The first time I fell in love with a non-pro / sugar baby / whatever...

T

TheRealStory

#1
#1
Given my post in the other thread - thought it might be good to dig deep and go back and tell the story of the first time I fell in love with someone I was paying for sex. This will probably take a couple of days to get out - so I would ask that you let me finish before commenting. Just putting this in as a place holder.

Stay tuned...
 
T

TheRealStory

#2
#2
#1

To begin at the beginning - this is sometime around 2005 or 6. I trade emails with a girl from CL - we tried a handful of times to set something up, but it never materializes. I didn't realize until much later that the girl in question - let's call her K - it wasn't the first time we had talked.

Months later - and her with a different email address (which is why I didn't figure it out earlier) - I place a CL ad. One of the raunchy ones you used to be able to get away with - like "I want you to meet me, get on your knees, lick and suck my balls until I unload all over your face...then do it again" sort of things. So a girl answers - we cut a deal, and then we meet at a midtown hotel - grab a couple of drinks to get acquainted. Then I send her up to my room with one of the keys and tell her to wait for me. She performed admirably - we had a really good time - and within 45 minutes coaxed 2 gigantic loads out of me, and off she went.

I was excited - as you all know, CL back in the days was hit or miss, but when you found a good girl, you tried to keep her (or at least I did). It isn't that I don't like variety, it is that the good ones are so hard to find (a mix of looks/chemistry/performance/reliability/etc) that if you let someone get away from you - don't keep them in rotation, someone else will snap them up. Very much like SA today, except that because SA is a site it isn't quite as random as fishing on CL.

My intent, with this one, was to keep seeing her.
 
T

TheRealStory

#3
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#2

A couple of weeks later, I had the occasion to be in NYC on a Saturday. Doesn't happen often, but had a few hours to kill. So I emailed K - wanted to see if she could meet. Sadly, she had other plans and said she couldn't make it. Oh well - it happens. So I decided to put up another ad - didn't have anyone else on the roster at that point in time. Was a little bit different ad - and guess who answers???? K.

Hmm. So I answer her back with an alternative email, and lo and behold - she can meet me at the exact same time she said she couldn't meet me. Normally I would just chalk it up to "Hey - the girl didn't really like me" and move on. But she acted like she had a great time - so I figured I'd play around a little. So we make a date, and she shows up. I open the door, and she is like "Oops"...

I invite her in. We sit for a few and talk - and then I give her the choice:

A) You can leave, no harm no foul. Still not sure why you said you couldn't meet when you clearly could. But she didn't seem to want to explain so figured I'd give her an out and never talk to her again.

B) You can stay, but if you stay, you have to be punished for your poor behavior. All of the sudden she sits up and says how? I tell her that I want a repeat performance of the other day - but you only get half of your fee. Take it or leave it.

She crawls over to me and gets to work - and if I thought she did a great job the first time - the first time was nothing. She was so turned on by the power play of the whole situation that she went nuts. When she was done - I ate her out for like 15 or 20 minutes - she came so many times she was basically useless when I was done.

And again - off she went, promising to be a better whore for daddy in the future. No more games.
 
T

TheRealStory

#4
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We continued to see each other from time to time - things escalating a bit - she really loved being dominated, punished, controlled - something that I didn't have much experience (or to be honest much interest in) with - but it turned her on so much that it turned me on as well. Turns out that she had a real job but didn't make much money (worked for a non-profit), lived with her boyfriend, didn't really "need" the money so much with a capital N, but it was useful (student loans, etc). But all of this was part of a "whore fantasy" she had - it really turned her on to be paid for and used by guys for sex.
 
T

TheRealStory

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#4

For some reason, I always wanted to get into her tight little asshole. I licked it, played with it a bunch, fingered it, and she was really beginning to enjoy it, but would never let me fuck it (she was an anal virgin). One day we were talking and I asked "How much would it take?" And she laughed and said - an extra $1500. I asked where the number came from. She said she just made it up. Figured it was too much that I wouldn't actually do it but maybe I would...

We talked about it for a couple of weeks and I set the terms:

- $1500 cash bonus, and I get unfettered access to your ass for as long as we are together. And of course, I would be gentle.

She agreed, and over the next few weeks, I worked on it with her until she finally was able to take it all, and over time, she absolutely loved being fucked in the ass and loved the feeling of being filled up with my cum. It turned out to be worth every penny.
 
T

TheRealStory

#6
#6
#5

She had to go on a business trip to Seattle. We joked that she should fuck around on CL and make some cash while she was away. She said that it would be so hot if I "pimped her out" - again - part of her "whore fantasy".

So I actually put up a couple of ads when she was away and arranged a couple of dates for her. Nothing crazy - everything worked out fine.

But when she got back, we got together - and then I made her service me for free, and give me a cut of the money she made in Seattle. I'm not sure she had ever been so turned on in her life.
 
T

TheRealStory

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I had to stay in the city after a work event - and although she usually couldn't stay over, her boyfriend was out of town himself - so we had one of our rare overnights - this might be 12-18 months into our situation at this point - hard for me to keep all of the dates straight given how long ago it was, but I remember which hotel it was, and remember nearly everything about this night as if it were yesterday.

After my event - we grabbed drinks in the hotel bar, and had an unbelievably passionate encounter - one of our best nights yet. At some point in the middle of the night, I feel her trying to arouse me, and while I was awake, I was in kind of a fugue state - just enjoying the sensation. After a few minutes, I feel her on top of me riding me, and I'm in heaven. My eyes are still closed, and I'm just letting her take me...

