Initiating a First Timer

[Writer]

For context, I’ve been pretty into TUGs for a while and surprisingly while conversing with my vanilla friend the other day, he mentioned that he was interested in trying out something like this but never had anyone to trust. I volunteered myself naturally and he surprisingly agreed.

Granted, we won’t be able to really meet for a while due to our schedules, but I’m wondering what the best first tie should be to initiate him and show him the ropes. He told me he just doesn’t want to have it be painful, and we’ll be talking about limits and things closer to when we actually solidify a date, but I want to be respectful yet explorative.

Should I use a gag for the first time, toys, tickle him, etc. Any ideas and scenarios would be greatly appreciated.

[captured_prize]

For ties, just put him into the different positions without actually tying him to see if he would at least be comfortable like that. If you want something more specific, try a box tie or having his wrists crossed. As far as gags go, you should first let him get used to being tied first before applying any gags. Then see if any gags are of particular interest to him. Toys might be a lttle intimidating the first time and as far as tickling or scenarios, just discuss it with him. Present different scenarios and see if one catches his fancy.

[Cleavegagger]

I am in a seminar situation, albeit it being my new partner being the one interested in being tied, gagged and toyed.
For me an excellent starting point was the position she most fantasized about, taking things from there