To All The Boys I’ve Shagged Before

It’s funny how one comment from a dumbass troll can inspire an entire blog post, but that’s sometimes how life works. Put enough shit down, and roses will grow.

A few weeks ago Lucy was featured in The Metro newspaper. In response, a person calling themselves ‘Plato’s Ghost’ sent her a charming message calling her a ‘hoe’ and ‘just not marriage material’. Here it is in full for your amusement.

When she’d finished laughing, the main thing that struck Lucy (apart from the horrible spelling), was the idea that just because she writes about her failed dating attempts online, she must be a ‘tramp’ who’s ‘properly slept with 100 men’ (Lucy thinks he means ‘probably’, but he’s clearly an illiterate Neanderthal cunt, so let’s bear with him).

It’s funny how if a woman is open about enjoying sex, a fucktonne of people (mostly men, but also a fair few deeply internally misogynistic women, often from the US Bible Belt) assume that must mean she goes around fucking every man who comes within a 100-yard radius. Which of course could not be further from the truth in Lucy’s case. She actually wishes she HAD shagged 100 men, to be honest – at least now she wouldn’t be left feeling like she’d wasted her youth, and be desperately trying to find decent, non-creepy men to fuck to make up for lost time and experience all those naughty adventures that she’s never had the chance to try.

So no, Lucy has not slept with 100 men. Or anything like. Her number is… wait for it…


Just seventeen. Which if you count from when she lost her virginity at the age of 19 (she’s now 40, so that’s 21 years), is an average of 0.8 a year. Not many when you consider that Lucy’s been single for around 15 of those years, and that she’s been doing online and app dating on and off since she was 25.

Frankly, she’s disappointed. That’s an awful lot of Gobi desert dry spells and sexual frustration she needs to make up for now.

On the plus side, with a number that low, Lucy has no trouble remembering every single one of them. And here they are, in chronological order.

1/ The Peruvian barman, 1998

While the pretty girls at Lucy’s school are experimenting with smoking, drugs and boys, Lucy is, well, not. Chubby, clever, not sporty, with acne, terrible hair and no confidence, she manages to make it all the way to A-levels without having anything more than the occasional washing-machine snog with some random floppy-haired nerd on holiday. She’s never even seen a penis. By the time she leaves school, this deficiency has become an obsession. She needs to fix it, and fast.

Like so many nice middle-class kids, Lucy takes a year out to go travelling before university. For six months she volunteers in a primary school in Peru, spending her days teaching English to eager small children, and her evenings and weekends drinking cheap Peruvian beer and developing unrequited crushes on dark-haired, dark-eyed local heartthrobs. One of them is Juan, who serves at their local bar.

Juan shows not the slightest bit of interest in Lucy until one night, at a house party, when he suddenly starts coming onto her. Lucy’s under no illusion about his intentions, but she decides she doesn’t care. Here, finally, is the opportunity to get rid of the burden of her virginity. Not for her any thoughts of romance or rose petals, she just needs to break the seal (as it were). So she allows Juan to lead her into a spare room where, terrified of causing a mess on the hosts’ spare bed, she lies back and awkwardly lets him have his wicked way with her. It’s quick, perfunctory, entirely unromantic, and only moderately painful (fortunately because, luckily for Lucy, Juan is not exactly generously blessed in the trouser department).

The next day, Juan goes back to serving her drinks as if she’s just another one of his customers. Lucy’s a little sad, but not really surprised. And at least she’s not a virgin any more, which is really all that matters.

In spite of then going to university, where apparently everyone is at it like rabbits, Lucy somehow manages to not have sex again for another five years.

2/ The Hot German, 2003

After graduating Lucy moves to London, where she shares a flat with a couple of her university friends and throws the occasional house party. On one drunken night, her mate Gavin shows up with his German friend Hans in tow, and Lucy’s instantly smitten. Hans is the very epitome of Aryan perfection: tall, broad-shouldered, muscular, with piercing blue eyes and beach blond hair – he wouldn’t look out of place dressed in an SS uniform at the front of a Hitler rally.

Lucy spends the party getting drunk and trying to get his attention, to no avail. Eventually, people drift off, and a dozen or so of Lucy’s friends, including Gavin and Hans, crash out in various beds and on the floor. Aware that Hans is still awake, Lucy gets up and goes to the kitchen, pretending to get a glass of water, where, finally, he gets the message. He comes and joins her, kisses her, and then pushes her into the only unoccupied room in the flat: the bathroom. Hans tells her in no uncertain terms that this will only be a one-off thing, which Lucy, gagging to get her hands on that perfect body and have sex for only the second time in her life, agrees to, and they end up having a very fumbly, very unsatisfactory encounter on the cold, hard tiles of the bathroom floor with the light off before going back to bed.

