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Upstart's AA Program Log

I MADE HER PAY FOR BEING LATE.​


I finally got a date from Facebook dating. I haven’t pulled that off since 2022.

She was 34 y/o. Black, skinnier in person than online. Definitely looked her age despite the make up.

I drove over an hour to get there.
She was an hour late. I thought I got stood up, tbh. She texts me 40 minutes after our appointed time (7pm), saying something came up that got in her way.

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I understood.
But I texted back. "Tea is on you tonight. I was about to go home."

She calls up saying she'll be there soon, apologizing for running late.

She arrives.
I hug & greet her.
She apologizes.
I say, "It’s all good. What held you up?"

"Oh, I went to get my nails done before coming."

I’m thinking: YOU WHAT?!!
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You did not just make me wait for that. I thought it was a legitimate emergency.

So after getting her reason, I felt fully justified in making her pay for my tea.

I said, "Okay cool, you got us then?"

"Hm?"

"You’ll pay for us both, then. You got my tea right?"

She says, “Oh no, I don’t pay for dates, but how about this, we split it half and half.”
I said very casually, "No you pay, or I go home." And literally started walking away.
I stop to look at her.
“Up to you. I’m good either way.”

She looks around, “Well alright..sure.”
Me: "Okay, bet." :D

I was smiling the whole time, but dead serious.

The rest of the date proceeded as normal, albeit a little stilted at first. we had our tea, then went on a small walk outside. We were in the Domain in Austin, so we checked out the Apple store before going back to our cars.

This is the power of having options.​

I knew I was going out on a date the next day, and fixing to clap some cheeks afterward.
With that in mind, I could stand on business in the moment.

In fact, I thought she should be offering to pay for the tea, simply to make up for her tardiness.
I don’t know what it is about older women, but they try to treat you like you ain’t nothing just because they got a few years on you.

At the end, she said "I’ll text you when I get back."
I said: "Same. Have a good night."

She hasn’t texted.
And no matter what, I will not text first.
If she don’t, I won’t.

If I got nothing else from this date, at least my balls grew two inches today.

And I got a free drink.😉

One of the best mindsets I've seen on the forum, especially among guys who are still newer.

Mad respect
Thanks man! Really appreciate your advice!
 

I MADE HER SQUIRT...TWICE (w/ pics)​

March 1st, 2025
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Today's Selfie

I've been tired all fucking day tbh. And my arms hurt.

I didn't even bust a nut and I'm DRAINED.


We went to a ramen place last night.
Ate and talked and split the bill. That shit was like $20, her order was $30!
I was wearing my cool guy glasses, and my Naruto shirt.
She couldn't help but to take a pic.
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This isn't the pic, this is from 2022

Anyways, I already invited her back to my spot on the previous date so, she went back home to pack an overnight bag then drove nearly an hour to meet me back at my spot.

We put on Rain Man, then she got changed for some love-makin'.

I was super relaxed and she was high from smoking before coming over.

So we started super slow. No kissing or real touching yet, I simply laid on her before starting massage her back.

Then we got into it. When I got hard, I just went right to work, I knew I'd get soft again if I didn't take that opportunity, so I went in RAW.

I was pumping for a good long time before I went a little soft, so I was happy my dick was working.

Basically, my problem is that my dick is used to the vice grip of my hand, so even raw sex doesn't do much for me. In the future, I'll be masturbating with a lighter touch.

I asked her if she’s ever squirted before and she said no, that she’d probably have to drink lots of water beforehand. Otherwise, she just gets really creamy.
I said, "We’ll work on that someday."

Who knew someday would be today.
---------------------------------------------------------


I actually tried to think of my favorite porno to stay hard while fucking her, but it was actually taking me out of the moment and into my head, thinking of touching myself with my hand instead of staying present.

I got out of my head and back to the moment. I tried to relax a bit, but I still couldn’t be erect fully. No worries.

I’m glad I have this problem instead of premature ejaculation. This is more of a mental thing.
She even said I set a new record of staying hard this time.
I thought so too.

