Memoirs of the Eternal Bachelor #01

The following is a true story except names have been changed or given nicknames for anonymity.

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PROLOGUE

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"Brenda..." I nervously mumbled out as I walked behind her. She stopped walking and spun around.

"Uhh, could I grab your number just in case I need help for study or something?"

She was startled. "Oh, yeah, sure."

She started to reach for her pocket to grab her phone, then stopped herself. "Oh, I should be able to remember my number by now."

She told me her number, I entered it in my phone, and I went back home in the happiest mood in my life.

I was ecstatic, I had so much happy energy inside me that as soon as I got home I pumped my fists in the air and screamed "YES!". That was the first number I ever got from a girl.

But of course it didn't go anywhere. She ended up deleting my number.

I've always been terrible with women. I never went to the senior proms (there were two of them), was bullied for being terrible with women, and had no friends in highschool. The first girl I ever dated abandoned me after a few hours and twenty minutes later FUCKED A RANDOM STRANGER IN AN ALLEYWAY because I was so boring. At the start of my first year at university I became determined to change this, and eventually I became THE ETERNAL BACHELOR.

I started by walking around the campus and my city, spending hours trying to muster the courage to talk to girls. When I did start a conversation with one of them, my nervousness made everything awkward and I always left within the first minute because I couldn't handle the pressure. I was equally as nervous when going out at night to bars/nightclubs. I was an immensely shy, acne-ridden skinny guy. To make things worse, I got diagnosed with Laryngopharyngeal Reflux which means I couldn't drink even a drop of alcohol to ease my nerves.

I saw an advert for a local seminar on how to pickup women, so of course I attended. Through this event I met some wingmen, and some eventually became good friends and I was no longer lonely all the time.

Gradually meeting women and having a nice conversation with them became easier, but I was still making mistakes. One time a girl asked me to add her on Facebook and I refused her like an idiot. Another time, a really hot girl called me good looking and blatantly asked me what my favourite sex position was after 10 minutes into a conversation, to which I froze and told her to ask a less awkward question (to this day I still don't forgive myself for this). One day when I was walking down the street there was a group of european girls who waved at me and giggled but I didn't do anything.

At 20 years old, at the end of my second year at university, I took a break from talking to girls for a few weeks. This is the story of my first night back.

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Chapter 1: First Blood

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I hadn't been out for a few weeks so my skills were rusty. I went to my favourite bar alone and walked around like an idiot. I was sober as always, and I couldn't start any conversations. I spotted some guys I knew, Bradford and his friend 'The Engineer'. They were also trying to get laid, so we teamed up and marched over to another bar.

Gradually I started to talk to some girls and began to loosen up and 'get in the zone'. We bounce between different bars until finally we end up in this really sleazy place, there's a fight here every night because various gang members like to here.

I get a drink (a glass of water) and find my wingmen talking to a big group of tourists. I tapped the closest girl on the shoulder and introduced myself. She looks at me like no girl has looked at me before. Big, wide, sparkling eyes, as if she is anticipating my every word with excitement. She is short with a sexy Brazilian accent which is like music to my ears. My masculine instincts kick in and I just kiss her straight away. I didn't even bother talking to her friends. Her english is poor but that makes her even sexier. She is average looking, a bit chubby, but any guy would fuck her if they had the chance.

She complains that she's cold, I tell her I'll keep her warm, so I hug and hold her. She's really small so I was like a giant to her.

We hadn't even been talking for a minute yet but I whispered in her ear "Where are you staying?"

She knows what's up and tells me she's staying with the other tourists. I consider taking her to an alleyway to fuck, I was getting hard just holding onto her. I tell her to come outside with me, she goes to the toilet first.

Outside, I take to to an alleyway and she chat as she's in my arms. She complains that she's cold, so I hold her tight against my body to keep her warm. I tell her she's sexy. She calls me a bad boy. Says I probably do this to girls all the time. I held her with my back to a wall and made out with her passionately. I slipped my hand down her pants and squeezed her bare ass, and did the same for her breasts. To feel the nipple of a woman's breasts in my hands was ecstasy! I reached back down and clutched a handful of her big ass again. I wanted to fuck her so bad. I had a gigantic erection and was starting to leak pre-cum.

She wants my number so we can go out another night. Fuck that, I keep trying to pull her into the alleyway but she starts getting seriously annoyed and I'm worried that I'm about to lose her entirely.

Her friend call her on her phone, I don't speak portuguese so I don't know what's going on. Next thing I know we've returned to the sleazy bar, her friend scans me for psycho axe-murderer vibes and gives me the all clear.

