Climbing the Ladder - The First Rung - Cover

Climbing the Ladder - The First Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 31: When It Rains, It Pours

Coming of Age Sex Story: Chapter 31: When It Rains, It Pours - '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  

December 21, 1981, Chicago, Illinois

The weekend had been very quiet. I’d done my laundry and grocery shopping solo, and had spent Sunday alone, as Tom was on shift and couldn’t host the usual gathering. I’d thought about calling Teresa or Nicki, but in the end, decided it was better to just spend the day reading and relaxing. That meant that on Monday I was fully refreshed and ready to go, with a short work-week ahead of me before I headed to Goshen for Christmas.

“How was the party?” Kristy asked when she arrived early on Monday afternoon.

“It was OK. I was surprised I didn’t see you there.”

“Temps weren’t invited. Did your girlfriend enjoy the party?”

“I went stag,” I replied. “Lily and I broke up.”

“That was the personal stuff you didn’t want to discuss last week, wasn’t it?”

“Yes.”

“And why you said talk to you this week, right?”

“Yes, otherwise it would have been a flat ‘no’.”

“You should have let me know, because then I could have gone as your date!”

“Sorry about that.”

“So you’re a free man now, right?”

“I suppose so.”

“What are you doing tonight?”

“I had planned my usual evening of dinner, reading, and studying for my talk with Mr. Matheson about moving upstairs at some point.”

“If you want company...”

It was absolutely a tempting offer, but I felt it too soon to have a girl over to the apartment, not just because I didn’t want to hurt Lily, but also because I couldn’t predict Mr. Andros’ reaction, and that meant being careful about how I conducted my personal life. I wasn’t sure how soon would be ‘too soon’, but I was sure that a week was not enough time.

“I rent my apartment from my ex’s dad, so that might not be the best idea. What about your place?”

“I don’t think my dad would accept us going to my room together! I turn nineteen in February, but living at home has rules. You think her dad would kick you out?”

“I don’t know, and I don’t want to find out. I think at least a couple of weeks need to pass before I invite someone over, and even then, spending the night might raise some eyebrows.”

“I assume you plan to move?”

“August 1st. I’ll start looking in March.”

“Well, this sucks. Uhm, you know what, let me make a phone call on my break. My best friend, Allyson, is living in the dorms at Loyola and maybe we could use her room. She was one of the girls who went to Europe with me after graduation, though she only stayed eight weeks.”

“She lives in the dorms? She isn’t from Chicago?”

“We live in the far west burbs, so it makes sense. I’m not sure if the dorms are still open because her last exam was on Friday. Are you OK with me calling her?”

I was simply amazed at the opportunities for no-strings-attached sex I’d had since moving to Chicago. I had taken advantage of some of them, and turned down others. I very quickly decided there were no good arguments against being with Kristy, and realized I really wanted to be with her.

“Sure, why not?” I said.

She went to the desk and I got back to work. I was busy all afternoon, but on one of my brief trips back to the mailroom, Kristy told me that her friend would meet us at Loyola at 7:00pm, which gave us time to get dinner at Bennigan’s. I ended up working about twenty minutes overtime before I could leave, though Kristy had to go down to the lobby to wait for me.

Dinner was good, and I thought it wasn’t too expensive, Kristy insisted we split the bill as we weren’t on a date. I had no objection, as going out to dinner often would quickly eat into my disposable income. When we finished, we walked to the subway and rode north to Loyola, then walked to the dorms.

“Jonathan, Allyson; Allyson, Jonathan.”

Allyson was a cute, compact blonde.

“Damn!” Allyson exclaimed. “Kristy? Majorca?”

“I’m game!” Kristy exclaimed.

“Majorca?” I asked.

“An island in the Med,” Kristy replied. “But she’s asking if she can join us.”

“Join us?” I asked not believing what had flashed through my mind.

“He looks like a deer in the headlights!” Allyson declared. “Never had a threesome, Jonathan?”

“Uhm, no,” I stammered, not believing what I was hearing.

“Well, if you’re game, you’re in for the time of your life!”