I didn’t want to go down on her again because of the taste from last time lol.
So after a lull in the action, I massaged her a little more before starting to finger her.

Now this part is key:
I simply asked her what she’d like me to do.

She asked for 3 fingers in her. I was like…"For real?! I mean all right. As long as it doesn't hurt"
My hand felt weird and kinda strained, but I went to work with it.

Then I started touching her clit at the same time. She liked that.

Then she asked me to lick it at the same time I was fingering her. She REALLY liked that.

At this point, she was moaning loudly and screaming my name.

I kept going until she said, “Right there!” And I kept up the pace.
I couldn’t lick any more so I was using my thumb to stimulate her clit.
She was pushing me back a bit. Twisting and writhing.

Then the clear stream of fluid shot out.
From where, I don’t know.
I kept going.
She had clenched her legs around my hand.
When more fluid drizzled out, she kicked me off.
“GET OFF OF ME!” she screamed (not in a bad way tho :devilish:)
I lay on my back on the floor, she lay slumped on the side of my bed, pussy leaking.
There was a puddle on my sheets.

puddle.jpg
SHeeeeeesH!

I sat back in awe. Smiling and laughing.
I had given her a screaming, squirting, orgasm.
And she was too tired to move. 10 or 20 mins passed.
I wondered, Did that really just happen?!

Listening to her and taking my ego out of it made this all possible.

I told her I wasn’t going to bust a nut. I knew once I said that, I could not go back on my word.
One of those things I’ve learned over the years.

We cuddled, I asked if she was okay with pics and recording.
She was fine with it as long as her face was covered. I said "Dope", and snapped a couple pics and vids.

I’ve ALWAYS wanted to do that.
I’ve had dreams where I get close to doing it, but I always, without fail, wake up before I get the chance.

I asked her about her fantasies.
She said she wanted to ride my face and have full control over the motion.

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I would most surely die of suffocation or break my neck. (she's a big girl)

I told her, "We can try that someday as long as you don't kill me."

I told her about some of my upskirt type fantasies.
It was dope to be open enough to tell her.

In the Morning: The Second Cumming​

I start massaging her back and we got into it again.
I enter raw and just do a few strokes, we both agree that stroking is the only thing I need to work on. It’ll just take some time.

Then I start fingering her again. This time she’s in doggy position and I’m blasting her with 2 fingers stimulating her clit with my thumb. She moans and screams an tells me when I hit the right spot.
Then BOOM.

“Get off me!” She screamed.
She came AGAIN.

No stream this time, but I think she used it all up last night.

She asked me, “How? How did you do that?”
“Do what?” I said.
“I just came again.”

I said “Wow, I couldn’t tell.”
I genuinely didn't believe it, but she was slumped over again like before.

“Are you sure you don’t want breakfast?” I asked.
“This is my breakfast.” ( referring to the massaging and the sex)

We fucked all over my bed last night and I wasted 4 condoms lol.

But I felt like a G afterward.

I sent her home, a happy camper.

Afterward, I was tired and drained the whole day, Couldn’t focus for shit. Had no energy for anything. Barely got anything done.

But it was worth it. I gained hella EXP from this. I’m currently trying to secure a second option from the apps, so I can at least have 2 in rotation.

This was a good week, all things considered. I feel like I actually grew.
From standing up to a woman and making her pay for being late to a date, to making a girl cum TWICE. I never would’ve imagined this shit happening at the beginning of this 90 day challenge back in December 1st.

90 DAY CHALLENGE RESULTS​

The goal: Get ONE single date and MAYBE get laid ONCE.
The result:
  • 4 dates with 4 separate women
  • 9 dates overall
  • Laid 3 times with one girl.
  • Learned the squirting orgasm technique
March 1st marks the end of my 90 day challenge and it all started from me shifting my thoughts from a downward death spiral to an upward positive spiral. I wonder what else I can accomplish if I keep going with this shit.

All I did was find 10 things everyday to be thankful for.

Looking back at my past 90 day challenge where I felt like an utter failure, I think my mistake back then was underestimating how much negative thoughts get in the way of success.
I didn’t have a growth mindset and I wasn’t thinking of solutions to my problems as they came up, only issues.

