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Girlfriend's Fling With An Older Man
by Lesley (ouirup4it@yahoo.co.uk)

***

My girlfriend is hit on by a co-worker who older than 
her dad but decides to go out on a date with him anyway. 
(M/f-teen, underage, 1st)

***

This is a story my husband wrote about our early times 
together. 

It was 1967. My girlfriend Lesley was seventeen I was 
twenty. We had been going out together for about a year 
and a half, were crazily in love with each other and 
from both being virgins had graduated to full sexual 
activity just around her seventeenth birthday. She had 
the kind of body that stopped blokes in their tracks, 
slim but shapely legs, round but firm backside, a tiny 
waist, 36-A breasts that stood up on their own and 
nipples that invariably indicated it was getting colder 
or betrayed her state of arousal. 

In the looks department she had not been shortchanged 
either. Her long dark hair framed a sultry gypsyish 
face, nose slightly aquiline, small but full lipped 
mouth and dark green 'come to bed' eyes. Some of my 
mates reckoned she looked like Ruth out of Pans People 
but prettier. 

In the decade that launched the mini skirt and the 'see 
thro' blouse, she wore both, and combined with the 
highest boots or heels drew the eyes of the young men 
and set them dribbling. Yet we had no time for anyone 
else, but were consumed with an insatiable passion for 
each other. 

It seemed that we were 'at it' at every opportunity and 
if we had a moment to ourselves it had to be used to 
some sexual purpose. I would meet her off the bus from 
work in the evening and we would drive straight to our 
nearest park up place in a quiet lane or the local 
common where daylight or dark we would be at it 'like 
knives' before breaking off for tea at our respective 
homes.

Collecting her to meet friends at the pub we would take 
up where we left off feeling each other up as we drove. 
Often at her parents, while her mom and dad were in the 
kitchen and we were supposedly watching telly she would 
get my dick out and suck me off, or sit on my lap and 
slip onto me. How we avoided being caught god knows. We 
were experimenting, learning all the time. She had just 
gone on the pill. Our generation was remarkably ignorant 
about sex and even the sex mags of the time were very 
tame.

 You could be forgiven for thinking that women were 
without nipples, pubic hair or any genitalia at all, 
looking at some of them. So everything was gleaned from 
hearsay or dirty conversations and developed by trial 
and error. Very enjoyable it was too. I remember hearing 
some fellow apprentice describing 'licking out' his 
girlfriend and being slightly appalled but sufficiently 
curious to tell Lesley about it. She wanted to try it 
and that summer evening in the lane behind the colliery, 
she orgasmed with such intensity, I thought she was 
having a fit, soaked me and drenched the rear seat well 
of my Ford Anglia. 

Lesley worked as a shorthand typist at a local 
engineering company in Dudley of the type that dominated 
our local landscape at the time. Her job was typing up 
quotations and technical specs for the salesmen and 
engineers. These were a mixed bunch but mostly ex 
drawing office types who had acquired sufficient 
experience etc to put technical specifications together 
and usually in their late thirties or older. 

Not surprising that in such a male dominated 
environment, an attractive young woman had plenty of 
attention. Much of this was of a flirtatious and playful 
nature but being the sixties and somewhat less 
politically correct, at times it often took on a more 
suggestive and titillating tone. Though Les was not the 
only woman in the place she was the youngest and the 
only unmarried female and was the target of most of the 
banter. Needless to say she could hold her own and in 
fact enjoyed the teasing and occasional lewd comment she 
received from the men, many of whom were old enough to 
be her dad.

On a Friday lunchtime it was the custom of the sales 
chaps to go to the local pub for lunch and there was an 
unspoken competition between the blokes to give Les a 
lift. No doubt hoping to get a closer look at her long 
legs or more as she slid in and out of their car. 
Sometimes one or other of the women also went to the pub 
but more often Lesley was on her own with five or six 
chaps. She confessed she enjoyed the way they fussed 
over her and of course they always paid for lunch.
 
One of the senior salesmen a chap called Frank began to 
take a more obvious interest in her. When she had to do 
any paperwork for him, he would always keep her talking, 
steering the conversation inevitably round to sex at 
some juncture or other. 

He was a man of about fifty, married with kids older 
than us, Les told me, as we discussed the day's events 
one evening sitting in our usual quiet lane. She laughed 
as she described how he quizzed her about her sex life, 
and asked what she had or hadn't done. 'He gets all hot 
and bothered when I tell him,' she grinned. Over the 
course of the next few weeks Frank became even more 
solicitous of her company, sometimes just passing as she 
walked to the bus stop from work and stopping to offer a 
lift. 

