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Chapter 29
by OppositeOfMiddle
What did we do next?
Made a sex tape
Jess walked over to her luggage again, and talked while she rummaged around. She said, “So if you’re down for it Chandler, I have a really fun idea that I think my husband will really like. So he’s never seen your dick, and I know he is super curious. He told me that if I had sex with you tonight then I needed to take a picture of your dick. But I’m thinking we can do better than that. Oh here it is.” She pulled a small video camera from her bag. “What do you think about making a sex tape for him?”
“You want to film yourself cheating on your husband,” I asked.
“It’s not cheating,” Jess said annoyed. “He wants me to do it. Like I said he gets off on it.”
Monica sits up from the bed, “Give me the camera. I’ll film. Chandler you better not be camera shy. I expect a performance of a lifetime.”
I agreed and Jess cheered. She grabbed something from her bag, then went to the bathroom.
While we waited, I asked Monica “Are you sure you’re cool with this?”
“Yeah,” she replied. “You’re not going to leave me for her. Have some fun.”
From the bathroom, we hear, “Alright y'all, get the camera going.” Monica turns the camera on a points it toward the bathroom door.
Jess steps out of the bathroom. Long transparent black stocking run up her legs. Her big red bush sprouts unconfined between her legs. The stockings attached to a black lacy garter belt at her narrow waist. Above her garter belt she wore a black corset, snitching in her already thin waist, giving her the semblance of curves. Her small tits were free, the bottoms cupped by the corset. Her small white pink nipples centered her boob. Her long waves of red hair draped her pale shoulders.
I forgot about my girlfriend sitting with a camera right next to me. I stood up and said, “Holy fuck Jess! Get over here.”
She sexily strutted over to me. I wrapped an arm around her back and brought her in for a kiss. A much different flavor of kids than Monica’s: the lips not as soft, but her tongue was much more active.
She broke the kiss and said more loudly than normal, “I’m missed your kiss, Chandler. But you know what I’ve missed more?” She slowly dropped down, her hands flowing down my torso to unbutton my pants. She unzipped me, and I helped slide my pants down until my half hard cock flopped out.
Jess took it in her hand, and still keeping her awkwardly loud volume said, “Oh my god, I always forgot how fat of cock you have.” She lifted it up it up to her mouth. She paused while Monica moved closer to get a close up.
As she was sucking, I moaned and said, “Do you like fat cocks?”
Between sucks, Jess answered, “Only on special occasions. My little pussy couldn’t handle you all the time. It’s a nice treat to get stretched out sometimes.”
She went all out giving me head. This was the first time she had really done it. While she was doing it, I couldn’t stop comparing her to Monica. I honestly loved the view: my hand combed through her red hair as she looked up at me with her blue eyes. It was something I had dreamed about. Fantasized about. Jerked off to. But the feeling was subpar to what Monica gave. The passion wasn’t there. It was just an act.
Jess stopped blowing me and stood up. She walked over to the bed and flopped down on her back. I was thinking of calling it off right then, but Monica came over and whispered in my ear, “You look so fucking hot babe. I want you to break this skinny bitch in half for me.”
The passion wasn’t in it for Jess but I wanted to perform for Monica. I kissed her and she handed me a condom. I put it on and then walked over to the bed. I grabbed each of Jess’s legs and pulled her hips to the edge of the bed. Monica moved close to get the shot of me inserting my cock into her red hair covered pussy.
Jess moaned, “Oh my god. You’re so big. Mmm. Give it to me.” I didn’t care much for her overacting. I didn’t take it slow and gentle. I turned it up immediately. It couldn’t have felt pleasant for Jess. I was pounding into her so hard: her legs spread wide and up so I was getting all the way in. But she moaned and screamed, I don’t think she was acting. She really liked it hard and rough.
After a while I flipped her over on her stomach, we were going to repeat the position of our after wedding sex. I fucked her bent over while fingering her ass. She fucking loved it. Between moans she said, “Go ugh to my bag ugggh lube oh fuck me. Get the lube.”
Monica handed me the camera. I aimed it at my cock thrusting in and out of Jess. Monica threw clothes out of Jess’s luggage until she found a small bottle of lube. She yelled, “I found it!”
Jess moaned, “I want you to fuck me in the ass. I want you to be my first.”
Monica squirted some on my cock and then onto Jess’s asshole. I handed her back the camera, and rubbed it down my dick and then easily slid my finger deep into her Jess’s ass. I assumed she was good to go.
I pressed my tip against her asshole and then pushed it in. My action was immediately met with yelling from Jess. “OhMyGOD. Oh fuck. Oh fuck. FUCK! FUCK! FUCK! StopStopStop. No more. It hurts. I can’t take it.”
I pulled out, and stepped back. Jess rolled over, tears coming down. She said, “I’m sorry. I can’t do it. It’s too big and hurts.”
I peeled off the condom. My lubed up hand started jacking my hard cock. The camera pointed at my cock, and my cock aimed at Jess’s tear streaked face. I stroked vigorously and spurted ropes of cum at Jess’s face. She quickly closed her eyes and white blobs splattered her. I moaned as I jerked the last of it out onto her. I looked over at Monica who had the camera pointed at Jess.
Monica clicked the camera viewer closed. She said, “I think that’s a wrap. Get dressed babe, so we can head home.” She handed a still crying Jess a towel and said, “Clean yourself off. And just so you know, as long as I’m with Chandler, your little sex pact is over.”
We left the hotel room, and walked down the hall, Monica’s head tucked in the nook of my shoulder. She said, “I love you. But please tell me you don’t have anymore pacts with skinny bitches.”
What's next?
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Campfire Tales
The fire isn’t the only thing getting them warm
Three married couples drink around a fire and swap sexual stories and partners
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Updated on Jun 22, 2025
by OppositeOfMiddle
Created on Jan 22, 2023
by OppositeOfMiddle
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