In the days that follow Hans texts Lucy repeatedly, flirting even, and Lucy begins to hope that in spite of his protestations, he might actually be interested in her after all. So she invites him to her birthday party. He turns up with a girl in tow and stands by the bar with his tongue down her throat for most of the evening until Lucy’s housemate, in a fury, marches up to him and tells him to leave.

3/ The First Boyfriend, 2005

Lucy spots Nigel in the office. He works in a different department, but she sees him striding round with a small group of other hot guys like they own the place, and she immediately wants him (in spite of his stupid name). But with no way to get an introduction, what can she do?

Her chance comes at the Christmas party. She notices a girl she knows chatting to their group, so she goes over to say hello. That leads to an introduction, which leads to some flirting back and forth by email over the next few weeks, which eventually, after much frustrated hint-dropping by Lucy, finally leads to a date. Which goes so brilliantly that they end up snogging all the way home on the tube and Nigel misses his stop.

Lucy is completely, hopelessly smitten. The next three months are a whirlwind of dating and drinking and finally – finally! – getting her first orgasm. The first time they have sex it she’s terrified – what if he finds out she’d only done it twice in her whole life?! – but she manages to style it out based on what she’s seen on telly. Nigel meets her sister and her friends, and she hangs out with his. At long, long last, she’s finally someone’s girlfriend, and she fucking loves it.

And then, one Monday after work, completely out of the blue, he dumps her. Apparently that weekend he got drunk and snogged his friend Sally and realised he’s in love with her and not Lucy.

Nothing more ever happens between Sally and Nigel. Though he does go on to marry a girl who looks just like her.

4/ The Eager Puppy, 2006

After six months of crying and stalking Nigel round the office, Lucy makes her first foray into online dating. She joins where, after plenty of failed dates, she eventually meets Jason, a geeky but very handsome web designer. Jason is cute and funny and very keen on Lucy, which is rather refreshing after the bitter heartbreak she’s recently experienced – heartbreak that’s still so raw that, the first time she sleeps with him, Lucy cries.

But heartbreak isn’t the only reason for her tears. When she reaches down into Jason’s pants that first time, Lucy finds, well, not much. And when he fucks her, with all the panting, humping enthusiasm of a puppy, she has to restrain herself from asking ‘is it in yet?’, because she literally can’t feel anything. This might not be the end of the world, if Jason didn’t also refuse to get involved with oral sex – he won’t go down on Lucy, and he won’t (presumably out of self-consciousness about his size), let her go down on him.

Which leaves, well, not much. After three months Lucy finds Jason’s incessant perkiness has become tiresome, and she decides to let him go.

Happily Jason eventually learned what he was missing, and is now married with a toddler.

5/ The Chef, 2008

Another two years of enforced celibacy follow until Lucy joins Guardian Soulmates and meets Matt, a chef. Lucy falls for Matt on their first date when he gestures widely just as a waitress is passing and knocks her entire tray of drinks on the floor.

They go out for eight months, until Matt gets made redundant. He tells Lucy he really wants to take advantage of his new-found freedom to travel, so he takes a summer job as a chef in a Greek holiday resort. They agree that they’ll stay together, and maybe Lucy will go out and visit him, but just a week into his trip he changes his mind, flies home, dumps Lucy, and moves to Exeter.

As far as she knows, he’s now married and running a catering company.

6/ The Dutch Guy, 2009

In 2009 Lucy goes travelling again, this time to Colombia. There, in a hostel, she joins up with a lovely group of fellow travellers: a Kiwi couple, another British girl, and a skinny Dutch guy named Niels. Lucy doesn’t fancy Niels at first, but as they travel around together she begins to find his sparky energy attractive. The flirty chemistry is quite patently evident to the rest of their group, who tease them about it, until finally Niels kisses her in the hostel kitchen just seconds before the Kiwi couple walk in on them.

But sharing hostel dorms means sex is off the cards until their last night, when they go to stay with friends of Lucy’s in Bogota. Niels is on the sofa, and Lucy’s on an single airbed on the study floor, but as soon as everyone is asleep he sneaks in and joins her for a fuck that’s memorable only by how quick and pointless it is.

Lucy’s still friends with him on Facebook – he too is married and has just had twins.

7/ The Ex, 2009-2015

If you’ve been following along here, you’ll know a bit about this one. The guy who Lucy falls in love with, is with for nearly six years, thinks she’s going settle down with, until he dumps her and gets engaged to a girl from work five months later.

