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My first older woman

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By *dventurous bi OP   Man
13 weeks ago

tesside

I was 18, not long started at my first job when I was sent to Edinburgh on a two week training course.

The delegates were a very mixed bunch, two of us were young lads, the rest ranged from 28 to their 50s.

The days were very formal, various department heads came to lecture us on procedures and evening meals always included at least one of them and a director. It meant we were often engaged in work till 9 o’clock.

Two of the 28yr old ladies kind of gravitated to me and the other lad and we would sit together for meals and when we were finally free what was left of our evenings were spent chatting and drinking. Olive was a Geordie lass and I used to try and make sure we were close.

She was attractive, with long dark brown hair, sparkly eyes and a full figure. Ripe peachy arse, an hourglass figure with a gorgeous bust. Her taste for low cut tops made it difficult to keep your eyes away from her cleavage. Cynthia was blonde and similarly built but it was Olive that always found the smutty side to a conversation.

Late one night Olive and I were the last two in the lounge. The sofa was large but somehow we were really close together on it. We’d enjoyed wine and beer and maybe it was the alcohol that gave me courage, maybe I had picked up on her signals, but I ventured the question “would it be ok if I kissed you?”

Her response was to take my face in her hands and lean in to me.

The kiss was soft at first, her hand on my cheek accentuating the feeling and then her lips parted for my tongue and we moved closer as the kiss became more passionate.

She broke the kiss and wriggled herself to be able to stretch out on the sofa and then pulled me on top of her for another kiss. My cock was uncomfortably hard in my jeans and there was no way she couldn’t feel it pressing against her.

I slid my hand up under her sweater and onto the lacy edges of her bra and she again broke the kiss, manoeuvred herself to be able to unfasten herself and freed her breasts to my touch. I couldn’t believe what was happening, but now I lifted the jumper and began to kiss any bite her breasts. Her reaction was obvious. Her back arched to lift herself to me and I let a hand drop to her thigh and began to slide it up her leg. She stopped me, “I can’t, it’s the wrong week”. Well, that was disappointing, but we went back to kissing and me playing with her breasts. Huge aureole and nipples and an obvious source of pleasure for her.

Eventually, she pushed me off and took control. Kneeling over me she touched my cock through my jeans and I very nearly came at that first touch but she sensed that and quickly had my jeans unfastened and my cock freed. I was lost at this point. Just laying there as she stared at my stiffness and gently wrapped her fingers around it, her face so close that I could feel her breath. I reached to touch her breasts but she pulled away and said “no, I want to focus” squeeze “on this”

Her tongue rolled over the tip of my cock and her grip tightened, then she bobbed her head and took me into her mouth as she slowly moved her fingers up and down my cock. I stiffened and groaned and tried to hold back but she was getting what she wanted and increased the grip and the depth of my cock in her mouth “let it go, let it go now”

18yr old me released (we were all very productive at 18 weren’t we) and she swallowed the first spurt and took most of the rest on her face and hair.

We tidied ourselves up and headed off to our seperate rooms. Happily there were still a few nights of the course yet to come…

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By *yceloonMan
13 weeks ago

Aberdeen

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By *teviem48Man
13 weeks ago

stoke

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By *OTSOSUBTLEMan
13 weeks ago

DUBLIN

fab

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By *kpiercedCouple
13 weeks ago

walsall

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By *tephine DommeTV/TS
13 weeks ago

Dublin /Waterford

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By *oth0712Man
13 weeks ago

cambridge

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By *rego69Man
13 weeks ago

Chelmsford

Very nice

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By *ragsterMan
13 weeks ago

Blackburn

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By *ucksguy2000Man
13 weeks ago

aylesbury

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By *octordigitsMan
13 weeks ago

nearby

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By *ig daddy 1969Man
13 weeks ago

manchester

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By *ornybarMan
13 weeks ago

clonmel

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By *alented tongue69Man
13 weeks ago

nearby

And all this happened in the lounge of a hotel !!

