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This is a question Cougars and Sugar Daddies

Tell us your stories of age gap shags. No paedo gags please.

Inspired by The Resident Loon

(, Thu 4 Dec 2008, 13:55)
Pages: Latest, 14, 13, 12, 11, 10, ... 6, 5, 4, 3, 2, 1

This question is now closed.

When
I was 16, my 18 year old boyfriend left me for a 13 year old. I didn't think that was half as outrageous then as I do now.
(, Thu 4 Dec 2008, 17:35, 5 replies)
Well, my dog is well over 70 in dog years
etc

On a serious note; I have never had sexual relations with anyone who was more than a year older or younger than me. I think that, in today's modern world, that is abnormal enough to mention. Thus, my story about age-gap shags is; I haven't had one and everyone else has.
(, Thu 4 Dec 2008, 17:32, Reply)
I was dumped
for being 2 months younger than his sister. He was 17, I was 15 but turned 16 while we were going out - how is that fair?
(, Thu 4 Dec 2008, 17:31, 1 reply)
Almost?
Back when I was 17 there was a lady of 28 who was making it plainly obvious she wanted me to give her trip to averagetown (I'm not one to blow my own trumpet, if I could I'd never have time to do anything other than that)

Plainly obvious to everyone.

Except me.

I thought she was just being friendly because I coached her sons football team.

I took the time she kissed me softly on the neck at a presentation evening as a missed kiss on the cheek because she was drunk.

I wish I could go back in time and kick my 17 year old self, squarely in the bollocks.

This one probably could have fit into last weeks too. Oh how I hate how blind I was when I was younger!
(, Thu 4 Dec 2008, 17:22, Reply)
In which a young Chickenlady gets chatted up by an older man
Many, many years ago when I was a fresh faced undergraduate my best friend Shell asked me to go with her to a concert at Wembley.

I'd never been to Wembley before so I was quite keen on seeing someone well known and undoubtedly brilliant there.

Shell was one of my 'cooler' friends - she knew all the words to every Smiths song and could recite most of the works of Sylvia Plath. Shell was cool and miserable - an undergraduate Norway if you like.

That's why it came as a huge shock when red-faced and rather sheepish she told me the concert at Wembley was…

Jason Donovan

I know, I should have put this in last week's QOTW.

Anyway, after I'd stopped laughing at Shell and her crap taste in music (this was a long time ago and I can't really criticise her - I've got both James Blunt albums) I agreed to go just for the experience of seeing a big concert gig rather than the little ones I was used to - mainly at the Margate Wintergardens - classy.

I drove Shell and a couple of other student mates up to London. We parked at Anna's house - Anna was a maths undergrad and had more facial hair than any of the lads in her year, but could always be relied upon for a good laugh.

After a long journey we arrived at the stadium and finally found our seats.
I was at the end of our small group of four or five so I had to sit next to a stranger.

The entire place was packed with raging oestrogen, Clearasil fumes and an undertone of squeaky clean sexuality not seen since the last Cliff Richard tour.

Next to me was a father with two young daughter who looked around ten or twelve years old. They jumped up and down in their hard orange plastic seats which clashed with their bubblegum pink ra-ra skirts. Their father sighed heavily and glanced over at the group of beguiling women sitting next to him.

I smiled sympathetically - although a few years off producing my own offspring I was fairly tolerant not least of all because a)this was a Jason Donovan concert and b)I was part of the way through training to be a primary school teacher at the time and it's sort of in the contract that you really ought to tolerate kids.

He took this sympathetic smile as a come on.

He shifted in his seat and angled himself towards me.

I was very flattered - this was a handsome older man, why, he must have been at least thirty-five!

We chatted about how busy it was, how many kids were there, how both of us weren't really Jason Donovan fans, how we'd both come for the sake of others - he his daughters, me my friend.

We laughed politely.

Hmm…this could have potential…. I thought.

He smiled at me.

He complemented me on my outfit (jeans and a t-shirt I think).

He smiled again.

I smiled.

We both smiled.

FFS! Get on with the story about how it turns into shagging!

Then he leaned forward and said, "Music was much better when we were kids, wasn't it?"

"Of course!" I replied and I grinned knowing that this would flatter him.

"So" he said, "Do you remember where you were when the Beatles split up?"

…..


…..


…..

"Erm….I don't think I'd been born."




He nodded and turned back to his daughters.

I turned back to Shell and Anna and made a mental note to buy industrial quantities of anti-aging creams.
(, Thu 4 Dec 2008, 17:18, 8 replies)
19 na, na,na,na,na,na,na,na,na,na,na,na, 19
I’ve mentioned in the past that my marriage has come to an end, and I now find myself at the dawn of a new life.

At the moment, I’m completely skint, living in a small bedsit that I’m renting, whilst also paying towards the mortgage on the house I lived in with my (soon to be) ex wife.

