Sometimes guys ask me for my advice. Stop laughing at the back.

Although I’m as incompetent as the next person, feeling my way through sex and relationships like a horny blindfolded girl groping for the light switch, people occasionally email me and ask for help with their problems. The following predicament concerns a guy who wants to make his fantasy come true, and it struck me that there’s a theme which runs through most emails I get about this subject: whether it’s throatfucking, swinging, threesomes, or something beautifully sweet and simple like the one below, quite a few ‘how do I achieve my sexual fantasy?’ emails share a common theme. So, to try and kill a few extra birds with my stone of shoddy advice, I asked the guy for his permission to post the question, and my response.

Please chip in your own advice in the comments – I’m not an expert, and I am frequently wrong about things.

The problem: how do I make my sexual fantasy come true?

I am obsessed with girls and especially the female body. I absolutely love the female body and how it reacts to sexual stimulation.

I am 19, male and I haven’t had actual sex yet. I have been masturbating and fantasizing for several years now and really want to finally have some sexual action with a hot/cute girl. I don’t want full sex with her but I really really want to make out and pleasure her. I am very curious about how it feels for a girl and how close sexual stimulation feels with her body and words.

So as you can tell I am absolutely mullered by the fantasy of making out with and pleasuring a hot/cute girl who’s OK with not having actual sex.

The thing is: I live in a Christian community and I’m not really attractive or athletic and I don’t have a girl friend. I’m extremely introverted and so I think it’ll be while I’m in my mid or later 20s when I ‘d find a girl friend.

And my parents would wonder what I’d be doing (and against it) if I just went into town to hook up with a girl for a bit. I can’t be openly driving to people’s houses or strip clubs or whatever with my parent’s car.

So I think the best bet would be that I take a walk and have the girl pick me up while I’m doing that and us make out in the car or something like that.

But so far I haven’t found a legitimate website that I can find actual local girls to hook up with for free. I live [location redacted – somewhere rural in the US]. Do you know of any legit and free sites that will allow me to possibly find a girl willing to do this with me?

So far all I have found are scam sites and ones that I need to dumb paid membership for. And for me, I really can’t afford that risk atm. I’ve tried CraigsList but that’s all a bunch of scams..

Oh what am I to do?!?

Answer:

The good news (OK, the fantastic news) here is that what you want isn’t in any way unusual. There are lots of people who want to make out – they want the awesome touching, horny kissing, etc, but not necessarily the sex. Perhaps because they’re not ready for sex, or just because they don’t enjoy sex as much as the other parts. But I assure you, there are many people who want this. So you’re in a good position.

However, there’s a really big problem with your exact situation, and that is that you seem to want a very specific thing, and you don’t seem willing to do anything even vaguely out of your comfort zone in order to achieve it: you can’t drive anywhere, you won’t pay money, you won’t use free sites because of scams, you won’t speak to women because you’re shy. In short: your easily achievable fantasy becomes almost impossible because you need it to land directly in your lap with very little compromise or effort on your part.

If I knew what the effortless solution to your problem was, I would have bottled it, sold it, and be typing this on a gold plated laptop right now.

I don’t blame you at all – this is not my way of calling you a wanker. It seems that you are worried about so many things that all seem insurmountable. Instead of trying to overcome one, or all of these issues, you have made them conditions of your fantasy and I think that’s why you’re struggling to achieve what you want.

To sum it up, your ideal fantasy is one in which you kiss, touch, and generally have sexy fun with a girl without having penetrative sex. Big tick in that box: loads of people like doing it, so your pool of potential partners is huge. But you don’t want to have to speak to a woman much, or develop a relationship with her, because you’re shy (totally understandable, by the way: some of the guys I’ve been hottest for have been shy). You don’t want to pay for membership of a dating site (and who does? They’re pricey!). You can’t use a free site because you might end up getting scammed. You don’t want to have to drive and pick her up in case your parents find out (again, understandable, if you think that the consequences of that would be horrible for you). Basically you want all of your ideal conditions met. And that makes giving you advice almost impossible, because any advice I give would mean compromising on one of your conditions.

