Climbing the Ladder - Chutes and Ladders
Copyright© 2024 by Michael Loucks
Chapter 45: An Apology
Coming of Age Sex Story: Chapter 45: An Apology - The world of finance is, in its simplest form, just like a game of Chutes and Ladders. There are only two things that matter to the bottom line: profits and losses. The goal is to climb to the finish and thrive, not fall back down the chute. Having been named the manager of the newly created Research Department at Spurgeon, Jonathan's career is soaring. However, as tends to happen, profit is balanced by loss. The next rung of the ladder will be much harder to reach, but he continues to climb.
Caution: This Coming of Age Sex Story contains strong sexual content, including Ma/Fa Tear Jerker Workplace
March 10, 1984, Chicago, Illinois
Had Stefi come to me on Monday night and said what she'd just said, I'd have been seriously concerned, but it was five days later, and we were sitting in a restaurant fully clothed. Two things gave me pause — birth control and her regular church attendance. The first one was easily remedied, as there was an Osco on the way back to Stefi's dorm. As for church, that wasn't my problem, so long as I clearly communicated my position.
While those things gave me pause, the larger issues were whether I wanted to be with her and if I was ready to be with someone new. It really was a question of 'when', not 'if' at this point, and the ultimate question became whether or not I was ready to fulfill her fantasy. There was no question of attraction, as she had long, dark hair, brown eyes, and a nice body, not to mention an obvious desire to be with me. Whom was I kidding? Of course I wanted her.
And that brought me back to 'should I' and 'should she'. I was positive that, at some point, there was going to be a first new girl, if not today, then potentially Alexa, or, I thought, Violet if she could accept my situation. And that was really the question for Stefi. The correct course of action was to lay it out and let her decide if she could accept that.
"If we do what you're suggesting, I can't make any promises beyond doing my best to fulfill your fantasy, and I need to say upfront that going to church isn't on my agenda and isn't likely to be."
"I don't care! Thinking about it is driving me crazy!"
I had one last chance to be sure I was ready for this, and I felt I was.
"If you're sure," I said, "finish your dessert, and we can skip the movie and go to your dorm room."
"Oh, God, yes!" Stefi moaned.
I wondered now if *I* could handle her rather than the other way around! The pent-up sexual energy that was going to be released might move seismographs in California. We both quickly finished our dessert, and after I paid the check, we left the restaurant. The only fly in the ointment was that I'd used the valet service, which meant retrieving my car, finding a place to park to go to Osco, and then parking in a garage a short walk from the school.
Stefi fidgeted while we waited for the valet to bring the car and almost leapt in when the valet held the door for her. I went around to the driver's side and got in, and once the doors were closed, I drove away.
"I need to stop at Osco," I said. "I wasn't prepared."
Stefi laughed softly, "I'm on the Pill to regulate my period. My mom had kittens when my doctor prescribed it when I was sixteen, and she didn't want to fill the prescription. My aunt finally talked her into it, but I wasn't ever allowed to be alone with a guy after that."
"I don't agree with your parents on that, but given my mom got pregnant with me when she was sixteen, I at least understand your mom's point."
"It was dumb because I had never really thought about doing it until last Monday. Then, all of a sudden, I HAD to do it!"
I pulled into a parking garage a few blocks from Stefi's dorm, and after parking, we walked quickly to the exit, then the two blocks to the building. Stefi let us in with her keys and signed me in. She led me to the elevator, which we took to the fourth floor. When we stepped out, I followed her down the hall to her room, which was a single. She opened the door to let us in, then closed and locked it behind us. She turned on the overhead light, and we took off our coats and shoes.
"I want to see it," she said, her voice dripping with desire.
I nodded and removed my rugby shirt, T-shirt, jeans, socks, and briefs. Knowing what she wanted, I was already rising to the occasion.
"Oh, God!" Stefi moaned. "Can I touch it? Please?"
"Whatever you want," I agreed.
Stefi moved to where I was standing, and I felt her hand on my rapidly hardening shaft. She squeezed gently, then traced her fingers upwards to my glans. She wrapped her hand around it and squeezed softly.
