7/10/2014 (11:19am) 3 notes

single in a technological age

Before my recent venture into heartbreak, depression and an attempt at killing myself, I have never used a dating app.

In the past there was no necessity for one. I simply found a friend, went to a bar/coffee shop/supermarket/open bit of greenery and started talking to women. I may get a number, a kiss and even times sex right there and then. Not a boast but a fact (and a boast). This time however, the selection of friends to hit up a bar with is sparse not to mention the funds with which to enter said bar and enjoy a drink there if no woman of desire around.

Tinder. A friend suggested it. “I’ve fucked two girls on there.” He’s pig ugly and possesses the wit of a small horny virgin so if he was sleeping with women, I have a chance!

My first venture into online dating. As I found the app and started to download it, I swear I felt the clouds above me start to engulf the sky and loom ominously over me. If God were real this would be the moment his voice would boom out “Don’t do it! You meet women all the time, just sleep with them. You’re pathetic.” But as he doesn’t exist, the voice was mine. I had a point.

I really haven’t had a problem meeting and picking up women before. Then again I’ve never been properly engaged before. Once at 18 but that wasn’t by real choice. Back then I reacted by fucking everything and it wasn’t a healthy summer to go through for many reasons. Now here I am, a few weeks shy of my 31st birthday. Semi drunk, incredibly horny and nowhere to stick my penis.

I opened the app. Had a moment of pure horror as it asked me to log in via Facebook. Fucking Zuckerberg now wants to know who I’m trying to shag…even he’s judging me. How would this work? Would accepting this mean I am telling the world I am on tinder? Will mother cheeky know of this? All my friends? The women on Facebook I haven’t slept with, surely they’d see this and now think me pathetic. After a reassuring google told me that my Facebook account wouldn’t start leaking all my details out into the world, I went ahead safe in the assumption that my dalliance shall remain covert.

It took less than 30 minutes to get my first match. A 27 year old brunette called Anna. Cute, short, a shot in her bikini suggested that her body was ridiculous and she lives less than 2 miles from me or in terms of London transport, no distance at all. This is important. I’m on tinder because I’m horny, I also don’t have the funds to go crazy on public transport so if I can walk to her place and back, that’s a major plus. A thrifty online dater?! Form an orderly queue ladies! I start chatting “we matched, I’m saying “Hi” what brings you on tinder?” That was over 2 weeks ago, utter radio silence.

What is it Anna? What did I do wrong? Was my opening line boring? Did I offend by asking you to validate your online dating motives? Are you a boring fucker and the prospect of opening a dialogue seems so exciting it seems daunting? Are you a seasoned agoraphobe and worried that you’d have to leave the flat? Trust me, we don’t have to leave your flat! Anna slipped away, Katie was next.

Katie, a pretty 31 year old mixed race woman (not important but then for some reason I felt compelled to include this information? Likely says more about me on some level) again, a stunner and possibly the cutest smile I’ve seen. I thought I’d be a little different…

Hi, answer these…
Red or White wine?
Pasta or Salad?
Winter or Summer?
Shoes or Trainers?
Stay in or Go out?
Sex or Kissing?
Read the book or Watch the film?

She replied, giving answers - she got 5 correct if you’re wondering - we chatted for a bit on and off over the next few hours. That’s when I got her number and got in touch on whatsapp. It was at this point, casually flirting away, I took a look at her picture/avatar/mug shot that we all put on our profile. She looked totally different to the point where I didn’t recognise her. I sent a snap of myself saying “So unlike my pics I’ve not shaved in a few days (depression beard) are we a fan of beards?” Then I followed up with “I’m totally going to need to see yours, no dick pics please ;)” which I believe is the third time I’ve used a “wink” in a message to anyone other than the HMRC. Honestly, filing in a tax self assessment is easily the most fun I have finishing emails with kisses and calling the person reading it a cutie. With Katie however. Nothing. No reply to my beard or comment and certainly no return picture. Her profile went cold and her picture changed to an older, younger Katie within the minute. I like to think I caught her in her ruse, maybe she just isn’t a beard lover?

Two matches down, several others that didn’t reply or just stopped talking. Since when was getting laid such an ordeal? Is this what it’s been like for others all this time, is this the reason I was hated or envied by several men from the past?

