I've got one friend in particular, Krista, that I talk to about my sex life in graphic detail. I keep her posted on almost a daily basis. Steve's okay with that, and he's really not shy at all. She's mildly sexually experienced, and has been asking me a lot of questions about giving fellatio lately, as I tell her about doing that quite often, and about my occasionally having orgasms from doing it (which I'm learning to harness; yay!). I recommended some good porn videos with examples of good oral (and because she's fresh out of a relationship ), but she's not really into pornography, and is afraid that she doesn't really know what she's doing ONCE she's doing it; so imitation is hard for her. She's given handjobs to orgasm before, but says she's never made a man cum with her mouth and is afraid she's been looking like a fool for the last several years. Maybe you see where this is going... Yesterday at lunch, we were talking about all the sex I threw at Steve the night before, and she just kind of blurted out like she'd been sitting on it forever, "Would you mind if I watched you give a blowjob?" I was speechless for several seconds because it totally took me off guard, and she seemed to be very nervous and really embarrassed right away. Then she just started nervously talking, that she's afraid she's not doing anything right, and she's probably been looking stupid forever, and how she just thought since she knew me and Steve that it would be okay. Then she started back-tracking fast, saying how she hoped I didn't think less of her, and how she should never have asked, and how she hopes I can still be her friend, and how sorry she was... ...and I'm still just sitting here speechless the whole time not able to get a word in even if I could talk. So finally I get her to stop and tell her that she just caught me off guard, and it's just something I had never considered. We sat and had a long talk about it and I finally said, "Let me think about it; but we're definitely still friends. (lol)" And that seemed to calm her down a lot. So I get home yesterday and make out with Steve in the kitchen for about 15 minutes before I strike up the conversation, asking him if he ever thought "being watched" would be sexy. Then I told him about the conversation and he was just as taken back as I was. We mulled it over and decided that as long as neither of us thought it would hurt our friendship with her, that we didn't think it was too "out there" and that we'd be willing to help her. My question here is, how many of you have ever done anything remotely like this? And what do you suspect the effect to be on a long-standing friendship? She's generally a moderately shy girl, and neither Steve or I have a shy bone in our bodies. Thanks to all who contribute.