Climbing the Ladder - The First Rung - Cover

Climbing the Ladder - The First Rung

Copyright © 2015-2023 Penguintopia Productions

Chapter 34: Ending the Year With a Bang

Coming of Age Sex Story: Chapter 34: Ending the Year With a Bang - '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 31, 1981, Greater Chicagoland, Illinois

“Imagine,” she whispered, grinding her crotch against mine, “doing this lying down, with my legs wrapped around you.”

Oh, I could imagine, and it had what I was sure was the desired reaction — my jeans became uncomfortably tight, and Sally rubbed against my hard shaft, though it was separated by her panties, her jeans, my jeans, and my briefs. As I struggled to avoid making a mess, I marveled at the number of girls who were coming on to me.

If I took advantage of every opportunity, I could easily have two dozen girls before I had to make a decision about Bev. My biggest concern then would be having the willpower to resist girls who came onto me once I was in a committed relationship, no matter with whom it might be. Most of the Suits took full advantage of their situation, married or not. That was something I resolved never to do. But before then ... well, I could just enjoy it.

Those fantasies, which could be reality, did have to be controlled, including the one about Sally. I’d been paired with Phoebe, and I was going out with Allyson the next day, so it seemed a bit tacky to try to do what Sally had suggested. But that didn’t prevent the fantasy playing out in my mind of her long legs wrapped around me in bed.

“Yeah,” I whispered back, trying to be non-committal so as not to put myself in a bad spot with Allyson or Phoebe.

The song ended, and I excused myself to use the bathroom, where I willed my erection away. Thankfully, it went away after a few minutes, so I took a leak, washed my hands, and returned to the great room, and went to the cooler to get a Coke. Allyson came up to me and stood close.

“Problems?” she asked with a smirk.

“Only temporary,” I chuckled.

“There’s a guest room upstairs, first door on the left. We’ll dance again after Twister, before midnight.”

“That seems kind of tacky,” I replied.

“Partners are only for the games and the kiss at midnight.”

A couple of other people came over to the cooler, so Allyson directed me to the far end of the room by the patio door.

“Can I ask something?” I inquired.

“Sure.”

“If you like me, what’s the deal?”

Allyson smiled, “I do, but I know you don’t want to go steady, and I’m OK with that. And tonight is basically a free-for-all, if you will. I’ll have you all to myself tomorrow! I’m not the jealous kind, obviously, and I actually horned-in on you and Kristy, so it’s not like I could complain without being a real bitch.”

“And Phoebe?”

“Well, if you guys win, she’s going to share the prize with you! And, as I said, everyone knows it’s only for the games and midnight. I guarantee you others will do the same thing, and not with their partners. I mean, I know for a fact two of the girls are virgins, and they won’t do that, but their guys are free to do it with other girls, if they’re willing. Actually, I only know for sure about Kristy, me, and Abigail, so there could be five virgins, or only two, Trust me, it was all discussed beforehand. Nobody here will be catty or jealous. At the last party, Abigail was with a different guy than she was paired with for the games and nobody was upset.”

“I’m curious — what happens if someone starts going steady?”

“Then they don’t come to THIS kind of party. We had a few times like that in High School when we had ‘Spin the Bottle’ parties and couples who were steady just didn’t attend. We had other parties that were meant for couples or bringing a date.”

I’d heard rumors of those kinds of parties starting in Junior High, but I’d never believed them, and neither had Bev. But we were socially isolated, so it was entirely possible the stories were true, and we’d missed out because we spent all our time together. The question was, would Phoebe be upset if I took Sally up on her offer? Asking directly seemed extremely tacky, as I’d said, and that made it very unlikely.

“OK,” I replied, then temporized, “I’ll play it by ear.”

We rejoined the group and Kristy and Allyson unfolded two Twister mats. I’d never played, but I knew the concept. My only concern was possible entanglement with another guy while wearing just briefs or boxers, but I decided that wasn’t an uncrossable line.

“Two teams on each mat,” Allyson said. “Points are scored when someone falls or can’t complete the required movement. That means each round will have either two or three points, with scores of 2-0 or 2-1. Everyone will get three rounds against a random couple, so the maximum points you can score are six. If Jonathan and Phoebe score six points, they’ll win.”

Phoebe squeezed my arm, and said quietly, “We have to win!”

“I’ll do my best!”

“James, would you stoke the fire, please? Everyone is going to strip down to their underwear. Guys that means briefs or boxers; girls, that means panties and bra. Everything else comes off!”

James did as Allyson asked and everyone else began undressing. I scanned the room, taking in the gorgeous female flesh that was being displayed, even if the most important parts were still covered. All the girls were in decent shape, which I remembered was true of the Prep girls at Goshen High. Sally was the thinnest, with small breasts and a flat stomach, and her bare legs were flat-out gorgeous; Abigail had very nice curves and her bra barely contained her ample breasts. I decided, after surveying the girls, that I was absolutely a ‘leg and ass’ man, rather than a ‘breast man’ as the guys back home I occasionally hung out with were.

Allyson drew random marbles and the first two ‘bouts’, as it were, were Sally and Ted with Tara and Jake, and Abigail and Paul with Bianca and Mick. Allyson spun the spinner, and the game began with ‘left foot, red’.

