A Well-Lived Life - Book 8 - Stephie
Chapter 27: New Experiences

Copyright © 2015-2023 Penguintopia Productions

Coming of Age Sex Story: Chapter 27: New Experiences - This is the continuation of the story told in "Book 7 - Kara II". If you haven't read Books 1 through 7, then you'll have some difficulty following the story. I strongly encourage you to read those before you begin this eighth book. Like the other books in this series, there is a lot of dialogue and introspection. There is also a lot of sex. Book 8 has 82 chapters and about 455,000 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   Ma/ft   Mult   School   Incest   Brother   Sister   First   Slow  

May, 1983, Chicago, Illinois

We finished eating and Dave and Julia said that they were heading out to the movies. We said 'goodbye' and I took Jackie's hand and started down the hall. I looked back over my shoulder to see Elyse and Stephie smirking.

"Just call if you need help!" Stephie said.

"Or a paramedic!" Elyse added.

"What did I get myself into?" Jackie asked, clearly rhetorically.

I wondered if I should say anything or just wait for her to object or cry 'uncle'. She'd had a couple of drinks, but she'd shown she wasn't drunk during our dinner conversation, so I took her into my room and helped her out of her clothes. I removed mine, grabbed the lube from my nightstand, and then took her hand and led her to the bathroom. I turned on the shower, adjusted the water as warm as I thought she could handle and helped her into the tub.

"You just relax and let me do the work!" I grinned.

I made a nice lather with Stephie's rose-scented soap, then proceeded to wash every inch of Jackie's body, paying particular attention to her firm breasts and rock-hard nipples. My touches caused her to moan softly, and when my soapy fingers slid along her puffy labia, she shuddered slightly. When I finished lathering her body, I helped her rinse off, then positioned her in front of me so that the spray cascaded over us. I gently massaged her shoulders, trying to work the stress out of her muscles.

Ever so slowly she relaxed and when most of the tension was gone, I moved my hands to cup her breasts, and then began tweaking her nipples. I leaned forward and kissed her shoulders and neck several times, then slowly slid my left hand down to her mons, then pressed my finger between her legs. I slowly stroked Jackie's labia and nipped at her shoulder, causing her to moan again. I pulled her back against me so that my erection was lodged between her butt cheeks as I gently massaged her clit and sucked her earlobe into my mouth. A moment later, she shuddered and had her first orgasm.

"Keep going, Steve," she whispered urgently.

I was happy to oblige and pressed my finger between her labia and into her tunnel, gently working her towards another orgasm. A few minutes later, she groaned and her body shook slightly, her pussy grasping my finger. I released her and she moaned softly.

"Don't stop!" she begged.

"Just relax," I said quietly.

Jackie's eyes were closed, so she didn't see when I picked up the tube of lube and spread it liberally on my dick, then moved close behind her again. I slipped my finger into her pussy and she sighed, but then I positioned my dick against her rear entrance and she gasped.

"What are you doing?"

"Over the top!" I said and thrust forward hard enough to pop my glans into her.

"Oh, fuck!" she groaned. "What the fuck are you doing?!"

"A great, over-the-top fuck. That's what you asked for!" I said, thrusting again and moving another inch into her and pressing my finger deeper into her pussy.

"I didn't ask for this!" she gasped.

"Sure you did!" I said, pushing another two inches into her. "But I'll stop now, if you want."

"I don't know what I want!" she groaned, so I pushed in even further.

"I can stop now and take it out," I said, pushing the rest of the way into her, "or keep going."

"This is what Elyse and Stephie were talking about?" she gasped, then groaned as I pressed hard on her clit.

"I'm just getting started!" I chuckled.

"Oh God!" Jackie gasped, "I feel so full!"

I began fingering her and slowly withdrew most of my dick from her butt, leaving just the glans inside her. When she didn't protest, I pushed forward again until my pubic hair was touching her butt. Jackie groaned again, and I stayed fully embedded in her and continued to tweak her nipple and finger her. I lowered my mouth to her neck and began kissing and nibbling, and she moaned softly.

