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  #4741  
Old 25-06-2023, 03:50 PM
terwong terwong is offline
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Re: Anyone u sex with before that u never thought of....

Quote:
Originally Posted by imom View Post
Thought there was another similar thread.... but this one brought back those memories again.

Have been very naughty all my life but this is the one that will banish me to hell...

I did my wife's maid of honour.

Not at the wedding of course... But there was another 'offer' on the table from another lady at the wedding, which I didn't take up, but that's another story...

Other less naughty (but still unexpected) ones:
- boss' secretary
- tutee's mum
- my property agent
- girl brought by friend to a party but ended up with me

There was also this group of guys and girls who I used to drink with. There were six or seven girls in that group and I went through three of them at different times... Wonder if they ever exchanged notes... haha...
Spill the beans on your encounters with the maid of honour, property agent (part of the deal to close your transaction?) and the one in the group you eyed from the outset
  #4742  
Old 25-06-2023, 05:03 PM
ceeko ceeko is offline
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Re: Anyone u sex with before that u never thought of....

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Originally Posted by transient View Post
Chinese girl?
Yes heh .. u bonked her before? maybe u did. heh
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  #4743  
Old 26-06-2023, 09:16 AM
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Re: Anyone u sex with before that u never thought of....

Quote:
Originally Posted by terwong View Post
Spill the beans on your encounters with the maid of honour, property agent (part of the deal to close your transaction?) and the one in the group you eyed from the outset
Can't kiss and tell lah... not the details anyway, since some friends might be able to guess identities...

Property agent - I knew her before she became one. Always had some sexual tension I guess... and property deal was closed long before it happened. Would never leverage any friend like that, haha... It was some catch-up drinks, we got high and it happened. Quite a common encounter in that sense. I just did not expect it.

The one in the drinking group I was eyeing - she is my friend's sister. Friend actually thought of hooking us up before, but we were in different countries due to work. We were introduced while she was on holiday in Sg (but still based overseas) - which is when I brought her into the drinking group. We had been flirting on and off over cyberspace and when she finally came to Sg, we sealed the deal... quite a few times over

As for maid of honour... I actually knew her before my wife. Never really thought of her that way, which contributed to the 'unexpectedness'. I was helping her with something at her place (can't say what - that would be too revealing ) - It was nothing sexual, but it involved some physical contact... Guess there were some unexpected sparks. We managed to resist that day, but eventually succumbed a couple of meetings later...
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  #4744  
Old 26-06-2023, 04:20 PM
terwong terwong is offline
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Re: Anyone u sex with before that u never thought of....

Quote:
Originally Posted by imom View Post
Can't kiss and tell lah... not the details anyway, since some friends might be able to guess identities...

Property agent - I knew her before she became one. Always had some sexual tension I guess... and property deal was closed long before it happened. Would never leverage any friend like that, haha... It was some catch-up drinks, we got high and it happened. Quite a common encounter in that sense. I just did not expect it.

The one in the drinking group I was eyeing - she is my friend's sister. Friend actually thought of hooking us up before, but we were in different countries due to work. We were introduced while she was on holiday in Sg (but still based overseas) - which is when I brought her into the drinking group. We had been flirting on and off over cyberspace and when she finally came to Sg, we sealed the deal... quite a few times over

As for maid of honour... I actually knew her before my wife. Never really thought of her that way, which contributed to the 'unexpectedness'. I was helping her with something at her place (can't say what - that would be too revealing ) - It was nothing sexual, but it involved some physical contact... Guess there were some unexpected sparks. We managed to resist that day, but eventually succumbed a couple of meetings later...
I had a hunch the maid of honour was a case where you were acquainted/met/dated before you met your wife. If so, why would you say you'd be banished to hell for that? You continued after hooking up with your wife (and I presumed she introduced you to her)?

PS: You could always write your own story with key details altered/embellished like what's at https://sammyboy.today/showthread.php?t=909591
  #4745  
Old 26-06-2023, 11:25 PM
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Re: Anyone u sex with before that u never thought of....

Quote:
Originally Posted by terwong View Post
I had a hunch the maid of honour was a case where you were acquainted/met/dated before you met your wife. If so, why would you say you'd be banished to hell for that? You continued after hooking up with your wife (and I presumed she introduced you to her)?

