New to it!

So me and my SO have been together 5 years and we are new to the cuckold thing. Hes always loved hearing the stories of me and my exes and listen to old recordings of me and guys I've slept with and it really turns him on. And myself as well. He really wants me to go with this guy I've been talking to and give him head or fuck him and I want to and I absolutely love having sex with men like him but it's like because he knows about it I'm nervous. I feel put on the spot. I'm great at sneaking around (I wasn't the most loyal woman before I met him, I'm a changed woman and only cuck with him so no mean comments please) any tips or advice is welcomed!