Climbing the Ladder - The First Rung
Copyright © 2015-2023 Penguintopia Productions
Chapter 41: Not if you end up dead!
Coming of Age Sex Story: Chapter 41: Not if you end up dead! - '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 16, 1982, Chicago, Illinois
There was only one word I could think of for the way my life was unfolding — surreal. I had no doubt from Paula’s kiss, or Lucy’s for that matter, where things were likely to end if the girls all agreed to play. And the worst outcome would be seeing all the girls naked. Given I’d played ‘Spin the Bottle’ and ‘Underwear Twister’, I didn’t see any reason not to play with the girls, even if the only thing that happened was we ended up naked and did some making out.
“I’m game!” Sally exclaimed almost immediately.
That didn’t surprise me, given we’d both very much enjoyed being together at the party.
“The ‘crazy redhead’ is game, too!” Lucy declared.
I couldn’t help but laugh along with some of the girls.
“What do you say, Allyson?” Paula prompted.
“If Jonathan is OK with it, sure. Well, and Shelly and Bianca.”
“I already kissed him at your party, Ally,” Bianca said. “And he’s seen me in just my underthings, so, sure, why not.”
“Shel?” Paula asked.
“What are the rules?” Shelly asked.
“Well, with only one guy we need to modify them a bit, but not much,” Paula said. “Normally, if you spin and the bottle points to the opposite sex, you have to make out with that person for sixty seconds; if it points to the same sex, the person has to take off one clothing item. When you’re making out, you can only touch or kiss areas not covered by clothing, except it’s always OK to touch their back.
“With just one guy, whoever the bottle points to gets to make out with Jonathan for a minute, THEN remove one piece of clothing. If the bottle points to Jonathan, you get to make out with him, and he removes a piece of clothing. If the bottle points to you, you have to take off two pieces of clothing, and you don’t get to make out. Which is a bummer!”
“So, what do you think, Shel?” Allyson asked.
“I’ll play, but on the condition that anyone can stop at any point.”
“No fair staying to see the end result if you don’t play,” Paula said.
“If anyone doesn’t want to play, they can go to my room,” Lucy said.
“Which room is yours?” I asked with a silly grin.
All the girls laughed.
“That kind of defeats the purpose!” Paula declared.
“Not for me!” Lucy exclaimed. “He’ll be in my room!”
“OK with you, Jonathan?” Allyson asked.
“Do I look like an idiot?” I chuckled. “It’s really up to you.”
“Let me get an empty Coke bottle from my room,” Paula said.
She came back a moment later with the bottle and ceramic plate.
“It won’t spin well on the carpeting,” she said explaining. “But if we turn the plate upside down, it’ll be perfect.”
“That sounds like experience,” Sally said.
“Duh!” Paula laughed. “We played all kinds of variants of ‘Spin the Bottle and ‘Truth or Dare’ in High School. I gave my first blowjob on a dare!”
“Seriously?” Shelly asked.
“You think that’s wild?” Paula asked. “A friend of mine lost her virginity at fifteen on a dare!”
“No way!” Shelly protested.
“He was a tall, good-looking guy like Jonathan and she wanted to do it, so why not go for it?”
“I suppose,” Shelly replied.
“Socks count as one item,” Allyson said.
Everyone had already removed their shoes in the hallway, so as not to track dirt and salt into the room.
“What if there are differing numbers of clothes?” Lucy asked.
“Those are the breaks!” Allyson declared. “Nobody had advance notice, so it’s the luck of the draw, so to speak. Sally, lock the door, please.”
Sally, who was standing closest to the door, turned the deadbolt, while Paula set the plate upside-down on the floor and the bottle on top of it. Allyson turned on a space heater, which I thought was a good idea, because the room was a tad cold to be naked for any length of time. It would warm up fast, though, because the room was not all that large. The seven of us managed to sit around the plate, surrounded by the couch, desk, and bed, with just a bit of room to spare.
“Who spins first?” Lucy asked.
“Me!” Paula declared. “It was my idea and it’s my bottle!”
