Climbing the Ladder - The First Rung - Cover

Climbing the Ladder - The First Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 36: Romance Novels

Coming of Age Sex Story: Chapter 36: Romance Novels - 'Climbing the Ladder' is the story of Jonathan Kane, a young man from rural Ohio, who begins a new life in Chicago in the mailroom of Spurgeon Capital. This is a story in the 'A Well-Lived Life' universe, and provides history and backstory for Spurgeon Capital, the Spurgeon family, the Glass family, the Lundgren family, Anala Subramani, Tom Quinn, and others from the 'A Well-Lived Life' series. The story stands on its own, and does not require reading any other stories in the universe.

Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa   Ma/ft   Rags To Riches   Workplace  

January 2, 1982, Chicago, Illinois

“What about your butler and maid?” I asked.

Jeri smiled, “They are ‘black holes’ — no information ever escapes. Complete and total discretion. The same is true for James. My parents won’t know we went out or that you were here, and won’t know if you spend the night. Violating discretion in that way is an automatic firing offense.”

“OK, and should your parents somehow find out...”

“My mom might object to me giving up a valuable commodity to a ‘commoner’, if you’ll excuse the term, but otherwise? She wouldn’t say a thing. But she’ll never know.”

“Back home it was the dads guys worried about.”

“Shotguns, right?”

“Mostly, but hunting knives are also an effective deterrent.”

“My mom is in charge of the family. My dad does what she says and gets to spend money however he likes and have his mistress without any interference from my mom.”

“Your mom knows about his mistress?”

“She’s happy he has a mistress because that keeps him from pestering her for sex. As best I can tell, she doesn’t like it but knows it can get her the things she wants. I, on the other hand, expect to enjoy it. I expect you to enjoy it as well.”

“I thought that was a given, at least according to what you said before.”

“Different levels of enjoyment, Remember what I said about sleeping naked in your arms.”

“I remember. That’s what you really want?”

“No,” Jeri replied flatly. “I’ve spent the last three hours trying to talk you into going to bed with me simply to mess with you when you agreed to do it.”

“When you put it that way, it was a dumb question, wasn’t it?”

“Yes.”

It really was just a question of me getting past the fact that Jeri was sixteen, which was only a problem because of Illinois. I’d had no qualms about fooling around with Bev just after she turned sixteen. Everything Jeri had said made sense, and if I was honest with myself, having someone like her, outside the system, as a partner, made a ton of sense, just as it made sense for her to have a partner outside her usual circles.

I was confident she would keep what happened between us private, and there would be no fallout from her parents, or anyone else for that matter. I realized that I could have the business relationship without the sex, but why not have both? Nobody would be hurt by it, and I was confident it would be fun. I didn’t need it, given the girls who were available to me, but I wanted it.

The only question in my mind was whether I should wait until after I spoke to Anala on Tuesday, but I quickly dismissed that as silly, because she’d ask me questions and if I gave honest responses, I’d reach the exact same conclusion. The bottom line was that Jeri was offering something that made complete sense to me — a backup plan, which was something I did not have. And in the end, that’s what made the decision very easy.

I just had one problem — no rubbers, because I hadn’t planned on anything remotely like this.

“Birth control?” I asked.

Jeri smiled, “Mom put me on the Pill at thirteen so that there were no accidents.”

“Thirteen?”

“Right after I got my period. And all it took was a word with her OB/GYN who is in our social circles. I assume that question means you’ve decided to stay?”

“No. I always ask a girl about birth control when I plan to not go to bed with her!”

Jeri laughed, “I guess it was my turn to ask a dumb question!”

“Yes.”

“Well,” she asked coquettishly, “are you ready to plunge your throbbing manhood into my volcanic depths?”

“Where did THAT come from?” I asked.

Jeri laughed, “A romance novel! I started reading them about three years ago.”

“What’s a ‘romance novel’?”

“You seriously don’t know?”

“I seriously don’t know.”

