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Whats the most awkward question on a first date......

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By *aptain V OP   Man
25 weeks ago

Birstall, Leicester

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By *amie HantsWoman
25 weeks ago

Atlantis

Why are you single?

What are you meant to say? Because I have a doughy physique and off putting personality. Thank you for asking

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By *uriousscouserWoman
25 weeks ago

Wirral

"Do you think that's a shaving rash or does it look more like an STI?"

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By *icecouple561Couple
Forum Mod

25 weeks ago

East Sussex

"were you the judge that sentenced me?"

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By *r John WickMan
25 weeks ago

The Continental

Wanna fuck?

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By *y AmoreMan
25 weeks ago

london

Was that you?!

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By *elticGent2024Man
25 weeks ago

Bletchley

Will you marry me?

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By *ickyKlungespeareMan
25 weeks ago

St Leonards

Do you see Jesus in the gazpacho too?

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By (user no longer on site)
25 weeks ago

How many kids do you want to have?

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By *d4fun73Man
25 weeks ago

Shipley

Do you take it up the arse!

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By *bi HaiveMan
Forum Mod

25 weeks ago

Cheeseville, Somerset

So.

Did you mum/dad/brother/sister (delete as applicable) tell you how good I am in the sack?

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By (user no longer on site)
25 weeks ago


"How many kids do you want to have?"

Do you love me?

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By *he Silver FuxMan
25 weeks ago

Uttoxeter

“Does your Mum want a drink if she’s staying?”

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By *uriousscouserWoman
25 weeks ago

Wirral


"Do you see Jesus in the gazpacho too?"

Fair play, that would be both unexpected and disconcerting!

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By *ickyKlungespeareMan
25 weeks ago

St Leonards


"Do you see Jesus in the gazpacho too?

Fair play, that would be both unexpected and disconcerting!"

Agreed.

But....do you?

DO....YOU!!!?

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By (user no longer on site)
25 weeks ago


"How many kids do you want to have?

Do you love me?"

Do you have British citizenship and can you give me £1,630 and will you sit the Life Test for me?

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By *ickyKlungespeareMan
25 weeks ago

St Leonards

Do you like ice cream?

I like ice cream.

We're having ice cream.

Here - give me the menu.

I'm choosing your food.

No need for a cab home.

I'm driving you.

(I scared myself there )

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By *idnight RamblerMan
25 weeks ago

Pershore

Why are you wearing a wedding dress?

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By *iaandjamesCouple
25 weeks ago

UK

I had a woman demand that I take her home to meet my parents afterwards, we were both 20 and i hadnt long moved back in with them.

I was that shocked I went along with it. Needless to say my parents weren't happy about the 'chav' that I had just shown up with, as casually as if we had been together for years.

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By *y AmoreMan
25 weeks ago

london

So we’re a couple now

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By *allandathleticMan
25 weeks ago

Asgard

Why do you have cum on your chin?

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By *ickyKlungespeareMan
25 weeks ago

St Leonards

You don't mind me choosing this restaurant because my ex is here with his new girlfriend do you Nicky?

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By *bi HaiveMan
Forum Mod

25 weeks ago

Cheeseville, Somerset

Wanna get matching face tattoos?

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By *oozleMan
25 weeks ago

high wycombe

Do you like cages…….

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By *odgerMooreMan
25 weeks ago

Carlisle

So…. About me… Ive been single 7 hrs and that skanky ho has been telling everyone Im riddled with Chlamydia - but it’s a sweat rash … look!!!

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By *lexm87Man
25 weeks ago

Various

Oh, sorry, I thought you said you worked at Carstairs...

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By *uffolkcouple-bi onlyCouple
25 weeks ago

West Suffolk

Do you like anal?

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By *ris GrayMan
25 weeks ago

Dorchester

Who are you again

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By *ickyKlungespeareMan
25 weeks ago

St Leonards


"Who are you again "

Can me and Fred bang you then?

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By *ris GrayMan
25 weeks ago

Dorchester


"Who are you again

Can me and Fred bang you then?"

lol

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By *lowupdollTV/TS
25 weeks ago

Herts

What are the chances we are both serial killers?

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By *ris GrayMan
25 weeks ago

Dorchester

Are you deaf i said

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By *ris GrayMan
25 weeks ago

Dorchester

[Removed by poster at 03/06/24 12:58:04]

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By *ris GrayMan
25 weeks ago

Dorchester

I have crab do you want one?

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By *lowupdollTV/TS
25 weeks ago

Herts

You have more penis than I was expecting, are you planning on keeping it?

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By (user no longer on site)
25 weeks ago

Would you mind wearing this mask as you look nothing like your pictures?

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By *jorkishMan
25 weeks ago

Seaforth


"Would you mind wearing this mask as you look nothing like your pictures?"

