My most recent dalliance with a fuckboy happened in the Summer of 2019. It was a very short-lived romance but it had quite a significant impact on me for a plethora of reasons. Firstly, it was the first time in many years that I’ve allowed myself to be duped by the male species-I’m normally far more wary when it comes to penis bearers. Secondly, I permitted myself to inadvertently be made a complete fool of and thirdly (more importantly than the former two) I had my first man-made orgasm, a feat of nature I thought unavailable to me.
The tale starts in July when my friends and I attended a Regatta. Attired in our best and lubricated to the eyeballs with Helen’s homemade Frosé (frozen rosé with strawberries that gets you absolutely shit-faced) we stumbled across grassy hillocks in our wedged platforms, rubbing shoulders with Berkshire’s wealthiest and most fabulous. We were absolutely not there for the rowing, that much I can allow.
Some hours into the day and copious amounts of alcohol later, our beautiful friend, Selena, began conversing with a boy she had gone to school with, Ross. By all accounts Ross had been a total prick to her at school when he was a cool kid and she was not. But now Selena was tall, glamorous and stunning with long, dark-blonde hair and a personality to match her beauty, Ross found himself apologising for being a total pale, ginger twat to her in their middle school days – at one point he even got down on one lily-white knee to display the deep nature of his remorse. It was like something from a 90s rom-com; the geek at school turned glamazonian queen and the popular knob-head being made to eat his words from a position of total submission.
In the staple post-party de-brief during the enebriated taxi journey home us girls were discussing the events of the night and this small section of the day came up in conversation. Helen was telling Selena that she was wrong to harbour her deep-rooted feelings of contempt for Ross, that he was now a self-made success story with a great business, good morals and a sensible head on his shoulders. I hadn’t known Ross when we were all at school so I couldn’t formulate an opinion either way, but the boy I had encountered seemed friendly, polite and eye-catchingly tall. He wasn’t amazingly good-looking but there was an alluring charisma about him. I tried to persuade Selena that he seemed like a great catch based on the information Helen was providing. Selena, however, did not want to know. ‘Once an arsehole, always an arsehole!’ was her mantra…oh how right she was!
But Helen’s words had resonated with me. I’d been single for over three years, Wasteman Wes damaging me so badly I never wanted to entertain being with another man as long as I lived. You’d need a Davy lamp, a canary and a pick-axe to get into my vagina. Like the solitary bear, I had hidden myself away on my own to avoid being hurt again, concentrating on work to pay back the debt Wes had left me in and whittling myself out a life as a strong, independent Sass-Queen who most certainly did not want or need a man. That life was comfortable and I was happy and safe insisting a partner was the very last thing on my mind. Besides, I was far too busy with work to be thinking about a man. However, in trying to convince Selena about what a wonderful person Ross was, Helen was painting a picture of the exact man I would hypothetically write out on paper as everything I wanted.
A few days after the Regatta, Selena forwarded a screen-shot of a message Ross had sent to her into our group chat which she fully intended to ignore. I told her I thought she was crazy to ghost him and that the message was actually quite nice for a guy with a history of being a rotting fungal infection; it wasn’t a ground breaking initial approach but it was totally passable. I sent Helen a separate message saying pretty much the same thing; that I couldn’t fathom how or why Selena would pass up an opportunity with such a great sounding guy. Helen, fancying herself yet again as the Cupid of our group, put two and two together and laid out the foundations of her match making plans between Ross and I. Sure enough, a week later I got a delightful little message popping up on my screen from our guy, Ross.
Of course, he pretended he had remembered me from the Regatta which I knew to be totally untrue and of course, he was throwing complements down the gauntlet like Frisbees but I thought this was all very sweet. Still relatively guarded, I relied on my witty repartee to beguile him as we steadily sped on our collision course to date number one. He invited me to his place to watch Love Island which I would normally have said no to – everyone knows what happens on a first date if it is spent in the home environment – but my intuition told me this would be absolutely fine.
