I MADE HER SQUIRT...TWICE (w/ pics)
March 1st, 2025
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.
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.
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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

)
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.
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.
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.