The Agency Ch. 21 (Retreat Pt. 02)

The Retreat was part work and part vacation. For a few hours every day, all of the associates gathered in the auditorium to listen to a lecture that was supposed to benefit our work. The lectures ranged from, "Edging- The Power of Orgasm Control" to "Multitasking- The Art of Satisfying Multiple Partners" to "Massaging Egos- How to Fondle a Celebrities Most Important Asset". Each lecture offered a few good pieces of knowledge, but was overall not very enjoyable.

Thankfully, we only spent around three hours each day in lectures, which left us more than enough time to enjoy the resort. The resort was top of the line, offering lots of amenities, including: spa, boat rentals, Jet Ski rentals, scuba lessons, tennis, golf and so much more.

Once the lectures were over for the day, Michael, Jake, Erin, Lauren, Samantha and I would explore one of the features offered at the resort. It was fun getting to relax at the spa and zip around the ocean on a Jet Ski; but the best part was getting to hang out with new friends.

After dinner, we would break off into couples, which would allow me time to hang out with my favorite person in the group, Samantha. I was still a little confused about what our relationship status technically was, but I was enjoying the relationship that had formed.

I spent hardly any time in my room that first week, with the exception of showering and changing clothes. At nights, I stayed with Samantha. Due to the nature of our jobs, our sexual encounters didn't last very long. With having to constantly perform sexually, we used the opportunity to enjoy more of an emotional connection than trying to have hours of mind-blowing sex.

Don't get me wrong, Samantha was incredible in bed. The technique she had, coupled with her incredibly sexy body, rocked me every night. The difference was that we were building something bigger than just sex. Sex was secondary to the relationship we were forming, which was incredibly refreshing given the nature of our work.

The associate-only portion of The Retreat came to a close with a big party, after the owner's Closing Speech. Our group stayed together during the party, with the occasional associate coming by and exchanging pleasantries.

"This part of The Retreat always flies by so fast!" Erin said, with exasperation in her voice, "I enjoy the next few weeks, but I hate that our time together is so short."

"Yeah, tomorrow the work actually begins. I've already looked at my schedule and I'm going to be exhausted this time tomorrow," Jake added.

I hadn't given much thought to what would happen when the celebrities came to visit, as I had been enjoying my time with the group and Samantha too much.

"How exactly does this next part work?" I asked.

Lauren pulled out her phone and said, "You have to download the "My Agency Retreat" app and sign in to your account. There will be a calendar that pops up, which will show you who has booked you and for how long. The celebrities will show up at your door at the given time and you will do your thing. If it is someone you haven't been with before, the app will also give you a bio on the celebrity so you can prepare for your meeting."

"So, will we be booked for just a few hours a day and have the rest of the time to hang out with each other?" I asked.

Erin laughed, "Well, I don't know about you, but I know that I am booked solid. The little free time that I will get, I'll be resting for my next job."

"With you being new they'll likely give you a slightly lighter load, but most celebrities will sign up for at least a few hours with you. That doesn't mean they expect the sex to last that long, but it will give you plenty of time to spend with the celebrities doing whatever you want," Jake added.

"You mean you all don't have sex the whole time?" Michael chuckled, as if he was impressed with his prowess in the bedroom.

I downloaded the app to my phone and logged into my account. My first day only had two clients scheduled, but they had me scheduled for pretty much the entire day. My first appointment started at 10am with Taylor Swift, and my second was with Ariel Winter.

I was excited to see Taylor and Ariel again, as they were two of my favorite clients; but I was a little sad that this would be the end of all the time hanging with the group. I was especially sad that my time with Samantha would be gone.

The party began to wind down and I took the opportunity to sneak away to the beach with Samantha. The beach was brightly lit by the full moon, which reflected off the water and made the white sand glow. Samantha and I walked down the shore line.

"I guess it didn't hit me until tonight that our time together was going to end so quickly," I said.

"I realized it, but I just tried to ignore it," Samantha responded, as she reached down and gripped my hand, "I didn't want to have to be away from you, but that is how our jobs work."

