This contains material of a sexual nature not suitable for anyone under 18.
Editing contributions by Literotica member Private1stClass and Simon Brisco vastly improved my story. Thanks!
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4 Part Series
Chapter 1
Jimmy Makes Suzy 'His'
His name was Jimmy and he was both a lucky guy and a truly nice guy. Jimmy was a year out of college with an engineering degree who worked at a small manufacturing company specializing in aerospace electronics.
He was sitting at his parents' kitchen table idly turning the pages of the morning newspaper and enjoying a mug of coffee.
His mother interrupted his random thoughts, "Jimmy?"
(At work, at school, etc he was 'James' or 'Jim', but it seemed that girls and women always called him 'Jimmy'.)
"I need to ask you a question."
"Sure, what's up?"
His mother asked, "You remember Suzy Martin?"
How could Jimmy forget Suzy! Suzy was his mother's best friend and a very good looking lady. For years, mostly on Friday night, Suzy and her husband, Dick (now ex-husband) had played board games (Scrabble, Monopoly, Trivial Pursuit, and the like) with his parents. From the age of 12 or so until Jimmy went to college, Jimmy had filled in as a substitute player when drinks needed to be made, snacks/desserts served, or whatever. And Suzy was more than just attractive; she was smart, personable, and very sexy.
His mom continued, "You know, since Dick dumped Suzy, she has had a very difficult time socially. Financially, of course, she did well in the divorce and her business was thriving. Well...you know...she hasn't met any men who aren't jerks or worse! And you know how I love our 'Game Nights'; it's just not the same with just three players," she replied with a hint of a pleading in her voice.
Then with some intensity as she touched his arm, she asked, "Tonight's 'Game Night'! Would you be Suzy's partner? It would be fun....You would have a good time!"
"Of course, I will," Jimmy replied, "It would be fun!" Jimmy pondered a moment and recalled out loud, "Geez, I haven't seen Suzy since... was it...your Christmas Party two years ago?"
His mom's question prompted him to remember Suzy and that Christmas Party. Jimmy had danced with her at that party and she looked fabulous. He remembered with regret that his date that night was Judy and he was hot after her then. What a disaster Judy had been, eager in bed, but a real short attention span co-ed: immature, demanding, and expensive. His habit of overthinking the meaning of his feelings and his hesitation to act on them really complicated his relationships with these kinds of girls. They took advantage of him, using him for sex, attention, money, and not giving him much beyond a quick fuck.
Maybe he made a mistake ignoring Suzy that night after a nice dance and after she seemed interested in chatting with him that night. But in those days, he was chasing skirts without much forethought beyond sticking his cock in a hot cunt. Sadly Judy was not the last time he got laid and ended up with a real problem child out of the bedroom. He made a mental note that it was time for him to express and act on his emotions.
Thinking about Suzy also reminded Jimmy why he wanted a large mug of coffee this morning-- Becky Phillips last night. Becky was a senior at the U and they had mutual U City friends. Jimmy had called her and invited her to dinner for last night. She suggested that new place Fredrico's. The Italian food had been good and pretty pricey. Becky had ordered the full menu: wine, appetizer, pasta, fish, and dessert. And then she only picked at every course. She was hot eye candy in a form fitting short red dress with a waist that emphasized her firm and perky breasts. She excited Jimmy and stiffened his prick.
Back at her apartment, she responded to his caresses. He peeled her dress off and tried to kiss her inner thighs to really get her going. Her titties were not large, but they were enticing. He tried to kiss them and massage her nipples. Becky was impatient and pulled him on top of her. The missionary fuck was mediocre and the blow-job after, the same. She didn't seem interested. When she got cranky and complaining, he bolted.
This morning all he had was a big credit card charge and a slight hangover. Maybe it was time he told women what he wanted and acted, rather than holding back and trying to gauge their reaction to his actions? Maybe it was time he tried interacting more with real adults, not immature girls? Jimmy chuckled to himself; did that mean he was thinking of older women....like Suzy, maybe?
Suzy must be about 38 or so, a few years younger than his mom, and a MILF for whom he certainly had lustful thoughts as a teenager. She lived just a few blocks away. Then she had been married to physician like his dad (and this Dick was truly a dick whom Jimmy never liked). She was gorgeous with auburn hair and green eyes, he mused. She must be 5'6" or so, 130 lbs., with a great figure, maybe around 35-26-36, he guessed. With smooth pale skin, personable, and always fun to be around....quite a package, for sure! Her voice even turned him on. Suzy could get breathless and husky when she talked to Jimmy. Jimmy always felt that she gazed deep into his soul when she spoke to him like this.
His mom interrupted Jimmy's musings, when she responded with intensity, "GREAT!"
His mom also had Jimmy intrigued. She was being mysterious and appeared a little too eager, looking a little hot and bothered. What was this about? Jimmy's mother was a real fox too and he certainly confessed that he had viewed her in an unmotherly fashion a few times.
She paused and laid her hand on his arm pulling him towards her and out stumbled another question, "...I need to ask you more, something that I want to ask you tonight, but I won't if your answer is 'no'...so...I need to ask it now."