Colby Jack
Copyright© 2026 by OmegaPet-58
Chapter 2
Fiction Sex Story: Chapter 2 - [1/20 Now 6 chapters] Jack Colby is eating breakfast in a Miami hotel restaurant when a dispute between an elegant woman and a boor disturbs him. She's done with their commercial arrangement, he doesn't want to hear it, and before he can get violent, Jack intervenes and chases him off. Impulsively, Jack offers Renée a new deal which becomes a GFE, three letters new to him. He's skillful in bed, but lonely, surprising her.
Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa Fa/Fa Consensual Lesbian Heterosexual Fiction Anal Sex Masturbation Oral Sex Sex Toys Prostitution
Jack Colby left the terminal and stepped into my limousine as Carter Duke Burleigh IV—the ridiculously wealthy inheritor of an accumulated fortune, some of it rooted in the tobacco business.
In the limo with me were my driver, Martin, and my bodyguard, Gray. These were men I knew well from years in those positions. My greeting to them this time was curt and distracted, causing the two of them to exchange glances and skip the “How was your trip?” small talk.
After we floated onto the interstate, I asked, “You guys hungry?” They admitted they were, so I picked up the phone and called the kitchen.
“Hello, it’s Carter. Can you set me up with a lunch, just soup and a sandwich. And when we arrive in—”
“Forty minutes,” supplied Martin.
“Forty minutes, get my two guys here what they want. Yeah. Thanks, Lorraine.”
Even while flying in first class, I’d learned to distrust the airline meals.
I closed my eyes and let my head fall back. I’d revealed so much to Ren, only to learn she was playing a role. It left a bitter taste.
Was it all acting? I didn’t think so. If I hadn’t affected her, I wouldn’t have seen those flashes of real emotion. At least, I had her phone number. If we met again, I could learn more.
It was the night after I returned from Miami. About 9 o’clock, I padded down to the kitchen looking for a snack; but Lorraine was still in there tidying up.
“Sorry, I was just looking for a snack.”
“Sure, Boss, I’ve got some cheese and crackers. And there’s some wine, it will help you sleep.”
I looked up at her well-lined face. Lorraine was grandmotherly; she managed to keep slim despite her line of work.
“You can tell?”
“Your face shows you’re not resting well.” She put a half-full wine glass in front of me. “Why don’t you tell your bartender what’s bothering you?”
“You wouldn’t understand.”
“My youngest is your age, Boss. There’s nothing you can say that I won’t understand. It’s not a woman; you never go out.”
I stared down at the plate.
“Wait, someone in Miami? Come on. Tell me.”
“Yeah, it was a woman in Miami. I was getting all excited and interested and things seemed to be going well, and then she said she wasn’t serious and left.”
“And this is bad because...”
“I blame myself. I’m not good with women.”
“She didn’t know you were wealthy.”
“That’s right.”
“Listen, suppose she did string you along and played with your feelings, then dumped you. Wouldn’t that be worse?”
“I guess so.”
“I know so. The only way out of this for you is practice. You need to be going out more, meeting more people. I’d date you myself, but I already have a job and my husband isn’t good at sharing.”
“Aw, Lorraine, I hope he appreciates you.”
“He does, and I’m late getting home to him. You think about what I said, Carter.”
I slipped into my usual routine. Part of that was the lap swimming, which I cranked up from twenty to thirty daily laps. Ren had seen a little more of my gut than I wanted to show. I blamed Lorraine, whose kitchen achievements never failed to impress me.
At night in my bedroom, my thoughts kept circling back to my hours with Ren. On an intellectual level, I knew we didn’t have a relationship with a future. And yet, in my fantasies, Ren was throwing herself into my arms and promising her lifelong love and devotion.
In the afternoons, I used my home gym equipment with my physical therapist, Ellie. She spotted me while lifting weights, corrected my gait and movements, and massaged out the stiffness.
Several days after I returned from Miami, I went through my usual routine with Ellie. Before she left, though, she had questions for me.
“You’ve been overdoing everything these past days. Instead of fifteen presses, you’re doing thirty. You’ve switched to the heavier kettlebell. I could go on. What’s going on?”
“Nothing. Well, something—you could call it a romantic failure.”
“You went out with a blind woman?”
“No, what do you mean?”
“Considering all the men I’ve had as clients, your body is in the best shape. I have to confess, keeping things professional between us has been a struggle.”
