The Double Team Ch. 03: Operation J

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Frank and Cole double penetrate Jenny's mouth & pussy.
3.8k words
4.51
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Part 3 of the 3 part series

Updated 06/07/2023
Created 05/05/2016
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Operation Jenny

The bar was too loud for Jenny and Frank. They moved tables to a quieter section away from the dance floor where they could talk. They were waiting for Cole to arrive. Jenny has delighted to have a little alone time with her crush. She was confused as to why Cole was joining them.

"Frank, you promise that you're not trying to get me back together with Cole, right?" Jenny confirmed making sure that Cole's intentions were pure.

"Cole just wants to remain a close friend of yours, as do I. That's all this is." Frank reassured her. The music pumped in the background as Jenny's body looked ravishing in the club lighting. She was dressed up to the nines wearing a skimpy purple dress that showed off her rocking athletic body. The fabric of the dress clinged to her body and exposed every curve.

Although she would never say it aloud, Jenny wanted nothing to do with Cole sexually again. She had been there, done that. She was looking for someone to provide her with the pleasure that Tyler Johnson had. Unbeknownst to her, Frank wasn't able to to provide her with that girthy pleasure either. Jenny was curious to find out if Frank was packing.

"Cole! You found us. Get in her for a hug!" Frank extended his arms out welcoming his best friend. Cole embraced Frank in a close hug. Jenny quickly became jealous of the guys hugging and made sure to make herself available for a hug from her ex.

"Jenny, you look more beautiful than ever! Don't tell Frank, but I'm looking forward to hugging you a lot more him." Cole laughed while placing his arms around his former lover. His hand placement was low, encroaching on her butt, but not enough to be disrespectful.

Jenny was excited to see Cole again. Memories of their past love-making raced through her mind. She was starting to get turned on but had to keep her horniness in check. "Why did I break up with this hunk?" she thought to herself. "Oh yeah, he has too thin of cock, that's why!" she reminded herself. But Cole was ripped to the same level as Frank. Both guys were confident in their appearance.

After they got caught up, the drinks continued to flow. Frank and Cole had rehearsed and practiced bringing up the idea of threesome to Jenny and were getting close. Both guys were flirting with her excessively and Jenny was loving it. Thump. Thump. Thump. The club beats continued as one of Jenny's favorite songs came on. "Jenny, we need to get you out on the dance floor! We are at a dance club after all!" Frank said, signifying that the first move in "Operation Jenny" was made. Jenny couldn't help but agree. "Well, there's three of us, we can't leave anyone behind." reasoned Jenny while standing up and starting to move to the music.

"Easy, both of us will dance with you." said Cole.

The threesome made their way to the dance floor. Neon lighting filled the room while other couples danced to electro beats radiating from a local DJ's table. Jenny and Frank were facing each other dancing while Cole inched closer to the couple, making sure to watch for signs of uncomfortability from Jenny. Jenny was quick to include Cole, inviting him closer as they gyrated to the music. "Jenny, you're so hot, I can't take it." Frank whispered into her left ear while Cole was almost close enough to hear. As soon as Frank finished whispering, Cole leaned to in to whisper in her right ear. "Mmmm, I miss our times together but I'm having a lot of fun with you here, like this." Cole whispered. Jenny was melting. She had two body building hot hunks whispering sweet nothings into her ears. The guys seemed to do this in waves like a coordinated army assault, slowly breaking down any sexual defence that Jenny's willpower could muster. She wanted both of them to fuck her right there on the dance floor but wasn't "that" type of girl. She never had been close to a threesome before in her life. The guys continued to tease and laughed with her about making a Jenny sandwich as they both came in close on either side of her.

After a few more songs Frank took the next step. "Jenny, do you want to get out here? I have something I'd like to show you at my place." Frank whispered with a smirk with Cole still in close dance proximity.

Jenny whispered back in Frank's ear, "Yes, I'd like that, but what about Cole?" Jenny asked discretely.

"Cole is a part of this too. It's okay, we both want you and we share everything." Frank said with a smirk.

Jenny heart did a flip with her stomach upon hearing this. She had fantasized about being with two men before but would never admit it. She had heard from a few of her friends who had tried a boy-boy-girl threesome that it was awesome if it was done right. She was worried about past feelings with Cole affecting the threesome. "Frank, I don't want to complicate things with Cole and I." she said quietly enough so Cole wouldn't hear.