What they were offering was something I’d never even dreamed of, let alone considered a real possibility. I couldn’t imagine opportunities like this occurring very often, and I knew I’d kick myself if I turned it down and never had another chance. Of course, I thought, suppressing a chuckle, the way things were going with regard to sex, there might be other opportunities.

The one thing that gave me pause was the way things were at Spurgeon, but this wasn’t me coming onto the girls, or enticing them with gifts, or whatever, this was two girls who wanted to have sex with me, together! As I imagined how that would work, a new, and even more intriguing idea popped into my head — that the girls would do things with each other! If I had ANY reservations, that thought killed them, as that was something I simply HAD to see, and I wasn’t going to miss the chance!

“I’m game,” I said.

Allyson opened the door to the dorms with her key, then Kristy took my hand and led me into the building. Allyson followed us, and we went to the elevator which took us to the fourth floor. We walked down a hallway, and stopped in front of room 408, which Allyson opened with her key.

“I am SO glad my dad sprang for a single room!” she exclaimed. “Prevents any roommate problems when I entertain!”

Something dawned on me that I should have thought of much, much earlier.

“I don’t carry rubbers with me,” I said.

“Not a Boy Scout?” Allyson asked.

I shook my head, “No time. I worked two jobs, sometimes three, while I was in High School.”

“Don’t sweat it!” Kristy declared. “We’re both on the Pill.”

Allyson flipped on a light switch, then closed and locked the door. She and Kristy exchanged a look, then quickly stripped down to their bras and panties. Not being a complete idiot, I followed suit, keeping on my briefs, which were already feeling overly tight. Not having any idea how a threesome worked, I held out my arms and the girls stepped into them. I used my left arm to pull Allyson against me, and my right to pull Kristy against me.

Both girls lifted their heads for a kiss, and I chose to kiss Kristy first, as she was the one who had invited me and in my mind had ‘dibs’. We exchanged a soft kiss, then I switched to Allyson who received an identical kiss. Moving back to Kristy, we started French kissing, and I felt one of the girl’s hands on the front of my briefs. The owner quickly revealed herself.

“Jesus, Kristy!” Allyson exclaimed. “He’s HUGE!”

I felt a second hand, certainly Kristy’s, slip inside my briefs and grasp my shaft which was quickly swelling due to inrushing blood.

“Wow!” Kristy gasped. “I have to see it!”

Kristy released me and I felt two pairs of hands pull my briefs down to my knees, allowing my dick to spring free. The briefs slid down to my ankles and I kicked them off. The girls stepped back and simply stared at my erection. I’d been told I was big, but I honestly had nothing to compare myself to, as I’d never seen an erection other than my own, and had zero desire to do so.

“I think you two have on too many clothes,” I grinned.

The girls quickly stripped off their bras and panties, and Allyson removed any doubt about being a natural blonde. I held out my arms again, and the girls quickly moved into them, pressing their firm bodies against mine. I French kiss both of them, and then they gently pushed me towards the bed.

“How quickly can you get it up after you cum?” Allyson asked. “And how many times do you think you can cum?”

“It doesn’t take long,” I replied. “And I’ve managed eight.”

The girls knelt on the floor in front of me, and I leaned back on my elbows so I could watch them, having a pretty good idea of what was going to happen next. The girls lowered their heads and I nearly lost it at the sight and feel of two tongues on my shaft. they ran their tongues up and down along my shaft, and each time they reached the head, they kissed each other.

After a few minutes, Kristy took the head of my dick in her mouth and sucked gently, while Allyson continued pleasuring me with her tongue. The girls switched off and Allyson took me into her mouth, and began bobbing up and down, sliding her tongue as she moved. The vision and sensation of the joint blowjob had me on a hair-trigger, and I wondered how long I could last. It had been long enough, I thought, that I wouldn’t embarrass myself, but I had no clue what the girls wanted, so I simply let nature take its course.