"Fine, God damn it!" she growled. "Do it!"

I began slowly stroking in and out of her butt while I pleasured her with my hands and lips. Jackie was groaning with each thrust and moaning each time I pulled back. My attention soon had the effect I desired, and Jackie's pussy spasmed around my finger. She squeezed the muscles in her butt tight and groaned loudly as her orgasm washed over her. I kept up the slow, steady strokes and a few minutes later she came again.

At that point, I let my pleasure build and a minute later I sprayed cum deep in Jackie's butt. When the last spurt fired, I slowly withdrew and held Jackie with one arm while I grabbed the soap and washed my dick. I shut off the water and, using a towel, I dried us the best I could, then picked Jackie up in my arms and carried her from the bathroom to the bedroom. I shut the door with my foot and put Jackie on the bed.

I moved between Jackie's legs and began licking her pussy, and pressed a finger in as deeply as I could. Jackie groaned and gently bucked her hips, pressing her pussy against my mouth. Over the next twenty minutes, Jackie had three more orgasms. I felt I was recovered enough and using my free hand to stroke myself until I was hard. I grabbed a condom, rolled it on and then quickly moved up and positioned my dick against her labia and pushed hard, embedding myself deep in her in a single thrust.

Jackie was clearly dazed, but she wrapped her legs around me and I began fucking her as hard as I could. I pounded in and out of her, occasionally grinding against her. I fucked her hard through two orgasms before I slammed deep into her and filled the rubber with cum. I wasn't about to let up, so I pulled out, removed the rubber, and moved down so that I could lick and suck her nipples, causing her to moan again.

"What the hell are you doing?!" she moaned.

"Over-the-top," I said, releasing her nipple. "I can cum at least three more times."

"Oh my God!" she gasped as I switched breasts.

I spent another five minutes on her breast before sliding down and putting my mouth on her clit and lashing it with my tongue. She bucked hard and came when my tongue touched her clit. I didn't let up, sucking and licking while she moaned and bucked.

"Steve!" she gasped. "Please, no more!"

I stopped and lifted my head, "Really? That's it? You can't take it? Wow!"

"You bastard!" she growled. "Fine! Fuck me again!"

Her request and my hand helped me get hard enough to roll a condom on and then push deep into her. She wrapped her legs tight around me.

"Fuck me, you bastard!" she demanded.

I began moving hard in and out of her.

"Fuck me, God damn it!" she groaned.

I began pounding her as hard as I could, and she matched my strokes by thrusting her hips hard against me. She was gasping and moaning, and demanding I fuck her hard. She had a couple of orgasms before I came for the third time. I was getting tired, but I wasn't going to stop yet. After I pulled out, I removed the second rubber, then moved down and started licking her nipples again.

"Again?" she gasped.

"You did ask for over-the-top, Jackie. Once more, then? But this time, slow and soft."

"OK," she whispered.

I used my tongue on her pussy until I was ready, then rolled a final rubber onto my dick and slid gently into Jackie's battered pussy. We made love slowly and gently for the next twenty minutes and after a final mutual orgasm, I withdrew and grabbed the two used rubbers and went to the bathroom to dispose of them. I quickly showered, then walked out to find Stephie and Elyse.

"You could at least get dressed, Yankee," Stephie giggled.

"I don't think she'll be moving before morning!" I grinned.

"Go sleep with her, Steve. After what I'm sure you gave her, she deserves it!"

"She got it all, Peaches!" I grinned.

"Toys?" Elyse asked.

"Nah," I chuckled. "It didn't get quite that far."

"Go sleep with her, Steve." Stephie smirked.

