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This past summer I took a trip to Chicago with a few girlfriends. It was fun and I enjoyed it. The whole reason we went on the trup was so I could get my mind off of things for a few days. I had been feeling down after a resent break-up and wasn't really acting like myself. So that's when we decided to take a trip.

After finally getting there, we checked into the hotel and got settled in our room. I was exhausted from driving so I took a nap while the two other girls, Caitlin and Amber, left to check out the pool. I slept for a good four hours. It was dinner time when I woke up, so I found the girls and we headed to a restaurant.

Dinner was the best part of the night. While eating a group of three gents came up to us and asked to sit with us. We agreed. Amber was mostly talking to Adam, while Caitlin was flirting with Chris. I was still pretty down about my break-up, but The other Man, Jon made me feel so much better. While discussing our previous relationships I felt a smooth hand go up my leg. My eyes got wide with fear and confusion. I didn't move.

Jon's hand moved back down towards my knee, then he removed his hand from my leg. I relaxed and glanced over to the others. Still flirting with one another. I looked at Jon, he had the face of disappointment on him.

"Come with me." He said.
"Uh, alright" I gracefully said standing up."Where are we going Jon?"
"Some place more quiet."


I was a little nervous as to what was about to happen next, but I remained calm and tried to act like I was fine. We left the restaurant and headed to the streets.

"You are very beautiful you know that right?"
"Thank you, that is very kind of you." I said, feeling really good about myself for the first time in a long time. "So, where are we going exactly?"
"It's a surprise." Jon replied insidiously

He wrapped his arm around me keeping me warm. We arrived at a building where he walked me inside and showed me to a room. He brought me to his apartment. I wasn't sure what to do so I played it by ear.

"Sit." He commanded with a gentle tone.
"OK.."


He came up behind me and slid my coat off me. Then as he rubbed my shoulders I felt his ips against my neck. I moaned softly.


"I see you like that." He whispered softly in my ear.
"Mmhmmm...."


He turned me around, placing both hands on my face tilting my head back. He kissed me. His lips were warm against mine. I felt his tongue tasting the inside of my mouth. He stopped looked at me and moved his hands to my sides and lifted my shirt off. Doing the same to him he unbuckled his pants.


"Well, aren't you going to take yours off too?" He asked
"Yeah, I was just admiring your cock."
"Oh, well let me return the favor." He said.


He ripped my pants off, and unhooked my bra. Staring at my breasts he grabbed them sucking them hard. I pressed his face into my chest. He took my hand and helped me to remove me panties.

"You still are beautiful." He said.


Smiling he lead me to his bedroom. I got on the bed lying on my back.

"No no, turn over."


I flopped over onto my stomach. He rubbed both hands from my neck to my ass. He stopped to rub my bottom. His hands felt so good on my skin.

"Alright, now you can turn over."


I flipped over onto my back again. Running his finger down my chest and stomach he kissed my bald pussy. By this time I was already wet and he was making me even more wet.

"Mmmm you taste amazing." He moaned


He entered a finger into my hole. I arched my back in pleasure as he finger fucked me. I couldn't help but scream in delight.
I had never been fingered this well before.

"YES! YES! YES! OH GOD YES!" I screamed.
"You like that do you?"
Yes, yes, yes Jon I do!"


He fingered me faster and harder rubbing my clit with his other hand. He pulled his finger out and traced my nipples with it. His cock was hard as a rock. I noticed how big it was now. I stood up and pushed him onto the bed. I grabbed his erection in my hand and sucked him.
"Shit, Debbie...That's good"


I sucked him for a good 15 minutes before mounting myself ontop of him. My pussy was tight from not having a good fuck lately, but that only seemed to make Jon want me more. Has I fucked him he grabbed my hips pushing me down making sure I took in all of his meat.

"Oh, fuck me Baby!" He cried


He turned me around and spread my legs apart and fucked me. I was breathing hard and was shaking. I wrapped both legs around his back to help support each pounding thrust he gave me. He fucked me until I could no longer breath. He finally came inside me. Feeling the warm liquid fill me up made me come once more. He collapsed on me panting hard. We both fell asleep together.

I had only been asleep for an hour when my phone was ringing. It was Amber.

"Where are you? We are worried sick. We don't know where you're at!" Amber yelled.
"I'm fine I'm staying somewhere else tonight." I whispered trying not to wake Jon up.
"Who are you talking to, Debbie?" Jon said half asleep.
"Who is that in the background?" Amber barked.
"No one Amber I have to go, I'll call you later." I said hanging up.
"Are you going to answer me now?" Jon said.
"I was talking to Amber."
"Oh, ok...well come back to bed."

I moved back in bed next to him. I felt his had sliding down towards my pussy again. He rubbed my clit. I started bucking, I wanted to fuck again and so did he.

"I think it's time for round two." He said as he started to enter his throbbing cock in me again...

(Comment if you want to hear part 2 of "Chicago love")

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