I was impressed to find that when I arrived at his he had picked up every single snack imaginable and each thing I had told him I liked was neatly arranged on the kitchen counter. The conversation flowed easily and he was ticking every box; he didn’t do drugs, he had his own money and it seemed like he was moving in the same direction as me. All we did was kiss and cuddle on his sofa and I realised how nice it could be to just be held while you watch a good film in the company of someone you liked. At six foot four he towered over me which I found really masculine and attractive…except for the part where he lifted me up to say goodbye and I split my ripped jeans from the knee right the way up to the waist line. Obviously I laughed this off in his company and then died 1000 deaths in my car on the journey home at the sheer mortification. Fucking ripped Topshop jeans.
For weeks Ross and I powered forward on a passage I began to feel sure was going somewhere positive. He was doing all the right things. Most strikingly surprising to me: I felt more comfortable being close to him and being touched by him than I had ever been with anyone else. I can’t explain why this was; he just made me feel at ease. I had always been conscious of not enjoying being touched by anyone, from the most innocent of hugs to the sexual contact of ex partners. But there was something I enjoyed about being near to Ross despite how early on things were between us. I think he reassured me, unconsciously, that I was not weird and frigid – that I could enjoy the touch of a man.
He was also saying things, making these pledges that had me completely hooked. He told me he was going to take me on a date to Nobu because I’d always wanted to go there but, of course, it was far too expensive for Wasteman Wes to take me to and nobody else had ever cared enough about me to know the places I’d want to be taken. He told me he would buy me an expensive pair of earrings I said I wanted to treat myself to; he told me we would go on a Christmas Day walk together because, as someone who is estranged from her family, Christmas can be both a lovely and depressing time for a voluntary orphan such as myself (Christmas was also a long way away which indicated he fully expected to still be speaking to me months down the line!). So you can see why, after only a few weeks I thought we were progressing to something really good.
But more than the pleasure I took in his touch and the fact I found hope in the things he was saying and doing, Ross really seemed to want to look after me. He expressed genuine concerns about the rough area I lived in, saying he wanted me to be safe and suggesting ways he might improve my security. There was always a risk that Wasteman Wes was going to rear his ugly head and this looked like it concerned Ross. He seemed to have my back and that, above all things, is the only thing I really want in a man. It comes from a place where independence has been thrust upon me and I just had to go with it or perish. The thought of someone looking out for me, being protective, carrying my heavy bags, sorting out my problems and making me feel safe was the biggest attraction. Ross was proving himself to be this wonderful person and I could feel any walls I had up being knocked down with ease. I let go of any cynicism and threw my sensibility and caution away…everything I knew about love-bombing or dream salesmen from the experiences of my friends was tucked firmly into bed-this guy wasn’t too good to be true, he was what I deserved after the pile of shit I’d been dealt.
The Nobu date was, without doubt, my favourite date of all time. We had pre-drinks in Hakkasan, Nobu served up the best things I’ve ever had in my mouth (pun intended) and then he took me to a casino afterwards, assuring me that he had never taken a date to the Casino before but that he loved being there with me. When the night came to an end we went back to his flat and the sex was unreal. Maybe I had gotten carried away with how great the night was, maybe he was just really good at sex or maybe I finally felt completely able to let myself go but for whatever the reason, I had my first ever human-induced orgasm. For most girls this is totally not a big deal, but for me with my history and at 30 years of age, I had genuinely believed for many years that I simply was not capable of being relaxed enough around any sexual partner to enjoy it so much I could come.
