TG caption showing Alex confidently presenting as a woman in a modern CEO’s office, wearing a leather skirt and boots as she greets her unsuspecting boss.

Description

Alex steps back into the office presenting as a woman, convinced his disguise is perfect and his climb to the top has begun.

TG Caption

“Knock knock,” Alex said sweetly, stepping into her CEO’s office. “Just wanted to stop in and say hi.”

“Well, well.” Dean smiled, clearly thrilled to be interrupted by the sight of a beautiful woman, especially one unafraid to show off her assets. The tight leather skirt, thigh-high boots, and generous cleavage on display more than pleased him. “I don’t believe we’ve met. You can call me Dean.”

“Well, Dean,” Alex smirked, crossing her arms, pleased to see she hadn’t been clocked by her old boss. “I look forward to working… closely with you.”

Author’s Notes

Kicking off a new four-part series here. Hope you all enjoy where this one goes!

More TG Captions can be found in the TG Captions category.

TG caption showing Greg convincingly presenting as a woman after his sister’s makeover, wearing a floral dress and tights while nervously showing off the outfit in a bedroom.

Description

My sister swore this little makeover would keep me out of the draft. Judging by the way she’s looking at me now, she might be enjoying it a little too much.

TG Caption

“Okay, no laughing,” Greg said as he walked out of the bathroom to show his sister the outfit she had chosen.

“Honestly? You have nothing to worry about.” She smiled, clearly proud of her makeover skills. “Well, except maybe the men, if you get my drift.”?

Author’s Notes

Decided to try a new vertical TG caption. I used the title to frame the idea, and kept the caption itself quick and to the point. What do y’all think of this style?

More TG Captions can be found in the TG Captions category.

TG caption showing Chen dressed as a catgirl maid in a dark, red-lit bedroom, awakening to his loss of control

Description

Mark wakes from a hypnotic trance to find himself trapped in a humiliating catgirl maid outfit, powerless under his girlfriend’s control as she decides it’s time to try things her way.

TG Caption

Chen’s vision started to clear and his sense of self returned. He stood there in one of the most humiliating outfits, a catgirl maid, and there was nothing he could do about it. He couldn’t even move, trapped under the hypnotic trance of his girlfriend.

“Glad to see you’re awake, sweetie,” Amy preened, cupping his fake breasts from behind and giving them a squeeze. “I grew tired of your dominating behavior, so we’re going to try things my way for a while. So kneel, and open that pretty mouth, cutie.”

Chen knelt, his male self trying, and failing, to resist.

Author’s Notes

Take note of the background. Chen’s about to learn why details matter… eventually.

More TG Captions can be found in the TG Captions category.

TG caption showing Kyle presenting convincingly as a woman after a makeover, preparing to impersonate his twin sister.

Description

A flawless makeover turns a risky impersonation into a lucrative gamble, as Kyle and Sarah prepare to fool a bank teller and walk away richer than ever.

TG Caption

“We nailed it!” Sarah exclaimed, pulling Kyle into a hug. “There is no way anyone, and I mean anyone, could tell you are a man. Like, literally, you look so fuckable right now I almost wish I had a dick myself.”

“Geez, thanks, Sarah. I didn’t hire you to humiliate me, I hired you to make me look… well, like this.” He smirked, spinning so the skirt of his dress flared out. “I will admit though, I look convincing as hell. There is no way I don’t look like my twin sister.”

“Let’s hope so, because if we pull this off and you fool the bank teller, we are going to be two rich bitches.”

Author’s Notes

Starting to get into the swing of things. More to come, stay tuned!

More TG Captions can be found in the TG Captions category.

🖼️ An image version of this TG Caption is available here.

Description

Mark agrees to help his sister at the last minute, only to discover that a rushed makeover and a borrowed bridesmaid dress turn a private favor into a very public humiliation.

TG Caption

Mark couldn’t believe he was in a dress shop, trying on a bridesmaid dress for his sister, the bride. One of her friends had dropped out last minute, and after a rushed, humiliating makeover in front of the entire bridal party, Mark slipped into the dress.

The constant giggles and comments like “you look so pretty,” along with the smirks, only deepened his shame, but he owed it to his sister.

The final blow came when she secretly tagged him, en femme, in a Facebook post. His phone blew up, and suddenly everyone wanted to meet… the new girl.

Author’s Notes

Hope you like the video version of this caption. I will try to post more of these when possible. Picture captions will remain the priority, but you can expect more video versions in the future.

More TG Captions can be found in the TG Caption Videos category.