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.)
(Have a question of your own? Please consult this page to see if I’ve answered it in a previous column, and if not just click here to ask me via email.)

Well done!
I hope she sees this because your answer is perfect. I just want to underscore a couple points from my own experience –
– For me, sex hurt the first time. And the second, and the third … actually, sex just hurt for a long time. Why did I keep doing it? Well, after I did it the first time, I had this inexplicable primal urge for it that I couldn’t explain, so I just worked through the pain. If your experience happens to be similar, understand that you’re not the only one and it doesn’t mean there’s anything wrong with you.
– Attention is indeed intoxicating, especially when you spent years being lonely and aching for companionship. Enjoy the attention, allow it to meet your emotional needs, but don’t make more of it than it is. The best way to do this is to find other sources of attention and companionship; that way this one guy won’t feel like live-saving rain during a drought and you’ll be better equipped to evaluate your relationship with him honestly. I went through a period where I went out with EVERY guy that asked (even if I didn’t really like him) because my mind plus the lonely years said this is the last chance you will ever get for love so if you don’t take it NOW you will be lonely forever and it will be all your fault for rejecting love.(*) But you don’t have to be that way – meet people, go on dates, take notes about what YOU want, and then be as picky as you want. (Spoiler alert: 15 years later, I did end up married with children and I’m ridiculously happy I found the right guy.)
– Being married and having children puts a person (but particularly women) in a very vulnerable position. I was in that position, thousands of miles away from family, when my ex-husband decided that the baby and I didn’t need a place to live. In the winter. In Fairbanks, AK. What saved me was a combination of social services, adrenaline, and finishing college so I could start a career and support myself and the kids. Yes I worked my tail off but I was so, so lucky – I cannot emphasize this enough. It could have gone so much worse for me, as it has gone so much worse for far, far too many women. Do not risk your life by puting yourself in that position. You are too precious and too valuable for that. No amount of love and attention is worth it.
In closing, follow Maggie’s advice – it’s spot-on.
(*) In case you can’t tell, my brain can be kindofa jerk sometimes.
Think this is a typical case of “girl from impoverished country meets boy from a wealthy one.”
I wouldn’t ding on her too much for falling for this guy – given where she probably comes from and the hard life she’s probably led. I have met many girls like her who have married American servicemen they met overseas. Female love tends to be less closely tied to penis size than it is to “girth” of a dude’s wallet. Having an American (or in this case – Canadian) husband is a great asset to the wife and her entire family as well. It doesn’t even have to be a perfect marriage either – she probably already has low expectations for any man she meets.
Dick pics. Yeah – I met that girl. You know, the one girl in the world that BEGS you for a dick pick. Met her in the bar while I was working about a year ago.
She came up to me and was thumbing through her cellphone photo album trying to find me a nude selfie she shot of herself. I figured, “well, I’m not doing anything right now so this is a worthwhile use of my time.” LOL. Hey, you gotta be NICE to customers, right?
She had a major problem in finding her nude selfie … because of all the DICK PICS she had to sift through. I’m like … “What in the FUCK, girl? Did all these guys send these to you or did you download them off the net?” She’s like … “Oh no, guys send them – and I collect them – WOULD YOU PLEASE SEND ME ONE OF YOURS?”
LOL … “Nope”.
Her nude selfie, when she found it – WAS FUCKING AWESOME though!
“Female love tends to be less closely tied to penis size than it is to “girth” of a dude’s wallet.”
That’s great, hope you don’t mind if I use it sometime!
Solid answer to a person vulnerable to being used. I hope she takes heed of your words.
It’s exceptionally rare for a woman to find any special pleasure from receiving a dick pic, except as part of foreplay with a man she knows well and intends to have sex with. Curiosity, maybe for her, but this man is interested in only his own pleasure. He should find a woman who shops for men based on size, and she should find a man who isn’t trying to sell himslef by impressing with his size.
The virgin I know who is older than this woman? Still a virgin and about to turn 45. And that’s OK. She knows what works for her better than I do. And me? Between Laura and my own pervy imagination, I do just fine.