Then we had Harriet. No friends in common, something that prods abject horror into me on that infernal site so it was a definite plus. Harriet, 28, very very pretty and only 3 km away…I’ve no idea how to switch back to miles from km…in her spiel she is doing an MSc, is still fairly new to London and most importantly she wrote “Here for some fun if you know what I mean :p” I’ve no idea if the tongue is better than the wink but the rest of it sounds promising. As I’m debating it all she writes to me. An hour later I have her number and arrange to meet her for a drink at 5, which is only an hour away. She arrives, is just as pretty and says in this seriously sexy, husky, posh voice “Thank fuck you look like your pictures.” A sentiment I am equally pleased at. We go for a drink, flirt, she’s incredibly timid for someone so forward. She asks “if you don’t mind can we watch the football a little later?” I’m not sure if she was reading my mind because as I was travelling to meet her, I was devastated when I realised I’d miss the game myself. We watch it, we drink more, she casually strokes my arm or finds any excuse to touch me in general. She eventually says “we’re not far from my place.” this I already knew and that’s why I suggested meeting where we were. We leave the pub, head back towards hers and as we’re walking, edging closer she says “I’m not going to kiss you mind *******!” WHAT? For someone so forward, who’s spent the entire night saying filthy things and being overtly suggestive (there are literally dozens of examples) she now tells me this?! I try to counter attack, “That’s ok, I’ll just settle for a blow job.” She laughs, a good sign I think, then…”Ok. See you then.” and with that she’s gone! I get home to see my ex has put a picture online with her new guy tagged “#Love” and feel a little sick. She’s only been fucking him a Month and a day or two. “Love”? Already?

I digress.

So now here I am. Back with Tinder. One girl, a nurse, has been messaging me non stop but still hasn’t given me her number. Flirts, teases, is clearly interested but playing the long con and to be fair, I don’t know if I can be bothered with that.

Feel free to call me shallow. I use the app for sex with a pretty girl. I haven’t lied about that and haven’t told anyone I want a relationship or even dating. I’m here to have fun, sex and that’s really it. In all honesty I wouldn’t be good for anyone in any other capacity and a man still without a job and soon without a flat is hardly the ideal catch! Still. The evidence is in, tinder is hard work and unless this one girl decides she wants to meet up I’m swiping left on the whole thing.

Give me some cash, decent clothes, a good friend and a bar any day over this shit!

Cheeky x

#Single#Tinder#Sex#Hook up#relationship#kissing#online dating#dating#fucking ex girlfriend

6/21/2013 (2:40pm)

Just discovered yesterday was national kissing day and was also the 1,250th day since I last had sex!

Blue ball


1/20/2012 (4:29pm) 11 notes

onto more pressing matters

So tonight I am meeting a lady.

She’s blonde, very hot, has a cute nose and incredible eyes. I met her Wednesday evening when she was sat at a table having a drink with a man whom I assumed was her boyfriend but was actually her fiance.

I looked at her, she caught me and smiled. I waited him to leave her and then I hastily went over, still unsure if he was indeed important or not, then proceeded to establish he was before getting her phone number and a date anyway.

Let’s be clear, we’re having a drink and then I don’t know what else except of course I do know. This can only be a sexual thing for her because she’s soon to be wed. He is away with work so she’s text me to meet up & therefore she will be terribly disappointed when my penis doesn’t work later on. I have the feeling that I’m a bit of a fraud as I was clearly cocky enough in my approach to suggest that tonight will be incredible penetrative sex and as much as this is a tricky situation in which to find myself I can’t tell her the truth as I really want to see her naked!

The first decent woman I’ve seen since Midninght new years day and I am spending time I should spend getting ready wishing I believed in a God so I could pray to them in vain hope that they’d reward me a hard vein…apologies to any lapsed Catholic memories that sentence may have stirred.

I’m assuming I’m just going to go down on her and joke my way out of any awkwardness that shall certainly ensue.

Sounds like a plan and hopefully biology might come to my aide before we leave the bar. Wish my luck science.



