A Well-Lived Life - Book 9 - Anala
Chapter 29: Turning Twenty-One, Part II

Copyright © 2015-2023 Penguintopia Productions

Coming of Age Sex Story: Chapter 29: Turning Twenty-One, Part II - This is the continuation of the story told in "Book 8 - Stephie". If you haven't read Books 1 through 8, then you'll have some difficulty following the story. I strongly encourage you to read those before you begin this ninth book. Like the other books in this series, there is a lot of dialogue and introspection. There is also a lot of sex. Book 9 has 82 chapters and about 448,000 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  

April 22, 1984, Chicago, Illinois

Penny melted into my arms and moaned softly as we kissed. She tasted like cherry, and our tongues tangled, sharing the flavor of the lip gloss. I knew she was in a hurry, but I wanted to take our time and build the pleasure to the explosion that I knew would come. I wanted to savor it, and I knew it would be better for her if she did as well. If Penny had her way, I'd already be inside her! She broke the kiss, panting.

"Slowly, Penny," I said gently. "It'll be better. Let me make it perfect for you."

"OK," she whispered. "What do I do?"

"Let me, please. You'll know what to do when we get there. I promise!"

I kissed her again and then slipped the straps of her teddy over her shoulders. Penny shivered in anticipation. I leaned down and kissed the tops of her shoulders. She smelled of lavender body spray, my favorite, heightening my arousal. As I kissed Penny's neck, I felt her heartbeat accelerate. Her breathing was not quite ragged, but soon would be. And all I'd done so far was kiss her!

I slid the teddy down, exposing her small, firm breasts, and planted soft kisses on each one in turn. I dropped to my knees and pulled the teddy down to her ankles, and she stepped out of it. I leaned forward, nuzzling her downy pubic hair, inhaling deeply. I planted a kiss on her mons, then kissed my way up her belly and chest as I stood up. Unbidden, she pulled my pyjama top over my head, then kissed my chest, planting soft kisses on my nipples as I'd done to her. She knelt down and pulled down my pyjama bottoms, and giggled as she planted a kiss on my glans.

She stood up, and I pulled her to me and into a tight embrace. I felt her rock-hard nipples trying to bore holes in my chest as she wiggled her body against my erection. We kissed again, our tongues exploring each other's mouths, and our hands running over each other's backs and butt. After a few minutes, I broke the kiss and scooped Penny into my arms and laid her on the bed, which Bethany had left turned down.

I started kissing Penny at her shoulders and worked my way down until I sucked her nipple into my mouth and swirled my tongue around it. She moaned softly when I released her, then sighed when I sucked the other nipple into my mouth. I moved back and forth between her breasts for a few minutes, then kissed my way down to her aromatic, dripping pussy. I teased her labia and clit with my tongue, doing my best to excite her, but not quite bring her over the edge. Penny shivered when I pressed my tongue between her labia and licked from bottom to top.

"Steve," she gasped. "Please, do it now!"

I moved up and lay on top of her, my glans pressing against her swollen labia, feeling the volcanic heat that was building inside her. I looked her deeply in the eyes and kissed her softly.

"What do you want to do, Penny?"

"I want you to fuck me!" she whispered.

"Are you sure?" I asked, applying just a small amount of pressure.

"Yes! If you don't do it with me now, I'm going to bite it off the next time you ask for a blowjob!" she giggled.

"You would be very sad, Penelope Margaret!" I grinned.

"Please fuck me, Steve!" she begged. "I can't stand it!"

I pressed forward and my glans slipped past her labia, and Penny gasped as I came up against her hymen.

"OK?" I asked gently.

She bit her lower lip and nodded. I had expected her to get nervous at some point, and we were at that point now. I leaned down and kissed her softly, and then broke the kiss and looked deeply into her eyes. I pushed forward against her barrier and felt it start to give. I pulled back a bit, then pressed forward with enough force to break through.

"Oh!" she gasped.

I paused for a moment, watching Penny's face. She had grimaced slightly, but then the grimace had turned to a smile. The heat and pressure from her tiny pussy were intense, and I was tempted to just push all the way in without waiting. But I held off until she was ready.

"Put it all the way in!" she gasped.

I pulled back a bit and pushed deeper. It took six thrusts before I was fully embedded in her hot, silky, extremely tight tunnel. I leaned down to kiss her softly.

