Taylor Swift: Victoria's Secret Affair

[RyanMasters]

Fantasy. Obviously. This is a fan-based parody and never happened. Taylor Swift in this universe has a contract with Victoria’s Secret as a performer and model.
Tags: Taylor Swift, oral, vaginal, creampie, M/F
(Time: July 3rd-5th, 2015)
Taylor Swift walked into a Victoria’s Secret photoshoot as per a contract she signed with CFO Ryan Masters. “Good morning, Ryan.”

He addressed her, “Good morning, Taylor. I’m glad you arrived for the July entry of the Victoria’s Secret photoshoot for the new catalogs to be printed in August. I have a July 4th celebration as well, and I am inviting many of the Angels and you to it. It will be at my mansion. .”


Taylor Swift answered, “Thank you, Ryan. I’ll be attending. Your support for my touring and my career has been very useful. Make sure that all this does not interfere with my singing. As for the photoshoot, let us begin.”

The executive states, “As you wish.”
Ryan goes and gets a photographer and the process starts. Taylor Swift tries out various outfits for the photoshoot and its catalog, while Taylor graciously poses according to the photographer’s instructions. This is done in about two hours, and by the end of it Ryan is starting to get very turned on. It was barely after he had helped reset the equipment for the next model that he approached Taylor Swift.

“When you are ready, maybe we should go to the runway, or perhaps to my office.” Ryan was feeling lustful, as he normally did around his favorite blonde singer.



She was puzzled. “Now? When you’re on your job?”

Ryan retorts, “I do have some finances to measure, but maybe you could accompany me there. You are a capable businesswoman, after all.”

Taylor muses, “Hmm. Maybe I’ll do it and see what I can do.” She was willing to look at the company finances.

They both walked into Ryan’s office. It was well-furnished, as befitting his station in Victoria’s Secret. He was highly competent at his job, and this could be seen by the marked increase in sales after getting Taylor Swift on their program. Ryan sat on his main chair and Taylor pulled up a second one to his left.

The Victoria’s Secret executive felt like he was wound up like a spring for some reason. He didn’t feel like this with the models, just with Taylor Swift. The door of his office was already closed, and it was well soundproofed. As he experimented with some of the data, including sales projections, estimated earnings per model, etc. he put his right hand onto Taylor’s back. She didn’t mind it, even as he started putting one hand on her right shoulder. She looked at the current financial data on-screen and approved. The development of a dedicated fanbase was something she had used to great effect, and she liked how Ryan and the other Victoria’s Secret executives were doing for their brand.

Ryan tried again, “I’d love it if you would pleasure me, Taylor–considering our contract. It’s been some time.”

Taylor responded, “Oh, you. This is a workplace. If that’s what you want. I am available on July 3rd in the evening.”

Ryan took what he had. “Sounds like a good idea. I will await you there. I hope you enjoy that evening and the July 4th party!”

July 3rd Evening

Taylor Swift had arrived to Ryan’s mansion per her contract. She had already eaten dinner, and the trip in the evening would see her pose in a few different outfits before spending the night with him. She had grown to like his skill at pleasuring her despite the age difference. She wore a gorgeous red dress  with a flower pattern on it. Her red lipstick was iconic as usual. Her security team escorted her through the front door of his mansion, where the Victoria’s Secret executive greeted her. It was difficult to avoid the paparazzi, but Ryan had taken a few precautions. Anyway the car used for this trip was unmarked to avoid more suspicion, and every part counts.

“Good evening, Taylor Swift.”
“Good evening, Ryan.”

There was a dressing room in his mansion that had a few outfits for Taylor to try while Ryan and his assistant managed the process. She did not need to do this very often–and it would never interfere with her career. After a few pictures where she posed and smiled for the camera, the process finished.

The Victoria’s Secret executive had finished the financial components of that day and was talking with Taylor about the matter. His job took much of the day, but he still had most evenings available. Taylor Swift, by contrast, had a very busy schedule, with singing, songwriting, touring, and various appearances–such as her new ones at Victoria’s Secret. These were carefully calculated not to interfere with the rest of her busy schedule. There were also a few times where she could meet Ryan more privately, such as now.

He spoke, “Making us your brand has been a great idea, Taylor. Your fans are buying more of our products, and brand loyalty is extremely important.”

