Climbing the Ladder

So there was an interesting dynamic at play as we entered Rachel and John's place that evening. It was a nice house in the suburbs; not a mansion, but comfortable and an indication of some success by both occupants. John was in marketing for some type of computer software firm that I'd never heard of. I truly knew almost nothing about him before that night.

It was warm enough for drinks and dinner to be out on their deck and, as I predicted to Phil, Rachel took command of the conversation. I found John to be intelligent, introverted, and very discerning as to when he chose to take part in the discussion. However, he did seem to have a dry sense of humor that I liked.

Also, he was actually a little more good looking than his picture in Rachel's office indicated. His hair was conservatively cut and he was what my mother used to call ruggedly handsome. Overall, there was a quiet anonymity about him that, admittedly, I found rather fascinating.

Rachel, to my surprise, was more of a flirt than I anticipated and I don't think the alcohol had all that much to do with it. She latched onto Phil's fixation with her and played up to it without ever crossing the line of indecency. John and I simply watched it unfold, waiting for any sign that intervention was necessary. It never happened.

We parted with a promise to do it again sometime. In the car on the way home, I couldn't resist taunting Phil.

"Are you ready to leave me for her?" I asked.

He chuckled. "That'll never happen, Charlotte."

"But if she offered to pose for you, you'd accept?"

His smile gave him away. "If she paid me like everybody else."

I leaned over and put a hand on his leg. "Like I paid you?"

I reached for his crotch and rubbed it. Phil spread his legs as much as he could and still drive. I pulled down his zipper and reached inside his pants, putting my palm on his boxers and pulling up on his cock. A moment later I had it out and I stretched out on the seat with my head in his lap.

Thirty seconds of licking and stroking had him hard. I sucked him with every indication that I wasn't going to stop until he came. I could feel his cock throbbing and the warmth of it filled my mouth. At the first twitch of his body and corresponding moan, I stopped.

"If you convince me at home you love me more than Rachel, I'll finish," I said as I put his cock away the best I could.

The look of lust on his face was unmistakable. It was going to be a fun night.

An hour later we were naked in bed, my head on Phil's chest and my fingers very lightly running up and down his rock hard erection. He had one hand on my back, but it occasionally shifted to the side of my breast.

"You'd fuck Rachel if you had the chance, wouldn't you?" I asked.

"Probably," Phil said honestly.

"What is it about her?"

He paused and I felt a jolt in his chest when I played with the tip of his cock.

"I don't know. She's not as good looking as you, obviously, and I doubt if she has your body," he said. "It's just...."

"She doesn't like to show it off much, does she?" I interrupted. "It's just what?"

"She's sexy," he said frankly. "There's something about her that's just...sexy."

"Even though she's forty?"

Phil took in a breath when my nails scraped the length of his cock and onto his balls.

"She doesn't act that old," he said, squeezing my nipple with two fingers. "What do you think of John, by the way?"

I smiled at what may or may not have been his effort to change the subject. "I like him. He kind of fascinates me. But I don't fantasize about him like you do Rachel."

"I don't fantasize about her. Jesus."

I took his cock in my hand. "But you want to fuck her."

I stroked him harder and Phil's body stiffened. "You asked if I would if I had the chance."

I brought him closer and closer to an orgasm. Then I said, "We should find out what she would do...given the chance."

"What?" Phil asked in amazement.

"We should give her the chance."

I saw a drop of precum on the tip of his cock. Phil's breathing was rapid and irregular.

"How?" he could barely ask.

"We'll talk about it later. Now show me you love me the most."

I rolled on top of him and sat on his cock for one of the wildest rides we ever had. I wondered what, or who, was on his mind the entire time.

I didn't bring the subject back up until the next day. When I did, I proposed to Phil that we invite Rachel and John over and, in the most suitable way possible, run the idea of a one-time swap past them. We weren't sure how it might play out, meaning: we didn't know if Phil would talk to Rachel or if I would, or both of us, or what. We agreed to play it by ear and even went so far as to say we wouldn't bring it up if the mood of the group didn't seem right at the time.

