First of all Welcome and Good Morning.
Clearly not a HW nor a cuck, but do have some experience.
Starting in this life can be very daunting, but it should also be exciting and enjoyable too. Starting to chat to a random person is very difficult , would you walk up to a stranger in the street flash your tits and say how about it? Probably not I feel, unless lots of drink is involved.
The fear you have is normal, after all first dates can be very stressful.
So how to start.. don't go out immediately with the expectation your first chat/exchanged will be perfect, unfortunately many men will swarm and you could feel inundated and perhaps intimated as they all will demand naked pictures, start as slow as you feel comfortable.
Start in a chat room, say hello and either chat openly or select one or two private conversations.. don't be tempted to have more as it can be a deluge of messages.
Make sure you are comfortable , both in mind and physically, no point trying this if surround by prying people as you will be more receptive when relaxed.
Never be embarrassed by how you feel and don't hesitate to block people.
Finally be yourself, in cyber world you can be whoever you want.
Now your partner, is he truly into this or just likes the idea? Have you brought this into conversation , role play that you've just come back from being with someone ( or more?).. or perhaps suggesting that when out with friends you were approached, is he wanting you to take a larger cock? ... judge how you both feel in these scenarios as that will help judge how you both react when it actually happens..
Be safe and enjoy 😈