Post your best hobby memory.

[Mandalorian]

This might be a fun thread.

Some of us have been in this scene a long time. There must be one (or more) outstanding memory that was so good, you cannot imagine your life would be as complete without it, and all these years later it can still bring a smile to your face. You may have seen many girls since then, but you’re always chasing the dragon trying to find another hit like that one.

I’ll start:
I’ve been hobbying since 2001. Best memory was an encounter with one of my regular MPA here in Ottawa. It was during Covid lockdown and it was a huge no-no to be out of the house. She contacted me, said she was bored and asked me to session with her. I drove to her private home (until this time I have only seen her at the spa). It was a thrill to see her. As I took my shower she propped a chair in front of the glassed in tiny shower stall in her apartment, sat down in front of me and started masturbating, getting herself off as I was washing myself. It was such a turn on I couldn’t wait to finish and before I could even towel myself off she was on her knees blowing me to completion. After that round we went to the bedroom where she treated me to a very normal massage and another bbbjcimsw. I was completely drained after 3 weeks lockdown. We had a few more sessions before she retired and moved home and I have missed her ever since.

 

[PayForFun]

I had a great session with a SP. After we were done she asked me what I was up. I was just going to head home. She asked me if I wanted to grab a bite to eat. I said sure. We went to a restaurant, she bought me dinner, great banter and laughs, then we went back to her room for an even better session. It was an incredible night.

 

[ogibowt]

i went to a Terb party, years ago, at the now defunct House Of Lancaster on The Queensway, because i knew a regular was going, but she didnt know i was going
we exchanged pleasantries during the evening and she introduced me to some of the girls and generally i enjoyed myself
toward the end of the evening i asked her if she had a ride home to her incall..before she could answer i said i would drive her home if need be..she said ok, as she was going to take a cab...anyway we got to her place which was a set of stairs to her room,,,she asked me if i wanted to come up, i kinda hesitated because i had little $ on me...she sensed my hesitation and told me to just come up and chit chat.....i was there for a few minutes and she gave me the "goo goo eyes" and stroked my arm,,,i said something like "really, cause i dint come prepared"'...she basically told me to shut up..lol....we canoodled for a while..no FS, but a hand job was quite welcome...after a little time passed i told her goodnight, and left
i saw many times after that....and we never discussed the "freebee"
Believe me im no prize package, so i took it as a sign that we were okay with each other, and could be friends..lol....but i never got another freebee..lol

 

[BiggerTitsTheBetter]

My two best memories are already posted on Terb...
My very first time
Arianna DD as Harley Quinn

 

[Hybrid7]

My best sexual experience was with Georgia at Allegra. She’s so passionate it made me feel better than any actual irl girlfriend I’ve been with. The bed scrapped across the room and my out of shape ass was sweating buckets
I’d be in trouble if she worked more regularly.

My best holistic “date” experience I’m not gonna name because I don’t want to give the indication that this is normal. I had a very fun romp with a provider who invited me to sit, drink, and chat with her for like a solid hour after our time was up. She must not have had another appointment for a while and I guess we clicked on a personality level. It felt disarmingly intimate; a rare blurring of the typical transactional client-provider relationship.

I told her to her face that I might need to take a break before seeing her again because I’m worried about getting addicted Now that I mention it, I think enough time has passed that I’m due for a repeat.

 

[Ryan_Coke]

Very early on in my hobby days, I was at an industry event in London. I was so nervous going there but I met a lot of great ladies that led to awesome times. One of the ladies put herself across as a "higher end" lady, she was there in a business suit, and she did charge a little bit more compared to the prevailing rate of the day (I think she was 250 an hour when everyone else was in the 180-200 range), so I guess not outlandishly expensive. But she played the part well and I was instantly attracted. I started following her on twitter. I noticed she was always posting about going out for drinks and I made a comment about why she was buying her own drinks, that she would never pay if I was there or some corny thing. She gave me a wink back, so I took a shot and slid into those DM's (even though I don't think they called it that back then lol) and said I was serious and told her we had met at that event a couple months earlier. So she told me where she was going to be and I said I will flag you down and told her what my board name was from the old London board.