“Greedy bitch!” Lucy declared, causing everyone to laugh.
Paula spun and the bottle clattered against the rim on the bottom of the plate, and, to everyone’s amusement, pointed back at Paula.
“Oops,” she said with a laugh.
“Serves you right!” Lucy declared smugly.
Paula shook her head and removed her sweater and blouse, revealing large, full breasts encased in a lacy white bra.
“My toes will get cold,” she smirked.
“Uh-huh,” Lucy snarked. “It has NOTHING to do with wanting to flaunt those 36Ds!”
“If you got it, flaunt it!” Paula retorted.
“Genetics suck!” Lucy declared.
She was wearing a wool sweater, but I could tell she had very small breasts. To me, any breasts I could see, touch, or especially, kiss, were perfect, no matter what size they were. What really got my attention was long legs and a small, firm butt, which was a perfect description of Sally.
“If you suck, most guys won’t care about the size of your boobs!” Sally declared.
“We girls with small tits have to stick together!” Lucy declared. “Because a lot of guys DO care. They walk into a party and the first thing they see is Paula with her gorgeous boobs and after that, they focus on her!”
“Not all guys,” I replied. “Any size is fine with me!”
“Hah!” Lucy declared triumphantly.
“Just spin!” Paula declared, laughing.
Lucy spun the bottle and when it stopped clattering, it pointed to Sally.
“Yes!” Sally declared triumphantly.
She was basically sitting across from me, so she moved the plate and bottle, then scooted over to sit in my lap so we could kiss for a minute. By the rules, that was all we could do, and after a very nice French kiss, she moved back to her spot and following suit, pulled off her sweater. She had on a long-sleeve pullover shirt, similar to my rugby shirt, which was no surprise given how cold it was outside.
Allyson was next and spun, with the bottle pointing to Paula.
She scooted into my lap and we French kissed, though, again, per the rules, there was no touching of anyplace truly interesting. When Paula moved back to her spot, she took off her jeans, leaving her with her socks, lacy bra, and lacy panties which were just translucent enough to show she had a thicket of black pubic hair.
“Slut!” Lucy teased.
“Takes one to know one!” Paula laughed.
I spun, and to both her and my delight, it landed on Sally. We exchanged a nice French kiss and when she moved back to her spot, she took off her socks. Shelly was next, and the spun bottle ended up pointing to me. She moved to my lap and we exchanged a soft kiss, though she didn’t part her lips. When a minute has passed, she moved from my lap and I pulled my rugby shirt over my head.
Sylvia, who had been quiet since we’d greeted each other, spun with the bottle landing on Allyson. We exchanged a very nice French kiss and when she broke the kiss she put her lips close to my ear.
“I’m OK with whatever happens,” she whispered.
I nodded slightly, she moved from my lap, and removed her sweater. Bianca spun next and the bottle landed on Allyson again. She moved to my lap and we exchanged another French kiss, and she removed her socks. Sally spun and everyone laughed when it landed on her.
“How the heck does that happen three times?” Sally asked with a laugh. “Only a 12.5% chance on each spin, and I’ve been spun twice by others and once by myself!”
“Quit stalling!” Paula demanded.
“Chill!” Lucy ordered. “I’m positive you’ll get what everyone in this room knows you want!”
Everyone laughed and Sally removed her long-sleeve shirt and her jeans, showing off a black bra and panties. I was actually surprised at how many articles of clothing had been removed so far, though only by two girls and me. That was quickly rectified when Paula spun and the bottle pointed to Lucy. She moved to my lap and gave me another kiss which screamed ‘I want to fuck’ without her saying a word, then moved back to her spot and pulled her sweater over her head, showing that she had on a thin cotton t-shirt under it.
Lucy spun and it landed on Shelly who once again gave me a soft, but simple kiss before taking off her socks.
“Socks? Really?” Paula asked.
“Everyone gets to decide for themselves,” Shelly replied firmly.
Paula rolled her eyes, “Spin, Ally!”
“Somebody is DYING to get naked!” Lucy teased.