A date was set. Phil and I made every effort to give them the best food, drinks and environment we could in our humble abode. We were both nervous, but the evening went smoothly with Rachel being her usual flirtatious self around Phil. That made it a little easier when Phil was alone with Rachel, showing her the makeshift photography studio he had built from a converted extra bedroom.

According to Phil's account to me later of what happened, it went something like this:

Phil and Rachel went into the studio, leaving me to entertain John. He said Rachel initially showed interest in the lighting and props and cameras.

"How many customers have you had? Or aren't you really to that stage yet?" Rachel eventually asked.

"I'm beginning to do a little advertising with flyers and stuff," Phil told her. "A lot of word-of-mouth marketing as well. I've had maybe a dozen people, some couples. Even a pet that somebody wanted pictures of."

She laughed. "Has Charlotte posed?"

Phil had to pause, knowing that he didn't want to go into all the details, nor did he want to lie in case Rachel talked to Charlotte later.

"Uh, yeah. Once. It was more practice than anything," he said.

Rachel was examining a light, and said, "You have a portfolio, I assume."

Phil pulled out his samples album and laid it on a nearby table. Rachel began to flip through the pages until reaching the end.

"No nudes?" Rachel asked with a wicked grin.

"Um, not yet."

"Not even Charlotte?"

Phil was always a lousy liar. His hesitation and awkward look back at Rachel told her all she needed to know.

Rachel said, "I think in a private setting like this that posing nude would be...kind of fun."

She stepped closer to Phil and added, "But then, I would think almost any woman would be glad to get undressed for you, Phil."

"I guess I just haven't found them yet," he answered.

"Oh, maybe you have and you don't realize it," Rachel said. "I think I could be talked into almost anything under the right circumstances."

They were close enough to touch.

"If we were alone in here with no possibility of being interrupted?"

She smiled and said, "Especially then."

"It can be arranged," Phil told her.

Rachel's eyes widened with curiosity. "Would you? And would Charlotte?"

Phil nodded. "But with one caveat."

"Name it."

"She gets equal time with John."

Rachel ran her hand down Phil's arm and onto his fingers. She lingered there for a moment before brushing her hand across his crotch.

"Well, I guess I'll have to ask him," she said in a near whisper.

I hadn't gotten nearly as far with John, nor was it my intent to. But clearly we learned a lot about each other in that short period of time and, I had to admit, became pretty comfortable with each other. It was obvious to me that John was a different person without Rachel around. He was much more sociable. Very friendly, in fact.

I was excited to hear Phil's story when John and Rachel left that night. It seemed so improbably that it might actually happen under damn near perfect conditions of consent involving all parties. The big question mark was John and for some reason I was confident he wouldn't put a stop to it.

When Rachel called me into her office at work and told me it was OK with John, it was hard for me not to show my pleasure in the news. We agreed, without question, that it would be a onetime event, taking place during the day instead of overnight, and that no plans for meeting each other again would take place without the blessing of all four people.

Rachel was to come to my place and I was to spend the day at John's. No restrictions were ever discussed.

Not knowing if there were customary ground rules for this type of thing, I could only assume that those were fairly good guidelines. I kept thinking it was much more obvious what Rachel and Phil would do with their time. It was less clear to me what my day would be like. That didn't bother me. The mystery added to the buildup.

Thus, two plays were acted out on two separate stages on the chosen day. It's only fair you hear of both. I'll begin with mine.

It was a warm, sunny Saturday. I wore a tank top and shorts and threw a bikini in my bag in case we spent time on the deck and in their pool. I felt like a teenager on my first date when I knocked on John's door around noon and he welcomed me in.

From the very beginning, John was a completely different person than the one I knew from before. Without Rachel around, he was cheerful, sociable and chatty. Not that he ever seemed unhappy around her, but clearly she dominated whenever the two of them were together. He came out of his cocoon without her.

John may have been more genial because we were alone, but I could still sense his anxiety about the whole thing.

"You've never done this before?" I asked him while we sat in his living room.

John laughed. "No. Never. How about you?"

"Nope. But I liked the idea," I said, hoping to ease his mind a little.

"Me, too. But if it's OK with you, I'd like to, uh, take our time," he said hesitantly. "We have all day."

I smiled. "I agree. And I'm very good at taking orders. Whatever you want me to do...."

