Date: Fri, 29 Sep 2023 17:18:10 -0400 From: James Karvonen Subject: Song of the Lonesome Steel Rails: 51 After breakfast that morning, Bobby and Josh were summoned to Madame Eustis's bedroom. Knocking on the door they waited patiently for Madame Eustis to invite them in. Few seconds later I Heard a voice coming from the room saying, " Come on in boys ". Opening the door they slowly walked into the room or paused and stood side by side facing the brothel madam. Her bedroom smelled of flowers, perfume and other sweet smelling things. It didn't surprise them any to see that Madame Eustis was not alone She was sitting on her large king size bed dressed in one of her most flimsiest dresses. Little Lucas was string on her lap. She was dressed in one of her most flimsiest outfits, a low-cut dress. Her hair had been combed down so that it was now resting on her shoulders. Bobby noted that Madame Eustis had her left hand on little Lucas's bare back, and that she will gently rubbing and stroking his back. At the same time little Lucas had one of his small hands around Madame Eustis's left breast and her plump pink nipple in his mouth and was sucking on it almost greedily like he was still a little baby. Bobby was surprised to see that little Lucas was dressed only in a diaper. He thought that, that was rather odd for a 9-year-old boy. When he asked Madame Eustis about that, Madame Eustis shrugged then told him, "There are some men and women in this city that have diaper fetishes. The Sheiks Brothel addresses all type of sexual fetishes that both men and women have, no matter what those fetishes are. That's why the Sheiks Brothel is so popular in the great city of New Orleans." Bobby nodded and looked over at Josh who was watching little Lucas also. "All right that's enough my dear Lucas." She tenderly pushed Lucas's head away from her, breaking the contact that he had with his lips wrapped around her nipple. Madame Eustis's plump nipple wet and glistening with the little boys saliva. "If you don't mind dear Lucas I would like to spend some time alone with Bobby and Josh, so go see Hannah and tell her that I will be with her shortly." " Ahhh, do I have to?" Little Lucas frowned. It was obvious that the little boy wanted to stay with Madame Eustace. "Yes, you have to dear child." Madame Eustis added. With a frown little Lucas slid off of Madame Eustis's lap, Then padded the carpeted floor to the bedroom door. He opened it then slowly walked out of the room closing the door behind him. Madam Eustis adjusted her dress so that her pump breast was no longer exposed, then looked at the two boys standing in front of her. "Tell me, after Dr. Kiplinski this last night, did you two have any further sex with each other before falling back to sleep or after you had woken up?" Bobby looked at Josh then back at Madame Eustis. "Well did you or didn't you? " Madame prodded. " Well, when we woke up this morning we kind of messed around with each other. " Bobby admitted. " When you say messed around, what did you do? " Madame Eustis wanted to know. Bobby smiled then said, " I tried that squeeze method on him that he told us about the other day and drove him absolutely crazy. " Bobby chuckled. " And I got back at him and sucked him off until he was begging for mercy." Josh laughed. " Did you both climax? " Madame Eustis wanted to know. Bobby and Josh both nodded. "So that was your first ejaculations of the morning? " Madame Eustis continued. " Yes ma'am." Bobby said. Josh nodded also. "I am pleased that you two are sexually active with each other. It's good that you have that opportunity to practice the techniques in the art of sexual pleasure that you will learn at my brothel while you are here. Now let me ask you this is question, how many times can you two get off this morning since waking up? " Bobby looked over at Josh not sure exactly what Madame Eustis was leading up to. It took him only a few seconds to finally say, " Just once, that's all right Josh? " Josh nodded. " I see, well that's a start. Now let me ask you this question. How many times per day to you two think that you can get off during a 12-hour period?" Again both boys looked at each other than shrugged. " I don't know, maybe three or four times possibly even five depending on how horny we get." Bobby chuckled. " Yeah I would say Bobby is right about that. " Josh admitted blushing a what do in response to Madame Eustis's questions. "Well today during your training I want to find out how long you two could go without getting exhausted from having multiple orgasms. " Madame Eustis stated. " We're going to start that exercise off right now. What I want you both to do is to take off all your clothes. Don't be shy because as long as you work for me, you'll be doing this quite a bit." " Yes ma'am! " Bobby said. He was thinking that this could turn out to be a very interesting day if not an exhausting day if what Madame Eustis said was true. While Madame Eustis watched, Bobby slowly started to undress. Besides him Josh was slowly starting to undress as well. Before long both boys were bared to the waist. With eager anticipation, Madame Eustis watched. So far she was pleased with her two new acquisitions. They definitely would bring in more money to her establishment. She was glad that Hannah had decided to bring the two boys with her to this establishment. She watched as both Josh and Bobby pulled off their pants followed by their underdrawers. Before long both boys were standing before her, butt ass naked as the day they