I arrived before she did and sat at the bar where I could the comings and goings. It was actually the strip bar she used to dance at before getting into escorting. So she walks in, I nod at her as she walks close by and tell her who I am and I follow her to a table. All of a sudden, the guys at nearby tables stop watching the stage and start looking in our direction. After the first drink, she starts teasing them by running her hand up my leg. Anyway, I start to realize this girl can drink. Fortunately I don't drink booze so this wasn't turning into that expensive an endeavor. During our conversations through DM ahead of this meetup, I had said my birthday was coming up and I wanted to book her for that, which ended up being a week after this "date night" as it seemed to be turning into. We stayed there a couple hours, and she asked if I would mind driving her home. Well, ok, if I have to, put a gun to my head. As we left, she said she was hungry, I offered to take her out for a bite, there was a Kelsey's nearby or somewhere else if she wanted. This is where she was a cheap date, and just said there was a Wendy's by her apartment. So, anyway I pull up to the front of her building and tell her it was really nice to meet her and I was looking forward to my birthday evening with her the following Saturday.

But wait, there's more. She says "you can't leave your car here". I was confused, and she said, "let's go to visitor parking. Don't you want to come in?". So, like the post above, I'm thinking I don't have the cash for this. I hesitated and she said "it's fine, let's go". Remember, I'm still pretty new at this, I've seen maybe 5 escorts over the last 6 or 7 months by this point. And I'm also thinking "Just because she's an escort doesn't mean she won't go pick up a guy for her own fun, but why fat old out of shape me?" But whatever, I'm here for whatever she's up for lol. I park and we go into her apartment and she gives me a nice long hug in the kitchen. She takes me into the living room and she has a bunch of certificates and stuff on the wall. She is in her last year at law school at Western and apparently she's pretty smart lol. I also at this stage of my hobbying thought it was strange she would reveal her identity like that to me, who she just met hours ago. We sit on the couch and she snuggles up to me and starts rubbing my leg. I'm naturally sitting there in disbelief. The reality of my immediate situation hits me that I was sitting there drinking pop all night and I really needed to pee but I didn't want to interrupt what was going on. Finally, I have to excuse myself. I go take a quick leak, and she's standing in the hallway when I come out. I say I really enjoyed meeting her (again) and again, there's more. She asks if I have anywhere I need to be, she knows I'm married. I say no, I have an alibi until the bars close. She says it's been a while since she had anyone cuddle her to sleep. Am I being pranked here or something? Bedroom is right there and in we go. She gets undressed and crawls into bed, me still being all unassuming, I go to lay down beside her and she says "Uh, no street clothes allowed in my bed" lol. Alright, I've played the unassuming rookie hobbyist long enough, this hot babe is inviting me into her bed, I'm a grown man, I know what to do lol. Stripped down and under the covers before she has much of a chance to look at me and change her mind, I snuggle up with her. She simply says " I hope you don't cancel next Saturday because of this". Hell no. Well, we did everything a paid GFE session would be, and I'm lucky I didn't fall asleep there with her. The following week was awesome as well, but it was paid, so a completely different feeling. I still follow her on twitter today, she has long since left the business but she has done very well as a lawyer. 13 years later, I still remember that night like it was yesterday.

 

[unassuming]

3 comes to mind of so many:

1- Circa 1990- Had a session with an SP. She was BBBJing me, it was a nice long sensual type, I was gonna explode and warned her "I'm gonna cum soon" .....I Then nudge her head back as not to unload into her mouth and said "I.m cumming", She ignored my warning and sucked me dry. We then cuddled for a while and I can hear her sloshing around my huge load in her mouth and then I hear "Gulp" as she swallowed it all. CIM was very rare back then and to get a swallow!. It was the first time an SP swallowed me.

2- 2011-An agency had a new girl on schedule, She had not been reviewed yet, her menu said GFE .
I like to be edged during sessions (alternating between BBBJ , missionary and doggy) and blow my load near session end. She told me she had only one condom. So after removing condom after several rounds BBBJ and mish and doggy I tried to put the condom back on but to no avail. She then said "I feel bad for not bringing more condoms, you can cum in my mouth" It was music to my ears! as I love exploding into SP's mouths. I fired 4 rounds in her mouth, she had to pull off, it was a huge load as some of my cum went into her nostrils , she then went back to sucking as I fired more shots , She sucked me dry.

