How about this. Next time you get into a make-out session, just start suggesting things. And you don't have to jump straight to "you up for anal?" Just pause during the making out, smile a bit and say "I'd like to take my shirt and pants off. Are you OK with that? Would you like to take them off for me?" You may run into something he's not comfortable doing yet, and that's fine. Tell him that's OK, and make a counter suggestion. "If you're not ready to take your pants off, that's OK. But would you mind if you just rubbed you through your pants a bit?"
Lex
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Make sure you give him some "Top Time" trust me or you will never live it down.
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I would just talk to him and see if he wants to play around. Tell him that there is no pressure to do anything in particular, but make the point of conversation that you want to know how he feels about this. Ask him if he is nervous or shy. Listen more tha you talk. Ask him what HE wants to do.
I bid NO Trump!
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I can see that i turn him on and he turns me on. i had him be on top of me so he could be in control and I saw the erection through his pants, so i can't figure out why he feels he needs to hold back. I had on a button down shirt and we were kissing and he unbuttoned it and i got his shirt off and then he just stopped.
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So what does he say about it?
I bid NO Trump!
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He doesn't have a problem messing around with my upper body. "He feels that once we cross that line of actual penile contact that I will just want more and more , becoming more sexual and less sensual. He says that once sex enters the picture then it begins to "encompass" the relationship. that he will want it and i will want it and it will take away focus from other things."
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