“Teams cannot use the same spot,” Allyson added. “But it’s OK to use the same spot as the other team. You can steady yourself anywhere on the mat with your hand, but off the mat, or any body part other than hand or foot, and that’s a fall.”

She spun a total of four times before the first person fell, giving Tara and Jake a point. In the end, the scores were 2-1 on both mats, with Tara and Jake and Abigail and Paul having two points, That was good for us, as neither of the teams who scored two points was close enough to pass us.

When it was our turn, we were paired with Allyson and Barry, and Kristy and James were paired with Julie and Tom. Bianca spun and called out ‘right hand, green’, and all four of us moved to pick a green circle. The next spin was ‘left foot, red’, which was fairly easy to accomplish. The same was true for ‘right foot, yellow’, as was the next spin, ‘right hand, blue. Things became complicated with ‘left hand, green’, and as she tried to move, Allyson bumped Barry, and he fell, giving us a point. Three spins later, Allyson fell, trying to move her leg underneath Phoebe to get it to a yellow circle. meaning we won 2-0. The other mat had Kristy and James winning 2-1.

The match proceeded with Phoebe and me winning 2-1 against Julie and Tom, but losing 2-1 against Sally and Ted, with Phoebe falling in the first, and me ‘falling’ in the second, though it was because my knee touched the mat as I moved. The final score meant that we had won, and Phoebe was ecstatic. She gave me a very nice kiss and a tight hug as thanks.

James and Jake folded up the mats and put them away, and everyone got dressed. I would very much have liked to dance in just my briefs, but I didn’t want to show off an erection any more than I wanted to see one. Once everyone was dressed, we had about an hour before midnight to dance. I danced with Phoebe, then Allyson, then Kristy. After the third dance, I went to use the bathroom, and when I returned, Phoebe grabbed my hand for another dance.

“Allyson told me what Sally wants,” she said quietly. “I want that, too, but I want my first time to be special, and fall asleep together afterwards.”

“You’re a virgin?” I asked quietly, not believing how things were developing.

Phoebe kissed my cheek.

“Yes,” she said quietly. “It’s OK if you want to be with Sally tonight. I want to make love with you in the hotel for hours, then fall asleep in your arms.”

“I like how that sounds,” I replied. “Do you know the details about the voucher?”

“We just need to call to make a reservation.”

“What about your parents?” I asked.

“Kristy will cover for me,” she said. “I mean, I’m eighteen, so it’s none of my parents’ business, but it’s easier if they don’t know why I’m out for the night! I can call the hotel after our dance and see what they have available.”

“That sounds good,” I replied. “Very good, in fact. Birth control?”

“I’m on the Pill. I thought my first time might be tonight, so I got a prescription about six weeks ago. Then when I heard about the prizes, I decided I wanted to win!”

“What if you didn’t want the guy who you were paired with?”

Phoebe laughed softly, “There are two rooms in the suite! But after that first kiss we had, I was sure I wanted you. I’ve just been waiting for the right guy to come along. But not here, where we’d have to rush, and couldn’t sleep together afterwards because I have to be home by 2:00am.”

“And if we hadn’t won?” I asked.

She laughed softly, “Then I probably would have done it tonight with you. No, I’m sure I would have! But honestly, I want the night in the hotel, because it will be perfect! Do you have any nights you can’t do it?”

I shook my head, “No. I’m free whenever. Well, not tomorrow, because I have a date with Allyson.”

“She told me! I’d go out with you if you asked, but that can wait until after the hotel!”

“So our first date...”

“ ... will be lots of fun!” she exclaimed, then kissed my cheek.

Phoebe and I finished our dance and, as I could have guessed, Sally came over and asked me to dance. We wrapped our arms around each other and pressed our bodies together and swayed to the music.

“I want you,” Sally whispered in my ear. “I need you!”

She planted gentle kisses on my neck, each one increasing my desire. I could think of no good reason not to, and with what amounted to ‘permission;’ from both Allyson and Phoebe, it seemed silly to turn down a girl who wanted to go to bed with me.

“Birth control?” I asked, taking zero chances, despite Kristy’s assurances.

“Every girl here is on the Pill,” she replied. “And nobody will say anything. Tara and Ted already disappeared.”

“Is there more than one guest room?”

“They’re in the library.”

That answered the question which had formed in my mind about Ted, who was Sally’s partner. He was obviously not going to complain about me being with Sally if he was with Tara. I wondered how that had come about, then realized probably the same way my situation had. But curiosity got the best of me.

“Why me and not him?” I asked.

“He’s about five inches shorter than me! You’re the only guy who’s taller, though James is about the same height as me. I prefer guys my height or taller.”

“You’re pretty tall,” I replied.

“All legs, too!” she said with a sultry smile. “I play volleyball at Northwestern.”

“Freshman?”

“Sophomore.”

“What major?”

“Phys ed with an education minor. I plan to be a High School gym teacher.”

The song finished, and Sally released me then took my hand. I willingly let her lead me to the staircase, then up to the second floor and into the first room on the right. She turned on the light, shut and locked the door, then turned to face me.