The conversation would immediately become sexually 
orientated, Frank being complimentary on what she wore 
to the office then asking if she wore a bra that day or 
'had he seen right' when she reached to the filing 
cabinet 'she was wearing pink knickers?' etc. He would 
let her out at the bus stop where I picked her up, 
usually with the comment 'If your boyfriend wants a 
night off you know where to come.'
 
This went on for some months and Les and I laughed a lot 
about 'what a dirty old sod Frank was'. I would 
sometimes suggest she wore a particular skirt or blouse 
for work knowing that it amused both of us that Frank 
was turned on by her, and waited to hear her describe 
his reaction. She climbed out of his car one evening, 
and as she slid into the front seat of mine, began 
giggling. I pulled away enquiring as to the cause of her 
merriment. 

'Frank wants me to meet him for a drink next Friday as 
his wife and kids are away and he has a night on his 
own.' 

'The cheeky bastard' I responded. 'What did he say when 
you told him no?'

'Well I didn't actually say I wouldn't, I was just 
getting out of the car, so I said I'd tell him 
tomorrow.' 

I was nonplussed but said nothing and drove to our 
regular spot on the common. In seconds we were in the 
back of the Anglia and down to our underwear. In between 
tonguing her fanny, I took a breath and commented 'he 
won't just be taking you out for a drink you know, he'll 
be wanting some action'. Pulling my head back to the 
task in hand.

She said, 'I thought I'd just dress up a bit special a 
give him a show, maybe string him along a bit. You know 
like I've been doing at work, perhaps let him have a bit 
of a snog and a feel at the end of the night. I bet he 
don't get much at home and that would probably keep him 
going for weeks.' 

Climbing up her body I slid my cock into her sopping 
cunt and began to fuck her rapidly. She wrapped her legs 
round me and we both climaxed pretty quickly. 'Do you 
really fancy Frank' I joked as we began to get dressed. 
'He's not exactly Stevie Winwood is he?' 

'Well I don't fancy him in a normal way, but I find the 
idea of having sex with an old bloke is for some reason 
exciting.' She said slowly 'You know? Sordid and a bit 
dirty. Anyway, I probably won't go.' 

We didn't talk about Frank anymore that night but after 
I dropped her off and went home to bed I found myself re 
-running our earlier conversation and considering what 
to say to Les. 

To my surprise and disgust I found myself developing the 
scenario between my girlfriend and Frank and jerking 
off. The more intimate and extreme the fantasy became 
the more stimulating I found it. The next evening she 
came home on the bus and I was disappointed. 'No Frank 
tonight' I enquired and tried not to be too inquisitive 
when she explained 'she just hadn't seen him that day'.
 
The weekend came and went without us discussing the 
'Frank,' situation. Then on Monday, although Les came 
home by bus, in the middle of our pre -tea time 
engagement and just as I am mid stroke! She asks 'do you 
think I should go out with Frank on Friday?' I slowed 
down my rhythm and trying to sound as if I had 
considered and thought it through. Said 'If you really 
want to, I won't mind, I know it's just experimenting. 
If you want to, I think you should.' 

After a few seconds she answered carefully. 'He asked me 
again today at lunchtime and I put him off, but I'll 
tell him ok. Tomorrow if you're certain you don't 
mind.'She paused ' But I'm telling him, its only for a 
drink and no funny business.' Over the next couple of 
days the impending date with Frank was uppermost in both 
our thoughts and invaded our every conversation. 
Although Lesley had made a great store of having given 
Frank clear notice of what was to occur, she was clearly 
hugely turned on by the idea of meeting this 'older man' 

He for his part, secure in the promise of a date, had 
eased up on his pursuit of her and had not given her a 
lift or engaged her in too many salacious conversations 
at work. Maybe he didn't want to attract to much 
attention from work colleagues. 

'What should she wear? She asked me, as we discussed her 
'date'. We decided on a white broderie anglaise tunic 
dress that she'd bought from C&A to wear as a blouse but 
which on a couple of occasions she had worn as a mini 
dress. It was pretty see thro' and cinched in with a 
belt just covered her knickers. She wondered whether she 
should wear a slip with the dress but I persuaded her it 
would spoil the effect. 

