What is the most stupid and regretable sex shit you done?

[tikogoh]

Originally Posted by whambamtksmaam

Regretted getting together with this girl i knew from some dating web.
Basically shes a total control+jealous freak.

There was once while out shopping with her i said thank you to the sales girl that served us food and her face turned black again and her logic was since she said thank you to her already i don't have to say it again, she felt that i was trying to flirt with the salesgirl..like really? my parents taught me to be polite to everyone and i get shit from her just for that.

During valentines day she purposely used my friends to provoke a reaction from me(she hates them alot cus apparently she doesn't like them one bit) i always joke around with this group of friends i've known for close to 10years and she actually threatened me that she will call her godsister to harm one of my best friend's girlfriend whom i treat as my elder sister just because she said that i was a baby after i called her old. After failing to provoke a reaction from me her face just turned black and gave me the cold shoulder the entire Vday waste my money for booking GV gold class and taking her out to dinner and so i broke up with her few days later

lucky managed to fuck her lots of times during our staycation and even doing it raw once but didn't cum in her first time i met such a crazy girl

Breaking up with her isn't stupid. You've given her lots of chances. That's a wise move.

[sammicheng1000]

Originally Posted by Summerhillt

Haha , read from page 1 to page 31 took me 2 hours..

Now here's my fair encounter to share.

Back than when was 12 .. really like this girl in my class. Recess always play ice and water i always ask her catch me.. got once caught tio me le.. i fell down and she ask you ok ma? Need me kiss you? I damn shy say no. Till today i regret
( a kiss at 12 is like getting a bbbj le .)

Back than i was 14.. was arranged to sit beside a malay girl in class.. only 2 of us side by side everyday.. my class only had 5 boys.. the rest all girls. Walao i tell you this malay girl step shy than everyday i talk dirty with her. Than 1 day she suddenly beh tahan and ask me sternly. '' How about i give you a blowjob right now in the toilet? ''

nah beh cb.. i scared like siao and say no.. zzzz until today i don't know why.

Sec 4 liao.. had a chinese gf , shes the most chio in my class. Dated with her. Lost my virgin to her , than she had this best friend who has the biggest boobs ever.. my gf say her best fren is lesbian like her than she suggested we 3P. I felt disgusted and said no.
Now given the chance i will say '' YES YES YES '' Broke up with her.. now i see both of them looking gorgeous.

18 years.. kept going out with few chij girls together with my bro. we aim hoseh liao this 2 chij girls.. always take time out go meet them. My friend jitao ask them... '' want go hotel!?! you all dare anot?!? '' They say '' ON LA NOT SAY NEVER B4. '' I see they just sec 4 sec 5 i scared they paotoh.. i take cab home.. knn my fren had the best gangbang ever.. 2 chij girls sucking his cockhead in uniform.. both tounge on his cock... still pussy swapping fuck.. he cum in the girl than let it drip into the other girl ass and than he fuck the ass.. i saw the video and until today '' tui my xim gua tao ''
* always my dream to fuck a chij girl. '' My fren just say '' who ask you hum ji? orbi quek.. ''

Was playing truth or dare at chalet.. 3 girls 2 guys.. 1 of the girl kena dare '' we dare you lose your virgin to Summerhillt. ''
She nod her head.. I see so many people i say siao ah u all !?!? Now she on fb is a partying slut..

Went to fuck my best fren gf after they brokeup.. one of my fren saw my photos while '' playing '' my iphone games. Than the story spread like siao..

But of the most funny shit and stupid thing was.. when i 16... My gf that day and me released from school early.. she say dun go her house.. later the father coming back early , i say nvm la we fast fast.. Went to her house and fuck.. she said she got menses.. i say never mind la.. we do on the floor.. wow was good.. but blood flow like siao.. the whole floor all blood.. didnt care much after deed done and wash myself first.

