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Naughtiest person you've had sex with.
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By (user no longer on site) OP
over a year ago
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Following on from Naughtiest place you've had sex. Who is the Naughtiest person uve had sexy with. Like ur sister in law , bosses wife, work college, teacher, ur parents ex. Etc. |
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A friend's (also work colleague) mum. She was (and still is married).
I remember doing her in hotel while she was on phone to her husband and asking doing her in her house while friend was sleeping and hubby was working.
Total MILF and one of the best pieces of ass I ever tapped.
Did feel a bit guilty afterwards even if she did make all the moves. There was only so much I could resist before I gave in. |
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By (user no longer on site)
over a year ago
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I was doing some repair work in house I had finished the work it happened to be in the bedroom when I turned around there she was starkers I still haven't got paid lol |
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"My aunt once gave me a blowie at a wedding
Ohh I wouldn't brag about that one... " yeaaàaa fuck that shit, that is like fucking a sister or mum and saying waooo that was the naughtiest thing I ever did |
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By (user no longer on site)
over a year ago
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Want to say my friends mom but never closed the deal
She was so sexually suggestive when I was a teen, going around thong showing and see thru light pants bending over and things I now recognise as flirtatious.
I'm not sure did she just get a kick from turning on 17/18 year olds or what the deal was, I touched her ass a couple of times and she didn't seem to mind me doing it at all but never anything more.
She is about 50 now, not the milf she once was but still hot and a sexy air about her.
Not sure on the status of her marriage now I think it is not still as it was anyway. Her son though is a great friend but lives abroad I'm still nearby her place.... |
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"My aunt once gave me a blowie at a wedding
Ohh I wouldn't brag about that one... yeaaàaa fuck that shit, that is like fucking a sister or mum and saying waooo that was the naughtiest thing I ever did "
Not necessarily. If the Aunt wasn't a blood relative, if the uncle was the blood relative and it were his wife then that is a lot different. Still "immoral" depending on how people view it (family values and morals etc). The immorality of it boils down to bloodline. Was it an Aunt by blood or an Aunt through marriage? There IS a huge difference. |
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By (user no longer on site)
over a year ago
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"Want to say my friends mom but never closed the deal
She was so sexually suggestive when I was a teen, going around thong showing and see thru light pants bending over and things I now recognise as flirtatious.
I'm not sure did she just get a kick from turning on 17/18 year olds or what the deal was, I touched her ass a couple of times and she didn't seem to mind me doing it at all but never anything more.
She is about 50 now, not the milf she once was but still hot and a sexy air about her.
Not sure on the status of her marriage now I think it is not still as it was anyway. Her son though is a great friend but lives abroad I'm still nearby her place...."
Did we have the same friend? Lol
Looking back now all the signs were there |
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By (user no longer on site)
over a year ago
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"Want to say my friends mom but never closed the deal
She was so sexually suggestive when I was a teen, going around thong showing and see thru light pants bending over and things I now recognise as flirtatious.
I'm not sure did she just get a kick from turning on 17/18 year olds or what the deal was, I touched her ass a couple of times and she didn't seem to mind me doing it at all but never anything more.
She is about 50 now, not the milf she once was but still hot and a sexy air about her.
Not sure on the status of her marriage now I think it is not still as it was anyway. Her son though is a great friend but lives abroad I'm still nearby her place....
Did we have the same friend? Lol
Looking back now all the signs were there "
Haha yes for sure, I'd say she wouldn't actually have gone thru with anything just enjoyed being wank bank material id say.
I'd love to try hit up something with her now but don't know how to initiate |
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"Want to say my friends mom but never closed the deal
She was so sexually suggestive when I was a teen, going around thong showing and see thru light pants bending over and things I now recognise as flirtatious.
I'm not sure did she just get a kick from turning on 17/18 year olds or what the deal was, I touched her ass a couple of times and she didn't seem to mind me doing it at all but never anything more.
She is about 50 now, not the milf she once was but still hot and a sexy air about her.
Not sure on the status of her marriage now I think it is not still as it was anyway. Her son though is a great friend but lives abroad I'm still nearby her place....
Did we have the same friend? Lol
Looking back now all the signs were there "
I can relate. I had a friend who had an extremely hot mum and I remember her doing things like bending over in front of me etc and at time I didn't realise but looking back now I realise she was giving me signals and I still kick myself to this day for not realising. Lol |
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"Want to say my friends mom but never closed the deal
She was so sexually suggestive when I was a teen, going around thong showing and see thru light pants bending over and things I now recognise as flirtatious.
I'm not sure did she just get a kick from turning on 17/18 year olds or what the deal was, I touched her ass a couple of times and she didn't seem to mind me doing it at all but never anything more.
She is about 50 now, not the milf she once was but still hot and a sexy air about her.
