Climbing the Ladder - Chutes and Ladders
Copyright© 2024 by Michael Loucks
Chapter 67: There's No Easy Way to Say This
Coming of Age Sex Story: Chapter 67: There's No Easy Way to Say This - 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
May 24, 1984, Chicago, Illinois
"Ungh! Ungh! Ungh!" Teri grunted as she humped forcefully in response to every thrust, her arms and legs wrapped tightly around me.
From the time Teri had answered my question by saying 'Fuck' until I'd been buried in her tight, slick tunnel, had been no more than five minutes, and she'd met my very first thrust energetically as our tongues tangled.
"UNNNNGGGHHH!" Teri groaned as her pussy spasmed hard, squeezing my dick tightly.
Teri spread her knees wider and moved her heels to my butt, allowing each thrust deeper inside her. When she had her next orgasm, I buried myself completely in her tight tunnel, and ground against her clit. The spasms of her pussy brought me over the edge, and I fired strong jets of cum into her.
Following the last spurt, I pulled out, moved so I could suck each of her bright red nipples, then kissed my way down to her mons, nuzzling my nose in her damp, red pubic hair. I moved down further and pressed my tongue into her, getting my first taste of her tangy juices.
"UNNNGGGGHHH!" Teri groaned when I flicked her clit with my tongue.
I savored the taste and feel of her pussy as I sucked and teased her clit until she squeezed her thighs to my face, raised her hips, and pressed down on the back of my head. I tongued her clit, prolonging her orgasm, and when it finally ended, I moved up, and we shared a fierce French kiss. When we broke the kiss, I moved off her and lay on my back next to her.
"That," Teri said, breathing heavily, "was an exhilarating first fuck!"
"Even more so without a rubber," I said. "When did you start taking the Pill?"
"In March, right after our last argument. Troy told me I was being an idiot, and I realized he was right, so I went to see my gynecologist. How will this work?"
"We see each other when you're home, you finish your degree, and we see where things are."
"Be honest, you're going to fuck other girls, right?"
"Yes. No commitments, and if you decide to date or have sex, that's your business, not mine."
"I'm not going to just fuck any guy who asks!"
"I didn't say you were, simply that what you do is your business."
"I think," she said, breathing more normally, "you can show me the paintings."
"In the morning," I said. "We have something more important to do now!"
"What's that?"
"I recall you saying that you would swallow!"
Teri laughed softly, "I did say that, didn't I?"
"Straddle my face, and I'll lick you while you do it."
"Pointers? I obviously haven't done it before."
"Treat it like an ice cream cone, then a popsicle, and use your hand to stroke me."
"I only had a brief glimpse, but I doubt I can get it all the way in my mouth."
"That's not necessary for it to feel good or to make me cum."
Teri moved, straddled my face, and rested her soft, red pubic hair on my chin. I felt her grasp me, and after the first tentative lick, I pushed my tongue between her plump labia. Teri quickly had me hard and continued to lick my glans and shaft while slowly stroking me.
I teased her clit with my tongue and brought her off, at which point she took my glans into her mouth and sucked gently. Teri's soft tongue swirled as she sucked and stroked, slowly bringing me towards a pleasurable release. Before that happened, though, I brought her off a second time, causing her to moan as she bobbed, sucked, and stroked me. The vibrations of the moan were enough to bring me over the top, and with a groan, cum spurted into her soft mouth.
She continued her ministrations, accepting each spurt and swallowing after the last one. She released me, I helped her turn, and she lay on top of me while she shared a sexy French kiss, sharing our combined flavors.
"You should be on top next time," I said.
"How long before you can go again?"
"Less than ten minutes and encouragement helps!"
"You just want your dick in my mouth again!"
"I won't deny enjoying that, but given the choice, I prefer to be in tight, wet pussy."
"As big as you are, at least compared to what they said in health class, I can't imagine you've ever been in one that wasn't tight!"
"You might have a point."
Teri kissed me, slid down, used her mouth to get me hard, then mounted me.
