Penelope's Conquest

"Just have a drink and play it cool, man."

Robby shoved a cold beer into my hands as we followed the girls off the dance floor. Leading the way was the perky blond he'd picked up at the bar, his conquest for the evening. Small, tight, and bubbly, the usual type of chick he brought back to the dorm.

That left me with the blond's friend, a towering statue of a woman. Olive-skinned and hazel-eyed, with a brunette pixie cut. An impressive spectacle of six feet of muscles and thick womanly curves. It was hard to believe she was real. She looked like she'd walked off the cover of a fitness magazine. Or a fantasy novel.

I had spotted her coming in -- who wouldn't have? -- but I never expected to find myself actually meeting her. Women like her had a type, and it sure as hell wasn't me. At least I didn't think so. Still, my friend had a way with women, and I was all too used to playing the wingman.

The blonde dragged Robby into a little empty booth. He stumbled and fell on top of her, and the two of them roared with laughter as they untangled themselves.

I straightened my collar, trying to look sharp for the tall woman. I had put on my best shirt before leaving the dorm, made from delicate Egyptian cotton. But I doubted even the most expensive clothes could have helped me get a chance with her.

"I think they might be a little drunk," I said.

"So am I," said the amazon. "Scoot in, sugar." She squeezed my upper arm as she guided me into the booth. Her grip was gentle, but firm. It was a little intimidating, like I didn't have much of a choice.

You're overthinking things again, I scolded myself as I set my beer on the table. Ms. Pixie tucked in after me, settling her fat ass into the faux leather seat. Her movements were less feminine than I'd expected. She relaxed with her arms on the backrest and her legs spread apart. She seemed to take up the space of two people, forcing me against the wall of the booth until my knees were pressed together.

It was uncomfortable as hell, but I kept my thoughts to myself. If I fucked things up for Robby, I'd never hear the end of it. That besides, the amazon's leg was pressing my thigh, and her skin was hot, hot enough to feel through the fabric of my pants. My cock throbbed a little.

Two hours ago, I'd been looking forward to a relaxing Saturday night of video games and porn. Now I was sitting next to a chick who probably worked as a fitness instructor. Even if I doubted I could get laid, I wasn't about going to ruin a good thing. At least not intentionally.

Robby and his blonde were whispering into each other's ears. I sipped my beer awkwardly, not knowing what to do or say. I hated how the loud nightclub music was; it made it hard to think, and thinking was about all I was good at.

"Well, are you just going to sit there?" the amazon said to me, raising her voice over the music. Despite her killer body, her nose was pert and her cheekbones high and delicate. Her lips were plump though, and wet. She was so beautiful that it was difficult to look at her. "This is the part where you introduce yourself."

"Oh my god, don't bully him," the blonde chirped. "I'm Liz and this is Penelope. Don't worry, she's not as scary as she looks. Well, not unless she really likes you."

"That's good to hear!" I said, chuckling awkwardly. I offered the tall woman my hand. "You can call me James."

"I can call you all sorts of things," Penelope said, giving my hand a shake. "Wow, your skin is so soft."

"Thanks," I said, a little embarrassed. Her fingers were long and her grip was firm. I could feel the calluses on her palms. She was definitely the type to spend serious time in the weight room.

"And this is Robert," said Liz, throwing her arms around my roommate's neck. "Robert, Robert, Robert. I love saying your name!"

"And I like saying yours... what was it again?" Robby teased. Laughing, he pulled the tiny blonde against his sturdy frame. It amazed me how fast he worked when it came to women. I guess his looks had a lot to do with it. Whenever we went out, I was always the smaller, skinnier, shorter wingman. It made me jealous, how often he brought girls back to our dorm. I had only gotten lucky a couple of times, and they never clung to me like that.

I sat up a little when I felt Penelope's hand on my thigh. "So, what do you do for a living, James?"

"I'm, uh, a student, computer science," I muttered, a little embarrassed by my choice of major. We had a pretty rough reputation around campus.

"And I'm a future businessman," Robby bragged. "I'll probably end up Jimmy's boss someday!"

"You're so mean," Liz giggled, slapping his chest playfully.

"We picked up a couple of college boys?" Penelope said to Liz. Her nails dug into my inner thigh a little, like she wanted my full attention. I bit my lip to stifle a groan.

"You ladies didn't pick up anyone," Robby said. "I'm the one who picked up a couple of working women!"