Not sure on the status of her marriage now I think it is not still as it was anyway. Her son though is a great friend but lives abroad I'm still nearby her place....
Did we have the same friend? Lol
Looking back now all the signs were there
Haha yes for sure, I'd say she wouldn't actually have gone thru with anything just enjoyed being wank bank material id say.
I'd love to try hit up something with her now but don't know how to initiate "
Just drop a simple note through her door (with number) saying hey it's been years etc but you remember her as you used to enjoy the chats and as you're not living so far away would she fancy a coffee and catchup sometime. It's honest, non creepy and to the point. If you hear nothing back, no harm done. If you do then see how the first meeting goes.
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By (user no longer on site)
over a year ago
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"Want to say my friends mom but never closed the deal
She was so sexually suggestive when I was a teen, going around thong showing and see thru light pants bending over and things I now recognise as flirtatious.
I'm not sure did she just get a kick from turning on 17/18 year olds or what the deal was, I touched her ass a couple of times and she didn't seem to mind me doing it at all but never anything more.
She is about 50 now, not the milf she once was but still hot and a sexy air about her.
Not sure on the status of her marriage now I think it is not still as it was anyway. Her son though is a great friend but lives abroad I'm still nearby her place....
Did we have the same friend? Lol
Looking back now all the signs were there
Haha yes for sure, I'd say she wouldn't actually have gone thru with anything just enjoyed being wank bank material id say.
I'd love to try hit up something with her now but don't know how to initiate
Just drop a simple note through her door (with number) saying hey it's been years etc but you remember her as you used to enjoy the chats and as you're not living so far away would she fancy a coffee and catchup sometime. It's honest, non creepy and to the point. If you hear nothing back, no harm done. If you do then see how the first meeting goes.
"
I still see her a few times a year and have her number, I'm only walking distance from her house.... |
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By (user no longer on site)
over a year ago
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Seen her recently at my mates 30th and was all hugs and telling me how good I look, she's divorced now too I'd say a few drinks and some privacy and I could make it happen |
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By (user no longer on site)
over a year ago
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"Want to say my friends mom but never closed the deal
She was so sexually suggestive when I was a teen, going around thong showing and see thru light pants bending over and things I now recognise as flirtatious.
I'm not sure did she just get a kick from turning on 17/18 year olds or what the deal was, I touched her ass a couple of times and she didn't seem to mind me doing it at all but never anything more.
She is about 50 now, not the milf she once was but still hot and a sexy air about her.
Not sure on the status of her marriage now I think it is not still as it was anyway. Her son though is a great friend but lives abroad I'm still nearby her place....
Did we have the same friend? Lol
Looking back now all the signs were there
Haha yes for sure, I'd say she wouldn't actually have gone thru with anything just enjoyed being wank bank material id say.
I'd love to try hit up something with her now but don't know how to initiate
Just drop a simple note through her door (with number) saying hey it's been years etc but you remember her as you used to enjoy the chats and as you're not living so far away would she fancy a coffee and catchup sometime. It's honest, non creepy and to the point. If you hear nothing back, no harm done. If you do then see how the first meeting goes.
I still see her a few times a year and have her number, I'm only walking distance from her house...."
The thing is how do I put it out there in a way that would create future awkwardness? Can't really ask her out, we live in a small place in Ireland where u would have to go 200 miles to have some chance of anonymity ha |
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By (user no longer on site)
over a year ago
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"Seen her recently at my mates 30th and was all hugs and telling me how good I look, she's divorced now too I'd say a few drinks and some privacy and I could make it happen "
Defo Man U are in there, give it a go. I have been with an older woman before and they are no nonsense from what I see but putting your neck out with someone u know is a bit different for me |
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"Seen her recently at my mates 30th and was all hugs and telling me how good I look, she's divorced now too I'd say a few drinks and some privacy and I could make it happen
Defo Man U are in there, give it a go. I have been with an older woman before and they are no nonsense from what I see but putting your neck out with someone u know is a bit different for me"
Again, keeping it simple is always best way. If you have her number then a simple text saying it's been quite a while and you were thinking back to such and such a time (insert funny memory) which got you wondering how she is and then ask if she fancies a cuppa and catchup. What's the worst can happen? You asked for a cuppa and a chat. You can't possibly be ridiculed of thought badly of for that. You're overthinking it buddy which is understandable. A short simple text. |
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"Cheers yes when u put it that way I am haha.
I'll work on it and see when would be a good time soon to approach "
I hope someday soon you are posting on here telling us about the great sex you're having with her.
Think of it this way. Even if you text asking for a cuppa or whatever..... ok she might think is he coming unto me.... but she has no way of possibly knowing as all you have done is ask for a cuppa and a catchup so she has to give the benefit of the doubt. It would be different if you sent her a dirty or flirty message. |
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I actually have a similar dilemma.