I went back to my room and got into bed next to Jackie and pulled the duvet over us, then put my arms around Jackie and cuddled her. She quickly fell asleep, and I wasn't far behind. I awoke first, but stayed in bed with Jackie cuddled against me. When she eventually woke up, she looked up at me and smiled.

"God damn, Steve," she whispered. "Elyse was right. I had no idea what I asked for. And you could have kept going?"

"Yeah, probably one more," I said.

"You missed one," she giggled.

"Well, I used rubbers, so technically I didn't cum in your pussy," I said.

"And that's a good thing! Getting pregnant would be bad. Very, very bad. Want a blowjob?"

"Sure!" I grinned.

She slowly sucked me into her mouth, quickly getting me hard. As she had in her dorm room, she took me fully into her mouth and then bobbed up and down, running her tongue around my shaft and sucking hard when she had just my glans in her mouth. It took about five minutes before I groaned and fired several spurts of cum into Jackie's mouth. I felt her swallow each one in turn, and when she had taken the last spurt, she licked me clean. She moved up to kiss me and I pulled her close and our tongues tangled.

"Thanks," she said, breaking the kiss.

"Let's go shower!"

I led her, naked, to the shower, and we washed up, then went back to my room. She put her clothes back on and I put on fresh clothes, and then stripped the sheets from the bed. I lit an apple cinnamon candle in the room to clear out the odor of sex. We walked out to the kitchen to find Elyse and Stephie drinking coffee. I poured myself a cup and started making breakfast. After breakfast, we walked out to the car so that I could drive Jackie back to her dorm so she could change and pack.

"That was insane," Jackie said once we were in the car.

"I'm glad you liked it!" I grinned.

"It was so intense. It wasn't just the orgasms; it was that you just never let up. My boobs and pussy were so sensitive and the constant pleasure was, I don't know, almost painful. But not quite. I thought I was going to pass out when you were making love to me at the end there."

"Did it take the edge off?" I chuckled.

She laughed, "What do you think? Of course it did! Then again, I wasn't exactly expecting you to shove your dick in my ass, you jerk!"

"I know that!" I smirked. "You asked for over-the-top, and you got it. I'm curious about what you thought?"

"It was weird, and I wanted you to stop, but I decided to let you go for it. Don't ever do that again without asking first!"

"I'm sorry; I should have talked to you about it."

"No, actually, you shouldn't have. I'd have refused and missed out on an experience that I guess I needed. How long am I going to feel strange?"

"A couple of days at most. I am sorry about that."

"Quit apologizing. You didn't hurt me, you surprised me. And it doesn't feel nearly as uncomfortable as I felt for a day or two after Bill took my virginity."

"OK. Are you planning on coming back to the apartment later?" I asked, changing the subject.

"I am. I arranged with Elyse to sleep in her room. Can we meet at the house around 1:00pm to drop my stuff? I don't want to leave it in the car while it's parked on the street."

"Sounds like a plan. Do you need me to walk you up to your room?"

"Only if you brought a condom with you!" she exclaimed.

I hadn't because I didn't think I'd get an offer like that this morning.

I chuckled, "No, I didn't. And you didn't get enough?"

"It was just too intense. If you had let me rest in between, we could have fucked all night!"

"True," I said with a silly smile, "but that wouldn't have been the same!"

She smiled, and we exchanged a soft kiss, then she got out of the car and headed for her dorm. I pulled out of the lot and drove back to the apartment.

"How is she?" Stephie asked when I walked in, and offered me a cup of tea.

I took the cup from her and answered, "Dazed, but happy."

Both girls laughed.

"What's the plan for the day?" Stephie asked.

"Well, I guess the question is whether or not we're going to the church service tonight. We could go to Dave's church with him and Julia, or the Russian Church, which he thinks I'd like better, or we can just stay home. Only Katy, Jackie, and Cindi were planning on coming over today. The rest are packing or, like Kurt and Kathy, spending time together alone because they'll be parting for the Summer."

"Isn't Chris leaving for Texas today?" Elyse asked.

