Whilst fucking barely legal boys was fun and in no way emotionally draining; one predictability with every lusty youthful encounter was that you weren’t going to be treated like a princess in public – in fact it was guaranteed you’d not be leaving the bedroom. Older men on the other hand were so inept or unused to the dating game they would lavish attention (and money) on a pretty young thing some 20 years their junior. And there are many tales there I will draw on at a later date.

What sticks out most in my mind in terms of old sex is sleeping with a guy that was 63…when I was 30…and he thought I was 25 (I lied on my online profile). There is another story that eclipses that one in terms of age difference but it doesn’t involve cock so it can wait.

There may be those that have heard of, subscribed to or read about a sordid little website called ‘Illicit Encounters’ – a ‘marriage dating website’. At its inception it pretty much hooked up disgruntled, unsatisfied people in marriages (or long term relationships) looking for a little sexual side dish outside of their dreary lives.

At the time to join you couldn’t actually be single, so I had to opt for separated of divorced. It was all very hush hush and under the guise that everyone respected the vows of marriage and concept of family but appreciated certain aspects of a relationship may diminish or be completely eradicated. Sex starved married men could hook up with equally sex starved wives and neither person’s marriage would be jeopardized – usually. Indeed the website comes with a warning: Not everyone is suited to having an affair. They are not an alternative to working on or ending a marriage. Not all affairs have a positive effect on a marriage, some can be very damaging (no shit Sherlock!). Always consider other people and if you are going to have an affair, please select your partner wisely (have you seen Fatal Attraction???).

What appealed to me about the website wasn’t so much the no-strings sex, or that I didn’t have to stress about getting involved in something heavy like an actual relationship but the fact that while females joined for free, male memberships ranged from £100 – £250 per month. Any man that could afford that sort of money usually had additional disposable income to share with their selected date.

Believe me I cashed in big time on that particular aspect. I’ve never eaten or drunk so well. Allowing for such a huge age gap worked in my favour, they were flattered and in some ways I was paid accordingly for being presentable, educated, young and slutty. It was a win-win situation (well not always but no need to dampen the mood with the horror stories of the darker side of this seedy sleazy website).

It wasn’t the man that bestowed the most money on me, or was the most in awe of my beauty that won me over: It was the sixty plus someone that was confident enough to make me do all the chasing that had me desperate to bed him.

After an exchange online and a few texts we decided to meet. Did he take me to a posh restaurant, make a grand gesture like the others? No Grandfather George* in his Saville Row pinstripe suit was happy to see us slum it in a Samuel Smiths pub – no music, no decore and £2 pints. His off-handish manner changed him from being a piggy bank or doormat to a conquest. And boy did I have to chase.

He teased me with texts suggesting possible meetings and all sorts of lewd activities but nothing came to fruition. It drove me mental. What little dignity I did have I cast aside. I had a text some 4 months later asking me to met for a drink one Friday evening. Had I possessed any self respect I’d have said no and to call in advance and take me somewhere befitting a lady of my style (that last part suggests unrealistic ideals of grandeur but a girls gotta dream). Instead I agreed immediately.

We met at the pub with a brisk kiss on the cheek and ushered me into the same cheap, bland pub and literally said: ‘I’ve only got time for a quick drink but next Tuesday I’m attending a work function in London and staying overnight in a hotel. Do you fancy staying in the hotel and fucking me?’

He’d played so hard to get, regardless of his arrogance, lack of style and manners, for me bedding him became the game. That was the end result. Whatever indignities I would endure of the journey was irrelevant. I would not have someone twice my age turning me down for sex.

After that drink. Nothing. I didn’t even know if Tuesday was on. Given his prick-ish behaviour I assumed he would call it off (and not even bother informing me of the change of plans) so didn’t come prepared for an evening sexual dalliance. After returning from lunch I had a text with the address of the hotel, room number, my expected arrival time and the time he was leaving to go to his work function. It was cold and calculated and we both knew I was going to obey.

Game on.

Only I looked a mess. I could borrow my work colleagues make-up and even a pair of decent shoes but because I was significantly overweight in relation to my peers I just didn’t have a choice of clothes to borrow form. Working in a music company meant the dress code was lax and my preferred choice of attire to disguise my significant bulk tendered to be jeans, trainers and huge oversized sports tops. It was comfortable but not in any way sexy or flattering to the figure and despite all the creative types present there was no way to sex it up.