Forum post winner well done

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By *ivemealadybonerWoman
25 weeks ago

somewhere

My now ex husband, said when we was I think 19, said "I fancy going swinging"...my eyes widened, I must have heard what swinging was somewhere all those years ago, I thought "bit much for a first date!" We went for a drive, he directed me to a bloody playground and had a wail of a time on the swings lol

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By *he Silver FuxMan
25 weeks ago

Uttoxeter


"Would you mind wearing this mask as you look nothing like your pictures?"

*pulls out a Suella Braverman with the realistic hair

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By *ickyKlungespeareMan
25 weeks ago

St Leonards


"My now ex husband, said when we was I think 19, said "I fancy going swinging"...my eyes widened, I must have heard what swinging was somewhere all those years ago, I thought "bit much for a first date!" We went for a drive, he directed me to a bloody playground and had a wail of a time on the swings lol"

All the feels

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By *ickyKlungespeareMan
25 weeks ago

St Leonards


"What are the chances we are both serial killers? "

High I'd say Glow.

Very, very high .

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By *pdudeMan
25 weeks ago

newtown

You don't live with 100 meters of a school so you?

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By *idlandiaMan
25 weeks ago

Birmingham

Not a first date of mine, but was once at a restaurant where there was a first date was happening on the next table.

Despite her best efforts, he kept bringing the conversation back to whether she was a virgin or not.

I don't think he got a second date

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By *aribbean King 1985Man
25 weeks ago

South West London

A person's body count

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By *agatoXXXMan
25 weeks ago

Gone and completely forgotten.


"A person's body count"

Alive or dead?

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By *ris GrayMan
25 weeks ago

Dorchester


"You don't live with 100 meters of a school so you? "
that reminds me they're coming to read mine, thanks

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By *rBobbMan
25 weeks ago

Birmingham

How much money have you got, including savings?

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By *ris GrayMan
25 weeks ago

Dorchester


"How much money have you got, including savings?"
you've been watching too much TV haven't you?

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By *rBobbMan
25 weeks ago

Birmingham


"How much money have you got, including savings?you've been watching too much TV haven't you? "

I can't afford one

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By *pdudeMan
25 weeks ago

newtown

I hate spell checker

That should of read " you don't live within 100 meters of a school do you?"

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By *lowupdollTV/TS
25 weeks ago

Herts


"How much money have you got, including savings?you've been watching too much TV haven't you? "

Do they usually have money and saving then?

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By *wiss Army KnifeMan
25 weeks ago

Second star to the right…

Do you mind if that hot woman on the next table joins us?

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By *oastal1968Man
25 weeks ago

London

Not a first line, but while in a pretty rough night club, got chatting to an extremely posh girl who was with some of her friends and who had obviously never been in such an grubby establishment before. We were getting on fine and she must have forgotten where she was when she asked me "Do you sail? Daddy's got a yacht." To which I replied "No I don't sail, but I can show you my rollocks."

It worked because I went on to be her bit of rough for a few months.

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By *aribbean King 1985Man
25 weeks ago

South West London


"A person's body count

Alive or dead?"

Both

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By *aribbean King 1985Man
25 weeks ago

South West London

Also shouldnt ask a persons salary on a date

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By (user no longer on site)
25 weeks ago

I don't suppose you have any Diareze tablets on you?

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By *cLovin2Man
25 weeks ago

Reading


"Why are you wearing a wedding dress?"

Don't walk, feckin run

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By *ris GrayMan
25 weeks ago

Dorchester


"How much money have you got, including savings?you've been watching too much TV haven't you?

Do they usually have money and saving then? "

not if they have a bank account..... Nooooo

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By *cLovin2Man
25 weeks ago

Reading


"Would you mind wearing this mask as you look nothing like your pictures?"

I have a similar one where I ask her to wear a Tesco carrier bag

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By *cLovin2Man
25 weeks ago

Reading


"Would you mind wearing this mask as you look nothing like your pictures?

*pulls out a Suella Braverman with the realistic hair

"

Jesus feck

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By *irthandgirthMan
25 weeks ago

Camberley occasionally doncaster

Could you wear this Dianne Abbott mask?

Have you got any canestan?

Have you got any zovirax?

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By *ris GrayMan
25 weeks ago

Dorchester

I'm dieing this week can you give me the last fuck of my life

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By *aptain V OP   Man
25 weeks ago

Birstall, Leicester

Do you come here often lol

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By *ris GrayMan
25 weeks ago

Dorchester

Who are you and what am i doing here?

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By *earmegrowlMan
25 weeks ago

wolves

How many have you slept with if they are not a swinger u know you will be judged

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By (user no longer on site)
25 weeks ago

Ok, you've had your fun, but could you untie me and let me go now?