This leaves very little money to socialise, in fact, even if I don’t eat, drink or put petrol in my car, I’ve spent my entire salary on direct debits before I start.

This has meant I’ve needed to make some changes as in a small bedsit (no room for a sofa, its get home from work, sit on bed, cook dinner on a 2 ring-hob, eat it – sitting on the bed – watch telly – sitting on the bed, make a phone call – sitting on the bed….. (I’m sure you get the idea) its very easy to go out of your mind with boredom.

Now, bless my friends, they’ve all been fantastic these last few months, inviting me over for Christmas, cooking me dinner and even taking me to the pub for evenings and paying for me to get drunk (and I love them all so much for that).

But I knew that this wasn’t going to help me in the mid-term, and so I took a job in a pub. I’ve got no experience of working in pubs – but a lot of experience drinking in them.

Anyway, I’d been working there for 2 or 3 days and was starting to get the hang of it (I was employed on a ‘have a couple of shifts and we’ll see if it works out’ approach), certainly, I was pouring pints with aplomb and getting the drinks order right, first time, every time. I am actually a good barman, having banter with the customers and making new patrons feel at home and giving them some welcoming small talk

It’s this that has led to a dalliance I would normally have refused as the lady in question is younger than me, by some margin. I am, for the record in my mid/late 30’s, the lady who made me the object of her desire was, I later found out, 19.

19

19 and gorgeous, funny, witting confident and above everything else, showing little ‘ole me some attention. I never get attention when I go out, largely down to the fact that on the rare occasion I do go out, it’s with friends and I don’t want to ignore them over trying to get my end-away.

The attention I received was ‘flirting of the highest order’ (well, it was to me anyway), she came to the pub on her own (a rare trait and one that should be encouraged in my book. She sat at the bar and she drank either JD and ginger ale or gin and tonic. Every 2 or 3 drinks, she’d say ‘get yourself one’ and I’d always reply with ‘I’m not suppose to drink when I’m working, I’ll have it later on if that’s ok?’

We get more confident with each other and I start to flirt back

She says, ‘I’m not buying you anymore drinks, I never see you drink anything’ (and the reality is, I was taking the cash as a tip – having rung a half-pint of fosters in the till, I need the money).

I reply with, ‘I finish at 11, why don’t we go somewhere else and I’ll buy you a drink?’ – a really bold move on my part as I’ve got about fifteen quid to last me until ‘forever’

Which is completely out of character for me, I can’t speak to women usually.

She agrees.

We go out, we have a couple of drinks and then we get to the end of the night.

We kiss, it lasts for ages, I can taste the JD on her lips and the smell of Marly lights on her breath. I don’t know why, but that combination really works for me.

Anyway she says ‘Can I come back to yours?’ – Now, I was more than a little reluctant to allow that, seeing as I’m living in squalor at present and whilst I can’t see anything coming from this brief interlude with the beautiful 19 year-old, I don’t want to miss out on breaking my ‘very-much-single-duck’ - and lets be honest, she’s absolutely lovely .

Then I remember, my ex-wife is away and will be for the next few days (she’d asked me to look after the dog, but I am not able to have animals in the bedsit). So, using the key I still have for my old house (I insisted on keeping a key whilst I am paying towards the mortgage), I decided in my infinite wisdom to go there for the night.

Since moving out of the house, things have changed there. I (wrongly) assumed that when I moved out, the house would have stayed the same, bar the things I took. What I didn’t bank on, was the new ‘squeeze’ on my soon-to-be-ex-wife being in the house, looking after MY dog and watching MY telly whilst sitting in MY chair.

We exchanged ‘frosty’ welcomes and I say, ‘I’m staying the night’ to which he replies ‘fair enough, it’s your gaff – what room are you using?’

So there we have it, I had a one-night-stand in the house I use to share with my wife, in the bed I used during the happier times with my soon-to-be-ex-wife, whilst my wife’s ‘lover’ sat down stairs so as not to disturb me (which I thought was jolly decent of him). The sex was amazing, the sheets were a state (and I wasn’t going to wash ‘em) and I’d had a all-to-brief fling with a lady much younger than me.

My soon-to-be-ex-wife’s reaction when she found out?

SHE HIT THE ROOF WITH ME, WITH HER NEW BLOKE, WITH THE DOG, WITH EVERYONE. At one point, she was going to call the police and have me arrested for ‘breaking and entering’ (She was advised not to do that be everyone, seeing as I own half the house, pay had the mortgage and all that malarkey.

Sadly, the complications of the location and the situation means my beautiful 19 year old has decided (quite rightly I fear), that I’ve got too much baggage and we aren’t able to see each other anymore.

I hope she’s telling the truth and it’s not because I misheard her when we were having sex and I thought she said, ‘cum on my face’ whereas she was actually saying ‘ its-not-a-race’ or that I’m rubbish between the sheets and the very thought of being intimate with me again makes her want to vomit.

