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Back to Stories and Fantasies

The Transvestite Neighbour

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By *ay and K888 OP   Man
24 weeks ago

Manchester

Part 1

Some years ago my wife Trudy and I, both in our early thirties, moved home to a new part of the country from our native Preston to Bedfordshire. We moved to a fairly affluent part of the county and had a lovely home with lots of nice neighbours.

We hadn't been in our new place long before we realised that one of our neighbours was a full time Transvestite! Clair was a very attractive "lady" - quite tall with a dark hair in the style of a Bob, with dark brown eyes. She had a lithe frame but well developed boobs - even if they were just padding and very long legs. She was always well turned out in a variety of outfits from dresses to short skirts and jump suits and was always happy to show off her nice legs when it was warm. She was very happy to chat with you and she had that husky tranny voice. Clair was an independant IT expert for a lot of international companies and worked from home. She was obviously very wealthy too!

My wife got on well with her and often the two of them would have coffe together in each other's house. I must admit I always felt a bit awkward around Clair but I'd be lying if I didn't say that I also found her quite sexy!

Trudy my wife was a very attractive girl, perhaps a bit more of her to love than she would have liked with a lovely big ass and great tits. We had a great sex life.

Trudy would often tease me about Clair telling me she had her eye on me and whilst I feigned disgust I secretly found the idea very exciting.

One very hot day during the summer I was in the garden doing some chores in just my shorts - I'm in pretty good shape and work out regular - I had a sheen of sweat over me as I fought aimlessly with trying to remove a tree stump when I heard a voice;

" Helloo darling" it was Clair leaning over the fence. She had on a pair of red hot pants, these legs going on forever and a white halter neck type top. I could see her lovely clevage and it was then I realised her boobs were real.

" You look terribly hot darling - why don't you stop and come over for a cold drink?" she cooed in that fake femm husky voice.

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By *end1Man
24 weeks ago

southend on sea

Like where this is going 👍

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By *eekingfun999TV/TS
24 weeks ago

whitstable

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By *p4it6969500Man
24 weeks ago

burton

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By *igerman23Man
24 weeks ago

hayes

Nice

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By *ozcdTV/TS
24 weeks ago

Travelling

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By *hef2475Couple
24 weeks ago

Blackpool

Oh yeah....

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By *hyguy2360Man
24 weeks ago

renfrewshireish

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By *iker197Man
24 weeks ago

Hinckley

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By *J GeminiTV/TS
24 weeks ago

Northumberland

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By *cotty909Man
24 weeks ago

tranent

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By *asters-slaveMan
24 weeks ago

Preston

Wow

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By *rt1976Man
24 weeks ago

redcar

Don't stop there , keep going

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By *icebigchopperMan
24 weeks ago

Hampshire

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By *uga40Man
24 weeks ago

Hemel Hempstead

Dont stop

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By *lare_thomas38TV/TS
24 weeks ago

my town

Good start

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By *oth0712Man
24 weeks ago

cambridge

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By *ean and lyndaCouple
24 weeks ago

Manchester

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By *K-Bi-50Man
24 weeks ago

Richmond, North Yorks

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By *iona38ddTV/TS
24 weeks ago

north east fife

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By *ikinghornMan
24 weeks ago

hilsea

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By *eeker of pleasureMan
24 weeks ago

manchester

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By *it5373Man
24 weeks ago

here&there

Love a sexy T-girl, is this fact or fiction?

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By *lison 2023TV/TS
24 weeks ago

Liverpool

Good start

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By *icki222TV/TS
24 weeks ago

Lincoln

Mm...I think I’m going to like this one. Claire sounds so sexy. I can’t resist a husky sexy voice hee-hee. More please

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By *rdiscreet327Man
24 weeks ago

Nottinghamshire

This is going to be amazing. Can’t wait for more!

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By *j and c 2Couple
24 weeks ago

mullingar

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By *harlottes ChurchTV/TS
24 weeks ago

Toy me town

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By *urabriteMan
24 weeks ago

stafford

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By *ony 529Man
24 weeks ago

coventry

Mmmm I know there’s more to come wish I had a neighbor like that

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By *ylon_cMan
24 weeks ago

Dunfermline

Looking forward for more.....

