I am 27 years old and still a virgin; I don’t think I know much about sex, except in theory. I have a crush on a former Facebook friend’s boyfriend; he flirts with me sometimes, calling me “darling” and saying I’m “sexy” and “pretty”. We have not met in person yet, because he’s Canadian and I’m a Hindustani living in South Africa, but he recently sent me a picture of his penis and told me he’s about 19 cm long, and that scares me. Is sex painful the first time? I kind of dread ever having to have it in real life; I’d much rather just fantasize about it. However, I really love this boy; I dream about him all the time, and I wish he would bring me to Canada, marry me and give me a baby so we can live happily ever after. He’s younger than me (only 21) but very mature for his age; he really is my dream man! But I don’t know where I really stand with him; it seems like he only talks to me when he’s bored, and he punishes me by ignoring me when I make him upset. I’d really like to know what you think about online relationships; I value your opinion very much since you’re so sexually experienced.
I wish I could tell you that sex isn’t painful the first time, but it very often is and every factor you’ve mentioned – his size, his (much too young) age, your (advanced for a virgin) age, your inexperience and your fear – will tend to exacerbate that. So will the fact that he is NOT, despite what you think, mature for his age; punishing love-interests by ignoring them or just using them to alleviate boredom are NOT the marks of a mature or caring man, and frankly neither is sending out dick pics to women he isn’t actually involved with. I know that you won’t believe me when I tell you that you aren’t in love with him; you’re infatuated with him, which is a horse of a different color. You aren’t especially drawn to this man for his personality or self, but because he pays attention to you, and for a woman who hasn’t had that kind of attention often enough, it can be extremely intoxicating and judgment-eroding. I’m not saying relationships that start on the internet can’t work because I know some that have, but I am saying that such relationships involve many difficulties that you, inexperienced as you are, are unlikely to handle well. My suggestion is that you open yourself to meeting men locally in whatever way is acceptable in your culture; you still might fall in love too quickly and end up with a man who treats you badly, but if that happens you’ll at least be close to friends and family rather than stranded on another continent with a man you’re completely dependent upon. Ironically, you’re afraid of the part – the physical sex act – that is really no big deal, yet ready to rush pell-mell into the part – marriage and childbirth – which can really get you badly hurt or even killed. Sure, first-time sex can hurt; in fact, ten-thousandth time sex can hurt, and since my vagina is quite small I experience pain nearly every time I have sex with an unusually large or rough partner. Sometimes it’s even a lot of pain. But physical pain is transitory and, unless severe and chronic, doesn’t really have much effect on one’s life. Emotional pain, by contrast, can be both devastating and have long-lasting and far-reaching effects. I suggest you re-examine your priorities, try not to dwell on fear or simple physical pain, and instead think long and hard about the real and profound danger of severe emotional and spiritual (and sometimes physical) pain that accompanies a bad, hastily-made marriage to a poorly-chosen man.
(This question originally appeared in the form of a comment on a very old post, “All Shapes and Sizes”; some of you may find it interesting to compare the original with the edited version, and understand that this is typical of the way in which I prepare questions for publication. One difference: I usually leave out location, but since this lady already shared it in the comments it seemed pointless to leave it out here.)