So, bearing that in mind, here are three advice options:

• Keep trying with free sites (I am a big fan of OKCupid, and I think you have that in the States, but if anyone else has suggestions please leave them in the comments!), and trying to weed out possible scammers wherever possible. Accept, though, that you will meet people on it who are either scamming you, who want something slightly different, who might want a relationship before makeouts, or who don’t have their own car: that’s just how humans work, and it’s impossible to recommend a site which can deliver you someone guaranteed to fill every aspect of your fantasy.
• Go pro. When I read the first half of your email it occurred to me that if you really want this specific thing, but without having to develop a relationship, then speaking to a sex worker could be ideal. Find someone in your area (on Twitter I see adultwork mentioned often by sex workers, so I’d recommend heading there first, unless any sex workers have better suggestions that they can leave in the comments, pretty please!) who you can have this experience with. This involves compromising on your ‘free’ rule, but it’s one of the simplest ways to guarantee that you can have what you’re looking for.
• If you don’t like the above ideas, then the only thing I can recommend is to compromise on the ‘shy’. Which I know I know I know is hard to do. Speak to women, and try to develop a relationship with one who would like to do this with you. You don’t necessarily have to be boyfriend and girlfriend if that’s tricky for you, it might just be a girl you get along well with who also wants to have a go at making out and touching: it’s fine. I know this is scary if you’re shy: incredibly so. But it won’t get any easier if you never do it, and if you don’t manage to find a girl who’s willing to do this with you, you may still have met some nice people and had fun with them.

And that’s it, I’m afraid: I don’t have any magic bullets. As I said originally, I’ve been asked similar questions quite a few times, and I struggle to give advice because often I think what the guy wants is for his fantasy to just happen. You’re luckier than others in that usually their fantasies are things that are a bit more niche or kinky, so their original pool of potential partners is limited by the fact that only a small slice of the population would be up for the act itself. But either way I’ve seen lots of variations of “I need X but I have to get it without doing A, B or C”. As with you, they’re all usually legitimate concerns, and understandable problems. The trouble is, when you add them all up, the only way the fantasy is actually going to happen is if a passing woman just happens to fancy making out with the stranger she’s driving past, and has the confidence to shout out of her car window and ask for it.

So, to summarise, my advice would be that you need to pick one of your conditions and either compromise on it or make some effort to overcome it, or you need to cross your fingers and hope really hard that the very unlikely happens, and do a hell of a lot of wanking in the meantime.

Oh, and worry about the car situation when you get to it.

“Tribute wank” is a term that I was unfamiliar with until this week, making me think I should spend less time wanking myself and more time conversing with other humans.

A tribute wank is, from what I gather, a wank you have about someone in particular, which you send them evidence of later. It could be anything from phoning them to say “hey, I cracked a quality one off over you yesterday when I was thinking about the hot sex we had last week” to sending them an actual physical photograph covered in your own jizz.

The hotness

I once received a fantastic video from a guy which had – as most of my favourite videos do – his cock in it. He stroked vigorously for the requisite few minutes, just enough for me to start salivating a bit, then came nice and hard all over his hand. So far, so traditionally excellent.

But in the background of the video he had his laptop open, with a picture of me comfortably full-screened. He’d used one of the pictures on this blog, downloaded it, opened it in a new window then – most flattering of all – focused on it for the duration of an entire wank.

The not-so-hotness

So having established that I think tribute wanks can be really hot, I’m going to backpedal madly and tell you to think very very carefully before sending your delightful post-wank picture/video/text. Apart from the obvious problems (once it’s out there, it’s out there), you need to be really sure, before you hit the ‘send’ button, that the person at the other end will be pleased to receive it.

Even as a lover of hot pictures and homemade porn, there are certain things that will turn me off quicker than if you’d taped a picture of Jeremy Clarkson to your bellend. For instance, if you demand an immediate response, you might as well put your camera away and just chuck a bucket of cold water over my privates. Equally if you decide to send me something when I’m pissed off with you, I’m unlikely to leap joyously from my seat and shout “my God, what a touching kiss-and-make-up gesture, I must hump this man into a sticky mess immediately.”

So, if you’re tribute wanking over your partner, and you know they’d be keen to see the evidence, my advice would be to time it carefully: try not to send it when they’re in the middle of a conference call, or angry at you because yet again you’ve failed to do the washing up.

The downright awful

This might sound shocking, but many people just don’t want to be sent homemade pornography at any time. They’d rather you kept your dick/tits/arse/that cool trick you’ve just learned with a Hitachi magic wand out of their inbox.

