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Chapter 14
by
OttoVonHerunterhangen
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Rob Gets Lucky Part 1

“Hi champ, got an errand for you to run,” Mary said over breakfast.
“Oh mom, can’t it wait? I was going to over to Curt’s for a “Call of Duty” session,” Thomas protested
“It won’t take long, and it’s on the way. I want you to take a piece of pottery over to Jordan,” Mary said
“OK, I’ll just drop it off on the front porch,” said Thomas.
“No, ring the doorbell and hand it to her,” Mary replied, “If you just drop it off on the porch and some asshole kid comes by and decides it would be fun to smash a piece of pottery on the sidewalk you’ll never guess who is going to be working off a piece of pottery.”
“Um yeah, I get the picture mom,” Thomas replied.
He grabbed the requested item, stuffed it (carefully) in the back seat of his car, and took off in the direction of Rob’s house.
When he got there he met Rob coming down the sidewalk.
“Dude, what’s up?” Rob asked.
“Mom wanted me to deliver this piece of pottery to your mother. Can you give it to her for me? Then we can both be on our way to Curt’s apartment for our “Call of Duty” session,” Thomas replied.
Rob thought about it. His mom had just given him $50 with instructions to give it to Mary to pay her for some pottery. That was currently being delivered by Thomas. Who she just could have given the $50 to. Rob had a pretty good idea this wasn’t about a piece of pottery.
“Dude, I think you ought to go in and hand that to my mom. I’ve got an errand I am being sent on too, so I’m going to be late to that game session,” Rob suggested.
“What’s this all about?” Thomas asked, puzzled.
“I’m not sure man, I just think you really need to deliver that pottery yourself,” Rob replied.
“Um, OK,” Thomas said.
Rob got in his car, and started off to Thomas’s house. “This might prove to be a very interesting day,” he thought.
While he was socially backward Rob was not at all stupid and it really didn’t take much in the way of deduction to figure out what was going on. And if this was pointing to him getting to fuck Thomas’s mom today, he was all for it, he thought she was totally hot, and had been the item of interest in a number of his fapping sessions.
On the other hand Rob was well aware that he could be reading the situation all wrong, and a move to put the make on Thomas’s mother could well be the end of a friendship, not to mention a career, and possibly ruining his whole life depending on how south things went.
So it was an extremely aroused and extremely cautious Rob that rang Mary’s doorbell.
The door swung open “Hi, Rob, come on in, your mom said you were coming by,” Mary greeted him.
She was wearing a deep cut tank top and short shorts much the way Rob envisioned her in his fapping sessions. And carrying a pink duster which he didn’t imagine her with, but might have to start.
“H-Hi Mrs… Mary,” Rob stammered, remembering at the last moment that she did not like being called by her married name, “Mom sent me to pay you for some pottery.”
Mary laughed, “Thanks, I wanted to talk to you anyway, I’ve got some housework to do, why don’t you come along. You’re not busy are you?”
“Well yes I am, but I’ll trade a ‘Call of Duty’ session for a chance to fuck any day of the week and twice on Saturday,” Rob thought as he followed her in.
“No ma’am,” was what he said.

Mary started dusting as she worked her way around the room, Rob trailing her admiring her butt.
“Are you and Thomas the only two of your group going to WMIT?” Mary asked as she dusted the table.
“Curt’s going to the state university, he has a football scholarship there. Lucas is going to a private college his father went to, there are scholarships for legacy’s there, I think he has one. There is one other girl from our class going to WMIT,” Rob said.
“Really? What’s her name?” Mary said, surprised, though she supposed she shouldn’t be.
“Susan Simpson,” Rob replied.
“Wait, she wouldn’t have light brown shoulder length hair, slender build, and be taking a business computing class with Rob?” Mary asked.
“Yeah, that’s her,” Rob replied, “I was trying to date her but she has an older boyfriend. Pretty much every girl in the technology fields either isn’t interested in dating or has an older boyfriend already.”
Mary decided if the opportunity arose she was going to find out more about Susan Simpson, she apparently wasn’t just a brainless cutie who caught her ex’s eye.
“Thomas complains about that type of thing all the time. Curt and Lucas don’t have that problem too, do they?” Mary asked.
“Nah, Curt’s a jock, they get chicks constantly. Lucas is pretty good with patter too, he’s had plenty of girlfriends,” Rob replied.
“And sex too I imagine,” Mary added.
“Yeah,” Rob said a bit wistfully. “Thomas and I are the only two in the group that haven’t.”
“Which is part of why you chose to go to WMIT I bet,” Mary pondered.
“Um, yeah, part of it,” Rob said, a bit embarrassed, though it was the direction he hoped the conversation would take.
“I understand your brother went there too,” Mary continued.
“Yeah, he just graduated in electrical engineering and chip design,” Rob said.
“That sounds like a pretty lucrative field,” Mary commented.
“It is, he already has a six figure job lined up with a major corporation,” Rob confirmed.
“So was part of the reason he went there problems with relating with girls, and did it help him with that?” Mary asked.
“Yes, and it did help quite a bit. He had a couple of girlfriends in the last year,” Rob said.
“Any sex?” Mary asked.
“With them? I don’t know, he wouldn’t have had any reason to tell me. He stopped using the university system in the last semester, so I think he was getting serious with Cathy,” Rob replied.
“Well, good, I was sort of hoping that’s the way WHORES would help. I’m finished dusting, let’s have a seat on the couch,” Mary suggested.
Rob sat down on the couch, and Mary took a seat right next to him, noting Mr Happy rising in appreciation.

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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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