"It's alright, he's okay. Just come over and if it doesn't feel right, then no pressure." Frank said while taking Jenny's hand and leading her towards the door.

Frank shot an excited look Cole's way as he signalled that they were leaving. Frank took Jenny's hand to the exit with Cole close behind. Once outside, a cab magically appeared and the three jumped into the back seat. Jenny was seated in the middle, of course. As the cab made the drive to Frank's apartment, their hands started to wander. Cole watched as Frank's hand grasped the the beautiful left leg of Jenny. Jenny encouraged this while grabbing Frank's leg, carefully not to tip off the cab driver as to what was going on. Not be left out, Cole placed his hand delicately on Jenny's right leg.

Jenny was startled by this. The whole thing felt very uncomfortable for her but she was burning with desire and really wanted Frank. "It's okay. You've already been with Cole so he doesn't count. It's okay to be with him as well because you've done that before." Jenny reasoned with herself allowing Cole to touch her leg. With both guys touching her legs below the sightlines of the cab driver, Jenny's pussy got extremely wet as she filled with desire for both of the guys. She pushed her societal fears away and bought into the idea of a threesome. "I'm going to fuck both of these guys!" she convinced herself as their hands inched closer to her pussy. The guys both leaned in closer towards Jenny as she felt their breath on her neck from either side. She couldn't wait to find out what it felt like once they got naked. The guys took turns kissing Jenny in the back of the cab. The driver must have been confused as one moment, Jenny was kissing the guy on her left, the next moment, the guy on her right. To prove their commitment that they would both play nice together with her, Frank leaned in while Jenny was kissing Cole. Both guys inched their lips closer together while Jenny in the middle was in awe of the threeway kiss (although Frank and Cole's lips never touched each others).

Thankfully for all involved, the cab driver arrived at Frank's apartment. After quickly paying for the fair, they raced up to Frank's place. Without any hesitation, the groping and kissing went to the next level as soon as they entered the privacy of Frank's home. They quickly found the couch and plopped down. Cole and Jenny were in a deep kiss with Frank beside encouraging them. "Cole, I had forgotten how good of kisser your were! I really have missed it. Both of you guys are amazing kissers." Jenny was quick to include Frank who was near their mouths. Cole deeply missed Jenny's kisses as well and wouldn't let Frank's lips stop him from kissing her again. He leaned in to get more kisses from Jenny while trying his best not to contact Frank's lips. "Ohh, this is so hot!" blurted out Jenny who was absolutely loving the dual attention.

Both guys slowly kissed Jenny all over while disrobing her and themselves in the process. Jenny was very comfortable with her naked body as it was beautiful and she felt confident in herself. Her light coloured skin was slightly tanned. Her breasts were smaller but formed nicely. The arch of her back and butt was an understated quality of hers. Frank and Cole quickly disrobed revealing their rock hard, albeit skinnier than average, boners. Jenny loved the sight before her eyes and quickly went down them. Cole was instantly reminded of how good Jenny's mouth felt on this cock as she started sucking him off first.

Jenny was surprised with how comfortable the guys were around each other. She had always assumed that guys were homophobic. While going down on Cole, she looked up and Frank's cock was right there beside her face. She didn't have to move very far to start going down on him. Frank moaned in pleasure and looked over to Cole with a delighted smile on his face. Now, the guys moved their cocks closer together to encourage Jenny to suck on both of them at the same time. Cole leaned in closer to Frank to get his cock closer to Jenny's mouth. As she sucked on Frank's cock, Cole took his cock and tried to pry it into the corner of Jenny's mouth. Jenny chuckled and took Cole's cock at it's base, playing along. She pressed both cock heads into her mouth at the same time while looking up at both guys. She was expecting to see a negative reaction to this. Instead, the guys were both smiling from ear to ear as they pushed their bodies and cocks closer together in order to create a parallel angle. Jenny was shocked but loved the idea of pressing their dicks together. Whack! She slapped both dicks against each other playfully.

Frank and Cole stood facing each other with their pelvises pressed firmly together. Their cocks were jammed together pointing straight up towards the ceiling. There was barely enough space in between Frank and Cole's stomach for Jenny's head. Jenny was taking both of them deep into her mouth and was loving the new angle that allowed her to do so. "Oh my, this is so fucking hot! Hmmmm, these cocks filling my mouth is so hot!" she said as the guys gave each other a high five. Rather than having Jenny's head bob up and down, Cole held her head still as both guys started to thrust their dicks into her mouth. Their dicks rubbed together inside of Jenny's mouth and both guys loved every second of it. Jenny loved it too. She jerked off both cocks in her hand while smiling seductively up at the guys. Her right hand struggled to fit around both cocks but she made a C-shape with her hand and stroked up and down on both of the cocks while squeezing them tightly together. Jenny was fascinated that guys allowed her to do this. In fact, they seemed to be encouraging it. "Wow, you guys are REALLY comfortable with each here!" she exclaimed while admiring both dicks in her hand.

