Hobo- Sexual - Cover

Hobo- Sexual

Copyright© 2024 by OmegaPet-58

Chapter 11

Coming of Age Sex Story: Chapter 11 - 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  

That night, the twins were in their bedroom, cuddling on Cassidy’s bed.

“I’m nervous, Cass. I don’t think Rubin’s dick will go in without hurting me. And Harry, well, Lena says he’s longer. He’s going to hit something sensitive inside and hurt me too. Remember when you put in that really long dildo and, I guess, hit my cervix or something? That was really painful.”

“That only happened once, Cherry, and only with that ridiculous thing. It must have been two feet long! I know that Rubin loves us and would be careful, and the same goes for Harry.

“In my mind, I’ve been picturing them naked since we all talked, and I’m dripping. Will you ‘69’ with me? It will help you relax.”

“Have I ever turned you down, Cass? Let me taste how wet you are, slut.”

She was telling the truth, and when Cherise happened to rouse at 2 a.m. she realized they had fallen asleep nose-to-tail after coming several times. It wasn’t the first time they had done this since they had nice roomy beds instead of the ridiculous pup tent in the woods. She rotated herself around carefully and put her face near her twin’s.

Cass always looks so peaceful and sweet when she’s sleeping!”

Only a few minutes later, Cherise was also dreaming.


Around the breakfast table, Thea was explaining today’s plans for her children.

“During the day, you three are going to be having teaching and homework time as usual. I’ll be working at Bud and Lorna’s, after I go to the Dept. of Motor Vehicles office to get my driver’s license.”

“Really? That’s great, Mom. What are you going to do for the, what do they call it? For the ‘behind the wheel’ test. The old car isn’t legal.”

“Harry is going with me with his BMW. He really spoils me, Rubin. I can’t believe how he treats us.”

“Well, you did promise me a blowjob.”

Harry had come up behind her and given her a light swat on the ass, making her giggle. Rubin rolled his eyes. She continued with the plans.

“Tonight, Rubin’s headed off to see Avis, so the big night for you girls will be tomorrow evening. Lena and I are going to be with you this evening. We need to get you both ready for Rubin and Harry. No, don’t give me that look. I know you feel ready and anxious already. Trust me, you haven’t considered everything, like pregnancy.”

“I thought you couldn’t get pregnant when it’s for your first time.”

“Cherise, that is the biggest lie, it is absolutely false. And no, you’re not too young to conceive, even though your boobs aren’t all big and floppy yet.”

“Ew, Mother!” (More unison twin-speak from the girls.)

“Oh, shut up. You know I love you. Mrs. Dobson will be here shortly. Make sure you’re ready. You too, Rubin. Lena’s going to drop you off with Avis and Dale at 7 o’clock. Don’t forget to shower, and, my goodness! You need to shave, son. Harry, can you give him a 5-minute coaching?”

“No problem. I’ve got an extra razor and blades he can take. If you’ve finished your breakfast, let’s do that now.”

“Thanks, Harry.”

“Just don’t expect me to shave between your legs; I’ll let Lena help you with that.”

“Aw, Harry, I thought you liked me.”

“I do like you; just not enough to be groping you. Not this morning, anyway.”

He smiled, and led Rubin away to the master bathroom.


“OK, girls, tonight I think we’ve covered birth control pretty well. Since your periods are very regular and also synchronized, we’re going to take a small risk tomorrow night and let you fuck the guys bareback. The only reason we can risk this is that you are three days away from your next period, so there’s all no way an egg can implant and start becoming a successful embryo.

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