PS: You could always write your own story with key details altered/embellished like what's at https://sammyboy.today/showthread.php?t=909591
Haha I've said as much as I can, without revealing too many details that could be quite unique. In fact, I'm thinking that not many would have done their wives' MOH in the first place, so already quite risky. Not really into embellishing and changing facts too. Just sharing some short snippets and not a writer of long stories
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Schrodinger's Cat - A girl's skills are both good and bad until one makes an observation. Then she becomes either 'good' or 'bad'. The observation thus determines the result
  #4746  
Old 27-06-2023, 06:14 AM
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Re: Anyone u sex with before that u never thought of....

Quote:
Originally Posted by ceeko View Post
Yes heh .. u bonked her before? maybe u did. heh
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  #4747  
Old 17-07-2023, 12:37 PM
KimSiew769 KimSiew769 is offline
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Re: Anyone u sex with before that u never thought of....

Met this 32 year old OL Jacqueline from dating app - met for drinks a few times. One night send her home and she asked if i could "escort" her up as she had a previous scare of seeing a man sitting at the staircase on her level.

We went up without incident and started kissing outside her unit - her mum came back unexpectantly and saw us, she was extremely friendly and scolded her for not inviting me in. so we went in and her mum went straight to her room and came out 20 mins later changed into a oversize tee and with some clothing in her arms - saw her dump them onto the laundry basket in the kitchen and then went back her room leaving us in the living. we kissed in the sofa with the TV on.

As usual i went to the toilet before leaving, passed by the laundry basket and digged into the pile of clothes her mum just left - inside the bundle was a pair of nude bra and a green lace trimmed thong - i took it and stuffed it into my pocket (later at home i found fresh wet stains on her panties)

Anyway, a few days later i met Jacq for drinks and she suggest going to her house to watch Netflix series that we both followed. Her mum was home but welcomed us - she is extremely friendly and chat with me, in my mind i had the green lace thong on her and her stains that i licked up that day while playing with it.

Anyway, her mum left to meet her colleagues after awhile leaving me and Jacq alone in the house - we cuddle and fucked twice that day..

so it became a regular affair for me to drop by her place, her mum will sometimes cook for us, but since the first night, i dont find her mum's intimates in the laundry basket anymore.

One day, i went over her place after work - Jacq was not back yet as she is stuck at work (she drives so i didnt pick or meet her from work) - He mum was home and we chat in the living room like old friends (not as the mother of the girl i am fucking) - the conversation came to her asking me if i am aware Jacq is seeing someone, i told her i knew she was seeing her colleague for a few years.

Her mum Lilian (54 yr old) then started to tell me her worries about them, like how the man is married and how Jacq was happy seeing him - her mum asked me how i felt knowing i am seeing someone who is in such a mess.

I told her honestly that we are FB, and we have agreed to live our own lives and only meet for sex. Lilian asked if i am fucking others? i lied and say no of course .. she smiled (i think she knows i am lying) and ask me to be careful if i am fucking others (use protection etc)

So i turned my question back to her and ask is she seeing anyone, she told me she is seeing a guy for sex only (turns out that guy is the same age as me) -- i am quite surprised she is so open with me, so we chat on the topic of FB

I dont know who initiated it but we kissed and from then it was a point of no return, knowing Jacq might be back soon, i caressed her breast through her tee, i could feel her seamless t-shirt bra, she moaned when i did that.. she was very open, her hands was on my rod fondling me through my pants.. i thought maybe i could fuck her before Jacq comes back

But she suddenly pushed me away, and told me Jacq will be home soon and went into her bedroom. i sat there not knowing what i should do, go in? or just wait for Jacq... When Jacq was back 1 hr later (imagine me sitting on the sofa for the long 1 hr) Lilian came out and pretended like nothing happened.

That evening i fucked Jacq in her room, i pumped her so hard cause I wanted her to moan (so her mum could hear her) and she did (more in a rebellious way) - she was literally screaming.

After that i came out for a shower and grab a drink at the kitchen, her mum came out and saw me, she smile at me cheekily and hit my butt when she walk passed.

