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Anal Intercourse

  • “Many thanks for your advice in the past. You have always helped me stretch my horizons (amongst other things) and once again I seek your wisdom.From my previous correspondence you may...  more»
  • “This is a taboo topic that I have been hesitating to ask about, but I feel that you will not be judgmental in your advice.Of late my boyfriend has begun to delight in a peculiar sexual...  more»
  • “I had sex two days ago and my buddy's condom came off while still inside my ass, but before he came. At the time I wasn't worried because I figured the condom would come out. It still...  more»
  • “My boyfriend and I have intercourse regularly and since we are monogamous, we don't use a condom. I am always on the bottom and achieve orgasm 99% of the time without either one of us...  more»
  • “As a newcomer to anal sex, I wonder, how deep can a dick be planted up the ass? My partner's is a 9 incher and I'm worried if he gets it more than halfway in that it will damage...  more»
  • “My fuck buddy is a really fit guy, not some 9inch monster though. He's got a real average, good looking thick cock -- obviously this is all great. The problem is despite his average size...  more»
  • “I want to get fucked and enjoy it at the same time. It's as simple as that. But, whenever I try it with my boyfriend it hurts tremendously and I have to back up from doing it. So to...  more»
  • “My hungry ass is insatiable. How can I fulfill my anal desires and do something for the betterment of humanity at the same time?  more»
  • NEW » “I am 23 years old and about to get married to the love of my life (female). I have a curious side but I don't want to mess around with guys. I want to feel anal penetration performed on...  more»
  • “Thanks for the great advice you offer on your site. It's thorough, frank, and well-informed. Could you please enlighten me a bit on anal orgasms? When I first heard the term, I thought it...  more»
  • “Great advice column first off, really informative and answers a lot of questions I have/had concerning different areas of masculine intimacy. The new question I have now, has arisen with...  more»
  • “My lover is the macho type... he always wants me on bottom, which is fine by me. My question: Is anal sex physically damaging over the years?  more»
  • “I was just wondering, what is the best lube that isn't supposed to be a lube (i.e. Vaseline, vegetable oil, etc.)   more»
  • “Can you please explain the proper use of the word "fuck"? Does fuck mean the act of slamming your cock into an orifice, or does it mean spooging your manjizz? Every time I go down on my...  more»
  • “I would like to be fucked by my new lover, but I hesitate to do it because it's very painful. Do you have a solution?  more»
  • “Can sexual roles be so frozen in your mind so that you just cannot flip the switch (in my case) from bottom to top? I'm struggling with endurance issues when my man wants me to top him....  more»
  • “My partner and I have been together for 9 months. I have been sexually active for, gosh, as long as I can remember, but he's a bit of a newbie. We're both in our mid-30s. I have always...  more»
  • “I'm still a stranger to anal sex. I tried doing it with my friend. He inserted only two fingers and there was pain in that area. I tried relaxing and the pain still remained. I tried...  more»
  • “After anal intercourse, I find I get swollen and even a little shaky back down there, and it is uncomfortable for almost two days. We lubricate with KY jelly. Is there something I can rub...  more»
  • “I have a new fuck buddy. We are both married men and monogamous. We have anal intercourse. I am 58, he is 52. He can come 4 or 5 times in an hour; it happens every time, to my great...  more»
  • “How can I make my cock taste sweet? I once sucked a guy off that had the sweetest cock I ever tasted. How the heck did he do that?Thanks. My cock is awaiting your answer. :)  more»
  • NEW » “Only once have I cum while my bf was fucking me. It feels great but I can't seem to recreate this again. He really wants me to cum while he's inside me but I can't figure out why I am...  more»
  • “You have always been a good source of advice and information for me, and my partner and I have greatly benefited from the information in your column. I have a question about lube...  more»