As I sit at my desk this morning, I can hardly believe what’s happened over the past 24 hours. And it’s not as if my life isn’t often filled with excitement. But even by those standards, the last day has been extraordinary.
It all started in the elevator yesterday afternoon. I was alone with my boss, Mr. Johnson, going over our notes from his last meeting, until the young redhead Kylie came running, asking us to hold the elevator door. I reached for the ‘door open’ button, giving her a chance to jump in, and she breathlessly joined us for the ride upstairs.
I should explain – I’m Mr. Johnson’s personal assistant. I handle absolutely all of his affairs, including the one he’s having with me. Don’t get me wrong, we keep a very professional front on things, but let’s just say that my job is to serve absolutely all of his needs. I’d been on call for Mr. Johnson for nearly three years now.
Given my intimate knowledge of Mr. Johnson, I was well aware of his interest in redheads, and the fact that he’d always been interested in Kylie. She’d started with the firm as an 18-year-old intern, fresh out of high school, and now, four years later, was a stunning 22-year-old, about to graduate from college after attending night school, already with a blossoming business career of her own.
“Hi, Jacob,” she said, smiling at my handsome boss, and then, looking my direction, “oh, hi, Jennifer.”
It was just like Jacob to take a beautiful young intern under his wing, ask her to call him by his first name, and assure her that she could come to him with any problem, while he continued to insist that I call him ‘Mr. Johnson.’ Not that I minded, it was just one of the many little games we played.
“How is everything going, Kylie?”
“Great, just great. I’m in my last semester of school! Hey, that reminds me, you never did take me for that drink when I turned 21. You promised!”
“Yes, you’re right. I still owe you that one.”
“I still can’t believe I’m already 22, and about to graduate.” She pushed her fingers through her stunning natural red hair, wearing her flirting on her sleeve. I chuckled to myself, knowing that he would be drawn in by her charms.
“It seems like just yesterday that I was in high school, on the soccer team, captain of the cheer squad…”
“You were a cheerleader? I didn’t realize…”
“That’s right, short skirt, pom poms, and all.”
“Really,” he said, casually, in that way he did that made hot young women feel comfortable to go on, to share more details. “Don’t suppose you still have that uniform, the company could use your support for the next big deal we have on the horizon!”
“Well,” Kylie said, flashing her big blue eyes his way, “as a matter of fact, I do still have it. Still fits, too!”
My eyes opened wider, and I was once again amazed at Jacob’s ability to make the most of a conversation with a flirtatious young woman. He was in his mid 40s, dashing, confident, successful, the perfect combination to be appealing but also to make those around him comfortable.
I caught his eye, and immediately gathered that he was turned on by this scenario. I couldn’t deny my own intrigue, actually. It wasn’t every day that a sexy young woman so confidently threw herself at a company big wig, and he’d be a fool not to take advantage of the situation.
“So, Kylie, how about that drink tonight after work? Jennifer, you join us too, we’ve got those numbers to go over before tomorrow’s meeting.”
Amazing. He’d just arranged to have drinks with his 26-year-old blonde assistant and a 22-year-old redhead who was clearly throwing herself at him, yet he maintained a completely businesslike demeanor. Once we arrived back in our offices and parted ways with Kylie, I shared with him, as I had many times before, my amazement.
“Wow, how do you do it? The hottest young women don’t even think twice before sharing just about anything with you!”
He just smiled in response.
“You do remember, I was a cheerleader in high school, too?”
“Sure. In fact, why don’t you bring that up when we meet Kylie this evening.” He reached out and grabbed one of my breasts, giving it a quick squeeze, as he often did while we worked during the day. “Should keep the conversation interesting, at least for me.”
“Yeah, yeah. Why don’t you let me get back to work.”
After work, Mr. Johnson and I walked the two blocks to McSweeney’s, the pub of choice for many businessmen in that part of downtown. Kylie arrived a few minutes later, and as she entered the bar and looked around for our us, I studied her, fascinated by her forwardness and with Jacob, wondering if she had a plan in mind or if she was just trying her luck.
She and I actually had very similar builds – both about 5’4″, size ‘2’ or so, and with big blue eyes. We were dressed similarly as well, the expectations of the company being for quite professional attire, so that the biggest difference the casual observer would notice between us would be our hair color – mine a natural blonde, and hers the spectacular natural red. We both wore our hair down, flowing to just below our shoulders.
Once Kylie joined us, we ordered a round of drinks, and toasted, belatedly, to her 21st birthday. Mr. Johnson – Jacob – was once again all professional, asking Kylie what she planned to do when she finished her degree, whether she’d stay with the firm or look to continue her career elsewhere.
Once we satisfied his curiosity on that topic, and the drinks had warmed and loosened us a bit, Jacob shot me a quick glance and I turned the conversation back to that which had intrigued us earlier.
“So, Kylie, did you know I was a cheerleader in high school, too?”