From then on, it was a strange feeling whenever i was in Jacq's place - lusting for her mum while i was fucking Jacq... i became like a family fren, going over on sat whether Jacq is home or not.

One day Jacq told me, the guy he is seeing is leaving his family for her - i asked if she wants to stop the FB arrangment, she told me she wants me to continue being her frens but not FB.. i told her i am ok, if she wants me to hang ard.

after a few weeks, Jacq and me stopped fucking - she was serious about her colleague - but i still drop by occasionally at her place. One sat, Jacq was away on stayucation with him, i didnt know until i was at her place and her mum told me - she asked me if i feel jealous, i told her no and i am happy for her

Lilian asked me to help her remove the curtains in her room so she could wash them and while i was doing that standing on the stool, she touched me on my thigh and ask if i want to fucked. I stopped what i was doing, and came down - i push her onto her bed and pull her tee up and attacked her breast, she was wearing a bright red lace bra (seems like she is prepared) and i pull the left cup down and started sucking her nipples

Unlike Jacq, Lilian was quiet when i sucked her, she lift her head to look at me while i sucked her, she keeps mumbling to herself "oh gosh, what are you doing?" she had the biggest areola i have seen, so big and her nipples are gigantic huge

soon, both her bra cup was pushed down and i was sucking them both while fondling her pussy - she was wearing a denim shorts, so i unbutton it and pull it away - as expected she was wearing a bright red lace panties (matching pair) and her crotch area was soaked! like as if she pee on her panty

i caress her there, she didnt moan but keep looking at what i was doing - i wanted to go down on her but she stopped me - she turn me over and let me lay on her bed, and soon she was sucking me and making noises (not moaning) while she was sucking me

she was not as sensual as Jacq who enjoys foreplay, she moved up and sat onto me and started moving her body with my rod inside her - she was bouncing up and down on me and watch her breast bounce was making me about to cum - i told her and she ask me to come up and penetrate her missionary - i pump her so hard that she started screaming and she keep saying "oh gosh! oh Gosh!!"

i cum inside her, i dont think she came... we kissed and wipe my cum on her pussy - and washed up... i lay on her bed for awhile looking at the hald removed curtains ..

when i was leaving, Jacq came home - i think she kinda guessed what happened . . that cheeky smile she had on her face
  #4748  
Old 17-07-2023, 01:37 PM
pinyon72 pinyon72 is offline
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Re: Anyone u sex with before that u never thought of....

Quote:
Originally Posted by KimSiew769 View Post
Met this 32 year old OL Jacqueline from dating app - met for drinks a few times. One night send her home and she asked if i could "escort" her up as she had a previous scare of seeing a man sitting at the staircase on her level.

We went up without incident and started kissing outside her unit - her mum came back unexpectantly and saw us, she was extremely friendly and scolded her for not inviting me in. so we went in and her mum went straight to her room and came out 20 mins later changed into a oversize tee and with some clothing in her arms - saw her dump them onto the laundry basket in the kitchen and then went back her room leaving us in the living. we kissed in the sofa with the TV on.

As usual i went to the toilet before leaving, passed by the laundry basket and digged into the pile of clothes her mum just left - inside the bundle was a pair of nude bra and a green lace trimmed thong - i took it and stuffed it into my pocket (later at home i found fresh wet stains on her panties)

Anyway, a few days later i met Jacq for drinks and she suggest going to her house to watch Netflix series that we both followed. Her mum was home but welcomed us - she is extremely friendly and chat with me, in my mind i had the green lace thong on her and her stains that i licked up that day while playing with it.

Anyway, her mum left to meet her colleagues after awhile leaving me and Jacq alone in the house - we cuddle and fucked twice that day..

so it became a regular affair for me to drop by her place, her mum will sometimes cook for us, but since the first night, i dont find her mum's intimates in the laundry basket anymore.

One day, i went over her place after work - Jacq was not back yet as she is stuck at work (she drives so i didnt pick or meet her from work) - He mum was home and we chat in the living room like old friends (not as the mother of the girl i am fucking) - the conversation came to her asking me if i am aware Jacq is seeing someone, i told her i knew she was seeing her colleague for a few years.