"I'm not sure how exactly you'd characterize our relationship, but I want you to know that I think of you as my girlfriend. I really hope that even when we get back home and back to travelling with work that we can stay in touch and get together whenever possible. It may be complicated at first, but I hope that it is something that can work out, because I really like you!"

"I like you a lot too! I was hoping that you'd want to keep this going past this retreat. I've never had a boyfriend while working for The Agency; but I think if anyone can make it work, it would be us."

We made our way back to Samantha's room. For the first night, we wouldn't have sex together. We decided that since work would be picking back up, it would be best to try and save some of our sexual energy, but that didn't prevent us from being affectionate.

Samantha climbed into bed wearing a sexy black bra and panty, which showed off the beautiful color of her alabaster skin and red hair. We spent the entire night wrapped up together, our bodies connected by more than the skin on skin touch. It was as if our hearts came together as we lie together in bed. We kissed and ran our hands over each other's bodies, as if we were building a mental image to take with us until we were back together.

The next morning, I said my goodbyes and headed back to my room. This was the first time all trip that I had spent more than an hour inside my room, as most of the trip had been spent out and about, or in Samantha's room. I pulled up the app on my phone to review my schedule for the upcoming week. The list was full of familiar names, but also included a few people I had never been with.

My Week One Schedule:

Day 1

• Taylor Swift (10:00 am- 4:00 pm)

• Ariel Winter (6:00 pm- 7:30 am)

Day 2

• Jennifer Lawrence (12:00 pm- 8:30 pm)

• Taylor Swift (11:00 pm- 9:00 am)

Day 3

• Kat Dennings (1:00 pm-4:00 pm)

• Ariel Winter (7:00 pm- 7:30 am)

Day 4

• Amy Adams (9:00 am- 12:00 pm)

• Selena Gomez (2:00 pm- 5:00 pm)

• Ariana Grande (7:00 pm- 10:00 pm)

Day 5

• Recovery Day

Day 6

• Taylor Swift (10:00 am- 9:00 am)

Day 7

• Ariel Winter (12:00 pm- 6:00 pm)

• Jennifer Lawrence (9:00 pm- 3:00 am)

I was glad to see some familiar faces on the schedule. It appeared that there would be a few overnight appointments with both Taylor and Ariel, but unsurprising to me Jennifer elected no to have one. She hadn't been keen on sleeping in the same bed as me when we were in Jamaica, why would she start now?

Four new names stood out on the list, as it appeared a few new women would be giving me a test drive. Day 4 needed to be a good day performance-wise, as I would need to impress three potential clients. I had heard of all four new celebrities, but decided to go to their profile to learn a little more about them.

Kat Dennings

Age- 29

Height- 5'3"

Hair Color- Dark Brown

Eye Color- Blue

Measurements- 37-27-35

Bra Size- 34DD

Sexual Experience- Moderate

*

Amy Adams

Age- 41

Height- 5'4"

Hair Color- Red

Eye Color- Blue

Measurements- 34-25-34

Bra Size- 32B

Sexual Experience- Veteran

*

Selena Gomez

Age- 23

Height- 5'5"

Hair Color- Dark Brown

Eye Color- Brown

Measurements- 34-24-33

Bra Size- 32B

Sexual Experience- Limited to Mild

*

Ariana Grande

Age- 22

Height- 5'0"

Hair Color- Brown w/ Blonde Highlights

Eye Color- Brown

Measurements- 32-24-32

Bra Size- 32A

Sexual Experience- Mild to Moderate

*

It was quite a spread of women that awaited me in the next week. 7 women in 7 days would be a new experience for me. In all of my prior assignments, I had gotten to be with one celebrity for at least a few weeks, which allowed me time to get to know them and learn what they liked and disliked sexually. Instead, this "Customer Appreciation" was going to be rapid fire. I would have a few hours to try to provide good service to my current clients and prospective clients.

The clock read 9:58 am, when I heard a knock on my door. When I opened it, I found Taylor eagerly waiting to come inside.

"You're early," I barked, pointing at my watch.

"I figured you wouldn't mind," Taylor replied, surprised at my anger for her being 2 minutes early.

"I'm just playing," I said with a laugh, opening the door for her to come inside.