Underneath she would wear a platform bra she had bought 
from the classifieds in the News of the World, (there 
was no such thing as a Wonder-bra in these days), a 
white G string which she had made herself and Aristoc 
adjustable hold up stockings which I convinced her were 
the trigger to any 'old chaps' gun. They were silky 
smooth and snugged right up into her crotch just on the 
knicker line and just about on the side of decency.
 
Thursday evening when I met her off the bus she said she 
had arranged to meet Frank at a pub a little out of his 
and our area. He didn't want to bump into any work or 
family friends and to be honest neither did Les. So I 
agreed to deliver her to the pub and she said he would 
drop her off at home as it was after dark. 

Later on we sat talking about the next evening and how 
it would go. I joked how Frank would have a heart attack 
when she turned up in her little white dress and that 
she would have a job keeping his hands off her. We were 
both steamed up by the idea and were beginning to get 
down to it. She said 'I might let him have a feel of my 
tits, what do you think?' I grunted between kisses and 
slipping several fingers into her, said that I thought 
she should. As she manoeuvred to accept my prick, she 
enquired 'should I let him fuck me?' 

Picking up a brutal rhythm I found myself muttering 
between fervent kisses 'oh yes let him fuck you, just do 
whatever he wants, do anything he wants you to do, don't 
refuse him anything. Then I came in a shuddering climax 
and lay on her for a few minutes. When I recovered I 
retreated a little from my unconditional encouragement 
and said 'Really I'm OK with this but you do just 
whatever you want to do. 

She began to speak quietly 'I want him to fuck me, not 
like you do, but just do it. You know stick his dick in 
my mouth and cum on my face and stuff, not be nice but 
use me like a tart, make me do dirty things. I don't 
know what I mean really but he says I'm too nice and I 
want to show him I can give him whatever he wants 
however disgusting.' 

My cock re hardened as she spoke and I pulled her face 
down onto it. 'Show me how you'll suck his dick' I 
ordered, pushing it to the back of her open mouth. She 
tongued it top and bottom and pumped her lips up and 
down on it until suddenly I began to splatter her 
tonsils. 'Let him cum in your mouth, I want you to 
swallow his spunk like a prostitute does' whether they 
did or not I haven't a clue but that's what I said. 
After that we fucked again violently then parted 
exhausted. We drove the short distance home almost in 
silence neither of us wanting to reopen the 
conversation. 
 
We finished early on Fridays and I collected Les from 
her office. It was probably my imagination as I waited 
but the chaps in the cars coming out of the factory 
gates all seemed to look enquiringly at me as they 
passed. Perhaps Frank had let on he was taking my girl 
out? She came down the office steps in her short black 
skirt and crisp white blouse. 

As I pushed open the car door there were a couple of 
complimentary whistles from some factory lads on the 
other side of the road. She waved to them and slide into 
the car. We kissed hello and I joined the homeward 
stream of traffic. I was heading for the usual place 
when she announced she wanted to go straight home. 

'I've got to get ready, that's if you're still ok about 
me going?' I countered 'Do you really want to go out 
with him, and you know, do all that stuff you said?' 

Looking straight ahead, she almost whispered. 'You said, 
you wanted me to be like a prostitute for him and yes, 
the idea gets me hot. It scares me but I want to do it,' 
she reached for my cock as I drove down her road. It was 
rock hard. 'And it turns you on too, doesn't it?' I 
didn't reply but pulled onto the drive of her parent's 
house. 'I'll pick you up 7-30.' She got out. 
 
As the front door opened I was waiting. God, she looked 
good, her pink lipstick matching her heeled sandals, her 
dark eyes flashing through the long lashes and her 
glossy hair in heavy waves around her shoulders. The 
July evening sun shone full on her as she came to the 
car, the deeper tone white of her knickers and bra just 
discernible under the white dress. She swung her legs in 
after she slid into the front seat. 

I glanced down just catching a glimpse of the stocking 
welt, where the dress flapped open below the bottom 
button. I knew if I asked her not to go, she would 
happily just go for a drink with me and forget all about 
it. My stomach churned as I turned the car out of her 
road and headed for the pub on the Hagley road. 

We travelled in silence until we pulled onto the car 
park. The place was a steak house and quite busy. I 
parked where I could see the cars pulling in, off the 
dual carriageway. Les turned to me. 'Are you sure you're 
ok with this?' Her dress gaped open at the top and I 
could see almost all of her breast, brown as a bantam 
egg down to the darkness of her nipple. 'Because if 
you're not. I don't have to go through with it.' she 
paused, 'but if I do, things won't be the same again 
will they?' 