NBCB. As i walked into her room i can hear her house door opening.. her house is those 2 storey hdb mansion 2 floor de. KNN I PEEP MY HEAD OUT IS THE FATHER OPENING THE DOOR. I SWEAR I NEVER FELT SO SCARED BEFORE IN MY LIFE.. My balls really went to my throat. ( i was still naked coming out from toilet. )

I suited back into my school uniform in the fastest speed ever.. now u ask me do that again i really duno how. I jitao take my whole school file pour all my assignment on the patch of blood and just slam and scoop up and throw in my bag than faster grab a wet cloth and wipe dry.. worst still i am not allowed in her house de.. cb i go hide in the cupboard with a schoolbag full of menses.

i pray to god so hard the father wont know i am in the house as my gf say he come back take some file and go le.. knn nbcb he open the door i hear him shout '' WHOM HAVE YOU LET IN MY HOUSE?!?! '' CB i in the cupboard thinking wa cb this uncle why so smart know i on top 2nd floor hiding..


knn... my school shoe never keep in cupboard.. my gf always ask me put inside cause scared got sudden spotcheck.. that day i lazy put inside.. knn father see size 10 sch shoe shout like siao..

i think.. wa cb better come out of the cupboard la if not tio spot inside lagi worse..

came down and met the father and kena fuck liao siao.. faster say sorry sorry uncle i come here help fix laptop for her.. and ran out of the house liao..

knn.. tio kan and school bag have to throw .. next day kena fuck by teacher asking where all the assignment have gone.. than my gf wink at me

Reading your story Jin song but the whole time I'm thinking that I rather be friend with the devil than be your friend.

[alec]

Wah heng ah, least u enjoyed while it last

Originally Posted by whambamtksmaam

Regretted getting together with this girl i knew from some dating web.
Basically shes a total control+jealous freak.

There was once while out shopping with her i said thank you to the sales girl that served us food and her face turned black again and her logic was since she said thank you to her already i don't have to say it again, she felt that i was trying to flirt with the salesgirl..like really? my parents taught me to be polite to everyone and i get shit from her just for that.

During valentines day she purposely used my friends to provoke a reaction from me(she hates them alot cus apparently she doesn't like them one bit) i always joke around with this group of friends i've known for close to 10years and she actually threatened me that she will call her godsister to harm one of my best friend's girlfriend whom i treat as my elder sister just because she said that i was a baby after i called her old. After failing to provoke a reaction from me her face just turned black and gave me the cold shoulder the entire Vday waste my money for booking GV gold class and taking her out to dinner and so i broke up with her few days later

lucky managed to fuck her lots of times during our staycation and even doing it raw once but didn't cum in her first time i met such a crazy girl

[stoked]

Mine isn't stupid but certainly regrettable. In my late 20s and based in a neighbouring country at the time, I had a fling with an employee of my company's client. We were both adventurous and had some hot and kinky sex. One year after I left and was posted to another country, I received an email from her saying she had met someone and going to get married soon. She said I know the guy also as we are all in the same industry. To my great surprise/shock, I know not only know him, I consider him a good friend and have deep respect. He had helped me a lot when I initially moved there. Through their conversations, they realised they have a mutual friend that's me.

I regretted the fling but the sense of regret really set in on their wedding day which I flew over to attend. Seeing them happy together, laughing, smiling, kissing, etc...I regretted having had that fling and all the sexy/kinky stuff we did.

[jnj29]

Met this girl during my poly days. Didn't get to talk to her until weeks before graduation. But don't know how we started to text each other everyday and get to know she had a boyfriend but not in a good term. We went out for a few dates behind her boyfriend but didn't do anything because we are just friend/classmate. Until one day after our date, we went back to our home started to text kinky like she wanna fuck me etc and following by pictures that shocked me that she sent me in the bathroom, my little brother see liao straight fap to that. Days later that she told me her parent overseas asked me go over to accompany her, in the end i rejected her because i want to stay at home play game. Fuck man wasted! Now she ignore, unfriend me etc already.

