There was a period in 2006 when internet dating was becoming more of a job than a hobby. I was literally fitting my employment around my sex life. Organising my diary was reaching a point whereby I’d need a skilled professional to juggle all the sexual engagements; so I knew where I was going, who I was meeting and what I was expected to do.
Young lads (legal teens) were easy. They tended to have the emotional capacity of a tea spoon and really just wanted to get laid. Whilst there was minimal emotional labour involved, these dates were physically draining. When presented with the opportunity of no-strings fu*king for one night only, sex starved, horny young boys liked to make the most of the time they had. Bought up on a culture of internet porn, not only was I competing with a high level of fitness and stamina, but I was expected to recreate and execute acrobatic pornographic feats ‘just like on the web’. A good pounding was always welcome but nearing thirty I couldn’t maintain the pace or endurance required to satiate these beautiful young men on a regular basis. Thus my schedule offered a degree of sexual freedom as I accepted ‘dates’ from men my own age or older.
My preferences in these situations were to accompany older gentlemen. Men my own age were far more critical in regard of appearance (and I had piled on the pounds), plus they were very ‘modern’ and ‘pc’ – treating women as equals in the one situation where you’d rather not be considered an equivalent. I’d offer to split the bill. They’d accept my invitation. I hope I don’t come across as a bitch here, but I think if a man asks you out, it’s his job to pay on the first date. Might be harsh and feminists round the world may castigate me, but if a man accepted my money to pay for half the check there would be no sex and certainly no second date.
These kinds of incidence were rare with the previous generation. Nearly thirty, if a man in his fifties of sixties was taking me out, I knew I’d be treated like a lady (and guaranteed my credit card balance was kept to a minimum). Plus (again a cruel observation) these wealthier, well educated, middle-aged men appreciated the beauty in youth.
Writing this at thirty-six, let me assure you, only this week I was sitting on a train observing a nineteen year old university student. He was probably a virgin. I doubt he had a girlfriend. I suspect he was shy and inexperienced with women. I imagine girls barely notice him, let alone fancy him enough to take time to get to know him. But he was beautiful. He radiated youth. Spectacles, spots and slimness were irrelevant; it was his youthfulness enticing me to the degree that I found myself staring intensely at him (possibly considered freaky on public transport).
On reflection, many of the more mature men I dated didn’t see a fucked up, fat, twenty-something; instead they saw someone twenty or thirty years their junior still in possession of the ever elusive quality of youth.
Hence I sacrificed a right old ramming for a taste of expensive wine and fine dining.
Enter Mike (shocked I remembered his name, right?).
Mike was in his early sixties. He was head teacher at a prestigious bordering school. Mike had the banter. He wasn’t your average, pompous, stick up the arse Brit; looking down on the lower classes (especially those originating from a colony of convicts). Having adhered to a reasonable ‘just ensuring you aren’t a psycho’ timeframe, participating in successful textual intercourse and engaging online conversation, we agreed it was time to step it up and press the flesh.
I vividly remember this one night for various reasons.
Firstly he was driving his own car to come and collect me from my home. Bonus – private transport and no paying for public transport.
Secondly he was happy to dine in my local area. Bonus – close to home and a short journey whether things went good or bad.
Thirdly he invited me to choose a restaurant. Bonus – there was only my favourite tapas bar La Rueda up the road that my budget didn’t stretch to and I’d spent months dying for a fix of Spanish cuisine.
Waiting outside on the stairs, leading to the terrace house which had been converted into studios and bedsits, I must’ve appeared quite swish because I was complimented by various locals – all offering to keep me company or wanting to exchange numbers. I politely declined because I was going on – a – date!
Unfortunately his car was black and it was winter. Seemed like every car driving up Stockwell Road was dark and I found myself dashing into traffic waving people down only to discover none of them was Mike. In one case, a driver happily wound down the window and opened the door to take me for a ride, but I retreated hastily – Stockwell and Brixton do not possess unblemished reviews in respect of activities and the residents.
Eventually a four-wheel drive pulled up. The door was flung open for me to observe Mike’s arrival. I’m told it was a 4×4 Range Rover an expensive automobile. Struggling to haul myself in, I was less than impressed with the car irrespective of its price tag.