This was the first time I had seen Taylor since she slipped out of my apartment, causing a firestorm that nearly cost me my job. I was excited to finally be back with Taylor again, as she had been my first and possibly favorite client, but there were definitely some things that needed to be talked about before we could get to the fun stuff.

Taylor took a seat on my couch and I joined, sitting on the cushion beside her.

"First of all, I want to apologize for the mess that I caused the last time we were together," Taylor said, "I know that based on the tone that Eliza had when she called me that she was mad. I hope I didn't cause you too much trouble."

"Oh, she was mad," I said with a little chuckle, "but I fortunately didn't lose my job. Things still aren't back to normal between Eliza and me, but hopefully that will change over time. I don't regret our night together though."

"Well, I was glad that it didn't get you fired. I really never meant any harm by my visit, just missed you. I figured when we got in trouble, it would be best to allow there to be some time to cool off. My mom had wanted to ride the tour bus with me for quite some time, so I figured I'd give her the opportunity this time around. I'm not sure if Eliza would have let you come even if I had requested it, but I knew it was probably best to wait."

"I understand. I was actually really excited to hear about this retreat, because I figured I might get to see you again. I was disappointed to miss out on a tour with you, but we will get a few opportunities this week to make up for that."

"How about we go ahead and get started?" Taylor said with a wink.

We made our way to my bedroom and Taylor pushed me back onto the bed. As Taylor worked off my shorts and underwear, I removed my shirt. In a matter of seconds I was lying naked on my bed, staring up at Taylor.

Taylor was less speedy with removing her clothes, as if she knew I enjoyed the show. She slowly peeled off her shirt and high-waisted khaki shorts.

"I bought these special for you," Taylor said, as she revealed a bright yellow bra and panty, which were trimmed in black, making the yellow pop even more.

"Mmm, I think they are sexy!"

"You want me to keep them on?"

"How about you just leave the bra on? I need the panties out of the way for other plans I have in mind."

Taylor smiled and slipped off the panties before climbing onto the bed. She straddled herself above me and grabbed my hard cock, rubbing it along her clean shaven slit. Taylor was already a little wet as some of her juices moistened the tip of my dick. Taylor finally pushed my cock down to the bottom of her slit and dropped her hips down, allowing me to slip inside her.

We both let out a relaxed moan. It was as if we had been yearning for this moment, and were finally at peace being back with each other. I lifted my hips and grabbed on to Taylor's hips, rocking them back and forth. Taylor brushed the hair away from her face as she let out restrained moans and gasps.

I'm not sure if Taylor hadn't had sex in a while or not, but it took her very little time to climax. The restrained moans and gasps had broken out into screams as the orgasm sent shock waves through her body. I grasped Taylor's shoulders and pushed her down onto my hips, allowing my cock to press as deeply inside her as it could. This seemed to prolong Taylor's pleasure.

I hadn't finished yet, but Taylor seemed exhausted from this quick orgasm. We decided to take a break and give her time to recover. We had six hours together, which was more than enough time to go at it another time or two.

Taylor walked out my door at 4:00 pm, happy and exhausted. We made up for lost time, as we went at it three times in our six hours together. The experience had been tiring, but I knew I needed to rebound, because Ariel wasn't far behind.

Room service arrived not long after Taylor departed, and the large meal gave me some additional energy. I made sure to shower off, as housekeeping came to change out the sheets so things we be fresh for Ariel's visit. It was a lot to cram in during only a two hour break, but somehow everything got done. I was ready and waiting when Ariel knocked on my door at 6.

I had barely had the opportunity to open the door before Ariel had run in and jumped into my arms.

"Oh my goodness! I missed you so much!" Ariel screamed as she hugged me and gave me a few quick kisses on the cheek.

The relationship I had with Ariel was different from any of my other clients. Ariel, as you remember, lost her virginity to me just a few months prior in New York City. We had turned a very uncomfortable start into a very caring and tender relationship. I was the only man that had been with her, and I knew that made our relationship that much more important.

We were scheduled for an overnight appointment, and Ariel knew she had plenty of time to catch up later. We had hardly had the opportunity to say hello, before she took off to the bedroom, leaving a trail of clothes in her wake.

