A Well-Lived Life 2 - Book 3 - Jessica - Cover

A Well-Lived Life 2 - Book 3 - Jessica

Copyright © 2015-2023 Penguintopia Productions

Chapter 15: Beginning, Middle, and End

Coming of Age Sex Story: Chapter 15: Beginning, Middle, and End - This is the continuation of the story told in "A Well-Lived Life 2", Book 2. If you haven't read the entire 10 book "A Well-Lived Life" and the first two books of "A Well-Lived Life 2" you'll have some difficulty following the story. This is a dialog driven story. The author was voted 'Author of the Year' and 'Best New Author' in the 2015 Clitorides Awards.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Fa/Fa   Mult   Military   Polygamy/Polyamory   First   Pregnancy   Slow  

December 27, 1988, Chicago, Illinois

"What on earth do you need your toy bag for?" Kara teased on Tuesday morning.

"What do you think?" I smirked. "My young charge is exploring as much as she can before Saturday!"

"Steve Adams, corrupter of innocent young girls!" Kara giggled.

"She set out to have sex with me when I first offered to be her friend and help her train! I never even thought about her that way until about four hours into our date, and even then, I didn't consider it a real possibility."

"How did she let you know?"

I chuckled, "She invited me in. I thought I was going to say 'good night' to her parents. When they weren't home, I kind of got a clue and said I was going to leave. She insisted I stay five minutes so that she could show me something. I reluctantly agreed. She went up to her room and came back down wearing a relatively modest bikini so she could show off her new body. Then she said she wanted to show me everything and took off the bikini. I was stunned. She grabbed my fedora, put it on and ran up the stairs, telling me I had to come up to retrieve it."

"And you were a goner!" Kara giggled. "A cute, naked, willing seventeen-year-old with your fedora on? I don't think the Pope could resist that!"

"Given the history of popes, I'd have to agree!" I chuckled.

"Have fun while it lasts, Snuggle Bear!" Kara giggled.

"YOU like how long it lasts! In fact, last night, you were done after one time!"

"I was tired," Kara said with a coy pout. "And I miss Jessica."

"Me, too. You weren't like this before Thanksgiving, what happened?"

"You needed me to be strong for you, so I was. Now I guess it's my turn to be upset and out of sorts."

I smirked, "Do you need a dalliance to perk you up?"

"Hmm," she said soberly. "Who would I choose? Kurt, but I have to follow your rule."

"Not if the other couple were completely willing," I said. "Wait, you chose him, so I would think about having Kathy!"

Kara giggled, "Duh! And you know darn well that no other man will ever touch me that way. EVER!"

"And the dancing?" I chuckled.

"It's fun to get Kurt all worked up the way you do Kathy and then watch them drag each other away to fuck. I bet they think about us when they do it!"

"Kara Adams, you are BAD!" I chuckled. "All I can say is whoever Birgit sets her sights on better be ready for the wildest time of his life!"

"There's one person it can never be, Steve. You know that."

"Absolutely! I agree. But I'll bet you anything she's as big a tease as her mother."

"It'll serve you right!" Kara giggled. "Now, go blow your little friend's mind!"

I laughed, grabbed my hat and coat and an umbrella, and walked through the drizzle to Jacquelyn's house. She was waiting at the top of the steps today to have some protection against the light rain.

"Is that your bag of tricks?" she giggled.

"I brought them all," I said. "I'll show you something that'll blow your mind!"

"Get inside!" she hissed. "I'm already wet!"

"Sure, it's raining," I teased.

"If you prefer THAT to this," she pointed to the V between her legs, "you can stay outside! I'm going in where it's warm and I bet YOU want to be in where it's warm!"

I didn't need a second invitation, and sprinted up the stairs and into the house. Ten minutes later we were in her bed, engaged in our normal very slow, very pleasurable screw. There were lots of soft kisses and after Jacquelyn had cum twice, she demanded that I fuck her hard.

"That's ... the ... right ... way..." she gasped. "Slow ... then ... hard!"

It didn't take too long before we both groaned in pleasure as our orgasms overtook us. When they'd run their course, we lay gasping for breath. I didn't get much respite, though.

"Can I do that to you now?" she asked with a smirk.

"Sure," I said, getting off of her and retrieving the harness and smallest dildo from the bag. "We need the Vaseline."

"On the night stand," she said. "I never put it back."

"Come here and I'll help you put this on," I said.

She came over to me and I had her step into the harness, and adjusted it.

