My Gf Fulfilled My Darkest Fantasy

My girlfriend and I have been together almost 5 years now. We met just after we were both divorced after marriages that lasted each about 10 years. She was 39 and I had just turned 43 years old.

We instantly connected in SO MANY ways, not the least of which being our sexual open-mindedness and adventurous spirits. There hasn't been much we wouldn't at least TRY. As we got to know each other a little better, I noticed something that, quite frankly, shocked the hell out of me!

Things that seemed rather "expected" (at least from my perspective) absolutely blew her away! Here's an example...the fact that I prioritized her wants, needs, desires, etc. was (no exaggeration!) an absolute foreign concept to her. I mean, simply planning out fun dates for us to enjoy caused her, on at least two occasions that I can recall, to (literally) dissolve into tears of joy. I was having a really hard time comprehending what was actually going on because this stuff wasn't anything more than " Bare minimum" that a boyfriend should do. I hadn't even started spoiling her like I was planning!

As time went on I learned that she had NEVER been treated anywhere close to "well" by the men from her past. She's been lied to, "used", victimized in ways I'd rather not get into, and it goes on and on.... When I finally comprehended the depths of her "reality" to that point, I made it abundantly clear that "those days" were OVER!

No longer was sex something in which she was "expected" or "obligated" to participate. From here on out, I made it very clear that if she EVER just "went along" with something, because she thought it would make me happy, even though it truly made her uncomfortable, nothing could ever hurt me more. She saw how seriously I meant that, and while I cannot adequately put into words just how excited she was to enjoy her "new reality", suffice it to say, she finally believed that "happiness" might no longer feel like an unrealistic goal.

To be perfectly honest, I was BEYOND surprised that she would even be willing to TALK to a man again, much less TRUST a man again after all she had endured. But thank God she believed she could safely trust me. she showed me SO much trust that about six months into our relationship, she shared something with me that she had never felt "safe" discussing with any former partner, due to fear of judgment and ridicule. That "something" turned out to be her deepest and darkest fantasy. Despite a, shall we say, "quite experienced" sexual history, she had never experienced a threesome before. Her specific fantasy was an MFM scenario, where she would be pleasured by two men at once. It was just over a month after disclosing this fantasy to me when I saw to it that her fantasy was fulfilled, As luck would have it, she seemed so excited to tell me that the "real thing" was more fun, more rewarding, and even more exciting than she ever imagined in her head. From then on, I was absolutely determined to make each and every fantasy of hers at least "on the table" should she ever choose to make one a reality. During a conversation about my wanting all of her dreams to come true, she asked me about MY fantasies...

As it turns out, I was never one to fantasize about particular "scenarios", be it a threesome with another woman, or whatever. At first I struggled even articulating ANY fantasies of mine, beyond my desire to fulfill HER fantasies. That was all about to change. As I learned more and more about her past, a "scenario" kept percolating in the recesses of my brain. at first, it was just a few scattered thoughts, but over time, what REALLY turned me on became clearer and clearer.

There are SO many things I cherish about our relationship, but right near the top of the list is how we both feel perfectly safe sharing whatever thoughts or feelings or desires we have, without any fear of judgment. But the scenario recently dancing around in my head just might put the "safe/no judgment zone" idea to the test.

Her "past" hardly made any sense to me. She's so beautiful, so sexy, so incredibly bright, so kind, and the list goes on and on. How could ANY former partner not appreciate or respect this absolute gem of a woman, much less ALL of them?? And that's when the thought of her being appreciated, respected, desired, and...VALUED became SUCH a turn on for me. Due to its "unconventional" theme, this one particular fantasy in my head seemed far too extreme for even me (and my open-minded approach to life), so I tried my best to ignore it, hoping it would just go away on its own. It didn't go away. Quite the opposite actually...

It grew louder and louder and louder...to where ignoring it was simply not an option. I was simply embarrassed to tell her. At the same time, I knew that NOT trusting her with my fantasy was in fact disrespecting both her and our relationship. She repeatedly told me to come to her with ANYTHING I fantasized about, so I just had to trust her, regardless of how nervous I was.... Eventually, she could just tell that I was obviously holding something back, so she "called me out" and said "whatever you're not telling me....let's go...OUT with it!"

