Lennie And Samantha Ch 14

"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."

Lennie already felt something for this beautiful woman.

"My husband didn't know I was an escort until after we got married. I didn't think it was any business of his, because I decided to quit long before we met. Then, after everything, I told him because I knew my marketing job wouldn't have been enough to pay our bills. After all, he couldn't work, and my salary alone wasn't enough. So I told him what I used to do. He didn't speak to me for a week, but later, he started opening up, and now we have come to an agreement of sorts. As long as I keep quiet about it to people we know, he will let me continue."

"Wow, just like that?"

"He has made the comment that I've already been a whore, and he lived with it even though he was in the dark, and he realizes that I am doing it for us, for him. And he felt guilty that he couldn't give me the wild sex we used to have. My husband told me that he didn't prefer my planning to whore myself out again, but he would accept it. He said he wondered how I could go without for so long. I told him the truth: it was tough, but I love him so much."

They finished their drinks and went to the room. Lennie watched as she slowly stripped, and her dress fell to the carpet. Her big ebony breasts were flawless for a twenty-eight-year-old woman. They moved to the bed, Lennie fondling her breasts as he laid her down. She dropped to her knees and, in between his, started sucking his hardening cock down to the bottom of her throat.

The slobbering on his cock and balls was impressive. Her shaven pussy slit glistened with moisture as he slowly rubbed two fingers inside and out of her wet pussy. He looked down and saw a huge pink clit sticking out from underneath a hood. It was almost like a small penis; it was so big.

"Do you like my pussy, Lennie? Do you like my big clit? It wants you to touch it, Lennie. Rub my clit, baby. Use me; use my body for your pleasure. It's yours. Fuck me like your bitch, Lennie. I'm your bitch. Fuck me like the bitch whore I am!"

Lennie was jamming his fingers in and out of her pussy, glancing off the side of her clit haphazardly. She anticipated the tingly feeling on her large clit, but gasped again and again as it was only sporadically grazed. The anticipation of getting rubbed again built up a frenzy inside her. He went down on her, licking and sucking her big clit as he continued to finger her. He reached inside her, curling his fingers and brushing her G-spot.

"Oh fuck, Lennie!" she groaned. "Fuck me. Fuck meee!"

He jumped up and mounted her as he pushed her naked legs behind her ears. That extended clit held court over the light black skin of her outer labia and its pink center, begging Lennie to lick it. In the new position, he again drove his tongue deep into her pink pussy as he rubbed the side of her giant clit with two fingers. The rhythm became a frenzy as he continued to give and she continued to receive. Her body tightened up and froze, and her breathing became shallow and inconsistent. He jumped back and mounted her again, driving his cock deep into her pink. The contrast in color between her lips and inner vagina was sexy and hypnotizing.

"Cum! Goddammit, Cum, cum in my pussy!"

Her out-of-control screaming was sexy as hell. Lennie blasted his cum deep inside her. After a long while, as she climaxed and started to come down from the sexual high, she wrapped her legs and arms around him.

"Oh yeah, that was fantastic! You aren't going anywhere! Lie here on top of me. Keep your cock inside me. This is so good!" Beyond performing for Lennie, this was the only good sex she had in over a year. Lennie was getting to be quite the expert at pleasing a woman. He did have an incredible amount of practice from some very experienced teachers.

Lennie rested on his elbows, taking most of his body weight, so Shauna could relax and enjoy their naked skin together. She reached up and kissed him deeply, their tongues dancing together in lust. After a while, they broke free, and Lennie lay next to her. She reached down and fingered herself, drawing out a big blob of sticky, white sperm and slurping it down with her tongue.

"What next, Lennie? Do you want to fuck me in my ass? Do you want me to eat your ass? Anything else? I'm your whore, your absolute whore who will do anything for you, sweetie. Anything. Just tell me what I can do for you."

Lennie just lay there, trying to gather his breath. "I'd love to fuck your beautiful ass, Shauna. And I love it when a woman licks my asshole. But right now, I'm spent. I just want to lay here with you, enjoying your smells and the touch of your skin against mine."

"Of course, Lennie." She curled her face to lay just above his underarm.

