Penelope's Conquest

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

"Holy shit," I said, feeling tingles of pleasure race up my spine. "That feels incredible."

Penelope giggled. "What did I tell you? Life is all about new experiences."

I was sweating now, grinding my ass a little against the probing of her finger. I wanted more, but there were so many people around us. Strangers who, at any moment, could take a closer look to find a guy getting his ass finger-fucked by a girl.

"Can't we go back to your place?" I begged.

"Nuh-uh. I only bring home boys who want to fuck, and someone's not up to the challenge. I could drag you into the bathroom, but last time I made such a mess that security had to show me out."

I almost invited her back to my dorm, but stopped myself. That could mean exposure to Robby and Liz. And to anyone else I knew. I had spent so long trying to build up a reputation, and the idea of being known as a cockslut around campus was mortifying. Getting a cheap hotel was another thought, but I didn't have the money for that.

Penelope removed her finger all of a sudden, leaving my ass aching and empty. "Remember what I said about new experiences?"

"Yeah, of course," I said, wiping the drool from my chin.

She gave me a playful pinch on the cheek and stared into my eyes. "Do you trust me?"

"I guess I do," I confessed. It was the truth. I couldn't help but trust her. After all, everything she'd said so far was right. I wanted to experience new pleasures. That included all of her. Even her cock, if it came to that.

"Good boy." She squeezed my cheeks until my lips puffed up, like I was her bratty little brother who needed to be taught a lesson. "I can't take this teasing anymore, sugar. Get under the fucking table."

The beat of the music went muffled as I found myself under the cramped, low table of the nightclub booth. Then Penelope's womanhood was beside my face, its long shadow bobbing like a predator in the dark. She spread her knees to allow me access, and I could see the muscles of her thighs rippling. Her cock stood out in front of her like a third leg.

I had never been so ashamed in my life. An hour ago I had walked into the nightclub with my head held high. I was fine with another night of rejection, but there was always the hope that I'd find the rare girl to hit it off with, take home, and fuck -- how a man should.

Now I was on my hands and knees, hiding in public, kneeling on the filthy floor between a dickgirl's juicy thighs. Every breath I took filled my senses with the acrid odor of sweat and cock. When a beam of light swept over her, I noticed that even her cock and huge balls were glittering.

"Don't just stare at her, silly boy," Penelope said. "Didn't your mother ever teach you manners? Greet her properly. Give her a kiss on the sack and say hello."

Leaning forward, I planted my lips on her huge, dangling sack. Her balls were huge and hairless, and I kissed each of them carefully, delicately, like they were two precious objects. "Hello," I said, "nice to meet you."

Penelope snorted before laughing boisterously. I cowered against her leg, terrified that she'd draw attention and expose me.

"Sorry," she said, wiping away a tear. "I didn't expect you to actually say it. Don't look so embarrassed. I think it's romantic! And my girl does too." She poked the tip of her cock against my lips, leaving a string of precum down my chin. "Give your new girlfriend a kiss."

I pursed my lips and kissed the tip of her fat tender cockhead. It was smoldering hot. The idea of sucking cock had always repulsed me, but this was Penelope's cock, and her raw womanhood made it seem innately feminine, killing any disgust I had for the idea. I gave it a second kiss, and a third, then parted my lips to lick the slit. The taste was salty, but it wasn't terrible.

"Come on, sugar. Don't tease me all night." I heard her chuckle throatily to herself. "Who knows when your friend will get back."

The thought of being caught like this, crawling under the table like a dog, licking the huge cock of a woman I had just met, filled me with a burning fear. It also made me rock hard. I opened my mouth to accept Penelope's cock. The head was so thick and meaty that it was a struggle to get past my lips.

She slapped me across the face, grunting. "Watch the teeth, sissy."

"Sthhry," I said, my mouth stretched to its limits.

It was an ordeal to get the head of her cock past my lips, but once inside her size became more manageable. Well, at least her girth did. There was so much cock left to take. How could she possibly expect me to take it all?