Apologies for the lack of humour and the length, I’m not a very funny individual.

Mullered, skint, single and rubbish.
(, Thu 4 Dec 2008, 17:17, 8 replies)
More wrinkles than Yodas bawbag.....
In my younger days I was targeted by a woman in her late forties/early fifties in the pub and dragged back to her place with the promise of more booze.

After a couple more drinks she put on a porno and wanted to watch it while I took her from behind. That sounded all right to me so that's exactly what we did.

As we were getting it on I became aware that we weren't alone so I turned round and locked eyes with an old bloke standing in the doorway in his pyjamas watching me giving it to his wife.

I pull out and say 'erm......'

She turns round sees her husband standing there and shouts 'Hey what have I fucking told you, get the fuck back up the stairs till I'm finished'.

Off he goes, like a chastised puppy while she's kneeling there, arse in the air ranting about what a useless, spineless bastard he is and I'm left wondering how quickly I can get out of there and if this is the night he's going to finally snap.
(, Thu 4 Dec 2008, 17:15, 1 reply)
I'll just pearoast this here then....
Back when I was 16, I was up at the Edinburgh festival. I'd met a few techie types whilst doing work experience, and ended up meeting most of the comedy circuit at the time. It was fucking great, going to every house party and being plied with all sorts of booze and narcotics. And then I met Mick.

He'd sat down next to me in a bar, and we had instantly clicked. You know how you just start talking to someone and everything else melts away? Well, tht was the two of us. Only one small slight issue- he was 38. But we were mates instantly, and that was all that mattered. We spent the next week glued together at every party.

At the end of our week together, I was trying to shake off a bloke who I'd snogged drunkenly earlier on and who was telling anyone who listened I was his girlfriend, and Mick was being persued by some blond thing who was adamant that he was the one for her. He'd tried to get her into a quiet corner to tell her about his (fictional) wife and three kids, but she pulled him into a toilet cubicle. After shouting for the bouncer, the two of us legged it.

We went to another bar until we were kicked out at 4am. I had a train home later that day, so we walked arm in arm around the city, just talking (still just mates here). After a few hours, he asked me if I fancied him.

"Fuck" thinks I, stupid 16 year old me has ballsed up this friendship. Because I had fallen for him so hard over the last week. I hadn't even thought I was capable of feeling this much about a single human being. And I was doing my damndest not to show it to this incredible man, because with a 22 year age gap we couldn't honestly be more than mates, right?

However, I make a point not to lie. "um, kinda" I saucily replied.

"Good. Then I guess we can be mates that fancy each other then"

(Bear with the flirting, neither of us are any bloody good at it. I still have no idea whatsoever if someone's interested in me)

We had a coffee. We walked down to the meadows and lay on the grass, and watched as the sun rose. And then we leaned towards each other and had the shyest, most gentle kiss ever.

From that day we have been inseperable. I was still at school- I had to deal with having a boyfriend older than some of the teachers, he had to deal with every one of his mates asking what the hell he was playing at. But we've stuck with each other, because there is no way I can be without him. When we're apart, it hurts so much. I never knew that I could feel so much for someone that just lying next to him would make me gasp with the swell of emotion. He's my best mate, my rock, and the best fucking lover in the whole damn world.

We've been together for over 5 years now. We've been living together for almost the same amount of time. We worked together for 3 years so that we would never be apart, and now we both work from home together. Every day I look at him and feel more in love with him, and he tells me the same all the time. We honestly can't go more than a day apart before rushing into each other's arms again. We have no secrets.

Regardless of other people's judgements, follow your heart. Because 5 years ago we knew this wasn't some simple "lets be together because we're bored". There is no way I'd be in a relationship with this age gap if I had any choice, but that's what Mick is, and I love the wisdom he brings to me, and he loves the clarity I give to him.

And he still keeps me up til 3 every night :D
(, Thu 4 Dec 2008, 17:13, 8 replies)
heh.
i was fifteen but i looked eighteen, i could get into most off liscences without any hassle. This made me very popular amongst my peers. oh yeas i was the king of the park. breezers for all. more breezers than those pathetic minded fools could handle. the police came, this was inevitable. I was caged, this would have saddened me if i felt emotion like most people seem to (i have trouble empathising with people. sometimes i wonder. i wonder aloud. aspergers? you may mock but i can't feel for you. i hope you understand my rhetoric.)

