Shy wants to know - Funniest, most Embarrassing or just plain Nastiest encounter with a provider? Go!

#2
I have a few that I’m sure will seem tame compared to what many of the other more seasoned guys here have experienced, but I haven’t been doing this long.

Not sexual, but I had a long trek to meet a lady and wanted to shower when I got there. She had just checked in and couldn’t warn me, but the shower head was angled towards the curtain and had tremendous water pressure. When I turned it on, it blew the curtain open and drenched the floor. It was both funny and embarrassing.

A few weeks ago, I visited an old friend in Mexico. After getting together, we were just laying there and laughing. I was laughing so hard that I ripped a loud fart.

I had a GOOD nasty experience. I met a girl for the first time last night. Her reviews were stellar, but I wasn’t expecting what was to come. She fucked my face for 15 minutes and it was hot. I’ve never experienced it that intense and for that long.

I’m sure that this will seem G-rated once the other posts come in, but I’m still somewhat new at this.
 
#4
Embarrassing- 20 some odd yrs ago, had an asian woman at the house . Explained to person on the phone , do not park in the area. So all is going swimmingly , a beautiful girl . About an hour a knock on the door ! SCPD . Apparently neighbor called about an odd car . The officer was very cool about it . We talked a bit , had some common ground . The said neighbor was a frequent flyer at a local strip club !
 
#5
Embarrassing- bachelor party-the Provider for the Groom wanted nothing to do with him, but he went in anyway-and past out before anything happened-she came out Looked at me-"I want you" pointing to me-Went in the next room-and found out they all watched from the window..
Nasty- met up with Sugardaddy date at the Hollywood-thought I was in her Vagina during MISSIONARY-until I pulled out and wanted her to finish me oral-went in so easy an she didn't make a face ,say a word, etc-I wasn't in the Vagina as some of the smell and poop was on my dick..
 
#7
Embarrassing/funniest

had to be the time I had this provider chocking with my cum. She was giving an amazing BJ I came in her mouth so hard, it was like a projectile straight down her throat, we both laughed It off afterwards.

Funniest

The very first time my ATF Asian provider surprised me with a finger in my ass … I had one those reactions to when you’re falling asleep and feel as if you’re about to fall off the bed, I was just there two hands covering my ass, processing what just happened.

Nastiest

The one time my Ex had just finished blowing me off, thought she had swallowed it. lays on top of me face to face and tells me to open my mouth . she wanted cum swap my load, I didn’t but I sure was surprise with her desire of going through with it.

I don’t mind kissing DFK/LFK after oral sex, but I sure don’t know how to feel about cum swapping… Anyone had a similar experience with a SO
 
#9
Embarrassing in the early 90s had a case of whiskey dick. Provider was trying her best to get the position out but it wasn't meant to be be. Was was meant to be was me passing out mid act in missionary position
Funniest see above perhaps adding she was a petite Asian who could move budge me /had to wake me up to get me off her
Nastiest-- lucky as nothing to nasty comes to mind. Had mud on the helmet a few times , unknowingly earning new set of red wings with provider, had a provider yell at me for not grabbing and squeezing her vagina hard enough during a session.
 

billyS

Reign of Terror
#10
Most embarrassing, early days of UG I answer an ad for a massage MILF in South Hempstead. I was in my early 40's she seemed about the same. White woman. We do the massage then she goes to finish me with her hand as per the ad but I coax her to give me some head. She did so reluctantly and kept stopping to say "you better bring more money next time", yet she wasn't stopping. I was getting the vibe she was horny and liked my cock.
So I lay her down and start rubbing my dick on her totally untamed bush.
All she says is, if you can get it in you can fuck me. She was dry and tight but after working the head in she relaxed and got wet and I got about four or five inches in, enough to start sliding faster to get me off

Right before I cum she looks me right in the eye and says are you "*****" using my first and last real name. I shot my WOD in her but my shock over shadowed the orgasm. All of the sudden it hit me who she was, she was two grades behind me and had dated an acquaintance. The years were not kind to her which is why I didn't recognize her at first.

But I was so embarrassed that someone from my hometown who shares a lot of mutual friends knew I was a whore monger.

The whole situation just weirded me out so bad I didn't want to review it here.

I found out she died a few years later, she had some weird degenerative disease.
 
#11
Nastiest wasn't necessarily nasty but I was dining on her pussy when she started quivering like crazy and squirted all over my face. Apologizing over n over cuz it was a first for her. Then returning half the donation.
Funniest was hotel neighbors pounding on the wall and hotel personal asking politely if we could tone it down a bit.
Not a provider but most embarrassing was with girlfriend at her mom's house and mom bursts in the door just as I'm ready to explode. I rolled over and as I was falling off the bed I cum midair within inches of her.
The hottest and weirdest was I had a provider ask if I would bring her and pay a twenty dollar entrance fee at a swingers club and fuck in front of strangers then she wouldn't charge me. My first time at a swingers club and first time fucking in public was the beginning of a new and exciting fetish of mine.
 