May 25, 1984, Chicago, Illinois
"Again?" Teri asked when I moved on top of her on Friday morning.
"Again!" I declared enthusiastically. "Unless you object."
"Never!" she exclaimed.
Twenty-five minutes later, after an energetic fuck followed by an orgasm for Teri from my tongue, I led her to the shower. We washed each other, dried off, and dressed.
"That was a nice way to finish," Teri said. "You were very gentle and loving when you washed me."
"I enjoy joint showers. Would you help me change the sheets on the bed? These need to be washed!"
"No doubt!" Teri declared.
We stripped off the soiled bedding and replaced it with fresh, and I gathered the soiled bedding to take to the washing machine.
"I'll leave the decision to you," I said. "But you're welcome every Thursday until you have to go back to school."
"And other times?"
"We have to play that by ear because I have class two nights a week plus Saturday mornings and other obligations. We can go out to dinner beforehand, if you want."
"I suspect that's the best I could expect, given everything you've said."
"Take one day at a time, and see where life brings you. I certainly didn't expect to be a widower and father at age twenty-one."
"I'm sorry for the way I handled things."
"There's no need to apologize. We each expressed our honest feelings, and we ended up right where we both wanted to be — in bed. Whatever else the future holds will have to remain to be discovered. Shall we go have breakfast?"
"Who'll be up?"
"Probably only Bianca, though Sofía's nanny will be here. Sometimes Deanna is up, sometimes not. CeCi is rarely up. Before I forget, how did you get here last night?"
"A cab."
"I'll call for a Town Car to take you home."
"Thanks. What about the paintings?"
We left the room and went to the gallery room, and I turned on the special lighting that had been installed.
"Those are really good," Teri observed. "And I made the right decision to wait to see them until after."
"Deanna is going to paint several more in this series," I said. "The next one will be when Sofía is three months old, then when she's six months, a year, and two years."
"That's actually pretty cool, and it's kind of like the bathtub pictures every parent takes. I thought she mainly painted abstract."
"That's her preference, but she has to paint in just about every style for her classes. If you were to come to my office, you could see six abstract paintings she's done for me — four with a financial market theme and two with Keiko as their inspiration."
"Your office is in this building, right?"
"Yes."
"Then next Thursday, I'll come to your office before we go out for dinner."
"Perfect."
I went back to the bedroom, gathered the sheets in my arms, and we went downstairs. I put the soiled bedding into the washer and asked Bianca to put them in the dryer before she came to work. She agreed, and I made the call for the car. The three of us sat down to eat breakfast, and when we finished, Teri and I left the condo. I made sure she was safely in the car, then headed to my office.
The morning routine was typical until around 9:30am when Bianca came into my office and shut the door.
"I was right!" Bianca smirked.
"Yes, yes, you're very smart!"
"Sorry, but I've been bursting to say it, and you won't be home tonight. What concessions did she request?"
"None. She expressly asked if I was going to have sex with other girls and didn't flinch when I said I would. She and I have a standing date on Thursdays when she's home. She, like Taya, has to finish her degree, which gives me plenty of time to sort things out."
"What are you going to do about Violet?"
"Not rush things. And she'll tell me what she needs but not ask me to do something that is beyond what I'm able to do."
"She's the one, isn't she?" Bianca asked.
"Probably," I admitted. "When the time is right, and I can love her the way she deserves to be loved."
"Passionately!" Bianca smirked.
"Yes, of course, but I meant figuring out how not to allow my love for Keiko to interfere with my love for Violet. I don't know how to do that yet."
"Time," Bianca counseled. "You'll figure it out. And Violet will know that you've figured it out, and that's when she'll ask you to make love to her. And that's how you'll know."
"I can't argue with that assessment."
"So, was she fun?"
"A fiery Irish girl?! What do you think?"
"Invite me on a Thursday night, and I can find out firsthand!"
"In your dreams!" I chuckled.
Bianca left the office, and I returned to work. As was typical for a Friday, Violet and I had lunch together, then went to the gym. After the gym, I worked until 5:00pm, then went to the condo to change before meeting Taya, Jack, Kristy, and the boys in the lobby.