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By *ris GrayMan
25 weeks ago

Dorchester


"Ok, you've had your fun, but could you untie me and let me go now?"
is their anybody there

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By *reen as JadeCouple
25 weeks ago

Cheshire


"Do you take it up the arse!"
hehehe x at least you asked x

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By *agatoXXXMan
25 weeks ago

Gone and completely forgotten.

Does this rag smell of chloroform?

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By (user no longer on site)
25 weeks ago

How many partners have you had

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By *aturefunswTV/TS
25 weeks ago

bristol

Do you mind if I ask ? Are you on fab ?

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By *ris GrayMan
25 weeks ago

Dorchester

Have you fabbed idol willys pride pic yet?

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By *udding RoseWoman
25 weeks ago

Somewhere out there


"Why are you single?

What are you meant to say? Because I have a doughy physique and off putting personality. Thank you for asking "

That is the worst question, hate being asked it! Is there something wrong with being single or something?

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By *onameyet2Man
25 weeks ago

chorley


"Why are you wearing a wedding dress?"

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By *he Flat CapsCouple
25 weeks ago

Pontypool

Why haven't you fabbed John Wicks pride cock yet?

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By *onameyet2Man
25 weeks ago

chorley

Oh your female, I could have sworn your profile said gay ?

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By *onameyet2Man
25 weeks ago

chorley


"Why are you single?

What are you meant to say? Because I have a doughy physique and off putting personality. Thank you for asking

That is the worst question, hate being asked it! Is there something wrong with being single or something? "

Yes, this is the 1950s after all

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By *ripfillMan
25 weeks ago

havant

Is that leg yours ?

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By *mily36CWoman
25 weeks ago

Beds (or anywhere beginning with B..!?)

Does your other half know your dating?

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By *iltsTSgirlTV/TS
25 weeks ago

chichester

How big is your cock and does it work

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By *cLovin2Man
25 weeks ago

Reading


"Does your other half know your dating?

"

Which one, left or right?

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By *ife NinjaMan
25 weeks ago

Dunfermline

What's that smell?

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By *obilebottomMan
25 weeks ago

All over

Do you like olives?

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By *oldyoudown41Man
25 weeks ago

caledonian

Forgot to take off the wedding ring as a single male on a first encounter ahahahha

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By *ris GrayMan
25 weeks ago

Dorchester

Will you marry me

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By *ot to giggleWoman
25 weeks ago

Coventry


"Would you mind wearing this mask as you look nothing like your pictures?

I have a similar one where I ask her to wear a Tesco carrier bag "

is it a bag for life ?

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By *ris GrayMan
25 weeks ago

Dorchester


"Would you mind wearing this mask as you look nothing like your pictures?

I have a similar one where I ask her to wear a Tesco carrier bag

is she a bag for life ? "

omg probably

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By *ot to giggleWoman
25 weeks ago

Coventry

did you send me your cock pic?

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By *og-ManMan
25 weeks ago

somewhere

Hope you're not on your period..the room is paid for.

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By *sleWightCoupleCouple
25 weeks ago

Ryde

"Why did you throw away a perfectly good pair of knickers when the shit-stain will just wash right out?"

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By *hoirCouple
25 weeks ago

Clacton/Bury St. Edmunds

"Can I see a pic of your mum? I want to see if I will fancy you when you get old."

C

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By *onameyet2Man
25 weeks ago

chorley

Are you embarrassed too dad?

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By *ickie76XXXMan
25 weeks ago

dartford


"Are you embarrassed too dad?"

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By *cLovin2Man
25 weeks ago

Reading


"Would you mind wearing this mask as you look nothing like your pictures?

I have a similar one where I ask her to wear a Tesco carrier bag

is it a bag for life ? "

I'm not wasting a bag for life on an ugly chick, they cost money you know

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By *mily36CWoman
25 weeks ago

Beds (or anywhere beginning with B..!?)


"Does your other half know your dating?

Which one, left or right?"

The 'better' half

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By *cLovin2Man
25 weeks ago

Reading

Sorry I have actually been seeing a few dates, can you put your dic pic on your crotch so I can see what I can expect.

I hope you haven't zoomed into it

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By *nnCeeWoman
25 weeks ago

East of Eden, West of Hell

Can you do me a favour? I, erm, slipped onto a garden gnome earlier and it's gone completely inside me - could you just pop your hand up my arse to see if you can retrieve it?

A&E are getting bored of seeing me after my 'slips'.

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By *atnip make me purrWoman
25 weeks ago

Reading

So when do you want to meet my kids?

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By *olly_chromaticTV/TS
25 weeks ago

Stockport


"So when do you want to meet my kids?"