A minute later, I twitched, making it obvious to all three of us that I was about to cum. Allyson began bobbing faster, and one of the girls cupped my balls in her hand and squeezed ever so gently, which was enough to send me over the edge. I groaned and cum spurted into Allyson’s soft mouth. After the second spurt, she released me and Kristy took me into her mouth, catching the fourth spurt, the third having hit Allyson’s lips. Kristy continued bobbing and sucking until my orgasm had passed, then released me. Allyson took me again, bobbed and sucked, and when she released me, the girls shared a sexy French kiss.

I had a pretty good idea of what was coming next, and steeled myself for it. I wasn’t thrilled at the notion, but I wasn’t going to do anything to mess up what was, as Allyson had suggested, looked to be the ‘time of my life’. The girls broke their kiss after about a minute, and then Kirsty gave me a deep French kiss, and, when we broke the kiss, Allyson did the same. When she broke the kiss, the girls knelt facing each other and began kissing. I watched in fascination as they made out, already feeling the first stirrings of an erection, though I hadn’t gone completely soft.

I watched as the girls continued making out, fondling each other’s breasts, and I wondered just how far they might go. I found out about three minutes later when they moved to the bed. I shifted to give them room and they turned and my eyes went wide in wonderment as they began licking each other. I wasn’t exactly surprised that girls would do that, but the idea that I’d ever actually see it done had never crossed my mind.

“Jonathan,” Kristy asked between heavy breaths, “take me from behind.”

I moved behind her, and she shifted slightly so I could press the head of my dick against her slick labia. As I began pushing into Kristy, she moaned softly, and I felt Allyson’s tongue on my shaft. I groaned in pleasure, as just the idea of what I was doing seemed to be nearly enough to make me cum. I managed not to, and embedded myself fully in Kristy’s silky tunnel. I pulled back, then slowly pushed into Kristy again, and began slowly fucking her as she licked Allyson and Allyson alternated between licking Kristy and licking my shaft when it was exposed.

Both girls had orgasms before I had mine, pushing as deeply into Kristy as I could, her pussy spasming around my shaft as I fired jets of cum into her. The three of us lay together in the same position to catch our breath, and after a few minutes, I softened and slipped from Kristy. She turned on her back, and Allyson moved so that she could take my softening shaft into her mouth. She licked and sucked me clean, then continued bobbing, licking, and sucking with the obvious intent of getting me hard as quickly as possible. It came as no surprise to me that it didn’t take long, given I very much wanted what I was sure was next — fucking Allyson.

Allyson released me, then confused me by getting out of the bed. She went over to the closet, opened it, and took a bottle from the shelf.

“Sit up,” she requested.

I did as she asked, moving so my legs were over the edge of the bed. Allyson opened the cap on the bottle, which I saw was baby oil, squeezed some into her hand, and then began applying it to my dick.

“Baby oil?” I asked.

Allyson smirked, “You’ll see why in a sec!”

She applied a liberal amount to my shaft and glans, then closed the bottle. She moved to straddle me, wrapping her legs around me and trapping my rock-hard shaft between us. She pressed her lips against mine and we began a deep, sexy French kiss. Allyson ground against me while we kissed, and I squeezed her butt cheeks with my hands, pulling her pussy against my shaft. After a couple of minutes, she broke the kiss.

“Suck my nipples,” she gasped.

She leaned back a bit and I lowered my mouth to her firm breast, taking her nipple into my mouth and sucking as she continued grinding against me. I alternated between her two breasts, sucking each nipple and teasing it with my tongue. Allyson continued grinding against me then, when I released her left nipple, intending to move back to her right one, she lifted up and I felt Kristy’s hand on my shaft. Kristy held me as Allyson pressed her labia against my glans and began to very slowly sink down my shaft.

“Oh ... fuuuuuuccckkkk,” Allyson groaned.

Allyson was very tight, tighter than any girl I’d been with, and even with the baby oil and her own juices, it was slow going as her muscles tightly gripped my shaft. She was panting hard as she worked to get me completely inside her, which she did after moving up and down, taking about an inch more each time, until I felt her pussy lips on the base of my shaft. She put her head on my chest and took several deep breaths.

“Amazing, huh?” she whispered in my ear as she flexed her muscles to squeeze me even tighter.