“They’re cheap paperback books that follow a basic pattern — love, relationship, and sex, though mostly implied. All of them have an emotionally satisfying ending. The best-selling ones are called ‘Harlequin Romances’. They use lines like the one I used before, though that one is a bit risqué. Usually, it’s more like ‘Take me in your strong, muscular arms, ravish me, and make me yours!’ or ‘Make me a woman! My womanly treasure is soaked in anticipation of feeling your throbbing manhood!’”

“People read stuff like that?” I asked, shaking my head.

“I do! Reading those books is my guilty pleasure. I also read things like the Dostoyevsky novel we discussed. So, are you ready to ‘put your sword in my hot, wet sheath’? Or ‘put your swollen loins in my fiery furnace’?”

“Only if you promise not to use any more of those lines!” I chuckled.

“You’d prefer ‘Take me in your arms, throw me on the bed, and fuck me!’ or ‘Break my cherry!’ or ‘My wet pussy is begging for your hard dick!’”

I couldn’t help but laugh, “I’m not sure which is worse! Not that there’s anything wrong with what you just said, but it doesn’t fit your character.”

“Sure it does! The private one, not the public one. Shy, prim, proper, and virginal is my public persona; this is the real me, but almost nobody gets to see this persona. Actually, that’s a bit misleading — you are the first person to see this persona. And probably the last for some time. Now, can we quit talking? I want you to pick me up, carry me upstairs, and,” she smirked, “fuck my brains out!”

There really was only one thing left to do. I set down my mug, took Jeri’s from her and set it down, then turned and scooped her into my arms. She was really light, and nearly a foot shorter than I was, so I had absolutely no trouble carrying her up the wide, sweeping staircase.

“Second door on the left.”

I turned into the open room, then stopped so Jeri could turn on the lights with a switch by the door. I used my foot to push the door closed, then carried Jeri to the bed and laid her on it.

“Go across the hall and get the robe, slippers, and toothbrush that Karolin will have laid out for you.”

I did as instructed, and when I came back into the room, Jeri had turned down the bed, turned on a dim lamp, turned out the bright overhead lights, and put on some music. I put the things I’d retrieved on the desk then turned to face her.

“Except my gynecologist, nobody has seen what you’re about to see since I was five.”

I nodded and waited, reasonably sure that’s what she wanted me to do. That was confirmed when she pulled her light-blue fuzzy sweater over her head, then slowly unbuttoned her white blouse, revealing a flat stomach, and, when she had shrugged off the blouse, a white lacy bra covering small breasts. Her black slacks went next, along with her socks, revealing white lace panties which matched the bra.

Jeri didn’t pause, reaching around to release her bra, and put her small, firm breasts with hard nipples on full display. I watched in anticipation as she hooked her fingers into her panties, drew them down, and tossed them aside, striking a sexy pose. My eyes focused on the neatly trimmed V of brown pubic hair, and the delights which the point of the V directed me to, and which caused the reaction I was sure she intended.

“What do you think?” she asked with a confident smile.

“Very sexy,” I replied.

“Take off your clothes,” she instructed. “I want to see what a man looks like.”

I nodded and began undressing at a similar speed to how Jeri had undressed, starting with my button-down shirt, then my t-shirt, slacks, and socks, leaving me in my briefs which barely contained my erection. I looked Jeri in the eyes, then carefully pulled the elastic waist of my briefs away from my body, and drew them down, allowing my manhood to spring free.

“Wow!” Jeri gasped. “It’s huge!”

“That’s YOUR fault!” I chuckled.

“That it’s hard? Yes. That it’s that big? Genetics! Now, come over here, please.”

I moved to stand close to Jeri, who winked, sat on the bed, and put her hands on my hips. With a gentle tug, she encouraged me to move closer, which I did. Jeri leaned forward and kissed the tip of my dick, moved her hands to my butt cheeks, parted her lips, and took the head of my dick into her mouth. I groaned softly as she sucked gently and slid her tongue around. After a minute she released me and looked up.

“You like that?” she asked saucily.

“Yes,” I breathed.

She smiled and took the head of my dick into her mouth once again, closing her lips around me, sucking, and swirling her tongue. After a few gentle sucks, Jeri used her hands which she had on my butt to pull me slightly closer, while moving her head as well, slowly taking me further into her mouth. She gagged slightly, causing her to back off until her lips were around the very tip of my dick. She sucked gently, then slowly took me into her mouth again, getting a bit more of me into her mouth. She drew back again, this time releasing me completely so she could run her tongue along the length of my shaft.