Years ago when playing a drinking game as a dare I had to phone a friend's mom and tell her I fancy her etc. She's been single for years. To my surprise though she actually was flirting back and said I'd gotten her horny and wet and that she would eat me for breakfast given a chance. Bit of unfinished business there. She actually lives literally one street away and now this whole chat has gotten me thinking. Lol
I don't have her number though. Hmmmmmmm. |
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By (user no longer on site)
over a year ago
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"I actually have a similar dilemma.
Years ago when playing a drinking game as a dare I had to phone a friend's mom and tell her I fancy her etc. She's been single for years. To my surprise though she actually was flirting back and said I'd gotten her horny and wet and that she would eat me for breakfast given a chance. Bit of unfinished business there. She actually lives literally one street away and now this whole chat has gotten me thinking. Lol
I don't have her number though. Hmmmmmmm. "
Is she good looking?
How do u know she didn't know it was a prank call and was just playing along? |
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"I actually have a similar dilemma.
Years ago when playing a drinking game as a dare I had to phone a friend's mom and tell her I fancy her etc. She's been single for years. To my surprise though she actually was flirting back and said I'd gotten her horny and wet and that she would eat me for breakfast given a chance. Bit of unfinished business there. She actually lives literally one street away and now this whole chat has gotten me thinking. Lol
I don't have her number though. Hmmmmmmm.
Is she good looking?
How do u know she didn't know it was a prank call and was just playing along?"
I just know from the call that she was being serious and thought I was serious. I wouldn't say she is proper MILF material but it's just that whole taboo naughtiness factor is the turn on. Have been a few times since that we passed each other on the street and once when I was with my mother and they were chatting then as we walked off her and I both gave each other that knowing look. |
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By (user no longer on site)
over a year ago
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This one near me that I was talking about is/was proper MILF material, she isnt as hot not as she once was even up to 2 years ago, she is about 50 now.
We get on great and could talk for hours, I'll have to have an excuse to bump into her and I'll let u know how it goes |
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"This one near me that I was talking about is/was proper MILF material, she isnt as hot not as she once was even up to 2 years ago, she is about 50 now.
We get on great and could talk for hours, I'll have to have an excuse to bump into her and I'll let u know how it goes "
Do it man. Life's too short. We miss all off the chances that we don't take. Lol
I'm gonna go work on this other one at same time. Let's see who can get there first. Lol |
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By (user no longer on site)
over a year ago
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You're on!
Step 1 open a dialogue
2 change her old image of me as a young immature teen and interest her
3 drop indications of interest and create a sexual tension
4 seal the deal |
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"You're on!
Step 1 open a dialogue
2 change her old image of me as a young immature teen and interest her
3 drop indications of interest and create a sexual tension
4 seal the deal"
Oh gawd, the only way it could be even better is if you discovered she is actually on Fab. Lol |
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By (user no longer on site)
over a year ago
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Women I met on a night out. She was 40 and I was about 25 and she was incredibly hot. Fucked her all night and the next morning
She also gave incredible head |
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By (user no longer on site)
over a year ago
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"This one near me that I was talking about is/was proper MILF material, she isnt as hot not as she once was even up to 2 years ago, she is about 50 now.
We get on great and could talk for hours, I'll have to have an excuse to bump into her and I'll let u know how it goes
Do it man. Life's too short. We miss all off the chances that we don't take. Lol
I'm gonna go work on this other one at same time. Let's see who can get there first. Lol"
Went to call over yesterday and her husband was out cutting the lawn This may be harder than I thought |
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By (user no longer on site)
over a year ago
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"My son's best friend
Alex a true MILF
My best friend was older than me in my defence... And first time I had sex with him didn't know he was her son "
Ahh so it was your friends son and not your sons best friend Alex ??- |
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By (user no longer on site)
over a year ago
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"A guy the night before his wedding , we had a few kisses and i was at the wedding and the day after it , well we ended up very naughty but he came looking for me , kinda regret it now it was a long time ago , he still happily married , thank god
Mrs crazy
Naughty woman Mrs Crazy hehe "
Very naughty x |
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By (user no longer on site)
over a year ago
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"My son's best friend
Alex a true MILF
My best friend was older than me in my defence... And first time I had sex with him didn't know he was her son
Ahh so it was your friends son and not your sons best friend Alex ??-"
She was my friend.... Didn't know her son personally, she became my best friend after and then I found out and met her son and daughter at a party in her house... Bit awkward.
|
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By (user no longer on site)
over a year ago
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"My son's best friend
Alex a true MILF
My best friend was older than me in my defence... And first time I had sex with him didn't know he was her son
Ahh so it was your friends son and not your sons best friend Alex ??-"
Yeah the sorry... Bad wording there
gloria(modern family) moment there |
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By *j47Man
over a year ago
limerick |
"My son's best friend
Alex a true MILF
My best friend was older than me in my defence... And first time I had sex with him didn't know he was her son
Ahh so it was your friends son and not your sons best friend Alex ??-
Yeah the sorry... Bad wording there
gloria(modern family) moment there "
Pmsi I can just imagine u as gloria that ass wiggling as u walk away |
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By (user no longer on site)
over a year ago
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"My son's best friend
Alex a true MILF
My best friend was older than me in my defence... And first time I had sex with him didn't know he was her son
Ahh so it was your friends son and not your sons best friend Alex ??-
She was my friend.... Didn't know her son personally, she became my best friend after and then I found out and met her son and daughter at a party in her house... Bit awkward.
