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Shouldn't...... but would 😅
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Who is that one person that you know full well you shouldn't fancy or play with but you also know full well you do and if the opportunity arose you'd be straight there without hesitation?
These situations I refer to as:
Shouldn't........ but would 🤣
Spill the beans, I'm all eyes 👀 |
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The only people you shouldn't fancy/play with are relatives.... |
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This is a scary one haha but its someone I'm seeing sister, because I love feet soo much, she always teases me on a sly. Which makes me want to go there but I know I shouldn't. Lol but if the situation arises, I really wouldn't know what to do haha lol |
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By *lfa RomeoMan 2 weeks ago
southeast , Herts, Beds |
My best mates girlfriend, I wouldn't, but God would I love too  |
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By (user no longer on site) 2 weeks ago
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Work colleague (f) |
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My mates mrs.
No idea why. She abit of a one upper when we talk about kinky stuff.
But I have a feeling when it came to it she wouldn't be as wild.
And for some reason I'd like to find out. |
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Oh iv had a few that's why I was curious |
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Of course.....
But I mean like your friends husband or your boss. You know you shouldn't want to, but you do |
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A friends aunt shes absoluty stunning i know i shouldnt but if she gave me a sign id be on it |
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I think alot of people would join you with this one |
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Thanks for been honest, this is perfect |
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Yes! A little mix of pleasure in the workplace |
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Yes! Got to have a nice distraction in your work day |
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Love this!
I find these ones are better in your imagination and wank bank than they would ever live up to if you actually went there as you say,probs all for show |
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By (user no longer on site) 2 weeks ago
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My wife’s nail tech. I messaged to arrange payment as a wee treat and we got chatting and then flirty and then sexting and then………  |
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A customers wife who I have recently found out is on the game. I'd love too as she is stunning but crossing a line somewhat me thinks |
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Oh absolutely AILF doesn't sounds as hot as Milf tho haha |
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I mean.... when lines are drawn we are often provoked into wanting to cross them |
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"I mean.... when lines are drawn we are often provoked into wanting to cross them"
I agree, however I have done lots of work in the house whilst she is there... Think it a thought best kept to myself unfortunately |
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My Mrs best friend. She is openly very naughty and provocative. Given a chance I’d be there...and pretty sure she would as well.. |
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Yeah add it to the bank.
But this is a perfect....... shouldn't, but would.
Thanks for sharing |
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Mmm perfect.
Are you in a swinger relationship? Is a 3some on the cards? |
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A patient but it's unprofessional |
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Oh totally. But a prime example of shouldn't, but would |
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I experienced this years ago and she became my gf and we had to leave our jobs lol was it worth it? A million percent! Still the best I've had by a mile. |
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Amazing!!
Been there too 😅
But once the drama died down and he was no longer my boss I realise I didn't actually fancy him I just got wet over the situation.
Glad it worked out for you! |
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My Ex, we split and I’ve just managed to sort everything and get my own place setup, she came over yesterday to get some signatures and an hour later she was bouncing up and down on top of me. We definitely shouldn’t have done that! |
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I shouldn't sister in law, but I have
Her brother wasn't married to my sister at the time so technically she wasn't my sister in law
But we've seen each other a few times since her brother and my sister have got married and I think she would still like to have some fun again |
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Ohhhhhhhh possibly not. But when you've got familiarity with someone it's hard.
This is more shouldn't, but did. Than shouldn't but would haha.
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[Removed by poster at 05/09/24 11:06:59] |
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One mates sister and mum.
Been lucky enough to have a few of my mates other Halfs and wife's friends. |
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My cousins step daughter…she’s 25 and stunning - she looks like she’s kinky too. |
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How do you mean by looks kinky? Im Curious |
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She has a twinkle in her eye. It’s the way she looks at me too. |
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By *andydan69Man 2 weeks ago
south west nr you mmm |
My best m8s step daughter omfg she wears the hottest Nike pro gear body suits etc n is a proper flirt |
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She's probably thinking the same flirting....... I shouldn't but I'm going to. We love it |
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By *zlakMan 2 weeks ago
Lowestoft |
My mates wife she is so hot. Oh and my mate!  |
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The same mate who's wife you want like a 3some?
Or a diff mate all together ? Hahaha |
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My mrs' mate...I get totally turned on by her |
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By *zlakMan 2 weeks ago
Lowestoft |
"The same mate who's wife you want like a 3some?
Or a diff mate all together ? Hahaha "
Yes the same mate, he doesn't know I'm bi though |
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I have contacted females that guys know on social media to see if they are up for camfun or more. Females they could never approach themselves lol |
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[Removed by poster at 05/09/24 11:43:54] |
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Yes!!! You shouldn't, but you would haha |
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Oh woops. This could be one of those stories where you all get d*unk one night and bang |
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"Dianne Abbott "
H la ha mate seriously wrong lol.
Anyway she wouldnt turn up at the right place lol |
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Awh! That's not a shouldn't but would...
That's just a lack of self confidence.
