Chapter 4: And So It Begins

February 24, 2000, Chicago, Illinois

“What the heck were you thinking?” I asked testily.

April and I were in my study, and I was giving her a hard time about being with Jesse. I didn’t REALLY have a problem with it, but I did need to make a couple of points with her.

“I thought you’d be OK with it!” April protested. “Jennifer even let me spend the night with Jesse on Tuesday!”

“You’re thirty-four! He’s fourteen!”

“Steve, I’m sorry. I honestly thought you were OK with it! Your first was older than you! I can’t undo it.”

“No, you can’t undo it! And what I did in 1978 is totally irrelevant in 2000! You’re lucky I decided not to call the cops!”

“Oh my God! No!” she gasped.

I couldn’t control it any longer and burst out laughing.

“YOU BASTARD!” April screeched. “You had me thinking you were going to kill me, or worse!”

“I thought you knew me well enough to know it wasn’t an issue!” I laughed. “There is an issue, though. And it does give me a serious concern.”

“My husband.”

“Yes. Your husband.”

“That’s between me and him. I’ll deal with it.”

“No. Now it’s between you, him, AND Jesse.”

“Why? I made it clear to Jesse that this was a once-in-a-lifetime thing, never, ever to be repeated. It was sex, pure and simple. Great, glorious sex!” she giggled. “He was totally aware of the situation. The little brat quizzed me like you did back in the day!”

I chuckled, “What do you expect? He’s my kid!”

“I’ll say!” she smirked. “He met all three challenges just like his old man!”

“Jesus, April!” I laughed. “His first time?”

“It’s your fault, you know?”

“How is it MY fault?”

“He told me, when we were talking, that he wanted to do everything that he saw you do with me!”

“Oh hell,” I laughed. “You know I only found out later that he’d been spying.”

“Jennifer told me at some point years ago. She found it amusing.”

“I’m sure she did! But I had my revenge!”

“Oh?” April asked, arching an eyebrow.

“On Jen,” I grinned. “But that’s between her and me.”

“Jesse was more than a little surprised about the third one. I guess from his perch on the stairs and being only three, he had no idea where you put it!”

“I think we’re treading heavily into ‘Too Much Information’ territory!” I chuckled.

“Then I’ll just add that he can give his old man a run for his money. And I taught him the same thing you told me your first taught you.”

“Now I KNOW we’re in ‘Too Much Information’ territory!” I said, but I was laughing hard.

But then I stopped. I had an important question to ask. A serious one.

“Tell me if it’s none of my business, but what about your husband? I’ve been pretty adamant with Jesse about girls who are taken.”

“Tell me, Steve, at age fourteen, would YOU have cared if your first had still been married? Answer truthfully now.”

I chuckled, “No, I don’t believe I would have. The sense of self-preservation came later. Much later!”

“Donny will never, ever know. I’ve wanted to do something like this for years, but obviously Jesse was too young. And I don’t mean I was thinking about HIM that way. I just wanted a virile teenage boy that could go as many times as I wanted and would do anything I wanted. The teaching was fun!”

That was very different from my experience with Jennie McGrath, now Jennie Sanders. There, it had been a combination of her needing intimate contact, and being attracted to me. There was an emotional connection, though she’d wisely broken things off before it got out of control. I was sure Jesse would come talk to me at some point. I knew what had happened because I’d seen April leave the next morning and had asked Jennifer about it. I had raised the issue of April’s husband and Jennifer had simply shrugged and said it wasn’t really our business.

“It still concerns me.”

“You obviously impressed on Jesse how important an issue that was. We talked for a good twenty minutes about that before he’d even kiss me! Talk about frustrating!”

I smiled. He really was following in my footsteps in that way. I’d been told I was frustrating by more sex partners than I could count!

“As long as he thought it through and made his own decision.”

“I didn’t push him, if that’s what you meant. I simply asked him if he would like a sexy kiss for his birthday!”

I laughed hard, “You asked him to have sex with you, you dope!”

“What?”

“When Jesse was little, say from age two to age five, he equated kissing with sex. I guarantee you that connection came back because of who you are and what he had seen when he was three!”

“Oops!” she laughed. “I suppose I did. Well, it doesn’t appear to have done any lasting harm.”

“I’m sure that it didn’t.”

“I’ll make it up to you,” she smiled.

“You’re married, and that is a line I won’t cross, even for a woman as sexy and fun as you are.”

“Not me, silly. My girls. When the triplets turn fourteen in five years, I’ll tell them who to go to for their first lessons!”

I just shook my head, amazed at the way pussy literally fell into my lap at times.

“You know they have to decide that for themselves, April. Not you. Not me. Them.”

“I’ll simply let them know that if they’re in need of an ‘Expert Deflowering’ you’re the man to see!”

“Seriously?!”

“I believe I popped your son’s cherry, well, all three of them! How could I possibly object? I do listen to things you say!”

I chuckled, “Just remember, though, no pressure. That’s not how it works.”

“I understand. And Jesse has somebody else in mind. I’m yesterday’s news!”