Sooo.... out it went.

"You know how I feel about your past, particularly how you were SO unappreciated by men until we got together. Well, the idea of you experiencing the, well... let's say, the "OPPOSITE of that" really turns me on! And while I know that you only really care about how I treat you or feel about you, it matters to me that you realize that I'm not the only man that acknowledges what an absolute treasure you are! It practically kills me that you can't see what I (and so many other men!) see plain as day. So I'd like to, um....actually PROVE all of this to you."

"And how would you do that?"

"Keep in mind that I am NOT at all encouraging, pressuring, or even suggesting that you do any of this. I'm just sharing a Fantasy that I cannot seem to get out of my head, so...."

" do you think you'll actually tell me the Fantasy sometime TODAY? Or this month?" (cracking herself up seeing me so nervous )

"Right...OK then, here goes....Whether on Reddit or somewhere else, we share pics and/or short video clips of you, in all of your super sexy glory, with a detailed and explicit description of exactly what we're looking for. And what were looking for is.... um, are you hungry? Because I could definitely go for tacos or..."

"OH MY GOD JUST SAY IT!"

FINE!! So for one night only, and that fact is CRUCIAL, you uh...work as a high class escort for only one client."

"So you want me to be a prostitute?"

"Hang on! Hold all questions to the end, please. So let's discuss what this lucky client is actually getting, ok? Sure, they are getting what's obviously expected from an escort, but they're also buying EXCLUSIVITY. This person will be 100% assured that you've never done this before, nor will you ever do it again. Also, you will assure this person, and your actions will no doubt back up your words when the time comes, that one thing you just cannot condone is someone walking away from an experience with you feeling like they either didn't get your BEST, or that they didn't get their moneys worth. I know you, and I know that's 100% accurate!

If we find a promising candidate, we will send them video clips of us IN ACTION, so they could see how fucking sexy, talented, sensual, and uniquely amazing you are in bed."

"Okayyyyyy, can I ask questions yet?"

"Nope! Still one very important element to this fantasy that I need to explain. Anyone can find a prostitute for about $200 an hour, all day long. A smoking hot prostitute could go for $300-500 an hour. And a super high end escort could easily set someone back $1000 an hour. You are going to charge WAYYY fucking more than that! For this to actually take place, it would take someone who both has a shitload of money, and cherishes the fact that he will be the ONLY ONE to EVER experience what he got to experience that night. You know how very rich people love buying rare pieces of art? Sure, they probably like the art itself, but they really love the fact that no one else gets to have it. OK, you can ask me one question before I go on."

"Do we tell them that I am in a serious and committed relationship with you?"

"Great question! We are going to be 100% forthcoming and honest about everything! And, believe it or not, our relationship will actually work in our favor! We'll absolutely tell them that THIS is my ultimate, deepest, and perhaps darkest fantasy. Once they witness how excited you get about turning ME on? Oh wow! Anyway, there's more to discuss .... Here are a few conditions they will be made aware of. They will be required to reserve two suites, right next-door to each other, at a luxury hotel. While neither of you would be able to see or hear me, there will be a few cameras set up so that I can watch the whole thing. After all, it is MY fantasy and I am not going to miss it. Also there's no recording allowed so they don't need to worry about that. We can tell them that YOU demand that I be next-door for safety reasons. If he turns out to be some lunatic, I can always run into the room and protect you..."

"I hope you understand that this is all very surprising and it's going to take me a little time to wrap my head around it, but I'm glad you told me about it. so my working as an escort night is a fantasy of yours?"

"No! And I'm glad you asked that because this needs to be clarified. Somebody willing to pay FAR MORE than it would cost for a night with ANY OTHER ESCORT because, like me and so many others, they recognize how special, unique, desirable and, well... VALUABLE, you truly are! What an incredible way to show you that how you were treated by certain individuals in the past was NOT AT ALL indicative of your value. It's merely just evidence of their stupidity and nothing more."

