This is long, but please forgive me. I want to be detailed to get the best answers in response. Please don't laugh. I'm new here and not using to typing such detailed information. I'm usually a reader... :-/ But, I have a question and I would like opinions please. From men also.... I read in so many places about instering a finger in a man's anus during oral. Okay, well...I decided to try it this weekend. The first time I tried it, during oral I had one hand on his balls and decided to kind of just move a little lower, and just get REALLY close, not not really GO FOR IT, to gauge his response. I'm 33, and in a relationship with a 22-year-old who has very limited experience, not that I have so much myself, but I knew he'd never don't anything like that either. So, he didn't try to stop me, and he seemed to cum faster than normal. I wasn't sure if I was imaginging it though. His only comment really, was, "I was wondering how much closer you were going to get." So, that evening, I decided to try it again, but I didn't mention it, because I thought he would say not to. So, during oral, I kind of gently moved his leg a little to the side for access, and to see if he said, "WHOA!" He didn't stop me, so I moved his leg a little more and very slowly barely placed my finger to the opening. I wasn't brave enough to go for full insertion. He definitely had a reaction. He let out a few moans, and while he normally strokes my hair, which is long, there were a few noticable tugs...not YANKS, just tugs, and he came VERY quickly. I now considered this a confirmed reaction. So, after completion I waited a minute and then asked him, "You okay?" (He was quiet.) His answer was:" I am soooo confused." Now, I was not surprised by this. He's young, fairly shy, not real outgoing in the bedroom, but I think that's just because he's only had sex with his high school girlfriend, and the they didn't experiment with much. He is getting a bit better about the shyness in the bedroom, but I still sometimes have to say, "You know, we can try different positions. I'm VERY flexible" things like that. I also read that many many are a little freaked out by the fact that they enjoy the sensation. They think it makes them less of a man, or whatever. I asked him if I hurt him, and he said, no, but his pride and ego were a little in shock right now. I told him, "look, if you really didn't like it, I won't do it again, but from your reactions, you liked it." He said he wouldn't go so far as to say he liked it and that the jury was still out. I said, well, just don't close your mind to something just because it's different. There are nerve endings there, and it's as simple as that. I said, okay, tell me this, did it feel good? He kind of sheepishly responded in a lowered voice, "Yeah, it did." So, today I finally brought the subject up again and said, about that...it felt good to you, even if you don't want to admit it. I told him, look, I know you're a man, andyou think you aren't supposed to like that sort of thing, but it's okay. A lot of people do it. I said, well, would you want me to do it again, or should I say would you let me? (I thought maybe he would want it, but not want to admit it and therefore ALLOW it and just not ask for it. does that make sense? I hope it did...that was a little jumbly) So, he said, "Just, next time...make sure you wash your hand afterwards." I said, "baby, when I got up and went in the bathroom, that's what I did, you just didn't notice becauase your mind was still fuzzy." OKAY!!!!!! So, now that I finished my long narrative, if you have any comments...please give them. But, I have a few questions. 1. Is his reaction normal? The confusion, not sure if he liked it, wanted it again, whatever.... 2. IF I do this again, I would likely want to take baby steps for him. How far should I go?? Fingertip? The length of the nail bed? To the first bend in the finger? Do I just judge and see what he reacts to? I'm new to this also... 3. I have nails, not long, but should I use a finger condom? Or will this feel differently? 4. Lots of lube, little? (The firs two times, there was no ACTUAL insertion, so there was no lube and it was kind of unplanned.)