Climbing the Ladder 5 - Reaching New Heights
Copyright© 2026 by Michael Loucks
Chapter 16: Mind If I Cut In?
Fiction Sex Story: Chapter 16: Mind If I Cut In? - Jonathan's business life is booming, but he's also suffering from yet another loss. While he's done his best to pick up the pieces of that sundered relationship, he can't help but feel responsible. However, where two close relationships have withered, another blooms. Violet has transitioned from a badly damaged girl to a vibrant woman. Will he continue to climb this ladder, or will there be another ladder to climb in his future? No matter what, the only direction he plans to go is up.
Caution: This Fiction Sex Story contains strong sexual content, including Ma/Fa Workplace
June 30, 1984, Chicagoland, Illinois
Friday had been a normal day at work, and at the end of the day, I'd met Jack, Kristy, Costas, Trevor, Rick, and Taya. Dustin and Archie hadn't joined us because they were out in the burbs for a wedding rehearsal Dustin was shooting. We'd had a nice dinner, then went to see Gremlins, which was a fun movie starring Phoebe Cates.
As usual, Taya had come home with me, and when we'd walked in, I'd seen a letter from the clinic. I'd checked it and had seen it was completely clear. I'd carried it with me when Taya and I had gone upstairs, and had put it in my desk. Taya and I had fooled around for several hours before falling asleep, and she'd left the condo when I left to drive to Violet's house for breakfast.
After breakfast, I went to class, then headed home. The first thing I noticed was a beautiful grey cat stretched out on the floor.
"Misty, I presume?" I asked.
"Yes," Deanna replied. "I put her food and water dishes and her litter box just outside the laundry room. They're out of the way, and I'll change the litter in the box every day so the condo doesn't smell. I also put one of those stick-up air fresheners just above it, but out of her reach. And, of course, the air purifiers will help, too. There's also a cat tree — it allows her to climb up onto platforms, which cats like to do."
"That sounds fine. Anything special I need to know?"
"Just watch out because cats like to get underfoot."
"So, like toddlers, then? At least from what I hear!"
Bianca, who was sitting with Nicole, laughed, "We'll find out soon enough!"
Nicole and Bianca seemed very close to being a couple, and I didn't think it would be long before Nicole moved in. I felt that was a good thing, but it would change the dynamic in the condo.
I left the condo at 3:00pm to drive to the cookout in Oak Brook Terrace. The house was huge, as was typical for the newly built area of the town, and there were at least a dozen expensive cars parked in the long, circular drive.
"Hi!" Missy exclaimed, seeing me.
She was wearing a bikini top and shorts and had a decent tan, which likely meant sexy tan lines, something I thought was very attractive.
"Hi," I replied.
She gave me a quick kiss on the cheek, then took my hand and led me around the house to the expansive backyard. The yard had a large above-ground pool, a hot tub that looked as if it would seat eight, and a half basketball court. A brick grill completed the yard, and a bar, manned by a bartender, was in the shade of an awning near the house.
"What does your friend's dad do?"
"He's an injury law attorney for a big Chicago firm."
An ambulance chaser, the lowest of the lowest scum. I absolutely believed that people who were injured through no fault of their own ought to be compensated, but so-called plaintiff's attorneys made a business of extorting settlements from companies that had deep pockets, and even the threat of a lawsuit could move the market against a stock. I could, in theory, take advantage of such situations, but the more likely case was that it would damage a position I'd taken, as I was mostly long the market.
"Let me introduce you to people," she continued.
She introduced me to about a dozen people who were there, including the host, Mark Stroud, who was my age and attended Harvard and was, unsurprisingly, given his dad's profession, pre-law.
"Jump in the pool or the hot tub at any time," Mark offered. "Beer and pop are at the bar, or Max will mix you a drink. Snacks are in the gazebo. We'll fire up the grill in about an hour."
"Thanks," I said.
Missy and I went to get a beer from the bartender, then stood in the shade sipping from our cups. More people were arriving every few minutes, and soon, there were about fifty people in the backyard, with about a dozen in the pool. Missy suggested we get in the pool, so I went into the house and used the bathroom to change into my suit. When I came out, Missy had ditched her shorts, revealing her bikini bottoms and a cute butt.