Not unexpectedly, Mike raved about my looks – a spell we now know which was conjured by the thirty plus age gap as opposed to me genuinely being blessed as extremely attractive (oh my false modesty!). It Thursday night and Clapham was bustling and busy. By the time we found a parking spot, I could’ve walked from home. We then had to contend with a packed restaurant, but the time passed speedily as we enjoyed umpteen sangrias.
He’d never married nor had children, preferring a bachelor lifestyle – which allowed him a very nice residence in his very posh school.
Each Christmas he held an exclusive party, which he couldn’t wait for me to join him as his date this year, whereby he would supply the most delicious food (including a pig on a spit) and a wealth of delectable and tantalizing alcoholic beverages. BUT, it was a Christmas party and people were expected to bring gifts.
Turns out Mike was a connoisseur of wine, with (yawn) an extensive and pricey cellar stocked with the stuff. Although unspoken, it was implied attending guests would present Mike with a suitable and appropriate vintage. The party amounted to almost £100 a head per person, so Mike felt this wasn’t an unreasonable expectation.
Two years previous, a new member of staff was invited to the party and bought with him a £5 bottle of Sainsbury’s Own red wine. Suffice to say the following morning, Mike returned the bottle to the teacher’s pigeonhole with a post-it saying ‘Keep it. Your palette will enjoy it far more than mine’. I need not wrap up this tale with the inevitable conclusion enlightening you as to which of the teaching staff never received a return invitation to the annual party.
Whilst I was discovering these insights into Mike, we wolfed out way through at least ten plates of tapas and two bottles of red wine.
Settling on a third bottle of wine for dessert (I actually would’ve preferred the mudcake with fresh strawberries if you’re reading this Mike), Mike disclosed he was a rugby fan (no surprise to the middle and upper classes) and played a lot in his youth. In fact, he carried on coaching the school team throughout his prolonged career. However all that impact on his joints had taken a toll. He proceeded to drop the bombshell that he’d recently had a hip replacement.
I suddenly became aware of how dark and soft the candle lit restaurant was. The lighting prevented me from examining his looks with a degree of scrutiny. He sounded bright and funny and charming, but hip replacement smacks of ‘granddad’.
I was thrilled when we left the hazy, fuzzy ambience of La Rueda. Not solely because it permitted me the opportunity to study Mike properly, but because the rich food and wine was having a funny effect on my tummy.
I advised Mike to hail a cab, but he was confident he could drive. The car was a monster so in all likelihood if there was an accident we’d be safe. However as a civic minded person and having lost people to drink driving, the trip was an endless white-knuckle rollercoaster. My eyes clenched shut as I prayed to a God. In a bid to ensure everyone returned safely, I barely uttered a word for fear of distracting the driver
Obtaining a parking spot near my house was infinitely easier than in popular Clapham. I can’t deny (for his age) Mike was handsome. He did have a rugby players build. He was very personable. I certainly wasn’t deterred from having sex with him.
Neither was he.
As soon as we were through the door, he was lifting my black dress up and hooking his fingers into my one-size-too-small control knickers to drag them off. Lust can bring out the beast in anyone. The aged sixty-something yanked my knickers down, tearing my tights in the process.
That he was bedazzled by my pussy, I let myself follow his lead. He was desperate to bury his face in there and who was I to deprive him? I was irresponsible. Dress hitched up, I sat on the edge of the bed, spreading my legs wide to reveal the shaven haven. Bare, soft plump lips he was frantic to part and taste. Too keen in hindsight. To let his tongue wander he needed to get on his knees. His firm hands were gripping and spreading my thighs further apart, but he was kneeling and rocking noisily as he performed oral sex on me.
I should’ve laid back and enjoyed the sensations, but I was inclined to watch the commotion between my thighs. One of Mike’s legs was sticking out crookedly. As he smothered his face in my juices and tried to tongue fu*k my slit, he was rotating left and right like a remote control robot without full functionality. The odd angle of the leg where his hip had been replaced had me transfixed.
I think mentally he wanted sex, but physically his body was putting up resistance. Like a feral dog with a twisted, bent, broken leg and no veterinary service, the attention to my pussy became ineffective and chorish, as he squirmed to position himself to taste a woman (for the first time in a long time I suspect).
The picture was totally wrong. He was in a suit – bold and brawny. Whilst his top half remained solid and sturdy from his rugby playing days, his lower half was withered and warped as he dragged himself on the floor like a peg-legged pirate.
