Carrie Gives an Encore (Part 2)

Title: Carrie Gives an Encore (Part 2)

Author: TheBigLove126

Celebs: Carrie Underwood, Cassadee Pope

Codes: MMF, MF, cons, oral, anal

Summary: Carrie returns to Boston with an opening act

Disclaimer: The following story is (probably) fictional and does not (but might) be a recollection of any true events (but one can hope it is). Enjoy!

If you have any questions, comments, story requests or other feedback to this or any of my other stories; feel free to contact me at – or chat with me on YIM, I am almost always online.

Carrie sat in her dressing room at TD Garden in Boston. It was the first time performing at the arena in over two years. It was also the first time back in this dressing room; the same dressing room where she first met Jed the maintenance man. She had been looking forward to coming back ever since she left her hotel room the morning after they met.

The blonde superstar sat in the dressing room, just minutes before going on stage. Her new opener, Cassadee Pope, was about to perform her final song. Carrie grabbed her phone and sent Jed a quick text message.

“Hey babe, about to go on stage, wait for me in the dressing room. Can’t wait!”

She put her phone away and headed for the stage. She quickly adjusted her silver tank top and short cut jeans to make sure she was looking her best for the performance. As Carrie made her way to the entrance, Cassadee walked by and hugged her.

“Thanks again for letting me join you on tour,” the young ‘Voice’ champion said. “The crowd is on fire out there.”

“No problem, sweetie. I couldn’t think of a better person,” Carrie responded.

“Wait!” Cassadee said before Carrie walked on stage. “The shower in my dressing room isn’t working, could I use yours?”

Carrie looked at her, knowing that Jed would be arriving in the room soon to wait. A devilish smile came to her face.

“Sure thing, I hope you enjoy it as much as I do,” she said.

“It’s just a shower,” Cassadee responded, somewhat confused. “Anyway, have fun out there.”

Carrie giggled as she thought of what was truly awaiting her twenty-four year old opener. She made it on stage and began her set for the hot crowd.

Meanwhile, Cassadee entered Carrie’s dressing room and headed straight for the shower. Once in the bathroom, she pulled her red tank top off over her head and placed it on the rack. Off came the bra, her jeans, panties and knee-high boots. She walked into the shower and started cleaning off.

While the young woman was showering, Carrie’s “friend” Jed made his way into the dressing room. He heard the shower running and got very excited. He had been too busy working that he was completely unaware of what was going on in the arena. He thought immediately that Carrie was the one in the shower.

Jed quickly removed all of his clothing and started towards the door. He got excited when he turned the knob and realized that it was unlocked. He stroked his thick cock to get fully excited for his fuck-buddy of the night. He could only see a fleshy figure behind the glass door of the shower. Quietly, he made his way over and opened the door.

“Hey babe!” he yelled before realizing that it was not Carrie in there.

“Ahhh!” Cassadee screamed. “What the fuck!”

“I’m so sorry,” Jed said as he ran out of the room.

Cassadee grabbed a towel, covered her wet body up and followed him.

“What the fuck is going on!?” she yelled as Jed fumbled around to gather his clothes.

“I’m sorry, I thought you were Carrie,” he explained.

“Carrie? She’s a married woman,” she said.

“I know but she doesn’t care. We had sex the last time she came here and she invited me into this room a few minutes ago so we could do it again,” he said, pulling his jeans back on.

Cassadee stopped for a second and thought back to the conversation she had with Carrie earlier. It did not take long for her mind to click. This was what Carrie was talking about when she said, “enjoy it as much as I do”. Carrie had set her up.

“Wait,” she said. “I think I know what’s going on. I asked Carrie before she went on stage if I could use her shower. I guess she had already invited you over.”

“I guess so,” he said as he put his shirt on. “I’m really sorry again. I’ll leave.”

“Wait!” Cassadee yelled out. “Carrie told me to ‘enjoy’ the dressing room as much as she does,” she said as she slowly walked over to Jed, looking somewhat nervous. “Maybe I should take her advice.”

Cassadee walked past him and locked the door. She looked over shoulder and gave him a cute smile before letting her towel drop on the floor. Jed’s eyes went straight to her perfectly round ass. He walked up to her and spun her around, giving himself a better look at her front side. He softly squeezed each of her breasts while she pulled him in for a kiss.