“You’re attracted to me?”
“Having normal vision, yes I am. Not that I would do anything about it.”
“I sensed your interest, but I didn’t worry.”
“What gave me away, Mr. Burleigh?”
“Many times, I’ve told you: call me Carter. I overheard you call home, and your tone was very loving. I would never intrude on a marriage. I want you to continue as you have been.”
“Thank you, Carter. I appreciate that you are being respectful.”
“I’ll see you tomorrow, Ellie.”
She took a few steps, then whirled around and faced me.
“No. I’m making a decision to revise your program. One thing I’m sure about: in all the time we’ve worked together, you haven’t been dating or had a girlfriend. I’m helping polish your body to near perfection and you’re withholding it from the women of the world. Carter, tomorrow I’m bringing with me my wife, LC. She’s going to be practicing conversation with you while I’m working on your body.”
“Your wife’s name is Elsie?”
“No. Her initials are L and C—just like mine are L and E. The first thing you two can talk about tomorrow is why your first question about this arrangement is about her name. Not about why I’m volunteering my beloved wife as your instructor in the arts of love and conversation.”
“So, why are...”
“Tomorrow, I said. You’re going to pay her along with me. She has time because where she teaches is on summer break.”
“So, she’s a...”
“Tomorrow, I said. You need to work on listening, don’t you?”
“Sorry, LE.”
“Better. We’ll both be here at the regular time, Carter.”
The next morning, I was so nervous I swam an extra ten laps, and then powered down two sandwiches at lunch.
I greeted LC and LE at the door, asking them to step inside.
“Aren’t you a tall drink of water?” LC looked me up and down. Both of them were typical height for women, about five-foot-four. LE was wearing her usual hospital scrubs, while her wife wore a polo and slacks. Both women had curly brown hair, brown eyes, and slim builds.
“Yeah, I’m six-foot-six.”
LC made a noise, like a game show’s error buzzer. “You’re off to a bad start, Carter. A tall guy like you should have a library of funny remarks. Like, ‘I have to duck when geese fly by,’ or ‘I have to register with air traffic control,’ or ‘door frames are my natural predator.’”
“Oops.”
“Let’s try this again. I say, ‘Aren’t you a tall drink,’ and you say—”
“I should not have eaten those magic beans.”
They both laughed, so I might be on the right track.
“I told you, LC, my client has potential. I’ll work on his body while you exercise his mind.”
She eyed me up and down again. “LE, how about we trade? I’ll run my hands over his buns while you trade witticisms.”
“Carter, do you see what I’m talking about? She hasn’t even seen you topless yet.”
LC fanned her face with her flattened hand. “Oh, my...”
I left them in the gym and went to my bedroom, returning in a jockstrap and athletic shorts.
“I’m ready for my punishment, LE.”
“Punishment? I haven’t even started. I know you’ve been to college. Every time you say something nerdy or stupid to my wife, you’re going to feel my elbow. Get it?”
This was the first of many “joint sessions”—a phrase I use intentionally. One of them worked my body while the other worked my conversation. Along the way, my small talk improved, my posture relaxed, and my coaches’ affection for each other was impossible to miss.
I got suspicious when LE pulled my shorts down to massage my “glutes,” a process which ended abruptly. When I turned to look backward, both of them were eyeing each other as if they were about to kiss. I pulled my shorts back up and growled at them. At least they had the grace to look abashed and apologize.
“You two letter girls are awfully bad at being lesbians, the way you undress me with your eyes. Quit it!”
Overall, I could tell that my skills at being more relaxed and making ordinary conversation had improved. I learned a lot of details about my coaches’ relationship, including how they met and how they courted. They were in their fourth year together and still in love. I had to congratulate them.
After a week of double coaching, LC had a new plan for me. I thought it was brilliant. Tuesday night, I would take her to dinner as my “date,” with LE as a silent chaperone making notes. Wednesday, we would review the date, and then Thursday LE would be my “date” for a Friday review with LC’s notes. They reminded me to choose an ordinary restaurant where I wouldn’t be noticed or stand out.
I’d like to think I did well. With positive feedback from my “dates,” we agreed to repeat the plan the next week.
When the agreed time came (three weeks after visiting Miami) for my call to Renée, I felt more confident.
“Hello?”
“Ren, it’s Jack Colby. How are you?”
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