My Epic Sex Fails

Here are a few examples of missed opportunities from my past that still haunt me to this day. They are simply me failing to pull the trigger. The effect they had on my confidence was detrimental. The burden of the regret was massive. It all drove the inspiration to improve.

Walking home from school in year 9, I was walking with this girl from my class. We walk past her house and the topic of blowjobs comes up (she brought it up). She says “You wouldn’t let me give you head would you?” and motions for me to come inside her house/mouth.

I mumbled something about a guitar lesson and left.


A few months later I was sitting next to her at the back of the class, made a joke about running my hand up her leg to touch her pussy, she goes “Go on, do it…you’re probably too scared.” I start putting it up under her skirt and then go “Ahhh yeah you’re right, I’m too scared.”


Another time in the locker room she was teasing me about something, and then turned all sexual and said “Oh but Liam it’s only because I’m so attracted to you and always have been” with come-fuck-me eyes, and pushed her breasts into me, I mumbled something about being late for class and hurried off.


If she couldn’t give me enough hints, one time we were walking around the city in the day time with a few other school friends and she just randomly took my hand and we held hands for about 20 minutes while wandering around till I said “My hands getting sweaty” and pulled away.


In year 9 at McDonalds at night time, I see this guy from school, say hi to him, he’s with 2 girls, the 3 of them follow us and meet us at Subway, and he goes “My friend thinks your hot” and she’s like “Shhh!!” and slaps him playfully.

We go to the skate park, she yells “WE’RE PLAYING SPIN THE BOTTLE!” She was clearly trying to create a scenario to hook up with me. I keep side tracking and making jokes about the game “Ok the dare has to be something dumb like nick nocking though.” The tension fizzles out and we never play the game, mostly because of my lack of cooperation.

Then we go to McDonalds and she’s telling us how she got fingered the week before on school camp and loved it.

I see her again in the day the next Friday at McDonalds, and I made a joke about her taking off all her clothes. She goes “Go on, do it! Take my clothes off right now! I bet you don’t have the guts…” and I start taking off her blazer, and go “Ah nah you’re right…I don’t.”

Then I brag to a friend at school about how she was “So into me” and I could have her if I wanted to, and two weeks later he somehow met her and reintroduced us. “Hey Liam. This is Laura…you guys know each other right?” I was like “Oh hey!” …but she didn’t even remember me! No one remembers the hesitating fools who don’t pull the trigger.


New years eve in year 9 in the city, I randomly see this hot girl from school. She runs up, yells, jumps into my arms, wraps her legs around me. She is buzzing, flirting with me heaps, smiling, walking me off from the group,  (she isolates me!) I mumble something and diffuse all the tension we built up and walk back to the group.
Her friend asks “Hey were you and her gonna hook up?” and I’m like “Ahhh nahh dude no way were just friends…” and proceed to regret it for years to come.


I was at a party in year 10, birthday of a hot blonde girl. I was talking to her and her friend, her friend goes “You two should totally hook up…” and I was like “Ahhh nahhh ummmmmmm. Oh now you made it awkward, lets do random stuff to diffuse the tension”. I proceeded to flap my arms like a fish, she joined in with my childish game.

Later she hooked up with another much more confident dude and I was gutted. His name was Beretta, and I tried to somehow win her back by telling him that guitars were cooler than guns. “In the video clip for “I believe in a thing called love” by the Darkness, his guitar shoots lasers, so there!” I said.  He just laughed and walked off with her, leaving me standing there limply with  my lame comeback hanging in the air.


In year 10, me and a friend went camping with a group from school, and these two hot chicks were there. I read her phone and one had a message from the other like ‘wooo partying tonight with liam and Nic is gonna be FUN ;)’. I still didn’t get the hint. A few weeks later at a house party, both girls were there and they were tipsy/dreamy, looking in to my eyes, one said ‘man Liam is so hot’ and the other one goes ‘mmmmmmm’. I stood there, mumbled ‘heh…umm uhgghhhhhhh…I’m gonna go get another beer’ and walked off.


In my first year of uni, this hot chick I knew from high school was out the front of a bar as it was closing. I walked down the street with her and her friends, and in a bid to impress them by I acting the clown, I jumped in some bushes, Jackass style. She jumped in after me, landed on top of me, her face right next to mine, and she tried to kiss me. I mumbled something, pulled her off, killed all the tension.

I walked her and her friend home, sexual tension was blown but I tried to slap her ass with her friend right there, she just goes ‘DON’T slap my ass!’ and I go ‘oh sorry’, then I said ‘I have a cut on my lip. I’ll come to this bar next week when my cuts healed!’ (Trying to awkwardly verbalize the fact that I might kiss her). I saw her there next week and I was obviously friend zoned by then.


At another house party, a hot chick came up to me and said ‘you’re cute’ and tried to kiss me, I got weirded out and pulled away, pushed her off me, and walked off.
Then a few months later, I walked home from a party with her and my friend, he was distracted watching a cat on a fence and she isolated me onto a trampoline in someone’s front yard, held me down with her on top, rubbed her tits on my face, tried to kiss me…guess what I did. Nothing! As usual.


At uni I went to a dodgy, sleazy bar, and there were some screens showing bikini chicks dancing.

I was wearing a pyjama top for a bit of fun.

Me and my friend saw these dudes from the year above, and started chatting with them. One of them had a hot older sister with them, and she started talking to me.

She was 21, I was 18. At that point in my life that was a HUGE age difference, I thought it was the coolest thing ever to even be talking to her, a girl who was THREE WHOLE YEAR LEVELS ABOVE ME.

She was being very flirty and forward with me, she kept saying how much she liked my top, and was playing with the buttons and pockets.

I started talking about the bikini chicks on the screen and went on a long rant about objectification of women, and how bad it was, and how I would never do that because I respected women, and how I only had sex with girls if I felt a strong connection, and how all other guys were so creepy and were disrespectful to women by having sex with them. I was basically trying to sound like a ‘nice guy’, it was such fake bullshit.

She was not impressed by my thinly veiled attempt to get in her pants through deception and misrepresentation of my intentions. Obviously I was just saying all that stuff because I thought it was what she wanted to hear. I thought it would impress her, so I could get laid.

She said ‘um, dude it’s okay to want to fuck. Sometimes you just want sex. Like, its fine for me to want some dick. It’s totally normal, sometimes I just really want some cock…I just really need a dick’

and I was just like ‘um YEAH I guess…you’re right! Yeah…yeah, I agree with you too! It’s okay to have sex for fun!’

So suddenly I’ve gone from ‘I only have sex with girls I’m connected to’ to ‘yeah casual sex is cool!’, changing my tune to agree with her.

I started trying to be all forward with her, following her around the club, making lame conversation, it was really awkward. She kept doing stuff like ‘I’m just going to the bathroom, ill be right back!’ and then wandering off.

It was a period in my life of such bad inner game. I had no idea what I wanted and flip-flopped about what my attitudes were to sex, and what my intentions were, depending on what I thought the girl wanted to hear.

She was on the hunt for cock that night, and I could have fucked her, but I fucked it up by having a shit self-understanding, and not being honest and congruent with my desires.


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