Chapter 8: Dating

“When do you think you’ll get home?” asked Jessica.

Toby gave a mild shrug. “Depends.” He was examining himself critically in the hall mirror.

“Depends on what?”

Toby grinned broadly. “On whether Teresa’s father gives her a curfew.”

Jessica rolled her eyes at her son’s response. Now that school was out, he could date any night he could get a girl to agree, and he was remarkably successful at that. He had gotten a part-time job delivering pizzas for a local pizza parlor, making just enough money to pay for a few dates a week, provided he didn’t spend much. This weekend he had off, and he intended to make the most of it. “You should take her home by midnight.” she replied in a scolding tone.

Toby just grinned again. “Now, what about my telling you about all the gory details, so you can reenact them with me later? Besides, we’ve gone out before; she knows my capabilities. She might not let me go home until dawn!”

“Jesus save me!” groaned his mother. Toby just laughed. “You just remember what I’ve told you.”

“Yes, Mom, I’ll lick her pussy and suck her clit twice as long as she wants me to.”

“NO!” Jessica swatted at her laughing son. “Well, yes, but what I said about drinking and driving. No drinking or drugs or anything like that. I’ll kill you, and then you’ll have to explain it to your father!”

“Yes, Mom!” Laughing, Toby headed out the front door.

“Lord, preserve me!” she prayed quietly.

Her youngest son laughed at her from the living room. He wasn’t dating yet - the lack of a car being a major obstacle (Daffy had moved on to another boy, one with a car) - but had been out on some ‘walks’ with a classmate from a couple of blocks over, Tracy Helder. Those walks had gotten fairly intimate, with stops in a few nearby wooded copses, involving plenty of kissing and petting, but hadn’t quite made it into the realm of fluid transfer. Jessica had volunteered to relieve any anxiety generated by these walks, saving her son from the dreaded curse of ‘blue balls.’ He had promised to tell her when things got more involved, so they could act it out at home later.

“It looks like it’s just you and me tonight, Mom.” Jessica wandered into the living room where her youngest child was sitting on the couch. She sank down next to him.

“Tracy busy?”

“She’s got to go with her parents to Oklahoma for the week. She wanted to stay, but they wouldn’t let her.” he answered.

“I think I’d want to stay, too, if the alternative was Oklahoma. Still, she’s too young to stay a week on her own.” said Jessica.

“Oh, I know that. I offered to let her stay with me, but she said her parents wouldn’t let her.”

Jessica laughed. “You’re such a selfless hero!” Andrew affected a modest and self-effacing look, which didn’t fool her for a moment. “Well, don’t worry. I’m sure that after a week away from you, she’ll want to make up for lost time.”

Andrew nodded slyly. “She pretty much told me that already. This wouldn’t have been a good week, if you get my drift, or so she said anyway.”

Jessica rolled her eyes at her youngest. They had all suffered through that the previous week. It was a time that made her bitchy and the boys reverting to jerking off for a few days.

“She pretty much told me that when she gets back, we’ll be getting a whole lot more serious.” he continued.

“She seems like a very nice girl. Just remember everything I’ve taught you, and make sure she cums at least twice for every one of yours. Even if this doesn’t work out, it will pay off in the long run.”

“Huh?” said Andrew, confused.

“Honey, girls talk as much as guys do. If you do a good job with a girl, she’ll tell all her friends. It’s a good reputation builder. When I was in school, if a guy kept his girlfriend satisfied and happy, when they broke up, her friends would chase him down for a shot themselves. How do you think I got your father?”

“What? You never told us this!”

“Well, I did tell you I asked him. It was just that he had broken up with a friend of mine, who was cheating on him. Anyway, she had told all of us that a night with him was like a week with any other guy, so when they broke up, I pounced. She was right, too!” she said with a dreamy smile.

“Wow!” Andrew looked at her with a smile. “Did you really go out on your dates without any underwear? Did your parents know?”

Jessica laughed. “Yes, I did, and yes, they did, too.” Andrew’s eyes widened at this. “Well, they suspected anyway. I mean, they could tell I wasn’t wearing a bra, but they didn’t try looking up my skirt. Daddy wasn’t any too thrilled, but Mom understood.”