"Oh," she cooed. "So hard and so soft."
She surprised me by dropping to her knees and pressing my glans against her cheek. She moved her other hand to cup my sack and lifted just enough to weigh my balls.
"So cool!" she exclaimed breathlessly.
Stefi spent several minutes exploring, including stroking me, cupping my sack, squeezing gently, rubbing my glans on her cheek, and examining me closely.
"I want to kiss it," she whispered, looking up.
I nodded, and she planted a quick kiss on the tip, then another, and a third. She began kissing down along my shaft, and when she reached the base, she kissed each side of my sack before kissing back up to my glans. She kissed it again, though, with her mouth slightly open so that her tongue touched the slit. She repeated what she'd done before, but this time, her tongue traced along my shaft.
When she completed that cycle, she grasped my shaft and held my glans to her cheek while fondling my sack. After a minute, she moved back a bit and planted a sloppy, wet kiss on my glans. This time, she swirled her tongue around and around, then opened her mouth wide, moved forward, and closed her lips around the base of my glans.
Stefi moaned softly, then began sucking gently and running her tongue over my glans, causing me to twitch and groan in pleasure. After a minute, it dawned on me that she knew what she wanted to do but had no real idea how to do it.
"Stroke me while you bob your head up and down, so your lips move along my shaft," I instructed. "And slide your tongue around."
Stefi moaned again, and I felt her soft hand grasp me and begin stroking. She began moving her head so that her tongue and lips slid over my glans and along my shaft. The pleasure was exquisite, and the desire burning inside her made up for inexperience. My pleasure built slowly but then became overwhelming, and I knew I was close.
"Stefi," I said. "You know what's going to happen, right?"
She released me, looked up, smiled, then quickly took me into her mouth. She stroked rapidly, sucked vigorously, swirled her tongue faster, and squeezed my sack slightly harder. Thirty seconds later, I twitched twice, groaned, and the first spurt of cum splashed into Stefi's mouth. She moaned and redoubled her efforts, coaxing spurt after spurt, hungrily swallowing my cum.
She kept up her ministrations for about five minutes after I'd cum, and the pleasure was intense, as I was extremely sensitive after an orgasm. She finally released me, then planted numerous kisses all over my dick.
"So cool," she breathed, then stood up. "I need it in me!"
She stepped back and quickly shed her clothes. My erection showed no signs of subsiding, so I maneuvered Stefi to the bed.
"I want to see it go in," she whispered urgently.
Instead of having her lie down, I moved the pillows and had her sit on the edge of the bed with the pillows behind her. I helped her into a reclining position, resting on the pillows and supporting herself with her elbows, then moved between her legs. Just below her dark pubic hair, I saw labia slick with juices, and I was positive she was ready.
I grasped my shaft and rubbed my glans along Stefi's labia while she watched wide-eyed. When I was coated with her copious juices, I moved to the correct spot and slowly pressed forward, spreading her labia.
"Oh!" she gasped as I entered her. "Oh!"
She was dripping wet, so I simply continued sliding into her and had no trouble pushing all the way in.
"Oh! OH! OH!"
I slowly pulled back, and Stefi watched intently as I began fucking her with long, slow strokes. I felt her squeeze her muscles, which intensified my pleasure, but I'd cum recently, so there was no way I wasn't going to last a long time despite the exquisite feel of her tight, slick tunnel.
After about two dozen strokes, I pulled out completely and moved onto the bed. I lay on my back and had Stefi straddle me. I helped her mount me, and she moaned loudly as she slid down my shaft. At that point, nature took over, and she began moving up and down and back and forth, grinding against me.
Just over a minute later, she tensed, held her breath, squeezed her muscles, and ground hard against me. Her breath exploded from her mouth, her body shook, and she groaned deeply as her pussy spasmed hard around my rock-hard shaft. That orgasm unleashed her, and she began moving more wildly, bringing herself off several more times before I blasted cum deep inside her, setting off a tremendous orgasm, the strong spasms of her pussy milking cum from me and causing my head to spin in ecstasy.