The girls laughed, and I forced myself to join in. I suspected they were drunk enough to find anything he said funny. Then Liz was all over him, hands and mouth at his neck. I looked away, uncomfortable with their public display of affection.

"So, Penelope," I managed to speak, trying to make things less awkward, "do you come here often?"

I must have sounded dumb, because everyone burst out laughing at my clumsy attempt at conversation. Penelope's was deep and unapologetic, not at all like Liz's bright tittering. When she finally finished, her body relaxed heavily against mine, closer than before. She was surprisingly firm under all those curves; I could feel the shape of her muscles, tight and sturdy. Her navy minidress looked like a flimsy bath towel against all that hard flesh. She smelled strongly of perfume and sweat, and when the nightclub lights passed over her, her olive skin sparkled.

"I'm something of a homebody," she said, grinning down at me. Her smile was so close now. I could see her perfect teeth and smelled the alcohol on her breath. "Unless my partner in crime over there drags me out."

"Wait, seriously?" I said, relieved. Maybe we had more in common than I thought. "I'm totally the same--"

"Don't listen to a word she says," Liz interrupted, breaking from Robby's lips. "Liz and I are junior attorneys. It's a totally stressful job, so we go out, like, every weekend!"

"Wow, that's impressive!" I said, trying to sound convincing. It was hard to believe that the ditzy blond and her athletic friend were lawyers. I stared at Penelope's threaded eyebrows and her boyish pixie cut. I suppose she could appear quite businesslike, under the right circumstances. "Do you get a lot of high-profile clients?

"I didn't come here to talk about my job," she said, distaste plain on her face.

It was hard not to cringe at myself. I had barely spent a few minutes with her, and I was already fucking it up. "What did you come here for, then?" I asked stupidly. My heart was pounding along with the music.

"The same reason you did, sugar." She half-turned to face me, and there was that grin again, those moist and pillowy lips. I shivered as she traced a fingernail from my thigh, to my ribs, to my chest, stopping at my left nipple. She gave it a tweak. I flinched in surprise, retreating into my little corner of booth. I hadn't meant to do that. It was hard to believe she was flirting with me, that this was reality. I felt like a frightened, cornered cat.

"Sorry," Penelope said, giving me some room. Her hand lingered on my thigh. "I'm not usually this forward. You could say it's been a long week."

"No, it's fine," I spat out, desperate not to lose her. "I kind of like your confidence."

"Just kind of?" She gave a little pout and her lips glistened. I wanted to taste them badly. "I can leave you alone if you're not interested. Maybe I'm not your type."

"You're every guy's type," I blurted. Fuck, now you sound desperate. "That came out wrong. What I meant to say is, I never said I wanted you to stop."

She raised a hand to my cheek, stroking lightly with her fingertips. I had no choice but to stare into her bright hazel eyes. "You'll have to do better than that, little man."

Little man. It was insulting to hear, but from a woman as athletic and tall as her it almost came off as affectionate. I fought to keep myself still. I wanted to nuzzle against her hand, to feel more of her, any and every part of her.

"I don't want you to stop," I choked out, swallowing my pride. "Whatever you're doing. Whatever you want to do. I want it, too."

Penelope's face lit up. "Prove it." She pressed her thumb against my lips. Making a surprised sound, my mouth opened to accept it. It wasn't something I expected a girl to do, especially not in public, nightclub or not.

My cheeks warmed a little. I had spent years trying to act manly to compensate for my smaller size. It embarrassed me to let a woman take control. The nightclub was dark at least, and Robby and Liz were too busy with each other to notice what was happening across the table.

"Suck on my thumb," Penelope said. It wasn't a request. "Suck hard."

I began to suck, tasting her fingers, feeling the shape of her thumbnail as she poked the back of my tongue.

"Harder." She tugged at my left nipple and I yelped, closing my mouth tight. Her fingers flicked my nipple gently as I gave my best effort to please her. She took her time exploring my mouth as I nursed on her thumb, as if appraising its size and shape.

"Not bad, I was worried you'd be too small," she said, withdrawing her thumb from my eager mouth. For a moment, my lips chased after it. It was a strange experience. I didn't want to like it, but my cock was rock hard.

Then I felt mortified, realizing that Robby and his girl had probably seen the whole thing. But when I looked over, the two of them were gone. I wasn't sure if that was a good thing. It made me a little nervous, being alone with the amazonian pixie-lawyer.

