"Tell me, Cin. How do you decide? You know, which girls who come to you for help get the chance and are allowed to escort?"
The pair were in Lennie's living room. He was on his laptop, and she was reading her Kindle. She thought about the question and how sincerely Lennie had proposed it. She could tell it meant a lot to him, but she couldn't understand why. "It's best to just be honest with him," Cindy thought. It has worked for her so far during those rare times she couldn't read him.
"You mean, why do women want to escort? It's determined by them. Some need more money than any regular job would pay. Others aren't able to work the standard 40 hours. They just aren't; they bounce from job to job because they can't stay at a desk or can't be around the same people for too long. And some are completely unique. They are sexual beings who are always thinking of sex and are being reminded of it by every man and woman around them. Those women are safe to be whores because, deep down inside, it is what they want. Each girl is different, and there is no way to figure out if a girl wants to be in the game or not."
"Well, thanks for that, but no, that's now what I meant. I mean, how do you make the final decision on who to hire? You said so many women contact you, and many even go on practice dates to prove they can do it. Even then, most don't make the final cut."
"Oh, I understand now. They date some of my long-term regulars, guys that I know and who are honest with me about the girl's performance. They kind of have an unwritten checklist for the girl being evaluated. It's not just if they do the basic positions or how they can suck cock, but stuff like how do they make the client feel? Are they warm and friendly, or standoffish and formal? Does the girl give the client that 'warm and fuzzy' feeling, like they really care? It's partially grading on how well they perform the sex acts, but is there also something extra that makes her stand out? Does that make sense?"
"Yeah, it makes a lot of sense. All of your girls have that 'something extra' in spades, you know?"
"I'm glad you've noticed, Lennie." A new thought entered Cindy's mind.
****
The next day, Cindy approached Lennie with a request.
"Lennie, I would like you to help me."
"Sure, baby. What is it?"
"One of the housewives has decided she has earned enough money and is going to retire. I need to choose a new girl to replace her, and I want YOU to decide who it will be."
Lennie grinned. Choosing a new woman who wants to be an escort, working for Cindy? What a delicious thought! At first, he thought that she was kidding. But she was completely serious.
"Lennie, I have it down to two girls as the replacement. She will be working under me to show her the ropes. Both girls have had three working encounters and passed all the tests. They will do anything my clients expect of them. But I need a man's perspective whom I know well. Before, I used one of my regulars for their manly perspective, but now that you are my pimp, that job will be yours from now on. I want you to date each one as if you were a client and tell me which one I should hire."
Lennie grinned at her with a big smile. This was going to be good.
"Think of this as a business task. You are not only my boyfriend, but you are also my pimp. I want, no, need to have my pimp make my decisions for me, and that includes which woman gets added to your stable."
Stable? That phrase was mind-numbing when Cindy used it. Even if it were true, it most certainly didn't describe any reality, at least until the last few months when Lennie's world changed.
"Okay, Cindy, what do I do?"
"The two girls are Leslie and Shauna. Both have had three appointments so far with regulars, and both have graded out well. Either could work well for the escort service, but the way we are set up, there is only one job opening. So I want you to take each one on a date and then decide who you want to work for us. It is now your stable of women, so it's your call."
"What criteria should I use, Cindy?"
"Anything you want. Both girls have checked the required boxes on what the escort service needs. Try to decide which girl will fit in best with the rest of your girls. And also, which one gives you a stronger "warm and fuzzy" feeling like we were talking about a couple of days ago?"
"
My girls?
" Lennie thought. As if Cindy were reading his mind, she said, "Yes, I said your girls. Because it's true. They go out and fuck strangers the service sets them up with, and they come home and give us a third of the money they earn. I am what they call in the game your "bottom bitch," the girl that manages the day-to-day workings of all your girls." She smiled and stared into his eyes. "I feel so content that I have a pimp who loves me. I'm so proud to give my pimp this multi-million dollar business and all the girls that come with it." Lennie kissed her with a sloppy wet tongue, and she returned the wet kiss with a similar force. He hugged her tight.