We got into the pool with six other couples, with all of the girls wearing bikinis and most of them having nice tans. I was the pastiest white of everyone because I didn't spend much time outside, given everything going on in my life. That meant I'd need to be careful not to burn, but it was late enough in the day that the sun wasn't as strong as it would have been at mid-day.
I hadn't used the pool in the Hancock Center and made a mental note that I should do that and perhaps host a party on the concierge floor. That was something I'd have to check into, but at the moment, I was much more interested in checking out all the female flesh on display. I was in pretty good shape, but most of the other guys had tans and were muscular, while I worked out for tone, not muscle bulk. There were plenty of nerdy or skinny guys, but none of them were in the pool.
We had been in the pool for about fifteen minutes when one of the guys invited me to play three-on-three basketball, but I'd begged off, as the only time I'd ever handled a basketball was in gym class during my Sophomore year of High School. When they started playing, the correctness of my decision was confirmed, as the guys playing were all really good.
We got out of the pool and got fresh beers, and not long after, the first burgers and dogs came off the grill. Missy and I helped ourselves to some food, then sat with four of her friends — Mike, Jim, Trisha, and Cindy. All four of them were starting college in late August — the two girls at Northwestern and the two guys at UofC. All four of them seemed nice enough, but their perspective was so much more like High School students than mine that they'd have to grow up quite a bit before I'd want to hang out with them. That said, if they followed the usual pattern, a year of college would make all the difference in the world.
We'd just finished eating when I saw something I simply couldn't tolerate.
"We need to leave," I said urgently to Missy.
"What?! Why?" she asked.
"The guys over there are doing lines of coke," I said, nodding in their direction just enough to indicate where she should look.
"Uhm, I thought everyone at Spurgeon did coke."
"Not me," I replied. "And friends with the Police Chief or not, I'm not staying."
"Uhm, er, my friends will be upset if I leave."
"If you want to stay, that's up to you, but I'm going to get dressed and go."
She thought for a moment before responding.
"If you want, we could hang out at my house for a bit. We have a pool, and my parents aren't home to bother us. And you know my dad doesn't have a problem with you."
"That's fine," I replied. "Let me get dressed, and I'll meet you out front."
"I need to let Trisha and Cindy know, and I'll grab my clothes."
Five minutes later, we were in the Strouds' driveway.
"I don't have a car here," Missy said. "I rode with Trisha and Cindy."
We walked to my car, I helped her in, and quickly drove out of the driveway, following her directions to her house.
"I'm really sorry," she said. "If I knew you were so opposed to drugs, I would have warned you."
"If you had, then I wouldn't have come. I'm not judging; they can do whatever they want, and it's cool. I just don't want to be around it."
"How do you deal with it at work?"
"The Research Department has its own offices. Also, I've never seen it openly displayed at Spurgeon, even if I'm positive guys are doing lines during the day."
Just over five minutes after we left the party, we drove up to Missy's house, which was exactly what I'd expect for someone who was a senior trader at Spurgeon — huge, on a large lot, with expensive landscaping, and a multi-car garage. I parked in the driveway where Missy indicated I should, and she led me into the house, disarming the alarm after we entered. She gave me a quick tour, confirming the house was as opulent on the inside as I assumed it would be, then led me out to the backyard, where they had an above-ground pool.
"Have you ever skinny-dipped?" she asked.
"No."
"Want to?" she asked invitingly.
I wanted to see Missy's tan lines, and skinny-dipping was a perfect way to do it without complications, though I had a sneaking suspicion we'd end up fooling around, assuming I was reading her intentions correctly.
"When will your parents be home?" I asked,
"Not for at least another four hours."
"I'm game," I said with a smile.
"Cool!" she exclaimed happily.
Without waiting, she untied her bikini top and let it fall to the ground, then slid off her bottoms. She was about six inches shorter than me, with brown hair, nice breasts, a perfect V of pubic hair, and powerful legs. As I'd hoped, the places the bikini covered were almost white, while the rest of her body had a golden-brown tan. The contrast was stunning and threatened a display that wasn't appropriate, at least at the moment.
I quickly removed my trunks, and Missy's eyes went wide.