“I figured he might have talked to you about it.”

“I gave him some advice, which I think matches what you’ve told him, but from a girl’s perspective.”

“One question.”

“Sure.”

“Who told you it was OK in advance?”

April smiled, “You want me to rat someone out?”

I shook my head, “I’m not upset, nor will I say anything, I just want to know that you made sure it really WAS acceptable before you went all ‘cougar’ on my fourteen-year-old son on his birthday!”

“Josie. You know that Jesse and I flirted and teased lightly once he grew to be man-size. Josie asked me what I was doing and we had a talk. She gave her approval, provided it wasn’t before he turned fourteen.”

I nodded, “Then we truly have no issues.”

“He’s good, Steve,” April smirked. “He got me there without having to resort to his mouth!”

“Get out of my study!” I ordered with a laugh.

We both got up, exchanged a chaste hug, and she left.

February 26, 2000, Chicago, Illinois

On Saturday morning, I dressed in jeans, a t-shirt, and a warm sweater, then got the box of rubbers my dad had given me from my desk and went downstairs. I put the rubbers in my coat pocket, then put on my boots, coat, hat, and gloves.

“I’m going out now,” I called to my moms.

“Remember you have hockey practice at 2:00pm,” Mom Two called back.

“I remember! My gear is airing out on the rack in the basement. I’ll be home in time to pack and eat before we go.”

“OK. Have fun, Jesse!”

“Bye!” I called back.

I went out the front door which led to the alley and started walking south through the light snow which had fallen. It took about ten minutes to walk to Francesca’s house. My moms knew where I’d be, because I had to tell them or risk getting in serious trouble, and they had warned me to be very careful.

When I got to Francesca’s house, I looked around to make sure nobody was watching, and to make sure her parents’ cars were gone, then walked up the steps to the back door and let myself in as she’d said I should.

“Honey, I’m home!” I called out, as my dad sometimes did when he got home from work.

“Jesse!” Francesca squealed.

She came running to the back foyer and almost knocked me over with a hug. I hugged her back and we kissed, but I needed to take off my winter gear. I lowered my arms and Francesca did, too. I took off my gloves, hat, coat, and boots, and got the box of rubbers from the coat. Francesca grabbed my hand and tugged.

“Come on!” she insisted. “I’ve been thinking about this all week! How many rubbers do you have?”

“Three!”

“Only three?” she pouted.

I smiled, “I can get more, but Mom One and Dad both said that it might hurt the first time, and you might not be ready to do it again right away.”

“You told?!” she gasped.

“You know I couldn’t be here unless I told my moms where I was going. If I ever lie about that, I’m dead meat and I’ll never be able to do anything! And remember, I had to ask my dad for the rubbers. I didn’t say who I was going to be with, but he’s smart and I’m sure he figured it out!”

“But if they tell...”

“My moms or my dad? Are you kidding? No chance!”

“If you’re sure.”

“You know what my dad thinks about your mom, right?”

“That she’s dumb because she thinks she can stop us from having sex, but he knows she can’t stop us if we really want to!”

“So why would he tell her?” I asked.

“Sorry,” Francesca said. “Let’s go to my room!”

I followed her up the stairs. I’d been in her house, but I’d never been allowed to set foot on the stairs, let alone go up to the floor where the bedrooms were. Her house wasn’t as big as my dad’s, but it was bigger than the coach house, and she had a big bedroom with a bed with a canopy over it. I groaned softly because everything was PINK, which reminded me of a certain annoying little sister’s room.

“You don’t like pink, do you?” Francesca asked.

“Not really.”

“Maybe I can distract you!” she said.

She pulled her sweater over her head, which let me see her boobs because she wasn’t wearing a bra! They were smaller than April’s, but they had large, puffy, brown nipples that seemed to beg me to suck on them. I pulled my sweater over my head and dropped it on the floor, then did the same with my t-shirt. Francesca giggled nervously and pushed down her sweat pants, and revealed light brown pubic hair. She also wasn’t wearing panties! I wasted no time taking off my jeans and briefs, revealing my boner which was pointing straight up.

“Wow, Jesse!” Francesca said in awe. “It’s really big!”

I held out my arms and she took three steps, threw her arms around me, and we kissed, our tongues playing with each other. I put my hands on her butt and pulled her against me, her soft brown pubic hair tickling my dick which was smashed between us. Francesca stopped kissing me after a minute and she was breathing hard. She moved a bit and I let her go. She pulled down the pink bedspread and pink blanket to reveal pink sheets. I wanted to roll my eyes but I knew that was a bad idea!

Francesca got into bed and I got the rubbers, put the box on the table next to the bed, then got in next to her. We turned to face each other and kissed again. I ran my hand over her hip and butt, then up her side, and finally to her boob. I cupped it, now without having to fight her sweater or bra, and I wanted to kiss it the way I’d kissed April’s!

I stopped kissing Francesca, gently pushed her to her back, and put my mouth on her puffy nipple and ran my tongue over it before I started sucking softly.