You never know what people are into unless you ask them |
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Ive had a thing for my ex for years i still think of her often plus went back a few times found her again recently on social media so tempted to have meet up lol |
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Lost my viriginity to my mates Auntie.. if that's relevant haha |
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That's not so much shouldn't but would......
You jumped straight onto shouldn't..... but did hahaha |
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My neighbour opposite me she’s single but looks dirty but a little too close to home |
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Be easy to sneak across on a night if the mood strikes you both tho haha |
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I want to say but I’m paranoid that someone I know might see this ha |
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Only share what your happy to share |
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[Removed by poster at 05/09/24 13:32:14] |
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I learnt a long time ago that all actions have consequences so somehow, I managed to turn my brain off to even thinking that way about someone I shouldn't.
Boring answer I know but on the plus side, gives me the chance to indulge all the ones I would and do  |
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"I learnt a long time ago that all actions have consequences so somehow, I managed to turn my brain off to even thinking that way about someone I shouldn't.
Boring answer I know but on the plus side, gives me the chance to indulge all the ones I would and do "
It's fine in principle but for me it's all forgotten when my wife's neice walks in the room |
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My sister-in-law, I know it's wrong but she's hot |
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By *ucka39Man 2 weeks ago
Newcastle |
A majority of my ex's, it's only sex and it was on another level, but even the other percentage we're great but things didn't go as well
So I'm prepared to give those a miss 😂 |
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My daughters pal she is about 32 now I've wanted to fuck her since she was 18 I met her in the local shop the other week chatted for 10 mins full blown hardon she left me with lol x |
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"Love this!
I find these ones are better in your imagination and wank bank than they would ever live up to if you actually went there as you say,probs all for show"
You are probably right it is best left for a wank.
But it could also turn out to be she is a filth bag and have a great session.
Bet my mate would be alright watching aswell. |
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By (user no longer on site) 2 weeks ago
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My wife’s sister |
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I’d have to say my ex… he had a huge thick cock that I used to really enjoy riding x |
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"I’d have to say my ex… he had a huge thick cock that I used to really enjoy riding x"
I'm guessing mister not be happy? |
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Sounds like a group event on the cards lol |
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Wife's sister seems to be one of the top replies so far |
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Awhhhh.
Let's not park them in the "shouldn't but would"
This is one for your memories and wank bank 🙂 |
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My boss, and 2 colleagues. Defo would. Really should not. But I seem to like women in power positions? Who knew! |
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Hehe I wonder why!!
Yes, definitely should not. But..... when you spend so much time at work you have to find little pleasures along the way |
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"Hehe I wonder why!!
Yes, definitely should not. But..... when you spend so much time at work you have to find little pleasures along the way "
Agree completely! Doubt it'll do my bonus any good though 😉😂 |
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Sisters best friend she is from Ghana and she has big Rita and ass and I would love to ruin both. |
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Well, you'll have to get creative and look at been the most valuable player haha |
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"I’d have to say my ex… he had a huge thick cock that I used to really enjoy riding x
I'm guessing mister not be happy?"
He wouldn’t want me to, just with him being an ex, anyone else he would encourage x |
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I get that. And that's the "shouldnt" part isn't it |
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"I’d have to say my ex… he had a huge thick cock that I used to really enjoy riding x
I'm guessing mister not be happy?
He wouldn’t want me to, just with him being an ex, anyone else he would encourage x"
Lucky girl x |
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"I’d have to say my ex… he had a huge thick cock that I used to really enjoy riding x"
That's one lucky ex |
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Many years ago my mates mum! I was cleaning the toilets after closing one night so I didn’t have to do it the next morning! I heard the side door go and she’d been in earlier but left her jacket and came back for it! I told her to give me 5 mins to finish up and I’d walk her back as we lived a couple of streets away, on the way bag she said she needed to pee and wandered onto the nearby cycle track, with that she hoisted her dress and asked if I liked what I saw! Fucked her there and then against the gate! I was very young and impressionable back then! |
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Sister in law and mother in law 🤦havent but probably would given the chance |
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Definitely shouldn't but would haha |
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Not going there. She's way out of my league, and I'd probably get blocked, so wouldn't be able admire from a distance. |
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That doesn't really count as "shouldn't but would" but okay |
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My work colleagues daughter but he’s more like my mate than anything but she is absolutely stunning and I would set my bride with him on fire for a sniff of a seat she has sat on haha |
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By *rispyDuckMan 2 weeks ago
Chinese Takeaway near you |
"Who is that one person that you know full well you shouldn't fancy or play with but you also know full well you do and if the opportunity arose you'd be straight there without hesitation?