We were now seeing each other every couple of days and speaking all day, every day on the phone or by text. I was conscious that the summer was almost over and I would soon be going back to working flat-out. A residual habit of my time funding Wes’ lifestyle, I had two jobs and between September and June my second job meant I was busy every single evening and both days of the weekend – the call of money is just too attractive to me. For the majority of the year I don’t have time to see my friends and I certainly don’t have time to nourish the seedling of a relationship thus I wanted to give Ross as much time as I could spare so that when I inevitably got rammed with work, he would like me enough to put up with never seeing me. Plus, I just liked being around him and I hadn’t had that feeling since the early days with Wes. Was it such a crime to like maximising my time with this man? I didn’t think so – although in hindsight I made myself far too easily available to him.
We were also sleeping together every time I saw him-I wasn’t about to pass up the new found delight of multiple orgasms if it was offered. Helen and Kat had convinced me that if this was to continue, I needed to clarify with him whether I was the only person he was doing this with (we were all certain I was) and whether I should consider a more reliable form of contraception than the pull-out method (we were all certain I did). After all, the vagina is a really wonderful thing that asks very little of us women, just that we keep her nice and healthy – it was the least I could do for my flappy gal.
‘So…am I the only person you’re doing this with? Because I was thinking I need to look after myself and maybe think about going on the pill or something if we’re going to carry on doing this…’ I tried to sound as nonchalant about the whole thing as I possibly could; like I wasn’t going to rip his little blue eyeballs out and smear the juices all over his freckled face if I wasn’t the only one.
‘Yep – you’re the only one. I’ve got no reason to lie to you, I was seeing someone a while ago but…she’s a dick so…’ He left the statement hanging in the air but I had got what I came for. I casually lifted myself off of him as he lay beneath me and turned over for a little spoon before the post-coital slumber of a woman happy in the knowledge she’s on a one-way journey to the initial categorisation of ‘seeing someone.’ Surely this was the next step? I was mentally dialling my GP for an appointment to talk about the medical differences between Microgynon and Cerazette.
That weekend, both Ross and I were busy. He told me we would see each other Sunday evening which worked well for me. But Sunday came and I hadn’t heard from him which was…kind of weird…but maybe not. Like, he’d been out the night before. He was just hungover…maybe? So I shouldn’t send a text! That would look too needy. He’d definitely text me. Eventually.
16:15: But…he still hasn’t text me. And I’m meant to be seeing him in a bit…do I start getting ready or…? Maybe I’ll have a shower, shave the necessaries and by the time I get out of the shower he will definitely have text me.
17:05: Still no text…I’m too old to play games so I’ll just text him and see how his night went. Let’s be grown-ups here, girl!
17:40: OK I have turned on my ‘Last Seen’ on WhatsApp and I can see he’s been online today which pisses me off because his fingers are therefore definitely still attached to his big old hands so there’s no reason not to have text me. However, I’m being crazy so I’m turning my ‘Last Seen’ off and I’m going to wait it out.
17:55: Is he for fucking real? He’s been on WhatsApp, which means he’s seen my message, but he’s not text me back. Wanker. I’m putting my phone on charge-IN THE NEXT ROOM-and not checking it again. He can fuck off.
18:10: Ah he’s text me back! All is good with the world and I’m happy again. But he still made me wait ages for a message so he can sweat it out for a reply for a bit.
18:32: that’s long enough – because I’m actually only texting back so I can check whether I’m seeing him today or not. It’s totally fine if I’m not, totally fine (said in Ross Gellar’s squeaky ‘I’m so not fine’ voice), but I just need to know.
18:50: So he’s seen that message and still not text back but he is clearly messaging someone else off the hook! Right, even if he wants to see me now he can piss the fuck right off.
19:20: He’s been online loads but not replied to me…now I’m livid. I’ve put on my make up to distract myself from how wound up I’m getting – obviously I’m absolutely NOT seeing him, even if he asks now, but he still hasn’t even replied.
