Hobo- Sexual
Copyright© 2024 by OmegaPet-58
Chapter 26
Coming of Age Sex Story: Chapter 26 - Completed 9/4/24 "Deadhead" Thea has lived "under the stars" for 30 years, hooking for food money. Her son, 15, and daughters, almost 14, are withering from the homeless poverty that is all they've ever known. A wealthy couple hires Thea and then Rubin for sex, then takes the family into their lives and home for the kids' sake. Schooled during the day, Rubin begins a profitable night life using his large gift as a gigolo for wealthy older women, who enjoy teaching him the ins and outs.
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa mt/ft mt/Fa mt/mt Mult Consensual BiSexual Heterosexual Fiction Rags To Riches Sharing Wife Watching Incest Mother Son Brother Sister Group Sex Orgy Swinging Anal Sex Double Penetration First Oral Sex Sex Toys Tit-Fucking Voyeurism Water Sports Big Breasts Menstrual Play Size Small Breasts Prostitution
I got in touch with Annie and Arlene, and we worked out the timing to have a full night together just three days before Arlene’s period was due. On that night, Lou and I had a nice supper around 7, and then when we undressed, my two friends went, well, ape-shit. There’s no other way to describe it.
It was about two in the morning when we either ran out of lube or just fell asleep from total exhaustion (I’m not sure).
Something that was much harder for us was when I needed to come clean with Lou and fully explain some of my history that I had kept from him. I asked Lou to receive Mom and me at his house, so he would feel secure in case he wanted me gone.
I went all the way back to our time behind the Dollar Store when Mom was going out and hooking just so we could eat. I told Lou how things started to change when Harry and Lena first hired her, and then me. I explained that Lena had been my first, just like she was for him.
By this point, Lou was looking bad. He excused himself and disappeared into the bathroom for about twenty minutes. I was thinking we should go when he reappeared. His face was freshly washed; make of that what you will.
“Keep going, Rubin. I want to know all of it.”
That’s when I explained about my gigolo business and how I made money for my future education. I talked about how wealthy couples would seek me out to explore their various kinks. And how the husbands sometimes wanted me as well as the wives.
I told him how I was still seeing some of them, like Avis and Dale, but now I was just accepting tips, and declining many requests.
Lastly, I confessed to him how the barriers were down between me and my sisters, which led to me being with Sheila. Just recently, how I went through that very last limit when he and I both fucked Mom.
That’s when I ground to a halt and sat on his sofa, studying my hands and waiting for Lou to speak.
“I think, Rubin, Thea, you were properly concerned about my reaction to all of this information. But I also think you have misjudged me, Thea. Lena, and Harry were right to step in when they did. You must know that now.”
Lou stood up and stared down at Mom.
“I know what it’s like to try to raise myself as a kid without proper parenting. Lena, Harry, and Rubin saved your family. Make no mistake. I have to respect that. I respect that you sacrificed before that by being a hooker. That’s all the judging I’m going to do.
“Rubin, you should have told me. Yes, I have some money, but my life is kind of precarious. I could lose this little house, and I have no money saved up for college. Perhaps, from what I’ve heard, the incredibly generous Harry might donate towards a scholarship for me. But I do need money.
“I would like you to introduce me to all your generous friends and former clients. Tell them that I am now like you were then.
“Tell them I would be happy and grateful to have a night of fun with them, on my own or with you helping out, while taking tips so that my finances would be more stable. From what you’ve been telling me, you had a special talent for this kind of work, and I’m not just talking about your big cock.”
“You’re right, Lou,” interjected Thea. “His cock was like an introduction card; it got him in the door. But then they saw beyond it: he was a great kid and a pleasure to be with. Like you are, Lou. You both have overcome difficult beginnings to become wonderful young men. Rubin is the son I definitely don’t deserve. And you’re the son your drunken father didn’t deserve, either.
“Rubin, what do you think?”
“Lou, Mom is right. I can think of six or seven wealthy women who would go nuts when they learn about you. At first, they would want us to show up together just to feel secure, since they only know me. I have to warn you, though, they will look at you and look at me, and be asking for double penetration. I’m sure of it. What, Mother?”
“I think, before we go home tonight, the three of us should practice. Yeah, DP.”
“Thea, you slut; I can smell your pussy from here. OK, we will. But first, there’s one more thing we should talk about.”
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