She responded, “Thank you, Ryan. I am glad to see that. You have done well to help with touring costs, and after the release of my sixth album, I will trigger the masters ownership clause. That means you will need to help me with getting ownership of my master recordings, which are my life’s work. I’m also enjoying the payout you have given me.”

The Victoria’s Secret executive asked, “Tomorrow will be July 4th. I will host some of the Victoria’s Secret Angels over here, at my mansion. I already have it that you will be attending the party. Some of the executives and agents will be here too. You probably already know about this, but I would love it if you could do a team-up with some of the models.

Taylor thought about it, and said, “Ryan, I could do this. It will be interesting. Who is going to attend?”

Ryan answered, “Martha Hunt, Candice Swanepoel, Jo Skriver, Cara Delevigne, and Lily Aldridge. Martin, Justin, and two agents will be there too. Now let’s get to my favorite part of your contract… you .”

(This is NOT Justin Bieber. This “Justin” is a Victoria’s Secret executive).

The blonde songstress answered, “Sure, we can do all of that. Since I have already eaten dinner, maybe we could spend our night together, and I will join the party. I better have fun.”

Ryan grinned, “You will, Taylor.”

They sashayed over to Ryan’s plush bed, upon which he started disrobing her, to her pleasure. His hands reached to undo her bra and her panties, leaving her gorgeously nude before him. She was a mouthwatering sight. One of the most beautiful singers, now for his personal use for the night and for the party.

She smiled at him and noticed a bulge in his pants. She even shook her ass for him before turning back around and speaking to him.

“It seems you are very ready. Claim your reward, Ryan. You are the most supportive executive I ever had–and you are well-endowed.”

She took off his clothes and they lay down on his bed ready to make out and have a long and enjoyable experience. Taylor smiled at the ceiling then got back up to attend to the executive’s throbbing cock. It had stood up to attention and the blonde singer held it with one of her hands.

As Ryan was lying down and watching, Taylor started licking his cock, enjoying the taste and kissing its tip. She moved down, licking the sides while softly jerking off the Victoria’s Secret executive. After about two minutes, she stopped, only to line up her pussy with his hardened member. It was not long before she bounced up and down on it as he relished the sensation of that perfect pussy. The beautiful songstress had a steady rhythm as she enjoyed the executive’s cock, moaning as she went. There was something appealing about their power dynamic to the both of them.

“Oh this is exactly what I want, Ryan!”

“Keep on going, Taylor! You are most exquisite!”

“Aaah! Ahh!” They moaned as their intercourse went on through the night. The thrusting sounds of Ryan’s cock going up Taylor’s pussy was like music to their ears.

They kept at it, Taylor enjoying the thrusting of Ryan’s cock inside her as Ryan enjoyed the luxurious sensation of Taylor’s pussy and for using such a notable and beautiful lady like Taylor Swift. Swift, for her part, could enjoy herself with him, showing her passionate side without any media intervention. It was not long before the older executive felt himself get very close, as did the young blonde songstress. She was already starting to get wet between her legs

“I’m going to cream inside you, Taylor!”
Ryan released several ropes of cum inside the blonde singer, who climaxed in response. When the last of his white fluid emptied into her magnificent pussy, the two of them settled in bed to sleep for the rest of the night.


In the morning, Taylor woke up first. She whispered to him softly and moved her mouth to his cock. She planted kisses down its length as it hardened in response. After she issued his shaft, she moved to his cockhead and licked it before planting a final kiss on the tip. Ryan felt so lucky that she was serving him.

“Ohh, Taylor. That feels so good.”

She changed her position so that his dick would slide up and down her breasts. This continued for some time as Ryan loved the soft sensation of Taylor attending to him like that. He cooed as he felt the soft squishing of her breasts around his cock. Having Taylor Swift personally pleasure him was such a power move according to the Victoria’s Secret executive.

“Oh… I needed that so much. Your breasts feel lovely around my morning wood. Keep on going.” Ryan thrusted his cock up and down,

His cock pulsed once more, releasing splurts of hot cum all over Taylor Swift’s breasts.

She kissed him on the left cheek before going to clean herself up.

At 9:00 in the morning, the entourage arrived with the executives, agents, and models. It was time for an amazing party!