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My GF's Cruel Little Arrangement [Part 6]

· 5 min read

So on Tuesdays and Thursday’s, Becca had to hold up her end of the deal and take care of John. After each session, she would fill me in on the details. Here’s basically how it went down:

The first time Becca went over, she could tell John was pretty nervous. Despite being 5’1” and like 100 pounds soaking wet, Becca intimidated the fuck out of him. She had brought some weed brownies to help everyone calm down and get into the right headspace for what was about to go down.

She said they hung out and just chit chatted for about an hour when she felt the brownie start to hit. At this point, she became a bit more forward, bluntly suggesting that they head to the bedroom and get started. John and Emma sheepishly walked into the bedroom, and John sat down onto the bed. She said he was being pretty awkward.

“Sooooo…” he started out.

Becca calmly instructed him, “Take off your pants.”

He did, and she helped pull them down to his ankles. She knelt down and gestured for Emma to join her. Emma was kind of passive, just watching and waiting for guidance on what to do next.

Becca yanked down is underwear, and his semi-hard cock flopped out. She took it in her hands and started fondling it, tossing it back and forth between each hand. The brownie must’ve helped, because it slowly started to get harder, until it was fully erect at just over 4 inches.

“This isn’t going to work,” Becca bluntly declared.

“What?! This was the deal! It’s hard, and Emma got what she needed!” John protested.

“I understand that. Emma did get what she needed, but what do you need?”

“…a fuck?” John suggested with confusion.

“No, that’s just not going to work. Like it won’t work logistically,,“ she explained. “Emma and I have both been taking a cock twice this size. We’re not going to feel anything. You’re not going to feel anything. The deal was to fulfill your needs, and we’ll just have to find an alternative method to fulfill them.”

John seemed pretty defeated, “…and how do you suggest we do that?” He asked, exasperated.

“Lay back. Lift your legs behind your head,” Becca instructed.

After a moment of hesitation, he did as he was told. Becca then reached into her bag and pulled out a latex glove and some lube.

“Relax,” she told him “Relax your entire body and quiet your mind.”

She put on the glove and applied some lube to the tip of her middle finger and down her pinky finger. She then told Emma to hold John’s legs as she started swirling the tip of her middle finger around John’s bare asshole.

John quickly sat up and exclaimed, “What the fuck?!”

“What?” Becca gave him a puzzled look.

“What are you doing?!” He asked incredulously.

“I’m going to finger your asshole,” She responded nonchalantly. “I told you to relax, now lay down and spread. It’s going to feel good, I promise. Trust me, you’ll be grateful afterwards.” She then gently pressed on his chest, pushing him back down onto the bed.

He quickly sat up again, though, exclaiming, “I’m not gay!”

Becca paused and just looked up at him. She stared at him for several seconds with a look I know all too well. It’s a dumbfounded expression that pretty much says, “Are you a fucking idiot?” She held this look, then started questioning him, “You’re here with two hot girls who are about to treat you to an orgasm. What exactly is gay about that?”

Emma spoke for the first time, about to stick up for her boyfriend, “Becca…”

“Becca what? How else do we satisfy him? We’ve already come to the conclusion that we can’t fuck him. He won’t last long enough if we blow him. Prostate orgasms are all the rage. He’ll cum hard. It’s not gay, and plenty of men do it.”

“Does your boyfriend do it?” John probed.

Becca paused for a moment. Then she looked him directly in the eye and confidently answered, “Yes.” (Nope lmao).

John wasn’t convinced.

“I’m dead serious,” she continued. “He even does more than a finger. Sometimes we use toys.” (No the fuck I don’t lol).

John was curious.

“True alphas aren’t insecure in their masculinity. We do this all the time.” (Never lmfao).

John then countered her statements by asking, “Does he do it during your time with Emma?”

Becca quickly interjected before Emma could respond, “No. That’s about her pleasure. We do it during our private time. And likewise, these sessions are about your pleasure. Just relax and let us pleasure you. It’s what we do best.”

Emma clearly wasn’t keen on the idea. She didn’t really like the thought of her boyfriend taking it up the ass, but Becca relayed to me that she also didn’t object.

With this, John cautiously laid back down and spread his legs. Emma held his legs again, and Becca got back to work by gently working his asshole. She covered it in lube and started to gingerly slide her pinky in. She continued with her verbal instructions to relax and breathe. She was very delicate and deliberate in her movements trying to help John totally relax and accept her finger.

Over the next few weeks, Emma, John, and Becca continued with these sessions. Eventually, she started using her ring finger. Then her middle finger. Eventually, he could comfortably take two fingers with some speed. Despite this, he never came directly from anal stimulation. She or Emma always finished him off with a handjob, though he noted that those orgasms were more powerful than a normal handjob.

After around 7-8 weeks, Becca ran out of fingers to use. One day, she came to the session and brought a toy with her. She revealed a small, 4 inch by 3 inch, purple, very realistic penis-shaped dildo.

Surprisingly, it was Emma who protested the most. She really didn’t like how realistic it appeared, veiny and with a bulbous head.

“It’s not real,” Becca expressed. “It’s just a toy.”

“Still..” Emma couldn’t really express why, but it was pretty clear she didn’t like it. She looked towards John with concern and hope that he would protest, but Becca told me that he was too horny to care and more interested in the soon-to-come orgasm.

“It’s just a toy,” Becca gently reassured. “It’s just a tool to stimulate some nerves. Nothing more.”

Although still uneasy, Emma started to relax again. Before she could change her mind, Becca quickly lubed it up and inserted it into John’s asshole. John let out a soft groan of pleasure, and Becca relayed to me that it looked like Emma’s heart had dropped into her stomach when she heard it.

Over the next few weeks, I noticed a surge in our expenses. I checked out Becca’s credit card statement, and I saw that she had spent like $700 dollars at adult toy stores. John had been graduating to bigger and bigger cocks, and she had to keep buying more dildos. We had a talk, and I explained that while I was thrilled that she was getting the release she needed, that we needed to try to curb the spending. She agreed with me, but she asked for permission to buy just one more. She said she would need my help with it. I asked how could I help, and she said she’d show me in a minute. She went online and bought the toy, then came back and showed me the email receipt on her phone.

She had bough a cock mold. Basically, this company sends you this tube that you place your cock into, and then you send it back to the company, and they make an exact replica of your cock.

She was beaming at me with utter pride in her eyes as she eagerly told me, “I need you to fill this.”