When both our orgasms passed, Stefi stretched out on top of me and put her head on my chest, panting hard. I was breathing heavily as well, despite Stefi being the one who had exerted herself. Over the next five minutes, our breathing returned to normal, and I softened and slipped from her.
It dawned on me we hadn't kissed, even once, despite her giving a blowjob and fucking. I decided there was one more thing to do before our first kiss, so I gently moved Stefi onto her back, moved down, got between her legs, and kissed the insides of her thighs. I planted kisses along her labia, then pushed my tongue in and teased her clit. I slipped my arms under her legs, lifted them, moved my hands to her firm breasts, and strummed her nipples as I closed my mouth around her clit.
"UNGH!" she grunted, "UNG! UNGH! UNGH!"
She began flexing her hips and, a minute later, had a strong orgasm. That one was followed by two more over the course of ten minutes before I moved up beside her.
"I want to suck you again," she breathed.
Not being an idiot, I didn't object, so she slid down and rested her head on my stomach. She explored with her hands, lips, and tongue, and when I was hard, she began bobbing, sucking, licking, and stroking, all the while cupping my sack. I'd cum twice, so I knew she'd have to work harder.
After a few minutes, I put my hands on her hips and encouraged her to straddle my face. She did so and moaned deeply around my shaft when I flicked her clit with my tongue. Our sixty-nine lasted for nearly fifteen minutes before I had my release, which was a perfect reward for the four orgasms I'd given her with my tongue.
When she finally released me, she moved off me but didn't turn, instead resting her head on my stomach and running her fingernails along my shaft. She played with me for about ten minutes before blood began flowing again, and she moved on top of me to sixty-nine again.
This time, though, once I was hard, I encouraged her to move off me. After a bit of maneuvering, she was on her back, I was between her legs, and plunged into her slick tunnel. I began fucking her with strong strokes, and after about a dozen, she wrapped her legs around me and began humping wildly. We fucked hard for fifteen minutes, with Stefi moaning, groaning, and gasping for breath as she had four good orgasms before I pushed as deeply into her as possible and came hard.
When my orgasm had passed, I raised my head and pressed my mouth to Stefi's mouth. She parted her lips, and our tongues tangled in our first kiss. We kissed until I softened and slipped from her, at which point I rolled off her and lay on my back next to her in her twin bed.
"Unreal," she breathed. "Way better than my dream!"
"It was fantastic," I said.
"Can you just keep doing it for as long as we want?"
"No," I replied. "Physiology being what it is, three, possibly four more times, with longer in between each time, before I need to sleep to recover."
"The rules say you can't sleep over," she said. "But I want to suck you twice while you lick me, then have you on top and go hard like we just did."
"I'm more than happy to oblige."
Two and a half hours later, we got out of bed, and I borrowed a towel from her so I could walk down to the guys' showers. She put on a robe and went to the girls' showers, and when we were both clean, we met back in the room to dress.
"I was surprised you didn't start with kissing," I observed.
Stefi laughed softly, "I wanted it in my mouth so bad that I didn't want to waste time!"
"Was that your first ever kiss?"
"Yes!" she declared mirthfully. "And it was after I sucked you, we screwed, and you licked me!"
"Are you going to church in the morning?" I asked.
"I don't think I can after what we just did! That's not exactly OK in their eyes."
"And yours?"
"If I didn't want to do it, I wouldn't have. I wanted to! I know you said no promises, and I accepted that, but if you want, you could come over next Saturday. I could touch and kiss and lick and suck your gorgeous thing all afternoon and evening until midnight curfew!"
"Tempting," I chuckled.
"We can do anything else you want, too! But if not, I totally understand."
"OK to let you know on Wednesday or Thursday?"
"Yes! I need to walk you down and sign you out."
"OK."
She came over to me and put her arms around me. I hugged her back, and we exchanged a soft French kiss.
"You fulfilled my fantasy," she said dreamily. "Thank you."
"It was my pleasure! Literally!"