5/11/2011 (2:44pm) 3 notes

here he comes, ego…

At 4 o’clock on Tuesday morning, ego was sat in a girls house surrounded by four other girls holding court. Ego had been awake for a large part of the day before and had bumped into this girl, the same girl he met during some wedding that the world has been talking about. Ego cared not for the wedding as he found himself believing that any gathering of that magnitude was only a fitting tribute to himself, the very fact that two people were having their day followed by such a vast audience only served as a mechanism for ego to completely disengage with the event. Instead he ventured out and snaked his way beyond the throng of Union Jacks and past the Red, White and Blue banners to his old favourite haunt, females.

Yes, although ego may be currently impairedhe is still matchless here, in his comfort zone. No woman too pretty, no man too intimidating and no bar too tacky could detract him from his course. Now what are ego’s options? Ego is among the 80% of his fellow islanders who are against the nuptials of people of privilege and therefore could easily pick off the remainder of the options then there was the category people always underestimate, women get crazy horny at weddings, ego liked his odds immediately.

Here he comes, ego, in his splendid best, swaggering around and drawing in laughter from all who gathered, their affection and their fun like the magnetic fool he is. He takes a laugh and gives back several in return such is his generosity. Then there she was.

Pretty, even enough for ego, dark hair, a black dress and green eyes. Ego purred at the thought, he instantly has her, he’s already slept with her and all he has to do now is open a conversation. Of course, we know he hasn’t physically but not because she doesn’t want him to. She wants him, or she wouldn’t have kissed ego, ran her fingers through his hair and asked to see him again. Ego isn’t over the moon, after all, he expects this but for the time being he is satisfied.

This is when ego says yes in his own cocky, confident manner and allows her to see him again. Ego is now sat at 4 o’clock on a Tuesday monring surrounded by girls, green eyes is chatting to a guy but that isn’t difficult because there are many guys there and only 5 girls, 4 of whom are enthralled with ego. After an hour of holding court, he gets up, makes his farewells and walks over to green eyes, holding her hand and saying…

'one second, I'm just borrowing her.'

…over his considerable shoulder to the man he just pulled her away from. She smiles…

"Hello. Where are we going?"

…before following him to her bedroom where they kiss for an hour, he knows he’s good at that, then he leaves. She again bullies him to see her again.

Ego has withdrawn for now. He may not return. It depends if her boyfriend is around.

Sometimes it feels great to be cheeky.

Cheekyguy x


3/17/2011 (7:56pm) 3 notes

Deceitful Honesty

Since my operation I have found myself first of all lacking in attraction to anyone. I can honestly tell you that before it, a girl, early Twenties would often come up to me and flirt. It was never over the top flirting and could never be seen as brazen far more coquettishand nervy…she was nervous. She would often approach me, make semi eye contact and find some poor excuse to open rapport before drifting off and I found it cute. I never had a huge attraction to her but had found her very agreeable. Short, brunette, pretty, didn’t look too young and seemed comfortable with her body. It is safe to suggest I had thought about asking her telling her that we would be going for a drink very soon.

A week later my testicle hurt, not long after that it was gone and with it was my appetite. I saw her and under no illusion of my ongoing situation, her approach changed. She seemed to fall away from me quickly, the moment she got there she saw something was different and in a fashion equally as indirect as her approach made an excuse and walked away. That is the last time I saw her.

I changed, I had no desire for any woman and women had no desire for me. We all know confidence can woo and I had none but its a similar situation men find themselves in when they are in a relationship. Men in relationships attract women more so that when they are single. This is fact, irrefutable and no one is entirely sure why so they put it down to confidence. I have no offering of reason to add here, but it is odd and so was this situation. A woman had wanted me and then It completely changed in such a short amount of time.

It didn’t matter that I couldn’t do anything physically sexual with her and I really didn’t find her or anyone else attractive anymore but she didn’t want me? Panic stations everybody, a glimmer of cheekyguy wearing a cheap white suit in 30 years time crawling the clubs with balding head and beer belly stinking of Marlboro Lights and Issey Miyake, every woman averting her gaze to fix it with another girl whilst they laugh at him and raise their eyebrows. The desperation pouring out of him but that desperation was now some 30 years too early and was sudden filling the slithe torso of a handsome man in his late twenties and the horror hit me. Fuck! Whatever I had is sick, dieing, or worse already dead.

The first step in recovery was simple, just ignore it. The power of ignorance in not merely confined to bliss, you can put things off for a morsal until you’re ready, stronger to tackle them and that is half the fight, in any situation all the talent in the world means nothing unless you have the will.

