Hobo- Sexual - Cover

Hobo- Sexual

Copyright© 2024 by OmegaPet-58

Chapter 8

Coming of Age Sex Story: Chapter 8 - 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 next few days for the three of us were focused on education. Elaine Dobson, another one among Lena’s vast circle of women friends, came in to work with us. Mrs. Dobson, as she called herself, was a former high school teacher who had retired early in her thirties to raise her children.

Of course, I noticed how attractive she was, but I didn’t feel any returned interest on her part. It was strictly business with her. She put me through a rigorous evaluation of everything I had learned up to this point, asking question after question. With me, her manner was firm but still friendly. It helped that I liked her, because I felt very inadequate because so many of her questions flew far over my head.

Cherise and Cassidy had a similar reaction when we got together to talk about things after she left. When her evaluation was complete, we all met to discuss her findings and recommendations.

“Let me start by saying how much I enjoyed meeting you three. You have great personalities and a perspective from your history that a lot of people I meet have missed out on. But (and you knew there was a ‘but’ coming) all the formal schooling you’ve missed has left you well behind. Rubin already knows this.

“I think the best thing for you all is tutoring, to fill in the holes so that in the fall you can go into regular school and not be floundering. The twins would spend three hours a day with me (or someone like me), and two hours on their own studying.

“For Rubin, I have a different idea. I think we can get a master’s student from the university’s school of education to tutor him and then write her (or his) thesis on how he makes progress. Rubin comes completely bare into this process. He hasn’t had television, computer, or internet access; practically no exposure to libraries, only what Thea has managed to put together.

“And if you’ll forgive me, home schooling when you’re homeless is kind of a non-starter. An oxymoron, if you will.

“I have a colleague at the university who could assist me in arranging this. One thing, though, and this is critical. Rubin, if the graduate student who comes to tutor you is an attractive young woman, as is likely, you absolutely CANNOT be unprofessional with her. No flirting, no suggestive words, no nothing. Any involvement between you would make her research invalid. If you can’t behave, the deal’s off.”

Busted! How did she know I was imagining this? I had to promise.

It took several days for these arrangements to be put in place. It turned out there was no need to worry. Arlene, my tutor, was safe for me because she was a lesbian. Besides, I was otherwise engaged, dick-wise.

The arranged time for Avis had come. I wore some of my new upscale clothes, and Lena and I rang her doorbell at 6 p.m. I wasn’t sure what I was expecting, but she surprised me when her huge front door swung open.

I’d been told she was age 40 and curvy, that’s all. Avis was possibly of Greek or Italian ancestry, with skin tone to match. Her eyes were a deep brown, and her hair was long, wavy, and jet black. Under her loose blouse were clearly the largest tits I had ever seen. Her belly was a little round, her hips generous, and her thighs thick.

When I drank her in, my idea of sexy femininity suddenly included a whole new range of types. I must have been gaping, or at least showing a goofy smile. Of course, she was studying me with the same intense inspection. I almost jumped when I heard Lena.

“Avis, this is my new friend Rubin. I think he’s almost as anxious to meet you as you are to meet him. Can we come in, or should we just leer at each other some more?”

“I’m sorry, yes, please, come in and get out of the heat. Can I get you anything? Water? Coke? Beer?”

“We’re fine; we just had dinner.”

“Then let’s go into the living room.”

“Is Dale around?”

I assumed that was her husband.

“He’s staying out of sight tonight, at my request. Forgive me, I’m kind of eager to get down to business.”

Avis picked up a stuffed envelope from the coffee table and handed it to me.

“It’s $5,000 in fifties and twenties, just like Lena suggested. Count it if you like.”

“Thank you; I’m sure it’s fine. I guess Lena’s trying to get me a bank account so maybe I can handle these things differently.”

I handed the envelope to Lena to put in her purse.

“Lena, Rubin, I want to remind you of a couple things. Lena, there’s a wing chair in the corner of the bedroom where you can silently watch us. I’ll give you a towel to sit on, you hussy. Rubin, I want you to have fun. Don’t hesitate to ask me if you want something or tell me if I need to do something differently. Are you ready?”

“Uh, eager.”

“Ooh, perfect. Let’s go!”

It was another luxurious house, and her bedroom was huge. Three king-size beds could fit easily in the space. Wearing only a huge smile, Lena took a towel to the chair and sat down to watch us.

“Can I undress you, Avis?”

Lena had influenced me before, so I took my time, moving slowly and smoothly. Her blouse was silk or satin; it slipped over my hands and fluttered to the floor while I stepped around to her back. Lena had coached me; I was ready for the four hooks of her substantial bra. I pushed my hands underneath the band and shoulder straps until her bra hit the floor as well.

Even without the coaching, there was no way I was going to miss holding her heavy breasts. Avis sighed, leaning back into my chest. I had to say something.

“Wonderful,” I whispered into her ear.

After a couple of beats, she lowered the zipper on the side of her slacks and pushed her pants and panties over her ample butt and down her thighs.

“Let me sit,” she cooed.

Turning to face me, she bent her knees and seated herself on the mattress. I dropped to my knees on the extra-soft carpet and unfastened the straps on her sandals, then scooted her pants and panties off of each foot.

“Come here so I can undress you.”

I moved forward so my knees were between her splayed legs. I couldn’t resist getting a glimpse of her trimmed pussy mound and the bare lips below. She reached up and started unbuttoning the five buttons of my long-sleeved dress shirt, so I took the opportunity to undo the sleeve buttons, and then my shirt joined the clothes on the floor.

I did have a little self-consciousness about standing there with no top. There are only wisps of chest hair, and there is nothing close to a six-pack further down. Judging by her expression, Avis found no fault with me, though. She fiddled with the button on my pants, then grumbled.

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