A fleeting thought that Jeri wasn’t quite as inexperienced as she seemed formed in my mind, but it vanished, with all rational thought, when she took me back into her mouth and sucked hard, taking me even deeper than she had before. She released me once again, ran her tongue along my shaft, then closed her lips on the tip of my dick and sucked gently before opening her mouth and taking me about two-thirds of the way in.

She pulled back again, but this time she didn’t release me, she simply swirled her tongue around the head of my dick, then took me deep into her mouth again. She began moving her lips up and down my shaft, and every fifth or six time, she’d stop so she could swirl her tongue and suck.

It didn’t take long before I felt the familiar twinges and the sixth time she swirled her tongue and sucked, I groaned and came hard, firing a jet of cum into her mouth. I put my hands on her shoulders for balance, and Jeri swirled her tongue faster and sucked harder as each spurt left my dick. She continued sucking and lashing me with her tongue until she was sure I was done, then took me as deeply into her mouth as she could, and sucked gently for a minute or so before releasing me.

She stood up and presented her lips for a kiss, which I couldn’t possibly refuse. We put our arms lightly around each other, and I lowered my head so that our lips touched. Hers parted and her tongue sought mine for a French kiss. She’d swallowed, so it wasn’t too bad, and when she stepped forward so that her hard nipples rubbed my chest, all conscious thoughts vanished and our tongues tangled in a deep, sexy French kiss, which lasted a couple of minutes.

“That was my first ever kiss, and it was after a guy came in my mouth for the first time,” Jeri smirked.

“You never ever kissed anyone before?”

“No. Well, kisses on the cheek, but that’s it.”

She tightened her arms a bit, pressing her body against mine, so I did the same. Jeri put her head on my chest and swayed just a bit.

“First ever slow dance, too,” she giggled. “And we’re naked! It feels awesome!”

“It does,” I replied, squeezing my arms to pull her snugly against me.

“Not bad for learning from a book, was it?”

“You read a book?” I asked.

“You’re reading manuals to study to be a trader, right?”

I laughed, “Sure, but ... never mind, I’m being an idiot!”

“A problem most men have, at least on occasion.”

“What book?”

The Joy of Sex! It’s illustrated!”

I laughed, “So, kind of like the Kama Sutra?”

“Yes, though the Kama Sutra has lots of relationship advice. Well, if you get the original one, not the one intended just to show off hundreds of sex positions without the advice. You’ve read that?”

“It was suggested by a friend of mine.”

Jeri raised her head from my chest for another sexy French kiss, and after kissing for a bit, I scooped her up and laid her on the bed, then climbed in after her. We kissed a bit, then I moved so I could suckle her breasts and tease her nipples with the tip of my tongue. I spent several minutes enjoying each of her small breasts, before I kissed my way down her chest and stomach, until my lips reached soft, brown pubic hair.

I gently spread Jeri’s legs, moved between them, and planted a soft kiss on the inside of each thigh, my nostrils filling with her musky scent. I touched my lips to her glistening labia, causing Jeri to sigh deeply and that first hint of her juices on my lips causing me to begin to get hard again. I pressed the tip of my tongue between her plump labia, and slid it up and down, enjoying the strong, musky flavor.

After several licks, I slowly and gently pushed my tongue further in, and discovered something I’d never run into — a thin ring which mostly closed Jeri’s tunnel. Bev hadn’t had a hymen, and hadn’t bled, which she attributed to our wrestling matches, and neither Teresa nor Lily had bled. I carefully ran my tongue in small circles, then closed my mouth around the upper part of Jeri’s labia, sliding my tongue up to touch her clit.

“Ooooohhh,” she moaned, “right there!”

I slipped my hands under her firm butt and pulled up gently to increase the pressure as I pleasured Jeri with my lips and tongue. Jeri began rocking her hips, and a moment later, started moaning between labored breaths. Two minutes later she groaned loudly, thrust her hips upward, and shuddered.