For these next 90 days, I want to:
  • focus on improving my dating photos
  • smash a cute/hot girl
  • improve my finances and business
  • then I'd like to incorporate more cold approach when my job lets off for break.
I think that'll be doable.

In terms of money, the best place to start is by actually looking at my bank account and savings.
Then accept where they are.

DEEP in my mind I probably think:
It’s so difficult and next to impossible to become rich from being a cartoonist. How can I possibly catch up to these young youtube and tiktok millionaires in a market that’s completely cooked?

Now, I know I can find a way.
If anyone can, it’s me.
 
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Life is pulling me in so many different directions, I can't stop moving.​

Today's Selfie:​

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Get a load of this guy.

Dating app matches come in waves. Some days or weeks are dry, then a LOT of matches all at once. Most don't pan out into dates. But I like that I can collect exp just from messaging multiple girls constantly.

Some, I hope work out, others I don't really care for, but luckily, I have a fuckbuddy to hold me down while I try to build my rotation. She's even treating me to dinner next time. On HER birthday.

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In the coming week, I'll be doing a self photoshoot, going out to different locations in the domain and downtown Austin to take dope photos for my dating profile and instagram maybe approach some girls while I'm at it. It'll be the week of SXSW so parking might be horrific.

I'm gonna get a haircut soon, then use every tip and trick I've learned to takes several great pics every day for 7 days. At the end, I'll review them all and use the best of the best for my profile and the rest for instagram, I'm really trying to optimize my online dating presence to make shit happen. Of course it'll come with a whole new set of quality problems, but we'll cross that bridge when we get to it.

I'm 188.5lbs. Nearly to my goal of 187. I should hit it by next week!

As much as I want to fuck, I don't think I can handle more than 3-4 girls in rotation while also trying to run a successful comic business.

But I promised I wouldn't lose momentum ever again so I'm just gonna figure this out.

After my photoshoot, I'll have no problem getting even cuter matches online.
I'm glad I'm getting results even now.
Most have been thickk black women, some thin, but mostly black.
Most responses are generally warm to lukewarm unless I do something in my text game to get better results.

When I think about the girls I actually want, they tend to fall into the category of asian, latina, & white. It's just facts, I can't deny it. I may be able to make up the difference with cold approach tho.

Unfortunately, I also have to create an AWESOME comic and try to make money with.

All the meditation and focus I did to attain this reality is finally bearing fruit and it's sort of exhausting.

Life is coming at me like an endless flow and I can't seem to find a moment to just sit and contemplate it like I used to. Thinking actually slows me down.

I want too much and I'm willing to do whatever it takes to get it ALL.

Not for the thing itself, but for who I'll become as a result.
 
Congrats on the results of the 90 day challenge!

The old Spider-Man hand is very effective. Get good at it, I never go down on girls just a good finger blasting but also my mouth is better used whispering dirty things in her ear.

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There a few WW/KYIL dudes who kick around Austin. @MILFandCookies Ed, Ronnie. I know Joe would know good photo spots.

Make a comic about dating as a man. (Have you seen hoemath, he makes shitty pen drawings to explain red pill stuff)
 
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SHE WAS NEARLY IN TEARS.​

"YOU'RE THE ONLY MAN WHO'S EVER MADE ME SQUIRT."

"You're like a drug to me."

"I love it when you're aggressive."

Sheeeeeit.

I'll explain in a min, but check out the fresh cut. (unbrushed)
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I had a choice between a $10 student barber and the $40 one and I went with the latter because I wanted their professional advice.
They gave me a good cut, so I took pics for future reference. They give me extra tips on how to take care of my hair, which is exactly what I was looking for.

I also did a little mini photoshoot with my Hunter X Hunter fit.
Not great lighting wise, and my tripod handle was in the way.
Not dating profile worthy, but I might enhance, crop, and post to instagram.

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I realized I'm at a crossroads in my life​

I'm caught between major career progress and an abundant dating life.
And I want BOTH.