"You're no longer a virgin, Penny!" I said. "Are you ready for me to move?"

"Oh God, yes! I feel so full and warm now, and I'm tingling! Please move. Please fuck me!"

I slowly pulled back until just my glans was inside her, then very carefully pushed forward, embedding myself fully in her for the second time. Penny moaned softly when our pubic hair tangled, and gently moved her hips, grinding against me. She didn't seem to be experiencing any discomfort, so I pulled back and then slid in again, a bit more forcefully. She was so tight that I had to be careful not to hurt her, and more importantly, not to cum too soon.

On the fourth thrust, Penny flexed her hips to meet me, and then we slowly developed a rhythm. She wrapped her legs around my thighs and we kissed fiercely as we moved together. After a few minutes of slow fucking, Penny broke the kiss and gasped for breath. She wrapped her arms tightly around me and squeezed my thighs with her legs. She groaned deeply and her pussy began clenching my shaft.

"Oh my God!" she groaned.

"You like that?" I whispered.

"I never want to stop! Fuck me, Steve! Fuck me and make it happen again!"

We continued our relatively slow motion thrusting until she groaned a second time, this time, her body was shaking along with her pussy clenching me. The third one was even bigger and Penny groaned loudly as her entire body shook hard. I was getting close and began moving just a bit faster. We could no longer kiss — we were breathing too hard — but Penny could moan and beg me to make her cum.

"Fuck me!" she moaned over and over as I thrust deeply and firmly in and out of her spasming pussy.

Just before I reached the point of no return, Penny tensed, held her breath, and a crushing orgasm overtook her. She groaned and humped wildly against me, trying to prolong the overwhelming pleasure. I pushed as deeply into her as I could and allowed her spasming pussy to push me over the edge. I groaned and cum exploded from my dick, the pleasure causing me to nearly pass out. Penny's tight pussy clenched and spasmed, milking each spurt of cum from me.

By the time my orgasm finished, I was barely conscious. I simply lowered my head next to Penny's and tried to control my breathing. She hugged me as if her life depended on it, gently rubbing her mons against me. She gasped for breath and then I felt warmth on my face. I lifted my head to see that she was crying.

"Penny, are you OK?" I whispered.

"Yes! I'm not crying because I'm sad! I feel so warm and tingly inside! Can we do it again? Soon?"

I kissed her softly on each cheek, licking the salty tears from her face.

"Yes, of course. Let's rest a few minutes, OK?"

"Don't you dare get off of me!" she warned.

"OK. I'll stay here. We might want to shower, though. I suspect there's some blood."

"It didn't really hurt. Are you sure?"

"We can look, but I'll have to move."

She sighed, "Yeah, please let me see."

I gently pulled out of her, then lifted up and knelt between her legs. There was indeed blood on the sheet, and streaks of red along my dick and on her thighs. If proof of her virginity was needed, I certainly had it. She propped herself on her elbows and looked down, seeing the same thing.

"What a mess!" she giggled. "Is it always that messy?"

"It is, but usually without the red and pink!" I said.

"Maybe we should wash. And put clean sheets on the bed!" she giggled.

"How about a bubble bath? Then we can come back to bed and make love again."

"Yes!" she exclaimed happily.

We got out of bed and I noticed that she moved a bit gingerly. That didn't surprise me, given how hard she'd humped at the very end. I wondered if she'd really be up for another round after our bath. We changed the fitted sheet, tossing the soiled one in the corner of the room, then went into the bathroom. I drew a warm bath and added apple blossom bubble bath and we got in. Penny sat between my legs, leaned back, and sighed when I wrapped my arms around her.

"This is the best birthday ever!" she sighed a moment later.

"I have to agree! You were wonderful, Penny. I told you that you would do fine!"

"You really mean that?" she asked.

"Yes. You were fantastic. You feel really good and made me feel really, really good."

"You'll do this with me whenever I want? We can fuck lots?"

"Well, you don't want your mom to find out, but yes, we can fuck a lot. Eventually, you'll need to find a boyfriend who you can date."

"I can't until I'm sixteen!" she groused. Then she giggled, "So you can fuck me at least until then! I won't complain!"

"Neither will I!" I said.

We soaked quietly in the tub for a time. I enjoyed the feel of Penny's firm body in my arms and was ready for another round when she was.

"Could you be my boyfriend when I turn eighteen?" she asked.

