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

A Well-Lived Life - Book 6 - Kara I

Copyright © 2015-2023 Penguintopia Productions

Chapter 50: A Week in Chicago and a Girlfriend’s Birthday

Coming of Age Sex Story: Chapter 50: A Week in Chicago and a Girlfriend’s Birthday - 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  

March, 1982, Chicago, Illinois and Milford, Ohio

I arrived at O’Hare airport about ten minutes before Stephie’s flight was due to land. I parked in the short-term lot and quickly made my way into the terminal. I checked the arrival board and then walked briskly to the gate. The Jetway door opened just as I walked up and a minute later, I saw Stephie. She dropped her carry-on bag and ran to me, leaping into my arms and wrapping her arms and legs around me. She kissed me hard, then released me and stood in front of me.

“I take it you missed me?” I grinned.

“Yes! How was your break?”

“Pretty good. How was yours?”

“Also pretty good. You didn’t happen to break up with Kara, did you?” she asked with an impish smile.

“No,” I chuckled. “But you have me for two months.”

She sighed, “Well, Yankee, that will have to do. But I’m going to keep you VERY busy!”

“I won’t complain, Peaches. Let’s go get your bags and I’ll take you home.”

“I like the sound of that. I missed being in your bed.”

“An hour from now, you can be there!”

We walked to the baggage claim and waited about ten minutes for her bag. Just over an hour later, we walked into the apartment in Hyde Park. The apartment was dark when we walked in because Elyse had left on Saturday morning to go to Ohio for her break. I checked my desk for important mail and there were a few letters, a couple of bills, and my usual envelope from Theo. I left it all and followed Stephie to my room. I set the alarm, though we didn’t have to be to school until 10:00am for our calculus mid-term.

“What do you need, Peaches?”

“A good, long, slow, fuck. Then I want to sleep in your arms.”

“Your wish is my command!” I grinned.

We quickly removed our clothes and got into bed.

“Do you mind if I get some Peach juice all over my face before we fuck?” I asked.

“Hell no, Yankee!”

I got between her legs and began licking her until she had a pair of orgasms and her juices covered my face. I moved up on top of her, entered her dripping pussy and we proceeded to have the good, long, slow fuck that she’d asked for. After her fifth orgasm, I filled her with my hot cum and we fell asleep in a sweaty tangle of bodies.

When we awoke, we took turns showering and then ate breakfast. We spent an hour reviewing calculus, then headed to school for the exam. I had no trouble at all with it and was confident that I had at least a 90, which, when combined with my homework, meant I had a solid A for the class so far. Stephie was equally confident. Neither of us had a second exam that day, so we headed back to the apartment for lunch.

Once we finished lunch, we planned the rest of our week. I had one exam on Tuesday, two on Wednesday and one on Friday. Stephie had two on Wednesday, one on Thursday and one on Friday. She’d stay home while I took my exam on Tuesday and I’d work in the computer lab while she took her exam on Thursday. We curled up on the couch to study together, though we didn’t have any more exams in common.

We took a break around 3:00pm to make love and drink some tea, then studied until dinner. After dinner we made love, then studied, then went to bed and had a fantastic hard fuck that left us breathless and sweaty. We opted to shower and change the sheets so that we could sleep comfortably spooned together.

On Tuesday morning after eating breakfast, I kissed Stephie goodbye and headed to IIT. I wasn’t sure if Jackie would be there for coffee given that it was exam week, but she was waiting in the Stuart building with two cups of coffee as usual. We greeted each other with a quick hug and she kissed me on the cheek.

“Did you have a good break?” I asked.

“It was OK,” Jackie replied. “Not much going on, really. Most of my friends are on break this week.”

“Yeah, mine too. It’s kind of odd that IIT was off by a week from everyone else.”

“Oh, you didn’t know? There was some serious maintenance work that needed to be done on the Main Building. They planned Spring Break around the dates the contractors could come.”

“Ah! The things I don’t know because I live off campus.”

“How was your break?” Jackie asked.

“Good. Nice and relaxing. I saw a few friends, saw some people I hadn’t seen in quite some time, and spent some time with my dad and my sister.”

We finished our coffee and got up. I had an exam, but Jackie was heading back to her dorm.

“Would you have lunch with me after your exam?” she asked.

“Sure. I’ll meet you at The Bog at 11:00am,” I said.

The exam that morning was for my C programming course. It was done in the computer lab and consisted of five problems, three of which were debugging code provided by the professor and the other two were programming exercises. I finished quickly and was confident that I hadn’t missed any points at all. I double-checked that all my printouts were correct, then handed them in to the professor and headed for The Bog.

