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Use lube. You have no idea how sexy male moans are. Start out by using a finger. Go slow.
I am a 42 year old man who ran into his old neighbor's daughter. Freshly graduated from college, and with no man in her life, she invited me to her bed. We had been fucking together for a few days, and we were both enjoying every minute of it. Tammy was an eager student, and I wanted to teach her all I knew.
Is there a more awkward conversation to have with your lady than finding a way to uhh The gritty details of the act don't exactly lend themselves well to being talked about over dinner. But you can't just try to slip it in when things are getting hot and heavy without asking, either. No seriously, don't try it. You'll get smacked.