* Is there anything unsafe about having vaginal and anal penetration at the same time? That’s always been a fantasy of mine.

I’m not sure if you are speaking of two toys, two men, or one of each. In any case, if you are used to vigorous or rough sex in this instance I’d go more gently since you are stretching the tissue between the vagina and the anus and tears or fistulas could occur. Other than that, apply the usual rules of safe sex by not inserting anything that has been in the anus into the vagina without washing or changing condoms.

* My girlfriend and I are looking into the possibility of having an open relationship. This is scary territory for both of us but we think we might like to try it. What are the rules or what are your recommendations?

In buying real estate the popular belief is “location, location, location.” In opening a relationship to others I’d modify that to “locution, locution, locution”! In other words, lots of communication. Discuss in detail your fantasies and fears. Do you want to know about your partner’s others, at all or in how much detail? Do you want to disclose details or keep them private? Many rules that the two of you devise will come up after the fact because someone has been upset or confronted with unexpected feelings. Be prepared for it all and keep on talking. There are several good books on the topic that might help you in areas of discussion from the original 1980’s Open Marriage to the recent Polyamory: Roadmaps for the Clueless and Hopeful, Open: Love,Sex & Life in an Open Marriage and Opening Up: A Guide to Creating and Sustaining Open Relationships.

* I know there are growers and showers when it comes to penises, the ones that start out small and thin and plump up much bigger and those that just got a bit thicker. I also know that all the ways you’re supposed to be able to tell how big a guy’s dick is by his foot size or ring finger length. I want to know if there is any way to tell if a woman’s vagina is tight or loose, big or small.

Trying it on in the privacy of your (or her) home several times is the best way to judge. The same woman at the same time of the month might feel tighter or looser, dryer or wetter depending on her state of arousal and position for intercourse. How many children she has had, how old she, her weight, her menstrual cycle, all affect vaginal size but how tall or short she is, big boned or tiny, not so much.

* I’m a 48 year old graphic artist. Don’t make a lot of money. Not too tall. I don’t drink nor drive a car. I’m told all of these things are strikes against me in finding a wife or sweetheart. I’m fairly particular in the type of woman I like and I really would like to start a family some day. Am I being unrealistic? Am I asking for too much?

I really don’t know. You didn’t balance the equation by telling me what you do have or are that a woman might find attractive and if they are qualities that are immediately apparent. Requiring a fertile woman with whom to make a baby is already limiting your options. Your question is best asked of women who know you and (one hopes) like you. They can best tell you what you might do to increase your chances.