Breaking In The Forty-Something Near Virgin
In the time honored tradition of the British seaside holiday camps toward the end of every season the ‘talent’ would become somewhat scarce. Good looking men were thin on the ground and finding a decent shag became more of a quest than a game.
My best friend ‘L’ and I would ritually attend the final week of summer season when all the staff at Vauxhall Holiday Park in great Yarmouth would let standards slip with the end of work in sight. When I say standards slip, I don’t just mean the entertainers would lose their gusto on stage and the security guards would be more flexible in letting ‘visitors’ onsite after hours – I mean the staff would stop shagging all the good looking people and happily throw a bone(r) in the direction of the uglies.
But ‘L’ and I were never uglies…there were however years when we (well ‘I’ if I’m being strictly honest) possibly fell in the category of fatties – and no one is ever forgiving if you’ve got a few extra pounds swinging from your hips.
Because of the fact we’d ‘sized up’, ‘L’ and I had to take our nocturnal activities off site and into the pulsating hub of Great Yarmouth town centre; where the locals were far less discerning in selecting their annual summer flings.
‘L’ had picked up a cute impish guy that was totally smitten with her. Unfortunately he was a bit of a damp squib and while easy on the eye his company wasn’t scintillating. ‘L’ insisted I chaperone all dates so that she had someone she could talk to and have a laugh with. Had ‘L’ been a boy or vice versa, there’s no doubt in my mind we’d have ended up together, but our heterosexuality and my nymphomania meant there were times we were forced to separate and hunt out a ‘dick’ for the night.
So it’s a week night out of the summer season in Great Yarmouth and ‘L’ insisted her date take her (with me in tow) to the Pier Bar for karaoke night. ‘L was the most supportive friend. She loved my karaoke. I think she appreciated while I could hold a tune, what I lacked in talent I compensated with passion and performance.
Only recently I was telling my husband how ‘L’ and I did a resounding version of Meatloaf’s ‘Paradise by the Dashboard Light’. My husband asked who sang what part and I looked at him queerly and said ‘I sang the boy and the girl’s part. ‘L’ did backing vocals.
On the night in question with an audience of at least six people I did a stonking version of Will Young’s ‘Who Am I’ which had been an anthem of heartbreak two years earlier on our annual holiday.
When I finished I searched the startled and stunned faces of the audience for a potentially available man. There was only one man in attendance as a singleton. Sure he was close enough in age to be my father, but beggars can’t be choosers.
He won me over instantly with his Geordie accent (Aussie’s love an accent) and went into ‘good impression’ overdrive by complimenting me on my performance – although he was quick to point out it was a boy’s song (we can’t all be sopranos and Leona Lewis!).
What I found particularly endearing about the giant teddy bear was that he was incredibly flattered by my attention.
Want to know why?
Turns out this 47 year old oil rig worker married when he was 19 to a woman eighteen years his senior. That meant his wife’s current age was 65. He was fucking an old age pensioner and he was prime beef.
I won’t lie – the revelation of his marital status was something of a blow. I was determined to get at least one shag by the end of the week and at the moment things weren’t looking good. That I’d invested my time in a dud root was frustrating to say the least.
I had a flash of insight which drew my attention to the fact that I am a sexual predator. If this man did want a liaison, I could be the one to make him take a leap.
I allowed him to buy me alcohol. I laughed like he was Billy Connolly. I listened to him like the words coming from his mouth were said by Jesus himself. I gazed into his eyes like he was George Clooney. I was tactile an overtly affectionate like Jenna Jameson.
He was putty in my hands and as last orders was called and he accepted my offer of an invite back to our caravan.
Moseying along the grass in the moonlight trying to find the number of our caravan in a section where every mobile house looked the same he confided in me that he’d never cheated on his wife. I raised a cynical eyebrow which was unseen by him thanks to the clouds passing the moon. He continued on and informed me that he’d never slept with a woman other than his wife. For any man is reading this – If you think having a near virgin status in your late forties is a turn on or a good ‘pulling’ tactic you would be wrong. Inexperience in your mid-forties is not sexy. The fact that he said it out loud made me believe him which in turn meant he probably wasn’t lying about never having cheated on his wife.
Although the horrid staff on the holiday park had made me feel pretty bad that year about my weight gain, my ego was hugely boosted by the security that my voluptuous curves and ample bosom could tempt a man to stray from his wife of twenty-eight years to see what sex with another woman would be like (reading that back is horrible – how fucked up was I that I thought playing around with a married man for a night was a ‘positive’ thing in my personal and sexual development???)
To avoid having to have sex with her beau, ‘L’ insisted we have the double bed and that her date would be sleeping on the couch. I ushered by prime beef oil rig hunk into the cramped bedroom and offered to get him a drink.
In the time it took me to get a bottle opener and knock the lids off two bottles of Smirnoff Ice he had stripped completely and gotten under the covers. As I breezed in with the two drinks I was greeted by a naked man with the sheets pulled up to his chin.
I have to say I was quite taken aback. Clearly sex was always going to be the end result but a little coy conversation and flirty foreplay never goes amiss. I could literally feel my oriental shaped eyes widen in shock by his brazenness.