“Oh, Jesse,” Francesca sighed, “that feels so nice!”

I felt her fingers in my hair, which I wore like lots of pro hockey players did - long in the back. I moved my hand to Francesca’s hip, then slid it over to her soft hair and twirled my fingers in it. I slipped one down between her legs and she gasped.

“Ooooh!”

I put the tip of my finger over where I knew her clitoris was and pressed gently. Francesca squeaked and pulled my head down. I ran my tongue over her puffy nipple and gently rubbed her between her legs.

“Jesse, it feels so good,” she whispered, then shuddered and groaned, “Ungh!”

‘That was one!’ I thought to myself, and switched to her other boob while I rubbed her gently between her legs. It didn’t take long before she shuddered and groaned. ‘Two!’ I thought. I wanted to taste her, and wondered if she would taste the same or different from April. I removed my mouth from her boob and kissed her breastbone.

“Jesse,” she whined. “I liked that!”

I didn’t think she’d whine once I started doing what I wanted to do next! I kissed her stomach, rubbed my nose in her pubic hair, and then kissed the skin that covered her clitoris.

“Oh!” she gasped. “Jesse, are you sure?”

I looked up, smiled, then stuck my tongue out and licked her from the bottom of her pussy lips to the top.

“Oh!” she gasped. “Do that again!”

I did, and she gasped again, but then I pressed the tip of my tongue between her pussy lips, finding a very different flavor from April, almost like copper. I licked upwards until I touched her clitoris and she nearly jumped out of the bed.

“What did you do?” she gasped.

“Don’t you rub yourself?” I asked.

“Yeah, but just, you know, outside, on top.”

“That’s your clitoris, but some people call it a button or clit,” I said, remembering what April had taught me. “And this,” I pressed on it with my tongue causing her to squeak and jump, “makes you feel really good!”

“It’s not gross?” she asked.

“I like how you taste,” I said, pushing my tongue into her to get more flavor.

“Oh, Jesse, do that more! You know, on that spot!”

I lowered my mouth to her pussy, closed my lips around her and sucked softly while I ran the tip of my tongue over her clitoris. Francesca moaned, gasped, and groaned, and I felt her hand on my head, pushing me down onto her. It didn’t take long before her body shook. ‘Three!’ I thought.

“Jesse!” she squealed. “Keep doing that!”

I did and counted ‘Four!’ and ‘Five!’ before I couldn’t wait any longer, and stopped licking her.

“You stopped!” she whined. “I liked that!”

“Don’t you want to?”

“You mean sex?” she asked, breathlessly.

“Yes.”

“I do! I want to! Hurry!”

I moved up and opened the box of rubbers. I took one out, very carefully tore the foil packet open, and took out the rubber which had some kind of slippery lotion on it. I looked at the back of the box for the instructions and managed to get the rubber on without shooting, which I’d been afraid might happen. I got between Francesca’s legs and kissed her. She made a face.

“Gross!” she said.

“You didn’t think that when I licked you!” I said, remembering what April had said. “Did you like me doing that?”

“Yes!”

“Then you should kiss me!” I said.

Francesca nodded and while we French kissed, I rubbed my rubber-covered dick against her pussy trying to find the right spot. It took a couple of tries before I figured out the right spot because she was really tight. I kept kissing her and pushed my hips forward. The slick lotion on the rubber let me push into her and before I knew it, I felt something blocking me and then quickly give way as I pushed through it.

“Oomph!” Francesca gasped into my mouth and we stopped kissing.

“Wait,” she panted.

I was just about an inch into her, and despite the rubber on my dick, I felt extreme heat, and her pussy squeezed the head of my dick tightly. I waited, though I wanted nothing more than to be inside her.

“OK,” she whispered about a minute later. “Slow and gentle.”

I kissed her and very slowly pushed into her. She was really, really tight, and it felt so good and so warm, and I wished I didn’t have the rubber on, but I did NOT want to have a baby, so there was no way I could take that risk. It took a few minutes to get completely inside her and when I did, I stopped and waited.

“You’re inside of me!” she gasped. “And we’re having sex!”

“Is it OK to move?” I asked.

“Go slow, please. You’re so big you filled me up!”

I kissed her and started with slow, gentle thrusts. Francesca didn’t really move, except to spread her legs as wide as possible, letting me get just a bit deeper. After five thrusts, I stopped kissing her.

“Move your hips,” I said. “Up and down with me.”

Francesca nodded and the next time I pushed into her she raised her hips. She got the hang of it after a minute and wrapped her arms around me, as I felt her heels rest lightly on my butt. The rubber, which bugged me, also made it easier for me not to shoot before I wanted to. We had to stop kissing because Francesca needed to breathe, so I put my head next to hers and continued moving in and out of her.

“Oh,” she gasped. “It feels sooo good!”

She tensed a bit, then groaned, and her body shook. ‘Six!’ I thought as suddenly Francesca’s pussy clamped hard on my dick, she gasped, and started raising and lowering her hips really fast. I decided I should go just as fast.