I was let go with a caution and the news of my exploits spread. suddenly i was cool with the sixth formers (not that i am bothered by your bourgieous notions of 'cool' ("glomp me!" t-shirtsFTW!)) we ended up at a student real university stundets party one saturday night. this was good. i was there with my booze and i saw her. i stealthily approached her at an angle where she couldn't see me. i noticed her drink was low. i comprehended she would need a refill. i moved. into the kitchen. breezers - where were my breezers. i did not panic but moved with assured speed - i had timed it perfectly. as she finished her cranberry and raspberry breezer another slotted into her hadn. "i saw you were low" i said staring into her eyes. she blinked. blinked again. 'sorry, who are you?' our eyes met. she must have been at least 22. a goddess. i explained who i was - but the reptilain part of my brain screamed don't let her know your age! the way she smoked her benson made feel like one day i could experience emotions like 'everyone else'. i made an offhand comment about the otaku blog i make (i am a regular and avid blogger. blogspot. blogger. livejournal. i cross many mediums)she laughed. our hands touched and as the ace of bass pounding throught he flat reaches a crescendo we fall into each other. like a daydream or a fever (postrock. love it. makes me feel like i'm the only one on earth)

heh.
i'm not one to kiss and tell, but, internet, lets just say while she came she licked my eyeball.
(, Thu 4 Dec 2008, 17:10, 5 replies)
There are few stories I can relay this week
which do not begin with the words "My mate Stuart and this old dear....", as I have a friend who is becoming a bit of a granny grabber. However, the one tale I do have is quite tenuous at best, although it sort of fits both this week and last weeks questions, so you'll have to bear with me.

A few short weeks ago, myself and a few friends travelled to Edinburgh to watch Scotland's rugby team put up an epic performance against the South Africans, almost beating the best country in the world! The day went well, we had a few nice chats with some South African supporters, not like football where we'd all have been hurling molotov cocktails at each other.

The game finished, we had lost. My mates were all pretty drunk by now, but I haven't been feeling too well recently so had only had a single pint. We staggered off, had a steak dinner and ended up in some swanky Edinburgh bar. After being forcibly removed from some reserved seats, all the while going "ooooooh re-SERRRR-ved!", we found some more reserved seats, scrunched up the reserved sign and settled in. I was dressed like a tramp compared to the suited and booted clientelle and felt a trifle uncomfortable, so I discarded my scotland cowboy hat and decided drink was the answer. We all trotted off to the bar and stumbled upon possibly the most beautiful sight my eyes have ever beheld.

There she stood. About my height. five foot seven since you ask, long blonde hair, perfect curved figure wrapped in a tight short black dress. I only saw her from the back at first but was instantly struck dumb. I came to my senses with my friend shouting "What do you want?" at me and pointing at the bar, and for some reason, shy little me nodded in her direction and said, rather louder than I had intended to, "her". She heard me. She turned, her beautiful face even more stunning than I had expected, and giggled at me. For some reason, the usual shameful feeling of being a tiny slug in the glow of a huge sun did not appear, despite the fact I was still mostly sober. She was in her early twenties, and she gave me a little knowing look and a smile that would melt ice.

My friend returned to the task of buying drinks and she had again turned to face the bar. Thinking my brush with beauty over, I started talking to my other friend, who stands a good 8 inches taller than me, and said "You know, I think I'll go into hospital and get my legs broke and reset, you know, so I can be taller!" Quick as a flash, this beautiful creature spun round and said "Oooooh, I'd love to do that as well I hate being short!"

She's. Speaking. To. Me.

My mind tried desperately to pull up from the deathspin it had just gone into. I have to find words, ANY words just so long as they aren't crushingly embarrassing. "You aren't short though, not for a girl" I managed, trying to sound as flattering as a half melted slug can. She then kicked off one shoe and stepped down to her true height of around five foot two. Which as everyone knows, is just perfection.

I was in love.

"Wow" I gasped. "How big are those heels?" She stooped and presented me with her shoe. I fought the urge to dash off into the night with it. I also realised that giving it a huge comedy sniff was probably not going to go down well. I settled on stating that I had a similar pair at home but not in that colour, and she giggled. This is amazing! I am speaking to a stunner and I haven't caught fire yet. My mate then attempted to sabotage me by saying he could smell feet, but even that didn't work, nothing could stop the events that were unfolding. I had met the future Mrs. Bag and nobody could.....

"'Scuse me, mate". A shoulder scraped along my face and I found myself eyeball to neck with someone. Some escapee from the local old folks home had stolen a suit and wandered in. But what's this? He's kissing MY FUTURE WIFE? The man must have been all of 55. He turned with her waist held firmly in his grasp, expensive suit wafting stylish cologne in my face. He gave me a slightly smug look and walked off with my future in his arms. The bastard.

It gave me hope though. If I can somehow afford an expensive suit and a sports car, it won't matter how old I get. the man looked like Ronnie Wood's grampa.
(, Thu 4 Dec 2008, 17:07, Reply)
What do you think of the QOTW so far?

