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Chapter 18 by OppositeOfMiddle OppositeOfMiddle

When did I see Jess next?

Two years later

The next time I saw Jess, we were all living out in Colorado: Ross, Joey and me. Jess and I had kept up through texts. We would flirt a little but nothing crazy.

She was traveling through Colorado with her new boyfriend. She had thankfully dumped Brent after all of that. She contacted me and asked if I was available for dinner. So I had dinner with her and the guy she was dating. It was a little awkward but not too much. Jess and I definitely carried most of the conversation. We said goodbye and hugged.

I went back to my place, and then were going to continue their trip into the mountains. Well there was some pretty bad weather that night. I got a call from her asking if they could crash at our place because they couldn’t get to their hotel. I said yes, telling them we had an air mattress we could set up in the living room.

Both Ross and Joey were asleep so they didn’t know I allowed some guests to sleep in our house. I got them set up in the living room, and they thanked me. I went back to my room to go to bed for the night.

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Just as I’m about to fall asleep, I saw my door crack open and heard a voice whisper, “Chandler?”

I whisper back, “Yes?”

I watch Jess’s skinny body slide through the small opening she made in the door. She was wearing a T-shirt and shorts. In the darkness I could make out the silhouette of her long legs. She tiptoes over and crawls into bed with me.

I asked, “Where’s your boyfriend?”

“He’s sleeping,” she said. “So we have to make this quick and quiet.” I feel her hands rubbing along the skin of my torso making their way down my body.

I said, “Then we’ll have to speed things up.” I flip the position of my head and feet. She understood what I was going for, because she immediately pulled down my shorts. I pulled hers off her long legs and started kissing her thighs. I felt Jess suck my soft cock into her mouth, but it was hardening quickly.

Until last time when Jess was waxed smooth, she now had a tangle of red pubic hair I had to get through to reveal her pussy. I licked and her pussy had an acidity taste to it. I kept at it though. Soon she moaned with my hard cock in her mouth. Her pussy was wet and I fucked her with two fingers.

Once we were down 69’ing. I grabbed a condom from my dresser. Jess laid seductively on my bed. She was pale all over. The only darkness on her body was her pubic hair, and brown nipples. She was still skinny but she had filled out a little bit over the last two years. Her breasts were fuller. She looked incredible and I couldn’t believe I was so lucky. She whispered, “How do you want me?”

“I’m on top this time.” I positioned myself between her long legs. She moaned as I rubbed my cock between her pussy lips and then penetrated her.

She pulled me down to whisper in her ear as I fucked her. “God I love your big cock. My boyfriend’s is so tiny. It’s like getting fucked by a thumb. Awww. But not you. You’re a big man.” I gave her long slow deep thrusts. “Oh Chandler. Give it to me. Fuck me like you missed me. I know you did.”

I straightened up. She could no longer talk dirty in my ear, but now I could adjust her legs. I spread them out wide and held them. The sight was incredible. I watched my thick cock moving in and out of her thin body.

Then I put her legs up on my shoulders and really started to give it to her. I probably wasn’t as quiet as I should have been. My hips made smacking sounds against her thighs and ass, everytime I thrusted in.

Jess squealed in orgasm and had to grab a pillow to cover the sound. I came inside her still wearing the condom. Laying next to her I asked, “How is this only the second time we’ve fucked?”

As Jess put her clothes back on, she said, “We’ll have to find ways to do it more often.” She gave me a kiss then went back out to sleep with her boyfriend in the living room.

When did we see each other next?

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