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By *ohn.1960Man
24 weeks ago

Southampton

Oh yes this will be good

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By *pagedMan
24 weeks ago

Doncaster

Great start

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By *ackiex32TV/TS
24 weeks ago

Wick

Hooked

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By *rmbtsTV/TS
24 weeks ago

stockport

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By *ndrea54TV/TS
24 weeks ago

cambridge

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By *ednesday 2023TV/TS
24 weeks ago

Stortford

Nice original story

looking forward to hearing more x

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By *usietranslutTV/TS
24 weeks ago

carlow

Wonder what Clair and Trudy end up doing to you?

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By *21funguyMan
24 weeks ago

Bicester

Like this

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By *ay and K888 OP   Man
24 weeks ago

Manchester

Part 2

I was taken aback by just how femm and sexy Clair looked. Those gorgeous brown eyes staring at my torso.

I estimated she was 40 ish but she had that aura of both sex appeal and class.

"I'll have to take a rain check on that I'm afraid" I blurted out. "I need to get this done so I can get off and meet some pals for drink later this afternoon."

Claired Smiled.

"Another time hopefully" and she walked away swaying that great ass. Then she swung around and addresed me again.

"Your making a great job by the way; I might need you to pull some things out for me if you find the time"

She winked and I was left standing there at a loss for words...

Over that long hot summer we became good friends with Clair and our immediate neighbours. We often had barbecues in each others garden and Clair was always invited. On one occasion Clair had a lavish garden party of her own and had lots of friends of her own who attended and curiously enough they were all straight- couples and straight singles both girls and guys. I found it strange that she didn't seem to have a friend there from any of the LGBT scene, but again she was so confident in company her sexuality just never became a topic.

Later that evening the party was going strong and everyone seemd to be at best a little tipsy. Clair past me standing deep in converstaion with Ron, our Neighbour about footy when she Interupted. She draped an arm around my neck on the passing and asked;

" Rick Darling could you be a honey and get some more Champagne from the garage, it's at the back in a bottle fridge."

I had only been drinking beer but still felt a bit unsteady on my feet as I made my way up to the back of the garden. The light was in the garage and I found the huge bottle fridge stowed with wine and Champers.

I pulled two from the rack and as iwas leaving Clair was suddenly beside me. She had ona lovley light blue strappless summer dress which finished high up on her thigh, with strappy heels her red toe nails showing through. I turned around with a bottle in both hands and she came up close.

I could smell her intoxicating perfume as she leaned in close to me. Without warning she grabbed my head in her hands and kissed me. A deep powerful passionate kiss with her tonuge going deep in to my mouth.

I did nothing to stop her. I had a bottle in both hands hanging down by my sides. The kiss lasted a long time and then she pulled off and stood back looking at me, stunnned as I was.

" Sorry darling but I just had to taste you"

And then she grasped my now erect cock through my Chinos.

"Looks like you enjoyed that too" she said as she straightened her dress and touch her hair back into place before walking out and the she turned and oput a conspiratol finger to her lips and winked.

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By *ucksguy2000Man
24 weeks ago

aylesbury

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By *hyguyDublinMan
24 weeks ago

Wexford, Waterford, wicklow

👍

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By *illie_2024Man
24 weeks ago

Ivybridge

Mmmm very hot

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By *andyel73Man
24 weeks ago

Leyland

Fab start can't wait to see where this goes

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By *P69erMan
24 weeks ago

Tamworth

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By *ortheastcoupleukCouple
24 weeks ago

easington were the sun dont shine

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By *eterpervisMan
24 weeks ago

back where i came from

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By *icki222TV/TS
24 weeks ago

Lincoln

This is getting better as we go along. Xxx

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By *cotty909Man
24 weeks ago

tranent

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By *hor66Man
24 weeks ago

Clacton-on-Sea

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By *j and c 2Couple
24 weeks ago

mullingar

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By *21funguyMan
24 weeks ago

Bicester

Wow is this true

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By *ark_sentinelCouple
24 weeks ago

Andover

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By *ndrea54TV/TS
24 weeks ago

cambridge

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By *igerman23Man
24 weeks ago

hayes

Yes oh yes

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By *ndisMan
24 weeks ago

Liverpool

Loving this so far.