"I can't believe I'm saying this, but I kinda understand it now. Now what if the super rich guy, that sees my worth, is um.... unattractive?" (she giggles as she asks this)

"i've seen you when we have swapped with couples and had threesomes with guys you weren't exactly...into. OK so you haven't been sexually attracted to everyone we've played with, but don't forget this important fact. You get ridiculously turned on whenever you know I'm watching so your attraction to whoever this person turns out to be is almost irrelevant. You know, as well as I do that as long as they are respectful, act like a gentleman, and adhere to whatever boundaries you set, there's no reason to even be the slightest bit concerned about your performance while fulfilling my biggest fantasy."

" I can't argue with any of that! Remember that couple from San Fran? The wife with the huge tits that professed her love for your cock? Well I seem to remember that her husband had an obscene amount of body hair, was hung like a chimp, and wasn't physically attractive in way imaginable. He just kept telling me how beautiful he thought I was.... And he was so nice! Even though I couldn't have been less attracted to him, I still rode him like I was desperate to win first place at the rodeo. I definitely saw you watching me out of the corner of my eye and, well... yeah, he was the lucky recipient of ME performing for YOU. So I totally see your point. So when do we start posting our Ad, or whatever we're calling it?"

"Remember I'm just sharing my Fantasy here. This isn't something we need to do by any stretch of the imagination"

"You promised me that I never had to do that I didn't want to do, nor would I ever be expected or obligated to do anything, right?"

"Exactly! That's why I'm sayi..."

" I WANT TO DO IT! I don't know if you've considered this, but do you realize how bad this is going to backfire if we don't have any takers...oh no... no one VALUES ME!!" (again laughing hysterically while she's watching me squirm in my chair)

Three days later, the post went up. As expected, we filtered through a whole bunch of fakes, scammers, and broke men pretending to be rich just to see some free pics. The very next day however, someone who immediately seemed too good to be true, privately hit us up. He sent some pics, and then we made him send more and more pics until we were 100% confident that it was actually him. An older guy, maybe in his younger 60s, but I have to admit that he had a certain distinguished and handsome way about him. He had thick silver hair, and he was fairly tall and thin, like me. She loves tall and thin men ...

He told us that he owned quite a few businesses in the Northeast and that "finances" would not be an issue. We looked him up and, sure enough, he was who he said he was! (LOADED!) He totally grasy the dynamic of our relationship and he understood that this was only a one night thing. There would not be any contact or communication afterwards. He then voiced a few requests.

First, he wanted to FaceTime with her alone, with me out of "earshot". She looked at me, seemingly for approval. I reminded her that she doesn't ever need my approval regarding her behavior. If she's comfortable, I'm comfortable. She went ahead and they had their chat. She was upstairs so I went downstairs. After a couple of minutes, I l heard them laughing out during their chat. I assumed this could only be a good thing, and I was right.

A few weeks later, she and I were flown first class up north to meet him. Before either she or I could even say it, he assured us that NOTHING of a "physical nature" was remotely even on the table during this trip. And then it clicked... Of course, not! That would kill the "exclusivity". I have to say that he was an absolute gentleman in every sense of the word. He took us out for dinner at a nice steakhouse where he initiated a rather direct, yet respectful, conversation. The first thing he wanted to know about was her boundaries. While she certainly wasn't offended or uncomfortable by the situation we found ourselves in, she did kind of "freeze up", so I jumped in.

"The first priority is always safety. She doesn't want to catch any diseases or get pregnant, so that brings us to condoms..."

"Totally reasonable. Please understand that when I ask questions or seek clarity, I am NEVER challenging or debating your boundaries. That being said, years ago I had a vasectomy, so pregnancy is certainly not a concern. What if I were to have a blood test days before meeting up? Would that be an adequate substitute for condom use, assuming the test results are acceptable?

"baby, you know I'm comfortable with whatever you're comfortable with. It's your show."

