Is it bad to put my hands down his pants? How far should or shouldn't I go? I am worried I will regret my actions and I wouldn't know what to do?

[Anonymous]

My first boyfriend and I have been together for about 5 months and I really like him but not sure if I love him. He is really gentle and caring and doesn't want to pressure me to do things. Yesterday while messaging on the phone I joked about wanting to put my hand in his pants. He said I already did as I put my hand in his pants pocket once. Does that count? I was just wondering if it would be bad to do that when we are making out and I wouldn't know what to do. I am very sure we both don't want to have sex or at least I don't want to before getting married, and we don't want to go too far or regret anything. He said he also wants me to be innocent and doesn't want me to regret my actions. I'm not sure if we're in the stage of the relationship but he said he wouldn't mind if I did put my hands in his pants and he would too if I wanted to. Also I have pressure or advice from my dad and family not to get serious. And to start off as friends. I think we were already friends for 3 months before going out and told my parents about him when we were already dating. So where would the boundary line be between being friends, being bf and gf or being serious? Please give me advice on this. Thanks.

[Questiongirl101]

Im in the same situation and im just going to go for it today when i meet up with him. The worst that can happen is he'll pull away if its awkward then its there fault for saying they wouldn't mind if you put your hands down there pants!

[RichardBoehner]

Yes if you grope him on the outside of the pants until you feel him getting hard, then you can stick your hand inside and pull it out and do whatever you want with it. Just dont grab his dick and not suck him off. thats just plain evil.

[i1T2daty]

Either in his pants or his had on outside his pants grip it stroke and he will come. Many girls "like" polite and gentle guys but are much more turned on by the guy that wants to fuck you and let's you know w/o asking

[robertraff]

It's more about more of your ok with it then anything else. So if you are go for it feel him down there.