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By *red jones40Man
24 weeks ago

rhyl

Loving this

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By *achukMan
24 weeks ago

home

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By *teve1867Man
24 weeks ago

wirral

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By *uga40Man
24 weeks ago

Hemel Hempstead

Well dont stop

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By *eed AttentionMan
24 weeks ago

Oxford

What you call developing

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By *on BurgundieMan
24 weeks ago

Edinburgh

Oh yes

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By *cotswitchMan
24 weeks ago

Uddingston

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By *eeker of pleasureMan
24 weeks ago

manchester

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By *ony 529Man
24 weeks ago

coventry

I’m loving this

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By *un Bi couple yorkshireCouple
24 weeks ago

Doncaster

Intrigued on what is going to happen x

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By *exbot 1Man
24 weeks ago

Chester le street

Interesting mmmm

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By *unguytricountyMan
24 weeks ago

Fordingbridge

Loving this

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By *usie pTV/TS
24 weeks ago

taunton

I don't care what anyone says about being straight very few red blooded men would be able to resist the charms of a girl like Clair for very long.

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By *oorslightMan
24 weeks ago

Strabane

Amazing story. Sounds amazing situation

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By *elbyfuntimesMan
24 weeks ago

Selby

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By *lare_thomas38TV/TS
24 weeks ago

my town

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By *i14Man
24 weeks ago

Rayleigh

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By *h3quietoneMan
24 weeks ago

polegate

More please, loving this and very sexy

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By *inxer petCouple
24 weeks ago

bristol

More please

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By *ed_BlueCouple
24 weeks ago

Loughborough

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By *atriotsMan
24 weeks ago

Huddersfield

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By *fd87Man
24 weeks ago

bradford

Hey

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By *wordsman1Man
24 weeks ago

Dartford Bridge

[Removed by poster at 03/10/24 05:52:48]

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By *rdiscreet327Man
24 weeks ago

Nottinghamshire

So sexy. Clair is such a tease. Really enjoying this op.

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By *hef2475Couple
24 weeks ago

Blackpool

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By *J GeminiTV/TS
24 weeks ago

Northumberland

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By *sprey6Man
24 weeks ago

Here!

Intriguing

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By *ikinghornMan
24 weeks ago

hilsea

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By *ay and K888 OP   Man
24 weeks ago

Manchester

Part 3

After that incident I was left both confused and excited. I started to fantisise about Clair and it left me feeling guilty and uncomfortable when I made love to my wife.

For her part Clair too, didn't make it obvious that anything had happened and we got on with life as usual. Trudy and her still had coffee togther, enjoyed each others company and we went on as normal. There was the odd occasion when Clair and I were togther at a social gathering and I felt a frisson of excitment when she looked at me with these gorgeous big brown eyes or perhaps brushed past me. It was obvious to me that things would go further if the opportunity presented itself.

A month or so later my wife was away for the day visiting family and Clair came to the door asking if I could help her move a table in her house? She was wearing a lovely flowery blouse and a short skirt with very high heels showing off her long slender legs She looked amazing and I found it odd that she would be wearing such provacitive outfit if she was moving furniture!

I agreed I to help and went over to her house a bit later. She showed me through to her lounge and then shamlessly started flirting with me - telling me what a great body I had she loved my smile.

We started kissing in no time and and I started feeling up her boobs-

"oh baby, I love having my titties sucked" she panted as she pulled one of her breasts out from her bra and fed it in to my mouth. I had lsot all restraint and was like a young teenager having sex for he first time.

Clair pulled me by the belt buckle over to the couch and she sat down and unbuttoned my jeans and pulled my boxxers down to my knees! My 8" cock never felt so hard. Clair held my cock in her long fingers like she was inspecting an exhibit. She had a very serious look on her face and then she put her glossy red lips over the head. I was in heaven!

She took half of my cock down her throoat and looked up at me with these huge dark eyes. I sturuggled to control my breathing as she bobbed her her head up and down.

She suddenly pulled off and smiled at me.

" you are a naughty boy " she cooed.

And then very quickly she grasped my cock in her hand and milked it in to my mouth. As I reached climax she swallowed the whole length aggresively pumping her mouth up and down until I exploded down her throat.

Clair took the whole load and then gently pulled her mouth off my erection and wiped her mouth with a hanky.

A feeling of utter shame flooded over me and I quickly pulled my cloths up and gathered myself. I told her I had to go and apologised. As I went to leave she grabbed my arm and pulled me back.

"I understnd darling, but remember - next time I have needs too."

