After reading that great post advice from a redditor, I decided to try this again, this time with a bit more effort :)

About me:

• 6ft brown eyes, fit (gym daily, but not super buffed).

• Good looking, good sense of fashion, handsome overall.

• DDF, very good hygiene, STI free.

• I’m located Toronto.

• Not in a relationship. I currently have a job that wouldn’t go well with this lifestyle, so I’d like to have this be discreet!

• I am a pretty respectful guy, who will always prioritize how you feel first, making sure you are comfortable with whats happening.

• Laid back/open minded personality.

What I’m looking for:

Plain and simple, I’ve always been into women older than me (above 30 years old). I could use the term “milf”, but not looking for someone who has kids necessarily. My fantasy consists in the age gap of someone young and “new” to life (me) that meets someone grown, mature and experienced (you). Having the privilege/luck to be flirting with someone older than me and that person be interested in me as well. I have a preference for asians, but I don’t mind any race as long as there is attraction. It will start as a ONS, but if there is chemistry and we both like it, would love to turn it into a FWB type thing.

I guess you could consider me somewhat of a sub at first while in the flirting stage, and perhaps I like feeling like an older woman has power over me, that wants to have her way with me, but in bed I’m ready to switch it up and go full on dom on you, feeling like the envy of all my friends for achieving a fantasy many crave. I have a lot of experience and have been with older women before, who have been satisfied and impressed by what I know how to do with my fingers 🤞🏻 and the energy a young guy like me can have.

The plan:

As soon as we can, I’d love to chat with you, see if we are in the same page, then continue the conversation in a public space, like a cafe . Get comfortable with each other. The flirting stage is what gets me going, the anticipation of “something might happen!”. But I also want to get to know you! I don’t want to feel like we are just using each other as objects. Please be near downtown or willing to drive. Just to clarify, I am self sufficient and don't need a "mommy" or someone to take care of me.

Boundaries/kinks:

I haven’t tried a lot yet. You could say I’ve always kept it pretty vanilla, but I’m open to new experiences and something we both are comfortable with.

IMPORTANT:

As I mentioned before, I am new to this and have major paranoia for safety. I want to make sure the person in the other end is real. Therefore, I will be asking for your picture first, and some questions to help me determine you are who you say you are. We will meet at first in a public space and this is not negotiable. Safety first. If I trust you enough and things go well, I will invite you over, or will go to your place. Of course you can ask me anything you want as well. I’d be okay to do a quick call to verify ourselves too.

I think that’s it! I’m ready to have a good chat, good drink, good convo, good sex and finally good night with someone who is also into age gap. Crossing my fingers that this will work.

Thanks for reading! Hopefully this was good enough. And shoutout to that one redditor who took the time to write some advice for us men wanting to fulfill our fantasies.