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One to three guys for a I use all of them or me and 2 other guys. 

Jim, Jack and Jacob

mid 20s 

dick sizes about the same 1 to 2 feet long possible 3 feet
3 or 4 inches thick

History: These three have all lived in the same neighborhood, being bros as they hanged out with different girls at their school. They chose to be in the same college and even work place which is construction. All three of them has always loved Japanese women, all kinds of MIlfs, bimbos, shy, outgoing etc. These three tend to hang out even in Japan, which has all the anime Milf from Slice of life or romcom living in the same Japan. 
Since the shouen ones are more tricky to do, we can see if I will make all three in a modifed canon. These three are mainly used for slice of life/city roleplays. 

Personalities: 

Jack: is the one with the cock ring who enjoys pain as much as he enjoys pleasure, for any milf, cougar or lady is welcomed to peg him. As long is he is fucking another hottie in the pussy, is more the guy who enjoys breeding. Has more of a desire for making harems for breeding reasons 

Jim: He is more brass and rude douche bag, who takes what he wants. Can handle two or three ladies with ease and is the ladies man of the trio, knows how to give and take as much as he takes. At times will be a jerk knowing what ladies want. Not much of a breeder, unless otherwise as he is normally a bad boy, harems are desired 

Jacob: Even if he is more of a good boy then than other two, he hangs out with them based on working out, drinking, they have been friend since early grade school. He enjoys being with a soft Dom milf, courgar or bimbo. Wants to be with a real hot Japanese Milf, who is either a widow or her husband left her. Now he does have self respect for himself and won't be a simp. One woman at a time,