going to suck his cock. Sucking his larger cock is her favorite thing in the world and has basically given him free use of her mouth. Its what she wanted, and I guess she had intentions.

For those still in the cuckold fantasy space (no judgement – was there for over a decade myself), this is one of those “real life is hotter than fiction” moments. But it is genuinely real life – what happens when you’re making other plans.

We got the babysitter situated and hopped in the car to head to our dinner reservations in the city. We hadn’t anticipated construction bringing the already constrained highway down to one lane and missed our dinner reservations by about 20 minutes. We needed to eat, but we had agreed to meet this guy for the innocent drink, so we parked by his hotel and after some searching, decided to eat in the hotel restaurant. We figured it would be perfect – we would go, get a quiet secluded table, eat something light, have a drink or two, and then tell him we were downstairs.

Now, we aren’t difficult people. Really, I don’t think we are. We sat in a booth, and the lamp that hung over the booth was angled in such a way that when we sat across from one another, the raw lightbulb was in both of our eye-line. It wasn’t great – bit blinding. We mentioned it to the waitress, and asked if it were dimmable (it wasn’t), and if we might be able to move. The waitress was gracious, but did let us know all the other tables had already been set for breakfast the next morning. She offered to un-set one and re-set it after we left, but it felt like an appropriately empty offer. Not wanting to cause any trouble for her or the morning staff, we let her know it was not a big deal and we would stay in the original booth. I only mention this part to reinforce, this wasn’t a “here’s your water…” exchange we had with the waitress. We had a real back and forth, as a couple, with her.

We ended up sitting on the same side of the table because a. we are pretty into each other, and b. the lamp… We had drinks, ordered some food, had some other friendly exchanges with the waitress.

When we had finished our meal, and the waitress had cleared the table, we texted the guy that we were downstairs. Now, it’s always been a fantasy of mine to sit across from my wife and another man in a booth. Just the idea of wandering hands, while maintaining eye contact with me, while getting flushed and distracted… I dunno, sounded hot. So, before he came down to the lobby, my wife retook her seat on the other side of the booth.

He arrived a few minutes later, and the waitress came back to take our drink order. At this point, she must have been scratching her head wondering why this couple who had been flirty and clearly on a date, was now sitting opposite one another with another man next to the wife. We all ordered drinks, and we continued some flirty banter. We confirmed I was correct in thinking it would be hot to sit across from my wife and another. It was. The waitress came to check on us a few times. I don’t know if she could see their hands in one another’s laps, or whether she could just tell that our conversations became more hushed once one of us noticed her approaching. Either way, she quickly gained awareness something juicy was happening at our table.

After about 45 minutes, wandering hands, not-so-subtle kissing, and some solid trialogue between a husband and his wife meeting her occasional lover for the first time (for another story – this one is about the waitress ????) I asked if he would be ok with us coming up to his room for another drink. He was into it, so we got the check. I paid for dinner and our drinks, with the waitress eyeing me with a quizzical look. And then, I suggested that the two of them head on upstairs, and that I would venture to the car parked a few blocks away to get our bag – with some toys and outfits and restraints (just in case lol).

In the heat of the moment, and the excitement of leaving my wife at a table with another man who was about to take her up an elevator to his room… even typing that now is getting me hot… I got up and started my walk to the car. I signed the bill, and left the restaurant.

Now, Imagine seeing this evening scene play out through the waitress’s eyes. This couple comes in, clearly in love. They have a flirty sexy dinner date on the same side of the booth. Then a third guy arrives and sits on the same side of the booth alone with the original woman. Now a different flirty dynamic emerges. Hmm. Then the original guy pays the bill and exists the restaurant, and the hotel, leaving now only the original woman, and the new man, on the same, albeit other side of the booth from where she and the original man sat. The woman and new man then get up, and head towards the elevators together.

Cracked us up. We weren’t at all trying to be in her face about it – but she either a. knew exactly what was happening and thought it was weird and funny, or b. she is still baffled by the strangest encounter with three patrons she has ever experienced. Either way, it really is the little things, isn’t it? Cheers!

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