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By *ton_maleMan
13 weeks ago

Shoreham

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By *ortheastcoupleukCouple
13 weeks ago

easington were the sun dont shine

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By *j and c 2Couple
13 weeks ago

mullingar

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By *ylonloonMan
13 weeks ago

North West

Loving it 🔥❤️🔥

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By *ucati93Man
13 weeks ago

Aberdeenshire

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By *w2233Man
13 weeks ago

Paignton

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By *oppy12Man
13 weeks ago

Swindon

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By *avidNPMan
13 weeks ago

manchester

I love older women can’t get enough of them. For flirted with my a client at work she’s around 65 years old I’m 43

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By *izzygizzMan
13 weeks ago

manchester

My 1st older woman, i was 19 she was late 50s, an old bloke from pub, his wifec oh my god, so horny

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By *BM Studios EssexMan
13 weeks ago

Colchester , Essex

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By *hitelotusMan
13 weeks ago

Farnborough

My first experience was with older and that is why I have always had a great appreciation for real women body and MILFs

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By *reddy96Man
13 weeks ago

scunthorpe

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By *nthony692020Man
13 weeks ago

chelmsford

My 1st older woman was an American girl west coast while I was on Exercise with the Army near Seattle, she worked in a bank and met her while in a pub, she chatted all night to me I was 18 years old 1st tour as 18 year old lucky me. She took my hand and said come with me home i fucked her all night was well fit then 15mins solid as a rock she loved playing and said are all English boys like me lol god was she dirty. Toto by Africa was on the record player. She did anal the whole thing old er women such a turn on.

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By *oth0712Man
13 weeks ago

cambridge

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By *ragsterMan
13 weeks ago

Blackburn

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By *eandTaffyCouple
13 weeks ago

Blackpool

Happy memories getting an older woman when I was 16 x

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By *ormladMan
13 weeks ago

Glasgow/ Kilmarnock

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By (user no longer on site)
13 weeks ago

Great start 🔥

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By *ylonAlisonTV/TS
13 weeks ago

Bury, Lancashire

My first older lady was 32,I was just 18,she was a fantastic 18th birthday present

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By *ornybarMan
12 weeks ago

clonmel

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By *ayarMan
12 weeks ago

Wirral

Need to read about all these stories

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By *tephine DommeTV/TS
12 weeks ago

Dublin /Waterford

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By *cotty909Man
12 weeks ago

tranent

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By *eteeMan
12 weeks ago

limerick tipp border

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By *dventurous bi OP   Man
12 weeks ago

tesside

The next day at breakfast she was slightly distant, avoided eye contact and dialled down the flirty stuff. I wondered if she had regrets. We were due to go on a visit to Head Office that day and cars arrived for us straight after breakfast. As the cars filled I realised that she and I were last in line and would be travelling together. We sat in the back together and as the car pulled off her hand moved to my crotch and gave me a squeeze. “Act normal today” she said, “but when we get back later I have something for you”

My day was spent in a bit of a haze. We toured the offices, saw the Computer Rooms, met various heads of department but I spent a lot of time watching her and wondering what the surprise might be.

Everyone got into the same cars for the return journey. This time she took my hand and guided it under her skirt. “My period stopped” she smiled. I slid my hand up her legs to find stocking tops and a pair of lacy knickers. “Enough for now” she said as she gently moved my hand back to my side of the car.