My mouth felt like it was full of cloth. I could hardly 
speak. 'Whatever you do, I'll always want to be with 
you, but I really get off on the idea of you fucking 
him. If you hadn't been keen I would have tried to get 
you to do it somehow.' 

Frank's Rover 3000 pulled onto the car park and parked 
up facing the road. 'He's here.' I said.

'I'm going to do anything he wants,' she whispered, 
opening the car door. 'But it's you I love, wait for me 
at the end of our street.' We didn't kiss. She got out 
and I watched her cross the car park. 

Frank must have spotted her in the mirror as she 
approached, and got out of his car to greet her. He was 
taller than I remembered and not as portly as I had 
imagined, a big bloke. Lesley looked tiny alongside him. 
His large hand momentarily brushed her behind as he 
ushered her to the passenger seat and held the door as 
she stepped in. In a couple of minutes they had gone. I 
was tempted to follow the departing Rover but thought 
better of it and resigned myself to killing time and 
waiting as instructed. 
 
I didn't want to go home to the inevitable, 'where's 
Lesley questions' and for the same reason I wanted to 
avoid the pubs where our friends hung out. In a bit of a 
daze I ended up driving into town buying a 'Wimpy 
Burger' which I normally wouldn't cross the road for, 
then throwing most of it away. More than usual it tasted 
of salty cardboard and my mouth was dry and I couldn't 
swallow. Sitting in the car park I imagined the course 
of events. How long would they spend in the pub? Would 
she be ok? Frank's first move. To touch her breasts or 
explore her legs. 

In the same moment I was both sick with jealousy and 
concern and yet aroused by the idea that my girl was at 
that minute probably straddling a man older than her 
dad. At eleven I pulled into the street just off the end 
of the road where she lived. The Rover pulled up 
opposite just after midnight. Every car that passed in 
either direction had set my stomach churning, now I was 
electrically charged. 

Though it was gloomy away from the street lights I could 
make out Frank sitting in the driver's seat but no sign 
of my girl. If my heart could have pounded any louder it 
would have woken the sleeping estate. A car swept past. 
The brief illumination was enough for my 'locked on' 
vision to discern the rhythmic up and down movement of 
dark shadow above Franks lap. 

'Oh God, she's sucking him off in the street where she 
lives.' Fascinated I watched the car. A few moments 
elapsed then she sat up, and lay back in the seat. There 
was an inaudible exchange of words, and she stepped onto 
the pavement. The car door clicked shut and the Rover 
droned off into the distance. I flashed my car 
headlights. She turned and walked towards the car. She 
looked ok.
 
'Let's go down the lane,' she instructed as she closed 
the car door. Without response I turned the car into the 
main road and drove the few minutes to the lane. This 
was one of our usual haunts and where we were rarely 
disturbed after the pony enthusiasts had gone home. 'How 
was it' I ventured as we came to a halt. 'I'll tell you 
after you fuck me' she replied, already climbing into 
the back of my Anglia. I followed her pushing the seats 
up over the dash for more leg room. 

As I undid the buttons of her dress, she had my jeans 
unzipped and was pushing them round my ankles, reaching 
for my prick. She no longer wore a bra or knickers and 
as I caressed her face with my fingers preparatory to a 
kiss I was aware that her hair was wet and sticky no 
doubt with spunk from that last minute blow job I had 
almost witnessed. 

Our mouths met as my cock eased into her and Lesley 
began to writhe beneath me. I could smell Frank's sperm 
on her hair and felt my tool expanding inside her. 
Turned on but I suppose emotionally confused, I climaxed 
in double quick time, sobbing between kisses, 'God I 
love you.' She began to come in a series of shuddering 
convulsions and then lay still breathing steadily. 

'You are sure you want to hear this?' she demanded. 

I drew her to me, 'Yes.'

She began describing how they went to some pub on the 
back of Clent hills where she judged most of the women 
there were with someone they shouldn't be with and how 
in less than an hour she'd downed four Cherry B's she 
was so nervous. Frank had dared her to show him her 
knickers and she had. Unbuttoning her dress to the waist 
to open it for him in the pub. 

At that point he had said, drink up and they drove to a 
car park on top of Clent somewhere. It was still light. 
Frank had leaned across and kissed her at the same time 
opening her dress at the front. Les said she slid down 
in the seat and he had pushed his hand up between her 
legs and under her behind. He was able to lift her 
bodily and ground the heel of his palm against her cunt 
through her knickers. 'It felt nice,' she said and when 
he pulled his hand back he drew down her flimsy homemade 
G string. 