(, Thu 4 Dec 2008, 17:00, 12 replies)
He's 7 years older than me
and a fellow b3tan, in fact I met him on here (awww....). I'm 20, he's 27. He's amazing, wouldn't swap him for a younger model for the world. Especially after last night ;)
(, Thu 4 Dec 2008, 17:00, 1 reply)
Honestly, this isn't about me....
I worked with a young guy, younger than me, and during quiet spells we would regale each other with tales of excess and stupidity. Within a few days it became apparent that he liked the company of older woman........much older.........as old as possible. He wasn't a bad looking guy and probably would have had no trouble obtaining some youthful snatch.

Anyway, after several tales of granny grabbing and what not and him wanking over the 70 year old woman who lived next door....he came out with a tale that defied comprehension, but to be honest i believed every word.

On pulling some 50+ horror bag at the local meat market, he heads back to hers to consummate their undying lust. Whilst there the talk turns to fantasies...She asks him his and he tells her he would love to piss all over someone.....so she pops herself in the bath and he duly drapes her with his golden rope. Much to her delight i may add, even so much as she slaked her thirst with a few mouthfuls of his essence.

Then its her turn...she confides that is has always been her fantasy to suck a guy off while she is having a shit. Yes, you did read that correct. So, being the dashing young gent that he is, and not one to renege on a deal, he obliges. So its a short stagger from the bath to the throne, where she assumes the position. She starts to gobble his pissy fuck stick with much vigour, and by all accounts he's enjoying it....then the straining begins and she delivers a brown trout into the bog. He is still enjoying the moment until that is the smell wafts up from between her legs and immediately turns his ardour to dust.

He withdrew his limp cock and made straight for the exit, via his clothes.

The dirty cunt then confessed that he actually liked the whole episode and was keeping his eye out for her whenever he went out.....

Sweet Jesus
(, Thu 4 Dec 2008, 16:53, 3 replies)
I was barely an hour old.
She was in her late 30's.

I was her painful dildo for almost 4 hours while several people watched on and to this day I feel used.
(, Thu 4 Dec 2008, 16:44, 7 replies)
I have always been with younger women
and to be honest I've yet to have a girlfriend who isn't a withering ball of angst, self doubt, jealousy, immaturity and negative body images.

In the four serious relationships I've had in my life:

I've had a girlfriend who discovered mid-relationship that men will usually be nice to you if you sleep with them or at least give the impression you will. (Boyfriends don't like it though).

Ive had a girlfriend who shouted at me for watching the half-time cheer-leading routine at a rugby match, and once berated me for flicking through a copy of 'nuts' that was sitting about, because she was so insecure.

Ive had a girlfriend who refused to have sex in any other position than missionary with the lights off because she was a bit chubby. The one time she went on top she got upset because I didnt come quickly.

Ive had a girlfriend who is so clingy she would talk at me for hours (often about how fat she was and that she was sorry she wasn't perfect for me) just to keep me on the phone. She would often cry when I tried to get off it.

If it wasn't for the fact all these lovely ladies (minus 'missionary girl') were dirty, flexible, hot, tight and impressionable you could say my love life was an epic fail.
(, Thu 4 Dec 2008, 16:39, 11 replies)
On some of...
...the less respectable gay social networking (read: man-on-man shag-finder) sites I've frequented on occasion, numerous were the teenage lads asking if I wanted to be thier Daddy.

For reference, I'm 36, fairly well put-together with a goatee (that's goatEE, as in beard, not the similarly-named hula-hoop-for-an-anus thing - I may be a gayer, but please, I'm not that extreme), a touch of grey at the temples and a not-camp demeanour. It seems that to some this constitutes Daddy material, though I'd normally peg a bear-type* as a shoe-in for that kind of role. A matter of perspective, I guess.

I've even had such offers on nights out as well. Both these and the internetty ones were knocked back though, essentially because I learned fairly early on that teenage lads are a) mostly fucking idiots and b) mostly a shit shag for lack of experience. Hell, I mostly found that to be true for lads under 25, let alone teenagers - I know I was back then. I just can't be arsed sorting the wheat from the chaff, you see. I've said before that there's nothing so overrated as a bad fuck - these days it's about quality rather than quantity.

Teenagers in particular also have no idea at all how things are done. One lad I chatted to online for awhile, after revealing that he was 15, not 24 suggested that I travel to the other end of the country where he lived and rent a hotel room in the town. Once there, he would visit me in the evening to (in his own words) 'do me', probably quite badly, then get back home before his parents reported him missing. He was markedly put-out by my bemused rebuttal. I'd need some convincing even if I was sure that it was going to be the lay of my life, let alone some brat's first time.

*And I mean a PROPER bear with some muscle to him, not just some mid-50's fat hairy fucker squeezed into a pair of chaps.
(, Thu 4 Dec 2008, 16:38, 4 replies)
Confusion
I was (and still am) painfully shy, especially when it comes to "the hunt" as it were.

As a result, most of my "conquests" have been female-initiated.

This would also go some way to explaining why I was still virginal at 21, post-University.