As they kissed, her hands slid down until they were at the top of his jeans. Slowly, she pulled them down and felt his thick, eight inch cock press against her thigh. She had been scared the first time she saw him naked and had not gotten a good look. She broke the kiss and looked down, causing her jaw to drop.

“Holy shit!” she yelled. “No wonder Carrie likes you so much!”

“And I can tell that you like it too,” he said, stroking one of the blonde streaks in her hair.

Cassadee looked up at him for a brief second to smile before turning her attention back to his cock. Slowly, she reached for it and timidly grabbed it. She giggled at the first touch and started stroking it. She gasped as her hand went up and down. Never before had she seen a penis this big before; she was in awe.

Jed removed his shirt and started kissing her neck, causing her to stroke him faster. She closed her eyes and jerked him off faster. She was lost in her feeling of lust.

“Wanna taste?” he whispered into her ear before kissing it.

Without saying a word, Cassadee slowly dropped to her knees and got an up-close look at his large member. She smiled, opened her mouth and pulled it in. She giggled as his head slid down her tongue and towards the back of her throat. She easily took five inches before she felt it start to go down her throat. To Jed’s surprise, the other three inches went in with no struggle.

“No gag reflex…I like,” he said with a laugh.

Jed grabbed each side of her head and slowly started to fuck her throat. She dropped both of her hands to her side and allowed herself to be controlled. She stared straight up at him as his cock went in and out of her tight throat. Her eyes started to water, her nose began to run and slobber started to drip out of the corners of her mouth as he increased the pace. For several minutes, he fucked her throat before he had to pull out and avoid cumming too quickly.

Cassadee coughed for a few seconds before looking back up at him. Her face was a wet mess but neither of them cared. Jed helped her to her feet and led her to the couch in the corner. She sat down while he knelt down and spread her legs open. He could smell the excitement coming from her crotch as he drew his mouth closer.

The young singer jumped at the first touch of his tongue to her soaking wet pussy. After the first touch, she stared up at the ceiling with her mouth wide open. She felt his lips press against her pussy lips, tongue going in as deep as possible. This was the first time in years that Cassadee had received oral pleasure and this was by far the best. He used his thumb to tickle her clit while the rest of hand grabbed at the short patch of pubic hair above it. He kissed and sucked at her pussy lips while his tongue explored every bit of her vaginal walls.

“Holy fuck,” she whispered. “Holy fucking fuck.”

Jed continued his gentle assault of her crotch, laughing at her quiet words. He knew that she loved this and made sure to keep things that way. He used two fingers to massage her clit while continuing to cover every bit of her vagina with his tongue.

Cassadee’s breathing started to get heavier as her clit was being stimulated more and more. She knew that it would not take long for an orgasm to wash over her body. Her hips started slowly thrusting against his face. Her hands were grasping tighter and tighter to the cushions of the couch. Beads of sweat were forming all over her body. The tingle in her pussy was beginning to spread throughout the rest of her body. It was coming.

Jed started furiously licking at Cassadee’s beat-red clit as he sensed what was about to happen. She took one more deep breath before her body tensed up and she exploded in a massive orgasm. Her eyes and mouth shot wide open as the best orgasm of her young life soaked Jed’s mouth and chin. He still sucked at her clit until her body finally relaxed and she took a deep sigh.

“Wow,” she softly said.

“Wow indeed,” he responded.

As Cassadee remained still, breathing heavily and recovering from her orgasm, Jed stood up and lined his large cock against her dripping-wet hole.

“Ready?” he asked.

Cassadee looked at him, closed her eyes and nodded her head while smiling. Jed slowly started inserting his cock into her, causing her to gasp again. Even though she was soaking wet down there, his cock was still massive and stretched her pussy farther than it had ever been stretched before.

Just like he did with her throat, Jed started slowly fucking her pussy but quickly increased the pace. Within a minute, he was fucking her like a wild animal…and she loved every second of it. She was moaning and grunting in unison with each thrust while her eyes were locked on his. She smiled as her hips thrusted, also in unison with his.

Cassadee wrapped her arms around his neck as he stood up, lifting her from the wet couch. She locked her lips onto his as she bounced up and down on his cock. She took full control and fucked him more than he was fucking her. They held each other tight and kept up the pace for several minutes until Jed backed her up against the wall. She pressed her back against the wall and let him take control once again. He fucked her against the wall for about a minute before she pushed him away.

