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

[Summerhillt]

Originally Posted by yang punk

It must be getting frustrated enough to screw this junior undergrad that I was dating at the time. Later when I wanted to break up she used emotional blackmail to tie me down. 39 years of loveless marriage was the price I had to pay and still paying!

But I got my revenge...found my true love and fb at age 40 (she was 20 then), and she stayed single and loyal to me all these years.

Who says live is unfair?

Bro you married the junior undergrad? fwah how old are you !

[leekwantew]

Originally Posted by Summerhillt

Bro you married the junior undergrad? fwah how old are you !

Probably 45+

[turningtables]

Originally Posted by yang punk

But I got my revenge...found my true love and fb at age 40 (she was 20 then), and she stayed single and loyal to me all these years.

Who says live is unfair?

hahhaa nice

[5ag1_Boar]

Originally Posted by leekwantew

Probably 45+

39 Years loveless marriage... assume marry at 25, shpuld be 65ish bah? Yang Punk not so young.

[lipe]

65+??? May be can qualify for Senior Pioneer Package liao.

Haha

[Inceptionist]

Originally Posted by fatfella

Mine is during JC time. Hot girl broke up with her bf after A levels. All of us at chalet getting drunk and waiting to party. Laying on a bed with her, talking and flirting. Started to play around with her. As she slowly let me finger her, i kenna pass out. Too drunk. Or rather cannot handle my alcohol when i was so young. She ended up fucking some other fella that night. Missed chance. She ended up on a few Mediacorp shows after that. So missed my chance of fucking a famous girl lah. haha.

For those wondering, she not on mediacorp anymore. A loving housewife to a rich DBS director. Haha.

From your description I think I know her. A netballer? Oh well she sure is hot if we are talking about the same girl.

[Inceptionist]

Widow for 10 yr but husband only died 2 yrs ago?

Originally Posted by thunderbird

I had an opportunity to fuck my neighbor, she is a widow about 10 years my senior. She had a body that men will desire. She is about 165cm, 50kg, nice curve for a woman who is 45 years old and with 4 kids.
I was invited to her home to help her with some computer problems that she encountered. I never had anything else in my mind, but merely to help. After a few postponements, I managed to find time and call to tell her that I will be going to help her. While I was fixing her PC, she told me to she had to get a shower as it was a hot afternoon.

Some 15 minutes later, she walked into her study wearing a pink see thru’ pajamas..! I can’t help but stared at her two protruding nipples and her pubic hair (presumed well trim as it was small patch and neat) thru’ her pajamas. To be honest, I have always fantasized that I fucked her in my dreams.
She sat next to me with a towel drying her shoulder length hair. I could smell the fragrance of her shampoo, and her shower gel.

I stole a couple of glances and she noticed that I was looking at her protruding nipple. I was shocked when she asked “do you see what you like…?” And she moved even closer..! Her protruding nipple actually touches my arm..!
I could felt blood oozing into my prick, and about to burst to break free from my jeans. I stopped working on her PC, and stood up, ready to “attack”. She tilted her face upwards and looked at me in the eyes, and with an inviting smile that she is “ready”..!

That’s the time the image of her husband flashes in my mind….! Her husband and I are regular golfing partner, and drinking buddy. In his last moment before death, he requested me to look after his wife and his children. My heart beat slowed down and my I started visualized that “her husband was watching within the room”

I sat down again, not knowing what to do, or should I follow “the thought of my little head and attack since I am being provoked”, or to walk away from the battle zone..!

I guessed I made the worst decision of my sex life. I stood up and without saying a word, I went for the door of the study, climb down the stairs, I did not even look back, opened the front door and walk out of her house..!
WTF have I done…! She was dying for a fix after the lost of her husband (died from lung cancer 2 years ago), and I have not fulfilled her desire..!

STUPID…!

[garlic]

Well, for me it was getting a GF's close friend pregnant while still with GF. The affair was never exposed and the sex was always good. You guys might think it was enjoyable, but it's a pain not knowing if the child is yours and she refuses to talk about it. Still meet up now and then....

[energybost]

Originally Posted by Inceptionist

Widow for 10 yr but husband only died 2 yrs ago?

The widow is 10 years older than him

[yang punk]

Some people just can't understand simple English!

[yang punk]

Originally Posted by 5ag1_Boar

39 Years loveless marriage... assume marry at 25, shpuld be 65ish bah? Yang Punk not so young.

Bingo! Small head still 'yang' but big head old liow!

[Gd2day]

One of my biggest regrets was not fxxking my ex-gf while studying in UK about 16 to 18 years ago. Met her when i was in year 2 and she was in year 1 of the same course. She was just 19 years old and i was 5.5 years her senior. Got together and over the 2 years in UK, cohabited with her in her room. Needless to say, heavy petting and fingering took place almost on a nightly basis but with me ejaculating on her smooth, white and flat stomach.....petite size, nice B+ close to C boobs. Very sweet looking.

There was one thme when she was so high from my fingering that I was inserting my little bro into her little sister....It was heavenly but she quickly said it was painful and being the nice and obedient BF, i took it out and released on her stomach again. Very regrettable....should have just taken her virginity that night but may end up impregnating her, who knows....she was my 1 true love out of all my ex-gf. Up to this day, I can still recall that moment in her room.....

[iloveu4ever]

Originally Posted by LiN88

Not sure whether was it worth "regrettable" but used to have a guy whom I dated for 2 years, knew him over irc during those days (yes, you can imagine how long ago it was lol). He's not the most good looking/caring guy I have dated before, but he's probably the only only guy who satisfied me in all my needs when it come to sex/foreplay etc. Even when im at work and felt like mast, he will aroused me with his texts (we sexting alot when either one of us are too busy to meet up/overseas) and made me mast in my office's toilet lol.

What's regrettable is ended up we broke up and not long later, he actually found someone thrice my size and dated from 2013 till now. :/

Maybe he might read this post thou. Lols.

I will be glad to take over his position, PM me if you are interested

[lookinglooking]

My friend is asking me over to her place in aussie and since there aren't any spare beds, she's asking me to sleep together on her bed. I shall learn from the mistakes of all the bros here and make my score.

[nuclearkid]

Originally Posted by lookinglooking

My friend is asking me over to her place in aussie and since there aren't any spare beds, she's asking me to sleep together on her bed. I shall learn from the mistakes of all the bros here and make my score.

Your friend chio bo? Don't end up on her bed and kenna makan-ed instead!