"Well, uhm, wow," she stammered.
"I could say the same about you," I replied with a smile.
She returned the smile, then turned to climb the steps to the pool. I followed her, taking note of her firm, sexy butt. I realized that on the pool deck, it would be possible for someone to see us, but given the number of trees along the fence, they would have to make a concerted effort. Once we were in the pool, though, we were out of possible view.
"I really am sorry about the cocaine," Missy said.
"Apology accepted," I replied. "I'm curious, but have you used coke?"
"No. I've smoked pot, but never done anything harder. You?"
"Nothing; not even pot."
"Would it have bothered you the same way if they were smoking pot?"
"I wouldn't want to be around it," I replied. "It's just not worth the risk. There are plenty of other things to do that are fun and feel good that aren't illegal."
Missy moved right up to me so that the nipples on her large, firm breasts just barely touched my chest.
"Wanna fool around?" she asked, hopefully. "It's fun, and I'm sure it'll feel good! I'm on the Pill."
I nodded and pulled her body against mine, and we exchanged a soft kiss.
"Get up on the deck, and I'll get you hard," she offered.
I raised myself and sat on the deck, with my feet dangling in the pool. Missy moved between my legs, grasped my shaft, and took my glans into her mouth. She sucked and swirled her tongue, and as I began to harden, she started bobbing and stroking. It didn't take long before I was fully erect, and when I was, she released me and moved back a bit. I slid into the water, and she put her hands on my shoulders. I put mine under her firm butt cheeks and lifted her up. She wrapped her legs loosely around my waist, then reached down and grasped my shaft. She positioned it, then I lowered her onto it.
"Fuuuuucckkkk!" she groaned as she slid down my shaft, enveloping me in her very tight tunnel.
She wrapped her legs tightly around me and began grinding. In order to get some leverage, I backed her against the wall of the pool and began thrusting in and out of her silky tunnel. As we continued fucking, our lips came together, and our tongues tangled. The position wasn't the most comfortable, and I couldn't get much leverage, but I'd never screwed in a pool before, so I was determined to make it work. And work it did as Missy had her first orgasm a few minutes later.
"Fuuuuuccccckkkkk!" Missy groaned as her pussy spasmed around my shaft. "So full and so deep!"
I got her there twice more before I had my release, pumping cum deep inside her spasming pussy. Given the awkwardness of the position, once I'd cum, I carefully lifted Missy off me and set her down. She put her arms around my neck and pressed her body against me, resting her head on my chest.
"Huge and with awesome stamina!" she declared. "Wanna go again?"
"Tight and sexy!" I replied. "I do, though the pool is a little awkward."
"The lounge chairs are comfy and sturdy!"
We got out of the pool, and Missy led me to a cushioned chaise, where she had me lie on my back. She knelt beside the chair, grasped my shaft, and once again took me into her mouth. She got me hard, but this time, she continued bobbing, testing how far she could take me into her mouth. She couldn't quite manage, and after a few minutes, she released me, stood up, and straddled the chair. She grasped my dick, held it straight up, and lowered herself onto me once again.
"Jesus," she gasped when our pubic hair meshed.
She put her hands on my chest and began grinding against me, and a few minutes later, she started moving up and down and back and forth. I cupped her full breasts in my hands and strummed her nipples with my thumbs, and she quickly leaned forward so I could take her nipple in my mouth. I flicked it with my tongue, and she immediately had a strong orgasm.
"Fuuuuuccccccckkkkkkk!" she groaned.
Missy's nipples were very sensitive, and they helped her have three more orgasms before I had mine. When they both passed, she stretched out on top of me, and I cupped her sexy butt.
"WAY better than Homecoming or Prom!" she panted. "WAAAAY better!"
"You have a very tight pussy!" I declared.
"Because you're so big!" she panted.
We lay quietly while her breathing recovered.
"I've only seen two ready for action before today, and you are HUGE compared to both of them. And neither of them went for more than four or five minutes! I suppose it's the difference between a man and a High School boy."
Actually, it wasn't, at least as far as I could tell, because I'd been able to go just as long with Bev when I was seventeen.
"I do my best," I replied.