"I knew you were the right one." Penelope reached under the table and pinched my ears. I blinked in surprise, staring at the length of her cock and her tight, flexing six-pack abs that had slipped out from under her dress. She truly possessed the body of a barbarian fantasy princess.

Then I felt her tug my ears toward her. I winched in pain, forcing my head toward her body, slurping in inch after inch of her slippery member to avoid getting my ears torn off

"Stroke my thighs. Massage my balls. Focus on my pleasure. Goddess, it's been a long week. You have no idea how much I've needed this."

Part of me wanted to pull away from her fleshy rod, accept the shame of being seen, and run far away from the nightclub. But one glance at her stunning female body turned my mouth into a living fleshlight. I took her deeper, slurping loudly, wanting nothing but to gain her approval. The worst part was, she was barely moving at all. All the effort came from me. I was skullfucking myself.

"That's the spot," she cooed. "There's something special about having a stranger's mouth around your cock. Have you ever got a girl to suck your cock so fast? It took me less than fifteen minutes to get you on your hands and knees and my dick in your mouth. That might be my new record. I've got a silver tongue, after all."

I hated her at that moment. It took me weeks, if not months of getting shot down to get a girl to hook up with me. I wanted to curse at her, to call her a cruel evil bitch. I kneaded and pinched the inside of her thighs, hoping to punish her a little, but she only squealed in delight.

"Mm, that felt nice! Now you're getting into it. Don't forget to rub my balls, too."

While my taste buds savored the salty-sweet flavors of her cock's steamy underside, I reached a hand to tickle her heavy ballsack, feeling the moist hairless skin. I pictured her strutting around the courtroom, her fat womanly package stuffed into a pair of lacy panties as she addressed the judge, the witness, or the men and women of the jury. She was powerful. It made sense that her cock was powerful, too. I was a penniless computer science student. What chance did I have to resist her?

"Sweetie, I've got some bad news," Penelope said. I looked up to find her frowning down at me. "I think your friend is on his way back."

My eyes went wide. I tried to crawl backward and hide my shame, to unsheath her dick from my mouth. All of a sudden her hand was gripping my head, and her legs wrapped around me, resting on my back, impossibly powerful. Locking me in.

"Nuh-uh, sugar. You don't get to leave till I'm good and satisfied. I am NOT getting blue-balled on Saturday night.

I stared up into her eyes, begging for mercy. Her face was lusty and unsympathetic. I knew I couldn't escape. A sense of submission overwhelmed me. She could destroy me if she wanted to. My reputation, my body, my life. And I would let her do it.

"Take me into your throat," she hissed.

I crawled forward on the filthy floor, forcing myself closer to her. Her fat throbbing girl dick burrowed into my throat one agonizing inch at a time. She was filling me, stretching me, flooding me with her heat. My face was sweating and I couldn't breathe. My tongue savored her every inch and I could feel every pulse and throb, like she was now a part of me. Her sweaty, female smell was seeping into my brain.

She stroked my hair affectionately, no longer forcing me, as I worked down the last few inches of her pornstar cock. It stunned me to feel my nose crushing against her tight pelvis, her huge dripping ballsack smearing out against my chin.

"Faster. I'm close."

I began to pump my head a few short inches at a time, no more than a sex toy for this hung goddess. I stroked her abs, felt her wide hard hips, massaged her thighs. Anything to make her feel good.

"Oh my god, Penelope!" someone said.

I froze, wide-eyed, and hid my hands under the table. A chill of fear ran through me, despite the steaming girl-stick stuffed down my throat.

That was Liz's voice.

My heart raced.

Please don't sit down Please don't sit down Please don't sit down Please don't sit down.

Penelope quickly lowered her dress, covering the top of my head. "At last, the lovebirds make their return." She managed to sound nonchalant. Her legs pulled me into her, though, and I felt her hips rolling gently, churning her cock in my throat.

