Escorts, what’s the most peculiar thing a client ever asked you to do?
The Reunion, the Blackmail, and the Emergency
My client’s cousin tried to blackmail me at his family reunion, hinting he’d seen me somewhere before while smirking like he’d already won. When I told him I wouldn’t lie to protect him, he grabbed my arm and said, “You ruined my entire life.”
I just stared at him. That was 9 months ago.
Last week, he was led out of his office in handcuffs while his co-workers watched from the windows.
A client begged me to be his fake girlfriend for an entire day. No intimacy, just pretend to be in love with him at his family reunion.
Apparently, he’d been lying to his family for 6 months about dating someone named Jess. His cousin Derek had been calling him out, demanding to meet this mysterious girlfriend.
I figured I’d eat some free food, tell some madeup stories, and walk away with rent money.
What could possibly go wrong? Well, turns out his cousin Derek was one of my regular clients.
Anyway, he picked me up 5 hours before the reunion and ran me through who Jess was. Jess was the fake girlfriend he’d been playing up for 6 months.
Jess and him met at a bookstore, reaching for the same copy of Murakami’s Norwegian Wood.
She was allergic to shellfish, but loved sushi. She played volleyball in college, and always ordered her coffee with oat milk and two sugars.
The way he’d built this entire person from scratch was actually impressive. The panic in his eyes told me Dererick had pushed him past his breaking point.
When we arrived at his aunt’s house early, I slipped into character immediately.
His mom practically sprinted across the lawn to hug me, tears in her eyes. She said she’d been waiting months to meet the girl who made Dylan so happy.
Within minutes, his uncle dragged us into the family cornhole tournament, insisting we play as a couple.
Dylan was terrible, but every time he missed, I’d pat his back and call him baby. Like we’d practiced, and his family ate it up.
When I scored the winning point, Dylan lifted me up and spun me around while everyone cheered.
His teenage cousin yelled, “Couple goals”. And honestly, we did look good together.
About an hour in, Dylan pulled me aside by the drinks table and whispered, “You’re incredible.” He said, “you know every single thing.” He added, “You’re making me look like the luckiest guy here.”
The genuine gratitude in his voice caught me off guard.
His grandmother cornered us to show me Dylan’s baby photos. She went on about how she’d never seen him smile this much.
She mentioned how I must be the one. Then she added, “Derrick’s almost here,” she mentioned casually.
Dylan’s hand tightened in mine.
The sweetest moment came later when his 5-year-old niece tugged on my dress and asked if Dylan was my prince.
Before I could answer, Dylan scooped her up and said, “Actually, Jess is my princess, and she saved me.”
The little girl made us do a fairy tale kiss. When Dylan leaned in, he whispered, “You’re amazing” against my lips.
His whole family erupted in applause. His mom was sobbing. His dad was filming.
When we pulled apart, Dylan kept looking at me with this soft wonder.
For a moment, I forgot about the money. I forgot about the act. I forgot I had a real name that wasn’t Jess.
Then Dererick walked in. I saw him before he saw me, and my blood went cold.
Dererick was one of my Tuesday regulars, single, cocky. He liked to hire me for overnight sessions where I’d pretend to be whatever fantasy he had that week.
He froze in the doorway, staring at me wrapped in Dylan’s arms. The recognition hit his face like a slap.
Then came that smile, not angry, but absolutely delighted, like Christmas came early.
“Well, well,” Dererick said, strutting over. “You must be the famous Jess”.
He hugged me way too long, whispering, “this is [ __ ] perfect”. When he pulled back, he was practically glowing with excitement.
Dylan didn’t notice, just kept beaming, clapping Derrick on the back. He was saying how he’d finally get to meet the woman he’d been talking about.
Dererick spent the rest of the afternoon orchestrating chaos. “Let’s play couples trivia”.
“Jess, what’s Dylan’s coffee order”? I panicked and said black while Dylan said oat milk latte at the same time.
Derrick howled with laughter. “6 months and she doesn’t know your coffee”.
“Dylan, what’s Jess’s middle name”? Dylan went white.
“Show everyone your favorite photo together”. Neither of us had any.
Dererick made us do a couple’s challenge where we had to answer questions back to back. “Where did you first say I love you”?
We said completely different places. The whole family started looking confused while Dererick kept pushing.
But somehow we survived it. Dylan jumped in with save after save. He made jokes about being bad with anniversaries and me being terrible with photos.
By the time everyone left, we’d barely held it together. Dylan looked exhausted, defeated, his earlier joy completely drained.
