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Old 09-28-2022, 05:17 AM
explorer98 explorer98 is offline
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Reading this thread it's kinda nice to see that other guys were having similar thoughts and experiences. Looking back through my own, it's very clear to see where and how a lot of my 'perversions' started but also, I seriously can't believe the amount of front I must have had when I was younger!! For a guy who's not particularly confident around other people, I did quite well with ladies - though sometimes at a cost!!

I've had a thing for older women since I was 13 - probably earlier actually - because my first-year primary teacher was a gorgeous woman who I clearly remember as wearing light brown stockings (maybe tights) but the important thing was that she wore beige leather, heeled Scholl exercise sandals - and she had really pretty feet!

That's 53 years ago!!

June Wragg was the only attractive woman in the school - and she was an absolute sweetheart too. I never wanted to move up from her class!

So, 13 - my then-girlfriend's mum. Oh my god she was hot! Flaming red, curly hair, Maureen was the original MILF and in 1975, that term hadn't even been invented! I remember one day which affected me profoundly when I was in their kitchen and she'd been in the bath. She came down in just a big, white towel - still quite wet - and I was 'affected' shall we say??!!

She's in her 80's now but looking at her Facebook photos, I still would....!!!

Before I left school I was having a thing with a friend of my mother's. Sue was 24 and had the biggest rack I'd ever seen at that age. We never actually had full sex but we came very close on many occasions and spent a lot of time rolling around naked together, fumbling, sicking, licking, fondling etc. Unfortunately word reached the wrong ears and we were kept well apart after that but we had months of fun together.

I started work at 16 at a local engineering business and there was only one woman on the shop floor. Gladys was 59 and she had a real 1940's 'glamour' about her - dyed, black hair, always perfect makeup and in particular, fabulous, scarlet lipstick which she'd re-apply several times a day.

Gladys worked shorter days than the rest of us and on the odd occasion, I'd happen to be in or close by the canteen as she was changing to go home. For work, she wore the classic, shapeless, sexless bib and brace overalls but underneath....

French knickers, stockings and suspenders!!

FUCKING HELL!!!!

And for whatever reason, she made no attempt to hide herself if she noticed me watching.

I genuinely have no idea how this progressed but somehow - having noticed the two inches of silky, creamy thigh above her stockings, I eventually contrived somehow for her to let me touch her!! Thinking back, I still can't believe it! This 'respectable' married 59-year-old woman allowing this randy 16-year-old to touch her bare thigh??!! Well I wasn't complaining!

I know I complimented her on her sexy underwear, her makeup and basically (horribly contrived really) said 'all the right things' and it wasn't long before we we'd progressed to kissing occasionally. Essentially, we'd look out for days when there weren't many in the building and we could be sure of being undisturbed for a few minutes and we'd usually take up station by the canteen door which gave us a long view down the workshop and with that being the only route in or out, we'd see anyone coming before they saw us.

From kissing, it went to me standing behind her wit my hands in her bra, gently rolling her nipples - which she adored - and that soon led to her playing with my rock-hard 16-year-old cock while I did it. I was in heaven!!!

I was only there nine months but I so wished I'd been in a position to make more of what I'd started with Gladys. In subsequent years, I've often calculated her age with respect to mine and I have no doubt she'd have stayed just as glamourous as she was when I knew her.

Two months before my 17th birthday, my band were playing a show in Sheffield and our singer (quite a bit older than me) had arranged for four ladies he knew to be there to see us play. After the show and while we were loading our gear, one of them came over to me in a fluster and said ;"Why are you still here? You're supposed to be with Hazel".

I had not idea what she was talking about but within minutes, I was in the back of a car with Hazel, one of the other women and the other woman's boyfriend. We arrived at what emerged to be Hazel's house and while I sat - still mildly bemused by the whole thing - in her lounge, it became quite clear that the somewhat heated discussion taking place in the kitchen was about me and my age!

Cut past that and the others left so it was just me with Hazel, who - it also emerged - would be 34 the day before I would be 17 and it also became abundantly clear that we were going to bed together!!

I still had no idea how this had come about!

Anyway....

Lots of kissing, cuddling, fondling and undressing took place before the doorbell rang - and this was close to midnight - who'd be ringing the door at nearly midnight? Turned out is was the other guys from the band who'd come to take me home!

Sorry fellas - not happening!! We were only getting started and there was no way I was letting this moment go now!! Got rid of them and back to the lovely lady! One enduring memory from that night is the image I had/have of following her up the stairs - Hazel by now completely naked and gorgeous - and making our way to her bed.

Sleep? Forget it! I slept from 6am to around 7:30 and we got up around 11:30. Either side of that, we just had non-stop sex! I'd wanted something like this for a long time and was delighted to find that unlike the stereotypical teenager, I didn't go off in a couple of minutes and we had a thoroughly wonderful LONG time.

Unexpectedly around lunchtime on the Sunday, our singer rocked up again (he lived a lit nearer than I did) to take me home! I much have been absolutely unbearable and I know I was like a dog with two dicks! Unfortunately they guys hadn't told me family where I was and my mother had been going bats! The police were involved and all sorts of chaos came down - all because the other guys were married and didn't want their wives to know what had gone down!

Ho hum....!!

A couple of years later, I'd been out 'with the lads' and two of us dropped into a local pub for a last drink before going home. On the dance floor, I noticed my ex-girlfriend's sister and sister-in-law. Her sister was a moose but the SIL? Oh yes!! I'd always fancied her. I was 19 by now and she'd be 39. Irish - another green-eyed redhead - and properly hot!!

Margaret (the SIL) spotted me and hauled me onto the dance floor. She'd clearly had 'enough' to drink and as she ground herself into me, she explained very clearly that I was going to be taking them home "...and you're dropping HER off first!" gesturing towards my ex's sister!

She went on to tell me hat she'd always fancied me but would never let anything happen while I was with C "but now you're not..."!!!

Margaret deserves a story all her own - we had LOTS of fun! That went on to be what I still consider perhaps the most honest relationship of my life. She wanted sex with a younger man (me) and I wanted her. We were both happy with that! Funny thing was though; her old man was banging another woman and there's no way on earth she could have been nearly as sexy as Margaret was. How could he not know what he had at home??!!

I left home at 20 to move in with a woman who was 33 the day after my 20th birthday. That went on for a couple of years and we were at it like rabbits! I then moved away but after a short time in my new town ,started a brief thing with a lovely divorcee who worked in the kitchen where I did my electronics training.

Pauline was 20 years older than me, had gorgeous brown eyes, a canyonesque cleavage that smelled wonderful when I stood near her and she also had very pretty feet AND wore exercise sandals to work! It started with me servicing her car which quickly led to me servicing her - gorgeous!!!

Then along came Carole....
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When I say 'older women' that's older than me, not just my daughters!
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