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If he goes onto cuckolding oriented Reddits it seems like everyone enjoys cuckolding when in fact it is relatively uncommon. If he expects you to enjoy the same kinds of things that the people on his kink sites enjoy then he will likely be disappointed. \n\nIf this is a kink you dont share and that makes you feel bad you need to say no and be emphatic.\n\nIf this is a thing he needs, he will need to look for a future partner who is into this.\n\nYou need to accept that you may not ever be compatible in this way. To be clear, this is a big issue, not just a small one.
All depends on if she left that part out deliberatly. Never assume or prejudge. Ask her about her past with him and why she wants to play with him. If she had an emotional connection, that's a risk element to consider.
People do have different styles. I tend to stroke her for ages and then try my luck moving to her breasts, mostly these days without success.\n\nHer style is to pull her top up, sometimes place my hand on her tits, or literally to put her hand between my legs.\n\nIn fairness she she has never said lets get this over with .