The DJ began shouting something into the loudspeaker, but I couldn't make out his words. My focus was entirely on Penelope. Cheers filled the nightclub as all the lights turned toward the dance floor, leaving us in the shadows.

Taking the opportunity, she pressed her weight against me, lowering her hand from my aching nipple to the bulge between my legs. Her perky tits pressed against my chest, and I felt the hard nub of her nipple against mine. Looking down her cleavage, I could see the edges of her areolas, dark against her skin. I hungered to taste them.

But Penelope was in control, and I could do nothing but accept what she gave to me. I had never felt so vulnerable, trapped against the wall of the booth, smothered by a woman twice my size. Wasn't this how I should be making her feel?

"You're so submissive," she teased, tugging my trapped bulge. "Is the little man shy?"

"I'm not little," I shot back, trying to sound confident. "Maybe a bit shy, though."

"That's. Why. I. Want. You." Penelope wrapped her arms around me, pressing against my shirt with her sweaty, glittering cleavage. "I need you to trust me and do what I say. Can you do that?"

"Yeah, I think so."

"Perfect." She bopped me on the nose. "I know what's best for little sissy boys like you."

Sissy? I opened my mouth to protest. She took the opportunity to smash her big lips against mine, opening wide, forming a seal. I gasped in surprise as her tongue slipped inside my mouth. She probed deep, lapping at the roof and behind my teeth, slurping the spit from under my tongue, even tickling my tonsils until I fought the urge to gag. She tasted of expensive martinis.

I tried desperately to kiss her back, but even her mouth was powerful, and her arms were crushing me against her larger frame. I could only offer a token resistance with a few struggling flicks of my tongue. When I tried to sneak my hands under her skirt, she grabbed my wrists and pinned them against my sides.

Penelope pulled away with a long slurping sound. Our saliva spilled across the front of my shirt. "Naughty boy," she teased.

"You're one to talk," I said, breathing heavily. Looking down, I saw the mess she had made on my expensive dress shirt. "Aw, hell."

"What's the matter, sweetling?" she said, stroking and pulling my hair.

"Nothing, it's dumb. Don't worry about it."

She gave my head a playful shake. I laughed in response, though it secretly made me wonder how easy it would be for this woman to snap my neck. "Don't be shy. You can tell me anything, college boy. Just think of me as your new big sister!"

After our makeout session, that was the last thing I wanted to think of her as. But my defenses were lowered, and I found myself confessing, "Well, it's just that this is my best shirt, and I don't have the money for dry cleaning"

Penelope made an amused face.

"See, I told you it was stupid."

"You're worried about this cheap thing?" Laughing, she rested her cheek against the side of my head. It felt strange, with her hair being so short. She nibbled on my earlobe and said, "I can buy you a new shirt, college boy. I can buy you lots of shirts."

I blinked, surprised. Had I just discovered a six-foot-tall sugar mama? "Seriously?"

"Sure. If you do what I tell you and make me feel good." This time, there was no humor to Penelope's voice. She sounded deadly serious. She squeezed my balls, tugging them up and down, as if weighing my manhood in the palm of her hand. I squirmed in my seat, moaning lightly, flush with shame.

If I'm being completely honest, the woman scared the shit out of me. She was more experienced, more successful, stronger, and incredibly beautiful. She had probably hooked up with guys like this more times than she could count. Guys bigger and more confident than me. My cock was average on my best day. I wasn't very experienced. And with the way she had been teasing me, I doubted I could last long enough to please her.

Meeting with girls like this, at nightclubs? This kind of thing didn't happen to guys like me.

"Penelope, I don't know if I can do this."

She ran her wet tongue from my chin to my ear, licking deep inside. Her hot slurping made my brain tingle. She pulled away slowly, and I melted against her, moaning like a slut. "And just why not?"

"I'm just... I've never done something like this before. I'm a..."

"A virgin?" She asked, caressing my balls.

"N-no, not a virgin," I squeaked. "I've just never met a girl like you... I'm not sure I can... if we can..."

"Just. Relax," she said, planting kisses on my neck. "We don't have to fuck if you're not ready. But you are going to make me feel good tonight."

I arched my back against her fondling. The pleasure almost drove me to tears. I had a Greek goddess begging for my cock. I wanted desperately to feel like a real man. I groped her thigh, feeling braver now. God, her flesh was strong. I reached under her skirt and tugged at the lace of her panties. Slipping them aside, I could feel the emanating heat from her cunt. Fuck it. I was going to bang her. I was going to prove I was a man.

