I met up with an escort last night, (haven’t seen her for over year, but before that we saw each other frequently). We get on really well which makes this confusing… we are friendly and have each other’s numbers, and social media’s so unlike how l would assume an escort would act.
Whilst we were in bed, kissing and getting handsy we had the condoms on the night stand ready to go and before I knew it she has guided me into her raw – which I didn’t mind (I’m clean) and I’m assuming she is to (I’ve grown to trust her). She asks during it if I’m okay to pull out, which I say yes to and I do every time we had sex last night.
I’m struggling to understand the reason behind it. We’ve never gone raw before and honestly I would probably like to continue going condomless with her. However the way she acted felt more like the way a couple would act; lots of kissing and cuddling and we both didn’t want to leave afterwards.
Should I bring up the conversation with her? Or just leave it.
I like her, and I don’t know if that screws with the client/ customer dynamic or if there is something more going on behind the scenes.
Dude. Going raw with an escort is absolutely insane. Full stop.
She is an escort. That is her job. The product she sells isn’t just sex — it’s the illusion that you’re special, desired, connected. She has to make you feel wanted so you keep coming back and keep paying. The kissing, the cuddling, the “don’t leave yet,” the raw sex — that’s all part of getting you emotionally hooked. That’s her business model.
I’m not shaming sex work. But confusing a professional experience with a real relationship is how guys end up heartbroken, financially wrecked, or Googling treatment options at 3 a.m.
You’re reading way too much into behavior that is literally bought and paid for. You’re building a romantic narrative on top of a transaction. You’re trying to turn customer service into love.
If you want to keep seeing her as a professional, go for it — but keep your brain turned on. Use protection. Set boundaries. Don’t act like raw sex means she’s secretly choosing you over all the other dudes she sees.
If she went condomless with you, she probably goes condomless with other clients too. That’s not intimacy. That’s a giant WTF are you doing with your health risk.
So don’t romanticize this. Don’t convince yourself you’re the exception. You’re not her boyfriend — you’re a client. And the second you forget that, you’re f*cked in ways that have nothing to do with sex.
Pull your head out of your hormones and treat this situation with the seriousness it deserves. Otherwise, you’re one impulsive night away from a very uncomfortable doctor’s visit and an even more uncomfortable emotional reality.