This is a serious request for advice. This guy and I have been friends for about 20 years even though we live in different parts of the country. He does some traveling for his job and we are sometimes able to meet for a day when he comes within 100 miles of where I live (Philadelphia, PA). We have different backgrounds but we share many interests and spend much of the time we are together talking. Every year we manage an Adventure for several days somewhere in the country. The physical part of our relationship started out with chaste massage and worked its way from there. He is awkward and ungraceful in his physical approach and I end up doing most of the touching. He refers to it as me doing most of the work. I refer to it as me doing most of the play. He is on an antidepressant which makes it difficult for him to have an orgasm and ejaculate. He rarely, rarely can have an orgasm by genital massage so I have been (happily) teasing, licking and sucking his cock and balls. He eventually gets, not to orgasm, but sensory overload and I have to concentrate on another part of his body for a while. The last couple times we've gotten together I have been doing frot and also sitting on his erection and massaging it between by butt cheeks. (I love anal play.) He got the idea that I wanted him to fuck me and while that was ok with me it was awkward, but successful, for both of us. My cock is average (6" + or - 1/4" depending on how excited I am) but he is at least an inch longer and half again as thick. This last time he was just too, um, eager. The fellatio didn't "work" as usual, but it really primed him for fucking. He did some rudimentary gestures of opening me up by putting his thumb up my ass, then a finger, then two and I tried to give him some feedback but he was just too ready and made a couple of attempts at penetration. My responses were: "careful.." "slowly..." "I need more lube." and "Unnnngh!" The last attempt was successful for him, but he went from pressing his glans against my asshole to pressing his pubic pone against my asshole in three thrusts. I was gasping for air and it fucking hurt. I tried to give him a little feedback after we'd showered but his response was that I need to relax. (Well, "duh"!) I told him that he could help with that. Also, my ass hurt for two days. SO I want to be able to be better a giving a blow job, (partly to save my ass) but I can hardly put a notice in the paper: "Experienced tutor need for gentleman who wants to be able to give excellent and effective oral pleasure to another gentleman." I'm serious, folks, I've read the textbook and now I need the lab experience to go with it. How the hell do I get it intelligently and safely? Not by sitting behind some glory-hole, I hope... I know what works for me, but are there some universal physiological responses that I need to pick up on? The other question is: how do I prepare myself for anal sex if my partner isn't going to do it for me? (I've tried anal desensitizers when I've done some solo ass play with butt plugs, etc. and they did the job, but the creme also got shoved up inside where they desensitized parts I didn't want to be desensitized ) I look forward to the benefit of your experience and/or advice! Thanks.