Jeremy was 23 and in a fuck-buddy relationship with a 53-year old woman at work. It was understood that the relationship was non-exclusive, which suited both Jeremy and Helen fine.
Jeremy had a station wagon and sometimes helped friends move stuff with it. One day a friend named Peter asked if Jeremy would help him move a chair and table set to his recently divorced mother's place from a used furniture store.
Jeremy agreed and the two young men picked up the furniture and took it to the mother's house. They unloaded the stuff and moved it around a few times as she hadn't yet decided how she wanted it set up.
When they were done, Peter told the two of them that he was going to his old bedroom to gather some clothes he had stored there. Jeremy was left downstairs with Peter's mother, Sandra.
Sandra was in her mid-40s and fairly attractive. She was notably short, with small breasts and a ripe-looking ass. She was dressed in an old sweatshirt and sweatpants as she was planning to do a lot of rearranging that day after the young men left.
Sandra made polite small talk with Jeremy while they waited for Peter to come back down. Her cat came by and she bent over to pick up and pet the animal. Jeremy happened to be perfectly positioned to get a good look at Sandra's boobs - the sweatshirt was loose-fitting and she wasn't wearing a bra.
The titties didn't appear to be much more than a handful, and while quite saggy retained some nice fleshy shape. When Jeremy saw her very thick, hard, and outsized nipples he got an instant hard on. Sandra stood up while stroking the cat's head and her gaze fell on Jeremy's erection, which was now tenting his jeans. She seemed to give a flash of a smile, and then Peter returned from upstairs, carrying a gargage bag full of clothes.
Jeremy and Peter made to leave, but Sandra said she wanted to make them dinner the next night in return for bringing her the furniture. The two of them were fried egg sandwich-level cooks so they quite happily agreed.
The next night, Jeremy and Peter returned to Sandra's place and she'd prepared a superb seafood pasta dish. Sandra only had a bit ("Gotta watch my figure!"), but the two friends stuffed themselves and helped Sandra through two bottles of wine. Later, Peter excused himself to pack up some more clothes and some books to take back to his place.
This left Jeremy and Sandra in the dining room. A little tipsy, Sandra told Jeremy that she'd enjoyed his company, adding, "You'd think I'd know better! Peter's father came home early one afternoon when we were married and caught me screwing the kid from the warehouse where I work. There he was, fucking me like a madman, and my husband walked in here. The kid came inside me right in front of Dan. On the one hand I was mortified with cum dripping down my thighs on the living room floor, but on the other it was pretty funny watching the kid trying to get back in his clothes and out before Dan could kill him. Discretion is the better part of valour, as they say!"
Jeremy was flabbergasted to say the least when her heard Sandra's story. He couldn't come up with one of his frequent witty replies, even as the germ of the idea of fucking this pretty woman who seemed very forward about liking to have sex with younger men planted itself firmly in his always horny mind. The mood was broken when Peter came downstairs carrying a bunch of his stuff. The two of them left for their places.
When Jeremy went to bed for the evening, he enjoyed a slow beat-off to a fantasy of humping Sandra. He edged for a long while, before spraying his chest and stomach with a big, hot load of jizz, moaning with ecstatic pleasure. Jeremy couldn't really have dreamed what would come to pass for himself and his friend's mother.
On a warm Sunday a couple of weeks later, Jeremy found himself out of beer. At the time in British Columbia, alcohol was not sold legally on the Lord's Day. Not necessarily a problem for people in Jeremy's part of North Vancouver: There was an illegal speakeasy of sorts in the area run by the mother of a retired motorcycle gang member who Jeremy knew. Drinks and snacks could be had, and take-home booze was sold at a 100 per cent markup from government liqour store prices.
Jeremy went down to the place and was quickly admitted by the owner. He was trying to decide if he'd have a drink in the "bar" before buying beer to take home, when in walked Sandra. Her face actually brightened when she saw Jeremy and she gave him a hug, pressing her soft breasts into his lower torso. Jeremy's cock instantly hardened and Sandra unabashedly pressed her crotch against it while looking directly into his eyes.
"Let me buy you a drink, Jeremy," she said. "OK," he replied, "I'll have a scotch, straight up." Jeremy moved to a chair in the seating area as Sandra got the drinks and brought them over. She sat on a couch near Jeremy's chair and as they sipped their drinks, she brought a foot up and placed it on his erection.
Jeremy smiled and checked out Sandra's shorts. The legs were quite loose and he could easy see her panties by moving his head a bit. Her pubic hair bulged the panties and a fair number of hairs protruded from the side. Sandra noticed Jeremy's interest and nonchalantly pulled the crotch of the panties to the side. "Like what you see, Jeremy?" she asked as he blatantly squeezed his cock over his shorts.
They were the only customers in the speakeasy and the owner was a former prostitute who wasn't easily shocked. Jeremy got off the chair and knelt in front of Sandra. He worked his tongue up to her moist cunt and gave her a few licks. He stopped and stood up, saying, "Let's grab our booze and go to my place."