A Well-Lived Life - Book 6 - Kara I - Cover

A Well-Lived Life - Book 6 - Kara I

Copyright © 2015-2023 Penguintopia Productions

Chapter 6: First Day of School

Coming of Age Sex Story: Chapter 6: First Day of School - This is the continuation of the story told in "Book 5 - Stephanie". If you haven't read Books 1 through 5, then you'll have some difficulty following the story. I strongly encourage you to read those before you begin this sixth book. Like the other books in this series, there is a lot of dialogue and introspection. There is also a lot of sex. Book 6 has 60 chapters and about 330,000 words. It's a lengthy read. I hope you'll stick with it!

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   mt/ft   Ma/ft   Mult   Teenagers   Romantic   School   First   Slow  

August 1981, Chicago, Illinois

The rest of the week went as planned. We went to Wrigley field to watch the Cubs lose to the Dodgers 5-0. We rode our bikes along the lakeshore and visited the museums. I went to my karate classes. And we fooled around a lot. Elyse was a very creative lover, and completely uninhibited. We made love in our beds, on the couch, on the floor of the living room, in the shower, and sitting in a kitchen chair. We even tried using the kitchen counter, but the angles were wrong. I felt that Melanie’s sex positions book had left out a few we’d tried out!

Late on Saturday afternoon, we were sitting on the couch together, listening to music and talking. School would start on Monday and we knew our schedules would be hectic. I also knew I’d be getting a call from Kathy soon, and I figured I’d hear from Bethany and Pam, most likely on Sunday.

“Is there anything you want to do tonight or tomorrow?” I asked.

“Not in particular,” Elyse replied. “I figured we’d just relax, given that we’ve had a busy week.”

“Very true. How about we go out to dinner and then we spend the night fooling around!”

“The night?” she asked with a smirk and an arched eyebrow.

“The night,” I replied with a similar smirk. “Until you or I pass out. I figure we can combine everything we’ve done all week!”

“You’re on, big boy! Whoever passes out first has to do all the cleaning for a month!”

Given how sensitive she was and how easily I could bring her to orgasm, I suspected I’d win easily, but I wasn’t sure — the Elyse who had moved in with me was most definitely not the Elyse I’d known for the previous several years!

“Deal!” I agreed.

We got up and changed out of our shorts and t-shirts and headed to a diner on 50th Street that we had discovered on an evening walk. We enjoyed our meal and walked the short distance to an ice cream shop where we got chocolate cones that we ate on our way back to the apartment. After eating the cone, I decided we had to find a better place because what we’d just eaten didn’t remotely approach Graeter’s.

We walked inside and kicked off our shoes, and sat on the couch.

“Can I change my mind?” Elyse smirked.

“What? Afraid you’re going to lose?”

“No, there’s one thing we haven’t done. I want you to blindfold me and tie me up and just do whatever you want. No limits. No restrictions.”

I cocked my head and smiled and stood up, taking her hand. “As you wish! But we need a safe word.”

“Safe word?”

“In case you need me to let you go. It’s important.”

“OK. What’s the safe word?”

“Something that will never come up in a normal situation. How about ‘Donald Duck’?”

Elyse laughed and agreed.

I led her to her bedroom and slowly removed her clothes. I pulled the soft rope from her bag and tied her hands together, wrapping the rope around them several times, then led her to the bed and tied the rope to the center of the headboard by passing it through a round, decorative hole. I figured it was strong enough and tied the rope tightly. That would let me turn her over when I wanted to without untying her hands.

I turned her on her stomach and then took some additional soft ropes and tied her legs tightly to the frame of the bed so that her legs were spread wide. I took the massager from her bag and rubbed a bit of lube onto it. I turned it on, then slowly worked it into her pussy, making her squirm and moan softly. I spread lube on my dick and then between her butt cheeks. From the previous night, I knew that she would relax and accept me, so I pressed my dick against her hole. She breathed out slowly, and I pushed hard, embedding my dick about two inches into her butt.

“Ungh!” Elyse groaned.

I pulled back a bit and shoved forward so that I was almost all the way in. She grunted and again I pulled back a bit and gave a final hard shove, burying myself in her butt.

“Ungh! Yes!” she hissed.

I began thrusting gently in and out of Elyse’s rear, slowly building speed until I was able to move more or less freely.

“Yes!” she hissed. “Fuck my ass!”

