Weirdest Session?

[Ben19]

I have a strange one.

Back on the west coast and my last time using leolist.

Went into an Incall downtown , nice location. The girl was very very pretty but I could tell something was up. She appeared very sad and I could tell she had recently cried. I immediately became put back. I always like to get to know the person before and started talking. Her answers were very short. She was clearly disinterested. She told me why are you doing this hobby you shouldn’t be etc. She said she has to go to washroom and was there for a solid 10-15 min. I actually knocked couple times. At this point I wanted to walk out, she was not high but I could tell she was very sad about something and I was uncomfortable. I made up a story about how I have an emergency at work and gotta leave. She said wait before you leave I have to come with you.... she got dressed. Left part of the money I gave her on the counter along with a long hand written note (took her a while to write ) and some weed. Asked me to close the door lightly and go to the right to take the elevators. As soon as I close the door this girl RAN the other way towards the stairs. At this point I was scared and was aggressively hitting the elevator button. Anyways after this I stoped hobbying for a few months and sticked to civy girls.

 

[blixa]

This was in the late 90s... I found an ebony milf in the backpages of Now magazine with no photo but thought it was worth taking a chance. She turned out to be OK looking, however she refused to remove her bra because she apparently had a scar on her tits and felt uncomfortable being naked. Obviously I wasn't happy about it but at that point I just needed to bang something so I went ahead anyway.

 

[massman]

Queenston spa, in Hamilton. Old ladies getting their grey hair cut in the front. Massage (often with significant mileage) in the back. Surreal environment. (Interestingly, I was never asked once, in multiple visits, if I was there for haircut or massage, just escorted into the back).

 

[kkelso]

Not sure if I've shared this one.

I went through a period where I was flying around North America quite a bit and was searching for the most premium experience. I found a high $$ (for the time) SP in San Francisco, $2,500 for three hours. She turned out to be almost as cute as her pics, a Paula Abdul type, and quite nice. To give her credit, she was the ONLY provider ever to get me off orally back to back - so some serious skills.

The weird element is that as part of her deal she required that a "protector" be present the entire time, a man she brought with her. She was up-front about it and it was agreed to ahead of time. He came in with her, an unassuming asian guy in his 30s, introduced himself, and then found a space in the hotel room where he was out of sight - in this case the little alcove leading to the bathroom.

I would have never known he was there, but I knew he was there. It never completely stopped being a little weird. I look back and ask myself "what was I thinking???" The things we do.

KK

 

[massman]

More recently. Have frequented this semi legit AMP a few times over the last couple yrs. At least twice, I am getting massage, and the back portion is over. Attendant leaves the room, before the flip. Door opens, I get a tap on the shoulder and asked to turn over. It’s a different girl that proceeds to give an amazing finish!

 

[autumn96]

I saw an SP (now retired but highly reviewed at the time; didn’t think I could go wrong) last December who obviously had severe mental health issues.

She was dishevelled and spent the first 40 minutes(!!!) of our hour-long session talking about her childhood problems, including parental drama. I was too nice to interrupt her, fearing she was literally about to kill herself.

Eventually she started giving me a blowjob and I was able to kinda half-mast my way to a finish but it was too weird a situation to enjoy.

Afterwards, she went right back to talking about her mental health issues and showed me her personal social media profiles for some reason or another. Despite my better judgement I stayed and listened to her for 20 minutes past my scheduled time before I pulled away and got the hell outta there.

It was REALLY bizarre and I was not happy, to say the least, about having spent $400/hr to be someone else’s therapist.

 

[Lovely_Lovelynn]

When I was 19, I had an appt with a gentleman who paid me quite a lot extra to duct tape a thick black garbage bag up to and around my bicep, and then punch him elbow-deep in the ass until I thought my arm would fall off.

Taking my arm out of his ass and removing the bag was the worst part of my experience.

 

[jimidean2011]

ok lovelynn wins this thread....

 

[richierich]

This was back in 2007. The agency sent the giril to the wrong room across the hall. There were an older couple in their seventies that opened the door. I was watching through the key hole
and immedietly called the agency. They then called the girl back and she just turned around and knocked on my door.
Next morning, I was going for breakfast and I got a thumbs up from the couple.

 

[anon1]

ok lovelynn wins this thread....

+ infinity.

 

[kherg007]

When I was 19, I had an appt with a gentleman who paid me quite a lot extra to duct tape a thick black garbage bag up to and around my bicep, and then punch him elbow-deep in the ass until I thought my arm would fall off.

Taking my arm out of his ass and removing the bag was the worst part of my experience.