Her mum Lilian (54 yr old) then started to tell me her worries about them, like how the man is married and how Jacq was happy seeing him - her mum asked me how i felt knowing i am seeing someone who is in such a mess.

I told her honestly that we are FB, and we have agreed to live our own lives and only meet for sex. Lilian asked if i am fucking others? i lied and say no of course .. she smiled (i think she knows i am lying) and ask me to be careful if i am fucking others (use protection etc)

So i turned my question back to her and ask is she seeing anyone, she told me she is seeing a guy for sex only (turns out that guy is the same age as me) -- i am quite surprised she is so open with me, so we chat on the topic of FB

I dont know who initiated it but we kissed and from then it was a point of no return, knowing Jacq might be back soon, i caressed her breast through her tee, i could feel her seamless t-shirt bra, she moaned when i did that.. she was very open, her hands was on my rod fondling me through my pants.. i thought maybe i could fuck her before Jacq comes back

But she suddenly pushed me away, and told me Jacq will be home soon and went into her bedroom. i sat there not knowing what i should do, go in? or just wait for Jacq... When Jacq was back 1 hr later (imagine me sitting on the sofa for the long 1 hr) Lilian came out and pretended like nothing happened.

That evening i fucked Jacq in her room, i pumped her so hard cause I wanted her to moan (so her mum could hear her) and she did (more in a rebellious way) - she was literally screaming.

After that i came out for a shower and grab a drink at the kitchen, her mum came out and saw me, she smile at me cheekily and hit my butt when she walk passed.

From then on, it was a strange feeling whenever i was in Jacq's place - lusting for her mum while i was fucking Jacq... i became like a family fren, going over on sat whether Jacq is home or not.

One day Jacq told me, the guy he is seeing is leaving his family for her - i asked if she wants to stop the FB arrangment, she told me she wants me to continue being her frens but not FB.. i told her i am ok, if she wants me to hang ard.

after a few weeks, Jacq and me stopped fucking - she was serious about her colleague - but i still drop by occasionally at her place. One sat, Jacq was away on stayucation with him, i didnt know until i was at her place and her mum told me - she asked me if i feel jealous, i told her no and i am happy for her

Lilian asked me to help her remove the curtains in her room so she could wash them and while i was doing that standing on the stool, she touched me on my thigh and ask if i want to fucked. I stopped what i was doing, and came down - i push her onto her bed and pull her tee up and attacked her breast, she was wearing a bright red lace bra (seems like she is prepared) and i pull the left cup down and started sucking her nipples

Unlike Jacq, Lilian was quiet when i sucked her, she lift her head to look at me while i sucked her, she keeps mumbling to herself "oh gosh, what are you doing?" she had the biggest areola i have seen, so big and her nipples are gigantic huge

soon, both her bra cup was pushed down and i was sucking them both while fondling her pussy - she was wearing a denim shorts, so i unbutton it and pull it away - as expected she was wearing a bright red lace panties (matching pair) and her crotch area was soaked! like as if she pee on her panty

i caress her there, she didnt moan but keep looking at what i was doing - i wanted to go down on her but she stopped me - she turn me over and let me lay on her bed, and soon she was sucking me and making noises (not moaning) while she was sucking me

she was not as sensual as Jacq who enjoys foreplay, she moved up and sat onto me and started moving her body with my rod inside her - she was bouncing up and down on me and watch her breast bounce was making me about to cum - i told her and she ask me to come up and penetrate her missionary - i pump her so hard that she started screaming and she keep saying "oh gosh! oh Gosh!!"

i cum inside her, i dont think she came... we kissed and wipe my cum on her pussy - and washed up... i lay on her bed for awhile looking at the hald removed curtains ..

when i was leaving, Jacq came home - i think she kinda guessed what happened . . that cheeky smile she had on her face
do u write novels? this is good:
  #4749  
Old 17-07-2023, 01:39 PM
shawn26 shawn26 is offline
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Re: Anyone u sex with before that u never thought of....

yea a year ago with a cousin. I mean does it count as sibling? I hope not
  #4750  
Old 17-07-2023, 02:49 PM
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Re: Anyone u sex with before that u never thought of....



another adventure from sifu.

up your points before and cannot up again.