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By *ragsterMan
12 weeks ago

Blackburn

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By *an79Man
12 weeks ago

Nottingham

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By *ornybarMan
12 weeks ago

clonmel

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By *ubFTMTV/TS
12 weeks ago

Swindon

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By *tephine DommeTV/TS
12 weeks ago

Dublin /Waterford

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By * F FooMan
12 weeks ago

Runcorn

Looking forward to the next update

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By *ig daddy 1969Man
12 weeks ago

manchester

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By *eeman1Man
12 weeks ago

Liverpool

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By *cott60Man
12 weeks ago

Perth

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By *groot20Couple
12 weeks ago

Mayfair

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By *dventurous bi OP   Man
12 weeks ago

tesside

There were a couple of hours free before the evening meal and people were debating options of popping to the pub, just going for a walk on the Royal Mile or sitting in the lounge area. For clarity, this wasn’t a hotel. It was a big Georgian house close to Edinburgh Castle that was used as a training lodge for the bank.

As everyone went their own way Olive said she was going to her room for a bit of quiet time and as she left she winked at me and mouthed “Room 22”.

I waited a while and said I was going to take a break too. The men were all on the first floor with the women on the second so my going up that second flight of stairs carried the risk of being spotted ‘out of bounds’ but luckily i made it unseen and gave a light tap on her door. The door opened and she pulled me in. She had removed her top and skirt and stood there in stockings and white bra and knickers. She wrapped her arms around me and kissed me. Hard, her lips parting to allow my tongue to meet hers.

As the kiss continued she unbuttoned my shirt and raked her nails across my chest. I was in heaven.

I started to unfasten her bra and she stopped me. “Slow down boy. We’ve got time.”

I was no virgin but I was definitely inexperienced and this idea of the woman taking control was totally new to me.

She moved to the bed, lay on it and asked if I liked what I saw. I was transfixed, her breasts were barely constrained by the lace of the bra and I could see her bush through the lace of the knickers.

“Kiss me” i leant toward her face and she pushed my head down toward her breasts, “there, and anywhere further down”. I kissed the mound of her and pulled the cup of her bra away so that I could kiss her nipples “Bite me, bite me hard” oh my god, as I tentatively took her nipple between my teeth she squirmed and arched her back, took a grip of my head and pulled me onto her. “Bite harder!”

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By *onnoisseur100Man
12 weeks ago

Woking-ish

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By *ilkey69Man
12 weeks ago

Barnsley

Oh yes oldies ate hot

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By *ilkey69Man
12 weeks ago

Barnsley

Oh yes oldies are hot

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By *aitingstillMan
12 weeks ago

East of Cork

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By *uga40Man
12 weeks ago

Hemel Hempstead

Do tell more

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By *oth0712Man
12 weeks ago

cambridge

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By *ornybarMan
12 weeks ago

clonmel

Wow

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By *reddy96Man
12 weeks ago

scunthorpe

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By *2spikeMan
12 weeks ago

Southsea

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By *j89100Man
12 weeks ago

limerick

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By *namoratomanMan
12 weeks ago

Herefordshire

Starting to build up nicely!

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By *ndyandMandyCouple
12 weeks ago

swansea

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By *an79Man
12 weeks ago

Nottingham

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By *dventurous bi OP   Man
12 weeks ago

tesside

There’s more to come, but life gets in the way sometimes. Plus, the first part was all fundamentally true whilst the second is more of a fantasy version of my next days with Olive (and maybe Cynthia)

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By *eteeMan
12 weeks ago

limerick tipp border

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By *uddle4uMan
12 weeks ago

Purbeck

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By *oyntzMan
12 weeks ago

all over Ireland

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By *ucati93Man
12 weeks ago

Aberdeenshire

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By *dventurous bi OP   Man
12 weeks ago

tesside

I’m going to stop here. I’m finding it hard to develop from a story to a fantasy.

We did spend some time in her room the next day but it was just a snog and a handjob.

Eighteen year old me wouldn’t have been anywhere close to being able to handle the sort of fantasy that I was developing. But I will always be grateful to Olive for the hand she had in my sexual growth.

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By *uffhoundMan
12 weeks ago

Bourne, Lincolnshire

Well that's disappointing, just as things were getting interesting!

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By *an79Man
12 weeks ago

Nottingham

Thanks for sharing OP

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