“We only have about forty minutes,” she said, pulling her polo shirt over her head.

We shed our clothes and both stood and looked each other up and down. She had absolutely no pubic hair, something that I’d never seen, though my experience was obviously limited.

“I was on the swim team in High School,” she said noticing that I’d noticed. “Most female swimmers shave, and I liked it that way, so I decided to keep it. And you have a VERY nice package!”

“Thanks,” I replied.

“Let’s put that to good use!”

We moved into each other’s arms, French kissed, and pressed our bodies tightly together. I ran my hands over her back and her firm butt, and she did the same to me. We kissed for a few minutes before we moved to the bed and pulled down the bedspread, blanket, and top sheet.

“I need you to lick me to make sure I’m wet enough,” Sally said as we climbed into bed.

I had zero objections, though I started by suckling on the nipples of her very small breasts. She wasn’t flat-chested, and it dawned on me that having large breasts would probably preclude swimming, as the kids on the High School swim team back home had all been tall and relatively thin. After a few minutes, I kissed my way down to Sally’s bare mons, which was as smooth as could be. I slipped my arms under her legs, and pushed my tongue between her labia. She tasted VERY good, and I licked and sucked until she was dripping wet, then moved up and positioned the head of my dick against her.

I looked into her eyes, she nodded, and I pushed into her silky folds. I had no trouble burying myself in her, and as she’d promised, she wrapped her legs tightly around my butt, then wrapped her arms around me.

“I like it hard and fast,” Sally said breathlessly.

I was more than happy to oblige and after a few moderate strokes, we began fucking hard and fast, just as she’d requested. It wasn’t really possible to kiss, so I put my head next to hers and simply pounded her into the mattress as she moved her hips with wanton abandon. Soon, we were both breathing hard, and our bodies became slick with sweat. Sally had one orgasm before I came and a second one as the third spurt of cum left my dick. When our orgasms passed, I stayed on top of her, and she kept her arms and legs wrapped around me.

“I guessed right,” she said after a couple of minutes. “That was awesome!”

“We have time for another round, if you want.”

“I’m not going to say ‘no’ to a guy who’s hung and knows how to use it!”

We had a second energetic fuck before sneaking across the hall to the bathroom for a joint shower. After we had rinsed off the sweat and other fluids, we dried off and wrapped towels around us to go back to the guest bedroom to dress. Once we dressed, we exchanged a nice French kiss.

“Thanks,” she said. “That was lots of fun!”

“I agree,” I replied.

We exchanged another kiss, then headed back downstairs. Allyson came over to me and took my hand for a dance.

“Have fun?” she asked quietly.

“Yes, I did!” I replied.

“Did you want me to invite Kristy for tomorrow night?”

“No,” I replied. “Unless you really want that, I prefer our date to be just the two of us.”

She squeezed her arms tightly around me to show her appreciation, and making it clear I’d given the right answer. I actually would have loved to have another threesome, but given how Allyson had treated me, I felt having a one-on-one date was the right thing to do.

When the song ended, Phoebe took Allyson’s place in my arms for a dance.

“The hotel actually had a suite available next week, Saturday; I booked it. We can have the room from 1:00pm Saturday until 10:00am Sunday.”

“Sounds good!”

“I was thinking about the Shaw’s certificate and the Marshall Field’s certificate and we could use those on Friday evening, if you wanted, so that we don’t waste a second of time on Saturday!”

“That’s fine,” I replied.

“Then I can buy a sexy negligée! You can help me pick it out.”

“That sounds like fun!” I agreed.

We finished our dance and then I danced with Julie, Kristy, and Bianca, each in turn, before Allyson got everyone’s attention for the midnight countdown. She and Kristy poured champagne in the glasses, finishing with about thirty seconds to go. Everyone got their glass, and we counted down from ten. At midnight, after exclaiming ‘Happy New Year!’, everyone drank their champagne and kissed their partner. The French kiss with Phoebe was really nice and held the promise of a very enjoyable night in the hotel in a weeks’ time.

January 1, 1982, Greater Chicagoland, Illinois

After everyone had a second glass of champagne, Allyson went to the kitchen to rinse one of the bottles, and when she returned got all the guys into a large circle on the floor.

“The girls will spin, and French kiss whichever guy the bottle points to for one minute. When all the girls are done spinning, we switch places and the guys spin for the second round, and so on.”

My luck was good, with Allyson and Phoebe both spinning me. When we switched, my spin was Bianca, and I very much enjoyed a French kiss with her. In the third round, only Abigail spun me, and then I spun Sally, very much enjoying both kisses.

“Next round, kissing, but also touching above the waist,” Allyson said. “Girls decide if it’s over their shirt, over their bra, or skin.”

I had the pleasure of having Abigail and Kristy both spin me, and to my extreme delight, Abigail unhooked her bra and allowed me to play with her large breasts for a full minute while we kissed. Kristy did the same, as did the other girls except for Julie, Tara, and Phoebe, who only allowed the guys to touch them over their shirts. When it was my turn to spin, I was delighted to spin Abigail again, and fondled her for the full minute while we French kissed.

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