My Windy City Adventure

I met Penny and Josh at a hotel bar in Chicago. They were in town for a wedding and I was there on business. Penny was a cute 23 year old redhead with a nice thick curvy body. Josh was a typical 25 year old college grad with an athletic build and a beat up Sox hat on backward.

We started out talking baseball but eventually segued into a more personal conversation. Josh and Penny had dated off and on for a few years but they were mostly friends with benefits.

Two hours and several drinks later Penny was openly flirting with me in a conversation that was thick with double entondre and innuendo.

"Do you want to come upstairs and help Josh satisfy me," she whispered in my ear as she finally dropped the pretense of being coy and discrete.

A surge of blood flowed to my cock as she grazed her fingernails across the crotch of my jeans. "Yes," I answered excitedly. I had never experienced a threesome and while I would have preferred of the two girl variety the opportunity to fuck a hot redhead ten years my junior was something I was not going to pass up.

We paid our tab and quickly left the bar together. Penny pressed her soft curvy body against mine and kissed me deeply as the elevator doors closed.

"I can't wait to feel your cock inside me," she panted between kisses.

Josh stood close to Penny and ran his hands over her body as we kissed. Their movements were well choreographed and I got the feeling that it was not the first time they had picked up someone for a threesome.

We stumbled into their room. Penny and I tore at each others clothes as Josh pealed his clothes off beside us. When we were all naked Penny lay back on the bed and pulled me down beside her. Josh lay on the other side of her and caressed her body as I did the same.

I looked at her sexy alabaster body and my eyes widened as I caught a glimpse of Josh's cock. It was enormous.

Penny saw the look on my face and giggled. "It's impressive isn't it."?

"Uh, yeah," I stammered. His cock was easily 8 plus inches long and proportionately thick.

"Why do you think I keep him as a friend with benefits," she teased. "Touch it." Penny took my hand and placed it on Josh's monster cock. It was warm with soft almost silky skin and it throbbed in my hand.

"Wow," I said softly as I held another man's dick for the first time in my life.

Penny's hand moved mine up and down Josh's turgid shaft. "It feels good doesn't it," she whispered in my ear as she kissed and licked my neck and earlobe. Her hand wrapped around my cock and she squeezed it hard making me groan.

I kissed Penny deeply as she continued to move my hand over Josh's giant dick. She moved her hands to my head and pushed me down her soft curvy body as my hand continued to stroke his cock.

I licked and sucked her big beautiful tits and Penny moaned softly as her hands continued to caress my head. She pushed me down her body and I left soft butterfly kisses down her flat stomach to her shaved pussy.

I climbed between Penny's splayed thighs and inhaled the sweet smell of her arousal. I parted her glistening wet pussy lips and lowered my face to them. My tongue flicked out and I tasted her juices as I licked and sucked her thick meaty lips into my mouth.

Penny and Josh embraced and kissed as I licked her delicious pussy. He ground his hips against hers as they kissed and his enormous cock left a trail of precum on my cheek as I continued to eat Penny's pussy. Without thinking my hand grabbed his cock and I began stroking it again while I flicked my tongue over her engorged clit.

Penny's hands held my face tightly against her wet pussy. "Yes," she hissed. "Right there baby," she panted, "I'm gonna cum. "She cried out as her body shook from her climax.

My hand continued to stroke Josh's big dick as Penny came. She pushed my head away from her hypersensitive clit. She sat up as Josh rolled onto his back. I expected Penny to mount his giant rod but what she did took me completely by surprise. Her hands guided my head to Josh's lap. She pushed my mouth forward until the head of his cock rubbed against my lips.

"Suck it," she said breathlessly. I looked into her pretty green eyes and saw white hot lust.

Josh smiled and held the back of my head as his cock drooled precum onto my lips. "Open wide," he said.

I can not explain why but I did. I had never entertained a conscious homosexual thought in my life but at that moment I made a conscious choice to accept his cock into my mouth. I parted my lips and tentatively licked the stream of precum from his giant cock head. It tasted salty yet sweet and I wanted more. I opened my mouth as wide as I could and took several inches of hot throbbing cock into my mouth. I felt the thick veins slide over my lips as I pressed my tongue against the underside of his shaft.

Josh pushed my head down and I felt his shaft slide deeper. My eyes watered and my throat opened as I gagged. Josh thrust his cock down my throat.

The feeling was amazing and liberating. I backed off and wrapped my hand around the saliva slickened shaft. My head bobbed over his throbbing cock as I furiously pumped the thick shaft. I could tell he was getting close to cumming and I wanted it.

"I'm gonna cum man," he grunted as the first blast of thick warm cream shot hard against the back of my throat.

