A: I don't believe its technically cheating, but it is still rude as h*** and a horrible thing to do to both girls. It is most definitely disrespectful and I would dump a guy for pulling that.
A: Slow is definitely the key. Lots of lube is also a recommendation. It may hurt. A lot, at least it does for me, but the slower you go and the more lube you use the less likely it is to hurt. Don't tense your muscles, and if you do have him pause till you relax again.
A: 93 does sound very high for your age. But personally I don't think it matters as long as you are careful and don't act irresponsibly. I don't believe in sharing the number on demand. If you are comfortable telling someone your number, and if they are comfortable with knowing, it'll come out. I'm not... more