This is the third installment, some of the below may not be understood unless you go back and read 1 and 2.
All characters are fictional, any resemblance to any living or dead person is unintended.
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Matt drove down the long drive and really did hate to leave. Aunt Rebecca had been the busting of his virginity. He hadn't really had a plan, just the lingering desire from all those years ago. It had become more than he could have dreamed of. He knew she'd be upset about the money but she needed if far more that he did and he knew with a certainty she'd spend it wisely.
His next stop was in southern Minnesota near Blue Earth. It wasn't far but when he arrived he didn't feel like calling relatives to tell them he was in town. They weren't expecting him on an exact date anyway. Instead he decided to get some supper and have a drink. Tomorrow would come soon enough.
It was after 8 pm when he got to the RV park just outside of town and set up, That finished, he went out looking for supper. After passing some chain restaurants along the freeway he detoured into town and found what looked like a nice little local diner. Other than the middle aged brunette behind the counter and the guy in the kitchen, it was deserted.
"Pretty quiet in here tonight, I hope that doesn't reflect on the food," he said as he looked around.
The woman smiled and said, "No, our food is great, it's just late and we close at 9:30."
Matt looked at his watch, it was 9:15 pm. "Oh, I didn't notice the time, sorry," and turned to leave.
"Hang on handsome," she said, "we'll take good care of you."
He cheerfully turned to her, "Well thanks gorgeous," he said with a smile and then she showed him to a booth picked a booth. She handed him a menu and asked if he'd like a drink.
He absentmindedly pretended to scan the menu but his mind was thinking, "No wedding ring," and then saw a ring on her right hand. The ring looked like a wedding ring.
"Probably divorced, separated, or widowed," he thought to himself.
"What'll it be handsome?" she asked.
He looked at the menu and asked for a draft import and a rib eye.
Matt took stock of her as she walked away. She was dressed in a stereotypical waitresses knee length dress. Must be in her mid 40's, 5 ft 6 ish, 140 lbs, decent figure, motherly hips, curly shoulder length black hair, nice calves, dark nylons, white flat work work shoes the type worn by people who spend a lot of time on their feet. She got his beer and was walking back.
Continuing his assessment... full breasts, probably a 36D, something familiar about her. Hair, eyes, walk, he couldn't put his finger on it.
She caught him looking at her tits as she approached and said, "You have me completely naked yet?" she asked.
Think fast, "Uh, not quite yet, you've still got your bra and panties on." he said.
She countered with, "You're assuming I wear them," she said with a wink as she put down his beer,
"Touche" he said.
"What brought you to town?"
Matt smiled and said, "Just passing through. I'm on a trip back east," he lied.
She laughed and said, "Good thing. This city is dying. The only thing keeping me here is the amazing retirement system," they both laughed and she continued, "no, really it is this my diner. My husband and I bought it about 15 years ago. He passed about 6 years ago, couldn't sell it so I've been running it ever since."
It was a familiar but sadly not an exclusive story in this part of Minnesota.
"I'm sorry for that, are you doing well?" he asked .
"Oh, don't be sorry. We're holding our own, if it weren't for friends and family... " she said and after a bit of chit chat went to get his steak.
As she set down his meal he held out his hand, "I'm Jack" he lied, he was being careful. There was that nagging feeling so he finally asked, "You are so familiar to me, have we met?"
She took his hand and shook it gently saying as she looked him over, "I'm Connie and if we'd met I'm sure we'd both remember."
There was a loud cough from the kitchen.
She turned in that general direction and yelled, "That'll be enough out of you." Connie turned back and rolled her eyes as she shook her head.
"No one with that name in the family," he thought to himself, "No Connies, no Constance, hmmm, just coincidence?"
He gestured to the seat opposite him and she sat down. They talked for a while as he ate his steak.
"Damn, this is good," he said. A few lights went out back in the kitchen and he heard
"Have a good evening., uh... CONNIE."
"Thanks Frank, see you tomorrow," she shouted back. She reached to the window and turned the OPEN sign to CLOSED. "Frank is one fine cook, none better around here."
"Damned fine steak Frank!" Matt/Jack hollered toward the kitchen.
"He's long gone, door never hits him in the ass." she said.
Matt/Jack looked at his watch, 10 pm.
She sat back and appeared to be sizing him up. Then she smiled and said, "So, handsome, what are you doing after I get off work?"
Matt/Jack looked up a bit surprised, no camouflaging what she wanted to know so he decided to jump in with both feet, "I usually watch hockey or fuck, and it's not hockey season, so..."
The rest was left unsaid. Matt/Jack finished his meal as she studied him. Idle conversation covered what would otherwise have been an odd silence.
Connie stood up and stepped to his side. She leaned over and she reached into his crotch to grab his cock. She squeezed, smiled, and walked away saying over her shoulder, "Pick me up out out back, handsome."
"Now why would I do that?" he asked playfully.
"Never no mind to me, but you'd be sorry if you didn't meet me there.." She said as she walked to the door and waited on him, then added, "I promise."
He got up, walked out and she locked the door behind him. He pulled out his phone and accessed his coach via the internet, remotely turned on the lights and heater so it would be welcoming when they got there. Then he pulled around back and there she was.
She had put on a long blue coat, as she got into the car he caught a flash of her calf.
She didn't settle into the seat but rather turned toward him, placed her right hand on his thigh and leaned in to kiss him. Matt/Jack kissed her back as her hand found his cock. It was pretty clear she was sizing him up.
She bit his tongue and broke the kiss, saying, "You'd better drive," as she unzipped his pants.
Matt/Jack pulled out onto the main road just as she pulled his cock out. She stroked it a few times, looked at him and then dove to his cock. She licked the tip, swirled her tongue around it, and then took only the head into her mouth and sucked... and sucked.
"God Damn woman," he said to her and reached down with his left hand and moved the seat back a few inches.
She reached inside his pants with her right hand, cupped and squeezed his balls, and started to bob up and down on his cock as he drove.
It took about 15 minutes to get to the RV park where the coach was set up. When he parked the car she was still locked onto his cock. She looked up and smiled at him, wiped her mouth and got out of the car. She was masterful and had brought him right to the edge several times and then stopped. He stuffed his cock back into his pants and stepped out.