"Is this what it feels like to have a dick?" she asked.

"A little, I guess," I said as I handed her the jar of Vaseline. "Spread this on the fake dick. It's called a dildo, by the way."

She did that and then I climbed onto the bed and got on all fours.

"Get behind me, and then you need to rub some Vaseline on my butt, you know, between the cheeks."

She giggled, and I felt the contact of her finger covered with the cold jelly.

"OK. Put the end of the dildo against my hole and push GENTLY," I said.

I relaxed as much as I could and took a few deep breaths as Jacquelyn positioned herself. She slowly pushed the head of the dildo into me, and I groaned softly. It had been quite some time since someone had done this to me. I felt Jacquelyn's hands on my hips and continued breathing slowly in and out.

"OK, you can push a bit further," I said.

Without warning, Jacquelyn pulled my hips back and thrust forward firmly, burying the dildo in my butt.

"Ungh! Ooof! Oh!" I gasped and groaned.

"That was COOL!" Jacquelyn giggled. "Do I fuck you now?"

"GENTLY at first, please!" I gasped.

She was gentle. For about thirty seconds. Then she started to really get into it. If I hadn't been grunting and groaning, I'd have laughed at the monster that I'd obviously created. Somewhere, some unsuspecting teenage boy was going to be in for the time of his life. The only question would be whether or not he survived! As Jacquelyn thrust firmly in and out of me, I thought about Tracey Jones and wondered just how far Jacquelyn would take things.

"Can you cum this way?" she asked.

"Usually not," I said. "You could stroke me, or you could pull out and I'll turn on my back and you can get on me."

"God, yes! Please!" she gasped.

She pulled out, and I turned on my back. She moved and quickly impaled herself on me. She was hotter and wetter than she'd ever been and started riding me like a bucking bronco, with the dildo slapping up and down on my stomach. We both came a few minutes later.

"That," she gasped, "was really wild!"

"You're getting a PhD level course in sex," I chuckled. "Just remember, most of the guys in High School are at the pre-school level. Not all, but a lot."

"Were you?"

I shook my head, "No. I had the benefit of a couple of very good teachers when I was fourteen."

"Fourteen? You did stuff like this then?"

"Uh, not this stuff, with toys, but most everything else when I was fourteen or fifteen. The toys sort of developed gradually, later. I was a Freshman in college when I discovered a girl who was seriously into toys! She's the one who first did to me what you just did."

"Do you do this a lot?"

"Not really. I haven't had my toys out in quite some time."

"What other toys do you have?" she asked.

I chuckled, "Let me show you. Take off the harness and lie down on the bed."

She stepped out of the harness and handed it to me, and I put it on the sink in her bathroom. I got a dildo and the vibrator from the bag and went over to the bed.

"All three holes at once!" I chuckled.

"What?!" she gasped.

"This," I said, holding up the vibrator and turning it on, "goes in your butt. This," I held up the dildo, "goes in your pussy. This," I pointed to my dick, "goes in your mouth."

"Seriously?" she whispered.

"Seriously. And I'll use my mouth on your clit."

"Jesus," she whispered. Then she nodded, "OK."

I got into bed with her and positioned myself so that she could take me in her mouth, which she did. I grabbed the Vaseline and put some on the vibrator and gently inserted it into Jacquelyn's butt. She moaned softly around my dick and jumped a bit when I flicked the switch and turned it on. I ran the dildo along her slit to coat it with her juices, and then slowly worked it into her pussy. When I had it in, I lowered my mouth to her clit and sucked hard.

"Mmph!" Jacquelyn gasped, though it was muffled by my hard shaft in her mouth.

It didn't take long before Jacquelyn had a string of strong orgasms that seemed to go on forever. As she sucked on me, I flexed my hips so that my dick moved in and out of her mouth. As I got closer, I moved a bit faster until I came, filling her mouth with cum. She gulped quickly to swallow it and then sucked gently as the last bits leaked from me. I removed the dildo and vibrator, then carefully got off the bed. I took the toys to the bathroom, then came back and cuddled Jacquelyn for a bit.

"That was just crazy," she said. "I think I'm going to stay in bed all day!"

"I wish!" I said. "I have to go to work, so I can't stay. Want to shower with me?"

We got off the bed and took a hot shower together, then she helped me clean off the toys. I put them back in the bag and zipped it up.

"What else do you have in there?" she asked as we started to dress.

"Soft ropes and a blindfold," I said.