"Everyone agrees on Indiana Jones and the Temple of Doom, right?" Kristy asked.
We all did, and then we all agreed on Star of Siam for dinner. The food was great, and the movie was excellent, though I thought Raiders of the Lost Ark had been better. After our usual stop at Oberweis, Taya and I bade the others farewell and went to the condo, where we went straight to my room.
"You know what I want!" Taya declared as we began undressing.
"One trip around the world coming right up!"
"And then conclude with slow and gentle, and sleep in each other's arms."
"I shall endeavor to please M'lady!"
May 26, 1984, Chicago, Illinois
On Saturday morning, after breakfast with Taya and Bianca, I headed to the School of the Art Institute for my modeling session with Britney. As I had said to Violet, the session started with a charcoal drawing and then oil-based paints. The session took a total of six hours, though we stopped for a twenty-minute lunch break.
"Are you sure I can't fuck you instead of paying you?" Britney asked at the end of the session. "I'd much rather fuck!"
I smiled, "Ask me again after the final session," I replied.
"OK," Britney agreed, reluctantly handing me two ten-dollar bills. "How does the afternoon of June 17th work? I'll have the clay figure roughly created from the photos, then finish 'live', so to speak."
"Is that a Sunday?"
"Yes. I figured it would be easier, given your class. We can still do 2:30pm or earlier if you want."
Saturday the 16th was the date with Bianca, Meg, and Nicole, so Sunday was perfect.
"That will work for me. 2:30pm is good."
"Great! See you then!"
I left the studio, and after checking my watch, I decided to stop in at Ateljé D and see Deanna. When I walked in, she was talking with a man in his forties who looked to me like a potential buyer. Deanna made eye contact to let me know she saw me, and I went through into the studio, where I saw Kendra in a paint-covered smock standing at an easel.
"Hi!" she exclaimed,
"Hi! What are you working on?"
"Come see," she said.
I walked around and looked at the canvas to see a painting of the Chicago skyline, along with a photograph from which she was working.
"I need to use the photo because I can't afford to rent a boat or helicopter to do this outdoors!"
"How would you paint in a helicopter?"
"Carefully!" she declared. "It would have to be one of those big ones they used in Viet Nam to transport stuff, obviously."
"Class assignment?"
"Yes. I'm also going to paint New York City and LA, again, from photos because I can't afford to travel there."
"I like this," I said. "It would be perfect for the wall next to the door to the Japanese room."
"Could I interest you in all three?" she asked. "They're a series."
"I'd probably have to display two of them in the gallery, given the limited wall space, but that could work. When you finish, let's talk price."
"$750 for all three, if we have a private hanging party!" she said, licking her lips.
"That might be possible," I replied with a smile. "Let's talk at the end of the Summer when you finish?"
"Awesome!" Kendra declared.
"He is, isn't he?" Deanna asked, coming into the studio.
We hugged and exchanged a quick kiss.
"Prospective buyer?" I asked.
"Yes. He's very interested in Stacey's painting and sculpture. I expect he'll be back to buy them."
"Jonathan wants to buy my cityscapes!" Kendra declared.
"I was thinking of hanging the Chicago skyline on the wall just past the door to the Japanese room as you come in, so opposite the kitchen."
"That's perfect," Deanna said, "but what about the other two she plans?"
"The gallery, I think."
"You're going to fill that room pretty quickly!"
"True, but that's a good problem to have. And I can display some in my office, too — there's room for at least three or four more, and the Research Department walls have space for at least eight."
"You could rotate those and the ones at home, if you wanted. Obviously, you'll have some favorites that will stay up all the time, but others you could cycle."
"That sounds like a good plan. Anyway, I don't want to disturb you further, so I'm going to head home."
"We're already seriously disturbed!" Kendra declared. "We're artists!"
Deanna and I both laughed, I hugged Deanna, then left Ateljé D to head home. When I walked in, I found Bianca sitting with Esme, Jasmine, and another girl I didn't know. I grabbed a beer from the fridge and went to sit with them on the sectional sofa.
