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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.
But wait!
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? Part 2 (Fu*king A Grandfather With A Hip Replacement)
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.
Over the course of the night I learnt a few facts about Mike.
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.
One Woman One Hundred Dicks 