I just went about my life, I had my ex who was great but that white suited man often reared his head and danced awkwardly at my niece’s wedding reception imagined in my mind, attempting to sleep with her friends. It was bearable but just. When you wake up to a puddle of semen that your body discharges without you having the erection to enjoy it or the orgasm that makes it allowable you begin to realise there are needs that only a hands on approach or a female touch can provide. Then you realise again that you can’t do that and even if you could you don’t find anyone you want.

With this mess clinging to my mind I saw a girl. The first girl I had actually fancied since my ex and for the first time in a long time, I didn’t know what to do.

When I saw my ex, now don’t get too interested as I shan’t tell you much about her, I was smitten, I could tell you what she was wearing, the first conversation we had and I can swear that I was useless. Since as long as I can remember before her and since I was never as nervous as when I was trying to get that first kiss with my ex. Quite simply one of the most beautiful people I’ve ever seen and as beautiful when I got to know her. She’s probably just read that as she finds herself doing so if you are, stop blushing missy! This new girl was the first time I’d fancied anyone in a long while and I was nervous but in an entirely different way.

As a man, these are some things I would think about when starting to see a girl.

* Will she be someone I can talk to?

* Will she be a lovely person?

* Am I only seeing her with beer goggles?

* Does she look as good naked as I think she does?

* Where should I take her?

* Will we have sex?

There are more of course but I feel these are the ones I immediately work through before a date. This new girl had indirectly said she wanted to go for a drink with me and so I said “Ok, lets go Monday.” and she replied yes. We had a date, I was feeling low and terrible fumbly with any women and somehow I had got a date. Then you can look through that list. Remove the last point or at least change it…

* When do I tell her I can’t get it up?

"I’m sorry lovely lady, it’s not you as you are ridiculously hot and after your drunken diplay of gymnastics I can see you are also deliciously bendy but I am unable to gain an erection. I could go down on you but thats’s about it."

Some of you may welcome an approach like that but when it’s the truth and you’re a man with altered hormones and one ball the confidence (or finding the balls) to say it is a truly difficult task. The first date consisted of getting drunk and chatting, there was also a massage thrown in. She wore her clothes and I cannot lie, I am incredible at massage…we had a second date again it involved drinking and then I kissed her goodnight, we had a third date, a meal at hers, with many drinks, a kiss or two on her couch and then…we didn’t have another date. I was a gentleman, kind, polite…boring! Not an ounce of Cheekyguy anywhere to be seen. My kissing got me a second date but my inability to be me refused me a fourth.

To be just to myself, this girl was slightly odd. However I didn’t feel comfortable around her. I could usually take control and make the situation bearable but with no erection on hand I felt numb, disabled.

The next girl I fancied, was a girl I was working with, slightly older and also gorgeous but we didn’t even get as far as the date. We talked, drunken talk. arranged to meet up and then nothing. We would see each other, she told me a week or two later that when she was less busy we would meet up becuase I was fun and lovely…then she stopped texting me back.

Now all of this can be explained in many ways but the fact remains, this situation is without a doubt alien to me. In the past I would get annoyed and then either get a date anyway or forget about it outright; in most cases, I’d get the date. I’d probably just take them by the hand and lead them away from prying eyes before kissing them. I couldn’t even do this! My confidence, although heavily fueled with alcohol, just could not give me the tools for the job.

This brings me to the next stage. Out and out attack. My ex told me I should go out and just kiss. Kiss everyone, kiss their friends, kiss their boyfriends, kiss them again. It made sense.

Although reluctant I went for it. Any amiable lady I saw regardless of how attracted I found her, I had to kiss her. Cue several slaps, a number of adds on facebook and a phone number or two. I’m not back yet, I shan’t be until that lump between my legs begins to behave itself but I know one thing. Regardless of the confidence levels in any situation I find myself, deep down I do know, I could probably bed anyone. Just as soon as this works.

Cheekyguy x


12/2/2010 (4:28pm) 3 notes

Strangers on a train

Hello you naughty naughty tumblr’s. I’m hoping that wherever you are you’re not as cold as I am, been on a train for several hours over the last couple of days and am only now regaining the feeling in my poor toes.