I reached to fondle her sweet hole and found... something hard, huge, and fleshy instead.

"What the fuck?" I said, pulling my hand away.

But Penelope was faster. She snatched my wrist and held it in place.'

Even in the dark of the nightclub, there was no mistaking it. It was a cock. I was holding on to a huge fucking cock!

"You're a guy?" I said, horrified, struggling against her grip.

Penelope made an insulted face. "Calm down, sugar. There's no need to panic your pretty little head off. No, I'm not a guy. Yes, I have a cock. Can you feel how hard and happy you're making it? Feel how it throbs in your hand. Now, does that hurt?"

"No, I guess not," I said, calming down.

"Is having your hand on a dick going to kill you?"

"I don't think so."

She grinned. "Do you still think I'm sexy?"

"Unbelievably so."

"Then don't be such a prude. Live a little."

She guided my wrist up and down. There was a thin layer of slickness to the skin of her cock, like she had lotioned it before coming out. Or maybe it was the sweat from her dancing. I moved my fist up and down, feeling the girth of her shaft and all of its little veins. It took me a second to realize she wasn't holding on to my wrist anymore. I was jerking her off on my own. It felt like the natural thing to do with such a cock in my hand.

"Be honest with yourself. You've always wanted to meet a beautiful woman like me. Well, sugar, here's your chance. Who cares if I've got a little something extra?"

"I guess that makes sense."

Penelope scooted forward a little, giving me access to her full length. She bit her lip and moaned as I tentatively stroked her. My body grew hot with shame and arousal. I had never imagined myself touching a cock other than my own, but the situation was overwhelming me. As much as I hated to admit it, I wanted was see how things played out.

So I began to massage her up and down, getting a feel for her womanhood. Its size filled my hand in a way that my cock never could. Resting my head against her shoulder, I explored her length with deep strokes, from its fleshy head to the root. She felt bigger than she looked. No, more than that. I felt her stiffen further in my fist. She was freakishly huge. This was a legit fucking porn star cock.

Penelope slung an arm around my shoulder, eyes glazing over. When she spoke, her voice came soaked in pleasure.

"Boys like you just need a little encouragement. You didn't think I noticed how you were following your friend around like a lost puppy? Not a lot of guys are into girls like me, and the ones that are can be a little... weird, but when I saw you, I just knew we'd be perfect together! --Mmm, yes, deep and tight strokes-- I want to be your first. I want to make you feel amazing. Feel things that no other woman could make you feel. If you don't like it, then you don't like it. You can strut that perky ass away any time you want, and you'll never see me again. You only get this one chance. Squeeze the head of my cock if you understand."

I squeezed the head of her cock. She cooed with delight, thrusting her hips. I took the cue and began to jerk her off again.

"There's a good boy. Long pumps now. Twist your hand. I want you to memorize my shape. See how the head flares out? Imagine how that would feel inside you."

"It would never fit inside me," I whispered.

"You'd be surprised what a little lube can do."

I curled up against her, trembling, fisting her girly meatstick. "I'm not sure I would like it."

"There's only one way to find out. You're a chemist or something right? Think of the scientific method. Let's build a hypothesis and test it!"

I couldn't find the guts to remind her of my college major. This domineering dickgirl didn't give a damn about me. I was her conquest for the evening, and nothing else mattered. Was this how girls felt when Robby picked them up?

Penelope raised her middle finger to my mouth. Obediently, I opened up and sucked. Once it was good and sloppy, she snaked her hand down my back and into my waistband. The other hand unfastened my belt. Then she was sneaking down my backside and into my boxer-briefs. I felt her wet finger teasing my hole."

"And now for the important question. How much experience does my little ass virgin have?"

"I've--I've never--"

She began to pump my asshole with the tip of her middle finger. "Never what, sugar?"

"Never put... anything in..." My back arched reflexively. It felt strange to have something in my ass, but not entirely unpleasant. Whenever she pulled out to tickle the opening, I felt my crotch tingle.

"Do you want me to stop? Tell me to stop and I'll get up and leave. But I promise you'll never see me again. If you want more, however..."

She buried her middle finger deeper and kissed me below the chin. I flinched involuntarily as my ass clenched around her finger.