I had a gentlemen that licked my armpits. Lol.  

Lick Lick,

Ashley

I once saw a provider that another provider wanted me to see.  She was riding me CG, and fell asleep.  Then I realized she was out of it on drugs.

LLAP,
Swim

Once saw this lady while on a biz trip that just loved to meow and purr when she was happy.  I had seen from reviews to expect it but it was still really weird to me.  But, as in everything, she was alot of fun.

this one girl .. every time she came she burst out laughing and literally applauded as a reflex reaction.     of course no complains there to have a girl applaud 5 or 6 times during our time  

Sensory deprivation ( blindfold, headphones, tied down) followed by sensory stimulation like never before.  
Only with my BFF whom I trust absolutely, after years of experience together and getting to know each other quite well.

thats normal every day stuff .. she said weird   LOL        been there, done that .it is a very intense experience.

My client had a baby fetish so we dressed up in adult diapers and onesies, drank champagne out of baby bottles and changed each other's diapers

that would help me undress and then insist on sniffing various parts of my body before I took a shower.  It was really loud and deep so you could hear her inhaling through her nose, which was making skin to skin contact.  I had no idea what she was trying to find out.  My only guess was she might be seeing if I had the scent of another woman on me, but by then, I had already stopped seeing two providers in the same day.  The second and third times I saw her, it became more intense, so I stopped seeing her because I thought it was creepy.  Too bad, because after the shower, the service was always great.  I could have been a regular for a long time had she not put me off with her sniffing ritual.  

In 1992, I was with a TS escort.  I was on top of her cuddling her and dry-humping her.  When I told her I was about to cum, for reasons I don't know she started squeezing my head on both sides.  I told her to stop, she did and then I came.

Not really something that someone has done to me, but definitely the strangest thing I experienced during sex: I was coming home from a friend's house. I was in my late 20s and I went into a convenience store to get a soda and there was a woman standing in line in front of me buying a lottery ticket. She looked to be in her mid-to-late 60s. I was stoned and horny, looking for something different, so I chatted her up. She wasn't a hot GILF type though... just very plain and average for a woman of her age. Her English was ok and she was from Mexico. It was one of those occasions when you both feel that a sexual adventure is about to happen. I offered to drive her home and she eagerly accepted.  

We got to her house and started getting frisky, but she told me her daughter would be home from work soon so we had to cool it. Then she had the idea that we could go out to the garage. She doubted her daughter would come out there and besides she said, we could lock the door as the garage had been converted into an apartment.  

We get to the garage/apartment and started making out, then went over to the bed, ripping off our clothes. It was strange already because I had never been with anyone her age. The age difference made it feel extra kinky and I went down on her right away. She was very clean and at one point she made the comment that her vagina was "poca usada," meaning it hadn't seen much action. As an aside, her husband had moved back to Mexico many years before and she lived alone with her daughter who was a cop.

The the creepy/odd thing happened... while we were fucking in the missionary position, she told me that she was staring at the rafter above the bed (she was on her back looking up toward the ceiling) where her nephew had hanged himself the year before. So here I was fucking a 67 year old (as she told me later - we did this a few times) woman in her garage on the bed right beneath the spot where her nephew had been found hanging.  

Some people might not find this strange, but it actually creeped me out. We got together 3 or 4 times and I always took her to a motel after that. Not only did I not want to run into her daughter, but I didn't like the idea of fucking in that garage again.

A woman I knew years ago in DC used to put on these wonderful girl-girl shows with another girl. The deal was I could watch only.  Which was exactly what I bargained for so sure. Once her friend couldn't make it but she agreed to come over and give me a toy show.  We both started to get a bit . . . anxious, so she produces a strap on and asks me to put on the strap over my underwear and fuck her with it.  So of course I said no. Hah!  I fucked her with that prosthetic dick until my own dick was bent in half.  Hmmm.  I guess she really didn't do that "to me".

I had another gal who was quite fun and who was one of the few girls at the time I knew who did greek. One night as I was lying on my back and she was blowing me, she started raising my legs in the air and aiming her tongue at my ass. I protested. Strongly. Yeah--I know some guys are cool with rimming but I'm not and besides it felt like I was about to get bent in half.  She told me later she really "loved the smell".  I didn't see her after that.