I started seeing this girl every few weeks. She doesn't really think of herself as an escort. She has a day job that she cares about and describes this as something temporary until her career moves forward. I met her through one of her friends and she has become a repeat overnight provider on trips.

Bro, I'm sure she seems nice and sweet and she says all the right things, but she doesn't have feelings for you, she NEVER will, if simply because of how you met. You need to move forward and expect nothing more from her than you would any other escorts. Simple as that! there will NEVER be a "thing" between you. Even if you progressed to an "Exclusive SB/SD" relationship, as soon as the cash stops flowing so does her pussy. Ride it out as long as you want, just know that it will never be anything more than a fun business relationship

Some providers, like myself do develop feelings for their clients. I am a rare breed indeed. I love my friends! I don't have any issues being honest. It's normal to love the people who care about you emotionally, physically & financially.

But on the other hand, is life just about being safe?

I suspect you will get deluged by players--myself included--who will tell you to back away, splash some cold water on your face, and move on. Nothing--I mean NOTHING--in your post even hints that she has any non-business interest in you. Suggesting you go to a party she may be at sounds akin to recommending a restaurant she frequents.  

Plenty of mongers have been able to parlay close relationships with providers into OTC time as evidenced by the many threads and posts here over the years! Many guys, particularly those with no experience in this realm have been burned! If the provider is unethical, she may take advantage of your feelings and willingness to help. Go into it with low expectations. I think the first step would be to broach the subject of OTC time, perhaps dinner. If she’s not game to see you off the clock, then just enjoy the good sessions you are having! If things progress, check the threads here for ideas how to set rules and boundaries. Personally, I’ve had a small handful of long-time providers who hinted at OTC time, but I always decline. Despite having had some interest a few times, it creates a level of complication I am not interested in.

We don’t truly know your situation. If you like her shoot your shot about dating. If she’s like hell no there’s your answer. I suppose you are risking the friendly rate she’s giving you. Life is short go for it.

Don't be that guy. But if you do you'll have lots of company.

But facts are facts. No one can deny your feelings. If you don’t take a chance and let her know, you will regret it for the rest of your life. But history tells us your odds are not great. But it also tells us it’s not impossible. Good luck.

-- Modified on 3/28/2026 10:12:20 AM

You're giving her money on a regular basis to spend time with you.
You're apparently in denial about her being an escort when you say she doesn't consider herself one because she also has a RL job, but you also mention she has an ad rate.

I've  found  that  the  lines  become  blurred
in  the  minds  of  Clients  &/0r  Providers
when  the  tryst(s)   are   so  amazing  they're   blinded  by  the  ecstasy......  

You've gotten (and will continue to get) plenty of warnings here.  My advice is:  Nut up and ask her.  But, go slow.

Let's say she does like you, what do you envision happening?

I see that some replies suggest a go-slow approach. I was responding based on the fact that he provided zero evidence she's actually interested in OTC time with him. If there are data to the contrary, hopefully he can be an adult and follow through accordingly.

you understand that giving her money is part of your relationship.  I am talking about a monthly allowance.  Start at four figures; AND

I agree but nothing ventured nothing gained. Plus, it’s not my life 😂

less than her normal rate is because you must be a fairly easy appointment for her, relatively speaking, you are booking multiple-hour sessions, and you have been loyal, regular and a dependable income stream.  When a customer is all of these things they will periodically get discounted rates or some OTC time piggy-backed onto the session.  These are customer-appreciation marketing gestures to keep you're coming.  If you try to read something else into it, you are most likely headed for a very awkward moment at some point where you pour out your feeling for her that might embarrass her enough to stop seeing you.  The only thing else "going on" is that she really appreciates your business, but that's the key here, it's all about the business.   That doesn't mean she wants to stop.  On the contrary, I'm betting she would keep seeing you on the same terms for months or years, or until you do something to blow the good deal you have.  

If you are catching feelings think of this, she probably has a real boyfriend that shes banging bareback and when you go down on her you are eating his creampie.  Get out now before you blow too much money.  She's using her best marketing tactics on you

You took what is probably a bad idea for him and concluded she's barebacking her boyfriend before sessions and leaving creampies he's eating. I'm laughing too hard and it hurts lol.

Yeah not sure where that cum from …

Can’t you enjoy each other’s company and care for each other within the boundaries of your existing and clearly enjoyable set up, without assuming that that means that you need to escalate to a Real Relationship?

Drop the feelings and put your big boy pants on. This isnt a game for immature adults that dont have their emotions in control.