I was still amazed at how wild and crazy Elyse was, even after a week. The first time we’d done this, I was gentle, and she had complained about me being too gentle. I wasn’t gentle; I thrust hard on each stroke, burying myself deeply in her. At each thrust, I could feel the massager vibrating in her pussy, each time her hips bucking as my thrusting in her butt made the massager move around inside her, without slipping out, adding to her pleasure. I continued until her breathing told me she was close. I pushed deep into her and slipped my hand underneath her and flicked her very sensitive clit, triggering a huge orgasm and making her scream into the pillow! I started pumping in and out again, working towards my own orgasm. A minute or so later, the heat and pressure were such that I knew it would happen soon. I slipped my hand under her again and gently rubbed her clit while I thrust two more times. I exploded deep into her and she groaned loudly as cum filled her butt.

I pulled out and reached into her bag and put some lube on her dildo and pressed it into her butt, easily filling the void my dick had left. I went to the bathroom and quickly washed myself, then went back to the room. I released the ropes from the bed frame and turned her on her side. I lay down next to her with my face by her pussy and pressed my dick against her lips. She opened her mouth and sucked me in. I slowly slid the massager out of her pussy and replaced it with my tongue. I draped a hand over her and began to gently slide the dildo back and forth in her butt while I licked her.

I continued licking and sucking her pussy until she had sucked me hard again. Keeping her on her side, I got up and raised her left leg and straddled her right leg. I pressed my dick against her pussy and pushed hard. I slid all the way in and then began slowly thrusting in and out of her. Elyse had two orgasms and when I was close, I pulled out and lay down next to her again, pushing my dick into her mouth. I grabbed the massager and began fucking her with it. Just a few seconds later, I came hard, firing spurt after spurt of cum into her mouth. She swallowed each spurt and when no more came out, I gently removed my dick from her mouth, slowly, so she could lick a last drop of cum from the glans.

I knew it would take some time before I could get hard again, so I used the massager on her. She had several orgasms, and her breathing was labored. When I was ready, I turned her on her stomach and moved her legs so that she was on her knees with her butt in the air. I left the dildo in place and carefully pushed my dick into her pussy. I changed her position slightly so that I could thrust into her. I used my finger to gently rub her clit and brought her to another huge orgasm before I came for the third time.

I needed some rest, so I moved her legs so she was flat on her stomach again and pressed the massager back into her pussy and turned it on. I sat on the chair by the desk and drank some water while I let her toys pleasure her. She moaned softly, and I saw her body shake as she came. I went over to the bed and kissed her on the lips.

“Anything else I can do for you?”

“I want to be on top.”

I loosened the rope, so that she had a bit of slack, then removed the massager from her pussy. I got into bed next to her and helped her straddle me. I held my dick upright and against her pussy. She slowly lowered herself onto me and began grinding against me. We kissed and then I pulled her to me so that I could suck on her nipple while she rode me, the dildo still in her butt. I could tell she was working towards a shattering orgasm. She was gasping for breath and grinding harder against me.

Suddenly she tensed, then growled, her body shaking hard, her pussy spasming tightly around my dick as she screamed. She gasped for breath as the orgasm washed over her and she collapsed on me. I reached up and took the blindfold off, then reached behind my head and managed to untie the rope. I reached down and, with a bit of effort, pulled the dildo out of her, gently lifting her off me. I turned her on her back and got between her legs. I slowly and deliberately entered her.

Elyse opened her eyes and smiled as I began making love to her, not just having sex with her. She wrapped her legs around my thighs and simply held on as I slid in and out of her sopping wet pussy. We exchanged only brief kisses because she was still gasping for breath. About ten minutes later, when I felt the twinge, I began pounding hard into Elyse and with a final thrust, fired several jets of cum into her pussy while I ground against her clit. She groaned softly and her pussy clenched me gently. I kissed her softly and rolled off.

“You win,” she whispered.

We lay together for about twenty minutes and I suggested a shower. She just nodded, and I helped her into the bathroom. I adjusted the water, then washed her from head to toe. I did the same for myself, then dried us both off. Her bed was a mess, so I led us to my room, where we curled up together under the comforter and quickly fell asleep. When I woke up in the morning, I got up, leaving Elyse asleep. I got the sheets from her bed and put them in the washing machine, then went out to run. When I came back, I moved them to the dryer and went back upstairs.

Elyse was still sleeping, so I cleaned up all her toys and put everything away. I took my shower, then called Karin. By the time I hung up, Elyse was stirring. She walked naked out of my room and flashed me a smile. I walked over to her and took her in my arms and hugged her. We exchanged a soft kiss.