“How long does the game go?” Bianca asked.
“Well, when we played mixed couples,” Paula answered, “it was until either all the guys were naked or all the girls were naked, but that doesn’t really work here. I think it should be when Jonathan and any four girls are naked. Or we could just go until only one person is left, and they just strip so we all show everything.”
I wondered if Shelly would go through with it, but I expected all the other girls would. I got the impression that Shelly would stop before removing her panties, if not before removing her bra, but it really did have to be up to her.
“I like the second option,” Lucy said. “So let’s do that unless anyone objects.”
Nobody objected and Allyson spun, with the bottle lading on Bianca. She moved to my lap and we exchanged a nice French kiss just like the one at the party, though this time the rules prevented me from fondling her breast, at least for now. She chose to remove her sweater, following the basic pattern.
I spun the bottle and it landed on Sylvia, the last one who hadn’t removed any clothing. She moved to my lap and we exchanged a kiss which started out as a simple, soft kiss, but when she parted her lips, became a very sexy French kiss. She moved back to her spot and removed her sweater, while I contemplated my unbelievable luck. Shelly was next, and when she spun, the bottle landed on her. She pulled her sweater over her head, then slowly unbuttoned her blouse to reveal a pale blue bra covering very nice breasts, though they were somewhat smaller than Paula’s.
Sylvia spun and the bottle landed on Lucy, and after another tantalizing French kiss, she removed her t-shirt, and I saw what I thought to be the source of her question — she was wearing what appeared to be a white, tight-fitting, one-piece undergarment. As I thought about it, it made sense, as she certainly didn’t need a bra for her very small breasts, though I suspected she’d want some material covering them to avoid her clothes rubbing her nipples.
Bianca spun me, which meant that after our kiss, I removed my socks.
“Boooooo!” Paula exclaimed.
“Jesus, Paula!” Lucy exclaimed. “Why not just strip and go at it right here on the floor!”
“He’s entitled to choose, and I’m entitled to my opinion of his poor choice!”
Everyone laughed and Sally spun and groaned when the bottle landed on her.
“How is this even possible?” she groused, removing her black bra, then standing up to remove her black panties before sitting back down.
“What happens now that she has nothing else to take off?” Lucy asked.
“She gets three minutes with Jonathan!” Paula declared.
“Hang on!” Lucy protested. “Having no clothes to give is to your advantage?!”
“Yes!” Paula said.
“What happens if you spin yourself when you’re naked?” Lucy asked.
“You lose your turn!” Paula declared. “Have fun, Sally!”
“Watch,” Sally predicted ruefully, “now I won’t get spun for the rest of the game!”
She was wrong because when Paula spun, the bottle pointed right at Sally’s crotch.
“I dare you to complain now!” Lucy smirked.
Sally stuck her tongue out at Lucy and moved to my lap. She placed her lips close to my ear and whispered, “Anywhere.”
We began kissing, and as our tongues twirled around each other I moved my hand to cup her small breast, playing with her nipple for a minute before sliding my hand down over her bare mons and gently massaging her clit through the flesh which covered it. When the three minutes were up, Sally was breathing hard, and I felt a bit sorry for her, as I’d gotten her wound up and there wasn’t anything I could do about it.
Lucy’s spin landed on Sylvia and we kissed, then she removed her socks. Allyson’s spin landed on Bianca, who, after we kissed, also removed her socks.
My spin landed on Lucy, who did everything she could to convey what she wanted with her kiss and squirming in my lap, before she moved back to her spot and to my surprise, removed her jeans rather than her socks. The garment she was wearing was completely form-fitting and I could see the outline of her labia where it disappeared between her legs.
Shelly spun and the bottle pointed to Allyson, who, after our kiss, removed her blouse, revealing the pale green bra she’d put on earlier in the day at my apartment. On Sylvia’s spin, the bottle pointed to me again, and after she and I kissed, I chose to remove my belt, to a derisive snort from Paula.
Bianca spun and a VERY happy Sally moved to my lap to resume our kissing and touching. This time, she shuddered just before time was up, and I was happy she’d had a bit of relief. The problem was, that I’d become somewhat hard and the position I was in made it doubly uncomfortable.