I feel some drops of wetness on my chest, and I finally open my eyes because I'm a little confused as to what it is...I look up at her, and she is crying. I ask her "What's wrong?" and then it happens...she blurts out "I love you!"...and sobs uncontrollably.

I came immediately...and so it began...
 
T

TheRealStory

#8
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None of this was an issue for me. It was super exciting. I was riding high on it. Sensory overload. We both had busy lives, but tried to spend as much time together as possible. Including more out of the bedroom time - dinners, etc. And she even figured out how to go on a couple of business trips with me. It was amazing. Then one day - she sent me a long email and told me she needed to take a break. It was too much for her with her boyfriend, etc. And I was devastated. We never texted, only emailed for safety reasons. And she basically went dark. I had never felt like this before. No real explanation, no sit down, nothing. Was like someone took the air out of the room.

And it was strange. I've never been a particularly sappy person. But she did a number on me. Nothing seemed to help - even fucking other girls. As soon as they would leave I would be miserable again. And I didn't ask for it to be this way - it was like she foisted it upon me, and I let it happen, but I didn't mean for it to happen, and then I'm in the middle of it and she just cut me off.
 
T

TheRealStory

#9
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About 3 months later - an email out of the blue - she wants to see me again. And we get back into it - and for the next year or so we go through 2 months hot and heavy, and she goes dark, and back and forth. It was like living inside a pinball machine. And I don't think she was doing it on purpose - it was that we were both in the middle of something that we both knew was a bad idea and wouldn't end well, but we couldn't help it. As much as I wanted to walk for good - I couldn't.
 
T

TheRealStory

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One day we are together, and she says that she is going to move home. She can't live like this, lying to her boyfriend, in love with a married man, etc. She says she wants to start over. Says she will see me when she can, but can't be in NYC anymore. So she is gone, but we are still talking, and every 2 or 3 months she joins me on a business trip. So not ideal, but the time we get is fantastic.

We make plans for her to join me on another trip, and while I'm waiting for her, her plane gets cancelled and she can't get another one. I'm figuring no big deal - she will come on the next trip. And it never happens. She meets a guy at home and lets me know that she has to stop seeing me. Again - no closure - it cut pretty deep. Wasn't as bad as the other times she went dark, but still couldn't quite move on.
 
T

TheRealStory

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About 2 years later - she texts me (we are finally at texting) and says she is coming to NYC. Wants to take me to dinner. We go out to a great restaurant in meatpacking - and she treats! Was a great gesture - and through some tears she gets down to the bottom of everything. How she was in love with me, how she wanted to be with me but knew she could never ask me to leave my family. So she had to go. Too painful to be in NYC with me there. She was engaged (to a guy she is still married to) and happy - but after dinner we went for a walk - and one last kiss. And as we said goodbye this time - I was cool with it - I got the closure I needed and I never sweated it again.

But it was one hell of a ride for sure...thanks for indulging me.
 
U

Uniquelyme

#12
#12
Good story. You gave her too much power. She would go dark and then you would respond quickly.

You shouldve when she came back waited a day or two then respond. Fuck it if she gets upset. She was turned on when you were being dominant which is the trait of a Man. She fell for you. That's fine but just like all people she did was a bit rude by going dark. So rudeness needs to not be rewarded. Just my opinion.

Sounds like you had a great time though.
 
T

TheRealStory

#13
#13
Uniquelyme said:
Good story. You gave her too much power. She would go dark and then you would respond quickly.

You shouldve when she came back waited a day or two then respond. Fuck it if she gets upset. She was turned on when you were being dominant which is the trait of a Man. She fell for you. That's fine but just like all people she did was a bit rude by going dark. So rudeness needs to not be rewarded. Just my opinion.

Sounds like you had a great time though.
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I don’t see it as rudeness. I see it as her inability at the time to deal with her feelings. As to the power dynamic - to some extent you can’t control it. The point of it to me is that I just ended up there. I could have made a power play but it wouldn’t have made me feel any better.
 
T

TheRealStory

#14
#14
An interesting conversation we had one day. I asked her how many guys she met off of ( that site I'm not allowed to mention). She said about 30. I asked her how many of them she saw more than once. She said only me. Apparently it was her MO to fuck and run. Except that I tricked her into seeing me again otherwise the whole saga may never have happened...
 
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h50

h50

#17
#17
The back and forth and especially without explanations or with conflicting explanations is the part that kills me about these types of things.
 
T

TheRealStory

#18
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h50 said:
The back and forth and especially without explanations or with conflicting explanations is the part that kills me about these types of things.
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Unfortunately I had to kill the email account due to an extortion attempt. So I don’t have any of the correspondence. Some of this would have been more clear had I had access to it. It was more than a decade ago and I got the high points. But there was a bunch of great details that I can’t cover because I don’t remember them well enough to do justice.
 
h50

h50

#19
#19
I was more referring to "and she goes dark, and back and forth" so I'm saying that the back and forth with these woman including them not explaining themselves kills me. lol
 
T

TheRealStory

#20
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h50 said:
I was more referring to "and she goes dark, and back and forth" so I'm saying that the back and forth with these woman including them not explaining themselves kills me. lol
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Ok I get what you mean. But we are dealing with real people with real emotions. People don’t always act rationally. Comes with the territory - frustrating as it may be.
 
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