I’d hazard a guess, based mainly on how many cock pictures I (sex blogger but basically a nobody) receive versus the number of cock pictures my friends (nobodies who don’t also happen to run a sex blog) get, that most of the cock pictures flying around the internet are unsolicited. That is to say, they are not sent between two consenting adults, but sent from one consenting adult to another adult they are really hoping will enjoy the picture.

I fully understand why you might find it hot to send your naked self to a stranger, but do you see the problem here? You can hope, you can wish, you can dream, but if you send any part of your anatomy to someone you don’t know, who has never asked you to send anything, you can’t guarantee that they want it.

So here lies my problem with tribute wanks: while some receivers find them amazing and sexy, I know a lot of people who would find them not just undesirable but awkward, horrible and downright terrifying. Others, of course, might enjoy receiving one from a person they really fancied, but wouldn’t extend this enthusiasm to everyone on their contacts list.

We receive spam all the time, and of course it’s easy to hit ‘delete’ or ‘unsubscribe’. But this is different. It’s not the equivalent of a delivery driver shoving some useless local pizza deals into your mailbox, it’s more akin to … well … a photo of an anonymous nob in your mailbox.

So, in conclusion, tribute wanks are like any other sexual act under the sun: some people like it, some people don’t. If you want to do it you need to make sure that the person you’re sending it to is not just ready but eager to receive it.

Note: I used to ask guys to send me pictures. It was amazing and lovely. I’ve since realised that was a bad plan, as I was inundated with pictures, many of which I didn’t have time to reply to and some I didn’t even have time to look at. I’m sorry. I have learned my lesson.

The vast, vast majority of the time, I am a loser. A lank-haired, jeans-wearing, slouching drunken loser. With a cider in my hand, a chip on my shoulder and a face like a bulldog chewing a whole hive of wasps.

I say this only to counter what’s coming next: right now I am hot.

I’m hot because I’ve had my hair cut – it swishes in that shiny way that some people achieve daily, but for me comes round only twice a year when I go for my biannual hack. I’m hot because I’ve spent the last week doing more exercise than I normally would and – although there’s no immediate visual difference – I feel stronger and livelier and readier to bounce around like a puppy on MDMA. I’m hot because I’m wearing knickers that cup my arse comfortably, and because I’ve been doing DIY in hot pants and getting dirty and sweaty and wet.

We need to deal with your high self-esteem issues

I’m British, of course, so writing the above paragraph was torture – it took me a good ten minutes to bash out just a few sentences without tagging something self-deprecating on to the end. I’ve been trained, through years of TV, magazines and friendly banter, that to talk about the things you actually like about yourself is a social crime. Like eating steak with the fish fork or passing a joint to the right.

Most of the time this makes sense. After all, we’d all be excruciating and insufferable if our conversations started not with “how are you?” but “how hot am I!?” We’d barely get beyond introductions before we were hurling into buckets at the appalling displays of self-love.

No, instead we must only ever speak of the bad stuff, while desperately hoping that other people notice the good. We’re trained to make the best of ourselves, so we spend hours primping and preening and picking out just the right kind of shoe only to shit on all that effort later on by replying “no, really, I look awful” when someone says something nice. It’s a reflex gesture, and one which makes sense most of the time. When the hard-earned compliments come, we bat them away with great force, because self-hate is a much more attractive quality than arrogance.

Start fancying yourself

I’ve got nothing wrong with light self-deprecation, and on an ordinary day I’m far more likely to make a tedious aside about my weight than to bounce into a room and shout “Look! Aren’t my tits brilliant?!”

But not today. Because, fuck it, I don’t always feel good. And on the rare occasions that I do, I want to start making the most of it. In fifty years time I’ll be yearning for the chance to wear this arse again, to sit in hot pants on a stepladder sugar-soaping walls and enjoying not just being me but looking like me too.

You should do it too – go on, do it. Fancy yourself a bit. There are bound to be bits of yourself that you’re not a fan of. But isn’t it bizarre that it’s these disliked bits that get all the attention? Hours in the gym toning a stomach that you hate. Days in front of the mirror shaping eyebrows or facial hair in some sort of damage limitation exercise. Weeks spent traipsing around shops that make clothes for people who always seem to be a different shape to you. All that time spent rectifying or changing or enhancing – how much time do you actually spend appreciating?