20:15: Half arsed message received saying he’s hungover and going back to bed…he reckons he hasn’t lifted his head off the pillow all day. In my gut I know this is total bollocks but at the same time it makes me feel better to think he’s dying of a hangover. Good. Prick. I hope he feels like his big head is being squeezed inside a vice! Also, I come to the realisation that I’ve turned into one of those girls who goes out of their way to check online statuses and ‘recently seen’ updates-who was I!?I’ll send a super chill message back saying I hope he feels better soon but he’s only getting one ‘X’ and he can just suck on that. Arsewipe. I pushed him and the fact he was potentially digits deep in someone else’s vulva to the back of my mind, put Pretty Woman on and resumed my evening.
The next day, I woke up with thrush. Why, Mother Nature? Why curse me vaginally with this cottage-cheese visiting when I’ve finally learnt how to enjoy sex? I needed to sort that out, STAT. A good-old pessary with the oral pill would knock that shit right out of me so I could get back to my orgasm education.
Overnight I’d had a word with myself and calmed down-he had been drunk and therefore hungover, he wasn’t my boyfriend and this was not a big deal, regardless. He had text me first thing to apologise for his poor performance and promised to make it up to me by taking me out that evening for dinner. Obviously, I couldn’t have sex with him while I was leaking mucus from my vagina but, do you know what, he deserved a little bit of abstinence after leaving me hanging all day Sunday.
The meal with Ross was…weird. Nothing I could put my finger on but he felt different. He was being shifty, looking around pensively giving off serious paranoia vibes. But then, I had to question, was I the paranoid one? Was I reading too much into his behaviour because of the previous day? It was more than likely, I had established I was clearly a psycho the day before – overthinking and reading too much into insignificant things because I liked this guy. So I put the strange feeling to the back of my mind and carried on with dinner.
When we got back to Ross’s he said he was tired and we could go watch a film in his bedroom. I wandered through while he finished up in the living room. I was mulling over how best to broach the subject of my thrushy situation with him. We’d been pretty open and honest to that point; did I come right out with it? Or did I let him get so far on the assumption he was crushing labs tonight just to leave him hanging as a punishment for last night? As I climbed into the bed, lost in my vaginal thoughts, I spotted a single false lash on the mirrored bedside table beside my head. It was extra long and I could see the little bud of black glue that would affix it to the owner’s natural lash. Unmistakable. Irrefutable. I tried to be reasonable. I tried not to freak out, I honestly did. I had a word with myself; maybe his cleaner, while cleaning around the bed, found it and put it on the bedside table? Because everyone knows fallen cheap eyelashes are recyclable, right!? Or perhaps when I climbed into the bed it puffed out from the fibres of the mattress like a feather on the breeze, the owner could have lost it months – years – ago! But that small, traitorous voice in my head told me he had been with someone else the day before. Ockham’s Razor – the most likely explanation is usually right.
No! Chill out – it’s one fucking eyelash, sister. Pull yourself together…but…wait…that girl’s deodorant can on the chest of drawers – it’s moved, hasn’t it? When I asked why he had a girls deodorant in his room weeks before he said he just picks up whatever deodorant he lays his hands on first in the shop. We had laughed about it, about how he smelled like a girl. And that was all good. Until the bottle suddenly moved position after being in the same place for the entire time I’d known him. Was that just a coincidence, an unfortunate quirk in timing that he had knocked that into a new place at the same time an eyelash had spontaneously worked its way onto his bedside table? But this guy was so nice, so great…and he was now saying he was going to take me to his Dad’s villa in Portugal. Why would he do that if he was sleeping with someone else? I lay back onto the pillow. Be casual, I told myself. Be cool, girl!
Ross joined me in the bedroom, laying his head between my legs and cuddling my left leg as he fell asleep. I could hear his rhythmic breathing as he journeyed deeper into the Land of Nod, but every now and again he’d wake and kiss me on my jeaned thigh before dozing off again. He was so lovely laying there like a…BIG FAT EYELASH SHAGGER. I glanced over at that arrogant lash, laying there rubbernecking at me on the mirrored furniture, reflecting back to me my own face, anxious and annoyed, with that fucking eyelash sitting smack-bang in the middle of the reflection. I needed to stop this – I was being ridiculous. It’s an eyelash, I told myself, get a grip on yourself. But…the deodorant can had moved too – there was no doubt in my mind!
