The Double Team Ch. 02: Final Preparations

"Why would I want to go for drinks with you AND Cole?" Jenny asked, hoping that Frank would just take her for drinks again. After all, Jenny had developed a bit of a crush on Frank. With Cole, she'd been there and done that before, coming out of a relationship with him over 6 months ago. Unbeknownst to her, Frank and Cole had created "The Double Team", a joint effort between them to secure women by offering double the pleasure and double the penetration. Jenny was targeted as their first real-world conquest. Their arch-rival, Tyler Johnson and his large cock, was cleaning up with the local women. Cole and Frank were about to fight back but needed to take their training to the next level.

***One week prior to Jenny date night****

Frank and Cole had been planning, strategizing, and even practicing for their first real world attempt on Jenny. They had rehearsed and strategized on how to approach the subject with her. They also had practiced getting comfortable around each in a sexual setting. The best friends had never done anything sexual together and were very uncomfortable masturbating together for the first time (see Ch. 1 Origins story). That needed to change if they were going to conquer Jenny. A lot of porn was was watched together by both of them in the weeks that followed.

"You know bro, we've gotten comfortable masturbating together but I feel that both of us are going to get freaked out by our cocks touching if Jenny agrees to this." Cole stressed.

"I was thinking about that too. Okay, great. We're comfortable around each other but I might get squeamish once our cocks touch together." agreed Frank.

"She needs us to be 100% comfortable with this and we need to be the driver here. She's not going to be comfortable unless we are!" Cole confirmed.

"This outta be good, what do you suggest Cole?" asked Frank with a laugh. At this point, he was used to Cole suggested controversial ideas. It seemed like just yesterday that Cole had him over to masturbate to porn together. Frank was comfortable doing that now and understood that another step was needed to be taken in order for them to be successful with Jenny.

"Just throwing this out there, but why don't we try this with a hooker before doing with with Jenny?" asked Cole with a mischievous grin.

"No way man!!" Frank said emphatically. "There is no way I'm doing anything with a hooker! STD's man! No way, NOT for me."

"Good point. We definitely shouldn't do anything that could hurt us or Jenny." agreed Cole.

After much deliberation, Cole and Frank couldn't come to any agreement on what to do for their real-world next-level training. They decided to do the usual and masturbate to porn together. Cole had found another MMF video that put on the TV screen for them as they got into their usual routine. This video was another beauty. The porn studs seemed to be really cool with close proximity actions. Once the porno babe started sucking both cocks at the same time, Cole and Frank were very quick and comfortable to whip out their own cocks and start stroking. As the porno babe was getting her mouth double-penetrated, a crazy idea shot into Cole's mind. "Frank, I got the perfect idea!" he said with great excitement. "Let's double penetrate my fleshlight!" Cole had a fleshlight that used on occasion and the idea seemed perfect to him. Frank, on the other hand, was less than impressed. "Seriously bro! Now I know for sure that you're crazy. No offence, I'm not doing that with you," demanded Frank.

"Well, do you have a better idea? What's it going to be? I came up with two ideas and you're shutting down both of them?" asked Cole with growing irritation in do his voice. "Come on bro! Are you going to let Tyler Frickin Johnson win because you're too much of a homophobe? Our sexual livelihood depends on this!"

"Okay, I get it. Calm down. It just seems really gay to do that. I mean, it's borderline gay even when there's a chick involved, let alone just a flesh-light! Why can't we just try it on Jenny?" Frank questioned back.

"Bro, we both agreed that we needed to be comfortable with dick to dick contact if this was going to work. Think of it this way, if we can get through this, we will be successful with Jenny, no questions asked." Cole said convincingly. "So what's it going to be???? Hooker or flesh-light?"

Frank looked over at the TV and got turned on again by the porno studs double penetrating a pussy. He thought about whether it would be better to practice on a hooker and risk an STD or would Cole's idea of the flesh-light be better. The action on the screen was heating up. While Frank continued to ponder while stroking his cock, the guys on the screen seemed VERY comfortable with the chick bouncing up and down on their cocks squeezed together in an apparently tight pussy.

"Allll-righht!" agreed Frank in disgust. "Let's try the fleshlight but we need to keep the porno on and focus on that."

"Of course, absolutely. Trust me, I'm doing this for Jenny, not for you. Just so we're clear, I'm not gay in any way. But we need to do this in order to get comfortable. I would never want to do this if it weren't for our double team operation." Cole tried to convince Frank.

"I believe you bro. If it feels too weird, just don't get mad if I back out, okay?" Frank said.

"Agreed!" Cole said while sprinting to his bedroom to get the recently cleaned fleshlight. "I'm going to go ahead and clean this baby again." he chuckled.