When I finally caught up to Ariel, she was sprawled out on the bed, ready to go. I hadn't expected to jump into the sex so quickly, but the sight of Ariel ready and willing made me rock hard. I stripped down and lay on top of her, kissing every inch of her naked body.

There is something different about being with someone who is inexperienced. People who have experience sexually, tend to want to jump straight into sex and forget how nice everything else can be. Ariel wasn't jaded to sex. She appreciated the feeling of my lips running across her belly, the squeeze of my hand on her large bare breast and the feeling of my cock dripping pre-cum on her body as it skimmed along her skin.

I had far more difficulty pacing myself with Ariel then I had with any other client. While it normally didn't take too much to get her to orgasm, her tight pussy caused me to cum much quicker as well. We started in doggie style as I pounded her from behind, grasping onto her long black hair, as my hips clapped against hers.

I quickly brought Ariel to orgasm, as she let out a powerful yelp. The second orgasm was not far behind as I continued to pound her tight pussy.

"I want to you to titty fuck me!" Ariel screamed as another orgasm hit her.

I pulled out, cock soaked, as Ariel made her way to the side of the bed. She got on her knees and faced me as I sat on the edge of the bed. My cock was super sensitive from how tight she had been. I knew that I wouldn't last much longer.

Ariel positioned my cock in between her breasts and began to slide her breasts up and down on my cock. Ariel's breasts were very soft, which felt great; but didn't apply much friction to my lubricated dick. Fortunately, I was very sensitive, so even the little amount of feeling that it caused was magnified. Ariel stared at the tip of my dick as it popped in and out of her cleavage.

I couldn't help but think back on the shy girl I had met just a few months before in New York. To think that she had not only let me be her first, but now she was stroking my cock with her breasts. Ariel had become my little slut who was hungry and eager to explore her sexuality. This thought, along with the visual of my cock rubbing between those boobs was all I could take.

My tip sprung out of the top of her cleavage and shot a giant spurt that hit Ariel in the cheek. She was a little caught off guard, but was excited to have made me cum. She pulled my cock out from between her breasts as it continued to shoot my load onto her tits. Ariel stroked my dick urging more to come out, as her breasts began to be covered in long strands of my cum.

When my final shot squirted, I sat back to admire the sexiness that sat in front of me. This beautiful innocent girl, sat with my dick in her hand, showing off her gorgeous body, which was now covered with my sweet cum. Ariel smiled up at me and sucked the little bit of cum that was oozing out of my tip.

Ariel cleaned up and we had the time to sit together and catch up. We spent most of the night talking before we finally fell asleep in my bed.

Ariel departed early the next morning, but was excited that she would get to see me in another day. I took a few moments to savor the time I had with Ariel before I refocused to Jennifer. It had been a long time since I had been with Jennifer, but we still spent some time sending each other dirty pictures and videos on our phones, through the app we were provided in Jamaica.

Much like Ariel, Jennifer came in all business, ready to go to town. Jennifer insisted that we set up a camera to film our sex, as she was still very much into capturing our time together. I guess she had grown tired of the videos we had filmed in Jamaica.

Jennifer held nothing back in the bedroom. Screams, moans and yelps echoed throughout the room as Jennifer rode me and had her way with me in a variety of positions. I imagined that some of her enthusiasm was for the camera, but she also seemed very into the sex itself. Regardless, it was incredibly hot to watch her enjoy me again.

Taylor came over later that night and stayed the night with me, which was nice. We had sex once while she was there and it was relatively quick, albeit very satisfying. Most of the night, we spent in bed just talking and relaxing, much like we had done on that very first tour together. I had forgotten how great our friendship had become.

"I don't know if you have seen, but my friend Selena is supposed to be scheduled with you at some time this week," Taylor said as she lay on my chest.

"Yeah, I saw later in the week she is coming."

"I recommended you to her, not long after our tour together. She had originally been assigned someone else, and she said the sex was good; but she was hoping to find something more satisfying, both sexually and as a friend. I'm hoping you two hit it off. Maybe we could hire you at the same time if she likes you."

My mind began to wander and daydream at this thought. Taylor and Selena together seemed very hot, especially after how great the threesome with Taylor had been before. This added some pressure to an already important visit, but gave me even more motivation to perform well.