Sally spun and the bottle stopped just short of her, and pointed to Paula.
“Finally!” Paula exclaimed, quickly moving to my lap for a searing French kiss, after which she removed her bra, putting her impressive breasts on full display. I hoped the bottle landed on her again soon, because despite being a self-identified ‘leg and ass’ man, I wanted to get my hands, and hopefully my lips, on those awesome mammaries.
Paula’s spin pointed to Bianca, and post-kiss, she removed her blouse, and then, when Lucy’s spin landed on her as well, her jeans. She had on a pale pink soft cotton bra and matching panties, which were what I remembered from the Twister game at the party.
Lucy spun herself, took off her socks, then stood and quickly removed her one-piece garment, revealing a small thatch of red pubic hair.
I decided to tease Paula and rewarded Lucy with a low whistle.
“Oh, puh-lease!” Paula complained.
“Maybe he likes quality over quantity,” Lucy smirked, winking at me.
“Spin, Allyson!” Paula ordered.
Allyson spun me, and after our kiss, I removed my long-sleeve t-shirt.
“Nice!” Lucy breathed. “Do you work out?”
“I ride my bike and lift weights,” I said.
“Shut up and play!” Paula demanded.
“Jesus!” Lucy laughed. “Look, when you both get naked, you can just fuck him right here in front of all of us!”
“Don’t think I won’t!” Paula declared.
“Uhm, before this gets out of hand,” I said, “and making NO assumptions, I don’t have rubbers with me.”
“I believe everyone here is on the Pill,” Allyson said, “though I don’t know about Shelly.”
“I am,” Shelly said, blushing slightly.
All the other girls nodded.
I spun and Paula looked like she was fit to be tied, because the bottle was pointing to Lucy. She quickly moved to my lap, and I decided I wanted to continue to annoy Paula, because everyone was enjoying the silly exchanges between her and Lucy, and I was sure Paula wouldn’t be angry, just mildly annoyed.
“Any limits?” I asked quietly.
Lucy shook her head and smiled, so I encouraged her to stand, then to sit on the edge of the couch behind me. I turned and knelt in front of her, and we shared one of her tantalizing kisses, though I broke it after perhaps twenty seconds and moved to suckle her small breasts which were capped with small pink nipples. I alternated back and forth, and when there were about thirty seconds to go, I released her nipple, lowered my head between her legs, and pushed my tongue between her labia. She groaned as I flicked her clit, but there wasn’t much time left, so I straightened and we exchanged a short kiss to use up the time.
“Holy ... whoa!” Bianca exclaimed.
“I’m loving this game so far!” Lucy exclaimed, winking at Paula, who gave her a ‘death stare’, something I’d only encountered with my cousin Lisa.
Shelly’s spin landed on Sylvia, who removed her blouse after we kissed, giving me a view of her red bra. After she had removed her blouse, she spun, and then Shelly and I kissed. She removed her jeans, blushing slightly, before sitting back down, her light-blue panties showing a tiny wet spot, telling me that she was excited by what was happening, even if she was a bit shy.
Bianca spun and it landed on me, so after our kiss, I removed my jeans, the bulge in my briefs completely obvious to all the girls. Paula’s eyes went wide and she licked her lips and winked, obviously appreciating what she saw, despite it being covered by my ‘tighty-whitey’ briefs. She wasn’t the only one to notice, as I saw the other girls either staring or sneaking looks.
Sally’s spin landed on Shelly, and we exchanged a soft French kiss, while her hands roamed softly over my back. She returned to her place and slowly reached around and unhooked her bra, then crossed her arms and pushed the straps from her shoulders. She moved quickly to discard the bra, blushing, then crossing her arms over her chest, hiding very nice breasts which I’d caught only a glimpse of.