Then he undid the front fastening bra to knuzzle her 
breasts as his 'fat fingers' her words, gently probed 
her cunt. She reached over to find his dick hard in his 
trousers. At her suggestion they got into the back seat. 
She took off her dress and was now completely naked 
apart from her shoes and stockings. Kneeling in the well 
of the car still in his shirt and trousers, he lifted 
her legs over his shoulders and began eat her out, 
reaching up to tweak her nipples as he did so. 

'It was so good, I found myself pulling his head into my 
crotch,' she confessed. 'Then he turned me over and made 
me put my bum in the air. He continued to lick my cunt 
but started licking around my bum-hole and pushing a 
finger in. He asked me if I liked it! I said it was ok. 
Suddenly he had his tongue in my arse and it felt great 
probing in time with the rhythm of his fingers on my 
clit.

Listening to this was bittersweet. My dick was rock hard 
but I was jealous.

'I wanted it to carry on' she said but Frank turned her 
onto her back again took off his shirt and pushed his 
trousers and pants down and placed the tip of his cock 
at the entrance to her fanny. Lying over her he told 
her, 'If you want it in you, you put it in.' 

She said his penis was about the same size as mine maybe 
a bit longer but not as fat. She grasped it and guided 
it into her. 'It slid in easy, I was so wet' she 
confessed. 'He fucked like mad as soon as he was fully 
in me, and sucked on my nipples and shoved his fingers 
up my bum. In a few seconds he was jerking his spunk 
into me and I wasn't far off coming either. Then he 
pushed his tongue into my mouth and asked, 'If I could 
taste my own arse', dirty bastard, but he kept on 
shagging me and I came off.' 

While they rested Frank asked about what she had done 
with me then got her to suck his floppy cock back to 
life. As soon as it was hard he fucked her doggy fashion 
a bit slower this time. When she sensed he was about to 
come he made her turn round and take it in her mouth 
again. 'My missus never does this,' he told her as his 
come splattered the back of her throat. Les never really 
liked the taste or texture of sperm, but she told me 
because he had said that, it made her determined to 
swallow it down. 

Another break and more talking then Frank wanted to 69. 
Les got on top and Frank cleaned out her fanny and gave 
her brown hole some more attention, licking her clit 
till she had another orgasm, flooding his face with her 
juices. She turned round and began to ride his cock. 

She had begun to wank my dick as she relayed the detail 
of this evening of debauchery. 'There's one last bit,' 
she said carefully. 'While I was riding him, I thought 
he won't come again, so I asked him, what else won't 
your wife do?' 'She won't rim my arse' he replied which 
apparently is what he'd been doing to me.' 

I gasped 'What did you say?' 'I asked him if he wanted 
me to do it for him' said my prim little girlfriend. She 
had then lain back on the seat while Frank knelt astride 
her face. She began by licking and sucking his cock then 
travelling down to his balls. sucking the bit that joins 
the bollocks to the anus, which she said immediately 
made his dick stiff again. Then as she wanked his cock 
with one hand, she applied her mouth to his arse. 

As he held the cheeks of his backside open she licked 
and probed his anus with her tongue, gently reaming it 
open with her fingers. Eventually she could get her 
tongue in and could feel the pressure of his ring piece 
on her tongue both trapping it and pushing it out at the 
same time. Frank could not stand more of this and turned 
to point his prick at her face and shot another load of 
jism into her face.

As she reached this conclusion I pulled her down onto my 
cock and pumped my load into her mouth. She swallowed it 
without complaint.

'And that was it' she concluded. 

'But, you were sucking him off when you turned into the 
street,' I said. 

'That was something else his wife has never done, I'd 
told him I did it for you. And he came again! All in my 
hair. Put the light on,' she replied. 

I switched on the interior light. Her breasts and upper 
thighs were covered in dark blue black love bites. 'He 
asked me if you knew and when I told him, 'yes', he 
said. 'Well he'll know now won't he?' and gave me 
these.'

'Are we ok?' she asked.

'I-I think so,' I said 'will you see him again?'

'If he asks me I will,' she replied.

'That's good,' I said.

The End

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The author does not condone child abuse, this story is 
meant as an erotic fantasy not depicting anything in 
real life. Anyone acting out such scenarios in "real 
life" can look forward to many unproductive years 
getting it up the butt by a fellow convict in their 
local prison system.
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Kristen's collection - Directory 72