I didn’t want to emasculate him by audibly suggesting changing positions. The suggestion might be classed as bad mannered, but something had to be done as the oral sex had become a trial to me.
Wriggling back on the bed, I stretched out to encourage him to join me. In my head I had real concerns me on top would shatter the newly replaced hip. As he awkwardly hoisted himself to stand, his face was beet red from the effort and shiny from my lubrication.
‘Would you mind bending over the bed so I can take you that way – it’ll be easier on my hip?’
I was grateful for the instruction. In that moment there was no giggle to suppress but looking back, my relief there was an end to the evening in sight had me as overjoyed as the girl that escaped the house of the Texas Chainsaw Massacre.
Squatting slightly, bending over the bed and supporting my weight with my arms stretched outright on the mattress, his lifting if my dress and caressing of my buttocks was in fact quite sensual. Stroking my thighs, I parted my legs to let his pleasingly hard cock slide into me.
The sensuousness of the moment passed as he reverted from teacher to school boy, fumbling to find the right hole. Repositioning myself, I reached under to guide him in. He groaned so loudly at the initial penetration I was worried the neighbours would complain. Firmly embedded in my slit he began pounding me hard – much harder than any of the other elderly men I bedded. His hands were on my hips so he could slam himself into me (at a comfortable angle given the restrictions of his surgery).
The snag was the force of his fu*king had turned my stomach into a washing machine. As I bounded and rebounded off the bed and he banged hard and deep into me, my dinner became dreadfully unsettled. Unsettled to the point where I thought I was in danger of encountering an accident of the brown variety.
This could not be allowed to happen. The longer and harder he went, the more delicate and unreliable my digestive track became.
I needed to end it fast, so literally crawled onto the bed, spat in my hand and worked that cock quickly and rhythmically till he came.
Pleased at his climax I thought he’d leave (it was a school night after all), but he was attempting to kneel again for some Australian bush.
I’d no real option but to eject him kindly with a sorry, pathetic excuse of an early start at work in the morning. The second he was out the door I had tapas escaping both ends when my arse hit the toilet bowl. It was regurgitated red wine in the bathroom sink, and garlic prawns, chorizo, and patatas bravas in the toilet bowl. It got to the point where was I was forced to leave reading material in the bathroom I shared with three others, my visits were so regular.
Subsequently, Mike was always arranging dates and cancelling them for one reason or another (well he did twice: one was for a school trip the other was to do with…his hip replacement). In the end, despite his promise of an invite to the big Christmas party (to which I’d assumed as his date I wouldn’t be bound to adhere to the ‘bottle of wine’ rule) when he finally secured a time and place, I chose to cancel. Sure the pig on a spit was alluring, as was that cellar full of expensive wine, but the memory of an old man literally grovelling and crawling on his knees for pussy did kill any passion or romance the relationship may have potentially had.
PS – Yes I know it was bad manners on my part not to reciprocate the enthusiastic oral sex I’d received.
I was sitting on my therapist’s couch yesterday in a bid to determine why exactly I hadn’t updated my blog as regularly and routinely as in the past. A few points arose:
- I was getting absolutely no action in the present and therefore was as mentally distant from my sexual self as I was physically,
- Reflecting back on these posts I realised as fun and as frivolous as fucking a hundred plus men had been there had been numerous times I glossed over the reality of some of these situations which had in fact been somewhat psychologically traumatic and this fact was beginning to permeate my memory rendering the blog a more tortuous task than a body of fun work;
- We also considered the lack of direction, control and focus in my life but that really is the boring psychotherapy stuff.
So I’ll give you an example and I’d be interested as to who finds this story sexy and who finds it disturbing (and who finds it shit…maybe don’t comment on the last point given my low self esteem at this moment).
Many moons ago I fell for a married man. Chris – the inbetweener. I’d had my first love and was quite convinced I’d never love again. Now I’m married so my husband who is my true and grand passion, but Chris was the man that allowed my heart to realise it could love again. Now I’m married – no to Chris – clearly didn’t work out with him, but I’ll roll onto that story at some other point in time.