“Want some breakfast?” I asked.

“In a bit. Come soak in the tub with me. It’s small, but we can fit.”

“I’ll bring some tea. It’s ready.”

She nodded and went into the bathroom. When I came in with two mugs of tea, she had put bubble bath in the water and was sitting in the center of the tub. I put the mugs down on the side of the tub, got in behind her, and pulled her back to me. We took our mugs and sipped tea as the hot water filled the tub and the bubble spread around us. Elyse sighed.

“It’s been a long time since I did something like that. Two-and-a-half years, to be exact. Thank you!”

She leaned her head back, turned to me, and we exchanged a soft kiss.

“You are wild beyond anything I could imagine!” I said. “I had no idea.”

“Blame Sean for that! He took all my cherries the same day. I was sore, but satisfied. What you did was like the very last time I was with him.”

“What happened?”

“He found an even younger girl. I think he’s a pervert, personally. I turned fifteen, and he went with a thirteen-year-old.”

“Wow. I guess that was pretty devastating for you!”

“It was. That was a few months before I met you. You were so nice and I needed someone to love me. Jennie had told me what a great guy you were. I had sex with you because I wanted to sleep in your arms.”

“I’d have let you do that without having sex!”

“I know that now. You turned out to be very different from Sean. You’ve got more stamina, too!” she giggled.

It seemed like she was trying to lighten the mood after it had become pretty dark.

“Did he force you to do any of that stuff?” I asked carefully.

She was quiet, obviously considering her answer.

“I don’t think force is the right word. I had just turned fourteen and one of my friends had an older brother I thought was cute. That was Sean. He had graduated from Live Oaks and was working in an auto shop in Glen Este. I flirted with him a bit and then we kissed. I liked it and I ended up at his apartment. We were making out, and I was super excited. I let him touch my boobs, and then he rubbed his finger between my legs. You know how sensitive I am when I get excited? Well, I felt like I was exploding. At that point, I let him do whatever he wanted. He fucked me and I came hard again, so when he asked for a blowjob I did it and then he used his mouth on me and I got so excited I didn’t object when he put his dick in my butt. So, he didn’t force me, he just had me so excited that I would do anything.”

“That sounds like a couple of girls I was with. One regretted it and the other one asked for more. So what happened?”

“I saw him every chance I got, and he did all that stuff over and over again. Then he started buying me toys and eventually the ropes and blindfold. I didn’t care because the orgasms were crushing. Not long after I turned fifteen, I went to his apartment to see him and he had a girl I knew who had just finished 7th grade with him. I left and never went back and he never called me or talked to me again.”

“And that was a couple of months before the wedding?”

“Yes. I was really hurt and upset, but what could I do? Then I had the chance to be with you and I wondered what it would be like to be loved instead of just having sex. You seemed like a nice guy and, as I said, I wanted someone to love me and hold me in their arms. You did. But then I found out about Jennifer and how serious you were with her. I was sad, but I didn’t blame you because according to your relationship with Jennifer, what you did was OK and I made the mistake of not asking enough questions.

“Then you went away for a year and when you came back, all your troubles with Jennifer started. As much as I wanted to be with you, I knew I had to wait. I dated other guys, but none of them seemed right. Mostly, they just wanted to get into my pants and I wanted someone who could actually love me. Remember my comments about casual sex? Well, none of them really wanted a relationship.”

“Are we in a relationship?” I asked, a bit concerned by her comment.

“Oh! Sorry, I think you misunderstood what I meant. Yes, we are. But not like going steady or anything. You care about me. You showed that by washing my sheets this morning when you got up. Hell, I’ve never seen anyone who cares more about his friends than you do, even when you’re in one of your snits. You recover and then you apologize and fix it by doing whatever it is you have to do. I guess you haven’t had one of those since Jennifer left. All I want from you is for you to care about me. To be my friend. To love me. To keep the future open. If you can do that, I’ll fuck you sideways. I’ll do anything you ask. Anything. I have just one condition.”

“That I not say a word to anyone about this,” I said gently.

“Exactly. Keep your mouth shut and you can have it all. For as long as you want. Well, for as long as you treat me right and care for me. If you can think of anything we haven’t done, just tell me. I’m game for anything.”

“You were really surprised that I had done all those things?”

“Yes. As I said, you were with all those young girls. I didn’t know who would have done those things with you.”

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