What is your biggest regret, or missed opportunity?

[Cruiser]

If you had a do-over, what would you use it on?

For me, it was at (not important, as a dozen return visits I never saw her again) on my 3rd or 4th time going to a semi-legit. I was getting a massage from a 30ish, slim, but maybe 15lbs plump. Asian of course and CUTE AF. The massage itself was good, but with limited teasing. Enough that I knew I'd leave happy but not so much that I was rock solid on the flip. But once I got to the flip, constant bumps, rub over and squeezes. For longer than most before getting down to business. Probably 15 minutes on my back before she asked the question. Her english was terrible though, and communication was hard (as was I after 15minutes of on the back teasing) Rather than the usual "Massage here?" question, she bluntly asks "You want cum?" Duh.....My rock hard 5inches on a good day, should tell you the answer to that! Then she said something like "gibberish 120 dollar....gibberish $180 dollar" I asked her to repeat, but no luck in understanding. I had a good idea what I could get for $120, an so I said "$120 please" She looked disapointed. But she started on the a-typical $120 activity, which was wonderful as she was taking her time. She made intense eye contact the whole time and I was already planning my weeks schedule for a return visit. Rather than the typical "moaning" like she was getting off while stroking me, which I always hate as its so fake, she tried talking to me. Like "You think pretty?" To which I said "You are so pretty, the sexiest massage I ever had" (not a lie, as her personality made her the sexiest). Lots of other pillow talk in broken english which is so darn cute. Best part is she was soooooo slow in stroking that it lasted forever. "You cum where?" I'm sure she said that, but couldnt beleive it so asked her to repeat. "You cum where?" So I said the only thing I think respectful 'Where do you want?" She says, "where you want?" Ok......

Time to no longer be a gentleman. I am sure I am not misreading the room, so I go for it. "I think you are so pretty, I would love to cum on your face" She looked confused and asked me to say again. I do the international "pump it on the face" gesture....to which she says "Ok....200 dollar"
I'm like SOLD!!! I have $200 cash, and have always wanted to cum on a womans face (pathetic to say, I never have) She got one of the hot warm towels to start washing off the LG. Not sure why... was she thinking a BJ was part of this? I wasnt going to complain. But then, every mans worst nightmare. The excitement of the proposed activity....the good 45 minutes of light to SEVERE teasing. The 10 minutes of language barrier pillow talk while getting a slow handjob, and the friction of the warm wet towel, I blew my load in the towel while she was cleaning me. Was she going to blow me to a facial? I have no idea if that is what she thought we negotiated, but it sure as fuck was what I negotiated! I asked her name, she said "Sara" The next Thursday (this was a thursday) I texted to book with Sara, and was told no Sara works there. I returned a dozen times over the next few months, never saw her again. So that is my biggest regret....My lack of bat control while batting with runners on base. Those clutch situations separate the HOFers from the AAA players.

I am still "facial free" so if you know of a semi legit send me a PM lol

Anyways, like a chump, I still paid her $200. I mean, the thought was there, and frankly, I think I got my moneys worth. But it set me up for unreasonable expectations, as I have apart from one offer for a BJ, never came close at a semi-legit. (I dont do notorious FS, as it just isn't for me)

 

[Owenglasses39]

About 7 years ago at Meridian, I was shown into the back room and a small kind cute girl came in, it was summer and hot, so she was wearing a sundress. Thinking this is a very refreshing take on the normal massage attire I told her how beautiful her dress was and laid down. She said "thank you Ben"... I think.
I said you're welcome and brushed it off. "what type of pressure you want today Ben" for sure I heard Ben this time. I said relaxation please and she goes "always relaxation" with a smile.
So the massage is going great and I'm thanking Ben for even existing as this point because the tease and shit is on point. I flip and she doesn't use oil and starts running her fingers over my chest and cock. She grabs my cock in her hands and says "ready" I was like fuck yes I read go. And she proceeds to slide my cock into her mouth, and I'm like oh my days what is happening right now. Ben my hero, you made this happen. But I got a guilty feeling. Like what if this broad usually wears glasses and today she forgot them and can't see me right and thinks I'm Ben or some shit. I stopped her and told her I wasn't Ben and that it may just be another person that looks like me or I look like him or some balls. She is in shock and turns red and stops. She's says (no joke) "I'm sorry only HE for you I only do this with Ben"
Is Ben even real? Does she only give blowjobs if you play along and be Ben? Does she have some sort of a Ben fetish? Do I really look like this mf?
Whatever it was I fumbled. F*ck you Ben and that pretty sun dress that still haunts me

 

[m694ever]

My biggest would be breaking off my FWB relationship with Vivian. Was inevitable eventually but should have hung in there longer than I did. Very strong yet weak woman both at the same time. Those that knew her well know exactly what I mean.