[handsomeburger]

During my poly days, made a mistake of having rough sex with my ex gf. Even though she wears the tudung, we were kinda sexually active. Any bros here who have or had a tudung wearing girl would know that those girls are insane in bed. Anyway, we were in her room and things got a bit steamy, so me being the very horny bf, somewhat forced myself on her. Ripped her clothes apart and pinned her down almost the entire time. Basically, i gave in to my animalistic nature and fucked her brains out. With all the moans and stuff, i thought that she was enjoying it but after the deed is done, she was crying frantically. She felt that she was raped. I was really scared that she would tell the police on me. Had to apologize and console her for almost 6 hours straight. One of the most scariest experience in my life.

[Neoguri]

I posted the below in another thread, but think it is also applicable here.

I had a chance when I was 22 or 23.
Was at another colleague's apartment after a company drinking session and a few of us stayed overnight.
I knew she like me and she found an opportunity where we are the only 2 left and in the guest room. I woke up in the middle of the night to find her staring at me.
She kissed and hug me and I went along with her, but decided not at the last moment when she asked me to enter her.
I was too idealistic at that time of my life and wanted my first time to be with my wife, so i didn't do it with her.
Thinking back, I was pretty stupid!

Now, I am divorced and trying to catch up lost time and up as many girls as possible.

[Wisemanstand]

Couple of years back, I was in China and there was a girl who occasionally came to visit me which gifts, and then, always sit on my bed or close to me (I stay in Hotel). Then, every time she did that, I am kind of stupid or what, tried to avoid her coz of shy, after that, she just left my room.

At one time, she came with her friend and wish to give me a massage, she on the yellow light, but I switch on the white light.... after that both of them left without saying anything. I called her and she asked me whether I dont like her.

Think of it, should try on her. She has nice figures and should be enjoyable.

Early this month, met her again and invited her to my room, but she scolded me said she is not easy going person, and is on period.

Will see any chances to meet her again.....

[PAssionCard]

Originally Posted by Wisemanstand

Couple of years back, I was in China and there was a girl who occasionally came to visit me which gifts, and then, always sit on my bed or close to me (I stay in Hotel). Then, every time she did that, I am kind of stupid or what, tried to avoid her coz of shy, after that, she just left my room.

At one time, she came with her friend and wish to give me a massage, she on the yellow light, but I switch on the white light.... after that both of them left without saying anything. I called her and she asked me whether I dont like her.

Think of it, should try on her. She has nice figures and should be enjoyable.

Early this month, met her again and invited her to my room, but she scolded me said she is not easy going person, and is on period.

Will see any chances to meet her again.....

Thanks for sharing.

[OngTummy]

Originally Posted by Wisemanstand

Couple of years back, I was in China and there was a girl who occasionally came to visit me which gifts, and then, always sit on my bed or close to me (I stay in Hotel). Then, every time she did that, I am kind of stupid or what, tried to avoid her coz of shy, after that, she just left my room.

At one time, she came with her friend and wish to give me a massage, she on the yellow light, but I switch on the white light.... after that both of them left without saying anything. I called her and she asked me whether I dont like her.

Think of it, should try on her. She has nice figures and should be enjoyable.

Early this month, met her again and invited her to my room, but she scolded me said she is not easy going person, and is on period.

Will see any chances to meet her again.....

Thank you for sharing.

[BruceBuck]

Originally Posted by Neoguri

I posted the below in another thread, but think it is also applicable here.

I had a chance when I was 22 or 23.
Was at another colleague's apartment after a company drinking session and a few of us stayed overnight.
I knew she like me and she found an opportunity where we are the only 2 left and in the guest room. I woke up in the middle of the night to find her staring at me.
She kissed and hug me and I went along with her, but decided not at the last moment when she asked me to enter her.
I was too idealistic at that time of my life and wanted my first time to be with my wife, so i didn't do it with her.
Thinking back, I was pretty stupid!