‘Toilet’ – was the excuse I offered to remove myself hurriedly from the scene.
I stood outside the door trying to come to grips with things. I didn’t mind a ‘slam-bam-thank you ma’am’ sex session but given his shy and gentle sex life I wasn’t expecting him to be quite so in your face.
He was hunky in a traditional sense. Well over six foot two, short cropped black hair, kind brown eyes, nice lips and a strong jaw on a masculine but gentle face. He wasn’t overly defined in terms of his chest and stomach, but he was solid and firm. No soft bits. The broad chest with a smattering of hair and the muscular arms should have looked inviting, not had me scarpering out like a frightened mouse.
I flushed the toilet and snuck into the living room where ‘L’ and her lovelorn man were chatting quietly.
“I don’t like to bad mouth a guest when they’re in our van,” I said to ‘L’, “but if I didn’t know any better I’d say my gentleman friend is expecting to have sex with me.”
‘L’s beau looked stunned as if I shouldn’t have expected anything else.
“What makes you say that?” asked ‘L’.
“Because in the time it took me to get the drinks he was lying in bed with a massive erection. I know I’m easy but talk about presumptuous. I don’t think he’s left me much wriggle room to play ‘hard to get’ at this late stage in the evening.”
‘L’ rolled around at thought of the massive man, naked on the sheets with his hard on eagerly and unquestioningly awaiting me. ‘L’s man looked decidedly envious knowing he wouldn’t be in any beds with a boner that was inevitable going to be tended to.
Taking a deep breath and rolling my eyes exaggeratedly, I braved the forty-something near-virgin.
I wasn’t in the mood to give oral. I really just wanted to give his cock a mind blowingly good time in my cooch. So I did.
Prior to his bold assumptions about my chastity (a lack thereof), I had every intention of making it a slow, tender affair. Now I just wanted to get it over and done with.
I needn’t have worried too much.
The second I climbed under the sheets with, his heart rate accelerated and he started panting like a thirsty dog. He seemed to delight in stripping my dress from me and letting his hands explore the soft, round flesh of my thighs, bottom and tummy.
When I released my breasts from my favorite diamante wonder-bra he imbibed them as though they were a pair of Big Mac’s on a tray. He didn’t so much as suck my nibbles as mouth my tits and grind his teeth softly on the milky white flesh.
He hadn’t been lying about having only slept with one woman. When I took his hand and placed it between my legs so he could feel the damp crotch of my knickers he moaned and bit his bottom lip as if he were trying to stop himself screaming out in ecstasy.
I could see the warmth wetness of my pussy was too enticing to him explore with his fingers for fear of shooting his load. Taking charge of what might prove to be a rather short affair, I reached down for his cock.
Average in length and girth – which was something of a disappointment given that he was a bear of a man.
He was rock hard and given the number of med in their forties that I’ve bedded, I have to say I was suitably impressed by just how strident and tall his member was. The blood was in full flow because I could feel the pulse of it as I worked the shaft. His teeth were gritted as I spat on my palm and massaged his length. Alight tickle of his balls had him begging me to stop.
Then came the penetration part. ‘L’ knew better than to come a knockin’ because the caravan was clearly a rockin’ with the two of us pleasing plump humans making sweet love in a bedroom with paper thin walls.
He was frozen on the mattress for fear of climaxing before he’d actually got his cock in my cunt. I needed to get laid so ultimately, I was going to have to endure the strain if I was going to get my holiday fuck.
With a mammoth effort I straddled the man and sank easily on his cock. It was a nice secure fit. To guarantee he remembered the ride for good I put my recent pelvic floors exercises to ensure my slit held him tight as I bounced up and down on his dick.
And bounce I did.
I built up such a rhythm and vigor, it was like I was a five year old riding a space hopper for the first time. I was literally rebounding off his pubic mound as I slammed down hard and let my pussy lips feel the graze of his pubic hair. Rising up I took the head right to the end of the slit, but never releasing him. It was only as he started moaning and thrashing on the bed I realized if he’d been married since he was nineteen contraception probably never featured in his sexual repertoire.
I made a time finish by sliding my cunt slowly up his shaft with a final squeeze of my kegal muscles which had him cummign instantly on the outside of my cunt lips and down my inner thighs.
Our farewell was somewhat over the top given our briefer than brief encounter. As he dressed in his jeans and check shirt (I kid you not) for the oil rig and went to head for the docks to catch his boat, I stood on the very tiny verandah and waved him off with all the drama of a wife watching her husband go to war.
Then I went inside and made a weight watchers banana and nutella crumpet.
Then ‘L’ came out and said she had the most awkward night ever trying to keep her horny love puppy at bay while the caravan shuddered on its support structures while I rode the hairy bear to the edge of ecstasy.
It was an awkward breakfast – especially when the horny love puppy shot up sharply when I sat on the sofa to eat my weight watchers banana and nutella crumpet.
How Old Is Too Old For Sex? (Fu*king A Grandfather With Glorious Giant Genitals)
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.
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.