 

[Albertaman]

My biggest would be breaking off my FWB relationship with Vivian. Was inevitable eventually but should have hung in there longer than I did. Very strong yet weak woman both at the same time. Those that knew her well know exactly what I mean.

A few other guys in Edmonton and in Calgary are probably rolling their eyes reading this .. they bravely carried on with their FWB friendships with her, until she decided to disappear


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[Qster]

This is more of a funny story than a regret story, but the older I am, the more I wondered what would have happened if I left my bed. At exactly 2:48am on a Thursday night, with work the next day, I was fast asleep, phone rang, number I don't recognized. Thinking it may be a work emergency, I picked up, a drunken female voice spoke up:

Hey Rocky, I'm home and I'm horny, come over and bring a bottle
Ummm, not Rocky
Can't remember your name then, you were at Midway, you were cute, do you want to come over?

I wasn't at Midway so I went back to sleep but always wondered...

 

[Qster]

A few other guys in Edmonton and in Calgary are probably rolling their eyes reading this .. they bravely carried on with their FWB friendships with her, until she decided to disappear


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Never regretted a minute of it until she disappeared.

 

[UserNameTaken]

Most of my regret or wonder what would have happened moments occurred in my private love life, not so much in my massage/escort encounters.
Privately life speaking a person looks back and asks themselves, what the hell was I thinking? But, at the time the big head over ruled the little head for whatever reason. The risk was way more than the reward? All dependent on the situation. Getting caught pumping the slut aunt, would have turned out bad if caught or outed.
With masseuse or sp"s the regret usually was, why didn't I see her more when she was available or I missed out completely.

Never regretted a minute of it until she disappeared.

 

[Wills_willie]

My biggest regret was when I was 13 or 14 and it was summer school break. I'm home alone and our German neighbor, not the best English, likes to do her yard work in short shorts and tank top. I would go out and sit on the step and watch her or peek at her from a window. She noticed my voyeur peeking and at some point she switches to wearing a mini skirt. So while bending over, which she did a lot, I got a pretty good view, couldn't sit on the step anymore as I couldn't take the strain. Then one day she knocks on my door and asks to borrow a tool, so she comes in and I run downstairs to get it and when I come back she's kneeling at the top of the stairs. This time no bra and she leans forward, I get a great view. Long story short I'm to shy to try anything but stare as she smiles at me. She leaves and I just turned it into a fantasy. Still think about that situation and wish I had a way-back machine .
A bit more recently, about 6 or 7 years ago. I did a walk in to one of the newer Asian places and was greeted by a somewhat familiar face. Anyway, I get on the table with no cover she walks in and giggles, slaps my ass and asks "relaxing massage?" . Too me that's the signal for HE. The tease was awesome and at the flip she leans over, gives me a light kiss, and whispers "do you want to fuck me". I FOUND THE UNICORN!!!!. Well, guess who shows up? That 13 year old shy boy and I turn her down, WTF. I went back many times but that offer was never made again .

 

[UserNameTaken]

My biggest regret was when I was 13 or 14 and it was summer school break. I'm home alone and our German neighbor, not the best English, likes to do her yard work in short shorts and tank top. I would go out and sit on the step and watch her or peek at her from a window. She noticed my voyeur peeking and at some point she switches to wearing a mini skirt. So while bending over, which she did a lot, I got a pretty good view, couldn't sit on the step anymore as I couldn't take the strain. Then one day she knocks on my door and asks to borrow a tool, so she comes in and I run downstairs to get it and when I come back she's kneeling at the top of the stairs. This time no bra and she leans forward, I get a great view. Long story short I'm to shy to try anything but stare as she smiles at me. She leaves and I just turned it into a fantasy. Still think about that situation and wish I had a way-back machine .
A bit more recently, about 6 or 7 years ago. I did a walk in to one of the newer Asian places and was greeted by a somewhat familiar face. Anyway, I get on the table with no cover she walks in and giggles, slaps my ass and asks "relaxing massage?" . Too me that's the signal for HE. The tease was awesome and at the flip she leans over, gives me a light kiss, and whispers "do you want to fuck me". I FOUND THE UNICORN!!!!. Well, guess who shows up? That 13 year old shy boy and I turn her down, WTF. I went back many times but that offer was never made again .

Exactly the type of situations that you think about when laying in bed late at night. Totally agree, being too shy or too much of a gentleman will get you memories of what if?
Found out that hard way....when a lady makes a spontaneous pass or naughty suggestion you have to respond in kind as usually that opportunity passes like water under a bridge.