"I love you, Lennie."
"I love you, Cindy."
Cindy held up her phone and showed Lennie a picture of a beautiful woman, then another one. She showed him a half-dozen poses of each in business wear, their underwear, and fully nude.
"Which one do you want first?"
Leslie was about 5'3", a strawberry blonde with shoulder-length hair. Her face was gorgeous, and her smile was intoxicating. Her boobs were probably a B cup, but they fit her slim, athletic body in perfect balance with the rest of her curves. Two words that came to mind for Lennie were "pixie" and "perky".
Shauna was a mulatto woman who was tall and had light-brown skin. She was also athletic and had larger breasts and hips that were not too big. Her thighs were curvy yet slender. The curves on the cheeks of her ass were amazing. Her heritage came from both her African father and her European mother. Her body and facial features reminded Lennie more of a white woman than the light-skinned black woman she was. Not only that, but her hair was long, black as night, and straight with a gentle curl instead of tight and frizzy like many African women's. It was the smoky, sexy look emanating from her eyes that caught Lennie's attention.
"So, only one?" Lennie already thought that this was going to be a tough decision, and he hadn't even met either one yet.
"Yeah, I know. I like them both. It is so hard to choose sometimes. Well, now we are giving them the economic break of a lifetime. Nowhere else can they make an hourly rate and get tips like our escort service offers. You will date them both and select one of them. Then, the final step is to break the news of their new job offer to their husband. He has to buy it or it's off. You don't have to be there to talk with the husband. That's my job."
The next evening, Lennie entered the Grand Sheraton downtown and walked to the main seating area in the large open foyer. A gas fireplace was burning as people sat around in the oversized chairs and the long couches as a waitress brought them drinks. As he turned to his right and towards the fireplace, a beautiful light-skinned black woman in a tight, dark red dress that highlighted her feminine curves turned and smiled at him.
"Shauna?"
"Lennie? Good to meet you!" She got up and reached around him as she brought her mouth to his. Kissing him slowly and sensuously, she melted her large breasts into his chest. Lenny inhaled and caught her intoxicating smell as she leaned in and whispered in his ear.
"Take all you like, Lennie. I'm here for you."
Lennie smiled. He knew she was on her best (or was it her worst?) behavior. Was she one of the most beautiful black women he had ever seen, or was she one of the most beautiful women he had seen who just happened to be black? A distinction without a difference, Lennie decided.
"Before we go upstairs, let's have a drink and get to know each other. Okay?" Lennie smiled as he made the offer. She was truly beautiful.
Having arrived early, she had a second Cosmo, and he had a Buffalo Trace whiskey on the rocks as they sat down on the long, thick couch beside each other.
"So, Shauna, tell me about yourself. And why do you want to work for the service?"
"Lennie, I've known of Samantha's Escort Service for a few years now. A friend of mine used to work for her a few years back, until she met her man, got married, and retired. We had worked for an expensive escort service together in Southern California when we both went to UCLA. It was how we paid for school. I'm not new to the business. I got hired by a Fortune 500 company as a marketing manager, and about five years later I got married. Ironically, my husband always called me his little slut, his little whore, even though he had no idea I did that to pay for school.
"I was insatiable, demanding, and getting wild sex from him nearly every night. A year ago, my husband was badly injured in an auto accident. I had to leave work to tend to him after he got out of the hospital. One thing I lost was that he couldn't perform for me because his back and hip were broken. One of his hips was shattered, and it took three surgeries to get it to start healing properly. Over a year later, he was finally able to mount me, but the sex has been a shadow of what it was. He gets hard, but he has no body strength to pound me like a man should. I can't ride him because his pelvis is still healing, and if I came down too hard on him, it could break again. More importantly, his long recuperation was only partially covered by insurance. We have had our finances drained for so long now that they are nearly gone."
