Most Awkward Session

[ConquerorRyan]

Hey everyone.

I have had many great session with many ladies over the years I have pooned, but I just wanted to ask this.

What is your most awkward session?

For me, it would have been really early on, maybe 2nd or 3rd lady that I ever saw. So I called up this agency here in Calgary, and asked for some company. We settle on a lady, and time for her to come over. About an hour or so later, she arrives at my door, and she is on crutches and has a bandage around her head. She mentioned that she had fallen down some stairs and hit her head, and almost broke her ankle.

She was very nice, but as you can imagine, couldn't move around that well, and was in pain for many of the positions we tried. After she left, I called the agency back and told them about this, and that I should have been more clear with them when I was talking to them. And even though I never said that a girl on crutches was out of the question, you would think they wouldn't have asked her to work that day. I told them that she was very nice, but that next time, I didn't want to spend time with someone injured like that. I have never called that agency back again.

So what is your most awkward session?

 

[Cardinal Fang]

:SayWhat?:

 

[Borey The Bald II]

You must be kidding?.

About an hour or so later, she arrives at my door, and she is on crutches and has a bandage around her head. She mentioned that she had fallen down some stairs and hit her head, and almost broke her ankle.

 

[ConquerorRyan]

You must be kidding?.

About an hour or so later, she arrives at my door, and she is on crutches and has a bandage around her head. She mentioned that she had fallen down some stairs and hit her head, and almost broke her ankle.

Nope, I wish I was kidding. Completely the truth. She had a driver who brought her to my place and picked her up afterwards. Like I said, she was really nice, and apologized a lot, but that kind of role play I am not into lol

 

[IFUSEEKAMY]

Oh my gosh Ryan. That was a cringeworthy session!

I have 5 that I can think of right away. Oh boy!

1) On Xmas break when I was a teen, I got extremely bored and went into a Yahoo chat room for webcam shows. Over the next 10 days, I danced in front of the camera and stripped to my bra and panties for those who filled up my Paypal account with $. Towards the end, I got a request from a guy who gave me 200bux. He wanted me to eat in front of the cam wearing pigtails and PJs. He then started saying the most vile vulgar incestuous things to me. I started crying. Which sent him over the edge and he gave me another 200. The fuck?

2) Two summers later, I was posting on CL and picking one or two men to meet from the various ones who replied. One of the guys whom I didn't choose to meet kept calling me weeks after. One evening when he got me on the phone, he insisted he really wanted to meet me. I told him I couldn't because I had hurt myself a couple days ago. He said it wouldn't bother him. True to his word, he didn't say anything about the way I looked.

Last year, he tracked me down online and arranged a meeting. I had no idea who he was until I saw him and it dawned on me. We had another "mind-blowing" experience again according to him (yay) but this time he kept bringing up MY BLACK EYE from the last time we met. I was so embarrassed. He apparently didn't believe my explanation years ago and he was still laughing about it now. I felt like an idiot.

How I got my black eye: Please keep in mind, I'm a HUGE klutz and without my glasses I'm pretty close to blind. It was summer and I was applying moisturizer to my legs. I ran out, and asked my friend if I could use hers. She tosses me a bottle of lotion. I miss catching it cuz I'm not wearing my contacts and it hits me in the face. For the next week, my sunglasses never leave me. At the time, my eye didn't look so awful to me but with my terrible vision suffering even more due to my injury, I must have looked really bad.

Ok that's enough rehashing for now.

 

[User-E]

Client had a leaky colostomy bag. 'Nuf said.

 

[chokemychicken]

I went to Montreal this past summer with my mom. My mom went out for the day and I wanted to finally break my sp cherry. I went through the Montreal paper and called an agency. The girl shows up, takes my $160.00 for the hour and then lays down the rules. No touching between the legs or bum, no kissing, no licking , no squeezing anything just stick it in and hurry up.

I told her to please give me my money back or I'm calling security. I picked up the phone while I was blocking the door and she threw 140 at me telling me the rest was for her driver. Needless to say I'm probably worse than Blank Dave when it comes to enjoying company.

 

[ConquerorRyan]

Client had a leaky colostomy bag. 'Nuf said.

lol yuk

 

[papasmerf]

Client had a leaky colostomy bag. 'Nuf said.

well next time you will not book with Dick Grason

 

[Madman]

well next time you will not book with Dick Grason

That's funny.

I had a session booked via pm and was told I look like my avatar, talk about awkward.

 

[Cardinal Fang]

Client had a leaky colostomy bag. 'Nuf said.

Fark! Sarah wins.

Honorable Mention to Ryan farking a car accident victim and Amy attempting to be a tomboy.

Jesus! I don't even want to mention mine now.


3.

 

[papasmerf]

Jesus! I don't even want to mention mine now.


3.

you hedging around about the time you booked Robin and to your dismay it was not the Boy Wonder :whip:

 

[socialstrat]

Client had a leaky colostomy bag. 'Nuf said.

I'm pretty sure nothing will beat that!

Back when I was new to all this and before I knew of the different review boards I frequented a wonderful lady at one of the more notorious spas. She mistakenly thought I was a therapist (I've occasionally done some mediation in the past) and during the session was telling me about her friend who'd been freaked out by a creepy customer who had said things that corresponded to a dream she'd had. The friend was convinced she was going to die. While I was in the shower afterwards she left and came back with her semi-hysterical friend, naked from the waist up, and explained that I would help her. So I start spouting some psychological bullshit in an effort to calm her down and this friend - I'm pretty sure she was either drunk or high - suddenly pulls away my towel, starts grabbing me and trying to make out with me. At this point my regular MPA gets annoyed because "he has his education" and she's "not being classy." I was awkward but also pretty awesome. I miss that place sometimes.

