Hobo- Sexual
Copyright© 2024 by OmegaPet-58
Chapter 19
Coming of Age Sex Story: Chapter 19 - 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
A few months had gone by, with many changes. Lena’s new plan for tipping greatly increased the calls from those mature couples wanting to have fun with me. At the same time, I was drowning in unfamiliar schoolwork and begged for more time with Arlene. For convenience (I claimed) going directly to Arlene’s home after school made sense.
Of course, what actually happened was that I walked in with “Honies, I’m home!” and then sunk my erection into eager Arlene’s greased-up ass for a few minutes. Then I pulled out, checked and cleaned myself, and got into missionary position. Annie was so hot by this point that I could just bury my whole length in a single firm plunge. She clung to me for the fast pounding I usually enjoyed with her, different from my mature partners. Arlene would slip her head between us and latch on, nursing and fondling her nipples.
We were becoming so familiar with each other that I could fill her pussy just as she clutched me harder and cried out her climax. As a side benefit, our quick sexual encounters left plenty of time for academics; help which I surely needed.
It was clear that I was right at the limit of what I could do with all my various sexual partners. Once a week with my sisters was a priority, of course. There was at least some respite with the menstrual cycles. The A’s and the twins by living together would be somewhat synchronized, I learned. On the other hand, the twins are such sex maniacs that they tell me ‘don’t mind the mess, fuck us anyway.’ And they know I’m such a slut that I will carry on and drive through the red zone.
I’d been through many sketchy situations during those years when we lived rough in homeless camps. But this evening I was experiencing a whole new level of strange anxiety. We all assembled for the evening meal, and, hesitantly, I laid a sealed envelope in front of my mother.
“What’s this, Rubin?”
“It’s my first report card. Fall Quarter, Eleventh Grade. I haven’t been able to open it and look.”
She smiled warmly.
“Whatever I will see here; I am proud of you. I know you have worked hard and have been very brave to suddenly jump into the regular school system at your age and with your history.”
Cass reached in impatiently and grabbed the envelope, tearing at the flap.
“Cassidy!”
“Mama, it says A, A, B, A, A, S. Your son is a fucking genius! But what is S?”
Cherry grabbed the paper from her sister’s hand.
“It’s not S for Stupid. He got a ‘Satisfactory’ in PE. That’s dumb, he knows how to pee. I’ve watched him. By his age, he should be an expert at it.”
Rubin was too overwhelmed to react to her silly comments, or to speak at all. On the table in front of him, he just studied the backs of his hands. Thea was so full of prideful emotion, she couldn’t speak either.
Harry thought he should fill the silence.
“I’ve had an amazing amount of success in my life, going from nothing to wealthy, as you know. I have so much to be proud of. But marrying Lena, and adding the Saxon family to ours, these are the things that mean everything to me now.
“I first saw something special in Thea, and now we see what amazing potential exists in her son. I guess the girls grades will come to us tomorrow, and I’m sure they will also do great.”
“Mrs. Dobson works us over. The leg chains, the whippings...”
“Shut up, Cherry. I actually saw her smile yesterday, I think she’s confident, and so am I.”
I felt more in control of myself then.
“Mom, Lena, Harry. I just have to say thank you. My life is so different, and this paper would never have happened without you. Oh, and can we give Arlene a raise? I need to ask her to close her eyes and pretend I’m a girl long enough for me to give her a huge kiss.”
Lena said, “I think when Arlene hears about your grades, she won’t pretend anything. She’ll pull her pants down and invite you to walk on the wild side. And I promise, she’s going get a big raise. In the meantime, I’m hungry. Let’s go ahead and have our dinner.”
The report card was getting a little grimy from being handled so much, but I made sure I handed it to Arlene before even getting past her front door. Then she surprised me by not attacking me sexually like usual, but tearing up and kissing me intensely all around my face. Absently, she handed the card to Annie, who squealed with joy.
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