Singaporeans tell us about their ultimate sex fails
Have a chuckle or cringe at these true stories – your worst bedroom nightmares come true
by Melissa Chan /
March 17, 2020
Like it or not, mistakes or hiccups happen in life in moments you least want it to – yes, we are talking about moments like during sex.
Here’s a common one: Has anyone had someone walk in on you while things are heating up in the bedroom? Was it your mother, father or young sibling? Here are some of the most embarrassing sex moments, revealed.
While I appreciated that she was sexually adventurous, I didn’t like it when she brought her vibrator out one night. She didn’t even discuss it with me beforehand; she just whipped it out in the middle of foreplay and asked me if we could use it on each other. ‘No way!’ I yelled out, as I recoiled from her sex toy. The vibrator was ugly, for one – it was super-long, extra-thick, purple, and covered in gross veins and protrusions – and second, I wasn’t interested in ‘competing’ with it.” – Keith*, 36, engineer
“I was performing oral sex on my girlfriend. Everything was going well until she started getting more aroused. Her body began writhing and her hips started moving up and down really fast. All this was exciting for me to witness, but then her legs started moving in all different directions too, and the next thing I knew, her right heel hit me right up against my left cheek.
It felt like a punch and I swear I heard my jaw break. My girlfriend was apologetic but, ever the hero, I pretended that it was no big deal.” – Patrick*, 38, sales manager
“It was rare that I allowed boyfriends to sleep over, but I made a special exception for the new guy I was seeing – he’d had a falling out with one of his housemates and needed somewhere to stay for a few days.
While we were having sex one Saturday evening, my 23-year-old brother, who spends weekends with me, accidentally walked in on us. I was mortified! I let out a high-pitched scream and scrambled to cover my exposed body. My poor brother was just as embarrassed. I don’t know how much he saw because we avoided each other for a while after that.” – Angela*, 33, event planner
“My new boyfriend and I were getting hot and heavy on his couch. His hands were all over me and I squirmed when his fingers began touching my most intimate parts. As he felt his way around, I noticed something unusual – I was super-wet down there and the ‘flow’ felt never-ending. Surely I wasn’t that aroused? About a minute later it hit me – I’d just gotten my period!
Unfortunately it was too late and my guy’s entire hand was covered in blood. I couldn’t let him continue so I suggested we shower together. As we got up to move to the bathroom, I looked back and saw that I’d left a huge bloodstain on the couch. I was beyond embarrassed!” – Dominique*, 30, sales manager
“My ex-girlfriend liked it a little rough in the bedroom. One night she was on top of me when her hips started moving faster and faster. I didn’t mind at all, except that, with every hard and furious movement, my body inched closer towards the headboard. It was like her thighs, which were tightly squeezed around my sides, were slowly pushing my body upwards along the bed.
Before I knew it, my head was hitting hard against the headboard and I had to move her off of so that I could massage the pain in my head away. Later we tried to resume having sex but the mood had been lost. Worse, the throbbing in my head lasted all day.” – David*, 37, project manager
“I suffer from anxiety attacks. Sometimes they get so bad that I start hyperventilating, and in extreme cases, I actually hold my breath for a while. One night I was performing oral sex on a guy when, for some unknown reason, I started to panic. My breathing became erratic, I struggled to breathe through my nose, and to make matters worse I began choking on his penis and wanted to throw up.
Thinking that I’d lose consciousness from the lack of oxygen, I quickly excused myself to go to the bathroom. I had to get a grip! I did a few breathing exercises to calm myself down and drank some water to get rid of the nausea. A few minutes later I felt a lot better, but when I went back to bed, my guy was fast asleep. Talk about a mood killer!” – Jasmine*, 37, communications director
“My girlfriend and I had just finished having amazing sex. I was still inside her when I noticed that something about the condom felt strange. Worried, I pulled my penis out and saw that the condom was torn around the tip. Both my girlfriend and I turned pale as thoughts of an unwanted pregnancy entered our minds. We weren’t ready to become parents! The next few weeks were torture as we waited to find out if she was pregnant.
Thankfully, she wasn’t. We have no idea how the condom broke; my girlfriend has long fingernails so it could be that she accidentally ripped it while helping me put it on.” – Charles*, 33, chef
“I have a great head of hair and do my best to keep it looking good. Other than my barber, I don’t like anyone touching my hair, so imagine my horror when this woman I was having sex with nearly ripped a handful of it out of my scalp.
She was feeling extra-passionate, I guess. She dug her nails into my skin, which I didn’t mind, but as she started to climax she grabbed a fistful of my hair and began tugging on it. I didn’t stop her because I didn’t want to distract her, but then she pulled even harder and I actually felt pain. For a couple of days after, that part of my scalp hurt a little, as if it were bruised, but I was more worried that I might have lost some hair.” – Andrew*, 35, lawyer