Second date usually, sometimes third. Has been known on first date

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By *antastic_Mr_Fox_76Man
25 weeks ago

District 13

Going Dutch yes?

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By (user no longer on site)
25 weeks ago

Should we do this again…..

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By *ris GrayMan
25 weeks ago

Dorchester


"did you send me your cock pic? "
no its on the way

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By *ris GrayMan
25 weeks ago

Dorchester

Is that your husband that just came in the room?

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By *ezoMan
25 weeks ago

The Kingdom

Are you up for a threesome with the missus later?

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By (user no longer on site)
25 weeks ago

When is your friend turning up.!!! It was her i wanted to see really

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By *ezoMan
25 weeks ago

The Kingdom

Did you bring condoms or was I supposed to?

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By *eorgesdad69Man
25 weeks ago

nottingham

Do you do anal cos I love being fucked

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By *pdudeMan
25 weeks ago

newtown

Can we be done by 7 pm I need to be home .its a bracelet thing.. and you are over 16 right..

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By *mf123Man
25 weeks ago

with one foot out the door

Never done a date but id ask for a picture of her mum to see what the future holds

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By *aptain V OP   Man
25 weeks ago

Birstall, Leicester

Are you on a diet or do you work out?

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By *ickyKlungespeareMan
25 weeks ago

St Leonards

"I'm sorry to ask, but are you the wife or the husband?"

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By (user no longer on site)
25 weeks ago

Has your cunt ever been torn? If not, do you reckon that’s something you’d like to experience?

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By *ickyKlungespeareMan
25 weeks ago

St Leonards


"Has your cunt ever been torn? If not, do you reckon that’s something you’d like to experience? "

Jeez...that's not awkward - that's your starting pistol!

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By *cLovin2Man
25 weeks ago

Reading


"Has your cunt ever been torn? If not, do you reckon that’s something you’d like to experience? "

I don't have a cunt to tear, but one time a girl was giving me a hand job in the cinema, suddenly the movie ended and in the rush to zip up, I nearly caught my cock in the zip. Does that count?

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By *agatoXXXMan
25 weeks ago

Gone and completely forgotten.

"Has your cunt ever been torn?" You may be entitled to compensation..."

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By (user no longer on site)
25 weeks ago

Wanna split the bill lol

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By (user no longer on site)
25 weeks ago

Have you had an accident that wasn't your fault?

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By *ezoMan
25 weeks ago

The Kingdom

Would you like and subscribe to my YouTube page PrankDates?

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By *ris GrayMan
25 weeks ago

Dorchester

Can i borrow £1354 please

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By *4bimMan
25 weeks ago

Farnborough Hampshire

Are you into the marshmallow thing?

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By *partan69Man
25 weeks ago

hyde

Do you spit or swallow

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By *ucka39Man
25 weeks ago

Newcastle

Have you ever taken it up the bum

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By *ohnny DeeeepMan
25 weeks ago

durham

“You’ve got the same shower curtain as me”

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By *ickyKlungespeareMan
25 weeks ago

St Leonards

When did your breath first become this bad?

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By *ris GrayMan
25 weeks ago

Dorchester

Where are your teeth?

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By (user no longer on site)
25 weeks ago

Here's a keyring for you, I've got a vibrating toy in my ass

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By *ickyKlungespeareMan
25 weeks ago

St Leonards


"Here's a keyring for you, I've got a vibrating toy in my ass "

Would you like to put this vibrating toy in your mouth ?

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By *aptain V OP   Man
25 weeks ago

Birstall, Leicester

How much to sleep with you tonite

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By *westUKguyMan
25 weeks ago

Southport

By any chance are you into nechrophilia ?

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By (user no longer on site)
25 weeks ago

Can I own you?

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By *cLovin2Man
25 weeks ago

Reading


"By any chance are you into nechrophilia ?"

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By *cLovin2Man
25 weeks ago

Reading

Don't take this the wrong way, but did you like used to be a dude?

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By *ickyKlungespeareMan
25 weeks ago

St Leonards

Were you that one person who voted Tory the papers are trying to find?

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By *exycouple.xCouple
25 weeks ago

leeds

Are you into swinging?

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By *nnCeeWoman
25 weeks ago

East of Eden, West of Hell

So, would you rather be buried, or cremated?

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By *obilebottomMan
25 weeks ago

All over

How much? Really?

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By *ensherman333Man
25 weeks ago

Newcastle/Durham

Did you in the past have a cock ?

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By *ulllifeMan
25 weeks ago

perth

Martha???

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By *cLovin2Man
25 weeks ago

Reading

Mum, are you "insatiable cougar seeking young hot stud"?

Whilst typing the above, I just realised whats worse than that.

Gran, are you "insatiable cougar seeking young hot stud"?

I'm sorry, I have issues.

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