Upstart's Progress Log - She Bought Me THIS for F*cking Her WELL...

[Squilliam]

Uhh, restaurant (I didn't say dishwasher) . But only for a little while longer, soon I'll have my art career off and running, haha.

Oh, does your industry make a lot of money?
Not really, unless you're really good (like me) I had to resist the urge to pull out my instagram to prove myself.

I keep getting into this dynamic with older ladies it's like they have all the expectations I can't meet because I'm fucking broke.

I just have this discomfort around being so poor, I'm literally below the poverty line. I don't even know how I'm surviving off of negative money at the moment. Payment plans, and recurring bills I guess. Always teetering on the edge of financial ruin, again.

When she mentioned that for next date we should go on a glass bottom boat ride, I had a mini panic attack.
I can barely afford to EAT right now, betch!

EE women are generally pretty strong framed. My ex was EE (well, 2nd gen tho) and honestly it was a lot to handle. Those women typically have a very rigid standard of masculinity, they want you to be dominant, to provide, to lead, etc.

Older women are generally less gamey but in other ways they can be more demanding. Older women are more likely to want something serious and settle down.

One thing I learned from my ex is, in EE culture, there's no such thing as "seeing each other". You're either dating, or you're not. Hence why I think you might struggle to have casual sex with a woman like this.

I would proceed with caution. She might not put out next time or the time after that. And in my opinion you shouldn't be ramping up the date quality if she doesn't.

 

[Upstart]

Thanks Bman!

What was your game plan with this date?

Basically, this was just a "get to know her" date. I try to follow the Caleb Jones model where it's second date sex, I don't want to pull on the first date (unless it's on the table) because I want to be able to retain the girl for longer. And I don't want to catch a surprise STD.

Why are you doing dates all the way up north? Did you choose the place or did she?

I chose a spot closer to her to make it more convenient for her in this particular case.
I keep matching with far away girls, but that's how I set up my apps. I usually run out of options near me.

I don't feel like I have the optionality yet to confidently start making girls come up to me, but I know my FWB would make the hr drive from her spot, just because I smash her like no other, lol.

No, cold approach in Austin.

I always though there was an abundance out there. Just depends on the time of day in my case.

And yeah, the broke thing is definitely mostly in my head, but still!

 

[Upstart]

EE women are generally pretty strong framed. My ex was EE (well, 2nd gen tho) and honestly it was a lot to handle. Those women typically have a very rigid standard of masculinity, they want you to be dominant, to provide, to lead, etc.

Older women are generally less gamey but in other ways they can be more demanding. Older women are more likely to want something serious and settle down.

One thing I learned from my ex is, in EE culture, there's no such thing as "seeing each other". You're either dating, or you're not. Hence why I think you might struggle to have casual sex with a woman like this.

I would proceed with caution. She might not put out next time or the time after that. And in my opinion you shouldn't be ramping up the date quality if she doesn't.

Thanks Squilliam!

I'm trying Andy's honesty stuff and just try asking her if she down. Here was my last text to her this morning:
Usually she'll get back to me that night or the next. We'll see wassup soon enough!

 

[Upstart]

4/24/25
JUST WENT ON A DATE WITH A CHILDHOOD FRIEND
What is this, an anime?!

DATE FIT:

Made sure to do extra pushups just in case.

The date was smooth sailing.
She had grown and I had grown, and I said "You sound like an adult now!" We laughed and mentioned Rugrats all grown up.

We had ice cream and we basically talked about our middle school days and what we'd been up to since. She'd been traveling the world A LOT. She keeps very busy and saved up a lot to be able to travel.

Toward the end, when we were sitting, just looking at the lake, I asked her about her dating goals, and she told me, since she was traveling a lot she wasn't trying to stay in one place for too long. I told her I wasn't looking for anything serious, but I'm not the one night stand type. I said I like to get to know a person first before we get physical.

We converse a little more before I say, "Would you be open to a kiss?"
She laughed and said, "Yes, I think I would."

BUT!
When I started to go for it, she said she wasn't ready for anything sexual in the near future.

I said "I thought as much, because that's where I'd take it if we kissed. We'd do much more naughty things later on for sure. Not tonight, but definitely later. "

I also said it was hard enough just to get her out on this date (it took 3 weeks) because she had such a busy schedule. That it would drive me insane just to try to coordinate this regularly.

We laugh.
Then I walk her back to her car, not feeling the slightest bit rejected. We hug for real, and hold it for longer than normal.

I say "it was really good seeing a familiar face again." We commented on how we changed and how we stayed the same, then said our goodbyes.

That was it. I feel like I brought my best self to the date. Carried myself as a man. She appreciated it, but it just wasn't a good fit for either of us.

ONWARDS!

 

[Upstart]

SHE BOUGHT ME THE SHEETS, YALL!​

Friday, April 25th, 2025

I was FLABBERGASTED when I walked into her place the other day. The sheets she mentioned in her delirium were just sitting there on the counter.
We met up again two weeks after that encounter, so I was surprised she remembered.

She made me dinner because I said I was saving cash.
It was fucking delicious rice and stew. I drew a picture of her while I waited.


Andy recommended I start doing this on first dates, so I thought I'd give it a shot today as a thank you to her.

We watched the PJs then got to bed.

Notable moments:​

I FINALLY made her cum just from dick. I didn't think it was possible because I thought she needed a LOT of pressure to be able to cum, but not this time. All I did was swirl my dick around inside using a motion I learned from youtube. Instead of the constant jabbing we usually do, she did not expect this motion.

I was surprised I stayed hard the whole time.
Especially because I had to wear condoms because she was on her period.

I called the night early after we had dinner because I was dead tired and I knew I would rock her in the morning.

Morning came, we got to business.

I brought a mirror into her room to try some shit I read online.
But I wasn't sure what I was doing so I left it alone.

She bent down to suck my dick. Then we did some more stuff on the bed.

Her favorite thing is my fingers, which is basically the main event. I finger her with my left, which is what I usually start with. I touch her new spot again.

Then I really went in with my right when my left was tired. I blasted her with constant vigorous motion until she released EVERYTHING.

All her pent up frustration for the week exploded out. Ironically, there was no squirt.

She was writhing all over, grabbing her sheets, kicking her pillows off the bed while I stood back satisfied with my handiwork.

She nearly fell HEAD FIRST off the bed, lost in pleasureland. I caught her and said "I got you, I got you." and put her back on safely. She was at a complete loss of words. I should record it next time tbh.
Then she said,
"I get paid next week, you want half my paycheck? It's yours."

I just laughed and sucked on her titties as she slowly came back to her senses.
"I could see colors this time, all kinds. In a big swirl."

"Like a galaxy?" I asked.
"No, more like...a waterfall"

Damn, I wish I could nut like that too, lol.

She said, "I look forward to seeing you every week because I know you'll relieve ALL my stress from work."

Then I jerked myself to completion partially in her mouth, then the rest on her stomach, she says next time she wants it on her face.

Afterwards, I washed the dried period blood from my hands.

I said, "let me wash the blood of Jesus off my hands".
She died laughing.

After her shower she made me a VERY good breakfast. Her mom called and she said "sshhhh, it's my mom!"
I'm really glad this is still casual. And we both know it!
She sneezed and I accidentally said "Bless you"
Luckily my cover wasn't blown.

After breakfast, I was in no more mood for sex or even kissing, so she just cuddled and kissed me while I watched Abbot elementary. We stayed like that for 3 EPISODES, before I left.

She takes a real long time to say goodbye.

As a side note, this was my second 3 date week ever.

Russian lady on monday.
Childhood friend on Thursday.
FWB on Friday.