were born. Her eyes wandered up and down over both boys nude bodies. They were both about the same height and weight, their nude young bodies glowing with an a dark tan. She watched as their rib cages expanded and retracted with each breath they took. Their chests were firm and well cut dotted by two pink nipples. Their stomachs were taunt and firm without an ounce of fat on either of their developing torsos. Josh's stomach was centered by an outie belly button while Bobby had an innie belly button not that it made any difference to her clients. What interested her the most about her latest aqusations was the differences in their penises. Bobby's slender penis was circumcised, about 3 inches in flaccid length. It drooped over his low hanging, almost full grown balls. Josh's penis was uncircumcised with a nicely tapered foreskin, however his soft shaft was a tad thicker then Bobbys and at least 2 inches longer then Bobbys penis in it's flaccid length. His low hanging balls were plumper and mature then Bobby's balls were. For a 12 year old boy he was more then well endowed. Both boys were still hairless though she did note a couple of unruly thin strands of pubic hair sprouting at the very root of Bobby's cock. Another 6 months or so he more than likely would be sporting a small bush. Josh on the other hand was as bald down there as he was when he was born. And in a way that made his penis even longer and thicker than it actually was. An interesting study in contrasts, Madame Eustis thought. "Move a little closer together. " Madame Eustis stated. Both boys did as they were instructed to do. They were now standing side by side. Reaching out with her left hand, Madame Eustis gently grasped Bobby's flaccid member then started to rub the most sensitive part of Bobby's beneath the circumcised head with her thumb and two fingers. Her right hand moved over to Josh's flaccid cock and gently she began to fondle and rub it just like she was doing to Bobby right now. She knew the foreskin back and ran the ball of her thumb over the ultra-sensitive glands. "One of the things that we're going to find out today is over a 10-hour time span how many times you two can ejaculate. You said you already did it once this morning so when I bring you to ejaculation this will be your second time today. And then throughout your training as a day progresses we're going to keep bringing you off until to see how long you can go before reaching the point of sexual exhaustion." With that having been said, using a three fingered grip Madame Eustis started rubbing both Bobby and Josh's cock up and down. Within seconds her skillful fingertips cause both Bobby and Josh to become erect. Bobby sported a proud 5-in erection, whereas Josh's penis stretched out to it's almost maximum 7-in length. As madame Eustis continued to masturbate both boys, once again it was a study and contrasts. Before long herb skillful fingertips had both Bobby and Josh leaking a little precum around the heads your cocks that anointed Madame Eustis's stroking fingertips. Before long Madame Eustis's skillful fingertips had both Bobby and Josh gasping for breath, moaning and squirming in what can only be described as undeniable pleasure. Her fondling fingers and hands moved down between their legs too cup and tenderly roll both Bobby and Josh's low hanging still developing balls, then moved her fingertips back up to their rigid members. It didn't take long for the inevitable to happen. Madame Eustis speeded up her strokes interested in seeing which one of the two boys would climax first. It was Josh who tensed then cried first with his release. His still clearish boy cum out in spiddled out over Madame Eustis's rubbing fingertips. Second later Bobby reached his point of no return. His cock flexed hard between Madame Eustis's rubbing and fondling fingers then bolted sending a couple of rapid spurts of slightly milky boy cum onto Madame Eustis's low cut dress as she sat on her bed in front of them doing her thing. She continued to rub and fondle them both until they were spent, then casually released her grips on their wilting cocks. She smiled then said, " Go ahead and clean yourselves up. When you're done Bobby I want you to get with Hannah and she's going to work with you for the next couple of hours. And Josh you can get with Daisy, and we'll see what happens the next couple hours. With that having been said, she excused the two boys. They went on ahead and pulled their clothes back on. A few minutes later they left the bedroom and headed back into the dining room and main lobby where the other prostitutes were congregated, still eating breakfast. They sat down and ate with the other female prostitutes and Little Lucas. After they ate their breakfast, as what Madame Eustis told them that they needed to do, Bobby got with Hannah who was more then happy to instruct the boy in the arts of pleasure, and in turn Daisy was more then happy to work with Josh as well. And so during that day their training continued. As skilled as they were, both Hannah and Daisy brought the two boys off to places that they had never been before as far as sexual pleasure was concerned. As Madam Eustis had told them, each training session they had during that day ended up with an ejaculation. As the month passed they continued their training almost on a daily basis. Thanksgiving finally came and went. Before long November dissolved into December. It wasn't until the first part of December that Madame Eustis finally decided that Bobby and Josh