This is the story of Belinda and her unexpected sissy taxi ride in New York City…
“Sissy Belinda?” It was Tessa on the other end.
“Yes,” he answered.
“Where are you? Has your plane landed?”
“Yes, it was early for a change. I’m on my way to the hotel now,” Belinda replied.
“Did you go shopping like I asked you to?”
“Yes,” he whispered. His heart skipped a beat.
“What did you get?” Tessa asked.
“You know…um…everything on the list.”
“Remind me again what was on the list. I’ve forgotten.”
He looked hesitantly at the cab driver, a burly New Yorker. “Um, Passion Pink lipstick, black mascara, nude colored stockings, orange nail polish, and,” he lowered his voice, “and tampons.” The taxi driver looked at him in the rearview mirror.
“I didn’t hear that last part,” Tessa chided.
“Tampons,” he said slightly louder. The taxi driver raised an eyebrow.
“Bonbons?” Tessa asked.
“Tampons,” he said louder. The taxi driver chuckled.
“Okay. Good. Now, what things did you pack in your suitcase?” Tessa asked.
Oh god, why does she have to keep going on and on, Belinda asked herself.
“Um, honeystick lip liner, purple liquid eye liner, and a lilac eye shadow trio,” Belinda said aloud.
“Um, eyelash curler.” His mind recounted what else he packed from the sissy shopping list she provided.
“Belinda, you’re in a taxi, I assume.”
“Put the taxi driver on the phone,” Tessa instructed.
“But…but why?” Belinda stammered.
Tessa sighed. “Belinda, just do it.”
“She wants to talk to you.” Belinda slowly handed the phone to the taxi driver. The taxi driver took the phone, surprised.
“Hi, I”m Tessa. What’s your name?”
“Hank, nice to meet you. Listen, you heard all those female items your passenger was talking about?”
“Well, those are all for his use.”
“You’re kidding!” exclaimed Hank.
“Nope, he’s a sissy boy. And I’m his Mistress.”
“Oh, is he married?” Hank chuckled.
“No, not that kind of Mistress. God, I wouldn’t let him touch me like that. Although sometimes he cleans me out after my boyfriend has fucked me, but that’s beside the point. Anyway, are you taking him to a nice hotel?”
“Yeah, very clean and in a safe area,” Hank replied.
“Good. Oh, ask Belinda – -“
“- – Who’s Belinda?” Hank asked. Belinda blushed and slid down a little more in the backseat.
“Belinda. That’s his name. Ask Belinda if he packed his pink corset?”
“Belinda, did you pack your corset?” Hank laughed.
“Yes,” Belinda murmured. She turned a deeper shade of red.
“Yeah, he did.” Hank responded into the receiver.
“Ask her if she packed her eight inch purple veiny dildo.”
“Tessa wants to know if you packed your big purple dildo?” Hank chuckled.
“Yes,” Belinda whispered. Her tie seemed tight, so she loosened it.
“Yeah, he did,” replied Hank.
“Ask her if it’s the purple one with the balls attached. She’s such a whore and has so many dildos and butt plugs, it’s hard for me to keep track of all of them!” Tessa said.
Hank guffawed. “Is it…is it the one with the balls attached?” Belinda could only nod at this point.
“Yeah, he’s got it,” laughed Hank.
“Good, she’s gonna have fun tonight! Oh. Ask Belinda if she’s wearing her pantyhose now.” This was too much for Hank; he wiped laugh tears from the corners of his eyes.
“You got your pantyhose on?” Hank asked.
“Yeah,” Hank told Tessa.
“Hmmm, she might be lying. Ask her to show you.”
“Tessa said you gotta show me.” Belinda felt a bit dizzy as she placed her foot on the seat in front and lifted her pant leg. Hank quickly turned to look. He grabbed Belinda’s ankle and stroked it. “Yep, he’s – she’s – got her hose on.”
“Good. What about her bra? I want her to show you, too, just in case.”
“Got your bra on?” Hank was clearly enjoying himself.
“Yes,” croaked Belinda. Can this get any worse, she wondered.
“Prove it!” Hank responded.
Belinda unbuttoned her shirt, her tie already loosened at the neck. When they came to a stop light, Hank turned around. “Yeah, it’s red,” he said to Tessa. To Belinda, he said, “Nice tits.”
He squeezed Belinda’s C-cup breast forms.
“Is she wearing her panties?” Tessa went on.
“Hahaha! Hey, you got your panties on?” Hank asked Belinda.
Resignedly, Belinda pulled her shirt out, unbuckled her belt and undid her pants. A patch of red satin showed. Hank quickly turned to look.
“Yeah, red panties.”
“It’s Belinda’s time of month, and I’m concerned if she’s wearing her pad. Could you check?” Tessa asked. At this, Hank put the phone down, threw his head back, and laughed. Between gasps for air, he picked up the phone.
“Is this some kinda secret camera show?” he asked.
“No, I assure you, Hank, this isn’t. Belinda is a sissy, albeit a rebellious one. I try to keep her in line, but I can’t always be there to make sure she’s being a good girl.”
“Hey, your Mistress says you’re on the rag now, and I gotta make sure you’re…uh…prepared.” Hank chuckled.
Belinda’s eyes widened. Tessa had never gone this far before in exposing her as a sissy. Belinda’s mind raced for an excuse, an escape from this sissy taxi ride, anything. But she knew she couldn’t escape from Tessa; she knew no excuse would work for Tessa. Belinda lifted her bottom up and pulled her pants down to her ankles.
“Whoa! He’s, I mean, she’s, got a garter belt on, too.” Hank peered at Belinda in his rearview mirror. Belinda rolled down the front of her sissy panties and showed the pad that was stuck onto the inside. Hank pulled to the side of the road, stopped and turned around.
“Wow! Yeah, she’s got a pad on. He ain’t no she…if ya get my meaning. But damn if he don’t look like a she, or is it she a he?” Hank turned around and drove on, laughing. Belinda hurriedly dressed, knowing the hotel was just around the corner.
“Okay, yeah, sure.” Hank handed the phone to Belinda.
“Belinda, please tip Hank a hundred dollars. Sissy babysitters can be very expensive, but he was a good one. Talk to you later.” Tessa hung up.
The taxi pulled up to the front of the hotel. Belinda adjusted her tie and looked like a normal traveling businessman. Hank retrieved the carry-on from the trunk. He handed it to Belinda, who paid the fare and tipped Hank according to Tessa’s instructions.
“Thanks, Belinda,” Hank yelled. Belinda cringed because a few hotel guests and a valet driver overheard. Belinda walked to the front desk and began checking in, relieved to be rid of Hank. As the desk clerk handed Belinda her room keys, Hank walked up.
“Tessa told me that since you’re on the rag now, you get extra horny. She said you probably want a cock to suck, so I’ll bring a couple friends by after my shift. See ya later.”
Hank left. Belinda’s knees wobbled at the thought of that sissy taxi ride. The desk clerk looked disgusted. And the little blue haired old lady behind Belinda gasped.
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