Saw a girl on the train today and whilst trying to get tumblr up on my phone, a process that thus far has eluded me other than very basic functions, I was reminded of an escapade that happened to me 3 years ago.

A friend of mine had a surprise birthday party in a swanky abode in the North of England. This girl was money. A twin no less and this house with several acres of land belonged to her father, a man that had found a highly lucrative niche in the business market and for his daughters celebration had decided to throw an extravagant party. The place was incredible, a small campsite erected exclusively for guests to stay in after the party, a marquee in one of the several fields adjoining the house filled with a free bar, a dance floor, tables for guests to dine, a plethora of live bands, champagne reception, spit roast hog for everyone, a live firework display and, my favourite attraction, dodgems set up in the back. Everyone was dressed up and beautiful women were everywhere. Including the one girl I was too drunk to sleep with and passed out on top of…but I digress.

My story begins the day after, a Sunday. I was driven to the station and placed on a platform vaguely facing my destination. My head was not my biggest fan and only due to the amount of food I’d scoffed and orange juice drank that morning was I now faced with an annoying headache as opposed to a serious need for a discover a place to relieve the contents of my stomach and desire to forget the shame of failing to succeed with the aforementioned lady.

It was at this moment that I spotted a young brunette standing beside me looking at the same train information as I. She was short, roughly 5’3”, had a white jacket on that looked awfully refined, this bobbed cut hair draped over some perfect olive skin and picturesque brown eyes. She pulled her headphones out and asked what train I was getting. Jackpot, the same one, time to man up and promote the Alpha version on Cheekyguy.

I proceeded to lead the two of us directly to our correct platform and on time, actually we we’re 5 Minutes ahead of schedule. “Where are you heading?” I asked as nonchalantly as possible, you can imagine my delight and veiled excitement when she came out with my destination. No, that’s not true, she was travelling further than me but I was one of her changes, one of 4 for her and the final of three for me.

I must confess that despite my appetite and catalogue of conquests with members of the fairer sex that this situation simply does not happen to me. I’m many things but not this opportune, in normality I have success meeting women by means of friends or work, which gives me the prospect of making the acquaintance of many young, beautiful, nubile women. I’m the infuriating chap that can talk women into bed but still needs some rapport built before hand. This woman however approached me to talk, she instigated conversation and right now she was the one with her gaze fixed on me, scanning me up and down and giving me serious “fuck me eyes”.

“What’s your name?” she said “*******” I told her, debating with quick speed just how important it was that she asked first. Now do I ask or let her tell me? “Emma” she retorted without prompting. This can only be a good signal.

We sat together and settled in for the first leg of the journey. I don’t think it’s worth mine or your time boring you to death with the entire conversation…so these are the bullet points of what I learnt, primarily without me asking, on the first hour long passage before our next connection.

·         Name: Emma

·         Age: 19

·         Job: Student (Business and Japanese)

·         Ethnicity: Danish, Italian, English

·         Reason for journey: Travelling across country to visit…

·         Marital Status: Boyfriend!!!

Let me explain one thing to you. There is nothing sexier to me than someone who is unattainable. With certain exceptions such as a family member, pet or a friends partner (in no particular order of allure there) if somebody I want is off limits I’m even more drawn in. Maybe because it’s a challenge, maybe because it’s deliciously naughty of us to do this, maybe because deep down I want to destroy others happiness although I seriously doubt this last one is the case but whatever the reason, it’s incredibly hot for me.

With this in mind and our first 15 minute wait looming, we hit the station and I ask her “Let’s get a coffee.” I help with her bag we find a place still open and I make her buy her own. Never buy a woman you’re attracted to a drink, it can only send out the wrong message. A female friend, work colleague, a friend’s girlfriend/fiancé/wife all these are acceptable but never buy any other woman a drink if you wish to be successful.