 

[Darke Steele]

My biggest regret was when I was 13 or 14 and it was summer school break. I'm home alone and our German neighbor, not the best English, likes to do her yard work in short shorts and tank top. I would go out and sit on the step and watch her or peek at her from a window. She noticed my voyeur peeking and at some point she switches to wearing a mini skirt. So while bending over, which she did a lot, I got a pretty good view, couldn't sit on the step anymore as I couldn't take the strain. Then one day she knocks on my door and asks to borrow a tool, so she comes in and I run downstairs to get it and when I come back she's kneeling at the top of the stairs. This time no bra and she leans forward, I get a great view. Long story short I'm to shy to try anything but stare as she smiles at me. She leaves and I just turned it into a fantasy. Still think about that situation and wish I had a way-back machine .
A bit more recently, about 6 or 7 years ago. I did a walk in to one of the newer Asian places and was greeted by a somewhat familiar face. Anyway, I get on the table with no cover she walks in and giggles, slaps my ass and asks "relaxing massage?" . Too me that's the signal for HE. The tease was awesome and at the flip she leans over, gives me a light kiss, and whispers "do you want to fuck me". I FOUND THE UNICORN!!!!. Well, guess who shows up? That 13 year old shy boy and I turn her down, WTF. I went back many times but that offer was never made again .

Dude....WTF???

 

[Albertaman]

This is more of a funny story than a regret story, but the older I am, the more I wondered what would have happened if I left my bed. At exactly 2:48am on a Thursday night, with work the next day, I was fast asleep, phone rang, number I don't recognized. Thinking it may be a work emergency, I picked up, a drunken female voice spoke up:

Hey Rocky, I'm home and I'm horny, come over and bring a bottle
Ummm, not Rocky
Can't remember your name then, you were at Midway, you were cute, do you want to come over?

I went back to sleep but always wondered...

You might be living that alternate life with a whole bunch of little Qs now all grown up, and a much older hard drinking lady yelling out her commands


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[Wills_willie]

Dude....WTF???

EXACTLY!!!!

 

[Qster]

My biggest regret was when I was 13 or 14 and it was summer school break. I'm home alone and our German neighbor, not the best English, likes to do her yard work in short shorts and tank top. I would go out and sit on the step and watch her or peek at her from a window. She noticed my voyeur peeking and at some point she switches to wearing a mini skirt. So while bending over, which she did a lot, I got a pretty good view, couldn't sit on the step anymore as I couldn't take the strain. Then one day she knocks on my door and asks to borrow a tool, so she comes in and I run downstairs to get it and when I come back she's kneeling at the top of the stairs. This time no bra and she leans forward, I get a great view. Long story short I'm to shy to try anything but stare as she smiles at me. She leaves and I just turned it into a fantasy. Still think about that situation and wish I had a way-back machine .
A bit more recently, about 6 or 7 years ago. I did a walk in to one of the newer Asian places and was greeted by a somewhat familiar face. Anyway, I get on the table with no cover she walks in and giggles, slaps my ass and asks "relaxing massage?" . Too me that's the signal for HE. The tease was awesome and at the flip she leans over, gives me a light kiss, and whispers "do you want to fuck me". I FOUND THE UNICORN!!!!. Well, guess who shows up? That 13 year old shy boy and I turn her down, WTF. I went back many times but that offer was never made again .

You wouldn't be living in Beaumont area at that time? One time, a supplier took me golfing so I was in a foursome with three members. At a long par 4, all three of them pull their shots to the left over the trees. I kind of went wtf and asked if that is the short cut, they just all smiled and said yes, there is a big safe opening behind the trees. So I shot it in that general direction as well. As we drove up, my cart mate simply said it is a tradition and pay attention to the blue house. Sure enough, as we stopped to hit our second shots, a topless 30 something European milf was doing yardwork and waved, not shy at all. As we drove away, "too bad she was doing yard work, if she was tanning, she would be bottomless as well." Despite a bogey for the hole, I did not regret pulling my shot intentionally.

 

[Wills_willie]

You wouldn't be living in Beaumont area at that time? One time, a supplier took me golfing so I was in a foursome with three members. At a long par 4, all three of them pull their shots to the left over the trees. I kind of went wtf and asked if that is the short cut, they just all smiled and said yes, there is a big safe opening behind the trees. So I shot it in that general direction as well. As we drove up, my cart mate simply said it is a tradition and pay attention to the blue house. Sure enough, as we stopped to hit our second shots, a topless 30 something European milf was doing yardwork and waved, not shy at all. As we drove away, "too bad she was doing yard work, if she was tanning, she would be bottomless as well." Despite a bogey for the hole, I did not regret pulling my shot intentionally.

Nope, not sure Beaumont was much of a village back in those days , let a lone have a golf course.