"
Love it !!! |
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By (user no longer on site)
over a year ago
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"My son's best friend
Alex a true MILF
My best friend was older than me in my defence... And first time I had sex with him didn't know he was her son
Ahh so it was your friends son and not your sons best friend Alex ??-
Yeah the sorry... Bad wording there
gloria(modern family) moment there
Pmsi I can just imagine u as gloria that ass wiggling as u walk away "
Haha Cj, ohh wish I had that face and body(and her real life husband) .... Only accent and her " not to smart remarks" |
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By (user no longer on site)
over a year ago
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"My son's best friend
Alex a true MILF
My best friend was older than me in my defence... And first time I had sex with him didn't know he was her son
Ahh so it was your friends son and not your sons best friend Alex ??-
Yeah the sorry... Bad wording there
gloria(modern family) moment there
Pmsi I can just imagine u as gloria that ass wiggling as u walk away
Haha Cj, ohh wish I had that face and body(and her real life husband) .... Only accent and her " not to smart remarks" "
Wait, so you have a Columbian accent Alex? |
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By (user no longer on site)
over a year ago
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"My son's best friend
Alex a true MILF
My best friend was older than me in my defence... And first time I had sex with him didn't know he was her son
Ahh so it was your friends son and not your sons best friend Alex ??-
Yeah the sorry... Bad wording there
gloria(modern family) moment there
Pmsi I can just imagine u as gloria that ass wiggling as u walk away
Haha Cj, ohh wish I had that face and body(and her real life husband) .... Only accent and her " not to smart remarks"
Wait, so you have a Columbian accent Alex?"
Kinda |
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By (user no longer on site)
over a year ago
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"My aunt once gave me a blowie at a wedding
Ohh I wouldn't brag about that one... yeaaàaa fuck that shit, that is like fucking a sister or mum and saying waooo that was the naughtiest thing I ever did "
I think he worded in a taboo sense!!
Not all aunts are blood related |
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By (user no longer on site)
over a year ago
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Also I've a uncle (blood related) he got married.. 2nd marriage.. She's much younger early 40's.. Stunning lady..
She's my aunt once removed
You'd have trouble removing her if she became accidently impaled on my cock |
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By (user no longer on site)
over a year ago
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"My son's best friend
Alex a true MILF
My best friend was older than me in my defence... And first time I had sex with him didn't know he was her son
Ahh so it was your friends son and not your sons best friend Alex ??-
Yeah the sorry... Bad wording there
gloria(modern family) moment there
Pmsi I can just imagine u as gloria that ass wiggling as u walk away
Haha Cj, ohh wish I had that face and body(and her real life husband) .... Only accent and her " not to smart remarks"
Wait, so you have a Columbian accent Alex?
Kinda "
Kinda? Maybe I should be asking if you have the feisty, fiery Latin temperament and passion rather, and would you consider showing a little of that passion to a lovely fella like myself? |
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By (user no longer on site)
over a year ago
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"My son's best friend
Alex a true MILF
My best friend was older than me in my defence... And first time I had sex with him didn't know he was her son
Ahh so it was your friends son and not your sons best friend Alex ??-
Yeah the sorry... Bad wording there
gloria(modern family) moment there
Pmsi I can just imagine u as gloria that ass wiggling as u walk away
Haha Cj, ohh wish I had that face and body(and her real life husband) .... Only accent and her " not to smart remarks"
Wait, so you have a Columbian accent Alex?
Kinda
Kinda? Maybe I should be asking if you have the feisty, fiery Latin temperament and passion rather, and would you consider showing a little of that passion to a lovely fella like myself? "
Haha ask Eddie about that fiery temperament |
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"My son's best friend
Alex a true MILF
My best friend was older than me in my defence... And first time I had sex with him didn't know he was her son
Ahh so it was your friends son and not your sons best friend Alex ??-
She was my friend.... Didn't know her son personally, she became my best friend after and then I found out and met her son and daughter at a party in her house... Bit awkward.
"
Haha, would have loved to have seen the look on his face and yours. Wonder what he was thinking at that time. Lol
Did he say anything to you afterwards? |
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