#12
Dining on a provider at a 5 star hotel - She is very loud and I come up for air only to see housekeeping standing in the vestibule with some chocolates on hand for turndown service-I had accidentally left the door open .. Sue ran out before I could ask her to join !

Dropping a huge week or two built up load in a gals throat only to have her gag and reflux back through her nose-The sight of cum and snot dripping out of her nose was disgusting.

Only recently getting a legit massage and having the AMP fart continuously for a few minutes- At first she giggled and apologized- After she expelled enough air to move a sailboat I yelled at her and told her to get out
 
#13
Not sure what category this falls under, but here it goes....

My friends and I decided to go to a brothel in Prague. We found a few girls to take upstairs separately, it all went well. They also provided outcalls, so I took advantage of that a couple days later. She came through to our Airbnb and I had the place to myself. We drank a little wine, started making out, lots of foreplay, dfk, as I put the claw on her to make her squirt and got her to that point. I guess she lost control of all bodily functions. While she was squirting in the squatting position she also shit all over the floor. She didn't realize it right away, but when she did she was pretty embarrassed.

I felt bad, told her not to worry about it and went to shower. Afterwards she cleaned up the floor, then finished me off with a bbj.
That's an encounter for the books.
 
#14
this is by far better than tv!! whiskey dick, the cum coming out the nose had me cracking up.. and the cumming midair!! I could picture that….
Billy I thought for sure you were gonna say in that untamed bush was a hidden penis !
 
#15
Most embarrassing, early days of UG I answer an ad for a massage MILF in South Hempstead. I was in my early 40's she seemed about the same. White woman. We do the massage then she goes to finish me with her hand as per the ad but I coax her to give me some head. She did so reluctantly and kept stopping to say "you better bring more money next time", yet she wasn't stopping. I was getting the vibe she was horny and liked my cock.
So I lay her down and start rubbing my dick on her totally untamed bush.
All she says is, if you can get it in you can fuck me. She was dry and tight but after working the head in she relaxed and got wet and I got about four or five inches in, enough to start sliding faster to get me off

Right before I cum she looks me right in the eye and says are you "*****" using my first and last real name. I shot my WOD in her but my shock over shadowed the orgasm. All of the sudden it hit me who she was, she was two grades behind me and had dated an acquaintance. The years were not kind to her which is why I didn't recognize her at first.

But I was so embarrassed that someone from my hometown who shares a lot of mutual friends knew I was a whore monger.

The whole situation just weirded me out so bad I didn't want to review it here.

I found out she died a few years later, she had some weird degenerative disease.
I remember you telling me this story
 
#16
Nastiest wasn't necessarily nasty but I was dining on her pussy when she started quivering like crazy and squirted all over my face. Apologizing over n over cuz it was a first for her. Then returning half the donation.
Funniest was hotel neighbors pounding on the wall and hotel personal asking politely if we could tone it down a bit.
Not a provider but most embarrassing was with girlfriend at her mom's house and mom bursts in the door just as I'm ready to explode. I rolled over and as I was falling off the bed I cum midair within inches of her.
The hottest and weirdest was I had a provider ask if I would bring her and pay a twenty dollar entrance fee at a swingers club and fuck in front of strangers then she wouldn't charge me. My first time at a swingers club and first time fucking in public was the beginning of a new and exciting fetish of mine.
YES-My first Squirter was also a surprise-I thought she peed in my mouth...
 
#17
Funniest. I set up a meet with a provider I found on a popular site. She gave me the motel address and off I went. When I got there I parked in a spot facing the rooms. I texted her that I was there. A moment later one of the motel room doors opened and a hot women in lingerie peaked out. Not the woman in the pictures, but they rarely are. I was pleasantly surprised.
Got out of my car, walked over and went inside. We had a nice time and even gave a received an gs.
I got back to my car and looked at my phone. I had a text from the provider with her room number and it was a different room. More texts asking where I was. My phone was on silent and in my pants pocket. I had been in the wrong room with the wrong provider.
I texted and apologized. I went to her room. I tried to explain what happened. Her English was not great and I have no spanish She was sweet about it. I felt bad, that she had lost the appointment so i paid her and we got naked. I gave her oral for about 30 min. Although I had just cum, she then gave me a good bj with a hj finish.
Nastiet. In Mexico on vacation about 20 yrs ago. Met a real stunner in a strip club. Looked like one of the gorgeous women from Mexican TV. Anyway she was a provider so agreed to came back to my hotel room. While giving her oral, I put my finger in her butt. She told me to put in more until my whole hand was in there up to my wrist. The she had me put my whole hand in to her pussy and fist her until she came.
 
#18
You know what I was thinking could be fun?.. story time! What is either your
A) most EMBARRASSING sexual encounter or
B) FUNNIEST sexual encounter or
C) most NASTIEST most freaky sexual encounter you’ve ever had with a provider
lol .. I know there’s gotta be some good ones out there:):):)
Dear Shy. Just wanted to say that I have really enjoyed this thread and your other thread about techniques. It's fun to read the replies and also your comments. Its a nice change on this forum. Thank you so much for starting these threads and being so interactive with us. You truly are amazing.
Best wishes.
 
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