Quote:
Originally Posted by KimSiew769 View Post

i cum inside her, i dont think she came... we kissed and wipe my cum on her pussy - and washed up... i lay on her bed for awhile looking at the hald removed curtains ..

when i was leaving, Jacq came home - i think she kinda guessed what happened . . that cheeky smile she had on her face
  #4751  
Old 17-07-2023, 03:36 PM
timeliness timeliness is offline
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Quote:
Originally Posted by KimSiew769 View Post
Met this 32 year old OL Jacqueline from dating app - met for drinks a few times. One night send her home and she asked if i could "escort" her up as she had a previous scare of seeing a man sitting at the staircase on her level.

We went up without incident and started kissing outside her unit - her mum came back unexpectantly and saw us, she was extremely friendly and scolded her for not inviting me in. so we went in and her mum went straight to her room and came out 20 mins later changed into a oversize tee and with some clothing in her arms - saw her dump them onto the laundry basket in the kitchen and then went back her room leaving us in the living. we kissed in the sofa with the TV on.

As usual i went to the toilet before leaving, passed by the laundry basket and digged into the pile of clothes her mum just left - inside the bundle was a pair of nude bra and a green lace trimmed thong - i took it and stuffed it into my pocket (later at home i found fresh wet stains on her panties)

Anyway, a few days later i met Jacq for drinks and she suggest going to her house to watch Netflix series that we both followed. Her mum was home but welcomed us - she is extremely friendly and chat with me, in my mind i had the green lace thong on her and her stains that i licked up that day while playing with it.

Anyway, her mum left to meet her colleagues after awhile leaving me and Jacq alone in the house - we cuddle and fucked twice that day..

so it became a regular affair for me to drop by her place, her mum will sometimes cook for us, but since the first night, i dont find her mum's intimates in the laundry basket anymore.

One day, i went over her place after work - Jacq was not back yet as she is stuck at work (she drives so i didnt pick or meet her from work) - He mum was home and we chat in the living room like old friends (not as the mother of the girl i am fucking) - the conversation came to her asking me if i am aware Jacq is seeing someone, i told her i knew she was seeing her colleague for a few years.

Her mum Lilian (54 yr old) then started to tell me her worries about them, like how the man is married and how Jacq was happy seeing him - her mum asked me how i felt knowing i am seeing someone who is in such a mess.

I told her honestly that we are FB, and we have agreed to live our own lives and only meet for sex. Lilian asked if i am fucking others? i lied and say no of course .. she smiled (i think she knows i am lying) and ask me to be careful if i am fucking others (use protection etc)

So i turned my question back to her and ask is she seeing anyone, she told me she is seeing a guy for sex only (turns out that guy is the same age as me) -- i am quite surprised she is so open with me, so we chat on the topic of FB

I dont know who initiated it but we kissed and from then it was a point of no return, knowing Jacq might be back soon, i caressed her breast through her tee, i could feel her seamless t-shirt bra, she moaned when i did that.. she was very open, her hands was on my rod fondling me through my pants.. i thought maybe i could fuck her before Jacq comes back

But she suddenly pushed me away, and told me Jacq will be home soon and went into her bedroom. i sat there not knowing what i should do, go in? or just wait for Jacq... When Jacq was back 1 hr later (imagine me sitting on the sofa for the long 1 hr) Lilian came out and pretended like nothing happened.

That evening i fucked Jacq in her room, i pumped her so hard cause I wanted her to moan (so her mum could hear her) and she did (more in a rebellious way) - she was literally screaming.

After that i came out for a shower and grab a drink at the kitchen, her mum came out and saw me, she smile at me cheekily and hit my butt when she walk passed.

From then on, it was a strange feeling whenever i was in Jacq's place - lusting for her mum while i was fucking Jacq... i became like a family fren, going over on sat whether Jacq is home or not.