"Shit, I can't believe that little dickhead left," I heard Robby say. "I am so sorry about him."

"Dickhead?" Penelope laughed, and I felt the vibrations of her laughter travel through her cock. "That's one way to describe him. John... Jeremy... what was his name again?"

Furious, I gripped her cock with my throat. Had she really forgotten my name?

"James," Robby corrected her.

Out the corner of my eye, I could see Robby's shoes beside the table, just a few feet away. I forced myself to stay perfectly still, nursing her throbbing length down my throat, feeling it throbbing there, at full mast. I could barely breathe. I wanted to slap her thighs and beg her to let me go. But breathing was less important than not getting caught. I would sooner die before letting Robby see me on the ground, filthy and pathetic, with a huge female cock down my throat.

"That's the one," said Penelope. "I think he stepped out for a second. In fact, he said he was looking for you. You should probably run after him."

"Shit, I'm so sorry about that. He can be such a loser sometimes." I heard Robby peck Liz on the cheek. "I'll be right back."

I watched his shoes disappear. Then Penelope moaned wantonly and began to buck her hips, fucking my skull. I slurped desperately, tears streaming down my face. Then I looked sideways and saw that Liz's high heels were still standing there, right beside me.

"Are you serious right now, Penny?" she said.

"You know how I am." Chuckling, Penelope lifted her dress to expose me, cock down my throat, to her blonde friend. I tried to pull away and hide my shame, but Penelope's thrusts were inescapable. Liz stared at her friend's new sex toy, balls slapping my chin, and all slop and spit staining my face, and burst into laughter.

The nightclub lights swept over us as Liz took a seat next to Penelope. With tears in my eyes, I looked up at the pair of grinning lawyers. The blonde affectionately stroked my hair, as if comforting a pet, while Penelope took my mouth and throat with long, pounding thrusts.

"Here it comes, lover boy. Get ready for--mmm-- a whole new experience!"

I glared up at the two smirking, cocky bitches as the salty flood of girl spunk erupted into my mouth. Penelope came like a fire hose, emptying her hot sticky cream inside me. The smell of her seed was overwhelming, and its temperature seemed close to boiling. I gulped down her cum like my life depended on it, felt it surging down her rod with my tight, squeezing lips. Desperately, I reached out my tongue and lapped at her huge, swinging sack. My vision went dark as my forehead pressed against her tight abs.

"Suck down my cum, slut." she growled. I heard her take a swig of my beer, then set it heavily on the table. "I'm sure it tastes better this pissy beer you were drinking, doesn't it?"

Liz snickered. "Oh, you are so mean! Was he seriously blowing you this whole time?"

"Most of it," Penelope said, sounding a little weary now. "Don't give me that look. A girl's got needs."

At last, the flood of girl spunk stemmed off. Penelope put a finger against my forehead and pushed. I gagged as all twelve inches of girlcock slowly unsheathed from my throat, dripping with saliva. I gasped for air on my hands and knees, until I felt her tugging my ear. "Don't be so dramatic. Sit up here next to us, like a big boy."

I crawled up into the space between the girls, panting heavily. Penelope leaned back and relaxed, seemingly uninterested in me now. Liz made a sympathetic face, but the way she looked made it obvious she was holding back laughter. She handed me a napkin and I began to wipe the spit and cum from my face.

"How could you tell he was a cocksucker?" she asked.

"He didn't know it yet, but after a while you just know how to pick 'em. How were things with your future CEO?"

"A bit of a quick shot, but at least I didn't get us thrown out this time. Unlike someone I know.

Penelope laughed. The girls reached above my head to high-five each other.

"Wait," I interrupted, my voice hoarse, "is Liz also--I mean, does she also have a..."

"Of course not," Liz said. "I'm one-hundred percent woman. And your roommate" --she paused to giggle-- "he's quite a guy! The four of us should totally do this again sometime."