So, anyhow, back in the hometown & living with mates (as in www.b3ta.com/questions/cringe/post313949) and we are out on the town.

Well I spot a woman who is still looking good for her age & give her the eye as I walk to the bog. On my way back she ensures she strikes up a conversation. One thing leads to another & we share a cab back, but nowt happens.

We arrange to meet on the Friday. Turns out she is 41, 20 years my senior, but I reckon I'm in with a chance of discarding the v-plates here, so fuck it...

Friday night drinkies, we end up back at mine. Still nowt.

She comes round early the next week, and this is it.

As a precursor to the point of the story, in my eagerness to gain info, I had spoken to more experienced mates. "When you are shagging, get here to stick her finger up your arse just before you come & you'll shoot it miles"

So she talks me into sex with the immortal line "Well it's about time you filled her up" (well she WAS from Derby).

Not a great deal of time later she is astride me & I remember the sage advice given to me by my mates.

Her face did change a bit, as I rammed MY finger up HER arse whilst approaching climax. But give to give her credit, she didn't complain.

My excuse is that I got confused.
(, Thu 4 Dec 2008, 16:33, Reply)
@ Baldmonkey Et al
Didn't any of you see last months QOTW? That was pretty inspired and very funny.

Although if you didn't appreciate it or like it then Don't read it and fuck off...

Although I do think your story lost a bit of the humour after you quickly deleted it...
(, Thu 4 Dec 2008, 16:26, 18 replies)
I wanked into a pair of boxer shorts....
then left them behind my bed for 20 years and then wanked into them again.
(, Thu 4 Dec 2008, 16:25, 4 replies)
The Miami Actress. Part I
Miami Actress was 13 years older than me when I met her in the summer of 2001 (and presumably still is).

Miami Actress was the seediest, funniest, drunkenest, dirtiest, most talented(est) way I could ever have wished for to get over a very severe break-up.

I’d been moping around London since my engagement broke off in January, I was depressed, going nowhere, hating my life and I knew I needed to do something before I spiralled out of control, so I booked a flight, a hire car and one nights accommodation and headed to Miami to see where the wind would take me.

It took me to a woman who I will always cherish for bringing me back to life in her own inimitable way.

Her inimitable way was alcohol, sex, theatre, food and nudist beaches.

Or any combination of the above.

I guess I’ll start with how we met.

On Duval Street, on my third and, I’d decided, final night in Key West. (I decided that after too many strip clubs, too much weed and booze and too many ‘eccentric individuals’ that I better go somewhere more relaxing before I died).

I was walking back to my hotel, when she came out of a restaurant, waving excited goodbyes to the people she had been with.

I knew I wanted to talk to her, so I pretended I was lost (smooth, huh?).

We walked.

We talked.

She said she was an actress. I said that meant she was a stripper. She snorted.

We ended up in my room.

Cut to:

Dennys. Next Morning.

She’d been back to her hotel after our night together. I assumed we were saying goodbye until she said ‘Meet me at Denny’s’ in an hour.

I waited with a coffee wondering what I was doing, she wasn’t coming back and I wasn’t sure I wanted her too.

And then the door burst open and in she flew.

She threw a theatre ticket at me.

She told me she wanted to prove she was an actress and I was to go to her show that night.

I told her I had checked out of the hotel.

She’d remembered.

She told me I was staying with her. And gave me her room key.

So I moved in.
(, Thu 4 Dec 2008, 16:23, 5 replies)
This should have been
in last week's "cringe" QoTW as it makes me cringe now to think of it more than any of my responses to that question...

Anyway.

Getting married far too young - at my graduation I was the only one with baby buggy in tow - meant that post the inevitable quick separation, I tended to go for older women. Women in their early 20s and I had nothing in common, or so it seemed.

Several years after graduating, in my second job, I was unhappily living with someone around 8 years older than me. But the story isn't about her.

Two years into the job I had at the time, a new colleague came to join the small office I worked in. She was a good 20 years older than me, and she was Not A Looker. At all. She wasn't fat, but she was:

- short;
- a redhead, but not in the "flowing auburn locks" way but more like a Chuckle Brother or a Chuckie doll;
- wearing thick bottle-topped glasses;
- with copious lines on her face - it could have doubled as a contour map of a particularly steep hill;
- with a personality best described as "strange".

We worked together for a small charity. One year, we got a free stand at the Boat Show at Earls Court. We had a rota system for covering the stand between the handful of staff we could spare. Because of the distance between where we worked and London, we were put up in a hotel.

In my defence, I blame this on my boss. Both I and my female colleague - let's call her Andrea, for the sake of argument - were "covering" on the Sunday. So we were to stay at the hotel on the Saturday night.

Previously, my male boss and another employee, also male, had been sharing the same twin-bedded room. Somehow, this was meant to be acceptable for me (male) and Andrea to share.

