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When you're a twenty-one-year-old virgin, dreaming of the day you'll finally feel pussy, sometimes your fantasies get the better of you. Such was the case when I took a job at Racks and Ribs, a local "sports bar" that was known for only one thing. Hot girls.
Plenty of college babes worked the floor, and sure, they were hot. I'd never stand a chance with any of them, of course. I was in the back, sweating over greasy burgers and fries. They were up front, showing off their goods for tips.
It wasn't just college girls who worked the place, though. There was the Latina MILF, Lisa, who, in my opinion, blew the younger girls away. Then again, I'd always had a thing for older women. Not that it meant I had an ice cube's chance in hell of getting with her, but it didn't stop me from going home and beating my little dick to her nightly.
While I had a crush on her, it was ultimately Brian who would be the one taking my crush home and getting the benefit of her experience mouth and pussy. Because Brian was everything I wasn't.
He was a bartender, smooth, handsome, and had an easy time talking to women. Flirting came naturally to him. Lisa had heard it all before. She wasn't phased by Brian's pickup lines. That didn't mean she wasn't interested; just that she didn't care about what he had to say.
Lisa was what I've now come to recognize as a "cougar". She loved younger men, especially the ones with big dicks. Me? At first, I was pretty sure she didn't know I existed. I was wrong.
See, Lisa had pegged me for what I didn't know I was at the time. A simp. A cuck. A little-dicked beta male who was useful sexually, just not for the actual sex. No. That was for guys like Brian.
My descent into become her pussy-sucking servant began one night at work, after a trip to the restroom. Lisa was outside the door, like she'd been waiting for me. She pressed her body close to me and pushed something into my hand, saying, "You'll want these to use later."
Then she walked away, leaving me sweating and stunned. When I opened my hand, my little dick stiffened. I was holding her panties. I didn't know what to do, so I hid them in my pocket and went back to work. Flustered, I made mistakes the rest of the night.
I was in a hurry to jerk off that night, thinking about Lisa's hot ass, about her sucking on my cock, as I rubbed one out with her panties around it. A real woman had given me her panties. I'd never cum so hard as I did that night.
Lisa cornered me with a knowing smile the next night at work, asking, "Did you like your present?"
I was tongue-tied, but I nodded as I looked at her tits.
"How would you like to come by my place tonight and rub my feet?" she asked, trailing her finger down my chest.
Rub her feet? Like put my actual hands on an actual woman? A hot woman? I couldn't believe it.
"I just love having my sexy, oily feet rubbed. It makes me so hot," she whispered, her breath in my ear.
My cock was so hard.
"Yeah," I whispered back.
"I'll text you the address. What's your number?" she asked.
I rambled it off, stammering the whole time. I caught Lisa glancing at me, giving me little smiles throughout the night. However, it wasn't just me that had her attention. It was Brian.
She laughed at his jokes and touched his arm. I admit, I felt a little smug. Brad hadn't jerked off with her panties. He wasn't going to rub her feet for her tonight.
However, that smugness was not to last. After closing, I went out back to take out the trash. That was when I passed by an open door on my way out. It was dark, but by the light of the hallway, I saw her and Brian.
She was on her knees, in front of him, sucking his cock. I was stunned. At work? She moaned and whimpered with her lips around his prick, while Brian had his hand on her head.
"You like that big cock in your sexy MILF mouth?" he whispered.
She moaned around it. I stumbled back, out of sight, as quietly as I could. I stayed out in the night for several minutes, distressed but with an unexpected hard-on. I couldn't get the image of her sexy lips stretched around his cock out of my mind.
By the time I got back in, they were gone. Lisa caught me outside in the parking lot, though. Brian was already gone.
She pressed her body against me and said, "What's wrong, baby? You look upset."
Baby? The word melted me. Had I imagined what I'd seen.
"Nothing," I said.
Of course, I didn't want to pass up on the chance to rub her feet. I should have known better, though. An experience woman like her would see through my bullshit.
"Oh, baby," she whispered in my ear as she put her hand on my cock. "Did you see something tonight in the back?"
I shuddered as I remembered the sight of Brian's cock in her mouth.
"Did you see me sucking on Brian's big cock?" she whispered.
My little dick jerked under her hand and I nodded.
"It doesn't mean anything, honey," she said. "I just love dominant men with big cocks. Why don't you come over and rub my feet and we can talk about it?"
"It doesn't mean anything, honey," she said. "I just love dominant men with big cocks. Why don't you come over and rub my feet and we can talk about it?"
"Yeah. Okay," I mumbled.
"Good boy," Lisa said. "Just follow me over. I can't wait to get those little hands of yours on my feet."
Burning with inner shame, I followed her to her home. It was a simple, clean place, but I was shaking with nervous anxiety. A hot woman had invited me over. I had no idea what to do.
"I'll be right back, baby," Lisa said and disappeared into her room.
When she came back, she wore a sexy black dress that was short and showed off her incredible legs. She sat on a cute bench and beckoned for me to kneel. I did, getting on my knees in front of her.