Ross was actually sending my leg to sleep and I had to make a choice between staying there with a numb leg or moving slightly and getting the ticklies; his heavy ginger head laying on me sleeping off all that energy he’d clearly been exerting the day before pummelling puss. But look at him; peacefully resting there! How could this guy who assured me I was the only one he was doing all this with really have slept with someone else? There was no proof! Except…waaaaait just one damn minute…was that a long hair on his pillow!? Did one of my own hairs fall out when I got in the bed? It was dark so it could be mine. But my hair was shorter than that. Oh my God…the third nail in the coffin…and now that I thought about it, he hadn’t even tried to have sex with me. He’d gone straight to sleep using my crotch as a pillow. I was melting what looked like candle wax secretions from my vulva– I knew that…but he didn’t! Did I kick him in the head ‘accidentally-on-purpose’ and get the hell out of there or did I lay and let him continue to use my pelvic bone as a pillow? I made my exit. I needed to run this one past the girls – they’d slap some sense into me and tell me I was being silly, 100%.
Except they didn’t. The group chat agreed with me – something was amiss. They did nothing to curb my paranoia but we were all in agreement, to confront him would be stooping too low. I’d have to wait it out, see if an opportunity arose to ask the question.
As the next few days came I could actively feel myself checking out. I was still seeing him, though slightly less, and I was still speaking to him, though whole days would now pass with no contact. Where I was making effort with hair and make up and tan and ensemble before, I now didn’t care so much. I also hadn’t slept with him since the thrushy night but the thrush had long since vanished and my cervix was once again open for business. However, I was reluctant to let things go because this guy, just a week or so before, had been everything I could see myself with. It was all hot and heavy and definitely destined for big things…I couldn’t help but wonder if I was letting my guard and paranoia fuck this up and all he was guilty of was an unsociable hangover.
On a couple of occasions, I handed Ross the opportunity to let me down gently. He told me he had been busy – as I stared him right in his wide, blue eyes, looking for any hint of mistruth– he told me he wanted to carry on seeing and speaking to me, just things had been crazy. Then both times he leaned in and kissed me, and held my hand and it all felt so reassuring I was lulled once again into this false sense of security. I must admit though, this reassurance did coincide with me being able to do him a favour through my work so I now question whether he strung it out for the perks of private healthcare.
Finally, eventually, I found out the truth. Through friends of friends, Helen had been able to elicit enough information to confirm what my gut had been telling me all along. But the truth was more shocking than anything I could have made up in the corners of my mistrustful little mind:
Ross had, in fact, been sleeping with not one other girl (the ‘dick’ he had alluded to so many weeks before) but two girls. I was appalled to learn that in one week he had slept with all three of us. And the night he was strange at our meal? That wasn’t me being paranoid – one of the girls he was simultaneously sleeping with had friends in the same restaurant who were filming us throughout the meal. The girl he labelled ‘a dick’ saw the videos and was ringing him on loop; it now makes me smile to think how much he must have been shitting himself that she was going to turn up and cause a scene. Obviously I cringe more for myself sitting there being filmed without knowing – fucking tweenagers are such a nightmare.
I was really quite gutted to find all this out. Naturally, I was relieved, and I mentally made a note to never ignore my intuition again, but Ross had fooled me into liking him way more than I should have let myself and I felt like a total idiot. I was also really sad that he wasn’t the person I thought he was, and he would never reach the potential I thought he had. However, I knew he was someone I definitely wanted in my life, even if it was just as friends. I felt like he would have my back and look out for me and, as someone who had never had that before, I wanted to keep it. So I decided to send him a message which basically told him I wasn’t prepared to continue sleeping with him when I knew there were other girls on the scene, but keeping it nice and friendly enough that we could retain a friendship. I respected myself enough to know without question that I should be the only person a man I’m giving my time and energy to is sleeping with but I was also sensible enough to know that if he was already sleeping with two other girls alongside me, Ross was not someone I should be investing anything more than friendship in.