These situations I refer to as:
Shouldn't........ but would 🤣
Spill the beans, I'm all eyes 👀 "
There is this 1 fuck buddy that always calls me at 2 in the morning 😅 she’s pretty toxic but the pussy is 10/10 |
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Sone of those female Republicans who support Donald Trump. Absolute basket cases who are a million miles from me politically but..... |
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It's never satisfying once you do go there. The fantasy is way better than the reality. Lx
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Anybody good looking today to be honest. But I can’t get the boss out of my mind. ‘So wrong’ |
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Stupidly or luckily depending how you look at it had a fling with a married boss and also had one of my exs sisters after finding the ex had cheated |
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Honest here..... my best friends mrs 🙈 but I know she feels the same |
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Definitely sister in law…… came close a few times but never quite sealed the deal |
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"Honest here..... my best friends mrs 🙈 but I know she feels the same "
What are you waiting for? |
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"Anybody good looking today to be honest. But I can’t get the boss out of my mind. ‘So wrong’"
love it |
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"Sister in law and mother in law 🤦havent but probably would given the chance "
Keep it in the family. Why not?! |
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My cousin shouldn’t but definitely would |
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By *obwhateverMan 2 weeks ago
Stirling/ London/ Yorkshire |
A certain female politician whose party, ideology, and policies I loathe with every fibre of my being.
Would though. |
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My ex wife's Aunty. She's only about 5 years older than me, we always flirted and I have a feeling that she could be very adventurous if she got the chance. |
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Step sons ex gf.... Shouldn't but fuck I would |
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My senior boss. I shouldnt. But given half a chance i most definitely would 😈😈 |
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"My senior boss. I shouldnt. But given half a chance i most definitely would 😈😈"
You mink..
Male or female..?
Mrs.. |
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"It's never satisfying once you do go there. The fantasy is way better than the reality. Lx
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I’d have to disagree. I fantasised about my mates dad for years, and when it finally happened it was out of this world annd turned into a months long fling. I still think of it fondly now and the reality was definitely better than the fantasy |
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Matron of honour at sons wedding....shouldn't....(but did)! |
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Former FWB daughter, couple Mexican ladies at work, one is pregnant. A janitor from work, tall lady from Namibia. |
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"My senior boss. I shouldnt. But given half a chance i most definitely would 😈😈
You mink..
Male or female..?
Mrs.."
Male |
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My oldest friend's fiance! Had a bit of a kiss at a club when we were about 19 and before they got together and haven't stopped thinking about her since!
Pretty sure she is actually straight though and would never in a million years think of suggesting anything haha
But Grace, if you ever see this...... Haha xx |
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Girl at the local Costa, she makes a mean hot chocolate too |
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Ooh a hot priest I saw a couple of weeks ago |
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Mrs’ best friend. We fucked before i met my mrs but would love to again x |
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My mates wife, wow she is hot!! |
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Neighbours are always a good one |
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Oh god yeah toxic but you still would haha |
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By *end1Man 2 weeks ago
southend on sea |
A good few years ago I managed to bed my new single female neighbour within 10 hours of moving in. |
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"My oldest friend's fiance! Had a bit of a kiss at a club when we were about 19 and before they got together and haven't stopped thinking about her since!
Pretty sure she is actually straight though and would never in a million years think of suggesting anything haha
But Grace, if you ever see this...... Haha xx"
Does she know that you’re bi-curious? If not maybe try and weave that into a conversation and that you swing… she may want to explore |
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Always worth having the conversation haha |
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"My mates wife, wow she is hot!! "
My mate told me he'd do my wife - but she declined |
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My Aunt, my mums sister ! I’ve always wanted to bury my head on her tits and love to look down as she’s sucking me and see her hoover over me guiding me in her arse xxx because her pussy is for my uncle onlyx |
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The boss colleague always surprises me, I’ve been a manager for years, in fairness in that time I’ve never wanted to hook with any colleague but the hr nightmare if I made move and it backfired is such a mood kill.
I would almost need the colleague to strip to think ‘yeah she’s interested’ to make a move.
Feel just not for me |
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PM me with your Shouldnt but Would fantasies. I have an interesting idea |
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Mates brothers daughter, so fucking hot it’s crazy  |
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A old friend that I met through swinging scene - we never have played but I always have thought what would it be like
We went though a stag when I told her I would like to meet have have sex but now she has settled down with a vanilla |
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By (user no longer on site) 2 weeks ago
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My friends dad! Such a dilf haha |
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We're very open,nothing better than telling each other what you would love to do to someone elseX |
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Thanks for keeping the thread entertaining!
Anymore for anymore? 🤓 |
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Ex sis in law all day lol and my best mate s hot wife
Many other s too lol |
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Much younger, curvy Namibian janitor at work. |
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My mates smoking hot mum…. Banging body from head to toe. Many Years ago I was at his and went upstairs and watched her dry off…. She’s still a stunner to this day… 🔥 |
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We ended up sleeping with V's best friend (female) a few times. We now vow and recommend to swinger friends never to sleep with friends. |
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Slept with a best mates mum. Needless to day we ain't friends anymore baba |
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"We ended up sleeping with V's best friend (female) a few times. We now vow and recommend to swinger friends never to sleep with friends. "
Lol |
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By *oe15Man 11 hours ago
Belfast |
Who's up for hot chat?
Telegram preferred.
Love other married guys
Anything goes |
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