Yes, you can guess what happened. Oh dear oh dear oh dear. My defence is / was not much sexual experience, alcohol, a brazen and successful attempt by Andrea to seduce me, and going through a bad patch (sleeping on a friend's sofa) with the on/off girlfriend at the time.

But that's not the cringe-worthy bit. Enough that I slept with one of the extras off Lord of the Rings, but worse was that I:

- repeated the performance sober at her house some days later;
- then got her to drive me the 50 miles or so to where my girlfriend lived so I could get back with her.

Lord, forgive me for this and please God don't let my current girlfriend, soon to be wife (this Saturday, dudes !) read this.

Funnily enough, whenever in the past I have added up my "shags", I always forget to add Andrea to the list.

The shame - the horror.
(, Thu 4 Dec 2008, 16:21, Reply)
The whites of their miserable eggs (fetch the muumuu)
Let me introduce a past relationship of mine. It was this. Its probably why I am slightly edgy and nervous all the time.

When I was 16, I first used the internet. Naturally I never used it for the purpose I had sold to my parents, i.e. ‘homework’ and ‘research’. I used chatrooms. More specifically, AOL chatrooms.

It was absolutely amazing. I was free to do and say what I wanted (this was before the internet became a haven for viagra ad-serving bots). I chatted merrily away, staying up all night at the weekend, making friends, and having a good time.

Then I met the perfect girl for me. American Nancy. My sweet Nancy. From Columbus, Ohio. Cheerleader (so same age as me-ish), and writer. Blonde as apple pie etc etc. We used to write emails to each other all the time and chat until the wee hours. I didn’t even know anyone with a scanner and I am fairly sure that digital cameras weren’t available in the single mega pixel form for under £1000 for a few years yet, so it took me ages to arrange a badly scanned picture of myself to send to her. (by asking my dad to arrange it with the IT department where he worked).

She sent me one back of her year book picture. She wasn’t as bad looking as I expected actually, half believe my teasing friends about what a girl on the internet would look like. She was blonde, but a bit plain looking, and wearing a decidedly old fashioned dress that looked a bit like a re-utilised curtain. Still she was ‘glamorous’ (in my eyes) and really nice to communicate with.

We started to call each other. She sounded a bit husky if I am honest, but I didn’t mind. She spoke with an impossibly nasal accent but hey, she was glamorous and American, right?

Anyway, I saved up some money to go and visit her. She had a car and those impossible freedoms that Americans in my mind had, like a phone in her room and her own credit card from her dad. I had a rusty bike, a service till card (£50 limit!), and a house phone in our kitchen so it was natural that I go to her. If someone called, then my mum would inevitably answer and screech upstairs that someone was on the phone and could I please not be too long *this* time because dinner was almost ready and I should prepare myself to eat *all* the cauliflower cheese, all in full hearing range of the phone receiver. (Some of my various nemeses used to call me up just to listen to my mum squawking so they could have some fresh ammunition at school)

So I flew to Newark from Heathrow my heart full to bursting with hope. Newark was a scary place. From there I flew to Columbus, and then I had to take a short bus to a little place called Dublin, where she actually lived. I stepped off the bus and I suddenly wasn’t tired anymore, I was excited once again! Then! I spotted Nancy’s obese mum! I could see the resemblance, and she was waving at me from the sit down bit in the bus stop. I grabbed my luggage and dashed over, surmising in my mind that Nancy must be in the toilet or something.

Then Nancy’s mum started to hug me closely. She had bloodshot eyes. Attentive readers will of course have realised several paragraphs earlier the outcome.

To be completely fair she was only 26 but unfortunately she had let herself go a bit from her high school days and looked a lot older and sadly wider. Wiiiider. She was wearing a muumuu. (I didn’t know what one of those was of course at the time and I thought it was a big dress, which kind of what it is anyway)

I was a bit shellshocked and frightened and she saw that and she immediately went off on one and said that she was sorry and she really liked me but didn’t want to scare me off, and wasn’t it swell that I had come to visit and she wanted me to visit her parents and she could drive us there it was only 7 hours drive. I couldn’t really get a word in edgeways.

But that’s because I was shit scared.

So I smiled and was nice, and kissed her, and ate her less than nutritionally adequate meals. She seemed to think that frying some hamburger meat in a ‘skillet’, adding some powder from a box, and shit loads of processed cheese slices was the height of haute cuisine.

The two weeks passed in a bit of a blur and I couldn’t tell my parents properly what happened because whenever I rang them, she was always close by listening. I swear to god that I can never get past the first 20 minutes of the movie Misery because it really messes me up.

Anyway I came home. As soon as I got past customs I started crying because I was so happy. Newark Airport seemed like Eden (if you’ve ever been to Newark then you know how I felt).

When I got home I was so happy and relieved. I didn’t tell my parents, and I didn’t use a chatroom for about a week after.