You don’t have to take pictures of yourself in sexy poses and pin them on the fridge, or give yourself cringeingly awkward motivational pep-talks about how beautiful you are. Just give yourself a bit of time to appreciate the things you fancy. The things that your partners will go primal for. Stand in front of a mirror if you like, touch yourself if you want to, put on or take off the clothes that make you feel best, and just revel in a bit of self-lust.

Because no one else can love you like you can.

Once upon a time I was sitting in a tiny greasy bar with a boy, when a rose seller came along. She had a basket full of dozens of roses, each one tied up nicely and ready to be hawked to the nearest soppy romantic.

I growled my customary ‘don’t disturb me in the pub’ growl. The boy looked interested.

Romantic acts

Romantic acts don’t have to be the obvious ones: diamond rings, flowers, breakfast in bed and the like. But these things do have a certain kind of charm, and if you want to impress someone, it might be easier to reach for a bunch of flowers than a deeply personal something-or-other that has the potential to backfire.

I have a deep and sincere admiration for people who perform romantic acts. Those who know exactly when to shower love, and in exactly what quantities, to make someone melt.

But it’s not easy. One person’s romantic gesture is another’s worst nightmare, and the success of the gesture in question all comes down to how well it’s received. I was reminded of this recently when a friend told me a story about a guy she knew: madly in love with one of his friends, he journeyed the two hours it took him by train to turn up at her house. Rather than knocking on the door and sobbing his undying love directly at her, he decided to be a bit more subtle. He knew she was a chess lover, so he left two chess pieces: a king and a queen, on her doorstep, along with a dozen red roses and a letter that explained how he felt.

“Aww,” said I “how romantic.”

“Fuck that,” said she “it’s creepy as all hell.”

The roses and the romance

I hate that this is the case, but it is, and I have no idea why. Romance is a fantastic thing, and I’m sure many of us would love to have more of it in our lives. But it seems like the main thing that makes a difference between a romantic act and an inappropriate one is something the romancer can’t always know: whether your crush actually fancies you.

If they do, you’re a hero. If they don’t, you’re a loser. And possibly a creepy one at that.

I’m going to tell you two different versions of the roses story now.

Version one:

The rose seller approaches me and the boy, and my heart is beating far too quickly, hoping against hope that this shy, nerdy first date doesn’t turn into a mush-riddled disaster. All I know about this guy is his name, his occupation, and a story he’s told me about how his sister once pushed him off a swing. I don’t know him well enough to anticipate whether he’s cheesy enough to think the ‘rose for a pound on a first date’ gambit is a good idea.

He does.

Red-faced, I accept the rose. Later that evening we part, and his post-date text seems unnecessarily gushing. We never see each other again.

Version 2:

The boy grins at the rose seller, and I whisper to him “seriously, dickhead, don’t buy me a rose. I’d only have to carry it home.” He squeezes my leg under the table, looking slyly at me in the way he knows makes me want to lick him. For the last two, three, four years I’ve alternately mocked and raged at him for his lack of romance, his lack of spontaneity.

“How much for a rose?” he asks the lady with the basket. I’m looking away now, too embarrassed to make eye contact and show that, secretly, I actually really want a bloody rose, even if it’s drooping slightly and will end up getting left on the bus. She tells him how much they cost, and there’s a long silence. Ages. Aeons. Millennia pass while I stare at the rings of liquid on the bar and fiddle with the plastic twizzly gin and tonic stick and just wish he’d get on and tell her ‘no’ so that we don’t have to eke out the embarrassment.

Years, or perhaps five seconds, later, he speaks.

“I’ll take the lot.”

And he hands over note after note after note from a wallet that’s rarely opened unless it needs to be. And I walk home arm in arm with my boyfriend of many years, drowning in roses and love.

There’s no right way to do romance

Arguing with my friend over the chess incident made me sad for the boy who’d tried so hard. For his unrequited love and his inability to read the girl’s reaction. Assuming they were both in earnest, no one did anything wrong here: it’s just a misjudged gesture and a mutual tragedy. But from my friend’s point of view, it’s a stupid guy making a desperate play for a girl who’ll never want him.

As she put so succinctly: the difference between creepy and romantic often just comes down to whether they actually fancy you.

I don’t think I want this to be true.