Because I was heart-broken and fully aware Chris himself hadn’t really wanted to end the relationship, it was just practically it couldn’t work long-term, I felt the best way to punish him was to fuck other married men. Enter the website ‘Illicit Encounters’ set up purely for married people (or those in long term relationships) looking for like minded people to fulfil the sexual side of their relationship that has gone wanting over the comfortable years with a long term partner.
I had put my age down as 27 when I was in fact 31 and tended to approach older men….like late 50s, early 60s. In this way they’d be so flattered and surprised by my tentative advances they would be less inclined to reject me. I have to say in most cases this was true. Occasionally you would get the odd ‘honourable’ (if you can adopt such an adjective for members of the website) gent saying he felt it wasn’t the best idea because of the age gap and that having daughters of a similar age made it inappropriate. However on the whole I’d get many an invite for dates and more because they tended to have daughters older than me.
One such man was called…..Peter…maybe…I think. He was a 58 year old engineer from Essex that had made his life in Ireland. He seemed an attractive enough man with a frame of 6’4, broad shoulders, a gentle but square face. He was literate enough over email to attract my attention and almost consumed by the fact that I wanted to ‘embark on an affair’ with him – which wasn’t strictly the case but I felt we could iron out the finer points of the relationship upon meeting. What was spectacularly unusual was that he was actually willing to fly from Ireland to Dublin to spend a night with me under the premise, to his wife, that he was visiting his family in Essex.
In some respects I found this phenomenally becoming but I was also a little struck by the impulsivity given we’d never spoken on the phone r met in the flesh. I was completely honest and up front about my size issue – I was undoubtedly photogenic but was considered very voluptuous at a size 16. Perhaps warning bells should have gone off with me when he wrote back ‘so you’re a fat bird then – you can’t be that big given the photos’ (he clearly knew nothing of how to angle a camera for the best shot).
He was undeterred by my weight and decided to pay the fare (I assume he went Ryan Air – for a sex fuck you’d only risk a discount airline) to visit. I decided he was either smitten or a psycho. It didn’t matter which. Well not until I found myself typing a message that he was welcome to spend the night at mine – I felt a little mean insisting on a hotel given he was flying over to fuck me; free accommodation seemed a reasonable contribution on my part. This was, in hindsight, perhaps not my best or most considered decision. Heartbreak and payback sex are not a combination to bring out the ‘sensible head’ on anyone’s shoulders.
Friday came and I dressed accordingly. I was due to meet him in a pub on Carnaby Street, where my workplace was located. I worked in the music industry so my attire had to be casually flattering in a semi-professional manner. I opted for my jeans and a figure-hugging blue top which not only accentuated my curves and rather perky large breasts but the depth of colour accentuated my pale skin tone against the dark features of my hair and eyes – unassumingly stunning. Because of his height I could even afford to wear a pair of very high heels.
He was handsome for his age and dressed in cords with a collared shirt and some patterned knit-wear jumper. He looked me up and down and decided I’d do. I reached this conclusion as he delivered a hefty slap to my rump with an introductory comment of, ‘You weren’t kidding about your weight.’
That comment sat heavier with me, than I did on the pub stool I suspect. We chatted inanely about his work, situation and I’m sure I exchanged equally banal conversation. I saw his eyes light up when he spoke about how I was younger than his own children, and what a coup it was for him to nab someone so young at his age – what a topic for discussion down the pub at the village he lived at in Ireland (I didn’t think bragging about a young online conquest in a small village was the best idea given it could easily get back to his wife, but steered clear of advising him of this). The more I realised I was nothing but a boast, the more I realised how much my heart still hurt for Chris and how this man, whose name I honestly do not even remember, could not have been any further from being the man Chris was – or had been to me.
I stared at his over night bag as he reluctantly bought me alcopops (clearly he despised my common taste on that front) and felt my eyes well up with tears. It would sound clichéd, but it was true and if I said it and committed to the decision I may well escape the night unharmed. Through the tears I admitted the whole scenario was a bad idea. I apologised profusely that he spent the money flying here (even if he did have friends and relatives to see) but that I couldn’t sleep with him. I just wasn’t ready and to try wouldn’t be right for me.
It’s funny how quickly a man’s character will change for a bit of fanny. He became gentle and caring and tactile; in an instance saying how he completely understood my change of heart and it wasn’t a problem. He even offered to walk me to the tube station. It was a kind gesture. Feeling fragile I accepted. Then he offered to walk me down the steps into the tube station itself. I suddenly had a sinking feeling that I knew exactly where this was going. I gave him the goodbye kiss with as much fake passion and tongue as I could muster but it was the wrong move.
