Sometimes things turn out way better than expected. Maybe it’s extra time, maybe a little surprise service that wasn’t listed, or just that spark of chemistry you can’t plan for. I’ve had a few occasions where what started as a standard booking ended up being unforgettable because of those little surprises. Curious what’s the best unexpected thing that’s happened to you during a session?

the gal turned to me and said:   "You're not going to make me sleep alone tonight, are you?"

I met a kind man who enjoyed the pleasure of my company, so much he tipped me $1k. I was extremely appreciative, but I realized I have a unique set of skills. Most people don’t tip at all, so $1k was a huge surprise.  
I see a pattern of the friends I cater to the really cool ones smoke 420 &/or do edibles with me. We vibe.

We both had to drive a fair distance, as she would graciously meet me halfway for our outcall. I would typically reserve a spacious suite that included a kitchen, though we never made use of it, as we often opted to dine out at local restaurants.
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On one particular occasion, she inquired a few days before our meeting where we would be dining. I thought little of it at the time, assuming it was simply part of the usual planning. As it turned out, the question was merely a ruse.
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I can’t recall where I had actually made reservations, because when she arrived, to my complete surprise, she was carrying two large shopping bags of goodies. Instead of us heading out, she prepared an elaborate dinner right there in the suite.
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She made several incredible dishes all from scratch, bringing along not only fresh ingredients but also a few of her own kitchen tools, knowing (or guessing) that the small kitchenette would be minimally equipped.
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Though she is long retired now and married, she casually mentioned that she had previously cooked professionally, a detail that became clear after that unforgettable meal. Perhaps this was her way of thanking me for all the times we went out to fine restaurants together? Idk.
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What I do know is that whoever ended up marrying her found not only a sweet, GND hottie, but also an exceptionally talented cook! lol.

On one occasion with a hot milf, I was behind her doggy style when she started yelling, "Marry me, Baby! Marry me!!" I almost uncoupled from her I was laughing so hard.
Another time, in Jaco, Costa Rica, I was with one of my favorite girls and we'd just finished. I mentioned to her what my age was and she said: "I don' know about dat, Papi, but you got an 18-year-old dick!"
I know....I know...she was probably just being kind but it was spontaneous and funny as hell.

Went and got some tacos from a nice little Mexican joint down the street after an appointment. Amounted to about 45 extra minutes with a lovely lady.

I took the risk of putting together 2 ladies who hadn't met before. I wasn't exactly nervous--these are two lovely ladies with great attitudes--but one never knows how a new pairing will work out.
Brother, they worked out. And they worked me out. The cherry on top was, after vigorous DATY and DFK between them, and while one lady was diddling the other with a strapon, she starts playing with her new girlfriend's asshole. I think I splooged right then and there.
It's the small moments that stay with you.

Vegas people will get this.
Sometimes it isn't pizza. I knew someone for loved the wings at their 24hr cafe. They are pretty good.
But its usually when they just want to hang out with me afterward, NSA.
BCD is BCD..Its always fun but it what happens after.

-- Modified on 9/8/2025 4:36:25 PM

DATY, she cried out, "I'll pay money to the woman who taught you that!"

I was going to have a 24 hr date where we were suppose to start in the late morning. She ended up texting me at 1:30a to let me know she was at my door. We ended up getting the party started a little early.

Pretty good story.

I booked a birthday weekend thing with a girl I had been seeing for maybe two months. We drank champagne, swam around the pool, talked about life…next thing you know we’re back in the room and this girl just put me in sans anything…pretty good surprise and had an unforgettable time. Wasn't really sweating the post Planned Parenthood visit but was quite a surprise nonetheless.

The first one is an example of the obscenely beautiful generosity that some men possess. It was a first date. He flew me to NYC and put me in a five star hotel for two nights, even though we were only meeting for dinner on one evening. He'd been a bit cagey (but also forthcoming when asked direct questions) during screening so I knew enough about him that he was "safe" but not much more. Upon meeting, he was the epitome of elegance and graciousness (and I don't F'n use those words lightly).  The 'surprises' were two-fold... the GOTDAMN best steak of MY LIFE... TO DATE delivered via room service😱🤤... and a 'parting gift' of a 5k Hermés bracelet.... and we did nothing more than kiss, converse and snuggle.
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The second is an example of his choosing an amazing destination and level of service. It was a week vacation at an international destination (we did this quarterly for years) but this particular place had a certain type of butler service. At one point we'd been gently (but repeatedly) chastised for "public indecency" and had resolved to simply staying naked, stoned and drunk on the rooftop of the villa, alternating between the plunge pool and shaded loungers (no one wants trouble with the neighbors, after all🤷🏻‍♀️). At some point our butler checked in on us and we made a joke about pink elephants, meaning the custom of re-gifting shitty gifts or contributing some BS joke of a gift to whatever group you don't really GAF about. Welp, within 24hrs the butler had found a genuine WHITE elephant and taken great pains to tint it PINK (checked it out later, zero harm done to the critter) and parade it around the villa/resort. We had NO intention of it being any sort of official request to freakin' produce a GD PINK elephant.... but that's how seriously this place took our drunk/stoned/horny/dumb comments.
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The third example is about how beautiful it is for a man (for anyone really, but men are especially programmed to repress this shit) to be comfortable/confident in *respectfully* communicating WTF'ever he's wanting. I was working at a brothel and a guy came in hemming-and-hawing about the dynamic he wanted. A bit of conversation later and he chose me and a gorgeous black lady that was as opposite as possible to me for a 24hr date. He had a curiosity around BDSM dynamics and chose as visually/dynamically opposed ladies as possible .... and we had a FREAKING amazing time! My personal highlight was him requesting to be (kinda viciously) spanked and then penetrated by my hairbrush, then led around the public bar area of the brothel on his hands and knees (naked, with the hairbrush sticking out of his ass, with my bathrobe belt serving as a choke collar) and for him to perform "good doggie" tricks like rolling over, playing dead, fetch, etc. He had the situation he was craving because he could articulate his desires in a polite way, and I (and the other lady) had a freaking great time with him, and with ourselves (his 'torture' to be sooooo close to the gooshy squishy yummy parts and be denied the taste/touch).
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Christ.... I do need to write a book at some point...😆

When you tell something to them in passing, and then they make it a reality.

LMFAO