I'm pretty sure he blushed, but nodded his approval. Then he said, "I was going to grill something for lunch. Is that OK?"

"That sounds perfect."

"Let's go out back," he said, leading the way onto the deck.

It was actually very pleasant to just sit there in the sun, sip a drink, and watch John work the grill. I could sense we were both gaining confidence that the day might work out after all with each passing minute. Only once did I give a thought about Phil and Rachel, and that thought was: I bet they didn't wait this long.

John and I ate our lunch learning more about each other. He was very good at not disclosing anything about work that I expect he learned from Rachel and was none of my business. The only disappointment was the fact I only caught him glancing at the braless breasts inside my tank top a couple times. But it was early, yet, and I hadn't truly started to flirt.

That began shortly after we ate.

"I'm going to want to get into the pool soon," I told him. "Mind if I change into my bikini?"

"Am I supposed to say 'Yes, I mind' to that?" he asked in jest.

I laughed and started to enter the house. I looked over my shoulder at the door and said, "You're going to swim, aren't you?"

"Yes."

"Are you changing?"

He grinned. "I swim naked."

He could hear my laugh as I disappeared behind the sliding glass door. Moments later, when I walked back out onto the deck in my bikini, I got the looks I wanted earlier. John eyed me from head to toe multiple times, even after I took the chair next to him.

"Very nice," he exclaimed.

"Thank you. I rarely wear this in public."

"I'm honored," he said. "You are denying men a magnificent body."

"C'mon," I said. "I'm going down to a chair by the pool. Grab a drink and join me. And you're not welcome if you don't at least take that shirt off."

He did, indeed, join me and I was pleasantly surprised at his well-toned body when he was down to just his shorts. Not that I thought forty year old men were incapable of being in shape, but John evidently took it seriously.

We laid on lounge chairs and talked for fifteen minutes. Then I jumped into the pool with John watching every move. I grew up by the ocean and was a good swimmer, so I quickly completed two laps and rested my arms on the edge facing him.

"Get in," I pleaded.

"No suit," he replied.

"You swim naked. Get in."

Sure enough, he dropped his shorts and almost in the same motion dove head first into the water. In that short instant, I saw a very, very nice cock that showed signs of having been affected by his watching me. I turned to watch John resurface and glide over towards me.

I leaned against the side of the pool while John tread water just in front of me.

"You're not supposed to swim within an hour of eating," I said.

"Who said anything about swimming."

John came closer, pressed his body against mine, and kissed me. The water was up to our necks as we stood on our tiptoes—at least, I had to—and embraced. The kiss grew in intensity very quickly. My hands slid up and down John's back, finally resting on his bare ass. John went straight for my tits, seizing them with both hands and nearly forcing my bikini top right off.

At the first break in the kiss, I said to him, "Can't people see us?"

"Maybe."

I just stared at him for a second, and then he added, "Doesn't that make it just a little more stimulating?"

I put my hand around his cock.

"I guess so," I said with a smile at the feel of his budding erection.

We kissed long and hard again with John probing the inside of my suit, both top and bottom.

"Take it off," I begged breathlessly.

He only removed the top at first. Despite having half of his head under water, John sucked my tits and I almost laughed at the sensation of him doing it underwater. But it felt too wonderful to laugh.

When he came back up, he said, "Sit on the edge."

I jumped up and John removed my bikini bottom. The next couple minutes were ecstasy as he ate me with incredible skill. His tongue probed every inch of my pussy and stabbed at my clit just enough to bring me close to cumming and then letting me relax. Then he was licking me again and I moaned in delight.

John pulled me into the water and said, "Turn around. Brace yourself on the edge."

I eagerly did as he said and spread my legs when I felt him move closer. He wrapped his arms around me and held my tits.

"You said you would do anything?" he said into my ear.

I nodded.

"Then I want you to cum for me. I want to hear you cum, Charlotte."

John had placed his cock at the entrance to my pussy. I was practically shaking with desire when I felt the tip begin to enter me. He squeezed both nipples at the exact same time he thrust forward.

"Ohhhhhh God!" I cried out. "Yes, John. Yes!"