When he dropped me off, he kept apologizing for Derek being such an [ __ ] and thanking me for pushing through.
I didn’t have the heart to tell him that Dererick knew exactly who I was. The guy looked so crushed already.
I figured that was the end of it. Then I woke up the next morning to 16 missed calls from Dylan.
Texts were in all caps: “Need you now”. “Emergency”. “Please answer”.
I called him back immediately and he answered before the first ring even finished. He was talking so fast I could barely understand him.
It was something about Derek, a family dinner, and his mom crying. I had to tell him to slow down and start from the beginning.
20 minutes later, he picked me up in his Tesla, his hands shaking.
He explained that Dererick had called his parents that morning, suggesting they throw a special dinner tomorrow night. This was to celebrate me joining the family.
His mom had already invited 30 people, including his grandmother, who was flying in from Houston.
Dererick had specifically requested that I wear the same dress from the reunion. This was so everyone could see how beautiful Dylan’s girlfriend looked in photos.
Dylan parked outside a Starbucks, and we went inside. He pulled out his phone to show me the family group chat that Dererick had started.
The chat was filled with excited messages about finally getting to know me better. Dererick’s message at the top said he wanted to make up for being difficult at the reunion by hosting the dinner at his house.
He even offered to cater it from that expensive steakhouse downtown.
Then Dylan’s phone rang, and when he saw it was Dererick, his face went white. He answered it on speaker anyway.
Dererick’s voice came through smooth and friendly. He asked if we’d gotten the dinner invitation.
He said his mom was already planning the seating arrangements to make sure we sat at the main table with the grandparents.
He mentioned how excited everyone was to hear more about our love story. This was especially true after some family members had questions about how well we really knew each other at the reunion.
The threat was so obvious I felt sick.
Dererick added that he’d love to hear about where I worked and what I did for a living. Dylan’s hand found mine under the table and squeezed hard.
After Dylan hung up, he turned to me with this desperate look. He said he’d pay me triple my usual rate if I’d help him figure out how to handle Dererick without his family getting hurt.
I realized right then that I wasn’t just playing a fake girlfriend anymore. I was basically hired as damage control for whatever Dererick was planning.
We stayed at that Starbucks for 3 hours while Dylan showed me Dererick’s social media accounts on his laptop.
I scrolled through years of posts where Dererick had systematically destroyed other family members. He did this while looking like the concerned cousin.
There was his cousin Jennifer whose OnlyFans account got exposed at Thanksgiving. His cousin Michael’s DUI arrest somehow made it into the church newsletter.
His own sister Natalie’s miscarriage became family gossip after Dererick accidentally let it slip at Easter brunch.
Dylan explained that Dererick had been doing this for years, always maintaining plausible deniability. He positioned himself as the responsible eldest grandson who just happened to be present when family scandals erupted.
The worst part was learning that Dererick had access to their grandmother’s will revision meetings. He drove her to her lawyer appointments every month.
The inheritance was substantial enough that Dererick had been systematically eliminating competition for years.
Dylan showed me a spreadsheet he’d been keeping of every family member Dererick had targeted. The timeline always matched when those relatives had gotten close to their grandmother or achieved something significant.
My phone buzzed, and when I saw it was my agency calling, my stomach dropped. They never called unless there was a serious problem.
The woman said they’d received a concerning call about me potentially violating client confidentiality. This involved discussing private session details with third parties.
While they couldn’t reveal who made the complaint, they needed me to come in within 48 hours to discuss this serious allegation.
Dererick was already applying pressure, but being careful not to leave evidence. The agency woman’s tone made it clear that my entire career was now at risk.
I was still processing this when Sophia walked into the Starbucks like it was a total coincidence. The way she headed straight for our booth made it obvious Dererick had sent her.
She slid in next to Dylan with her phone already out, live streaming to her 50,000 followers. She gushed about randomly running into her favorite cousin and his gorgeous girlfriend.
We were trapped into performing for her audience while she asked increasingly specific questions about our relationship. Her followers were commenting in real time with hearts and questions about when we were getting engaged.
Sophia kept pushing for details about how we met, where our first date was, and what my favorite thing about Dylan was. I watched her screenshot specific moments when our answers didn’t quite match up.
Dylan tried to deflect by talking about how bad he was with dates and details. Sophia just laughed and said her followers loved getting to know authentic couples who weren’t perfect.
She stayed for an hour, her phone never leaving her hand. She was building a digital trail of inconsistencies that Dererick could use whenever he wanted.
