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Chapter 15
by
OttoVonHerunterhangen
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Rob Gets Lucky Part 2

“Rob I have a problem I was hoping you could help me with,” Mary started.
Rob frowned. This wasn’t the line of conversation he was hoping for. “What’s the problem?” he asked.
“Well as you know, I signed up for WHORES, the problem is I haven’t had sex with a 19 year old since I was around 19 which was… a few years ago,” Mary explained.
Rob grinned, “Yeah, the odd year or so.”
“In any case, I didn’t want to start off in the program without ‘freshening up’ my technique with younger men, and I was wondering if you might want to get a practice session in,” Mary explained as she laid a hand on his crotch.

“Um, um, um…” Rob said suavely.
“Am I making you nervous?” Mary grinned as she unzipped his pants.
“Wh-what will Thomas say?” Rob stuttered.
Mary laughed, “He had a head start on you, if he isn’t fucking your mother silly by now something is wrong with him.”
Mary got Rob’s dick out of his pants, it was already fully erect and she figured it was pretty close to eruption. Better get the first load done and prep him for the second afterwards.
“Rob, have you ever heard of premature ejaculation?” Mary asked.
“No,” Rob said, though he had a pretty good idea of what Mary was talking about.

“It’s when a guy cums before sex can happen. It’s fairly common in young inexperienced men. Happily you guys have real short refractory periods,” Mary whispered in Rob’s ear.
“Refractory period?” Rob asked.
“The amount of time before you can get another erection. At your age it only takes a couple of minutes. In older males it can take hours,” Mary explained.

She took off her top and knelt in front of Rob, sliding his dick between her breasts. She was soon rewarded with a thick load of cum which splashed up on her face and glasses. She paused to wipe both off, remove her shorts, and grab a rubber.

She was pleased to see while she was doing that, Rob was already semi-erect.
“OK champ, time for the main event. Off with the shirt.”
Rob obliged quickly and Mary straddled him on the couch and kissed him as he nipped at her nipples.
As soon as his penis was fully erect Mary unwrapped the condom and rolled it over Rob’s dick.
“Did they teach you about this?” Mary asked.
“Yeah, only we used banana’s in class.
Mary laughed, “Well it’s important both to prevent pregnancy and STD’s, so that’s good. They are also mandatory for the program.”

She climbed on top of Rob and guided Rob’s penis into her vagina. She started moving up and down, soon getting a good bouncing rhythm going.
Rob for his part started energetically thrusting, and soon both of them were in the midst of an orgasm caused by fierce movement and the fact Mary had used a ribbed rubber, which she was now somewhat regretting despite the orgasm because it would likely cause her to walk funny for a period of time. She had gotten in the habit of using them with Frank, whose enthusiasm over sex with her had greatly waned towards the end and required significant help if she was going to get any kind of arousal at all.

They got done, and Mary rolled off Rob and sat on the couch.
“What do I do with this?” Rob asked, holding the condom?
“Wrap it in a tissue and throw it in the trash can,” Mary replied.
“What if Thomas finds it? Can’t I just flush it?” Rob asked.
“No, they aren’t good for the plumbing system, and Thomas probably has a pretty good idea we fucked. It might be a good idea to get dressed though, he might be home soon,” Mary said, putting clothes back on.
Rob got dressed also, then hesitated. “Mary, there is something I should tell you.”
“OK, what’s up?”
“The reason that Thomas acts the way he does around you is he really wants to fuck you. He doesn’t know how to tell you, and he is really conflicted about it.”
Mary frowned, “Yeah, that explains a lot, and I should have suspected it.”
“What are you going to do?” Rob asked.
“I don’t know yet. I grew up in an art commune, sex was natural including among family members. My ex never understood. Have you had sexual relations in your family?”
“No,” Rob replied.
“It does alter relationships, I’ve had sex with my father, brother, and a couple of male cousins. All well before my marriage to Frank of course.”
“He found out?” Rob asked.
“He suspected, he visited the commune and saw what was going on. He never completely trusted me, and he may have caught on to what Thomas was thinking, that may have been part of the reason for the split, though I think he was already fooling around at that point.”
“And you didn’t,” Rob replied.
“Nope, not until after the divorce was finalized,” Mary said. “OK, you better get before Thomas comes home, we’ll talk further later.”
“Good luck,” Rob said as he was leaving.
“Yeah, I’m going to need it,” Mary muttered to herself.
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MILF and Cockies
It's a nice day to... start again
Mary, a 42 artist with 19 year old college student son and a recently finalized divorce considers her options for male companionship. Her 44 year old ex is focusing on 20 something females. Mary decides what's good for the gander...
Updated on May 25, 2026
by OttoVonHerunterhangen
Created on Nov 24, 2025
by OttoVonHerunterhangen
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