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My GF's Cruel Little Arrangement [Part 9]

· 4 min read

So it’s John’s turn to get his needs fulfilled. I wasn’t really sure what to expect, was Becca just going to give him a handjob? Finger his asshole? I had no idea.

Becca actually then suggested a quick break to recover. She grabbed some waters, Gatorade, and some snacks for each of us. She helped Emma recuperate and gave me some strength back. John was still shell-shocked, but Becca gave him some Gatorade and told him to drink up and get ready.

Eventually, it was go time. Emma had regained her composure well enough to sit up and start to watch. Becca went back to our room and came out with lube and latex gloves.

She then instructed John to get in a table position on all fours while putting on the gloves. He did so, and Emma watched with disgust as Becca lubed up her fingers and inserted them into John’s asshole. John let out a muffled groan and dropped his head to concentrate on the sensations.

John, almost out of breath, asked, “do.. you.. have.. any.. toys…..?”

Emma shook her head.

“Yes, of course!” Becca proclaimed, popping up and running into our room.

She quickly came back out looking disappointed, “Actually, we don’t have any toys here :( I think I left my bag at your place.”

She then put resumed fingering John’s asshole. It was actually pretty fascinating to watch. He was really moaning and pushing his hips back into her fingers, and he really seemed to enjoy it.

Becca then asked John, “Would a toy feel better?”

Emma quietly interjected, “No.”

But John contradicted her with an enthusiastic, “Yes!”

Becca then announced, “Okay, I actually think we might have one toy here.”

She then put some lube in her free hand and started rubbing it around my cock, getting me hard again.

Seeing this, Emma’s eyes looked like they were going to burst out of her head. A fire rose within her, and she shouted out “NO!”

John oblivious to what was happening behind him, exclaimed “What?!”

“These are about his needs,” Becca started, ignoring him. “He’s going to cum hard. I guarantee it. It’ll happen in less than 5 minutes.”

Emma rejected Becca’s prophecy, “No he won’t!”

Becca challenged Emma, “Let’s make it a bet,” as she tugged on my cock, guiding me into position behind John, ready to mount him.

Becca got me hard and lubed up, and John was horny as fuck, really throwing his hips back into Becca’s fingers. Becca gave me a passionate kiss, looked deep into my eyes, and whispered to me, “I love you so much.”

Becca then took her fingers out of John’s asshole and walked over to Emma, guiding her to sit at eye-level in front of John, similar to the first night I fucked Emma doggy style. She was positioned at eye level with him so that she could stare deep into his eyes and see every reaction and expression.

Emma’s face was one of pure disbelief and concern. She really did not want John to enjoy this. She really hoped he wouldn’t find it pleasurable and that he would stop it soon.

Fully lubed up, I pressed the tip of my cock onto John’s asshole, grabbed his hips with both hands, and started to push myself into him.

Becca said once I put my hands on his waist, he immediately realized what was happening, and his eyes went wide with fear. He had taken a dildo replica of my cock before, but he had never taken the real thing.

I think back to what Becca said our very first night together with John and Emma, “‘other things’ aren’t the same as real cock.” That statement rings so true. John felt the width and pressure of my thick cock and started to flail, trying to crawl away, but I Becca held him in place while I entered him. Once I has halfway in, his body relaxed and he let out a long groan of pleasure. Emma knew she had lost at that point.

John then continued to relax and actually started pushing his hips back into my cock, and I quickly bottomed out inside him. He was gripping Emma’s hands extremely tightly when I started to pick up my pace and truly fuck him. I started off slow, but as I increased my pace and clapped his little cheeks, his grunts turned into squeals. Squeals of pure delight. Becca was timing with her stop watch, and just after the three minute mark, Emma saw John’s whole body start to tense up. After a few moments and some really loud grunts, his entire body began to shudder, and I felt his asshole start contracting even tighter than Emma’s pussy. Emma’s face was one of pure disappointment as her ‘man’ lost himself on a fucking cock. She just stared at John in disbelief. He tried to be romantic and say “I love you” as he was cumming, but she just watched him, mouth agape in disappointment.

I was so engulfed in the scene in front of me that I didn’t even notice Becca until I heard her roar in the chair off to the side. She was cumming extremely hard watching this play out while using the vibrator on the high setting on her clit.

John’s asshole was really tight, and this whole environment was erotic as fuck, and I was really close to cumming. I looked to Becca for her direction as I always do, but she was completely out of commission after her last orgasm. Given this, I made the executive decision to pull John’s hips hard into my cock and unload the spare change from my balls into his little boy-pussy. This orgasm wasn’t as strong as the first one with Emma, it almost felt dry, but it still felt really fucking good.

I pulled out and some of my hot cum dripped from John’s swollen asshole onto his leg, and he groaned as he collapsed into Emma’s arms. Now it was Emma who’s face had gone completely white as if she had seen a ghost. John cuddled up with a shell-shocked Emma, and I carried Becca onto the sofa to snuggle up with me. We all laid there for around one to two hours, some of us passed out, but around 4am Emma shook John and told him to get up.

Becca was still passed out, but I offered them a shower, some water, food, or anything else they needed to clean up or recuperate, but Emma denied it all. She told John to get dressed and then they both said goodbye and left. I filled in Becca on their departure the next morning after we woke up and fucked, and that was that.