3- 1990- went to a MP place at Bloor and Spadina, It was in an office building, I enter the suite, 3 girls come out, 2 pretty young blondes and a pretty young brunette, I was to choose one of them, I chose one of the blondes, she led me to the room, where she said she'd back in just a moment. So I'm lying naked on my back on the table after getting undressed . All of a sudden all 3 of the girls come in, the girl that I chose asked "Do you want all 3 of us?" I said that I didn't bring enough cash, to which she replied "Oh, don't worry about it!" Had a great session with six hands on Jr. I then ran into the girl that I chose at an agency in call , she had become an GFE SP, . During the session, I asked her why I got 3 girls for the price of one at the massage place, she replied "you were the treat of the day", meaning they did it only for guys they found attractive.

 

[curvluvr]

I haven't been hobbying as long as some of the guys above, but my best memory is meeting my favourite SP at a fancy hotel downtown for a session.
I still can remember most of it, play by play.
Hoping for a repeat soon.

 

[xix]

Very early on in my hobby days, I was at an industry event in London. I was so nervous going there but I met a lot of great ladies that led to awesome times.She simply says " I hope you don't cancel next Saturday because of this".......
Hell no. Well, we did everything a paid GFE session would be, and I'm lucky I didn't fall asleep there with her. The following week was awesome as well, but it was paid, so a completely different feeling. I still follow her on twitter today, she has long since left the business but she has done very well as a lawyer. 13 years later, I still remember that night like it was yesterday.

Your story sounds like one of my ex-coworker, every 2 weeks she would do this at bar ( when kid wasn't home ) pick up a guy and go through a script, something like yours. She always invited me to be there but I said no thanks. I knew what she was doing. Yes she did quit doing this once her stomach got big and had enough rosters of men. Which they call her now a days. She was not normal, hence why she did this, and had money from inheritance.

I left that work place, she retired from work ( at 52 I think ), I see her every 3 years to talk but no monkey business. Yes she still tries. BTW she was never a SW unless she was in her University / college days. Maybe one day I will ask her.

 

[seanzo]

My favorite memory is of all the time I spent with Tiffany Black. I was heart broken when she retired

 

[princekwekua]

It was 2010 when I booked an escort from Hong Kong. She was here on a 6-month visa. Early 30s, really well put together: pretty, firm everywhere. She became a regular and I would bring her gifts from my travels.
After 3 months here, she made me a proposal. She had made enough money and wanted to enjoy the rest of her 3 months here with me without escorting. We can hang out and sex as often as I wanted without payment. I signed up without hesitation.

It was a blur for 3 months. Restaurants and intense sex nonstop. It is the best 3 months of my life. And then it all came crashing down. Since her visa was about to expire, she suggested we should get married to extend her stay. And then what, I asked her? For real, permanently was her answer. So that was her intention all along. And here I thought it was all altruistic. So it ended and I paid her ticket back to Hong Kong. But it was a blast fondly forever remembered.

 

[Mandalorian]

Seems like a theme here are moments where the SP lets her guard down and shows her non professional self with some unexpected (but appreciated) freebies.

 

[unassuming]

Another: mid 90's, saw this SP at an agency, a few times , she was a dark haired brown eyed beauty elegant looking, then she went indy , I found her by accident through her ad in the papers, She was pleasantly surprised when I booked her for a session.During breaks in the long session, through chit chat, we discovered we went to same high school at the same time, she was 3 years behind me and was a cheerleader. She told me what her nick name was , and i knew who she was immediately, she was very slender back then with beautiful long legs, I found her very cute.I had a crush on her then and would look at her every time she would pass me in hallway. She felt that she was an ugly duckling back then. I told her she blossomed into a beautiful swan. She said that I always kind of looked familiar to her. The next session, I brought in a year book, for her to look at, we had fun reminiscing about teachers and other cheer leaders. She'd be in her early 60's now.

 

[soca]

Reading some of these stories.... I'm clearly doing something wrong.

 

[xix]

Reading some of these stories.... I'm clearly doing something wrong.