“Oh, yeah,” I moaned softly.

“Let me,” she breathed.

She wrapped her arms around me, and I did the same with her, and she began flexing her hips, grinding against me while tensing and relaxing her pussy muscles. The pleasure was intense, almost to the point of pain. Kristy moved behind me, placing her legs on either side of me, pressed her breasts into my back, and began nibbling on my earlobe. I nearly came right then, discovering something new about my own pleasure. I was extremely glad I hadn’t lost it, as I wanted to stay inside Allyson for as long as possible. She had two small orgasms over the course of the next ten minutes.

After the second one had passed, Allyson asked me to lie on my back, something I accomplished without pulling out of her. Once I was on my back, Kristy moved so that my head was resting in her lap, and Allyson began slowly moving up and down my shaft. The friction was intense, and I knew I couldn’t hold back much longer.

“Kiss me, Kristy!” Allyson demanded breathlessly.

Kristy leaned forward, shifted, and before I could object, pressed her pussy against my mouth as she began to kiss Allyson. In the next second, all conscious thought vanished as Allyson had a tremendous orgasm which I feared, for a brief moment, might snap off my shaft. Instead, I groaned loudly, though the groan was muffled by Kristy’s pussy. My head swam as cum blasted from my dick, and I reflexively sucked hard on Kristy’s clit, lashing it with my tongue, bringing her off as well.

When all of our orgasms had passed, both girls moved off me and lay on either side of me. I put my arms around them and pulled them close. Each girl gave me a French kiss, then they put their heads on my chest. I almost said something to Kristy about what she’d done, given I’d fucked her, but I realized that saying ANYTHING about that, no matter how I felt, was a quick way to have the girls send me away. Not only was I looking forward to a few more hours of sex, but hoped against hope that I might be with them again.

We lay together for about fifteen minutes, and then the girls used their mouths to get me hard. Kristy moved so that her butt was right on the edge of the bed, had me stand between her legs. She rested her ankles on my shoulders and demanded I fuck her as hard as I could. I did as she asked, and soon I was pounding into her for all I was worth. Allyson moved to straddle Kristy’s face, and Kristy pleasured Allyson with her tongue while I kept fucking Kristy. Both girls had good orgasms before I had mine, once again filling Kristy’s spasming pussy with cum.

After I pulled out, we lay back down on the bed with the girls on either side of me once more, exchanged a French kiss, then lay quietly while we waited so I could get hard again. The thought of being in Allyson again was a very strong motivation for whatever chemicals were necessary to cause me to get hard, and the girls helped once again with their mouths. Allyson mounted me and slowly slid down my shaft. Kristy moved to straddle my face, and despite my stomach doing a couple of flip-flops, I didn’t object because I didn’t want to do anything to interfere with having my rock-hard dick inside Allyson’s extremely tight pussy.

I focused on the intense pleasure, to take my mind off the fact that I was pleasuring Kristy’s pussy into which I’d now cum twice. After a short time, my stomach was no longer roiled and I gave in to the situation and licked and sucked with gusto, as Allyson slowly slid up and down my shaft, occasionally grinding against me and rocking back and forth. Kristy had three orgasms before Allyson had a tremendous orgasm which pulled me over the edge with her. Her spasming pussy milked cum from me until I was spent, and as before, the girls moved off, lay next to me, kissed me, then put their heads on my chest.

“Can I ask what happened in Majorca?” I inquired.

“We met a ridiculously handsome Spanish guy, and he seduced us into our first threesome,” Kristy said.

“You’d never done stuff with girls before?”

“No,” she replied. “That was the first and only time before today. He was fun, but he didn’t have equipment like yours!”

“We basically spent most of our three days in Majorca fucking,” Kristy said. “And we decided we wanted to do it again at some point.”

“Was this planned?” I asked.

“No,” Allyson said. “I drove into the city to bring the keys, but never thought about a threesome until I saw you. Then I decided to ask Kristy in code, so she could say ‘no’ if she didn’t want to. I take it you’re enjoying yourself?”

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