"I want to go again when you're ready!" Missy exclaimed.
Before I could answer, I heard a female voice.
"And just what's going on here?!" it asked.
"Nothing!" Missy tittered. "Nothing at all!"
"It doesn't look like nothing!" her friend Trisha exclaimed. "Now I know why you ditched the party!"
"It really was that Jonathan objected to the coke!" Missy protested.
"Uh-huh! Did it take you five minutes to start boffing once you got here?"
Missy laughed, "I suggested skinny-dipping as soon as we got here!"
"So, three minutes after you got here!" Trisha smirked. "How was it?"
"OH! MY! GOD!" Missy exclaimed. "He's hung like a horse and can go for twenty minutes! I came SO hard!"
"Mind if I cut in?" Trisha asked with a sly smile. "Or is he yours?"
"He's not mine; we're just casual friends," Missy said. "And it's not up to me; you'll have to ask him!"
Trisha smiled, pulled off her shorts and T-shirt, then removed her bikini. She was blonde, just a bit shorter than me, and had long legs, small breasts, and well-defined tan lines.
"What do you think?" Trisha asked, striking a pose.
"Very sexy," I replied, taking in how her creamy-white skin contrasted wonderfully with the golden-brown tan.
Missy got up, and Trisha walked over to the chaise.
"I'm on the Pill," she said. "How about it?"
She was a college Freshman, or would be, in a month. She was sexy, available, and on the Pill. If it was going to, as Murray Matheson had said, continue to rain pussy, I was going to take advantage of it. It was clearly casual sex, or 'just fucking' as Violet and other girls had called it, confirmed by Missy's 'casual friends' comment.
"Only a complete fool would say 'no'," I said, "and I'm not a complete fool!"
"You should probably take a dip in the pool!" Trisha suggested.
I chuckled, nodded, and got up. I walked over to the pool, climbed the steps to the deck, and jumped into the pool. I moved around a bit to wash off the traces of Missy, then got out and went back to the chaise. I sat down, and when Trisha came to sit in my lap, I maneuvered us into a sixty-nine position.
"Oh, sure, SHE gets eaten!" Missy groused.
"You had a chance and chose not to!" I chuckled.
I gently pulled Trisha's vulva to my lips and pressed my tongue into her. She moaned softly, grasped my flaccid shaft, and began kissing my glans. I began alternating between pressing my tongue into her, teasing her clit with my tongue, and sucking gently on it. Trisha took me into her soft mouth and sucked gently while running her fingers lightly along my shaft.
As I began to harden, Trisha began bobbing slowly, moaning around my shaft as I pleasured her. When I was fully erect, she made a valiant attempt to deep throat me, but choked and coughed and didn't try again. Trisha had a small orgasm, and I gently encouraged her to release me and turn so she could straddle me. She grasped my shaft and rubbed my glans along her thin labia, then slowly impaled herself on me.
"Holy God!" she gasped, then panted and groaned as she sank down until I was fully embedded in her extremely tight tunnel. "Jesus," she said, blowing out a long breath.
She sat still for a minute, panting, then lifted up and sank down again, groaning as her pubic hair meshed with mine. She raised and lowered herself several times, then began grinding and moving back and forth.
"Unreal!" she panted.
"Want me to fuck you?" I asked.
"God, yes!" Trisha gasped.
She lifted off and moved to the side. I got up, helped her lie on the chaise, then got between her legs. I grasped my shaft, positioned myself, and pushed firmly into Trisha's tight tunnel. She wrapped her arms and legs around me, and when I began fucking her, she thrust her hips up to meet each stroke. When Trisha had her first orgasm, her pussy squeezed me tightly and created delicious friction as I slid in and out of her.
"Fuck me!" she gasped, moving her legs so they were around my butt. "Oh, God, fuck me!"
That was the first of four orgasms before my pleasure reached the point of no return, and the first jet of cum brought her off for a fifth time, and she screamed as her pussy spasmed hard around my shaft, and my cum jetted into her. When our orgasms had run their course, I gently pulled out and stood up. Trisha, for her part, closed her eyes and lay still, breathing hard.
"Would you eat me?" Missy asked. "I'll suck you at the same time, and I'll swallow!"
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