Sex with The Ex is fucking fantastic at the beginning. Like most newly-smitten couples they bang every chance they get. There’s one particularly memorable week away in the New Forest where they barely get out of bed, annoying the shit out of The Ex’s mates who are also there, and where Lucy, gagging to try something new, sneaks a condom into her pocket before a walk in the woods and persuades him to fuck her up against a tree – the first and only time she’s ever had sex outside.

But gradually, as with all relationships, the sex begins to tail off. The problem is The Ex is insecure about initiating sex – he has a strange hangup about the risk he might be forcing himself on Lucy – which means she almost always has to take the lead. Which does no good at all for Lucy’s sense of her own desirability. Soon they’re only doing it once a month, and only then because Lucy realises weeks have gone by and their relationship needs some maintenance. Their sex life dies, and the relationship soon follows suit.

8/ The Polo-Playing Lawyer, 2015

Lucy cries and doesn’t eat for six months, and then bravely launches herself back onto Guardian Soulmates. The first guy who seemes promising is Giles, a handsome and rather posh lawyer who plays polo and thinks rather highly of himself. On their second date he takes Lucy to a National Trust property and fingers her up against a tree in the grounds. Then there’s some sexting – another first for Lucy. But the one time they try to have actual sex he keeps losing his erection, and after that the whole thing fizzles out.

Lucy later discovers another single friend of hers has dated the same guy and had exactly the same problem.

9/ The Depressed Lawyer, 2015

Lucy goes back to Soulmates and meets another lawyer (she clearly has a thing for them). Clark is tall, rather overweight, two years younger than Lucy and very sweet. On their second date, before they’ve even kissed, he holds her hand across the table and earnestly tells her he thinks she’s beautiful and that he’d very much like to take her home and have sex with her. She doesn’t allow him to that night, but a few dates later she does, and finds him to be an enthusiastic and very skilled lover with a penis that’s deliciously in proportion to the rest of him. The sex they have is some of the best Lucy’s had – though TBF the competition isn’t exactly that fierce.

But Clark also has quite severe mental health issues, and Lucy’s far from being over The Ex, so neither of them is in the right place for a relationship. They end up becoming each other’s therapist, and call it a day after three months, They’re still friends.

10/ The Eco-Worrier, 2016

Jon is another Guardian Soulmates find, a sustainable energy developer, and a vegetarian. Freshly separated from his childhood sweetheart, he hasn’t ever had sex with anyone else, and hasn’t had sex at all for the last two years. This leads to him having serious performance anxiety, which Lucy patiently tolerates until, eventually, the problem passes.

This does not, sadly, unleash a new found energy for fucking in Jon. He still seems remarkably disinterested in jumping on Lucy, and after a while she begins to feel like a sex pest. Things come to a head after a couple of months when Jon takes Lucy to a festival and books them a yurt to sleep in. Lucy’s never had sex in a tent, and the yurt is desperately romantic: out in nature, with a squishy bed, and draped with fairy lights. Yet despite her naked and very active advances, Jon refuses to have sex with her, and when they get back to London, he dumps her.

Jon has now got over his divorce and has just had a baby with someone else from Soulmates.

11/ The Civil Servant, 2016

Lucy joins eHarmony, which she thinks is utterly terrible. She does, however, manage to get just one date out of it: Ryan, who works at the Foreign Office. He doesn’t tick all of Lucy’s boxes, but he’s fun and keeps asking her out, so she accepts. On their fifth date he takes her to Proms in the Park, where it rains solidly all day, and when the concert finishes he asks if he can come back to hers. Since he’s a good kisser, and she hasn’t had sex for several months, she accepts and they have a single night and morning of pretty decent banging. A few days later, Lucy goes off to Tanzania to climb Mount Kilimanjaro with her friend Sophie, and while she’s away Ryan ghosts her.

12/ The Hot Yoga Teacher, 2016

Possibly Lucy’s greatest pull to date, Andy is a fearsomely ripped and tanned yoga teacher whom she meets while actually on Mount Kilimanjaro. Having not washed for 8 days, with tangled hair and no make-up, it doesn’t even occur to Lucy to flirt with Andy, and they became passing acquaintances. At the end of the climb they say their goodbyes, and that would have been that had they not then run into each other a couple of days later on the flight to Zanzibar. Andy and his married mate James, and Lucy and Sophie, spend a hilarious night getting pissed and doing karaoke in Stonetown, before James and Andy come back to crash at the girls’ hotel. They end up staying for three days, during which Lucy and Andy are able to sneak off to fool around when the room is unoccupied, but neither of them have any condoms which leads to some extreme frustration on both sides. It’s still great fun though, and Andy even goes down on Lucy on a sun lounger under the stars, possibly the most romantic place she’s ever had an orgasm.

