Go for it! You're being given an opportunity and if he's serious he'll let you go it alone uninvolved, otherwise it's just a creative cuckolding for him despite what he says! If he's a grown man he'll be able to handle it, my wife let me off leash 3 times and while it led to a string of mistresses believe it or not we learned a lot throughout that time. But lay down every detail before starting between the two of you and only agree to it if you feel comfortable, know also ahead there's always a risk of having feelings for the other lovers which can make it much more difficult. Best of luck in your journey!

 

If you don't go through with it he will probably feel really loved to be fair. If it was me I would tell him that I'm not gonna go through with it cause you don't want to affect the relationship. Who knows maybe in a few months to a few years he will bring it up to you. But I really think he's just trying to understand where you are coming from and trying to make you happy.

 

It feels in a way like he's trying to seem as though he is giving me his blessing but then putting enough restriction in place to make it practically impossible. As I said there is only 1 friend with whom it would be possible and I'm not sure I'd be comfortable crossing that line with such a good friend. Do you think it would be unreasonable of me to say to him that if he was really happy with it he wouldn't mind who it was? Or do you think it's the control that is making him more comfortable? At the minute it feels like being teased and encouraged to go for something that is always kept just out of reach.

 

I most certainly believe as his lover he should have an opinion, but only in the way of concerns not a long list of provisions and limitation? Which would tell you that he is too immature to handle it and at the end of the day it's your body that will be intimately involved in that you run the highest risk. Although the wife and I have talked extensively about safe sex (for example) before she let me off leash I was told, "just don't fall in love!" In that she ran the highest risk of loss and love can be unpredictable, so I was specific to my mistresses that our relationship was just a sexual one and that I was married with kids with no intention on leaving them!

As far as fucking a friend, I wouldn't but again at the end of the day this is your choice and no one else!