Cassadee, now back on her feet, turned around, put her hands against the wall and bent over. Jed instantly re-inserted his cock into her pussy and started fucking her again. He grasped onto her hips and slammed her harder than he had before. She was still moaning, only now was doing it much louder than before.

“Oh yes! Fuck me harder! Harder! Fucking harder!” she screamed.

Jed fucked her as hard and fast as he possibly could, enjoying every second of it. Slowly, Cassadee started standing up straight until she her breasts were pressed against the wall. She started slapping the wall and shouting “yes” with each thrust. It did not take long for him to figure out why. Her body went stiff while her pussy contracted around him, giving her another massive orgasm. She looked over her shoulder and stared at Jed, her eyes trying to roll to the back of her head.

Once her orgasm subsided, Cassadee pulled away from Jed and lay down on the couch. He followed her and, as soon as she was comfortable, he put his cock back inside her and gently fucked her. He knew she was worn out and wanted to give her a calming finish. He went at about half the speed of his earlier fucking but it was still enough for him to reach his finishing point.

Jed pulled out of Cassadee’s pussy and stood over her. She opened her mouth and closed her eyes as he aimed his cock at her face. Seconds later, large globs of his thick cum shot onto the young woman’s face. Most of his seed went into her mouth with just a small amount landing on her cheek. She sucked the leftover cum off of his cock for a few seconds before he pulled out and sat on the floor.

“Damn,” he said.

“Damn,” she said before they both laughed. “I didn’t expect that tonight but…I’m glad I asked to use Carrie’s shower.”

“Me too, you were great,” he responded.

Slowly, Cassadee stood up and walked back into the bathroom. Minutes later she came out fully dressed in her red tank top, jeans and boots. She grabbed her bag off the floor and started to walk towards the door when she stopped. She turned around and went back to Jed, handing him a piece of paper with a phone number on it.

“Call me sometime,” she said.

As she unlocked and opened the door, she was met instantly by Carrie, who was about to enter.

“Hey how was the shower?” Carrie asked.

“It was amazing,” Cassadee said with a huge smile on her face.

“I can tell,” Carrie said as she rubbed her finger against the younger woman’s cheek. “You might want to clean Jed’s cum off your face before you start walking around in a crowd of people.”

“Oh shit!” Cassadee yelled.

“Don’t worry,” Carrie said before licking her cheek and showing her a white glob on her tongue. “Got it all. Goodnight Cass.”

“Night,” she said as she walked away, still in a bliss.

Carrie locked the door behind her and saw Jed sitting on the couch, still naked and next to the wet spot from Cassadee’s first orgasm.

“I guess you liked my surprise,” she said as she started to strip.

“Very much so, but I just came five minutes ago. I don’t think I can go right now,” he explained.

“Well, maybe I have to find someone to fuck while you recover. I’m too damn wet to wait,” Carrie said as she pulled her shorts down to reveal her white panties with a giant wet spot.

“My friend Mike is working maintenance right now and he’s going through a divorce. I’m sure nothing would make her happier.”

Carrie took her cell phone out of her bag and handed it to him. “Call him!”

After a quick phone call, Jed let Carrie know that Mike was on his way. She gave him a deep kiss before slowly crawling away from him and towards the door. She sat down cross-legged and waited for the other man to arrive. Five minutes later, the door opened and Mike walked in.

“Hey Je…whoa,” he said as he saw a very naked Carrie Underwood smiling at him from the floor.

“I hear you need something to get your mind of the divorce,” she said as she reached for the zipper of his pants. “I think I know what you need.”

Carrie giggled as she reached in and pulled his cock out of his jeans. While it was not as thick as Jed’s, it was at least the same length or even a bit longer. She instantly wrapped her warm lips around it and gave him a nice, slow blowjob.

“Jed man, how did you score this?” he asked his friend while his cock was being washed.

“Pure luck. I just got done fucking her opening act, she needed something to play with until I’m ready to go again,” Jed explained.

“Damn, you got Cassadee and Carrie…lucky bastard,” he said before looking down at Carrie who was happily flicking her tongue against the head of his cock.

Carrie worked his cock like the slutty pro that she was. She softly sucked on the head while working both hands up and down at a rapid pace. Then she started to deep throat him, filling the room with the sounds of her gagging. When she pulled out, a long string of slobber kept her connected to him. She slowly sucked it up before taking him deep again.