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By *asters-slaveMan
24 weeks ago

Preston

Wow

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By *andyel73Man
24 weeks ago

Leyland

You can't leave a lady waiting

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By *21funguyMan
24 weeks ago

Bicester

Next time

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By *ndrea54TV/TS
24 weeks ago

cambridge

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By *itom18Man
24 weeks ago

Wigan

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By *ikinghornMan
24 weeks ago

hilsea

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By *ony 529Man
24 weeks ago

coventry


" "

Mmmmmmm This is such a turn on in so many ways

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By *ane08TV/TS
24 weeks ago

redruth/ camborne

Very nice I wish I had a niebours like that xx

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By *ixcocoMan
24 weeks ago

liverpool

I'm selling up and moving to your neighbourhood

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By *lan1chunkyMan
24 weeks ago

Prestwich

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By *usie pTV/TS
24 weeks ago

taunton

I well remember the feeling of utter disgust with myself after the first time vowing never to do such a thing again but two days later I was back for more, but once sampled there is no returning to normal the temptation will over come .

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By *idLTMan
24 weeks ago

Leeds

Following...

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By *21funguyMan
24 weeks ago

Bicester

Need details of next meet

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By *ames683Man
24 weeks ago

east devon

Great story

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By *aughtyman45Man
24 weeks ago

lincoln

Very hot

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By *orthampton jamesMan
24 weeks ago

Northampton

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By *lare_thomas38TV/TS
24 weeks ago

my town

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By *alm_one4Man
24 weeks ago

RM16

Bookmarking

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By *igkidexyMan
24 weeks ago

Dublin

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By *hyguy2360Man
24 weeks ago

renfrewshireish

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By *usietranslutTV/TS
24 weeks ago

carlow

Can’t wait for more

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By *nly1meMan
24 weeks ago

here there n everywhere

would love a neighbour like that

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By *onsi69Man
24 weeks ago

llanfairpg

Love it

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By *ardsoloMan
24 weeks ago

Harlow

Definitely need more of this story

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By *rdiscreet327Man
24 weeks ago

Nottinghamshire


"I well remember the feeling of utter disgust with myself after the first time vowing never to do such a thing again but two days later I was back for more, but once sampled there is no returning to normal the temptation will over come . "

Never a truer statement!

Love the story op. I’m so gripped.

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By *ut4fun6969Man
24 weeks ago

Folkestone

Great story

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By *aitingstillMan
24 weeks ago

East of Cork

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By *eekingfun999TV/TS
24 weeks ago

whitstable

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By *penmyeyes11Man
24 weeks ago

south east

Look forward to more

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By *penmyeyes11Man
24 weeks ago

south east

Look forward to more

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By *oeKelly2003TV/TS
24 weeks ago

City

Great story

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By *hristopherd999Man
24 weeks ago

Brentwood

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By *oventry4biTV/TS
24 weeks ago

coventry

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By *oreplayer4uMan
24 weeks ago

mundford area

Great story I’d like a neighbour like that lol, more plz

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By *ullmanMan
24 weeks ago

hull

More please

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By *9Karm69Man
23 weeks ago

plymouth

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By *en1234300Man
23 weeks ago

Peterborough

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By (user no longer on site)
23 weeks ago

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By *ark_sentinelCouple
23 weeks ago

Andover

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By *sprey6Man
23 weeks ago

Here!

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By *ag165Man
23 weeks ago

Greenock

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By *oreplayer4uMan
23 weeks ago

mundford area

Where’s part 4 plz

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By *cotty909Man
23 weeks ago

tranent

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By *athytvsubTV/TS
23 weeks ago

Bulwell, Nottingham

We need more now xx

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By *kivi Bi MaleMan
23 weeks ago

North Shields

I'm awaiting part 4, eagerly and much trepidation ps. very good thought provoking written.

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By *eathersarahTV/TS
23 weeks ago

warrington

Keep going it’s amazing

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By *avem30Man
23 weeks ago

barnsley

Great story

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By *teve1867Man
23 weeks ago

wirral

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By *illygirlWoman
23 weeks ago

Kilmarnock

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By (user no longer on site)
23 weeks ago

Loving where this is going, role on part 4!