“Oh?” Andrew tried to imagine his grandparents being understanding, and totally failed.

“Well, I was the last one still in the house. I was the baby and my brothers had both gone off to college by then. So, when I went out, it was just your grandparents still at home. Mom told me once that when I went out, she would fool around with Daddy. He was a lot calmer by the time I got home.”

“Cool!” laughed her youngest.

Jessica looked at her son with a smile. “And what else did I tell you about your dates? About afterwards?” Andrew gave her a confused looked and stumbled out several false starts. “You know about the next day, with your buddies?”

His face cleared up. “Oh, yeah, never say anything. Mom, I wouldn’t!” he protested.

“Of course, you would, you’re a male. You guys are always bragging about some sort of crap. Believe me when I say, we hear all about it. You talk trash about your girl, it will get back to her and you won’t be getting any from anybody. God’s honest truth!”

It was Andrew’s time to roll his eyes. “So, what’s the plan for tonight?”

His mother smiled at him. “Well, it’s just you and me, isn’t it? Did you want to watch anything down here, or go upstairs and watch something there?” Jessica had a television in her bedroom and had already shown her sons where she kept a small stash of porn from when she had been married.

Andrew’s eyes lit up at this. “Uh, maybe upstairs.”

Jessica laughed. “Maybe. We’ll need to get you two boys extra well satisfied tonight. Tomorrow, your Aunt Jane and Billy are coming for a week, and we are going to have to be a whole lot more discreet.” Every summer, Andrew Sr.’s sister and her son would visit for a week.

Andrew grimaced at this. Unlimited sex was such an incredible thing to him that the idea of a week with nothing but jerking off seemed like forever. He liked his aunt and his cousin, but an entire week without being able to get his rocks off was horrendous! Even Tracy would be away! “Maybe we need to start right away!”

Jessica laughed. “Come on baby, let’s go upstairs. It will be kind of fun, just the two of us. You can practice all the moves you’re going to put on Tracy when she gets back.” She stood up and took her son’s hand. Once upstairs, and in her bedroom, she asked “Do you have any idea where you two plan on doing it?”

“Uh, actually, I do know of several spots over by the other end of the park, very quiet and private. I was thinking of riding our bikes over there for a picnic. If the weather is nice, we could stretch out on the blanket without getting dirty or anything.”

“Okay, so we’ll pretend this is your blanket.” She pointed at her new king-sized bed. Toby had taken her old queen size, but Andrew still made do with the bunk beds in his room. His room would have needed some serious rearranging to put in a larger bed, and he hadn’t felt it was worth it. She kicked off her shoes and scrambled onto the bed, positioning herself near the center. Andrew kicked off his own shoes and joined her.

“Uhh...” Andrew looked at her in confusion.

Jessica smiled patiently. “Just like on your picnic. You’ve had your lunch and now the two of you are sitting next to each other on the blanket. What do you do next?”

“Uh, kiss her?”

“That’s probably a good start.” She puckered up her lips and looked at him with amusement.

“Oh, yeah, okay, Mom.” Andrew puckered up as well and leaned over, to give her a somewhat chaste kiss.

Jessica laughed again. “Tracy, remember? Just put your arms around me and close your eyes. Pretend!”

Andrew was surprisingly nervous, considering that the last several weeks had been a sexual smorgasbord with his beautiful mother. He did as she asked, closing his eyes, and putting his arms around her, to pull her close in a hug. He felt a little stiff with the pretense.

Jessica was enjoying the moment, both her son’s discomfort and the feel of his body against hers. Pressing her body against his, she began to nibble his cheek and neck, and whispered “Oh, Andy, I’ve missed you so much! It’s been so long! I wanted to be with you all last week!” Then she licked his ear and rubbed herself against him.

Andrew groaned. He hated being called ‘Andy’, but it was what Tracy called him and Jessica knew it. Still, Tracy was very pretty, and like most guys, Andrew was willing to put up with a certain level of crap to get laid. ‘Tracy’s’ kissing and body rub had the desired effect, and Andrew’s sense of unease disappeared immediately.