"Just think of both of us as one very large cock." Cole chimed in while smiling.

"Yes, we want you to have the maximum pleasure Jenny. With double the dick, we're hoping it will give you double the pleasure." Frank said while thrusting his cock in Jenny's hand.

A thought popped into Jenny's mind when Frank mentioned "double the pleasure". "These guys want to double fuck my pussy!" she finally realized. She looked down at both cocks in her hand and was reminded of Tyler Johnson massive cock. It seemed to be roughly the same size as both Frank's and Coles pressed together. She squeezed their dicks a little harder trying to mentally determine if her pussy could handle both of them. She started to realize having two inside of her pussy could feel really good for her, possibly even better than having one large Tyler Johnson. "Hmmmm, I need you guys to fuck my pussy now." Jenny said while looking up to both guys.

Cole repositioned Jenny to a missionary position. Both Frank and Cole thought that it would be easier for Jenny to take both of them if they warmed her up first with one. Cole, having made love to Jenny many times before, was the obvious choice to begin the proceedings. Jenny's pussy was dripping wet in anticipation for Cole. She was so turned on and loved the slow entry that Cole came in at. Jenny quickly adjusted to Cole's size. After all, her pussy was recently being filled by the size king Tyler Johnson. Cole felt a little more room in Jenny's pussy that he remembered and thought to himself "Frickin Tyler Johnson". As Cole was on top of Jenny slowly pumping his dick in her pussy, Frank kneeled in closer to get his cock closer to Jenny's lips. The major problem here is that Cole's head was in close proximity. As Jenny slowly sucked on Frank's cock, she noticed the close proximity of Cole's face as well and wondered if he would start sucking. "So Cole, are you going to suck Frank's cock too?" she asked.

"Hahaha, no Jenny." Cole shot back being careful not to get offended. "Frank and I are close, but we're only close for your pleasure. We're not into each other or guys." Cole confirmed while kissing her cheek with Frank's cock only centimeters from Cole's face.

"Okay, just making sure." Jenny said. She was glad that the guys sole focus would be on her. She thought it would be weird if they started fucking and sucking each other. She took Frank deeper in her mouth as Cole pumped her harder.

They had switched positions and places, each guy getting to experience Jenny's pussy on their own. It was now time join forces. Frank was underneath Jenny who was in the reverse cowgirl position. Cole reached over to grab some lube in anticipation of a tight fit. "Ohhh, I'm excited to have both you boys in me. Please go very slowly, I don't know if I can handle you both." Jenny said shyly. She knew full well she could take both of them. Cole dripped down lubrication onto Jenny's pussy and Frank's cock as he pumped slowly. Cole dripped some lube on his cock and began to get closer to into a dp position. The guys shifted positions slightly and Frank pulled out to just his tip as they had practiced with the fleshflight. Cole pressed his cockhead down onto Frank's cock as he checked his alignment one final time before entry. Jenny screamed with delight as both penises started to slowly enter her pussy. They were careful to give her time to adjust to the new girth but both guys were excited as hell to begin exploring deeper. Slowly, the guys continued to get deeper a millimeter at a time without thrusting too quickly.

"Oh, yes, yes, you can a little bit faster now." Jenny encouraged the guys, thankful that they were starting off slowly. The guys started to thrust in and out carefully in Jenny's pussy. "Holy Shit, this feels incredible!" Jenny continued to scream as the guys got into a rhythm. Her pussy was wrapped tightly around both of their dicks. So tight, in fact, that the guys could feel the throbs of each other's cocks when stationary.

The pace quickened as their dicks went further into her pussy. The parallel angle of their dicks allowed for a deeper penetration. At this time, their rhythm had changed from a conjunctive pattern to an alternating one. One cock would pull in as the other was pulling out. Jenny was screaming in ecstasy while loving every second in what seemed to be a state of constant orgasm. The sensation was too much for the guys. Having the combined sensation of the tightness of Jenny's pussy and the dick friction of the alternating thrusting was sending them both over the edge. They slowed their pace to last longer.