Suddenly he became overbearingly nice saying he’d accompany me home, I didn’t have to sleep with him, he could just cuddle me, he was in an awkward position having to ring friends and relatives for a place to stay at this hour (it can’t have been any later than 8pm). I suppose I wanted him to be genuine so I said as long as he understood the situation he could of course stay at mine. There’s nothing like being guilt tripped with the price of an air-fare (even if it was a discount airline).
As an aside when we got into my bedsit/semi studio which consisted of a large double bedroom and a second room which was a large kitchen I noticed my hamster’s cage which resided in the kitchen was vacant. I couldn’t find the creature anywhere and was slightly perturbed at the idea of him running round the walls and shitting everywhere. I’d given up handling him after a bite so I was as frightened of him as he was of me. I think shifting my focus to the obsessive need to recapture the rodent resulted in my guard coming down and my senses not being overly aware of my predicament.
The next thing I knew the 6’4 old man was behind me attempting to grind his hard penis against me as he tried to be seductive and grasp at my breasts. I felt flustered, completely compromised and very threatened. I muttered that I really didn’t feel I could have sex with him. My attempt to avoid his lechery in the kitchen meant my only escape was the bedroom. Here his physical dominance came into play; his stature and determination as he walked, talked and invaded my private space – his voice was almost calming and reassuring me this would happen and I’d be okay – I was eventually backing away until I had no where else to fall back to other than sitting on the bed.
I knew what was coming. I felt defenceless to refuse or stop it. I began crying saying I wasn’t ready but he said it’d be okay and we’d just cuddle.
I didn’t realise cuddling for him meant undoing his trousers and tugging them down enough so his hard old penis had room for some forceful action. I was unaware that cuddling meant pushing me down on the bed and telling me to just close my eyes and relax. I didn’t know cuddling meant he would undo my jeans and pull them off hurriedly. Who’d have thought cuddling would have involved him climbing on top of me trying to kiss my lips as I cried. Who’d have guessed cuddling would involve roughly grabbing and sucking someone’s breasts as they hopelessly repeated ‘I don’t want to do this, I don’t feel like doing this.’ I certainly didn’t know cuddling would result in someone forcing my legs apart, easing their cock in me and slowly and rhythmically working it in and out of me while pinning my wrists to the bed. I never thought a cuddle would eventuate with an old man moaning in my ear about how tight I was, how young, how much this meant to him, how grateful and thankful he was as he built up speed and came inside me.
He got off me and I felt anything but a boastful sexual conquest. I felt fat, my body manipulated into an unattractive position so he could get his one last young fuck for the wank bank. And I must’ve looked it because all he said as he pulled up his trousers was, ‘Don’t worry I’ve had a vasectomy.’ I stared up at the skylight and noticed how heavily it was raining. I wished the window would break and the rain could wash it all away – the pain, the shame and him.
I didn’t have to worry about him staying the night. Seemingly spending the night in a storm that didn’t look like it was about to ease up any time soon was far more appealing than spending it was me.
‘I’ll go now,’ he said.
‘You can stay – it’s silly if you’ve nowhere to go.’
‘I can walk round in the rain till morning. To be honest you’re really fucked up and you need to get help.’
And with that he left. I don’t know if it was unfortunate, foolishness or rape – who can say. I did feel though, as an outside observer, having witnessed both our behaviours in that situation, on a scale of fucked-upness he would’ve scored higher than me.
So that’s one more of the one hundred. That particular encounter brings back no fond memories or frisson as I write it. But fucking 100 men, one was never to expect a 100% perfection hit rate in all those sexual encounters. Good with the bad and all that.
What I will say, is after the absence and devastation this vile old predatory creature had left me stewing in and a good deal of comfort eating on my part the hamster eventually made himself known within the bedroom walls (And I thought my nightmare ended with the faux-rape but nothing will drive you mad than constant squeaking in the walls). By Monday morning the hamster had been moved to a dumpster with all his food and bedding. I hope nothing bad happened and he escaped the bin men. I like to think some rats adopted him and he’s part of a rough gang still going strong in Stockwell. He was better off out of the apartment – so would I have been on that particular night.