The moment of truth came when Cole returned with a freshly cleaned fleshlight in his hand and a large bottle of lube. The porno continued to play on TV screen as the guys tried to plan out how to position themselves and the fleshlight. They couldn't stand up to double penetrate it because the angle was all wrong. Frank was reminded of the first MMF video that he and Cole had watched together in which the girl sucking the dicks needed to change positions in order to fit the guys deeper into her mouth.

"Why don't you lie down and I'll straddle your leg like they do in the porno vids? The angle should be better this way." Frank surmised with practicality, like he was solving a construction problem.

"Okay, I'm good with that!" agreed Cole.

Cole took off his pants and lied down on the coffee table on his back with his dick flopping around in anticipation of the new experience.

"Hey man, keep your pants on! I don't want our skin touching!" exclaimed Frank.

"Skin touching?? Are you serious right now?" asked Cole. "The whole point of this is get comfortable so Jenny isn't weirded out by our homophobia. Take your pants off too. We need to be comfortable with our skin touching too." Cole stressed.

"Damni-it Cole, you're right." agreed Frank.

After they disrobed, they got into the DP position again. Frank cringed as his legs touched Cole's. Cole was equally weirded out when Frank's balls slid down and rubbed against his leg. After a bit of uneasy settling, they got in position. Frank continued to look over to the tv screen to get turned on, but he was rock hard without looking and was secretly eager to double penetrate the fleshlight with his best friend. "Okay, let's give this a go." Cole said while filling the fleshilgiht with extra lube.

Cole started off by penetrating the fleshlight first. His cock slid in easily due to the excessive lube. Frank was next. He pressed the tip of his cockhead into the fleshlight, looking toward the tv for inspiration. It was just too tight. Coles cock was pulsating making it more difficult for him to try and penetrate. "Hold still man, I don't think I can get it in there." Frank asked.

Cole tried to contain his pulsating cock. Frank attempted entry once again but no luck. It was just too tight.

Cole sat up to inspect the issue. "Bro, you have to change your angle of entry. Look at the screen. Those cocks are parallel, making entry easier." Cole reasoned.

"No, for this work, I need you to pull out your cock so that only the tip of your dick is inside the fleshlight." Frank said.

Cole pulled out so that only his tip was in the fleshlight. Frank squeezed the tip of his dick against Cole's and they were suddenly both inside of the fleshlight. They both grinned at the sight of this. The next step was to see if they could fuck the fleshlight. Slowly Cole pushed the fleshlight down on their stationary dicks. Incredible pleasure pulsated through both of their bodies as their cocks squished together inside the fleshlight. Cole pushed down as far as he could but there was no way the fleshlight could take them all the down. The squirmed and adjusted angles trying to make this happen. Finally it happened. They found the perfect angle for both of their cocks to be completely engulfed by the fleshlight. "Ohh yeah, that feels so good. Yes!" Frank encouraged Cole as slowly started to pump the fleshlight on and off of their dicks.

"Ohh, this feels amazing. Just imagine how good Jenny's pussy will feel!" exclaimed Cole. They continued to pump away on the fleshlight. Cole would sometimes stroke the fleshlight while sometimes he would hold it still and allow Frank to thrust his dick in and out. The sensation was amazing for Cole. He loved the feeling of his best friend's dick rubbing against his inside the fleshlight.

"Let me try the top now." demanded Cole, feel as though he was missing out on a different sensation.

"Okay , okay. Hold your horses." Frank said while dismounting and reaching for more lube.

The friends switched positions and even Frank was surprised as to how much he was enjoying the experience. He seemed eager to get back inside the fleshlight with his friend. Frank switched to the bottom while Cole mounted the top. Frank felt the same gross feeling when Cole's balls drooped down rubbing on his leg. They penetrated the fleshlight again, this time much easier as they had the angle and methodology established. Cole immediately began thrusting while Frank held the fleshlight. Their legs were touching, they were high-fiving, and their dicks were rubbing together. Neither of them felt like it was weird or gross. It felt amazing for them and didn't feel gay.

Like a soldier prepares for war through rigorous training, Cole and Frank pumped away at the fleshlight pretending that it was Jenny. "Oh Jenny, you feel so good." "Jenny your pussy feels so tight!" they both vocalized their pleasure pretending that the fleshlight was Jenny. The switched up positions and figured out the they could both be standing and double penetrate the fleshlight. They just needed stand close together with their cocks pressed together and pointing towards the ceiling. This angle was a lot of fun as they pulled their cocks in and out.

They continued to experiment with different rhythms and angles until neither of them could take much more of this. The absence of a female allowed them to last a little longer and their dicks were getting a little sore. "Okay, I'm about to cum. I'll ejaculate into the fleshlight. Can you take the kleenex?" Frank asked.

"Sure go for it." Cole took his dick out while Frank pumped away on the fleshlight. The fleshlight felt very empty for Frank without his best friend in there with him. But he was able to climax with ease while watching the porno that continued to play on the TV. Cole finished in some kleenex as well. However, both were craving much more.

They were successful in their training. They felt ready for Jenny.