Next train arrives early so we board and she takes off her jacket again this time I can have a good look at her bottom. It didn’t disappoint. Even through these jeans she was wearing it really did look perfect and as usual had taken all my attention away from the fact that she had no boobs. This is so not important to me as I believe I’ve said before, a woman’s face and her derriere are the only thing I’m interested in when it comes down to lust and she was thoroughly talented in both departments. We sat down I turned my gaze back to her eyes and smiled, she was so pretty there was the possibility of me having to drape my jacket over my lap to disguise any erection that may interrupt us and show me up as the deviant I am. It wasn’t long before she talked about her boyfriend but in a way I wasn’t expecting, she discussed their sex life. Brazenly, openly with a care free abandonment of the people around us who could very easily have heard her, she talked about places, situations, positions and finished off by telling me in no uncertain terms that “If only have boyfriends because, well, I’ve a very high sex drive, I like it but don’t want to be called any names.” I took my jacket from the seat beside me, pretended to get something out of the pocket…then draped it over my lap wishing we had grabbed a table seat.

This part of the journey was the shortest and at the next station there was only a 5 minute turn around thanks to some delay. There was no way now I was passing this up. I had to have courage and far more importantly a condom. Many stations across Britain are littered with pubs and this was my best chance. Luckily we were on the right platform for our next train so I left my bag with her and sprinted to the pub in the station using a half baked excuse about the gent’s room. £3 for 2 condoms is steep in anybody’s situation but this is no time to haggle with a machine. A quick jaunt back and on the train for the last 2 hours of the journey…the time to take the plunge.

We were on, a deserted carriage, our conversation hadn’t evolved from sex but the content had grown more intrusive. She got up to go to the toilet; I sat there and looked at the small box of condoms in my jacket pocket, my hands were dirty from the various banisters around three different stations, my watch called me, the second hand moved to 30 seconds, I stood up, removed my jacket keeping hold of the condoms, walked towards the toilet door, what will happen if she says no? It’s a big train, fuck it, sit somewhere else, opened the carriage door, are you seriously about to fuck in the toilet of a moving train? The train jerks, regain balance, she must be thinking the same, the conversation, second carriage door, her high sex drive, toilet door is right there, no one’s around, she wants you, toilet door, vacant, I open it.

There’s a brief moment where I think I’ve got this entirely wrong, she’s stood fully clothed looks at me with a mixture of shock, horror and disgust. “Hi” I say walking in and closing the door, don’t be backwards about coming forwards I thought. “Hi” she says dropping her head at an angle with a seriously mischievous and wanton look. I rush at her with a forceful kiss slipping my tongue directly in her mouth and caressing hers, my hands either side of her face and she immediately follows suit. She goes straight for my belt undoing it, opening my flies and pulling my dick out, I slip her top off over one shoulder and kiss her neck, she enjoys it.

“Fuck me” I pull her jeans and knickers down, they are French, my favourite, and start with my hands whilst still kissing her neck. I tell her “say please”; she pulls my head away from her neckline and stares at me. “Please fuck me” she means it.

She places her right leg up and rests her foot on the toilet seat lifting her pelvis up my body and wrapping her left leg around my waist. I quickly pull the condom on and press it into her. I fuck as hard as my hangover will allow me and then harder holding my breath to exert less energy and focus it all on her. She bangs her hand against the door and then slides it up my top scratching at my back and drawing blood. I pull out and turn her around, forcing her up against the wall in the cramped cubicle and push myself back into her.

I knew I was close and this was amazing as condoms are my least favourite friend but this was intense and incredible. I felt she was close too but wanted to make sure I wasn’t first or my competitive edge would have never accepted this defeat, so I thought of the filthiest, most excitingly dangerous scenario I could envisage at that moment and said “I wish your boyfriend was here so he could see how big a whore you are.” It worked; she came, her body still shaking against mine as I came inside her. I kissed her one more time on the lips but tenderly, they were cold from her heavy breathing and seemed grateful for the attention. Then I pulled out. We prepared ourselves and walked back to the seat holding hands.

She sat beside me and we held each other, we swapped numbers knowing full well we’d never make use of them, this was a once in a lifetime chance moment and could not be recreated. We stayed like that until my station where we had one more kiss then I left her there and got a taxi home.

I did text her about a year later, she was living closer to me then and we met up for a coffee but didn’t have sex. We added each other on Facebook and hardly ever chat. It just wasn’t that sort of hook up. While I’m sat here with the blood slowly coming back to my feet and after seeing another pretty woman on the train this morning I know, nobody is that lucky twice and maybe that’s how it should be.



#Sex on a train#sex#kissing#pussy#hot#brunette