Paula spun and I thought she’d explode when it landed on Lucy again. Lucy laughed and came over to me, but indicated I should sit on the couch, which I did. We kissed, then she broke the kiss and sucked on each of my nipples in turn, teasing them with her tongue. The pleasure was intense, and I was instantly fully hard. I adjusted myself so my dick wasn’t ‘peeking out’ of my briefs, and at Lucy’s urging, we switched places. After a quick suck on each nipple, I lowered my head between her legs, pressed my tongue into her, and sucked on her clit while teasing it with my tongue. Unfortunately for Lucy, time expired, but she stole a quick kiss before going back to her spot.
Lucy’s spin landed on Bianca, who after a kiss, removed her bra putting what I thought were her perfect breasts on display. They were firm, about the size of half of a large orange, and capped with light-brown nipples and areolae. She was still easily the prettiest girl who had been at the party, and rivaled Shelly, the strawberry blonde who I thought was the prettiest of the seven pretty girls in the room.
Allyson spun Shelly, who nervously came to sit in my lap. Given she was shaking slightly, I decided it was best to just kiss her and fondle her breast, but she surprised me by straddling, me, rather than sitting sideways. She wrapped her arms around me and when our tongues touched, she began grinding against me and rubbing her nipples on my chest. We only had a minute, so it was over before I was ready, and when Shelly moved back to her spot, she took off her panties, and sat down, one arm across her chest and one between her legs.
“Given where this is obviously going,” Paula said. “Once Jonathan is naked, you have a choice. You can take your normal turn, either one minute or three minutes, OR you can go until either you cum or he cums, at which point you retire from the game. Well, assuming Jonathan is OK with that.”
“Jonathan is nowhere near dumb enough to voice ANY objections,” I declared, causing the girls to laugh. “But it’s Allyson’s room, and she has to have the final say.”
“Anything goes!” Allyson declared.
My spin landed on Sylvia who took off her jeans after we kissed, leaving her with just her bra and panties.
Shelly spun next, and Allyson was happy to kiss me and then remove her jeans. She was the last one to have them on, and now it was Sally, Shelly, and Lucy naked; Paula, Bianca, and me with just briefs or panties; and Allyson and Sylvia with bra and panties. I was very much at a point where I wanted the bottle to point to me, but Sylvia’s spin landed on Allyson again, which left only Sylvia with her chest covered.
Bianca’s spin landed on Sally who basically lept to the couch and spread her legs so I could pleasure her with my mouth. She moaned and used her hand to press my mouth firmly against her labia, but she hadn’t cum when time expired. She violated the rules slightly by giving me a soft French kiss before going back to her spot.
Sally spun and Paula excitedly climbed into my lap, but in keeping with doing my best to frustrate her, I only kissed her, and didn’t put a hand or my lips on her huge breasts.
“This is YOUR fault!” Paula declared when the minute was up, glaring at Lucy.
“Sucks to be you!” Lucy teased as Paula whipped off her panties.
She had a lot of pubic hair — much more than any girl I’d been with so far, and more than any of the other girls who were naked.
Paula spun and the bottle pointed to me, though that didn’t help her, because she couldn’t do what I was positive she wanted. Instead, she straddled me, we kissed, and I put my hands on her firm butt. Paula moved up and down rubbing her breasts on my chest and grinding against me, her soft pubic hair on my thighs and stomach as she moved. When her three minutes were up, she didn’t stop until Allyson reminded her about the rules Paula herself had made. After she moved, I stripped off my briefs allowing my erection to spring free.
“Oh! My! God!” Lucy exclaimed. “He’s HUGE! Like John Holmes huge!”
Paula laughed, “Not even close! Holmes is like twelve inches!”
“Who are you talking about?” Sally asked.
“A porn star,” Paula answered. “A friend of mine rented a pair of movies, and Holmes was in one of them — Insatiable. He basically shows up after the female lead, who is a nympho, has a threesome. He fucks her ass, and after he leaves, she begs for more.”
“He put a foot-long dick in her BUTT?” Sally gasped.
“Yeah. In an earlier scene, she’s deflowered by the gardener on her dad’s snooker table. That scene was actually really hot, though the lines were corny. But what do you expect from porn?”
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