It was Saturday December seventeenth 1988. Tyler was playing a video game when his mom came down the stairs. Her high heals clicking quickly across the hardwood floor as she was making her quick exit from the house. He paused as I was sure she was going to give him more instructions about dinner and what time she'd be back. She looked at her self in a nearby mirror and gave one more adjustment on her black mini-skirt, and of her breasts before turning towards him, to fill him in on tonight's plans.
"Tyler, I left 20 dollars on the counter in case you'd like to have a pizza for dinner, but there is plenty of leftovers in the fridge and TV dinners in the freezer. I don't know when I'll come home from the office party, but I'm sure you can handle the house on your own." She smiled.
"Yes, Mom, you have fun tonight."
"I'm sure I will." she said giving him a kiss on the forehead. The smell of her hair spray filled his nose so much that he coughed. "Sorry." she said as she backed away and headed out the door.
Tyler continued playing for a while before finally getting hungry and called to order a pizza. Every December was like this as far as he could remember, she'd go out to the office party and have a few drinks, and would come home before midnight, but as the years went on she would come home later. He knew what kinds of things would go on at these parties from stories he'd hear and that he was sure that the party would never really go until 1am. But his mother was single and he'd do the same thing in her position.
When the pizza showed up Tyler turned off the game system and put on a movie. Tyler sat back in his underwear and enjoyed the pizza and the movie. His mother has seen him in his boxers before as it would be what he wore on weekend mornings during breakfast. Tyler was always cautious to make sure his penis was well inside them, but now that she wasn't home he didn't care, and it felt nice not to worry about how he looked when he was comfortable.
After almost all the pizza was gone, Tyler decided it was about time to get to bed. He knew that his mom would be home eventually and there was really no point in him staying up too late, and if she brought a guy home, it might be awkward for him to still be there in the living room.
Tyler was awoken at three in the morning when his mom came home. He could tell she was intoxicated just by hearing the way her shoes sounded hitting the floor. He heard as she dropped them off on the floor and began walking up the stairs to her room, part of him wanted to make sure that she'd get to bed safely, but he knew he had to trust that she didn't get that drunk. When he'd get drunk, he would just crash on the couch, but that was because the stairs frightened him when even walking on solid ground was difficult. He respected his mom's bravery for making it up to her room.
Later that morning Tyler decided to make breakfast for his mom, to once again show some independence and to show her how much he cared for her. The smell of frying bacon filled the kitchen and he hoped it would the rest of the house as well. He set some coffee to brew as he was sure his mom would need a mug of hot black coffee. He put the bacon on a plate and used the grease to help in making some pancakes. He was sure his mother would enjoy his efforts and would like to be out of the house for the night more often.
"Ty, what are you doing?" He heard his mom ask as she walked down the stairs.
"Making breakfast Mother, How was your night?"
"It was Ok, it was nice to be able to leave you here all night on your own. It looked like you handled it well."
"I sure did Mom, thank you for trusting me."
"I probably should have done it years ago, I just don't know how to let go of my little boy sometimes."
"It's ok Mom. I just hope that you realize I'm a grown man now." He said as he placed the mug of coffee and plate of bacon and pancakes in front of her.
As he placed the items down he looked down her blouse and admired her cleavage, she had a nice tan on her tits and it matched the rest of her body, they looked firm for a woman of 45, but he knew she took care of herself in order to still pick up men for dates. He pulled his eyes away before his mother noticed his gazing eyes.
"Who brought you home last night?"
"Amanda, she's also bringing me to work tomorrow so I can pick the car up. I really didn't mean to get that drunk."
"Well, why did you?"
"Well, at first it was just something to do to be social, but then after a while everyone started talking to each other, even Amanda was chatting up the boss for a while, so I drank just as something to do and before I knew it I was trashed. Amanda was nice enough to take me home before I made too much of a fool of myself. I just don't think the guys view me the same way as they did 5 years ago and it's kinda depressing." She looked into his eyes, "I'm sorry, I guess I'm saying too much."
"It's ok Mom, and you're still beautiful to me. It's not your fault that others don't see it, and I would love to be able to date a woman like you." He was shocked at how honest he was, but his mother just looked up at him and smiled.
"Why don't we," she said, "It's been a while since I've been out on a real date, and I'm sure you know how to treat a woman."
He chuckled, "I sure do, you taught me well." She smiled back at him and the two went on enjoying their breakfast.
The whole day he spent time watching TV with his mother. She changed from her outfit from last night into a pair of sweats so that she wasn't showing off as much leg and cleavage. Even though she wasn't wearing something as form fitting, he still thought she was beautiful, her hair was a messed up version of the high hair sprayed version that it was last night, and the blush on her cheek appeared to be lightened and spread further across her cheeks. He tried not to spend too much time looking at her as he was worried that she would think his motives for the date were not pure. But when she would catch him looking, she'd lightly smile to herself, as she was still happy to catch the eye of someone half her age.
That evening Tyler headed up to his room to get changed into something a bit nicer than t-shirt and jeans which would get him through most Sundays and into a nice pair of black slacks and a white dress shirt. He was going to make sure he looked his best and added some gel to his black hair in order to make it look good and stay in shape throughout the night.
His mother was in her room getting dressed after her shower to get rid of the hair spray and makeup from the night before. She felt nice and refreshed as she went to her closet to find something to wear. As this was dinner with her son, she thought that she should go with a long gown, but as it was also a date, she wanted to go with something that she would have worn on that occasion. It was black dress that went down to her knees and was a bit low cut in order to show some cleavage, but not too much that she'd feel uneasy around her son. She put on a pair of nylons and black high heels and went down stairs to see him.
He was waiting for her as she walked down the stairs. He noticed how wonderful her legs looked and how much time she took to get ready for this date, even though it was more like dinner with her son. "Wow Mom, you look stunning." He said as soon as she reached the first floor.
"'Stunning' Really?' She said smiling and a slight blush coming to her cheeks.
He went to get the door for her and followed her out to his car. He repeated his gentleman gestures to let her into his car. He got into the driver's seat and took her to the nicest restaurant he knew.
It was a restaurant that wasn't too fancy as he didn't want to make a reservation or think that he could at such a short notice. But it did have candles on the table and his previous dates have always enjoyed the special feeling that he was treating them well, he could tell by the wide smiles on their faces and how there would be a second date soon after.
They were lead to their table and Tyler quickly went to pull his chair out for his mother. She smiled at him as she sat down and smoothed out her dress. Tyler went over to sit across from her and look over his menu. As soon as he made up his mind he put the menu down and found his mother looking at him.
"Thank you Tyler, it's been a while since I was treated on a date like this."
"No problem Mom, you deserve it."
"Please call me Anna tonight."
"Ok, Anna, you deserve it because you are the strongest woman I know and the kind of woman I always hope that I can find."
"I'm sure you can Tyler, but what makes a woman strong to you?"
"Well, I'm sure it wasn't easy raising me on your own, and that really says a lot about you. You chose to take up the challenge and I think you've done a great job of it."