Jenny arched back to kiss Cole who was now positioned behind her. "Come on guys, fuck me harder!" She urged the both of the guys to continue fucking her but Cole and Frank remained stationary so not to ejaculate too quickly. Jenny furiously took matters into her own hands and started to grind her pussy down on the stationary dicks. She pushed her ass back towards the base of the dicks, taking more and more into her pussy with each stroke. She gave her ass a twitch while she continued to grind, her skin glistening with sweat. Frank and Cole both felt their cocks squeeze tighter together as Jenny's pussy contracted and tightened.

"Oh shit, I'm cumming!" Cole exclaimed. "Frank, cum with me at the same time so it's not weird." Cole asked.

Frank chuckled as it was already plenty weird. His cock was occupying the same pussy as his best friend. He was just about to cum at the same time, into the same pussy, with his best friend, into his best-friend's ex-girlfriend. He was past the point of it being weird and he loved it. "Yes bro, you say when!" Frank agreed.

Jenny pushed her pussy back all the way while Cole grabbed both of her ample ass cheeks with his hands. He pushed her back and forth on his and Frank's dicks. Jenny screamed in pleasure as she finally had gotten some action out the guys. "Ohh, ohhh, I'm cumming!" exclaimed Cole.

Frank felt a sudden addition of warmth and lubrication fill into Jenny's pussy as Cole pushed her back and forth. Frank thrusted more, enjoying the additional lubrication provided by Cole's cum. "Ohhh, me too! Yes, It's amazing!" he cried out while busting his nut. Jenny moaned the whole time, hoping the her night of double pussy penetration wasn't over. Frank and Cole had just ejaculated almost simultaneously into Jenny's pussy. This realization set in that their dicks were covered in each other's semen inside of Jenny. They stayed motionless in Jenny's pussy as their combined juices slowly dripped out onto Frank.

"Holy shit that was so hot!" Jenny moaned. She was clearly still in the mood for as she slowly rocked back and forth on the softening dicks. "Mmmmm, you boys like that?" She asked.

"Oh Jenny, you are absolutely amazingly hot. This was incredible." Frank reassured her. Jenny rocked back and forth a bit more.

"Sooooooooo, how did we do? I mean, compared to other experiences that you've had, how did we do?" Cole asked trying to pry out of her if they were better than Tyler Johnson.

"The way you guys filled me up was better than anything I've ever experienced in my life! Seriously! You have no idea how amazing it is to have two dicks pulsing back and forth." Jenny said excitedly.

"Better than Tyler Johnson?" Cole asked getting to the point.

"Wayyyyyyyyyyyy better!" Jenny quickly replied.

Upon revelation that they had dethroned Tyler Johnson, both Frank and Cole's dicks stiffened up a bit still inside the cum filled pussy of Jenny. Jenny, clearly wanting more, began to grind on dicks more sensing that the guys were actually turned on by the revelation that they did a better job of fucking her than Tyler Johnson had. With semen as lube, the guys got into a better rhythm as their dicks hardened. "Oh yes, you guys want more!" Jenny got excited again.

They switched positions to see to reverse cowgirl with Cole back on the bottom. Jenny enjoyed looking towards Frank with his ripped body. Frank entered her pussy with easy as he and Cole fucked Jenny deeper. Frank was able to grab Jenny's tits with both hands as he pounded more vigorously.

Frank and Cole were able to fuck Jenny much harder after ejaculating once. She loved it and continued to encourage them knowing they got off on their domination of Tyler Johnson. "Oh yeah, Tyler Johnson has got nothing on you guys! Mmmmm you fuck so good together!" She screamed while having multiple orgasms.

The guys quickened their pace fully penetrating her pussy with every stroke. Their body's full of dripping sweat from the workout. As they got closer to climaxing for a second time, Cole made a request. "Jenny, can you suck us off?" Cole asked knowing that she had no aversion to semen in her mouth.

"Oh yes, I love your dicks in my mouth. I want you both to cum together in my mouth." She demanded while quickly dismounting.

Frank and Cole stayed in the same dp position as Jenny repositioned herself to suck both of their dicks. She teased them by sucking one dick at a time first. Then, with her right hand, she grabbed both dicks in her hand and stretched her lips over their cock heads. She licked up the remnants of semen and vaginal juices from their double vag experience. The guys were wanting to bust their load soon.

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