Hobo- Sexual - Cover

Hobo- Sexual

Copyright© 2024 by OmegaPet-58

Chapter 9

Coming of Age Sex Story: Chapter 9 - 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 weeks later, I had spent several evenings with Avis and had a healthy $20,000 in my new bank account, which included funds from Lena. Lena sat me down one evening for a “planning meeting.”

“Two more of my friends have heard me talking about you. They are insisting on joining the club. They want to participate like Avis does with you, for the same amount of money. How do you feel about this, Rubin?”

“I’m fine with it if you tell me these women are trustworthy.”

“They are, but they are different from Avis; they have different expectations.” You might have issues with what they ask you to do.”

“Why don’t you tell me, then?”

“Alice is the first one. She says she only wants anal; that is, she wants you in her asshole, not her pussy.”

“That’s weird. Does she know I’m big? I might be uncomfortable for her.”

“She’s counting on that, actually. What do you say?”

“I can be flexible. Sure, why not?”

“Good. Yolanda is unique in another way. She wants her husband, Walt, to be right there with you. He’s in her mouth while you’re in her pussy. That’s called a spit-roast.”

“Not a problem.”

“After that, she wants both you in her pussy and him in her asshole at the same time. That’s called ‘double penetration,’ or ‘DP.’”

“Really? It seems—I don’t know—crowded. She knows I’m only 15, right?”

“She knows. Again, what do you say?”

“I guess, as long as she isn’t asking for a two-for-one discount, I’m OK.”

“You’re funny! I will let them know. How are your studies going?”

“You should check with Arlene, Lena, but I feel quite confident. She’s so good at explaining things to me. With the math, she knows when I need to backtrack and when I can skip ahead.”

“She’s young and attractive, though. Have you been behaving with her?”

“Absolutely. Lena, she’s gay; she’s in a lesbian relationship. My penis cooties are keeping her safely away.”

Lena laughed, “Good to know.”


After Rubin left her, Alice called Lena to say her “butthole had never been happier.” She wanted him again, as soon as possible. As far as I was concerned, “doggie style” was awesome, and I was sure Alice was going to be one of my favorites.

At Yolanda’s, I started feeling ill at ease. Walt was handsome and friendly and did what he could to help me relax and “go with the flow.” Yolanda was able to expose how unfamiliar I was with “DP.” She found me some high-quality porn that showed a threesome indulging this way.

“To have two hard men inside me at once, it’s so special for me. And I’ve never experienced either partner saying they didn’t enjoy it tremendously. It’s going to feel different to you, even strange, but if you watch my face and see my happiness, this will be all that matters. Will you try it?”

“I’m willing to try it if he’s the one in your ass,” I agreed.

Both of us were hard, and she was wet. We set up on their king-sized bed, with me on my back and Yolanda astride. She settled onto my wide cock with a gleeful groan. Then Walt pushed in with his well-greased cock, surprising me with the direct pressure. I felt him sliding in, as only a thin membrane separated our two pricks. Walt’s large head slid along and past my own length, and then I had another weird feeling from his balls dragging along the top of my balls.

“Alright, boys, fuck me!”

At times, we moved together. At other times, there were opposing motions, with that extra sliding stimulation of Walt’s large head sliding over my length. Yolanda was right; I kept my eyes on her face as she enjoyed the fullness in her pelvis and abdomen. It was obvious how intense the whole thing was feeling for her. To help her feel the strongest sensations, I pushed up with my hips.

Then I heard Walt and Yolanda cry out their orgasms, and my own followed quickly as I felt Walt slipping free from her next-door channel.

Standing up, Walt shook my shoulder in a friendly way, as if to say, “How about that?” before he left for the bathroom to wash up.

“Well?” asked Yolanda.

“That was surprisingly fun. But a little weird. I can see doing it once in a while with you, Yolanda. I could tell how much you and Walt enjoyed it.”

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