I gulped down most of the first shot but it came to fast and it filled my mouth and ran down my chin onto his balls. I closed my eyes and swallowed my mouth full of man juice. It was humiliating yet delicious and I wanted more. I licked and slurped cum from his shaft and balls. I swallowed it all and then wrapped my lips around his big cock as it softened in my mouth.

Penny pushed me onto my back and mounted my cock while facing me. Her body rose and fell as my cock pistoned in and out of her delicious pussy. The contrast of her sparse red bush, her alabaster skin, her pale brown nipples, her beautiful green eyes and her fiery red hair was amazing. Her full pert tits bounced in time with her body as she rode my cock slowly like Lady Godiva on a trotting horse. She leaned forward and pressed her soft lips to mine tasting the residuals of Josh's cum. Our lips parted and our tongues entwined as I thrust my cock into her slick wet pussy hard and fast.

Penny straightened up and increased her pace. She rode my cock at a quick canter. A smile crossed her pretty face as her breathing became erratic. She crossed into a full gallop with her head thrown back as her climax approached. The pretty redhead yelped and panted as her body started to quake. Her body looked amazing as her chest heaved and her tits bounced while she rode my cock to a thunderous climax.

Penny climbed off my hard wet cock and lay beside me. She pressed her soft lips to mine and kissed me deeply as Josh took my throbbing dick in his hand. He opened his mouth wide and took my entire 6 inches down his throat. His mouth was hot and wet and his fingers were incredibly talented.

"He gives great head doesn't he," Penny asked. I could only moan my agreement.

Josh's head bobbed over my turgid rod as Penny and I kissed.

Penny kissed my neck and then my nipples as she made her way down my body to join Josh between my legs. I watched as their lips met in a kiss at the head of my cock.

Penny sucked my dick as Josh licked and sucked my balls. They switched and Penny licked my balls while Josh deep throated my cock. I felt my climax approach like a freight train.

Josh's head bobbed furiously over my hard rod as I passed the point of no return. My dick started to spurt into Josh's hot mouth. He swallowed the first blast then Penny took my erupting cock into her mouth. She held my thick creamy juice in her mouth as she made her way up my body. Penny pressed her soft lips to mine. Our lips parted and cum spilled from her mouth into mine as our tongues entwined. Our tongues played in my creamy goo, splashing drops from the corner of our mouths as we kissed deeply. I swallowed my seed as we continued to kiss.

Penny left my body and climbed between Josh's thighs. She slurped his semi hard cock until it was at full attention and the she straddled my body in a 69 position.

Josh knelt behind the sexy redhead and rubbed his big monster cock against her swollen red pussy lips. I watched as the big hunk of hard flesh split her pussy and slowly sank all the way inside her. His big shaved balls hung over my mouth and I took one into my mouth and swirled my tongue over it. He pulled back and I licked Penny's juices from his hard shaft. I pushed my tongue between her lips and his shaft and then flicked it over her hard clit making her moan loudly.

Penny panted and moaned as Josh fucked her hard as I licked her delicious pussy. Josh's big steel rod pounded harder and harder into Penny's liquid core. His balls rubbed against my face with each powerful stroke. I sucked hard on Penny's thick meaty pussy lips and flicked my tongue over her clit while Josh fucked her hard and fast until she came hard.

Penny's legs quivered and got weak as she came. Josh continued to pound her spasming pussy until he was ready to cum. He buried his 8 inch monster into her and pumped buckets of cum inside her.

We all collapsed on the bed and drifted off to sleep in a tangled mess of human flesh.

I awoke several hours later to their whispers. My cock was hard and pressed into the soft valley of Penny's ass cheeks. Penny rolled over to face me. She kissed me softly and rolled on top of me straddling my hard dick. She reached back and guided my cock into her pussy. Josh moved behind her and rubbed his well lubricated cock across my balls and the base of my cock then up over her sensitive asshole.

Penny moaned as he pressed the big head of his cock into her asshole. He kept pushing his hips forward until his big dick was buried all the way up her ass.

Josh pulled back and Penny moaned loudly. I could feel his cock rubbing my through the thin membrane that separated her two holes. We fell into a steady rhythm dictated by Josh's thrusts.

The room filled with the sounds of slapping flesh and raw guttural moans from Penny, Josh and me.

Josh increased his pace and his cock persistently rubbed the underside of my dick with each stroke. I knew I was not going to last much longer. I pulled Penny's pretty face to me and kissed her passionately as I came inside her wet warm pussy.

Josh continued to pound her gorgeous ass until he came inside her and collapsed onto the bed beside us. Once again we drifted off to sleep.

I awoke alone in bed. I could hear the shower running and voices through the wall. I debated joining them but in my sober state I thought better of it. I quickly dressed and slipped out the door before they came out.

That was my last time in Chicago and I will always remember my eye opening experience with pretty Penny and her FWB Josh.