"What do you mean? Like go steady?"

"Yes. I mean, if you don't get married before then."

"How about we worry about that in three years? Isn't there something you'd rather do right now?"

"Yes! I want you to fuck me again!" she hissed.

I slid a hand between her legs and gently rubbed her clit.

"Are you sure?" I asked, kissing her neck.

"Ung," she groaned, then added breathlessly, "Yes! I'm sure! Fucking feels SO good!"

"We can do it right here," I said.

I was already hard, so I helped her turn around and maneuver so that she straddled me. I slid forward in the tub, helped Penny position herself, and waited while she slowly slid down my shaft.

"Oh wow! This is cool!" she gasped, wrapping her legs around me. "What do I do?"

"Just move however feels good," I said.

"What about you?"

"Penny, your tight little pussy feels so good, anything you do will be fantastic!"

She started slowly rocking and sliding, trying to find the motion that gave her the most pleasure. We kissed, and I strummed her nipples with my thumbs. Penny found a motion that she liked and started moaning softly. She broke the kiss.

"I like this!" she gasped, and then groaned.

I felt her pussy grasping my dick, squeezing it tightly. She continued moving, and less than two minutes later, shuddered as she had another orgasm. I moved my hands to squeeze her butt and twisted my head to suck on her nipple.

"Oh God!" she groaned, humping harder.

I sucked and licked her nipple and then ran a finger over her rear entrance.

"Oooh!" she squeaked. "That felt weird!"

Penny began sliding up and down my shaft, moaning softly as I sucked her nipple and tickled her hole. I let my pleasure build and when she had her next orgasm, I began thrusting and twisting my hips. When the first jet of cum spurted from my dick, I pressed the tip of my finger into Penny's rear. She groaned and her pussy spasmed hard. We enjoyed our shared orgasm and when hers finished, she collapsed against me.

"Why did you do that?" she gasped.

"Because I thought it would make you feel good," I said.

"It was strange. I'm not sure I liked it."

"Then I won't do it again," I promised.

"I like sitting on it like this!" she whispered.

"We can do that in bed, too," I said.

We got out of the tub and got into the shower to rinse off the suds. I pulled her to me, with her back against me. I pressed my hand between her legs and gently massaged her clit. Penny sighed and leaned back against me while I slowly worked her to an orgasm. When she shuddered, I pressed my finger into her opening and fingered her through the orgasm. She breathed out hard and nearly collapsed. I held her around her waist with my other arm, supporting her.

"You OK?" I asked.

"Yeah. I'm a little uncomfortable, but I want to do it again!"

"Penny, I could use my mouth and tongue. That way I won't hurt you," I said.

"Maybe that's a better idea," Penny replied. "I could do that for you, too."

We got out of the shower and we dried off. I led her back to the bed, and we got into a 69 position. Penny gingerly lowered her pussy to my face and took my glans into her mouth. It didn't take long before I was rock hard and she slowly took most of my dick into her mouth, sucking gently and swirling her tongue. The pleasure was exquisite, but I held out until I'd licked her to two orgasms, then filled her mouth with my cum, which she quickly swallowed.

Penny moved off of me and turned around. I pulled her to me so we could cuddle. We kissed deeply, then lay together for about twenty minutes before I asked her if she wanted some champagne. She said that she'd never had any before, so I got up and opened the bottle. I poured us each a glass and handed one to her. She sipped it and wrinkled her nose.

"That tastes funny and tickles my nose!" she giggled.

"Don't drink it if you don't want to," I said. "Not everyone likes it."

She took another test sip, but didn't hand me the glass. It took ten minutes, but she finished her glass. I took it from her and got back into bed with her. We still had about two hours before the party started, so I pulled the duvet over us and we cuddled.

"Are you doing OK, Penny?" I asked.

"Yes! Will it always be uncomfortable like this after we do it a few times?"

"No. It's because you were a virgin. By Wednesday, you'll be fine and it won't hurt anymore."

"Good!" she grinned. "I really want to do it again right now, but I don't think I should."

"Then let's just cuddle," I offered.

We lay together until about 11:00am, when we got up and showered again. We dried off, then dressed. Penny sprayed her body spray on her and we waited until her hair dried. Once it did, which was about 11:40am, we left the room and went downstairs. Penny was all smiles when we walked into the kitchen and she asked if she could help.

 
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