Jackie walked in just after I did, and we got our food and sat down. We talked a bit about our Summer plans and Jackie was intrigued by my plans for my trip to Sweden and asked more about it.

“Wait, you speak fluent Swedish? Wow! That’s amazing!”

“Yeah, it’s a fairly easy language to learn, or at least it was for me. The best part is that verb conjugation is totally simple. And I do get to practice by talking to my friends regularly and writing letters.”

“That’s pretty cool. I took six years of French and I suck at it. The language, not the kissing!” she smirked.

“Cute!” I said.

“I can demonstrate, if you’ll let me!” she said with a smile, then added, “No strings.”

“You’re nothing if not persistent,” I said with a grin.

“I just want you to take me to bed once. No strings attached. I know you’re not tied down at the moment, and I know you can’t be my boyfriend. Won’t you just do it with me once?”

“Jackie...” I sighed.

“What’s wrong with me? I have a decent body, people say I’m cute, and I get the idea that you’ve done it with lots of girls. Why not me? It’s not like I’m a virgin or anything.”

Truth be told, there was nothing wrong with her. She was cute. She had a very nice figure, and fit the body type I liked — not too thin, smallish breasts, and a cute little butt. She was exactly the kind of girl I would have been happy to go to bed with in the past. Her behavior confirmed for me that whatever it was that was in the air or water at home seemed to be here, too. Stephie was basically insatiable, Elyse had made it clear she’d be with me again and Jackie was asking as well.

I tried to figure out how this was different from Dona, Mary, Krista, Jessica, or any of the other girls I’d been with. Or how it was the same as Anna or Susan. With Susan, it was easy to distinguish — I wasn’t attracted to her at all. Sure, in seventh grade she’d been my girlfriend, but she broke up with me and I’d moved on. With Anna, I had a history, one that I knew would cause issues — both for her and for me — if we resumed our relationship beyond having lunch together. She wanted a relationship, and I knew that I could easily have one with her.

Mary was easy to figure out — she and I could fuck or make love, and neither of us had any expectation of a long-term relationship. Jessica had been a fun diversion, and there had been no thought of a relationship on either side. Oh, for sure, she wanted to get together again, but it was purely physical. Ultimately, her desire to have sex with me was really tied to being able to go to Tracey’s parties.

Krista was probably the closest comparison I could make. She and I were certainly a one-off kind of thing. She promised to not ask again and to keep our relationship business-like going forward. She’d basically given me a dozen reasons why I should do it and all of them were pretty much on-target. My question for myself was what did I want out of this relationship? I had a friend, and I certainly didn’t want to mess that up. I also wasn’t really sure of my own feelings for Jackie beyond friendship and I was concerned about her feelings for me, which she’d already expressed.

“Steve? Are you listening? I asked what was wrong with me.”

“Sorry, I was just thinking about an answer. There’s nothing wrong with you at all. You’re cute, you do have a nice body. In fact, it’s exactly what I like.”

“My tits are too small,” she interrupted.

“No, they aren’t! I prefer smaller ones. But there are three potential issues. First, I don’t want to mess up our friendship. Second, I’m concerned about your feelings towards me. Third, I’m concerned about my feelings for you. Ultimately, would we wreck our friendship or would one or both of us want to keep doing it and make a mess of things for me?”

Jackie was silent for a minute, “I know I told you that I’d like to date you. But, I’m absolutely sure I can go to bed with you and still be your friend, and not take it the wrong way. Sure, if you were to actually ask me out, I’d say yes, but I can do this without becoming a stalker or freaking out. I know your situation. I know it’s a one-time thing. So, what do you say? Will you take me to bed?”

“Where would we go?”

“We can go to my dorm right now. My roommate has an exam this afternoon. Does that mean you’ll do it? You’ll go to bed with me?”

“If you’re sure that you can keep things more or less the way they are, then yes. Let’s go to your room.”

She smiled and got up. We tossed our trash in the can and put our trays on the stack. She took my hand and led me across campus to her dorm. She signed me in and we took the elevator up to the sixth floor. She led me to her room and then shut and locked the door.

“Uh, I know it’s a little late to ask, but do you have any rubbers with you?” Jackie asked.

I’d actually stopped carrying them with me regularly in Chicago. I didn’t need them with Elyse or Stephie, and hadn’t presumed to need them with Tatyana. Even back home, I wasn’t carrying them, though I had brought them in my weekend bag each time.