"Late this morning," I said. "That's why Cindi will be here later — her guy is going away."

"How serious were they?" Stephie asked.

"It was pretty casual. I got the impression that they were fooling around, but both realized that after today, they'd be apart for some time. The gist I got from Cindi was they were breaking up because she'll be here for two years and she has no plans to move to Texas."

"And Jackie and Jamie?" Elyse asked.

"They've never progressed past coffee or dinner, and hanging out here. He just doesn't have the time. And I guess his third year of law school is going to be even worse. She likes him, but doesn't like the small amount of time he has for her. What bugs her is that even after he graduates, he'll have long, crazy hours as a junior associate. I did point out to her that fourth and fifth year architecture students don't have much of a life — look at Chris. He spent a bit of time here, but that was all his free time, except for whenever he and Cindi managed to sneak an hour or so to fool around."

"Jesus," Stephie said, shaking her head. "What a life. Lawyers, architects, and doctors may make good money, but the hours they have to put in at school and then working are nuts."

"You didn't see me when I was running my business at first, Peaches. I spent a ton of time on the computer. It's one of the reasons I sold it — the hours would have been crazy. Even as it is, you see me working on my programs for four to six hours a week and that's just supporting a few consulting clients here and doing the odd work for the guys who bought my company."

"I guess working in a research lab might be like that — you really can't just go home when the whistle blows if you're in the middle of an experiment."

"Bingo," I said.

"Shit," she sighed. "What did we all sign-up for?"

"Not digging ditches or working at McDonald's," I said. "I'm not disparaging people who do that, but we wouldn't be happy in those jobs."

"True. Hell, even Red works crazy hours in the speed shop, and I guess it'll be even worse if he goes to work for a NASCAR team. You saw Bill working on a car the day after the race!"

"Yeah, but I got the idea that was his personal project, not a team project."

"True. Did you want to see him again when we go to the race? I can even get some pit passes for us. I just need to call Emily's dad and ask."

"That would be cool!" I said. "So, what about tonight?"

"Let's go to Dave's church, Yankee. I'd rather party with someone I know than only complete strangers."

"Elyse?"

"Hell no! I'm sleeping!"

Cindi, Jackie, and Katy arrived during the afternoon and, except for Stephie and me taking a nap, we spent the afternoon and evening just hanging out with our friends. About 9:30pm, Stephie and I changed into dressy clothes. Dave had told me that people dressed up for church even on regular Sundays, which was a real contrast to St. Andrew's, where quite a few people would come to church in casual clothes. To me, dressing up for church made sense. I put on my charcoal gray suit and Stephie put on a blue and white knee-length gingham dress, white stockings, and a white shawl.

We headed to my car to drive to Annunciation Greek Orthodox Cathedral, which was on the North Side of the City, on LaSalle, just north of Oak. When we arrived, the small parking lot was completely filled with cars and a young Greek man directed us to a parking lot on Maple that was two blocks away. We parked and walked to the church, joining the throng of people streaming in.

"Wow!" Stephie breathed as we walked into the dimly lit church.

There were icons everywhere, including on the ceiling. At the front of the church was a wooden screen, which I remembered from the books I had read was called an iconostasis, that separated the altar from the rest of the church. The smell of incense was overwhelming and candles and oil lamps were burning everywhere. We had no idea where we might see Dave and Julia, so we took seats in pews far in the back of the church. I scanned the people that had already congregated and didn't see either of them.

A few minutes later, Dave and Julia walked in and came over to us. Dave told us to follow him, and we moved to a pew that was about halfway forward. He quietly explained what was going to happen as the church quickly filled with worshipers. About 11:00pm, the church was darkened completely, and the choir began to chant, alternating between Greek and English. Prayers were sung by the priest and bishop, and eventually the bishop came to the door of the Iconostasis with a single candle and bade the faithful to come light their candles.

 
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