While she was busy choking on Mike’s cock, Jed had gotten off the couch and crawled behind her. He lay down on the ground and slid under her body until her pussy was directly above his mouth. Carrie lowered herself down and let him give her the same oral pleasure that he had given Cassadee earlier. His lips wrapped around hers and his tongue slid inside.

Mike felt each of Carrie’s moans through his cock as Jed attacked her cunt. She was very wet which led to easy entry for him. With the position he was in, his tongue could not help but flick against her clit. Each flick led to a deeper moan which led to a hard vibration for Mike. This almost led to him cumming quickly but he was able to restrain it.

“Fuck my throat, Mike,” Carrie said, pulling his cock out for a second before taking it back in and dropping her arms to her side. “And you,” she said, looking at Jed. “Enough tongue, I want your cock.”

As Jed slid out from under the singer, Mike took control and violently fucked her mouth. Carrie closed her eyes and purred like a kitten as her throat was violated. She dropped to her hands and knees to give Jed easier access. He grabbed his thick cock and easily slid it between her moist lips.

Carrie was being fucked from both ends and was loving every second of it. She would have encouraged Jed to fuck her harder (even though he was fucking her pretty hard already) but her mouth was a little full at the moment. Mike was taking no mercy on the singer’s prized possession, her throat. All the frustration of his personal life was being put to good use by making Carrie Underwood his bitch.

Meanwhile, Jed had his hands tightly grasped around her waist as he thrusted in and out as hard as he possibly could. It had been over two years since he was able to have sex with the blonde superstar and he was not wasting the opportunity. She arched her back with each thrust, showing just how much she was enjoying the vicious pounding he was giving her.

Suddenly Carrie placed a hand on Mike’s thigh and pushed him away.

“Mike, get under me and take my pussy,” she said before turning to Jed. “You get my ass.”

The men repositioned themselves, Mike under Carrie and Jed standing over her. Both men inserted each hole at the same time. Obviously, with the tighter hole and thicker cock, Jed had some more work to do to get fully inside her. It took him no time before all eight inches were deep in her rectum. Within a minute, both men were fucking her at the same pace they were earlier.

Now with her mouth free, Carrie was finally able to moan, groan and scream audibly.

“Oh…fuck yes…harder Mike…fucking hell…harder…both of you…yes…fuck me harder…mmm!” she shouted.

Sweat was dripping down Carrie’s face as both of her holes were abused hard. She felt an orgasm coming on and did nothing to slow it down. She closed her eyes and screamed as it hit her like a ton of bricks. Her body tensed up and she let out very soft moans with little to no time in between. Both men could feel her body’s reaction which almost caused them to cum.

Mike slid out from under Carrie and stood in front of her face. She smiled and opened her mouth just in time for him to release a massive amount of cum from his cock. It was the first orgasm he had had in a long time, which meant that Carrie got one of the biggest loads of her life hitting her entire face. From her hair to her chin, she was painted in a thick white glaze.

She took Mike’s cock in her mouth to clean any leftover cum from it when she felt Jed pull out of her ass. Before she could react, she felt his warm cum land on her back. While his load was not as big as Mike’s, she was still coated in another large amount of cum. She could feel each little sperm swimming down her back. Jed slapped his cock against her asshole until it was cleaned.

Once Mike’s cock was clean, Carrie sat down on the floor and started scooping the cum from her face and swallowing it while the men relaxed, watching her. They sat and watched for several minutes as she completely cleaned her face off.

“That was fucking amazing,” she said, sucking her fingers clean. “I love Boston.”

“And I love when you come to Boston,” Jed said.

“What are you doing for the rest of the night?” Mike asked Carrie.

She looked at Jed, almost asking for permission to go with him.

“She’s yours for the night man,” he said as he held up the paper with Cassadee’s number. “I don’t think Cassadee is done for the night.”

All three of them got cleaned up and dressed. Mike left with Carrie while Jed called Cassadee.

“Hey, you ready for round two?” he asked over the phone.

“You know I am,” Cassadee said as she walked into the room. “Next time, you might want to close the door before you start double teaming Carrie. I walked by and saw the whole thing. Don’t worry, no one else saw you,” she said before hanging up the phone and pressing her hand up to Jed’s face. “Can you guess what I did while I watched you?”

He took a deep whiff of the leftover feminine juice on her hand.

“Let’s go,” he said as they walked out of the dressing room.

This entry was posted in Anal, Cons, MF, MMF, Oral, TheBigLove126 and tagged , . Bookmark the permalink.