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By *acksmith22Man
23 weeks ago

cannock

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By *elfastSteamWhistleMan
23 weeks ago

bangor

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By *ell I WonderMan
23 weeks ago

Staines

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By *eeker of pleasureMan
23 weeks ago

manchester

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By *elly61TV/TS
23 weeks ago

Burnham on Sea


"Loving where this is going, role on part 4! "

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By *oth0712Man
23 weeks ago

cambridge

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By *oneysmithcdTV/TS
23 weeks ago

Glenrothes

More please

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By *elbyfuntimesMan
23 weeks ago

Selby

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By *nly1meMan
23 weeks ago

here there n everywhere

wow more please , would love this

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By *eter4383Man
23 weeks ago

Norfolk

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By *ovingmyknickersgTV/TS
23 weeks ago

cheshire

Now trying to wank into my mouth

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By *d funMan
23 weeks ago

Telford

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By *ini1275Man
23 weeks ago

stoke on trent

Fantastic story hope there's more so horny now

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By *ay and K888 OP   Man
23 weeks ago

Manchester

Part 4

For the next few weeks I avoided Clair and the feeling of guilt receded. Trudy and I had a short break away to Scotland to meet some friends and when we returned the incident seemed like a lifetime ago.

I seen Clair about the house and garden sometime and waved and she waved back.

One night when I returned home late after a few drinks with colleagues I found Clair and Trudy in our kitchen drinking wine. They were both in a merry mood so clearly they had had a few drinks.

Clair wearing a figure hugging Red Blazer Jump suit with a plunging neckline that showed off her clevage. She looked amazing!

We had a good chat like old friends but I could feel these sexy eyes boring in to me and I was suprsised how hard my erection was.

Despite my best efforts to try to put this sordid episode behind me I started to fantasise about her again. I would watch her from my bedroom go to the garage in her robe and when she realised I was watching, her robe started to loosen up so I could catch a glipmse of these perky tits. Despite a great sex life at home I would often masterbate thinking about Clair.

A month later Clair then went abroad with work for a few weeks so I hadn't been in her companty for a while.

When she returned from abroad she came over with a few gifts for both Trudy and I and we shared another few drinks together and I longed for an opportunity to tell her that I was wanting to have another illicit meet with her.

" you look very sexy today" I said when Trudy went to the toilet and she blushed.

" I told you you were naughty" she whispered. And then she moved to get another drink and as she passed behind me she deliberatley rubbed her breasts against my back! I was so hard.

In Early December Trudy and her pals were away for a long weekend to France. The opportunity had presented itself and Clair was aware that she was away too.

On the Saturday afternoon that weekend Clair phoned the house and asked if Id like to join her for a drink. I was flustered as I spoke to her knowing only too well what would happen if I went next door. I told her I didn't think it was a good idea but my protestations were lame. My heart was thumping as she whispered - " Come over when your ready there is no rush- we have all day. I've just had a nice shower and shaved my legs - I'd love you to see me in my new sexy hold up stockings...

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By *p4it6969500Man
23 weeks ago

burton

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By *umpstyleMan
23 weeks ago

North

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By *ndrea54TV/TS
23 weeks ago

cambridge

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By *avem30Man
23 weeks ago

barnsley

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By *lljambarMan
23 weeks ago

Manchester

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By *midsfabguyMan
23 weeks ago

WMids

Mmmmm

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By *ay and K888 OP   Man
23 weeks ago

Manchester

Part 5

My hands were shaking as I stood at her front door. I was trying to talk myself out of being here but the pull of this erotic liason was too much. The door opened and ther she was! Clair was wearing a white lace and satin Kinomo type dressing gown which stopped at the top of her thigh and and I could see the new white satin hold up stockings. The cups of her white bra showed enticingly beneath the robe. Of course she had to have stilletoes on. I gasped as looked at her and she pulled me in and closed the door. She wrapped her arms around me and kissed me long and deep - her tongue again probing my tonsils. She pulled off and seductively pulled my by the arm the stairs to her bedroom. The blinds were closed and there was just enough natural light to enhance the room.

Clair slowly unbuttoned my shirt and pulled it off, kissing my chest as she leaned down to unbuckle me. She knelt down as she pulled my Jeans and boxers down, looking up at me with those huge eyes - my cock sprang out. I don't think I've ever flet so hard in my life. She very slowly put her lovely mouth around the head and sucked in sharp short movments. She never took anymore than the head in her mouth but it was heaven.

She stood up and walked me back to the bed where I sat down. She stood back from me and slowly opened the robe. I thoought I would pass out looking at her body as she threw the robe to floor. She stood there letting me drink in her beauty and then she turned her back and seductively peeled the panties down. She stood there with her back to me, she looked so tall especially with her heels still on.

