Hobo- Sexual - Cover

Hobo- Sexual

Copyright© 2024 by OmegaPet-58

Chapter 18

Coming of Age Sex Story: Chapter 18 - 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  

On a Sunday evening in August, Thea and I stepped into Lena and Harry’s bedroom. Seeing an already naked Lena, I came up to her and pulled her lower lip into my mouth while I fondled her mature tits. Thea smirked at Harry as she started to strip off, prompting him to start by removing his shirt.

Lena dropped to her knees and began fiddling with the button on my pants. Already, I was running out of room behind my zipper. After a minute or two, I was naked, and Lena was wrapping her tits around my big cock.

Tit-fucking wasn’t high on my list, except when Lena did it. Her ample breasts cradled me completely, and she added lots of slobber, easing my way. She asked me to move to the bed, after which I lay flat on my back with her face and chest nestled in my groin. I watched eagerly as she pushed her pussy down into my face for some oral loving.

Lena had such a familiar taste and smell; a bit tart or tangy and slightly salty. Her inner lips were irregular, a bit darker along their edges. I did my best to arouse her more, running the tip of my tongue up and down the narrow spaces between the inner and outer lips. I didn’t neglect her clit, using my tongue to push it from side to side, then closing my lips over it for a gentle sucking.

Arlene and Annie coached me well. Both of them had larger-than-average clits, it seemed. Although they had lots of pubic hair, I easily found my way around. It wasn’t long before Arlene abandoned her “no sex with Rubin” rule. But only oral sex was allowed. Only Annie was being penetrated, but I certainly was getting plenty of pussy playtime.

For actual fucking, only two women were off-limits: Mom and Arlene. They were tempted, but I realized and honored their reluctance.

As she climaxed, Lena coated my face with her secretions. Her body relaxed against mine, and she stopped actively sucking on my cock.

“Rubin, come fuck me now.”

Her voice showed her need, even though it was soft and breathy.

There was enough room in the king-size bed to gently roll her off me and put her toward the center of the mattress. I grabbed a pillow from near her feet and pushed it underneath her big butt, tilting her pelvis so I could more easily pound into her.

Completely hard and covered in her spit, I was ready to push in. The mattress was already moving because, on my right (and almost within arm’s reach), Harry was eagerly fucking Mom. Her joyful cooing assured me that Harry was doing his usual excellent job of screwing her.

“Lena, I’m gonna fuck you now.”

I pushed in easily and started screwing her slowly. I liked to go this way, beginning with long, slow thrusts. Her eyes were closed, her lips parted, and I watched her face closely. I heard her usual faint sighs in time with each time I pushed in.

Her sighs stopped when I used my hand as a guide and pulled all the way out and then plunged directly inside, maybe fifteen times. I sank all the way in and held still for a moment. Then, picking up speed, I rotated my hips to match so it was actual screwing instead of just plain in and out repetition.

I didn’t have to ask since Lena had fucked me so many times since we all moved in to her house. My pace slowed a little, she noticed this and ground upwards against me. The result was almost automatic: I started flooding her vagina while moaning happily.

In the throes of my orgasm, I managed to see her goofy smile as she felt the extra wetness inside her.

“It’s always special with you, Rubin.”

“I feel the same. Let me get off you.”

“Hell, no! I like your weight on me. Just rest and recover while I hold you.”

I did notice that Harry was similarly relaxed, with his limp body resting in Mom’s arms. After we all calmed down, Lena went away for a moment and returned with large glasses of cold water and a bowl of optional ice cubes.

The four of us sat with our legs folded in a circle on the mattress. She placed a large round tray in front of us for the glasses to rest on.

“I’ve spoken to Mrs. Dobson and also to Arlene. They agree that we need to contact the high school now to take placement tests. I’m hopeful that Rubin can go into the 10th grade and the girls can start the 9th grade. The placement tests will show if the three can enroll to start high school after Labor Day.

“Thea, you’re going to be key to this process, although I will be pleased to go there with you for support.”

“Please do, Lena. You’re better than I am when dealing with bureaucrats. I think they are going to give me a bucket of shit for, um, what do they call it? Oh, yeah, truancy.

“Sure, Thea, I’ll go with you. You did the best you could in that environment you lived in.”

“Maybe I can get Mrs. Dobson to go there with us too. She certainly knows all that jargon they use.”

I thought it was the right time to speak up.

“I want to ask, can I keep working with Arlene? At least for a short time. I want her help with homework they assign to me. I’m sure some of it will be unfamiliar to me because I missed so much school.”

“I don’t see that as a problem, so long as Lena and Harry don’t object. Probably the same reasoning applies to Mrs. Dobson.”

“Thanks, Mom. And to Lena and Harry too, of course.”

Mom was getting misty.

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