"I guess we could," I said, conflicted. Part of me wanted more of Penelope, but I knew that any more of her could have a permanent effect on my life. It was frightening. And there would be the chance of Robby finding out, and he would surely tell the rest of my friends...

Taking a sidelong glance at her, my heart raced. Every atom in my body wanted her body, her approval, her affection. And maybe more. My cock was like iron in my pants, and that made me furious. I wanted to fuck her face and cum too. The bitch had gotten all the pleasure she wanted, but hadn't once considered my needs.

"Aw, I think you scared the poor thing," Penelope said. She took a napkin and helped me wipe the spit and sweat from my face. But the material was thin, so it took her a while to dab away the mess. "Clean enough. Now stuff my cock back into my panties before it gets hard again. There you go. See, Liz, how easy it is to control these boys?"

Liz rolled her eyes. "I wish I had your talents."

"Holy shit, man. I was looking all over for you!" Robby said, hurrying back to the table.

I sank in my seat. "I was just in the bathroom."

"What the hell happened? Your face is a mess, and your shirt is all fucked up!"

"I slipped and fell down," I lied.

"He might have had little too much to drink," Penelope teased, patting my back.

I burped unexpectedly, as if to prove my point. The pungent flavor of her girl spunk filled my mouth again.

Robby glanced at Penelope, then Liz. I must have looked impressive, sitting between the two of them. "Sure you did, man. Well ladies, it's been fun, but I think we'd better call it a night."

"Bye lover," Liz said, leaping up to give Robby a kiss. "Don't forget to text me!"

I stared at Penelope, hoping to get a similar reaction. But she just sat there smiling, and gave me a wink. "See you around, sugar."

Robby was almost jumping with excitement by the time we got outside. "You little horndog! I wasn't sure if you had it in you. Even I thought that babe was out of my league!"

I chuckled self-consciously. What had actually happened under the nightclub table, I planned on taking to the grave. "What can I say? I guess I got lucky."

But Robby was hardly listening. He was already on his phone, typing furiously.

"What are you doing?" I asked.

"Sending that little slut a text. We have definitely got to see them again! I'm inviting them over to the dorm this week."

"Are you sure that's a good idea?"

Robby slapped me on the shoulder. "Hell yeah it is. Man, you better be grateful for helping me get you laid for once!"

"Yeah," I said, feeling the soreness in my throat. "Thanks. I guess I owe you one."

Robby wore a face of satisfaction as we began the long walk to our dorm. But my cock was still throbbing, and I knew the first thing I would do when I got home was jerk off to the thought of Penelope and the feeling of her cock down my throat.

12
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
18 Comments
sissyboi69Aricsissyboi69Aricover 1 year ago

I loved this story, please continue

AnonymousAnonymousalmost 2 years ago

Please continue. This was so good and you don't see many like this

GrrrreatImaginationGrrrreatImaginationabout 2 years ago

Great storytelling. It would be great to see this develop into a series for a bit.

AnonymousAnonymousabout 2 years ago

Great start! Please continue

AnonymousAnonymousabout 2 years ago

God, I loved this story! The way Penelope seduced James was so hot. Just every little thing she said and did. And the way she treated him when he was under that table, my God. That entire scene was just perfection, just the right combination of affectionae and rough.

I also gotta say, I really like her cool, incredibly confident personality as well. I would love it if you could write a sequel to this sometime.

Show More
Share this Story

Similar Stories

Futa House A boy unwittingly discovers a gold mine of girlcock.in Transgender & Crossdressers
The Bet Hung girl wagers that Billy will love her cock in his ass.in Transgender & Crossdressers
In Time for Summer A boy gets seduced by his "lesbian", packing roommate.in Transgender & Crossdressers
Shemale Bar Straight guy goes into a shemale bar and is forever changed.in Transgender & Crossdressers
The Big Mature Shemale Next Door Little guy is fed cum and seduced.in Transgender & Crossdressers
More Stories