So Thoroughly Defeated

Story Info
You take your sissy for a walk around the city.
1k words
4.23
10.3k
5
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

With a leash in hand, you walk through the park, leading your pet sissy towards a man in the shadows. He's standing behind a big oak tree with his cock out in the middle of the night, gently stroking while he eyes your bimbo. "God damn. She's so fucking sexy."

The comment makes you grin with pride. "Get your ass over here, bitch." You snap at Annabelle. "Let the man cum on your face."

"Yes, sir," she replies in a hushed voice, quickly adjusting herself beneath him, ass hanging out of the skimpy pink skirt you made her wear.

"That's a good girl." The man revels in her submission. "Can I spit on her face?"

"By all means. That's what she's meant for."

"Appreciate it." He smirks and leans down. Ptui! "How's that taste, you dumb fucking bitch? You like swallowing spit for random men?"

"Mhm," Annabelle whines. "It tastes so good. Thank you, sir."

"I bet you want more, don't you?"

"Yes please... I need it so bad!"

The man's smile widens, and he unloads a big wad of spit onto Annabelle's face before slapping his cock down to rub it all in. "Look at you, taking dick, like the whore you are — open your fucking mouth!"

As she obeys the man, you decide it's time to get in on the action. You squat down behind Annabelle, reach into her ruffled skirt, and pull her cock back from between her legs. "What kind of 'man' crawls around and gets treated like this?"

She answers with the sound of wet cock being slapped against her tongue.

"ANSWER ME, BITCH!" You squeeze her balls.

"Ahh, ahh!" She turns her head to address you. "I'm not a man! A man doesn't do this."

"GOD DAMN RIGHT YOU'RE NOT!" Your yelling turns into laughter as you imagine what the people in Annabelle's life think she really is. If only they could see her now — you holding her, making her whimper. "Holy shit. You're such a little bitch!"

"Mmm, mmm, mpphhh! Thank you, sir!" she says, sounding appreciative of the compliment.

Later that night, after the man by the tree has had his fun, you lead Annabelle down a stone alleyway. You can tell she's getting uncomfortable from crawling around the city all night, so you ask her if she needs a break.

"Only if you think I deserve one," she replies with tact.

"Good answer. Broken sluts don't take breaks do they?"

"No, sir. They don't."

"That's absolutely right." You tug on her leash. "Plus, we're almost there. Your pretty ass can wait another minute."

Turning the corner into an empty lot, you see the four men you'd agreed to meet — they catcall your sissy once they notice her presence.

"Look at this fine thing."

"Why are you out so late?"

"Who bought that skirt for you, babygirl?"

Hearing their words, Annabelle's crawling speed slows, and she tries to hide her face. Aww, poor thing must be getting shy, you think to yourself, stopping to let the men crowd around her. One of them runs his hands along Annabelle's forehead, parting strands of hair from her eyes. Another lifts up her skirt, showing her ass for the group to see.

"Fuck!"

"Shit, baby."

"What do we have for her? I wanna see how much this pretty ass can spread."

"You don't mind if I show her what's good, do you?" The biggest one kneels behind her and starts lubing up his hand.

"Please do." Your cock rises in your pants. "The fuck else is she good for?"

"What else does she gotta be good for? With an ass like this." The man spits in her hole while the others pull out their cocks.

"Good point." You chuckle. "This is all she'll ever need."

He nods in agreement and pushes his hand in.

Annabelle's ass swallows the fist whole. She lets out a set high-pitched moans that sound like they're straining her voice. "Uh, uhh, uhhhh!" She shivers, trying to rest her face on the ground for relief. But the men gathered around her aren't having it. They grab her by the throat and kiss her lips, reminding her that she'll never be a man.

When they're all done playing with your sissy, poor Annabelle is shaking, trying to recover. Her hole opens and closes, probably never to be the same again. "How'd that feel?" you ask. "Being spread open by a group of men?"

"It's all I've ever wanted," she says.

"Good. It's all you're ever gonna get... Now, follow me. You've had enough time to rest." You tug her into motion and lead her to a private club, where purple neon lights illuminate the shadows.

Inside, she's met with applause and jeering laughter as you parade her around, naked, cum and spit all over her face.

When she's more than made her rounds, you hoist Annabelle onto the bar and follow her up, a burning sensation in your system. Her back eases to the counter, smooth legs over your shoulders, necessitating the removal of your pants.

Kneeling in front of her, everyone watching, you lean in. Jaws drop. Heavy breaths. The men in the room sound jealous. Several of them pull their cocks out, getting in as close as they can while your dick glides inside her.

The bartender comes over and starts pouring alcohol on Annabelle's face, like he's trying to waterboard your sissy with free drinks. Annabelle swallows whatever he's spilling, doing her best to keep up with the steady flow of liquid.

Too horny to care if she can breath, you grab Annabelle's dick and stroke it with two fingers. And that's all it takes to make her melt underneath the weight of you. She shakes and shivers, no control over anything. "That's right, sweetie." You hook yourself up in her gut. "Look how easy it is to defeat you!"

Hearing that, she bursts in sync with you. Violent contortions against your belly and your sides as she tries to cling to your waist. But her mind is too weak. She can't find the strength. So, you lean down and wrap your arms around her, bringing her head to your chest as the men in the bar cum all over your back.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
2 Comments
AngelicaAlbrightAngelicaAlbright9 months agoAuthor

Hello, and thank you for reading! Yes, this was a repost. I made some minor adjustments based on community feedback.

the6ulprsnthe6ulprsn9 months ago

Definitely read this before. But I’ve been here lurking a long long time. To be fair, it could be a repost.

Share this Story

Similar Stories

Making of Tina Ch. 01: Caught A story about forced feminization.in Transgender & Crossdressers
Sissy Gurl at the Gloryhole Sissy gurl becomes a dirty whore at the ABS.in Transgender & Crossdressers
Sissy Whores Inn Daddy tracks down his runaway son in sissy whores hotels.in Transgender & Crossdressers
My Roommate's Maid Pt. 01 College student forced to be their roommate's sissy maid.in Transgender & Crossdressers
My Adorably Hung Summer Roommate Darren meets Danielle, a petite redhead w/ something extra.in Transgender & Crossdressers
More Stories