Hobo- Sexual
Copyright© 2024 by OmegaPet-58
Chapter 22
Coming of Age Sex Story: Chapter 22 - 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
There were a lot of changes in my life as my time in the eleventh grade came to an end. Months earlier, after a lot of partying over the school’s “Winter Break,” I realized I needed to cut back on my sexual activities. I wanted to keep up my academics, and I wanted to have most of my lovemaking happen with the people I cared for the most.
In no particular order, they were Lena, Sheila, Avis, A&A, and my sisters. Once a week or so, I would hear from one of my old regulars, who invariably said they were missing me (missing my cock, that is). Although they were familiar with the new tipping regime, sometimes they would surprise me.
“Rubin, I’m climbing the walls! My stupid husband is on a business trip. Can I offer you $8,000 for a rush job?”
Those calls were hard to pass up.
Another thing: I agreed to be filmed (wearing a mask), so they could have something to remember me by.
In April and May, I made a new friend. Lou was my lab partner for chemistry, and we ended up studying together at that same kitchen desk I used with Arlene after school. It learned his history compared to mine; he was homeless for a time. Unlike most of our fellow students, he explained how he was officially an “emancipated minor” living on his own in a small apartment.
He had been raising himself more or less for years with a single father, an alcoholic lawyer who put his Cadillac up against a pine tree one night and died, leaving Lou with a reasonable inheritance and a survivor’s benefit from Social Security.
I could tell that he was lonely, and he confessed to being sexually inexperienced. I also noticed him eyeing my sisters closely when they breezed through the kitchen looking for cold drinks.
It was almost 100 degrees, and I put my books down and said, “Let’s go for a swim.”
“I don’t have a suit.”
“Fuck it, nobody can see back there; I’m going naked. Come on!”
We were carrying on like little boys, laughing and splashing. I guess the girls overheard us because they came out to swim with us. They were also unwilling to cover up, and it was comical to see Lou’s eyes fall out of his head (metaphorically).
“I’m happy to meet your sisters; they are beautiful. How do you tell them apart? They are so identical.”
Cass overheard him.
“It’s easy. I’m Cass. I’m the cuter one.”
“And I’m Cherise. I’m more fun in bed.”
The poor guy literally gaped at her.
“I could show you. Are you free for the next hour or so?”
Lou was incapable of responding, so I filled the conversational gap.
“I tell people Cherry has a little mole on her left ear. For some reason, I’ve never had trouble identifying them. There’s beach towels in that box. Why don’t we get out and air dry for a few minutes?”
Lou’s voice cracked and squeaked, as if he were only 13.
“Uh, I can’t. I have to stay in.”
I used my arms to swim a little closer to him, then briefly glanced down into the water.
“My friend, please don’t worry. My sisters would be disappointed if you didn’t show your appreciation. C’mon, Lou, it’s OK. They won’t tease you, not when I’m around as a better target.”
“I could wear a towel...”
Cass became impatient, stepping up behind him, pushing his shoulders, and steering him to the steps at the end of the pool.
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