“Keep ... going...” she demanded with an urgent whisper between gasps of breath.

I very much enjoyed what I was doing, so I was very happy to oblige, and the blowjob had taken away any serious urgency, though my dick was twitching in anticipation. Jeri’s orgasm lasted a long time, and I continued pleasuring her after it subsided, wanting to give her at least two before, and I nearly laughed at the thought, I plunged my throbbing manhood into her volcanic depths! Jeri had a second orgasm, moaning loudly and pulling my face into her pussy with her hands.

“More...” she gasped when the orgasm passed. “More!”

She had three more before she moved her hands from the back of my head to my cheeks, and I looked up.

“I think I need to be on top,” she said through labored breaths.

I moved so that my head was on the pillow and Jeri straddled my hips, and leaned down for a kiss as she flexed her hips to slide her slick labia along my shaft.

“Interesting taste,” she said, breaking the kiss. “Do you like it?”

“Yes!” I exclaimed.

Jeri smiled and kissed me again, then raised up and grasped my shaft, holding me upright. I felt her labia touch the tip of my dick, then slowly part as she lowered herself onto me. Almost immediately I came into contact with that ring of flesh, and Jeri stopped moving. She took a deep breath, let it out, then pushed down hard, causing me to tear her hymen and embed about two inches of my shaft inside her. Jeri paused for a moment, then raised up so that I was no longer inside her, and looked down to see the head and top of my shaft red with her blood.

“Virgin blood,” she breathed.

“Are you OK?”

“It was like a pinch,” Jeri replied. “I just wanted to see it.”

I nodded and waited, and Jeri grasped my shaft, positioned herself, then slowly sank down on me, my glans parting her walls and her labia gripping my thick shaft.

“All the way in,” she whispered. “So full...”

She began grinding against me and I lifted my hands to her breasts, rubbing her nipples with my thumbs. Jeri continued her relatively gentle movements until she had a small orgasm, which felt really good to me as her pussy rippled around my dick, gently massaging it. Jeri leaned down and kissed me, then moved her lips close to my ear.

“Now,” she whispered, “you can fuck my brains out. As long and as hard as you can.”

She lifted off, lay down on the bed, and spread her legs wide. I moved over her, propped myself on one hand, and used the other to line myself up so I could slide into her. Jeri wrapped her legs around me, and propped on my hands, I began gently thrusting in and out of her, slowly increasing the speed and force of my movements, until we were fucking hard.

Having already cum once, I knew I could last a long time, and I did, going twenty minutes before pushing deep inside Jeri as cum blasted from my dick. She ground against me, and had a good orgasm, the fifth one from fucking, which milked me dry. When both our orgasms passed, I gently pulled out and turned on my back next to Jeri, and put my arm around her. She threw one arm and one leg over me and snuggled close.

“Glad you decided to take me up on my offer?” she asked.

“Very!”

She lifted her head and looked down, shifting so she could see, which also gave me a good view. There were red streaks on her thighs, and my shaft was reddish-pink. She smiled in satisfaction, then put her head back on my chest.

“Competent?” I asked.

“I’d say!” Jeri replied, laughing softly. “I’ll take a few more of those before we go to sleep and a few in the morning!”

“I’m happy to oblige! You’re sure you’re OK?”

“Other than having my insides scrambled by that monster you have between your legs, yes! And I am NOT complaining about the scrambling! In fact, I want them scrambled again as soon as you can go!”

We had two more vigorous fucks before Jeri led me to the shower so we could clean up before we slept. The shower was fun, though beyond a bit of kissing, all we did was wash each other before drying off. We brushed our teeth, then changed the sheet on the queen-size bed so neither of us had to sleep in the wet spot, then got into bed. Jeri snuggled close, I wrapped my arm around her, and we quickly fell asleep.

January 3, 1982, Chicago, Illinois

I awoke to a strange sensation and realized it was Jeri gently licking my semi-erect shaft. I’d never been awakened that way, though I’d only ever slept overnight with a girl a few times.

“Good morning,” Jeri said. “Like my alarm clock?”

“Yes!”

“Think I can make your cock crow?”

I groaned, “Is that from your novels?”

“No, but it’s the same style!”

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