13/ The Radio Guy, 2017

Another woefully dry spell of several months follow, and Lucy begins to get depressed and frustrated. Here she is, pushing 40, in her sexual prime, single AF, and gagging for a shag. She needed to get laid a LOT, to make up for lost time, to have the experiences she missed out in her 20s, before her looks fade and she loses her sex appeal.

She meets Peter on Bumble. Almost immediately she knows he’s not boyfriend material, but when he leans in and kisses her halfway through the first date, and the kiss is go-ooood, she decides to give him a chance. Their second date involves a lot more extremely erotic snogging in a public park, which for Lucy, after more than six months of celibacy, is like opening the floodgates. She’s never been more horny or desperate for a shag, so rather than wait for Peter to take the lead, she takes a deep breath and nervously invites him over to hers on the third date.

It goes well. Lucy has her first ever fuck buddy, and they continue to shag each other throughout the summer until Lucy gets fed up with Peter being flaky and unreliable, and bins him.

Read all the posts about Peter here.

14/ Mr Monday, 2017

With her new-found confidence thanks to Peter, Lucy now needs another fuck buddy. She mentions this by text to her friend Adam, a guy whom she briefly dated but ended it with before they ever slept together, and he chivalrously offers to step into the role.

Adam drives all the way up from Southampton to see her, and turns out to have the most perfect body: tall, toned, tanned, with buttocks like the chiselled marble of a Greek statue and the most perfect penis Lucy’s ever laid eyes, hands or mouth on. Unfortunately, he seems to think having a perfect body excuses him from having to make any kind of actual effort in the bedroom, and after a couple of frustrating encounters Lucy decides he’s not worth the effort and calls the whole thing off.

Catch up on the whole Adam story here.

15/ The Geography Teacher, 2017-18

If you’ve been reading this blog for a while you’ll remember lovely Josh. Lucy meets him on Guardian Soulmates, and although he doesn’t immediately blow her away, there’s something about him that makes her want to see him again. Josh is rather eccentric, a bit of a loner, but very sweet and enthusiastic about pleasing Lucy in bed. They go on a handful of dates, but both agree they’re not a good long-term match, and when Lucy departs for her big Kenya adventure, they call it a day and agree to remain friends.

Which they have done. Lucy still sees Josh occasionally, but they haven’t had sex since she met Charlie.

Read all about Josh here.

16/ Mr No-Relationship, 2018

And so Lucy goes off to Kenya, where much to her surprise she meets Brad on her fourth day in the country. They have an outrageously brilliant first meeting, a whirlwind romance, and some pretty spectacular sex, before the fireworks turn into flames and come crashing back down.

Lucy spends the rest of her time in Kenya pining for Brad, and returns to London bruised and heartbroken.

Read the full story of Brad here.

17/ Mr Non-Monogamous, 2018-2019

And then, just a few weeks after she gets back from Kenya, Lucy goes to a house party and meets Charlie.

Lots has been written about Charlie, but if you missed it, Charlie is the smart, sparky, sarcastic, sexy lawyer who ticks every single one of Lucy’s boxes apart from the most important one of all: he’s not single. But it is an open relationship, so he’s free to pursue her, which he does with enthusiastic determination. And offered the promise of excellent, regular sex (hurrah!) with a man who sets her pulse quickening and her stomach flipping like pancakes on Shrove Tuesday, she’s powerless to resist.

They swiftly fall for one another, and much to her surprise Lucy finds herself in an actual relationship, her second longest after The Ex – which is wonderful but also heartbreaking. She loves spending time with Charlie, but the grotesque pain of knowing that he’s fucking other women is often too much to bear.  She regularly thinks about ending it, but somehow she can’t quite muster the courage, and before she knows it a year has passed and they are still together. How much longer she will continue to bear the heartache though, she simply doesn’t know. But she knows this can’t go on for ever. If she’s going to find The One, she needs to move on soon.


So that’s it. A hugely slutty and outrageous 17 men. And hopefully, with luck and a following wind, more to come. Lucy’s hoping the rest of 2019 will bring more great sex her way, so do stay tuned. Unless you’re a judgemental arsehole, in which case, and I mean this from the bottom of my heart, fuck off.

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  1. Lizzy
    29th June 2019 / 12:56 pm

    Hi Lucy, that guy clearly has some issues if he feels the need to troll you. I’ve read every single one of your posts and never have you come across as slutty, your history reads like pretty much every other single woman’s. It just comes down to the fact that life is so different for men and women, especially when it comes to dating. And they don’t have a clue that some of them (and as you say, some women), still have double standards. Bad us for liking, and doing, one of the most natural things in the world which is fun to enjoy! I’m sure you’ll let his comments roll of your back, but the opinions of someone who has the intelligence of pond scum really don’t matter. I love your posts and am rooting for you.

