*New* Dear Lily: I’m writing to you about my, um, downstairs compadre. I’m not exactly packing the heat in that department which has sometimes caused me great embarrassment, especially on things like sports days at school when we all had to shower in the locker rooms. I got called all kinds of names: noodle dick for example, and once someone even gave me a cheerio to have sex with. Anyway, now I’m nineteen and have a girlfriend and of course I’m worried about having sex for the first time with her. Do women really care about the size of a penis? – toothpick dick
Dear dick: First of all, we girls appreciate humour in a man above most other things. I suppose in your case, a sense of humour may be especially useful. Humour rates just below filthy rich, but well above over/undersize dongers, so you can assume that the size or the lack thereof is not that important. I must say that the problem of penis size is very much, in my opinion, a male generated one with men’s belief that sex is only about genitals, so bigger must be better. It isn’t. Focus on everything else – having fun, exploring sensuality and intimacy. Most girls will not care much about the size of that cute little appendage when it’s called to action if you follow this advice.
*New* Dear Lily: I’m single again after a marriage that didn’t work out. I’ve had a few girlfriends since and now spend a lot of time with a girl, who is my best friend, who now wants to have sex – with a promise of no strings attached. I don’t love her that way but I like our friendship. What to do? – Paul (but not the Saint)
Dear Paul: Do you know how many millions of men who, when confronted with sex with no strings attached, would not be writing to me about it. They’d be into the shower, calling Interflora, stopping by the chemist and beating a path to her door with a grin from ear to ear. But since you did write, here’s some advice: Women try to persuade men into bed by saying that sex is just nothing, and it will simply be a pleasurable but meaningless experience. We are lying through our teeth. It’s men who want the meaningless experience, women want a deeper relationship so be prepared for a different best friend if you agree.
Dear Lily: I think I am falling in love with a sex worker. I have spent a lot of time with her and we have shared very intimate moments. I have asked her on a date outside the brothel, but she has yet to accept, telling me she’s very busy. What does this mean? – Confused Lover
Dear Confused: She’s weighing up a few things. She’s probably earning as much as the Prime Minister and thinks you’re going to ask her to give it up. For you, love, and a living wage. Do the maths.
*New* Dear Lily. I have cheated on my wife but realised it was a mistake and ended it. Now I feel very guilty whenever I see her. Should I tell her the truth? – Torn
Dear Torn: From your email, I can easily tell you love her and want to stay together. The only question for you is how would she feel if you told her. I can tell you a few possibilities: she’ll feel she’s not good enough, why didn’t she know, will you do it again, are you still lying to her, was she better than her in bed, does she know her, to name a few. Does she deserve that anguish? Your guilt will fade, but trust never returns. So keep quiet.
*New* Dear Lily Yang: It’s Boris, and I just got a great new job as the new Winston Churchill; Eton, Oxford and looking like Donald Trump is definitely the passport to power these days. But I have a problem. All of my so-called, upper class friends are in relationships except me, or gay. How can I stop feeling so alone and jealous of them for having someone who cares about them like that?
Dear Boris: Like most, I was bemused when you got the keys to Number 10, just like the old days of Empire! It says as much for the English, as for their US cousins, that they opted for another society-disrupting, whisky-drinking, upper-class twit as leader. To your credit though, you can at least string together a few compound words, albeit without thinking about them too much, even if they are in Latin. Don’t worry about feeling jealous and alone, you’ll soon find everyone wants to say something about you – the English haven’t had much to laugh about since the days of Monty Python. Just follow your American muse – a few mistresses, a few more porkies – and you’ll soon have Britain great again. New Churchill? Your Norwegian Blue parrot is not sleeping…
*New* Dear Lily: I’ve been married for now, it seems, forever and have become accustomed to my abject subjugation. But during a recent conversation/lecture, for the first time in almost 30 years, the most amazing thing happened. My wife told me I was right. I am naturally highly suspicious. Do you think she’s having an affair? – Baffled Bob
Dear Baffled: It is much more likely she was simply tired and didn’t wish to keep on instructing you. It’s hardly possible that you were suddenly “right” after all these years, so you need not worry about having to suddenly take responsibility for something in your relationship. I also doubt she’s having an affair, more likely having menopause, in which case you could expect several other hand-grenades being lobbed in your direction over the next few years. It would be worth your while to buy chocolate.
*New* Dear Lily: I hope you have time for my letter, you seem to have so many celebrities writing (I suppose even the rich and famous are screwed up too). Anyway, I made the mistake of sending a picture of my penis to my girlfriend – it’s huge – and she’s shown it to all her girlfriends. Now I’m getting calls from many of them to go to their places for sex, which I’ve been doing. My girlfriend thinks it’s hilarious and messages everyone afterwards. I’m sure most men would think this is heaven, but now I just feel like a sex object at a circus. What to do? – Have penis will travel
Dear Penis with legs: First of all, don’t send a picture to me, I already have enough for an exhibition at the National Gallery. Secondly, it’s safe to assume your girlfriend is not with you for the long haul and is simply enjoying the novelty of being with the biggest dick in town. Which is true whichever way you look at it. But you’re missing a business opportunity here; start charging money for sex, (perhaps a price per centimetre?) and photo-ops, double if they want to autograph it.
*New* Dear Lily: Me and “the guys” have been getting into a little trouble lately. As a matter of fact I just got myself arrested for enjoying a massage or ten. Thank goodness the leader of our rat-pack, the “pussy-grabber” himself, can just give me a pardon if the going gets tough. Yea, “The Don” – great name huh! – reckons in some parts of the world 14-year-old girls are already way past their prime, like in Nigeria and Burkina Faso, places he and I look to for our moral compass. Even Bill, Kevin and Randy Andy can’t work out what the fuss is about. We’re rich – what’s the harm? – Jeffrey Epstein
Dear Jeffrey: I regret summary justice will not come your way just yet, but I’m sure you’ll enjoy the anticipation – the fine lads at the State Penitentiary will no doubt want to remove your genitals with a blunt razor. I believe several have young daughters of their own. Best to keep a firm grip of the soap while in the shower after you become “Jeffrina”…
*New* Dear Lily: This is Kim K. I read your funny little etiquette book and thank you for writing that you thought my ass was more attractive than my face. Obviously, there is no comparison, that ass cost me a fortune. Even when I have a lot of make-up on, my face is not nearly as pretty, even though one my fans thinks so (go figure…). At least I’m not Khloe; there’s not a make-up artist in the world up to that job! You also compared my sex skit to Paris Hilton’s and said it was much better. This just goes to show your good judgment. Do you think I should make another porno flick?
Dear Kim: It never hurts to keep your best assets front and centre. It would be preferable to say, being a news anchor or lipstick model.
Oh, I didn’t say yours was better, I said that she looked scrawny. Judging you over her in porno talent would be like choosing to poke yourself in the left or right eye with a sharp stick.
* New* Dear Lily: As one of the most conspicuous fornicators and adulterers in Australia, who flaunts her lewd and depraving behaviour so brazenly to all God-fearing people, you will be sent to hell to burn in the fires of Hades for eternity. Now, as you can see, I’m a very non-judgmental person, but may the curse of Mary and her nine blind, illegitimate children chase you so far over the Hills of Damnation that the Lord himself can’t find you with a telescope. – Israel Folau
Dear Israel: This is not really a question, but I appreciate your warm, caring Christian concern for another human being. However, large, sweaty men fondling each other with their noses inserted in each other’s anuses, while they fight over a pig’s bladder, is not exactly my idea of the Promised Land, even if it’s yours. Smelling bums and chasing balls is only cute when my doggies do it. But let me not judge…