had finished their training to the point that they were now ready to start making ends meet. She allowed Bobby and Josh to have at least one client each night during that time, a client that she would chose. Most of the time it was a male, but occasionally it would be a female. During those times the two boys worked separately, but sometimes who were like Dr. Kiplinski who preferred threesomes came along they would work as a team together. They had no real problems with the clients that Madame Eustis chose for them. Her clients would come in, get their most perverted sexual needs and fantasies fulfilled with young boys then leave, paying Madame Eustis directly for their services. Occasionally they would get a client who liked rough sex. Bobby and Josh had both been exposed to rough sex, from Josh's father and brothers so they knew what to expect and would prepare themselves for it. But those clients who enjoyed rough sex were never as brutal as Josh's father and brothers had been to them. The clients who enjoyed rough sex mainly did it through role playing and would never really try to hurt them. Madame Eustis made sure of that. She didn't want to see any of her girls, and boys get hurt when they would get together with their clients. Christmas came and went and the brothel under Madame Eustis's supervision started getting ready for their most busiest time of the year. That time was New Years Eve. Time was running down before 1932 would finally dissolve into 1933. It had been a very long year for Bobby. More then six months had passed since he had run away from Pine Island Industrial school and farm with hopes of riding the rails to California so that he could be with his father. His main goal was to get his father to move his family from Middletown NY to Bakersfield, CA. He had no idea back then that it would take so long for him to get to California riding the rails like he had been doing. But one thing crisis turned into another crisis and he was just as far away from California as he had been just before leaving New York. Now he was a boy prostitute in a New Orleans brothel trying to earn a little money so that he could continue his cross country journey. The money that he had earned this far, Madame Eustis was holding for him, though she did say that whenever he would be ready to leave she would give it to him. But when would he be ready to leave? That was the big question that was now weighing heavy on his mind. It was winter time, and even though he was now living in New Orleans, the days still got damp and cold. Right now he didn't have to worry about snow, but if he were to leave within the next few weeks, that concern would be there for him. Heading west the weather would even be even colder and more uncomfortable for him, especially going through the states of Texas and Arizona, and Southern California when winter would be at its peak. So heading into the new year, there is a lot on Bobby's mind. He wanted to leave New Orleans as soon as he could, but you would have to take the weather into consideration because it wasn't going to get any easier for him. On the last day of the month of December Madame Eustis called Bobby and Josh into her room and told them both, "Come tomorrow night, for New Year's Eve, I would like you two to dress up as girls." " What?" Josh exclaimed. Bobby could tell that Josh wasn't to keen on that idea. As far as it mattered for him, he didn't mind dressing up as a girl. He had done it before back when he was in Pointe of the Rocks, Maryland living temporarily with Dot, Kim and Antonio at Dot's boarding house. Kim wanted him to dress up as a girl because she had always dreamed about what it would be like having a sister. "Is this something you rather not do Josh?" Madame Eustis asked. There there was an edge of sincerity in her voice. Josh nodded. " What about you Bobby, how do you feel about that? " Wanting to please Madame Eustis, Bobby said, " That don't really bother me. " "Okay Josh, then if that is something that you really don't want to do then you won't have to dress up as a girl for New Year's eve. I'm not going to force you to do anything. Get with Daisy tomorrow and she'll get you set up for what you will need to do for our New Year's Eve party and celebration tomorrow night. You may be excused. " Josh breathed a sigh of relief, nodded then said, "then yes ma'am! " Bobby turned to leave with Josh, but Madame Eustis stopped him. " Bobby stay with me for a few more minutes. " " Okay. " Bobby said, turning back around. Bobby watched as Josh casually left Madame Eustis's bedroom. " You sure it's not going to bother you to dress up as a girl? " Bobby shook his head. "I've done it before. " Bobby added truthfully. Madame Eustis seemed surprised. " You have? " "Yes ma'am. " And then without going into any specific detail Bobby told Madame Eustis about his experiences dressing up as a girl back in Maryland. "Well I'm glad to hear that. So tomorrow night around 3:00 I want you to meet me here in my room and then I'll go ahead and get you fixed up for tomorrow night's New Year's Eve party and celebration. With your hair as long as it is now now you're going to be a natural as a girl. No one will be able to tell the difference until they unwrap the package. " Madame Eustis chuckled. Bobby smiled, then turned and left the room also to catch up with Josh. The New Year's party and celebration should be really interesting. Bobby thought as he made his way through the main lobby of the whorehouse to catch up with Josh......