My sexy Brazilian says, "We can go now", so we get a taxi home.

I live with my parents, but luckily the house was empty on this night. In the taxi I relax with my arm around her shoulders. It dawns on me that I'm going to get laid. We get to my place and I give her a tour of my house. We both use the bathroom, I get us some water and we just chat in the kitchen for a few minutes.

I grab her with arm and with the other I take her empty glass of water and putting it aside on the table. I lead her to the bedroom and we start making out on the bed. I turn off the lights. Then a disaster happens.

She realises she lost her passport and freaks the fuck out and starts crying. I'm pretty worried this could ruin everything. I comfort her and hold her and try to downplay the whole thing. Tell her it'll be alright, that we'll find it in the morning, to relax, etc. She calms down, and we go back to kissing on the bed with the lights out. I take off my jacket and my shirt first, then start to slip off her clothing as well. I realise I don't know how to take off a bra and so I make an excuse about it being too dark for me to see it. She does it herself. Although it's dark, I am amazed to see my first pair of breasts with dark brown nipples. I squeezed them and put my hands all over them as we make out. This girl is amazing, her body, her accent, her perfume, the warmth of her skin against him. I'm infatuated. Eventually after twenty minutes of kissing she takes off her jeans and I've got her down to a black thong. It's fucking cold so we get under the covers and cuddle up to each other, more kissing. She's really shy, so I grab her hand and slowly put it on my dick. Lots of nervous giggling from her. She grips my penis and starts to tug at it as we kiss.

She says she's shy and has never had a one night stand before. Welcome to the club, I'm a fucking sober virgin sociopath but I keep my mouth shut. She continues giving me a handjob as we kiss. I reach down, pull down her thong and start fingering her. It's so wet and warm.

I have no idea how to finger a girl and after a few seconds blatantly blurt out "I have no idea what I'm doing."

She laughs and says "yeah you're pretty bad."

She takes the initiative and get on top of me. I put on a condom and she grabs my dick and put it in her pussy. It's a weird, warm feeling and it's nothing like I imagined it to be like. Not better or worse than I thought, just different. She starts rocking her body against mine, and I rest my two hands on her naked ass.

She had a huge curvy ass. Not curvy in the fat way either, just wide hips and a big ass. I stop her after a few minutes to fuck her missionary. There are so many positions from porn videos that I want to try. I tried to throat fuck her but she was resistant, so I'ld just swap to something else then try to throat fuck her again later and eventually she gave in. She lay flat on her back and I kneeled over her, I put my dick in her mouth, as far as it could go. Within a few hours I had gone from being a virgin to having a sexy Brazilian gagging on my dick, not bad!

Three ejaculations and three condoms later, we stop for a while and just talk. We've been fucking for hours and we're both pretty tired. I get out of bed to turn off some lights and make sure the doors are locked. I come back and decide to fuck her again before we head off to sleep. This time I'm not holding anything back, I fuck her harder and better for at least an hour. She moans louder and louder. Doggystyle becomes my favourite position, I love watching her ass bounce around as I thrust deep inside her. Felt like I was in a porn movie, the bed started to squeak loudly and her moans became screams. Best part was the squeaking bed and when something fell from the bedside table because of us rocking the bed, there was a load CRASH but we hardly cared because we were fucking so hard. It felt so raw and passionate. A very nice reward for all those nights I went out, all those rejections and all those near misses.

As I fucked her I told her to say "Fuck me [MY NAME]". She complies, then I tell her to keep on saying it.

The whole thing ended very intensely with her moaning "Fuck me [MY NAME]" over and over and over, pretty hot because of the Brazilian accent. I pulled out and came into the condom.

Finished up and later I realised I had fucking blood all over me.

The Eternal Bachelor: the slayer of pussies, born and baptised in pussy blood itself. It's all over the bedsheets too.

She finds out and goes wide eyed "Oh my god!" She frantically snaps her attention to me.

I did not give a fuck at all. I held perfect frame, calmly responded "It happens, it's fine." She calmed the fuck down real quick after seeing I didn't give a fuck about it. Fell asleep with her in my arms.

Absolutely the best night of my life. You can bet I went straight back to being a nervous idiot the very next day but at least for one night I was a god. Performed much better than I expected, no problems at all. Not an embarrassing disaster, really smooth. I kind of knew what I was doing, for each stage I already have a plan in advance so it flowed very naturally despite having no actual experience of one night stands or sex. The result was highly rewarding, my first memory of sex is fucking amazing. She insisted on getting my number as I showed her to the door in the morning.