    There are some great guys out there and I’m really sure you’ll meet the one you’re meant to be with soon.

    I feel that I know you because I’ve followed you for so long (I know I don’t actually), and you don’t know me, and will probably think I don’t have a right to comment on the Charlie situation. But I just wanted to because sometimes I find myself feeling a bit sad when I read the posts about him. I have mixed emotions because I think if you are enjoying yourself then go for it, but if it ends up making you feel sad then it will only hurt you to carry on seeing him. If it makes you feel great then why stop it, but I get the sense that it hurts a lot every time he walks out the door. You probably know all of this though.

    I just saw a friend do the same with a guy and it just destroyed her in the end. I really feel like you deserve someone who will make you his main chick and his queen! X

    • Lucy
      29th June 2019 / 7:41 pm

      Hi Lizzy, no don’t worry he didn’t bother me in the slightest, I thought it was funny!
      Thanks for your concern – and don’t worry about commenting. I put myself out there, so if people engage that’s great! I’m sure you’ll understand that it’s not as simple as just ‘happy’ or ‘sad’ – there’s lots about the relationship that suits me really well, and parts that really don’t. It’s a compromise I’ve decided to make for now. I get some of my needs met, just not all. But that may well be better than none.

  2. Anonymous
    29th June 2019 / 2:13 pm

    Hey, I just wanted to share my experience with your blog. I was in a 3-year relationship when my girlfriend told me she wanted to see other people. I was really sad – I loved her – but there was a spark of excitement at the idea of dating new people, which I hadn’t really done much of. I googled around and found your blog, which ignited that spark. Since then I’ve been checking in every Saturday morning for the new adventure and it’s one of the highlights of my week. The genuineness, vulnerability, and humor you display are inspirational and I feel like reading your perspective has helped me understand how other people in the dating world think. I’ve been on a lot of dates now and have my own stories but still enjoy reading yours, and I hope you know you mean a lot to people like me 🙂

    • Lucy
      29th June 2019 / 7:39 pm

      Hi, thanks for your lovely comment I’m sorry your girlfriend said that – I’m curious to know if you have split up or just opened up your relationship and if so how you are finding that? I must say I’m astounded that reading my blog got you excited about dating – have you not been paying attention?! Dating is rubbish! But if it’s helped you then I’m delighted, and I wish you all the best in your search.

  3. 29th June 2019 / 2:51 pm

    :-)Wow Lucy
    Only 17???
    Am 37 and can promise you I have shagged almost 30 boys if NOT more.I lost count…
    Nice piece and thanks for sharing your stories

    • Lucy
      29th June 2019 / 7:37 pm

      Yes, ‘only’ 17. I’ve never been interested in casual sex, I don’t do one night stands, all I ever wanted was a boyfriend. But most guys just want to fuck. And I almost never meet guys I like who like me back. That’s how you can easily get to 40 with a number barely into double figures. I don’t regret it, but I would really like to find someone with whom I can make up for lost time before I lose my sex appeal.

  4. Rachel
    1st July 2019 / 5:04 pm

    Aryan perfection? Slightly problematic.

  5. Nick
    1st July 2019 / 8:03 pm

    I once posted my 31 songs on Google plus in a nod to Nick Hornby, but your honesty Lucy is inspiring.

    • Lucy
      5th July 2019 / 10:05 am

      Thanks Nick! Let’s just hope my mum never finds this, eh?!

      • Nick
        5th July 2019 / 7:13 pm

        Luckily Google shut down GooglePlus before my Mum had a chance to see my 31 songs post.
        Now your blog is a different matter 😉

  6. 2nd July 2019 / 6:45 am

    Hey Lucy,
    I just had to comment as I’m so cross that I’ve come to the end of the posts.
    I found your blog via Google stories a few weeks ago and have been addicted ever since, reading every chance I get. Now I’ll have to wait for weekly posts!! Roll on Saturday!!
    I’m not going to stick my oar in and give my opinion on your current Charlie situation – you just do you and don’t apologise for it!

    • Lucy
      5th July 2019 / 10:10 am

      Hi Kerry! Thanks for your lovely comment! Have you read EVERYTHING in just a few weeks?! WOW! That deserves some kind of award! There’s well over 200,000 words in here now!
      I’m so pleased you found me, hope you’ll stick around 🙂

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Names and some minor details have been changed to protect the innocent. And sometimes the guilty.
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