We kissed again, and she escorted me to the lobby, where she signed me out. I said 'good night', then left the building and walked to the parking garage, where I retrieved my car. I drove home, and when I went into the house, it was dark, but I saw light coming from Deanna's studio, so I pulled down the stairs, climbed partway up, and saw her staring at a partially finished abstract painting with her brush on her chin.
"Mind if I come in?" I asked.
"No! Come on!"
I climbed the stairs, then pulled them shut, and Deanna put down her brush and took off her smock. We sat down, side-by-side, in two bean bag chairs.
"So?" she asked with a smirk.
"I normally don't talk about what I do or don't do with girls except with them or witnesses, but after our conversations the past two weeks, I'm going to make a permanent exception for you."
Deanna smiled, "I appreciate that."
"The shortest way to say it is that if you and CeCi are interested in a threesome, I'm game."
"Wow! That's a change!"
"You're going to be inclined to disbelieve what I tell you, but it's completely true. Monday was the first time Stefi had ever seen a grown man naked, and her imagination and libido ran away with her."
"You're serious?"
"As a heart attack! She said once she saw it, she started obsessing and dreaming, and during dessert, she told me she gave me her number because she wanted to do all the stuff she imagined. Needless to say, we didn't make it to the movie. Instead, we went back to her dorm, where she fulfilled her fantasy – she had me strip, explored my dick and balls, gave me a blowjob, had me take her virginity while she watched, rode me, engaged in sixty-nine, and had me fuck her before we exchanged our first kiss, which was her first one ever."
"No way!" Deanna exclaimed. "Seriously?"
"Seriously. After that, sixty-nine twice, and then we fucked like crazed bunny rabbits. We showered and dressed, then she signed me out, but only after asking me to visit next Saturday so she can suck me from mid-afternoon to midnight."
"That's just crazy enough to be true and puts the letters in Penthouse to shame!"
"Letters?"
"Guys write in with their stories, which are usually obviously exaggerated. Yours would be over-the-top! What changed?"
"Remember I was in the 'if' stage? Tonight, it was the 'when' stage, at least with regard to being with a new girl. I knew I'd eventually do it, so why not with a girl who clearly was dying to have uninhibited sex with me?"
"I suppose that does make sense. Are you OK?"
"Yes. I suggested we go back to her dorm because I'm still not ready to invite someone into Keiko's and my bed. I'm absolutely going to wait until the new bed is in the condo for that. One other interesting point — Stefi was a regular churchgoer. Until tonight, that is."
"Huh?"
"She went to a Baptist church in Oklahoma and to Moody Church here. She said after tonight, she can't go back."
"Uh-oh."
"Uh-oh?"
"Jonathan, you clearly didn't use rubbers..."
"She went on the Pill at sixteen to regulate her period. She said her mom freaked out when the doctor prescribed it and refused to fill the prescription until her aunt intervened. From that point on, Stefi wasn't allowed to be alone with a boy."
Deana laughed, "And then they let her come to Chicago to attend a school that is a complete den of iniquity! And one thing is for sure – you and I are going to fuck each other senseless very soon! Well, assuming you're OK with that."
"I don't think I'm back to 'normal', but I'm not sure I can ever go back to the old normal. It's finding the 'new normal' as you suggested."
"I'm happy to see you in ... let's call it a more normal state. I spent some time with Tasha this afternoon and showed her the budget. We're going to start looking at furniture. Given today's developments, we're going to furnish your room first so that you have a love nest to use for the next few months."
I chuckled. "I appreciate the thought. I'm not planning to go crazy."
"No, but crazy always seems to find you!"
March 11, 1984, Chicago, Illinois
When I woke up on Sunday, I got out of bed, emptied my bladder, shaved, showered, and dressed, then went downstairs to have breakfast. I ate with Jack and Kristy, then spent time in the Japanese room reading the Trib, Crain's, The Economist, and the Wall Street Journal. At various times, Bianca, Juliette, and CeCi sat with me and read. Jack and Kristy went out for the day, and everyone else had eaten lunch together.
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