"Jonathan, this is my friend Debbie," Jasmine said. "Debbie, Jonathan."
"Nice to meet you," I said. "Bianca, are they staying for dinner?"
"We were going to order Chinese. If you don't have anything to do, you could join us."
"Sounds good," I agreed.
I heard a squeak, then a cry over the intercom, and got up to go upstairs to get Sofía. I changed her obviously dirty diaper, then carried her downstairs and handed her to Bianca to nurse her.
"Your condo is amazing!" Jasmine declared.
"Thanks. How is school going?"
"Good grades and a good time without getting into too much trouble!"
"UCLA, pre-med, right?"
"Yes! Could I talk to you privately for a sec?"
I nodded, and we went to the Japanese room.
"What's up?" I asked.
"If it's not too soon, and you don't have plans, I'd like to spend the night," she said.
"I'd like that," I said.
"Me, too, obviously! If you're interested, Debbie could use some personal attention before dinner. I'm pretty sure Esme or I mentioned her to you last year."
"I'm sure that you or she did, but I don't remember."
"A lot happened since then, so I'm not surprised. She just graduated and is going to UCLA in the fall, also pre-med."
"Does she know you're asking?"
"No," Jasmine replied. "I mean, she knows I know she's interested because she told me she was when I described what it was like being with you. After she saw you today, she whispered in my ear she'd be in your bed in a flash if you asked."
"I'm actually being a bit more cautious," I said. "Not like before."
"It's cool. I just thought I'd let you know. It's obviously up to you, and I'm staying either way!"
"You're still on the Pill, right?"
"Absolutely!"
We left the Japanese room and returned to the conversation pit, where I sat next to Bianca, who was still nursing Sofía.
"I'm staying, Esme," Jasmine declared.
"No surprise!" Esme replied.
"Esme, where's Katy today?" I asked.
"Disney World with her family. They'll be back on Sunday. If you're interested, we could get together after she comes home."
"Call once she's home, and we'll find a time to get together."
"We will!"
"Can, uhm, anyone ask?" Debbie inquired hesitantly.
"Anyone can ask," Bianca interjected before I could respond.
And with that, my plan to simply let it be went right out the window or would have, if the windows opened. I could always say 'no', of course, but Debbie was cute, with large, firm breasts that were outlined by her tight polo, along with long legs, full lips, long brown hair pulled back in a ponytail, and gorgeous brown eyes.
"Go for it!" Esme urged.
Debbie got up, came over, and plopped in my lap.
She put her lips close to my ear and whispered, "Esme and Jasmine say you're the best. I want to."
"Can we wait fifteen minutes so I can hold my daughter after she finishes eating?"
"Of course!" Debbie said happily.
"Deb, come talk to us for a sec," Jasmine said.
She, Esme, and Debbie got up and moved to the other end of the open living area, past the dining room table.
"Sorry," Bianca said.
"For what?" I asked.
"I showed them the gallery, forgetting about Nuclear Family. Debbie's eyes bugged out, and I swear I thought she was going to start drooling."
"I believe Jasmine did a sufficient marketing job last year that the painting was only icing on the cake, so to speak. What's with the convo?"
"I'm pretty sure she has very little experience and might even be a virgin, so the 'pros' are giving her pointers!"
"Sanity check here; am I doing the right thing?"
Bianca laughed softly, "You're asking a Mexican chick about your sanity? If so, that proves that you are nuts!"
I laughed, "Neither you nor Esme seems crazy to me.
"Because we're all crazy together! But in all seriousness, what's bugging you? I know it's not morality, and it's not unethical."
"I'm not sure, actually. I turned down Claire and Britney because something felt off in those cases. You know what happened with Teri, obviously, and then today, Kendra propositioned me when I stopped in at Ateljé D and expressed interest in buying a painting she's working on of the Chicago skyline. And then there's the ... satisfaction, I guess, I've had from my dates with Nikki, Kayleigh, and Krissy, where sex isn't even on the table."