I crafted the message carefully, running it past friends to make sure the tone and desired effect were all right and then I hit the send button. I’m not sure what I expected back; I felt I’d been more than reasonable even wishing to retain a friendship with someone who had held my feelings in such little regard so I guess I was looking for a minimum of an apology and an admission before an agreement to salvage a friendship. What I got back really, truly surprised me…and I’m very rarely surprised by humanity.
He never text me back. No acknowledgement. No admission. No apology. Not even defensiveness. Total arial silence. It was unfathomable; we had gone from talking too much to having no connection at all. I had clearly overestimated how mature he was and done him a major disservice in making an assumption that he would at least message me back. As a grown woman, I couldn’t leave such a message unanswered but I was shocked to realise Ross was a boy disguised in the clothing of a successful man. I knew, instinctively, I would hear from him again at some point down the line but I could not believe he had just not bothered to respond to my ever-so-lovely-and-mature ‘thanks for the orgasms but you’re shagging other people so I’m sacking you off’ message.
Unbelievably, weeks later I got a ‘Hope you’ve had a lovely birthday. I miss you x’ message…at 21:30 on the evening of my almost-over birthday. I ignored the initial temptation to message him back with the middle finger emoji, deleted both the message and his number, and moved on.
Except that, a week to the day after this message was received, I fell down the stairs in a fluke accident while taking out my recycling. In a glamorous turn of events, I actually fell directly onto the recycling bag which simultaneously broke my fall and eight of my ribs – four of which were already weakened by Wasteman Wes. I also had a corker of a black eye from where I tried to salvage the bag of plastic from spilling during my tumble and inadvertently hit myself in the eye socket. This turned deepest purple-yellow within hours of the fall. In the weeks that followed I was feeling really, really sorry for myself. I could barely do a thing and, living on my own, that poses some serious problems. Friends and colleagues suspected Wasteman Wes was involved in the injury because of my black eye which made me feel embarrassed and I hid myself away, secretive as an oyster. If the pain from the first break was agonising, it was nothing compared to this second blow and I lay there in my solitude and pain night after night, thinking about how things might be if I had someone to care about me, or if I were still seeing Ross. He’d maybe have come over and looked after me, he would possibly care when I had no family around and all my friends were understandably busy with their own lives. In a rare, weak moment following an evening drowning the ache in my ribs with some Valpolicella, which was obviously ill-advised while nursing a significant injury caused by sheer clumsiness, I felt sad for my poor broken self and I sent Ross a ‘I miss you too,’ message (obviously I had kept his number written down when I deleted it for just such a stupid occasion). I regret it utterly and did from the moment I hit send. Not just because he ignored me once again but because I found out he had immediately screenshotted that message and sent it into his family group chat for a good laugh and to show off about the fact that, even though I had kicked his top-shagger arse to the curb, he’d somehow managed to claw back a way to save face.
So, in summary, Ross was a short-lived, bitter sweet summer romance that never really was. He sold me a dream for those few weeks, and I bought it. He totally fooled me into thinking there was someone out there who genuinely would have my back and he disappointed me more than any other man because I simply didn’t expect it. However, Ross was a really positive experience for a multitude of reasons. The first is that I learned to always listen to my gut – it indicated to me every moment where I needed to have my guard up but I let cheap words override that. The second is that I learned not to put my cynicism away so easily until someone has proved themselves to me and to be unavailable even when I know future availability will be limited. The third, final and best blessing of my romance with Ross – I can come through sex…and when I decide to do it again I’ll be safe in the knowledge that not only can I show a man a really good time, but I can use him to bring me to climax for my own enjoyment. So thanks, Ross, hun – for that wonderful, wonderful gift.