"If you were willing to do all of that, then I am perfectly OK with it. Let's be honest, it'll be a hell of a lot more fun without condoms!" (all three of us dissolved into laughter)

then she chimed in with a question of her own. " this was all started because of his fantasy. Fulfilling his every want, need, and desire, turns me on more than anything. But... this is also YOUR fantasy evening. I would like to hear what you are hoping for. And you should know, I make it a point not to decide how I feel in the future until the future arrives. And by that, I mean to say that I'm not going to give you a bunch of arbitrary boundaries or rules that you must abide by, as I might feel completely different on that night. Conversely, I could tell you certain situations or activities are perfectly fine by me, only to change my mind when the time comes. So as long as you are respectful and communicate with me without making bold assumptions, we're going to be just fine. This is a one time only thing so I want you to appreciate just how important to me it is that you always look back on this night feeling like you not only "got your moneys worth", but that if you knew now what you will know then, you would have paid TRIPLE!" (she smiled, but she wasn't laughing this time. She meant every word.)

"Well I'll respond like this, I will never insincerely stroke your ego or try to protect your feelings. I am a kind, generous, and decent man, but I am also honest and forthcoming, and occasionally blunt when it comes to whether or not I feel I've received adequate value for my money. if it's worth triple, you'll know because I will pay you triple. The $15,000 that we agreed on will be wired into your account as you enter my hotel room. I certainly don't expect this or I wouldn't be going through with it, but if I were to feel that I got, say...inadequate value for my money, you keep the $15,000. If I happen to send you more it's only because I believe it was worth it. And also, as we agreed, should I ever learn about you having sex for money in the future, you agree to pay me damages in the amount of $250,000. To be clear, I know that's not going to happen but making the penalty such a large sum might be the DISSUADING FACTOR should you ever get the urge in the future. And just to make sure that I have this right, you will come to my hotel room at 9 PM and then I can end the experience at any time of my choosing up until 6 AM, is that correct?"

" oh dear, do you honestly expect me to stay up until 6 o'clock in the morning?" (giggling again.)

"Oh my goodness, no! But there's something truly magical about lying next to beautiful naked woman, while we both soundly sleep next to each other. That would be a wonderful moment should it occur, because it would mean we are both content, comfortable, and everyone feels safe..."

"Well shit! Now we can add you sleeping next to somebody, soundly and peacefully, to my fantasy! That sounded amazing!" (everybody laughing again)

The date was set for one month from our visit up north. The days flew by faster than any has month has ever flown by...EVER!

Our hotel suite was RIDICULOUS! Our new friend not only booked it for us for that night, but also the two nights after so that we could "reconnect" and make sure everything is OK. I was impressed! He didn't need to do that. At 8:40 PM, she was still undecided about which lingerie to wear. I asked her to try on all four outfits. What she didn't know was that I took pictures of each one and secretly texted them to the room next-door. Without hesitation, he responded with, "definitely the black one with the black thigh highs. See if she can wear some high heels as well, if possible. "

I was actually impressed. I was sure he was going to respond with, "whatever she feels most comfortable wearing...". I told her "you're wearing the black one, with the thigh highs, and I hope you brought some black high heels. Don't ask me why because we're not having that conversation right now, just trust me."

Even though it was right next-door, she threw a coat on before leaving the suite. We set up 3 phones so that I could see every square inch of the place, with 2 in the main room and one facing the shower and tub, just in case. It turned out to be a very good thing that I thought about putting a phone in the bathroom ...

She entered his room feeling incredibly nervous, but no one would know that from the seductive and sexy smile worn on her face. She walked right up to him, kissed him on the lips, and asked him, "would you be a gentleman and take my coat?" And like a gentleman would, he gracefully took her coat and hung it up in the closet. And then he motioned for her to come sit on the bed next to him. I was kind of surprised, thinking he wanted to jump right in...

Instead, he had a very low volume, almost whispering, conversation that I couldn't hear. She got a big smile and laughed, and it was obvious that she was very comfortable. And then they stood up and he poured a couple of drinks, then they continued their conversation, a little louder this time so I could hear.

He asked, "pardon me. I do not want to assume anything, but I would guess that you showered before coming over?"

"I sure did! I am all fresh and clean"