 

[massman]

Met a hot Eastern European stripper, took her to the vip. Things were getting pretty hot and heavy, and I realized I was about to run out of cash. I told her I only had one song left in my wallet, and she said “fuck the money” and we continued to play for another hour till we were both spent.

 

[unassuming]

The Mirage Bus rides to many industry parties , agency meet and greets: DFKing a lot of the SPs!

 

[Velvets]

I once booked a legend that used to visit from Montreal. Had never seen her before.
I skipped out at lunchtime at work to see her for an hour.
One of the most fun hours I ever had. We talked about personal things and she bitched about how bad her agency was. She decided on the spot to quit working for them.
We got along so well that She asked me if I wanted to come back to hang out with her after I finished work. Who was I to say no ?
I returned after work and we shared dinner (sushi was her favourite). We ended up talking for most of the evening and she asked me to stay overnight and was clear she wasn’t expecting payment for this.
We ended up talking, with some naked wrestling thrown in. A genuine connection.
One of the best nights I’ve ever had !
I showed up at work the next day in the same clothes … lol
Next time she was in town as an Indy, I of course booked with her. Was looking forward to seeing her again but she ended up cancelling last minute due to a family emergency but she promised to make it up to me.
She kept her promise the next time in town and I paid for an hour but she did an overnight with me again.
We did this a few more times on her visits to TO until she ultimately retired.
Some of the best memories !

 

[drlove]

So many… I’ll start with my introduction to the industry back in the day. I was apprehensive and didn’t know what to expect. I called Select, and Greg who was a driver at the time actually spent 20 minutes on the phone with me, explained everything and put my mind at ease. I’ve never forgotten that.

Another time, Danny at EC really stepped up to the plate and offered me a free session after a bad experience. Then there was the time that one of my favorite regulars (who looked like a cross between Jenny McCarthy and Melissa Joan Hart) took me out for lunch off the clock.

I had another lady (Indy) spend extra time with me as well (was totally not expecting it) I paid for an hour and she ended up staying for four! I took her out for a nice dinner (least I could do), but it ended up feeling more like a real date.

Another time, I saw this girl at a downtown hotel. She actually worked at a Hilton Doubletree and was coming to see me after her shift ended. She was still in uniform, so she took a quick shower to get ready. In the meantime, I ordered us some room service. Now, the suite I was staying in had a glass bathroom door that you could see into which happened to be by the entrance of the room. She was still naked, drying off when room service arrived. Not wanting to be seen, she dashed out into the living room and hid beside a large armoir! The attendant had no idea, and I was trying to keep a straight face the entire time hahaha…

Then there was the time I was perusing a genuine dating website, and came across this hot 20 something blonde in my area. Unfortunately, I knew she was way out of my league so I didn’t even bother to try and hit her up. Fast forward a few weeks later, and I decide to give my favorite agency a call. The receptionist said she had a new girl on the schedule, so I said send her over… Well, imagine my surprise when I opened the door to find that it was the same girl from the internet dating site lol. Hit the jackpot that night!!

There were also socials where everyone on various boards got together to mingle. One memorable night ended in a hotel room with a bunch of fellow hobbyists and SPs, who started giving out free blow jobs lol

Then there were all the complete smokeshows that I had the luck to meet. One was a former catalog model, Some were amateur porn stars, some were from overseas, and one in particular was a girl who was featured on the Southern Belles porn site back in the day. She actually asked to use my pad for a photoshoot! I was tempted, but ended up declining since I didn’t want to draw any undue attention to myself.

Another time, I was seeing a group of SP’s from the same agency who happened to be friends. They’d gone to this all night rave a few days before, and one of them got completely wasted on a drink called Groove - it did not end well! Haha… Anyway, I saw one of her friends, who asked me to play a trick on her since I had an appointment booked for the following day. She wanted me to pretend that I had ordered up some Groove from room service. Well, you should have seen her face! She almost turned green… I didn’t have the heart to continue with the charade, but I made sure to tell her who put me up to it!

Another time, I rented a suite on the second floor of a hotel downtown with one of my favourites. We ended up doing it right by the window in the hopes that someone would look up and see us, but no one did… I’ll leave it at that for now!

 

[Brightside89]

My first time with @Kate Collins in Summer of 2025