One day Jacq told me, the guy he is seeing is leaving his family for her - i asked if she wants to stop the FB arrangment, she told me she wants me to continue being her frens but not FB.. i told her i am ok, if she wants me to hang ard.

after a few weeks, Jacq and me stopped fucking - she was serious about her colleague - but i still drop by occasionally at her place. One sat, Jacq was away on stayucation with him, i didnt know until i was at her place and her mum told me - she asked me if i feel jealous, i told her no and i am happy for her

Lilian asked me to help her remove the curtains in her room so she could wash them and while i was doing that standing on the stool, she touched me on my thigh and ask if i want to fucked. I stopped what i was doing, and came down - i push her onto her bed and pull her tee up and attacked her breast, she was wearing a bright red lace bra (seems like she is prepared) and i pull the left cup down and started sucking her nipples

Unlike Jacq, Lilian was quiet when i sucked her, she lift her head to look at me while i sucked her, she keeps mumbling to herself "oh gosh, what are you doing?" she had the biggest areola i have seen, so big and her nipples are gigantic huge

soon, both her bra cup was pushed down and i was sucking them both while fondling her pussy - she was wearing a denim shorts, so i unbutton it and pull it away - as expected she was wearing a bright red lace panties (matching pair) and her crotch area was soaked! like as if she pee on her panty

i caress her there, she didnt moan but keep looking at what i was doing - i wanted to go down on her but she stopped me - she turn me over and let me lay on her bed, and soon she was sucking me and making noises (not moaning) while she was sucking me

she was not as sensual as Jacq who enjoys foreplay, she moved up and sat onto me and started moving her body with my rod inside her - she was bouncing up and down on me and watch her breast bounce was making me about to cum - i told her and she ask me to come up and penetrate her missionary - i pump her so hard that she started screaming and she keep saying "oh gosh! oh Gosh!!"

i cum inside her, i dont think she came... we kissed and wipe my cum on her pussy - and washed up... i lay on her bed for awhile looking at the hald removed curtains ..

when i was leaving, Jacq came home - i think she kinda guessed what happened . . that cheeky smile she had on her face


Hahaha quite literally the mother fucker. Any more instances with her mother after that?
  #4752  
Old 18-07-2023, 01:41 PM
rotaryshooter rotaryshooter is offline
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Re: Anyone u sex with before that u never thought of....

i wish TCJ and LP will contribute to this thread.

Quite nice to read about their conquest.
  #4753  
Old 18-07-2023, 01:43 PM
JackyPhang JackyPhang is offline
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Re: Anyone u sex with before that u never thought of....

Always with the girls know at clubs
  #4754  
Old 18-07-2023, 11:16 PM
Seven7up Seven7up is offline
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Re: Anyone u sex with before that u never thought of....

Ex-colleague. Single mom.
When I was still with company, we would have short casual chats if our paths cross in office. Good chemistry but nothing very special.

After I left company, dunno how come we started texting each other and had good vibe. She always tell me she go party go drinking.

Then one day she jio me go drinking so ok lor. Picked her up and we went to a pub area to drink. She wanted whiskey so ordered a bottle with mixer. I told her I was driving so she better drink more. She said ok no problem!

End of the night of coz she got damn high. I helped her to the car and went to the driver side. I turned to check if she ok then saw she totally removed her clothes!
She keep asking me to fk her so of coz I must help a lady right? Super wet and I shoot inside her then sent her home. First and last time as I blocked and delete
  #4755  
Old 19-07-2023, 03:27 PM
johnkenny3 johnkenny3 is offline
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Re: Anyone u sex with before that u never thought of....

Quote:
Originally Posted by Seven7up View Post
Ex-colleague. Single mom.
When I was still with company, we would have short casual chats if our paths cross in office. Good chemistry but nothing very special.

After I left company, dunno how come we started texting each other and had good vibe. She always tell me she go party go drinking.

Then one day she jio me go drinking so ok lor. Picked her up and we went to a pub area to drink. She wanted whiskey so ordered a bottle with mixer. I told her I was driving so she better drink more. She said ok no problem!

End of the night of coz she got damn high. I helped her to the car and went to the driver side. I turned to check if she ok then saw she totally removed her clothes!
She keep asking me to fk her so of coz I must help a lady right? Super wet and I shoot inside her then sent her home. First and last time as I blocked and delete
Shoot inside then you blocked and delete her? Shit
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