When I told my friends the story, they all were like whoah! You should have called the police but weirdly she was still the person who I bonded with in the chatrooms, even if she lied to me.

Now I have to see the whites of their eggs before they can have a relationship with me.
(, Thu 4 Dec 2008, 16:19, 3 replies)
Granny Sue
Thought I would start off my weeks replies with a story of my ex-housemate Rob that happened when we were 20.

Rob was a very strange human being with minimal regard towards his physical appearance, general cleanliness and body odour. Despite this Rob would regularly manage to bring a women back to our house most weekends. True most of these women weren’t the best of lookers and were also pretty desperate for some sexytime. Rob didn’t care what they looked like and lived by the motto that “any hole is a goal”.

One Friday night he returned home with a women called Sue, aged 58 who looked a lot older (To give you a mental picture, she looked like Mummra’s older sister). Anywhoo, he went back to his room for some fun while I went to mine and turned on the TV to drown out the sounds of his granny lovemaking (She was a Grandma, she showed me the pictures of the grandkids during the taxi ride back from the club). The noise from Dial a date successfully drowned out the sounds and I passed out. Until my bladder was full and woke me up.

I turned off the TV and as I passed Robs room on the way to the loo I heard him snoring so I was saved from hearing anything. I emptied my bladder, and returned to my room . Its at this point that I managed to bump into Sue who was also in the process of nipping to the toilet while wearing one of MY football shirts and nothing else. The problem was twofold. One was that the shirt she was wearing wasn’t long enough so I was treated to the sight of her naked bottom half, the second problem was that it had started to get light outside (It was summer) So I got to see everything in detail. My brain failed at this point and all I stood there looking shocked.

Sue: Hiya you ok?

Me: (Barely able to register anything else) That’s my shirt you’re wearing

Sue: Yeah I know Rob said it would be ok for me to wear it tonight, I like to wear something while I sleep.

Me: Thats my shirt

(For no real reason Sue then decides to do a twirl on the spot, God knows why all I realised was that I now had to use the mind bleach to remove the actual sight of her wrinkled ass and decrepit mimsy)

Sue: Don’t you think it looks good on me? I can take it off if you want?

(My subconscious realises that the sight of her shrivelled fun bags would cause me to die from vomiting so it reengages my brain and bodiy movements)

Me: erm....no thanks, bye

(I then sit in my bed and rock back and forth hoping the visions of semi naked Sue leaves my head)

Thankfully Rob didn’t make it a regular thing with her and I gave my football shirt to charity shortly after I got it back.

Sue did return to our house one more time but I think I’ve written enough for now.

Goes to retrieve more mind bleach)
(, Thu 4 Dec 2008, 16:14, Reply)
I managed to fuck a barmaid 17 years my junior once by pretending to like her.
WIN!
(, Thu 4 Dec 2008, 16:11, 5 replies)
For some reason I've ALWAYS been with older women.
My current girlfriend only has 2 weeks on me, but I've had a go on a 36 year old and a 52 year old in my time (I'm 22).
(, Thu 4 Dec 2008, 15:58, Reply)
I was 19
She was 36.

Me and my mates were in a club in Liverpool called The Krazy House. We were very drunk. We had seen this woman who looked much older than the rest of the people in there (the average age in there at that time was probably about 16). My mate bet me £20 I wouldn't try it on with her.

She seemed nice enough, recently divorced, was out without her fella for the first time. I actually really enjoyed talking to her, she was kinda cool.

End of the night rolls around and I've been talking to her all night. My mates have vanished and left me to get a taxi by myself.

She offers me a lift home.

She then suggests we stop at hers on the way. "On the way" turns out to be Chester. She wouldn't take no for an answer. She virually dragged me out of her car and into her house, ripping my clothes off along the way.

At about 11 the next morning, she finally tires of me and kicks me out. I could hardly walk, I was scratched and bitten to shit and I was blistered and bruised in places no man wants to be blistered and bruised. She had forced herself on me maybe a dozen times during the night. She really hurt me.

I loved it...
(, Thu 4 Dec 2008, 15:53, 11 replies)
35 years!
I dated a lovely man when I first got to London. He was fabulush indeed; kind, gentle, witty, intelligent and the sex was so good that I still walk a bit crooked.

I was 21 and could hardly afford to eat. I was doing my best to live a bohemian existence where bohemian = starving and a bit dirty.

He was 56, retired and extraordinarily wealthy. He had a huge house, nice cars and expensive taste in wines.

Now I know what you’re thinking there, kids. But I dumped him when he kept trying to buy me flashy and expensive things. The last straw was a diamond tennis bracelet, I looked at it and immediately equated it to lost sandwiches. I just wanted feeding, maybe sleeping in a building that wasn’t covered in stray pubic hair and dried up snails.
(, Thu 4 Dec 2008, 15:46, 2 replies)

This question is now closed.

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