I grew up drawing and writing constantly. Trying to improve my craft to a level where I could make good money from it. Because of that, I completely neglected my social life.

Now that I have the opportunity to embrace that side of life, I'm also getting MAJOR career changing opportunities at the same time.

I really should lock in and knock these opportunities out of the park, but I promised myself that once I got my dating life started again, I would never let that momentum go down.

Or else I'd have to start over from zero (again), learn the new dating meta (AGAIN) And that is too excruciating a process if you don't have the money to shortcut it.

But if I lock in on my comics career, I would have the money to shortcut it in a few years, I just don't want to wait that long.

It's just gonna take some better planning for now.

THE GIRL​

I made her cum so hard she was basically convulsing on the bed.

RULE 14 of the 16 Commandments of Poon​


"14. Fuck her good"

"Fuck her like it’s your last fuck. And hers. Fuck her so good, so hard, so wantonly, so profligately that she is left a quivering, sparking mass of shaking flesh and sex fluids. Drain her of everything, then drain her some more. Kiss her all over, make love to her all night, and hold her close in the morning. Own her body, own her gratitude, own her love. If you don’t know how, learn to give her squirting orgasms."

That's basically what happened last night.

My sexual confidence had gone WAY up dealing with this girl. I don't fear ED anymore, and I don't even feel like I need Cialis for help, but I am willing to try it someday.

Now I truly see the difference between sex and masturbation, sex is pleasing your genitals by yourself. Only your hand, dick and eyes or thoughts are involved.

Sex is a full body workout.
It requires everything you've got, and more.
I feel so drained the day after a good fuck. That's how tiring it is rn.

I want to work towards dealing with more women who are more my type.

The first time I fingered her to an orgasm she flew off the bed, and was down on her knees ass up.
I spanked it and didn't even give her time to rest. I started to lick around her vulva and clit.

Then we 69 and I finger blast her until she cums again, that's when she convulsed. She seem like she was gonna cry until it all came out.

She's so tired and satisfied by this point, she says "do whatever you want". I jerk off and finish on her stomach. Making sure to wipe her off with paper towels.

(No getting preggers with my sperm, betch.)

I tried to leave in the morning. She would not let go. We fuck again. I set a new stroke record. I make her cum (with my fingers) again.
I try to leave to the point where she's grinding her ass on my dick and I grab her by the tit and her arm and force her with my strength into the bathroom so she can wash up.
She can't resist.
She gasps at the audacity.
She's loves it.

She tells me, "I love it when you're aggressive."

She gives me big hunk of her birthday cake to take home. It was a delicious carrot cake a coworker made her.
She also bought me dinner on her own birthday.
It was thai food. Fucking delicious, from a place called "Madam Mam's".
I've never had thai before.

We also watched Tropic Thunder, her favorite comedy movie which I'd never seen. It was HILARIOUS. I'd only seen clips before, but this was funnier than I expected.

UNFORTUNATELY...


I know this won't last.

I don't want it to last.

But I'm thankful to her for getting me back into the game and I show it by being completely devoted to her pleasure when we meet up.
I actually started with a full body massage this time. Learned on youtube.
My emotions are almost completely shut off to her, yet I fuck her better and better each time.
Weird dichotomy of emotion there.

PHOTOS​

This week is THE time to lock in and get these photos right. I got my haircut & shaved my chest.

I'll be taking a shirtless photo, and several more photos in dope spots around Austin. I've even got my clothes planned out and ready to iron. I just have a few more preparations to make and tips to read before I go out there.

I'll take HUNDREDS of photos, then I'll choose the best of the best, ai enhance them and share them with y'all on here for critique. Then I'll optimize my profiles for the best results and go from there.

So far, I only plan to keep the dog photo and the white shirt photo (my profile pic)

I need:
  • a good portrait
  • a social proof photo with a friend.
  • a shirtless physique photo
  • a photo in a dope spot in austin
The rest are optional, which I'll upload to instagram.
I'll probably take a new motorcyle photo with different fit as well.

Congrats on the results of the 90 day challenge!
Thanks man, Imma keep it going!
 
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