And then shen turned around! What a sight!

The fleshy part above her stocking tops - creamy and inviting and then her huge massive cock! Above a Brazilian dark strip trimmed with precison.

She moved towards the bed, I looked up feeling nervous and unsure. She reached down to my chin and pulled my head up. We both knew what was going to happen but I was so conflicted my erection shrank.

"Open Baby" she hushed.

I started to protest but she wasn't going to be stopped.

"Open"

The head of her cock was in my mouth, I Could feel the hard warmth of her shaft. I could taste the perfume of the helmet.

I sturggled to take such a monster cock but she pushed firmly so half of it was in my mouth. I shook my head to indicate I wasn't comfortable but she jerked her cock in and out of my mouth becoming more and more excited.

I started to gag as she pushed harder and then I managed to pull my mouth of her grip.

" Oh baby, we'll need to work on that" she said and the she pushed me back onto the bed. She climbed up beside me kissing me hard our cocks touching. It was such a weird feeling but so hot too. Clair sat up on me and ran her hand down my chest.

" Darling, do you want to make love or fuck?"

I couldn't speak I was so caught up in the passion of the moment.

She leaned down to me ear and whispered;

" I'll decide then..."

I could see her leaning over me to the bedside cabinet and she unscrewed a small jar. Now she pressed up on her knees and put her had behind her bum. She lubed up her hole and then she was kissing me again.

She started to rise up and at the same time she grasped my cock and positioned it just below her boy cunt.

For a moment I went to protest but she ignored me and gently and slowly lowered herself down over my cock before she had all of me inside her, we both sighed.

It was vice tight around my shaft.

"mmm Baby you are stretching me, you sexy boy" she cooed.

And then she started a nice slow rhythm.

I could feel my blood pounding in my ears as moved towards climax. Clair leaned over me and pulled one of her cups down and fed her tit in to my mouth and moaned. Then started to bounce harder now and she grabbed her own cock in her hand and began to masterbate it.

"oh, oh oh, oh,oooohhhhhh!" she moaned.

I exploded beneath her just as she came too shooting warm spunk over my chest. She continued to milk her cock until she was dry and then she reached her long finger up and spread the gooey white mess over my nipples.

She raised herslef off my and went to the en suite. She returned with a wet flannel and a towel.

She cleaned my chest and lay down beside me.

" Was that good? Next time will be even better..."

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By *ay and K888 OP   Man
23 weeks ago

Manchester

Hope your all enjoying.

If this thread gets full I'll post the concluding episode in a new thread but it will be titled the same.

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By *ikinghornMan
23 weeks ago

hilsea

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By (user no longer on site)
23 weeks ago

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By *itom18Man
23 weeks ago

Wigan

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By *usie pTV/TS
23 weeks ago

taunton

I am beginning to think there is a lot of truth in this story, the way he describes attraction is spot on men just can't resist.

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By *ndrea54TV/TS
23 weeks ago

cambridge

So hot

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By *aughty grease monkeyMan
23 weeks ago

Coventry

What a lucky guy so jealous love a neighbour like that xxxx

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By *oreplayer4uMan
23 weeks ago

mundford area

Thought they were going to get caught by the wife , and secretly they were already playing behind his back ,

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By *lljambarMan
23 weeks ago

Manchester

Great story

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By *eterpervisMan
23 weeks ago

back where i came from

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By *ovingmyknickersgTV/TS
23 weeks ago

cheshire

Yes really enjoying this.

I had to put my knickers on to carry on reading with a full erection straining at them

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By *inkydresser81TV/TS
23 weeks ago

Teesside/ York

Mmm such a hot story. Messed my panties reading it lol

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By *asters-slaveMan
23 weeks ago

Preston

Amazing

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By *elbyfuntimesMan
23 weeks ago

Selby

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By *eekingfun999TV/TS
23 weeks ago

whitstable

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By *ut4fun6969Man
23 weeks ago

Folkestone

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By *rdiscreet327Man
23 weeks ago

Nottinghamshire

Absolutely love this. The details are brilliant.

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By *ark_sentinelCouple
23 weeks ago

Andover

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By *ini1275Man
23 weeks ago

stoke on trent

Got me hooked x

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By *avem30Man
23 weeks ago

barnsley

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