She gave me a bottle of oil as she parted her legs, flashing me a pair of sexy purple panties. I couldn't believe it. A real woman was spreading her legs for me. I could see her panties.
"Go ahead, baby," she said, putting her foot in my hand. "Rub my sexy feet for me."
I did it, oiling up my hands and rubbing her feet. They were so soft and beautiful.
"Did you like what you saw tonight?" she asked as I rubbed her feet. "Did you get hard watching me get down on my knees for Brian and suck his big cock?"
I blushed deeply but didn't answer.
"It's okay," she said. "I know it's hard for you to admit it. You're a virgin, right?"
I wanted to deny it, but just looking up at her I knew I couldn't.
"Yeah," I said.
"That's alright, baby," she said. "We aren't going to have sex. You know that, right?"
I did know. I just hadn't wanted to admit it.
"It doesn't mean you won't get to see my pussy," she said. "Even lick it for me. Would you like that?"
I looked at her pussy, covered by the panties and I nodded.
"I only let hot guys with big dicks fuck me," she said. "But virgins with little dicks? I let them eat my cunt. It's the best you can hope for. You'll learn that as you get older. Girls like to fuck real men with big cocks. Is that you?"
It wasn't. I shook my head.
"This is making your little dick hard, isn't it?" she asked.
I looked at her feet and nodded. I didn't understand why I had a hard-on over it. She was insulting me, telling me I had a small dick, that I'd never get laid. Yet here I was, rubbing her feet, on the verge of begging her to let me lick her pussy.
"Go ahead and clean my feet," she said at last.
I toweled them off. She beckoned me to follow her to her room, where she lay back on the bed and took off her panties. I stood there like a stump, staring at her shaved pussy, the first I'd ever seen.
"Come here and lick it," she said. "I want it nice and wet when Brian gets here."
"Brian?" I squeaked.
"I told you. I fuck guys with big cocks. You can get me ready for it."
Not wanting to miss my chance at actually touching a real pussy, I did it. I crawled between her legs and I pushed out my tongue. The taste of her was amazing. I couldn't believe I was licking a real woman.
"You want to keep doing this, right?" she asked as she put her hand on my head and pressed it into her cunt.
I groaned.
"When Brian gets here, I want you to sit and watch, okay? Don't say anything. Just lick my cunt. I know you're going to."
She was right, of course. I'd never feel her mouth or pussy for myself. But I could be in the same room with her, watching her pleasure Brian's big cock.
When the doorbell rang, she ordered me to stand in the corner while she answered it. She returned with Brian, who spotted me standing there and laughed.
"Oh, shit! For real? I didn't think he was such a little simp," Brian said.
"He's very sweet," Lisa said. "He can't help that he's a little-dicked virgin. Come over here and let him watch me suck your cock."
Brian chuckled, saying, "What a perv. He's just gonna stand here with his little boner in his hand and watch us?"
"He needs to learn," Lisa said. "He's going to be a life-long virgin, licking cunt while men with big dicks get the pussy. He may as well start now."
I didn't want to think she was right, but somehow, I knew she was. Brian chuckled, said, "What a cuck," and pushed Lisa on her knees. She pulled out his cock, moaning as she put her lips around it.
I stood there in the corner, watching this woman I had a crush on suck the dick of our coworker, and my heart was racing with excitement. I fondled my little dick through my pants as Lisa glanced over at me, her mouth full of Brian's bigger prick.
She looked so sexy, her plump lips wet and shiny as she moaned and pleasured Brian. I tried to imaging what that would feel like, but I couldn't. All I had to compare it to was jerking off.
Of course, it didn't end there. I watched Brian fuck her, while she looked at me, grunting and moaning.
"That big dick feels so good, baby," she said. "I love Brian's fat cock."
Brian mostly pretended I wasn't there as he railed my crush, though he couldn't help but laugh.
On his way out, he slapped me on the shoulder and said, "Have fun cleaning up, simp."
Cleaning up? I didn't understand.
"Come here," Lisa called, laying back on the bed.
She was coated in sweat, naked, her big tits heaving. There was cum all over her pussy mound, and inside of her. Brian's cum.
"I need your tongue in my pussy again, baby," she said sweetly.
"In your..."
"Go on. You want to lick my pussy, right?"
I looked at the streaks of jizz, leftover by the cocky bartender who had just fucked my MILF crush. I did want to lick her pussy. But did I want to do it like this?
"This is your last chance, honey," she said. "Or you can go. But if you do this, you're going to keep doing it. Do you understand?"
"I... don't know," I said. "Are we... you know... ever going to do it?"
Lisa shook her head. "I only fuck real men with big cocks. We'll never do it. You'll just lick my cunt. Sometimes, I might let you jerk off on me if you're good."
"Can I..." I started.
"Not tonight," she interrupted. "You have to earn that. You can start by licking my pussy right now."
I looked at her jizz-coated pussy again. I soaked in her naked body, her big tits, and I imagined getting to jerk off on them; on a real woman. Then, I knelt, and I began to lick.
"Good boy," she said. "That's my little-dicked virgin. You're a good boy."
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