“I used to carry them regularly, but I don’t any more. I wasn’t expecting this, so I had no reason to have any on me.”

“Damn. I don’t keep them around like Papiya does. Of course, I don’t have the same call to use them.”

“Well, then we really can’t do anything today.”

“Damn! Damn! Damn!” Jackie said.

I went over to her and pulled her to me and hugged her.

“There’ll be another time. How about Thursday morning? I don’t have an exam but I was planning on being on campus. I’ll bring rubbers with me.”

“Thursday would be great. And more than one?”

“I’ll bring three!” I grinned.

“No way! Wait, you’re serious?”

“Sure. One occasion doesn’t mean one screw. If you have a few hours, we’ll use all three rubbers.”

“Yes! Thursday morning. I’ll make sure my roommate is out. What time?”

“Come find me at Stuart Hall any time after 8:15am. I’ll have to be back by 11:00am or so, but a few hours is enough.”

We exchanged a quick kiss, and she took me downstairs. I signed out and then headed home. When I got to the apartment, I got the mail from the mailbox and went inside. Stephie was sitting on the couch, studying. I took off my shoes and windbreaker and put my book bag down. Stephie got up, and we hugged.

“Wanna fool around, Yankee? I’m mostly done studying.”

“What did you have in mind?” I smirked.

“Well, you like yer peach juice, so I thought maybe you’d like to have some. Then, you could fuck me real nice like and then we could take a bath together. Sound good?”

It sounded great to me, so I took her hand and led her down the hall to my room. I spent twenty minutes getting as much peach juice as I could, though I had more in my mouth than on my face. We fucked really hard for close to fifteen minutes, then relaxed in a bubble bath.

“Damn, Steve, where am I going to find somebody who can fuck me that good and who’s as nice as you, not to mention can cook, help me with my studying, and generally take good care of me?”

“Well, I’ll still be your friend, Peaches. So, except for the sex, I’ll still be available.”

“Naw, you’ll have to spend lots of time with Kara, so you won’t have a lot of time for me. And I won’t be able to hang out here, neither.”

“Actually, you know Kathy and Kurt hang out here, so there’s no reason you can’t. We’ll work things out, trust me. Kara is totally cool.”

Stephie sighed, “But it won’t be the same. I have a question for you, Yankee. Would you want to go to the race at Talladega at the end of July?”

“That would be cool. I’d have to check with Kara. And you know at that point I can’t sleep with you, right?”

“Yeah, I know. But it’ll be fun, anyway. You can meet Red and Rose, too.”

“I’ll talk to Kara. I think she’ll be OK with it, but I can’t be absolutely sure.”

She snuggled back against me. I slowly slid my hand down between her legs and began gently rubbing her clit.

“Oh yeah...” she moaned softly.

I gently built her up, then pressed my finger into her steaming pussy.

“Make me cum, Yankee!” she growled.

I slid my finger in and out and twirled it, and put my other hand over her small breast, squeezing it firmly.

“Oh God!” she moaned as her pussy clenched my finger.

I continued fingering her through the orgasm and worked on building her up again.

“Fuck!” she groaned as her pussy clamped hard onto my finger.

I continued fingering her until she was close to a third orgasm, then slowed down to keep her right on the edge.

“Damn it, Steve, that’s mean!” she hissed.

I continued fingering her very slowly for another minute, then pressed my finger hard and deep into her.

“Unnnngggghhhhhh!” she groaned, and collapsed back against me.

I helped her stand up, then picked her up and carried her to the bed. We were soaking wet, but I didn’t care. I placed her on the bed, got between her legs, and quickly pressed my rock-hard erection into her.

“Ohhh!” she moaned.

As I began thrusting slowly in and out of her sopping-wet pussy, Stephie wrapped her arms and legs around me. I built her close to an orgasm, then began thrusting hard. Stephie held me tight with her arms and legs and groaned as her body shook and her pussy spasmed around my thrusting dick. A few more hard thrusts and I spurted cum deep into her. I thrust a few more times, then pulled out, slid down and latched onto her clit with my lips and began sucking and licking it.

“Fuuuuuuccccckkkkk!” Stephie groaned.

A few minutes later, she arched her back and groaned loudly. I continued sucking and licking for a few more minutes and she came again, groaning loudly and then collapsing into the pillow. Her eyes were closed and her breathing was ragged. I crawled up next to her and held her in my arms. After about twenty minutes, she finally spoke.

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