After what must have been at least a half hour, they broke free and moved off the bed to get dressed. She kissed him once more, deeply, and pushed some remnants of his sperm into his mouth. He recognized it immediately and plunged his tongue deeper. Months ago, it would have grossed him out to taste his own sperm. Now, with Cindy and his girls, he was used to it, even looking forward to it. After an extended kissing session, they went into the shower and washed each other's entire body. They went back to getting dressed, and Shauna leaned into Lennie's personal space one more time, pulling the back of his neck in to push her wet tongue in between his lips.

"Remember me, Lennie. I hope you'll select me to work as one of Sam's escorts."

"Shauna, I don't think I could ever forget you." Their embrace was complete, and she walked out the door.

****

"How was Shauna, Lennie?"

"Holy fuck, Cindy. She was amazing! I've only had sex with a black woman once in my life. Shauna was sexy as hell. I know the saying 'once you go black, you never go back' was meant for white women screwing black men, but it makes sense in reverse, too. I mean, damn!"

"Oh, Lennie, don't worry. You're coming back to my white pussy, and the other white girls in your stable. Of course, you get some Mexican, Hawaiian, Aussie, and Irish pussy too."

Lenny laughed, embraced Cindy with a bear grip, and kissed her hard. "You know I could never leave you, baby."

****

Two days later, Lennie was back at the Sheraton, walking up to the same extended couch in the foyer. The same waitress spotted him and flipped her eyes at him; he nodded. In about a minute, he slowly walked over to the woman with strawberry blonde hair down to the middle of her back in the little black dress and black heels. She was perfectly proportioned, even though she was very petite. The curves of her ass were more like a bigger gal yet still proportionate, which only added to her allure. Her skin, like the look in her eyes, was flawless and so very sexy.

She stood up, waiting for her name to be called.

"Leslie?"

"Lennie?"

They hugged and slowly kissed as Lennie bent down to meet the diminutive woman. She rose up as tall as she could on her toes like they had known each other for years. He gently guided her to sit down on the large couch so they could look each other nearly in the eye instead of Lennie towering over a foot above her.

"Thank you for seeing me, Lennie. Samantha said you were an important man whom she needed to hear from before she would hire me. You can't believe how lucky I feel to get this chance. Samantha just told me to be myself and to make sure you have a good time."

She stopped talking and stared into his eyes. She moved a bit too close and her voice dropped an octave, saying "There is nothing more important to me than making sure you have a good time." They embraced for a slow kiss until they broke and sat beside each other.

"Did Sam say anything else about me?" Lennie queried.

"No, other than to say you were an important man and to treat you like it. Is there something else I should know?" Her question was kind and innocent, completely unlike what she looked like in her LBD and heels.

"Umm, no, not for now. So tell me why you want to come to work for Sam's escort agency."

"I've been married for about eight years now. I'm twenty-nine. I have a six-year-old daughter whom I love to death. I love my husband too, but he has a problem--a big one. It's gambling. He makes six figures a year, but you would never guess it from our bank account. He has gambled away all of our assets. We have no stocks left, our house has a second mortgage and no equity remaining, and we live paycheck to paycheck.

"Until a few months ago, when I just happened to review our bank accounts, I had no idea. I was supposed to stay home to raise our daughter, Courtney, and everything was going well until one day one of my credit cards was declined. When he came home from work, I confronted him, and that's when it all spilled out. I had no idea he had a gambling problem. He goes to the Indian casinos and bets on sports of every kind. He couldn't stop. We went from having six figures of equity in our home and more than that in savings and investments to living paycheck to paycheck. He has sought out help, but we are completely broke." Her look was sad and melancholy. Lennie prompted her to continue with a nod.

"I learned of Samantha's Escort Service from my oldest brother, who has used it a few times in the past. He's older than me and rich from the oil business; I'm originally from Texas, you see. He was talking with another one of my brothers one night during a family get-together last holiday season. The oldest one bragged about how he used prostitutes instead of getting married again. He said he likes that after sex he can just send them home without having to talk to them, and that's why he liked using expensive escorts.

"When I said that screwing whores is devoid of emotion, he laughed at me and said that it wasn't with the girls he was hiring. Then he bragged about how great what he called, umm, 'Girlfriend Experiences', that's what he called them, right?"

Lennie nodded.

"Yeah, he said they were great, and he kept wanting to see the same woman again and again. I know he has had Sam, Taylor, and Kaylani for sure; he mentioned them by name. He is still a client of Sam's escort service. He said he likes the gal who is Hawaiian the most. She has this special peaceful way when he is around her, and she's a dynamo in the sack. He has enjoyed her company for something like two years now."