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How do I initiate things with his more mature, older brother?

Tagged as: Dating, Sex, Teenage<< Previous question   Next question >>
Question - (10 September 2008) 3 Answers - (Newest, 10 September 2008)
A female United States age 30-35, anonymous writes:

i started casually hooking up with this guy about a month ago nothing too serious, i guess we both kinda got feelings so we started hanging out more and getting closer (i met him within my large group of guy friends) but last night we had sex and he couldn't get it up/keep it up (he's 23) n it was TINY! needless to say it really turned me off to him entirely..I've always had a thing for his older brother that i now want to pursue but i don't know what will happen or how to go about it..mind you the brother is in a relationship for 3 months now..help! i really want to try things with the more mature brother...

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A female reader, rainbowcupcakes United States +, writes (10 September 2008):

rainbowcupcakes agony aunt

maybe you just need to give it another try. the same thing happened to my boyfriend, he couldnt keep it up the first time and he said it was because he was nervous, he wanted everything to come out right and he had been imagining that moment, That when it came it basically collapsed, HAHA! which i laugh at now, but that moment it wasnt so funny

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A female reader, birdynumnums Canada +, writes (10 September 2008):

birdynumnums agony auntYesssss...

Well, then. Perhaps it was that he sensed you "weren't that into him" or that He might have been afraid that you might Judge him, but of course, You are a much bigger person than that... Just think, Wouldn't it be grand if you and his older brother hooked up, and then you spent the rest of your life with him? I imagine his brother and the rest of his family, especially his Mother, wouldn't judge you either!!! Not!!! Life is so much better when we think things through and make decisions based on love, trust and respect, and not on the size of a guys tallywacker.

Never date a guys family or friends, that's just a disaster waiting to happen. You can't get there after where you have been. Guys don't like talking to other random guys who have been with their girl, so how would a brother ever deal with "Hey, by the way, how is that tattoo that she has on her inner thigh?". Honestly? You must realize that this is wrong to even consider going after him, otherwise you wouldn't have written. 13 year olds don't know any better, but at your age, you should, Hun. This has disaster written all over it.

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A reader, anonymous, writes (10 September 2008):

well first of all if his older brother has been in a relationship for 3 months and is happy i dont think you should try with him, you may destroy his girlfriends life completely which is not at all fare on her. maybe you should leave it and see what happens, another guy may come along any day. also maybe you should try to actually get a relationship instead of casually hooking up, its not all about the sex...

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