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
The Red Dress Trend - Olivia
I was hoping that the clip in question would suffice, even if I'm not technically wearing a dress, a video of me in a red outfit posted at the same time the Red Dress Trend was going down should be good enough, right? I'd like to reach out, talk to some people about how embarrassing this gig is, or at least maybe I could get some tips on how to be less anxious about it. Part of me thinks I shouldn't complain because I really don't have to do much compared to some other stories I've heard. I can't confirm all, or any, of them obviously, but I've heard Taylor Swift's Lookalike has it way worse than I do. Unfortunately, unlike the rest of them I can't just do my hair, throw on a red dress and suddenly become Olivia, this job is something I wouldn't be in any way qualified for in any way, most of the guys they get apparently have a strong resemblance to their celeb already, I can only look like Olivia with the heavy involvement of technology and I'm not working tonight, they offered a chance to get dolled up but I'm hanging with my girl tonight and as excited as she gets about having an exact clone of her favorite pop star around, I don't like the completely non-boyfriend way she looks at and speaks to me when I'm in my "uniform."
This actually started because of her, my name was Bayley back then, it still is, but so few people use it anymore. When it was announced that Olivia would be making a stop near us on her tour, my girlfriend flipped. I wanted to get a pair of tickets as a gift, she really is the best thing that ever happened to me. I saved and saved and sold a good chunk of my video game collection and when they finally went on sale, they sold out immediately. I managed to find a scalper willing to part with one of their tickets, but all of my saving only amounted to most of one ticket, had to pay the rest with my grocery money but I got it! My girlfriend was at first excited, then crestfallen to find out it was one ticket and I wouldn't be attending. There's no way I'd be able to afford another ticket so I figured I could bust out my IT skills and get myself in there, I scanned the ticket and tried to make another but the coding was tricky so I used an AI program to create a crew pass for myself. I could use it to get in, slip into the crowd, find my girl and enjoy the night. Maybe I'd be able to get some merch or an autograph and win boyfriend of the year.
When we arrived, she got in the audience queue and I went to the staff entrance of the venue. I inhaled deeply, gathered all of my nerves, then scanned the pass. The light turned green on the terminal and it told me where to go, I didn't want to draw suspicion, so I'd just go to whatever room I was supposed to, act busy until nobody was looking, then slip out. As I entered the room I was directed to, it was a sterile, white room with a single chair and several panels on the wall. Another terminal asked to scan my pass, I did, and it lit up "welcome, Olivia" before the panels on the walls started to shift and several metal tentacle-like objects came out and restrained me as it got to work on me. I feared for my life but then I realized it was tearing m clothes off, I then feared for my everything else. It sprayed me with a chemical-scented liquid that burned at first, then sprayed me down with water. I realized my body hair had washed away. A large hourglass-shaped contraption approached me, then split in four and surrounded me, encasing my body save for my arms, neck, and head. I felt it squeezing and coating me in something. I then felt a tense, tight pressure on my crotch. It hurt. I tried to shout but a mask made of the same material as the hourglass dropped from the ceiling and encased my face. A tube shot down my throat to help me breathe. I tried to rock, writhe, and fight but I was powerless to move anything. I don't know how long I was there but I resigned myself to my fate until it opened and dropped me. Everything returned to the way it was and one of the panels shifted and there was Olivia Rodrigo or...
No. It was me. I was Olivia Rodrigo. Why was I Olivia Rodrigo? It had cinched my waist, added padding, hair extensions, make-up, compressed my face into her shape, added a supplement to freeze my face in place as an exact copy of Olivia's. It could still function but wouldn't return to my shape. I was wearing an outfit that consisted of a red bodysuit, black pantyhose, and some platform shoes. Then the panel shifted to reveal another mirror except I was, wait no. That's really Olivia Rodrigo. She looked entertained at the sight before her. She walked over and eyed me up and down without a word, picking up my personal belongings that the tentacles had placed on the seat. She opened my wallet, looked at the ID, then at me, then showed it to me. "You're a guy?" My hand subconsciously went between my legs to feel the smooth, pressed-in flat area under my outfit where the proof used to be. I nodded. She asked how I accessed her auto-dresser. The only thing I can assume happened is that when I asked the AI to make me a pass to the Olivia Rodrigo concert it somehow pulled the data from her actual ID and put it in the code of the pass, but that sounds mighty illegal so I just mumbled a response.
"I'm lost."
"I'd say you're found is more like it. They asked me to try this auto-dresser out tonight and it... Looks like it does a phenomenal job." Olivia said, circling and inspecting me.
"I um... I can leave. I'm sorry it's..."
"No! Your voice isn't quite there yet, but I have an idea. Let's see if this auto-dresser is good enough to fool my adoring fans. If you can go onstage without anyone noticing, I won't tell anyone anything."
"I can't sing."
"You won't have to, just get me some time to relax between songs, we'll say there's an issue with the mic, just dance, tease, entertain them a little. When I'm ready to come back I'll relieve you of your duties, you can get out of here. Heck, you can keep the outfit." I didn't have much choice. I nodded. The concert went on, I texted my girlfriend and told her I was stuck backstage before I went on, Olivia sliding past me, slipping me the dead microphone, giving me a slap on the ass and wishing me luck. I scanned the audience for her, then realized I was just staring like a deer in the headlights, so I started doing random dance moves, lip-synching to the random playlist they played between songs as the band took their break. I'd finally spotted my girlfriend, pointed directly at her and smiled as she took a selfie of the both of us from a distance. That made quick work of the frown she'd been wearing at the fact I wasn't with her.
Afterward, I went backstage to realize that the machine had destroyed my old clothes. Olivia offered me a trench coat to sneak out, not before a man in a suit told me he worked for a company called LALS and let me know that his company was purchasing an auto-dresser and would like to offer me work as Olivia's double. That was the quickest "no" I ever said. Then he told me how much I'd make and, well, my girlfriend and I had a lot to talk about on the way home after I got her to stop screaming at who she thought was Olivia Rodrigo approaching her to drive her home. So, that's what I've been doing for work since. My girlfriend loves the merch, the free tickets, she's even been able to meet Olivia a few times. I don't like how Olivia likes to tease me by picking especially feminine outfits for us on nights she knows my girlfriend will be there. That babydoll? Yep. Had to wear that our anniversary dinner. It's all well and good as long as she's happy, but I've noticed that when I'm in my work clothes, she doesn't view me as a boyfriend at all. She likes to gossip and play like we're two besties, I've even caught her accidentally beginning to vent about me to "Olivia." But I guess I can take solace in the fact that it really only had to do with her missing me. A bit odd to phrase it as "I miss having a man around," instead of "I miss having Bayley around," but hey, at least she still cares about the real me.
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.