Working in a music company also meant we were paid a pittance because everyone wants to work in music so with demand outweighing supply I had didn’t have the money to buy a top in any shop in the West End where my work place was based. Instead I had to run up to Tezenis on the corner of Oxford Circus. For those of you that don’t know Tezenis is a cheap underwear and pyjama shop. The best I could do was find a low cut skin tight pyjama top to masquerade as a blouse for the evening.

It did the trick – well it didn’t stay on for long so I looked feminine and reasonably presentable.

I got to the hotel and knocked on his door.

And I was faced with a 63 year old naked and fresh out of the shower with a towel wrapped round his waist. Before you start gagging at the mental image and branding me a  gerontophile (that’s a person who has a sexual preference for the elderly – think opposite of a paedophile) let me tell you he was actually pretty buff.

He was a silver haired fox and rather good-looking but short; shorter than me in heels so maybe 5’6. Broad but his body looked like it frequented the gym regularly. He had a defined hairless chest and a flat stomach – okay there was no six pack but it was hard and tight. He was muscular, I’ve heard from a male friend that’s a little vertically challenged that it’s a lot easier to stay in shape when you are smaller and maybe this was the case with Granddad George. Don’t you just hate it when someone is phenomenally good looking but a foot too short for their beauty to be truly appreciated? Man that must’ve been him when he was younger. With money, sharp suits, an acerbic tongue and high level of intelligence his attractiveness was now off the scale at 63.

I kept remembering the episode of ‘Sex and the City’ (The Man, The Myth, The Viagra) where Samantha goes on a date with a 72 year old billionaire and convinces herself the sexual side of the relationship will be fine because ‘all cats look the same in the dark’; when faced with the bottom of a 72 year old she realises the sight cannot be forgotten no matter how dark the room.

By the time he dropped the towel I was so mesmerized by his cock I didn’t have time to be repulsed by any wrinkles. It was a whopper. Like a pepper mill. Long and thick…..and limp, but not unattractive – quite wondrous in truth. There was no viagra available and believe me getting enough blood down there to support such a beast was hard work. Clearly my low cut pyjama top did not scream ‘lady of the night’ so my hand was working his cock like a water pump on a well. Once it was hard though it was a magnificent creature. Upon entry I could feel vagina stretching to accommodate him and once he was in there he thrust away – robotically almost. Then his watch beeped, he withdrew methodically and said ‘Right I’ve got to go to dinner now. Not sure when I’ll be back so you can go home now if you want.’

No way was I leaving that luxurious hotel – particularly as I felt a little like I’d been a disappointing shag. I needed a chance to rescue my reputation (didn’t want a bad rap on ‘illicit encounters’ and risk jeopardising my new posh social life) so smiled sweetly saying I’d wait. I watched a film, ordered room service and rang all my friends from the room’s phone (wonder how he felt when he got the bill on departure).

He didn’t like my brazenness, the bold way I insisted I would stay but he had shades of an English gent and knew he couldn’t really throw me out without being a complete cunt and in fairness, desperate as I was, I was a nice enough girl. So I waited it out. I can’t have been that bad though because he only attended for an hour and a half (or maybe he was concerned I was going to ransack the room) and then returned back to the hotel for a little more.

Once the bratwurst was standing too attention it was all stations go. I rolled out a variety of positions from missionary, doggy style, cowgirl, reverse cowgirl, sultry saddle, the squat, standing up, legs on shoulders – the lot. He went solid for over three hours. Had I not been so busy trying to manage my exercise induced asthma I’d have applauded his stamina. He’d put most young men to shame with his solid shafting of me. I could feel my vagina lips puffing with each pump. Changing positions in an attempt to generate a splurge of semen within me became chore-ish. To have him re-enter my swollen labia was excruciating. As he banged away like a pneumatic drill for twenty minutes all I could do was go through my mind’s catalogue of sexual positions in a bid to find the right one to generate his orgasm and resolve myself to the fact that I would have to endure another penetration from his pepper-mill when it was time for a position changeover.

I can’t tell you the climax of my imaginative and acrobatic workout. I certainly didn’t climax and to my shame, despite being less than half his age I fell asleep mid fuck and thus couldn’t possibly comment on whether he did or not. I’m guessing given I didn’t wake entangled with his body or snuggled against him, that I wasn’t invited to stay for breakfast, nor did I render an utterance of a goodbye from his state of slumber or even a thank you text the following day he didn’t attain the desired pinnacle from his unwelcome overnight guest at the Ritz. He really should’ve saved me for an illicit encounter at the Travelodge – bad judgement on his part

* His name was Steve not George, I just thought Granddad George sounded funnier.