I braced myself and he fucked me harder. The water splashed over the edge as we both swayed back and forth, John's thick cock easily filling my pussy with each plunge forward. He moved a hand down to my clit and rubbed it.

I begged for more and bent over at the waist, pushing my ass and pussy back into him. I couldn't believe the satisfaction his cock was giving me, considering the last time I saw it John wasn't really hard yet. Now it was swiftly edging me closer and closer to an orgasm.

"C'mon, Charlotte. That's it. Cum so I can hear you," he urged.

I could only moan and sense my body building up to a climax. I could care less who could see us or hear us. John was driving me crazy.

"Harder, John! Yes. Yesssss! Ohhhh fuck."

He stroked my clit harder and I shrieked, "Now! Now!"

Those were the last words he could understand. My pussy contracted and squeezed his cock again and again as I came. Small waves bounced off the side of the pool and back against my tits, exciting my nipples even more and prolonging the already lengthy orgasm.

John timed it perfectly. He cried out and began to empty his cock into me in unison. Our combined moans of joy most likely would have been audible to any neighbor, but we never hesitated in continuing to fuck and cum and let each other know about it.

John was outstanding, to say the least. The quiet guy I first met just needed to be on his own and I was a more than willing participant.

We somehow managed to climb out and fall into the lounge chairs when it was over. Several minutes later, we reentered the house with clothes in hand.

"Don't get dressed," John requested. "I like you the way you are."

"I don't mind at all. Now I can get a better look at what made me cum so hard," I told him.

We sat and talked for a long time, completely comfortable in our nakedness despite the novelty of it all. I was a good girl for as long as I could, but moving about the house as we did in that time and watching each other the entire time finally caused me to cave.

I found myself between John's legs as he sat on the couch. I was on my knees licking my way up to his balls and cock. I could see him getting harder when I kissed his balls and I could feel him throb when my tongue skated from one end of his cock to the other.

I teased him unmercifully with my tongue and lips until I thought his long, thick cock would explode. That was what I had felt inside me in the pool and that was what I wanted in my mouth. I sucked on John's cock for a couple minutes, taking him as deep into my throat as I could. His groans told me he was close.

So I climbed into his lap, sat on the superb hardness of his shaft, and leaned forward to let John suck on my tits. My nipples and clit have always been my 'weakest' points. It only takes a little manipulation in those areas to bring me to the brink of an orgasm and John was very, very skillful. He knew just how hard to bite and when to lick. All the time, his cock slid in and out with the help of my wet pussy.

If we had gone the rest of the day like that I would have been happy, but I knew I would cum too fast. And God did I cum. The second episode of sex I have in a fairly short span is always better. This was fantastic. John definitely heard me and his own orgasm continued even after we fell sideways onto the couch and he kept pounding his cock into me.

Soon after we finished, John looked at me and said, "Thank you for being so...patient, Charlotte. Rachel has a tendency to be, um, I guess I would call it aggressive. Today was very, very nice."

I didn't ask John to expand on what he meant. Ends up, I didn't have to. As soon as I heard Phil's account of how his day with Rachel went, I understood.

Phil answered the door and let Rachel in, glad to see her informally dressed for the first time. Rachel was well known for her dressy outfits at work, but she showed up in Capri pants and a casual short sleeve top that buttoned down the front.

He had barely closed the door when Rachel pulled him toward her and initiated a shockingly adoring kiss. It took a few seconds, but Phil allowed his attraction to her to kick in and the two were soon pressed against the wall in a lengthy introduction to each other's bodies.

Before it was over, Phil had turned Rachel around and was leaning into her, gripping her bare breasts through the top and feeling his cock harden under her palm.

Rachel was the first to speak.

"I don't want my title at work to interfere with what we do today, Phil," Rachel said. "For the next few hours we are friends, free to do whatever we want."

Phil was pretty sure from the moment she walked in the door that Rachel's title wasn't of great concern to him or her, so he didn't see the need for her speech. But he assured her everything was fine. His cock assured him it was going to be an interesting 'few hours.'

Phil didn't waste any time before asking Rachel if she wanted anything to eat or drink and was in the kitchen listening for her answer when he saw her following him into the room. He was about to open the refrigerator but was stopped by her arms wrapped around him.