 

[User-E]

Fark! Sarah wins.

Honorable Mention to Ryan farking a car accident victim and Amy attempting to be a tomboy.

Jesus! I don't even want to mention mine now.

3.

Please Cardninal, do share ... :smiling:

 

[Gooby]

Most awkward at an MP:

Some coworkers of mine convinced me to go to the wedding of another coworker even though I didn't want to go. The wedding was at a banquet hall in Mississauga and that particular day was quite hot. The food was really good but it was spicy and I think i had a little more than I should. I decided I would sneak out earlier than most of the others but on my way I figured since I was near Brampton I would head to a nearby MP.

At the MP I do the usual business i.e. pay for the room, get undressed, shower etc. As soon as I step out of the shower I feel something give in my stomach and I felt like I need to take a massive dump. Just then the MPA walks in and I think to myself that I guess I have to hold it in for the session. The only problem was that I was in a lot of pain and that was preventing me from getting junior up. So through the start of the session the MPA noticed I was uncomfortable and couldn't get it up. She figured it might have been my first time. About 10 minutes in I tapped out and told her the truth.

So then I had to walk to the toilet and did my business. By then I came back showered and we figured that we didn't want to continue. Was a real waste of money plus I felt like the MPA and the other girls had a little chuckle as I walked out of the place.


Awkward moment with an SP -

Back when I was younger I got my first job out of university working for a company downtown. I was making more money than I thought I would be at that age. Since I didn't spend a lot I figured I needed something to blow some money on. One day when I got out of work early I made a call to an agency for an in-call in the Bay and College area. The SP was a hot Russian girl that looked a lot like Elizabeth Banks. She got changed into a school girl outfit - short skirt, thigh high grey stockings, and hair tied up in pig tails. It had been my first time with a woman in about 6 months and just seeing her in that outfit already got my mojo going. She did a little lapdance and striptease and then got to work with a little stroking and a BJ. Around 2 minutes of light work in I finished. She had a laugh and told me to be better prepared next time. I was so embarassed and that time waiting for round 2 was probably the longest 10 minutes of my life. It was worse since she just kept staring at me tapping her foot waiting for me to get it up again.

 

[Tourist]

Years ago I called an agency and told them that I had a fetish for women that were accident prone.

I get a knock on the door and in walks this smokin' hottie with no problems what so ever. Had one on the best sessions of my life.


Have always wondered what happened to my date with the crutches and head bandage though. Hmmmmmm

 

[Cardinal Fang]

Please Cardninal, do share ... :smiling:

Back in 2002 I had an encounter with an SP at a hotel. She was from Quebec and came to Toronto on a tour of sorts. At this time it was rare for escorts to do incalls at hotels. I just assumed she was so worldly and all. About half way through our session that was going pretty well if I do say so myself she gets a call on the hotel phone. She picks it up and talks to this person on the other line. As she looks at me she makes a face and mouths the word FUCK to me. After she hangs up she throws me my clothes and tells me to go get dressed in the bathroom because her sister is in the lobby coming up.

As i scramble to get dressed she's telling me or yelling at me through the door that her sister does not know what she does in her off hours. My story was to be that we met when she used to work in Toronto 5 years before and that I was taking her out to dinner. When her sister came in I pretended like I was using the bathroom - this gave me time to finish getting dressed. I then spent the next 30 minutes making small talk with two women and avoiding getting caught in a lie. I then told them that we needed to get going and her sister finally left and said she would call her tomorrow.

After her sister left I tried to calm down but my nerves were fried. I thanked the woman and excused myself. She offered to return a portion of the money but at this point I was happy to just get the fark out.

 

[Kirk Lazarus]

Years ago, I had an outcall at a hotel with an SP. Before getting to the action, I ordered room service. As I was heading to the washroom to freshen up, there was a knock on the door. I assumed it was the room service so I asked the SP to let them in while I went to the washroom. When I came out, there was no food, but another girl in my room. I didn't want to assume that she was an SP so had some small chit chat trying to figure out what was going on. Finally, we figured out that the girl had gone to the wrong room when her booker called and asked where she was. She excused herself and left the room.

 

[Casa_Nova]

I'm sure this has happened to a few of you.

A long while ago I was at one of my favourite establishments, seeing a new girl on their roster. The girl was nice and things were progressing nicely until we decided to switch positions and as I pulled out, I noticed that the dome was well...a little red. She was mortified and thought she was still a good day or two away from when her "friend" was suppose to visit so this was completely unexpected for her. Being a new girl and knowing that I was a regular with the agency probably made her a lot more nervous than she needed to be. Though part was since we were at the middle of the session, little head was still eager to go - we ended up doing a BJ/HJ combo as I don't think either one of us were comfortable continuing on having sex.

 

[ConquerorRyan]

Years ago I called an agency and told them that I had a fetish for women that were accident prone.

I get a knock on the door and in walks this smokin' hottie with no problems what so ever. Had one on the best sessions of my life.


Have always wondered what happened to my date with the crutches and head bandage though. Hmmmmmm

lol, so you're the one who broke her lol