Hobo- Sexual - Cover

Hobo- Sexual

Copyright© 2024 by OmegaPet-58

Chapter 24

Coming of Age Sex Story: Chapter 24 - 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  

The twins acted cross through dinner, until Thea scolded them and reminded them that if they behaved, Lou might want to try them out in the future. Suddenly, they became precious angel daughters.

I teased my friend.

“I’ll go into storage and get the lights, the cameras, and the microphones set up. We’ll run the cable to the living room so we can all watch and critique his performance in real time. Plus we can post the recording on the tube sites. Lou, I’m going to make you a star.”

“Fuck you, Saxon.”

“Rubin, shut your hole. Or I’ll put you in storage and lock you in.”

At eight o’clock, it was time. I patted Lou on the back.

“Go get ‘em, tiger!”

Mom kissed him and gave his little butt a loving squeeze.

“Lena is the best.”

Harry wished him well, and the girls gave him sweet kisses “for luck.”

After about 15 minutes of nervous pacing, Thea sent me out to the pool.

“Take a swim, bonehead, and try to clear your head.”

I did swim some laps, then Mom came out to join me on the patio.

“I’m really glad you brought Lou. I think he’s going to be a fantastic addition to our little group. I wonder, perhaps he might want to pick up some cash once in a while?”

“You mean, ‘tips’?”

“Exactly. He’s certainly qualified in the penile area.”

“I thought you and Lena were going to drain the poor guy dry.”

“That’s next week’s project, Rubin. But after that...”

“I have an idea where you’re going, and it’s going to need a lot more discussion with him. Let’s go see how he did.”


I recognized the look on Lou’s face. It matched the one I wore when Lena introduced me to the joys of sex.

“My life is different now. I’ve been to paradise!”

Lena smiled like the “cat who ate the canary.” Thea had a question.

“Rubin or Lou?”

Lena didn’t stop to consider; she had an immediate answer.

“Rubin AND Lou!”

He was a little wobbly, so I took him to my bedroom and helped him undress and get into my bed. Then I went out and looked for the twins.

“Would you two accept me as a substitute tonight?”

They were so excited, I managed to set off two orgasms for each of them. I left their bedroom, walked back to my room, naked as usual, and slipped into bed next to a dead-to-the-world Lou.

About midnight, something woke me up. The mattress was shaking; Lou was jerking off!

“Hey, Lou.”

“Oh! Sorry, I was trying not to wake you.”

“It’s fine. Just wait, hold still, I’ll get Mom.”

“Wha?”

“Hold still!”

Quietly, I went over to the master. Since Mom wasn’t in the middle, I was able to quietly get her up and out of the room.

“Lou’s awake and erect. Come and get it.”

“Yeah!” she whispered.

In the room, she switched on the nightstand lamp. His giant dong was perfectly upright, with his thumb and forefinger circling its root.

“Hey, honey, wanna fuck?”

“Please!”

Mom put her knees on each side of his prone body. Mostly for expediency, but also because I was curious, I put Lou’s huge knob into my mouth, adding slobber. He really was big! Then I pushed him into her vagina, and she started happily humping.

“Rubin! Get up here!” Mom whispered. She was so horny, she inhaled me and enjoyed our big cocks in both ends.

For a minute, Lou stared up at me, big-eyed. Then, he remembered that he was fucking a new vagina and closed his eyes and gleefully groaned. This went on for a short while, but he was too amped up to last very long.

The bed twitched as he stiffened and obviously pumped into my mom’s pussy.

“Fuck! Too fast.”

Mom was unhappy, wound up, and tense, but not at her peak yet.

“Rubin! Get in there!”

I repositioned and pulled his softening cock out of my way. I stuffed it up between their two hairy groins. With Mom on her back and Lou between us, I pushed my hard cock into her soggy pussy and began fucking in earnest. I’m sure he felt my balls dragging back and forth over his balls and her stiff nipples poking into his chest as I pushed in as deeply as I could.

Along with her panting, I could hear tiny squishing sounds from her wetter and wetter vagina. I was able to hold off until I was sure she was coming. Coming hard! Then I let loose, mixing my cream with my friend’s cum inside her.

“Dude, you just fucked your mother.”

“Yeah? So did you. We’re brother mother fuckers now, Lou. We should get joint bank accounts or something.”

“Boys! Shut up and let me enjoy my bliss. Let’s get some sleep; kiss me. I love you both.”

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