Did you see your hand come out his mouth? OMFG.....
Had a mate back in oz who did some male escorting, and he had a client ask to be fisted...and then afterwards the client went to the washroom and came out and was itching to leave and then mate smelled something off and went into washroom and found bathtub layered in shit...made the client march back in and clean up the poo lol.

 

[Grimnul]

I haven’t had any weird sessions, personally, but I’ve heard a few pretty out there anecdotes from some of my regular ladies in Amsterdam.

One girl had a guy approach her window with a little dog on a leash. He offered her €300 to watch him fuck the dog. She declined.

Another regular of mine has a regular client who’s an old man, she thinks probably in his 80s. He can’t have sex, so he basically pays her for a 2 hour session, then just comes into her kamer and sleeps. She sometimes just leaves him there and runs errands. He does this twice a week, has been for a couple years now. She said she was worried that he’s going to die in her kamer one day.

Had another girl who had a new girl move into the kamer next to hers. This new girl had come up with a “revolutionary” new way to make extra money: charge clients for condoms. Now, we’re not talking like 50 cents or a dollar per condom used or something. This girl was charging the “standard” €50 per 15 minutes Amsterdam rate, but then also trying to charge another €50 for each condom her clients used, like one of those sushi places where you pay per dish you eat, I guess. She was not around for long.

 

[Ginomore]

Not sure if I've shared this one.

I went through a period where I was flying around North America quite a bit and was searching for the most premium experience. I found a high $$ (for the time) SP in San Francisco, $2,500 for three hours. She turned out to be almost as cute as her pics, a Paula Abdul type, and quite nice. To give her credit, she was the ONLY provider ever to get me off orally back to back - so some serious skills.

The weird element is that as part of her deal she required that a "protector" be present the entire time, a man she brought with her. She was up-front about it and it was agreed to ahead of time. He came in with her, an unassuming asian guy in his 30s, introduced himself, and then found a space in the hotel room where he was out of sight - in this case the little alcove leading to the bathroom.

I would have never known he was there, but I knew he was there. It never completely stopped being a little weird. I look back and ask myself "what was I thinking???" The things we do.

KK

You do realize that the Asian guy paid her to watch-right?

 

[Lovely_Lovelynn]

Did you see your hand come out his mouth? OMFG.....
Had a mate back in oz who did some male escorting, and he had a client ask to be fisted...and then afterwards the client went to the washroom and came out and was itching to leave and then mate smelled something off and went into washroom and found bathtub layered in shit...made the client march back in and clean up the poo lol.

It was a shitshow. I couldn't make eye contact after.

 

[kherg007]

It was a shitshow. I couldn't make eye contact after.

You ladies should get medals or wear the combat ribbon bar on your lingerie to show the clients you survived lol.."I got this ribbon for fisting a guy up to my elbow, this one for taking on 3 clients at once, this for an enormous sweaty fat guy, this for the 10 inch penis, this for the guy who cried at the end and kept calling me mommy, these two for ditching stalkers...." .

 

[jimidean2011]

lmfao. a shit show indeed...

 

[mellowjello]

When I was 19, I had an appt with a gentleman who paid me quite a lot extra to duct tape a thick black garbage bag up to and around my bicep, and then punch him elbow-deep in the ass until I thought my arm would fall off.

Taking my arm out of his ass and removing the bag was the worst part of my experience.

You're a pro in every sense of the word.
I still have issues wiping my own ass.

 

[massman]

Two other slightly unusual but nice examples come to mind. First few years back, one of the infamous EE girls that were all over the review boards at the time. I was at the airport hotel and booked an appt. of course she shows 2 hours late (which was pretty much the standard for this agency.) dePite the late hour, we have a great time (she was incredibly good, particularly with oral). We are cuddling and chatting after and next thing I know she’s asleep. She must’ve slept for 20-30 min, and I even dozed a bit. Eventually woke up we said our goodbyes. It really nicely capped off a great session that started out on the wrong foot.
Second more recently, a girl I see often (who also does bdsm services). We have a great laid back GFE time and are cuddling having a drink and chatting. She says “you know, sometimes I’m surprised how different my job is client to client. Earlier today I was having one of my slaves clean my house, then later getting paid for butting cigarettes out on another guy. Then I have a session like this. I mean, don’t get me wrong, I like the kink stuff a lot, but sometimes I just wanna suck a dick, ok?” (I knew then I’d found the perfect girl. Lol!)

 

[sp free]

Going to be tough to top the garbage bag anal fisting.

 

[massman]

Going to be tough to top the garbage bag anal fisting.

No point in trying.