Well, here I am again. Back in my hometown, dolled up in an outfit with a note that reads "To Aidy, the best little Sister a girl could ask for! Have fun! - S.C." with a lipstick print I'm ashamed to admit I could tell you the exact shade, product line, and manufacturer of with 100% accuracy. Most guys, maybe not ones in their 30s like me, would be excited to have been mailed a kiss by one of the world's most famous and beautiful women, but most guys aren't that girls exact lookalike. I've spent so much time staring at her in the mirror that I've become entirely desensitized to her appearance. Maybe I was starting to look at her like a big Sister, she pushes me to do things I don't want to because she thinks they'd be good for me like a big Sister, which is why I'm wearing this red dress. To signal to the other Lookalikes that I'm one of them so we can network or commiserate. I didn't want to, I don't want people to know I'm a guy, I don't want them to know I'm in my 30s, I don't want them to know that these curves aren't padding anymore.
Sydney's Sissy Captions
Thursday, June 25, 2026
The Red Dress Trend - Sabrina
Well, here I am again. Back in my hometown, dolled up in an outfit with a note that reads "To Aidy, the best little Sister a girl could ask for! Have fun! - S.C." with a lipstick print I'm ashamed to admit I could tell you the exact shade, product line, and manufacturer of with 100% accuracy. Most guys, maybe not ones in their 30s like me, would be excited to have been mailed a kiss by one of the world's most famous and beautiful women, but most guys aren't that girls exact lookalike. I've spent so much time staring at her in the mirror that I've become entirely desensitized to her appearance. Maybe I was starting to look at her like a big Sister, she pushes me to do things I don't want to because she thinks they'd be good for me like a big Sister, which is why I'm wearing this red dress. To signal to the other Lookalikes that I'm one of them so we can network or commiserate. I didn't want to, I don't want people to know I'm a guy, I don't want them to know I'm in my 30s, I don't want them to know that these curves aren't padding anymore.
Wednesday, June 24, 2026
Tuesday, June 23, 2026
Monday, June 22, 2026
The Red Dress Trend - Rachel + Upcoming Schedule
Scheduled this for PM instead of AM and just noticed, so here it is a little late! I wanted to have these spaced out a little more, but I had a hand joint issue that made it very draining to type. So I did a mad dash to have things ready for the final week now that I have some mobility back in it. So this week we'll have at the very least 3 captions. Taylor Swift tomorrow and Olivia Rodrigo after that!
There won't be a new caption July 3rd, when I'll be posting the model poll to see what 4 beautiful ladies get captions in September. If you have any last minute suggestions please leave them in the comments!
Subject to change, but the plan for now:
July 3rd - Model Poll
July 10th - Blackedmail sequel
July 17th - Hawkeye vs. Hot Guy sequel
July 24th - Assignment sequel
July 31st - Hell Week sequel
August 7th - WHAT!? sequel
August 14th - Hiding the Evidence sequel
August 21st - Group Costume sequel
August 28th - The Dress-Up Mess-Up sequel
September will be the 4 model poll winners, October will, I believe, be the Fake ID conclusion. Then I'm probably gonna sleep forever.
As far as Lasspoint goes, I'm still posting the updates on DeviantArt, it seems to do really poorly on this blog, which I understand. It's not the usual content. If anyone is missing the story, it's there and I'll post it on a different, more accessible story site if anyone has suggestions.
Friday, June 19, 2026
Friday, June 12, 2026
The Red Dress Trend - McKenna
Guest cap by Jocelyn! Make sure to look at her blog! I thought it would be fun to have someone new to the world of caption-making to tell the story of the newest Looalike.
Friday, June 5, 2026
The Red Dress Trend - Sydney
Here's her red dress! Next week we have a guest cap from Jocelyn! Make sure to check out her amazing work, link to her blog in the sidebar.