"So, like you would tie someone up?"

"If they wanted that, yes."

"I don't think I'd like that," she said.

"It's OK. I think for the rest of the week, we should just forget the toys and craziness and just enjoy making love."

"I think you're right," she said. "I may have gotten a bit out of control."

"Sometimes that's OK," I said.

"See you tomorrow?" she grinned.

"You bet!" I said, pulling her into a tight hug.

We kissed, and I headed home to have breakfast and get ready for work. Kara teased me a bit about the toys, but not too much, because some of our other housemates were in and out of the kitchen. We finished eating, and I headed to work. I hadn't been to the office in over a week, and there were several message slips in my box. Kimmy wasn't in and there was a note on the whiteboard that said she was on vacation for four days.

I went to my office and went through the message slips and my paper mail. The only really important message was one that I'd expected to receive eventually — Dante Puccini had called. The note in Kimmy's neat handwriting said he was going to be away for the week and I should return the call after the first of the year. The paper mail was a few Christmas cards, plus a sealed note from Kimmy asking me to come to lunch some day during the week. Given that my dad was in town, and I was meeting with Al Barton on Wednesday, it would have to be on Thursday.

I checked my voicemail and there was only one message, a call from Chris Gibson wishing me a Merry Christmas. I was surprised that so few people would leave voicemail, and that most of them simply left messages with Kimmy, which she transferred to pink message slips. I wondered if we should just start using cc:Mail for phone messages and couldn't think of a reason not to.

"Hi, Steve!" Jeri said, coming into my office.

"Did you have a good Christmas?" I asked.

"Yes. My grandparents came to visit. They live in Chicago, too."

That was the pattern for her family. I'd learned over the course of the months we'd worked together that her entire extended family was in the Chicago area. Of course, that wasn't all that different from my mom's extended family all living in the Cincinnati area, except for me, Stephanie, and my cousin Dale, Vickie's oldest brother. That thought brought back very pleasant memories of the Fourth of July, just over ten years in the past. I hadn't heard from Vickie in ages, and I wondered how things had gone for her.

That was one of the downsides of basically cutting off contact with my mom. It also cut off contact with the rest of the family. Mostly I didn't care about that because my mom's siblings were almost as crazy as she was, but my grandparents had always been cool, and a couple of my cousins were OK. The rest? I really was better off without them, especially given my lifestyle.

"Cool," I said, drawing myself back to the conversation with Jeri. "My parents are in town today, and so are Kara's parents. Jesse's other grandparents are here, and Josie's parents will be here tomorrow."

"Wow, you must have a full house!"

"It's pretty crazy! My dad will be here today for lunch."

"I got a lot done last week while you were on vacation. I think we're really close. Let me show you."

We went over what she'd done, read through some 'alpha' notes from Jack and Cassie, and then got to work on the project. Penny came into the office a bit later, gave me a kiss on the cheek, and sat down at her desk. She gave me a look that said she wanted to talk, but with Jeri there, it wasn't possible.

Just before my dad arrived, I stepped out and went down the hall. I used a phone in the small conference room to call Kimmy and let her know that I'd come for lunch on Thursday. She was happy to hear from me and told me she was looking forward to it. I hung up and walked back to my office just as Cassie buzzed me to tell me that my dad was there. I went to reception to meet him, and we headed to a diner for lunch.

"How is Jessica, really?" my dad asked.

"Burned out," I said. "Overstressed, tired, confused, and pregnant. According to Al Barton, that happens quite often. Jess just has a few more stressors than the average PGY2."

"You don't say?" he said with a wry smile.

"Yeah. I know. It seemed like we had it all together until this BS with Carla happened. It's still not over, but there won't be any movement until after New Year's."

"I was really surprised to hear that you aren't the father of that little girl."

"Me, too! I honestly still don't truly believe it. Something just does not add up. Why would Carla press so hard if there was another possible father? And now that the test results are back, if it was all a scam or whatever, why continue? Her attorney told Gwen that they intend to challenge the results.

"Even if we assume it's an attempt to get a settlement out of me, it makes no sense. Let's assume they think I'll cave and pay them. I wouldn't give them more than what it's going to cost Gwen to fight this, and that's far less than 20% of my income for the next fourteen years and going backward four. And I sure as heck am not going to pay her attorney's fees. There's something else going on here, but for the life of me, I can't figure it out."

"You got me," my dad said. "Before the DNA test, she held all the cards. Now you do."

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