Now, I am divorced and trying to catch up lost time and up as many girls as possible.

A bit wasted

[joncheong]

i think the most stupid and regrettable sex shit that can happen to a guy in singapore is picking up a ONS and next morning she woke up, find herself naked crying rape....that scene can make you go soft even if she is well endowed and naked in front of you, can even break cold sweat...

heard from a buddy of mine before of such similar incident...lucky never happen to me..

[stoked]

Reminded me of another incident. Back many years, I had a gf S whom I loved dearly. We broke up when she went overseas to study. We still meet and will have sex whenever she comes back for holidays wheher she has bf or not in that country. Sex between us continued for many years. She came back, I went away but we continued on. We clearly have deep feelings for each other but never had the chance to live in the same city to have a proper relationship. Eventually, she got knocked up, married and moved to another country but we continued fucking whenever we have a chance to meet.

At some stage, I became fb with her best friend (good story actually, maybe I should write about it). She is as hot as S but way hornier, not afraid to say she wants to fuck and how she wants to be fucked. She is bi and needless to say, I had messy and memorable 3P sessions. She taught me many things about making love.

S got divorced, came back to sg with her child and we finally start a proper relationship albeit with her child in tow, whom I not only accepted but treated as my own. It was not to last however as S ex-colleague turned out to be one of those I was involved in 3P before. She told S and if it was not with her best friend it would not be an issue. The issue was it was with her best friend and when S confronted her, she was devastated. They stopped talking and S walked out of my life.

[KimSiew769]

To me, definitely sex with my gf's aunt (gf's mum sister). she is 55 but looks younger than her age. divorced with 2 daughter (23 & 25). always wearing strong perfume, causing me to get sex-cited

one day, after family dinner gathering, my gf took her parents car home so i can go straight home . i offered to give my gf aunt a lift since she stays near my place. on the way , it was casual chit-chat so nothing much.

When we reached her place, i offered to help her bring her things (2 big shopping bags) up for her but in the lift realized one bag was full of lingerie cause the shopping bag handle gave way and i drop it . i tried to pick up and realized inside the bag is a few sexy lingerie and 2 lacy bras . it was kind of embarrassing and she keep apologizing and explain that she bought it online and got it send to her office blah blah

When we reach her unit, i pretend that i need to use the toilet and she signal me to her room toilet as she syas her common bathroom very messy. i saw a pair of pink bra and g-strings hanging inside her bathroom, lift it to smell. i didn expect i got so hard smelling it.

to be honest i cant really recall what happened after that when i came out, cause i remembered when i came out she was standing near her bed and she rush to kiss me. i didnt even hestiate and kiss her back. until today i still dont know what causes her to do that.

We kissed and i moved my hands to her breast and in less than 20 seconds, we were naked on her bed.

i was initially worried that her daughters might come back and they are close to my gf. but then she assured me that they are both staying over at their bf place.

her blowjob was amazing and her moan was loud and sexy... when i move my head towards her pussy to lick her, she was shocked and mentioned she has never done it before. that night i think she squirted thrice and her bed was so wet, i have to help her change her bed sheet before i left.

i went raw and shoot inside her as she assured me she is safe cause had ops after giving birth to the second daughter

till today, i still cant imagine it happened and why she initiated the kiss. now i still do meet her during family gatherings, and she has acted like it didn't happen at all nor did we contact each other or had a second fling.

it was strange , maybe stupid but not regrettable (maybe unforgettable)

[hhlover]

For me.. it happen 10yrs ago.. one nite after clubbing wit my then gf.. go back to my house.. once in my room, naked wild sex.. maybe due to abit high... we did it raw.. n most importantly.. we both come together shooting all my load deep into her.. not 1 times, not 2 times but 3 times of sex the whole nite..
Now i have a 9yrs old kids.. n have lost my 10yrs freedom.. n still counting... hahaha