“Really, wow! What were your colors?”
“Blue and white, yours?”
“Ours were green.”
Jacob was silent as Kylie and I chatted about the woes of cheerleader outfits: the too-short skirts, spankies, the huge gaudy bows we would wear in our hair.
“Actually,” Kylie volunteered, “I had a secret trick about my skirt that worked for a few years before my coach made me get a new one.”
“Really,” I asked, “what was that?”
“Well, I lost about 15 pounds after I was fitted for my uniform, so my skirt was actually too big. So I was able to wear it low on my hips so that it came down to, like, mid-thigh, when all the other girls’ skirts barely covered their asses.”
“But it sounds like your plan caught up with you in the end?”
“Yeah, eventually, coach made me get re-fitted. So my skirt barely covered my ass during my senior year. That’s the uniform I still have.”
“The one that still fits you?” Jacob broke his long silence.
“That’s right. I actually brought it with me tonight, if you don’t believe me. It’s in my car.”
Amazing. That was just the kind of thing that always happened to Jacob. Was it luck, I always asked myself, or the kind of karma reserved for the sexiest guys on the planet?
“Hmm, interesting. Well, we can’t just have you trying on cheerleader outfits in the parking lot. I don’t suppose there’s anywhere else we could go?”
Tipsy as I was, it didn’t take me long to put together a plan.
“We can go to my place. It’s not far from here, plus then I’ll get to try mine on as well. It’s been a few years, but I’m pretty sure it still fits.”
“Cool!” Kylie’s cheeks glowed red, undoubtedly a combination of alcohol and anticipation of the night’s activities.
I gave Kylie directions for the quick drive, we each found our cars, and met up a few minutes later outside my apartment.
Mr. Johnson knew his way around my apartment – he’d spent the night many times before – so he made himself comfortable on the sofa while I showed Kylie to my room. I hunted through boxes in my closet for my own uniform while she quickly changed into hers, and a few minutes later, we were both transformed into the cheerleader versions of ourselves, our perfect shapes poured into the tight-fitting tops and skirts, our hair up in ponytails. Needless to say, neither of us had in our possession spankies to match our uniforms, so we both went without anything under the skirts.
We giggled as we skipped back into the living room, making a half-assed attempt to remember some of our favorite cheers as Jacob looked on. I knew even before looking in his direction that he would be completely turned on by this scenario. He’d made no secret of the fact that among his fantasies was being with two women at once, at least one of them a redhead. And obviously the cheerleader outfits didn’t hurt, either.
It wasn’t long before Kylie looked in his direction, and blushed hotly as she saw his obvious erection. Much to my surprise, she didn’t hesitate or wait for an invitation before walking towards him, kneeling between his legs, and beginning to stroke him. Just a few moments later, she had unzipped his slacks, freed his bulging cock from his boxers, and sucked his entire length into her mouth.
I gasped as I watched her deep-throat him, something that had always been a challenge for me, impressive as his cock was in size. Don’t get me wrong, I knew how to bring him pleasure, but taking his entire length into my mouth pushed me to my limit, causing me to gag. When my eyes met his, Jacob smiled and said, “Jennifer, you might want to make a note of her technique…”
I sat down next to him on the sofa, watching Kylie as she continue to bob up and down on him, marveling at her technique and stamina. Jacob began fondling my tits as we both watched Kylie suck his cock. Kylie looked up towards us, her mouth not leaving the task at hand, as I reached down to fondle his balls.
Jacob now shifted our position, lying down on the sofa, his head on a pillow, and encouraging Kylie to climb up off the floor and join him. As soon as she was back in position, she resumed her attention on his cock, while I stood above him, giving him access to begin fingering my pussy with.
I was surprised at my own reactions to watching another woman go down on Jacob. Whether I was turned on by the sight itself, or just aware of the intensity of his pleasure as a hot, hard-bodied redhead bounced up and down on his cock, I found my own pleasure mounting more quickly than normal. After a few minutes of his fingers expertly exploring my clit and the outside of my pussy lips, I pulled myself closer, lowering myself down until I was sitting on his face and his tongue plunged into my pussy. I came almost immediately, crying out in pleasure as I continued to watch Kylie, the intensity of my pleasure drawing her attention to me until our eyes met at my climax.
Once I had recovered enough to shift my position, Jacob encouraged us to switch positions.
“That was incredible, Kylie, I think you’ve earned some pleasure of your own. Let’s just see if Jennifer learned anything from watching your technique.”
Determined to prove myself, I knelt on the sofa between his legs and slowly took inch after inch of his cock into my mouth. Forgetting all but the intensity of my recent orgasm and relying on my slightly competitive nature, I managed to take in more of his length than ever before, holding it there as Kylie positioned herself for his attention.
Continuing to pleasure him with my mouth, I watched out of the corner of my eye as Kylie leaned against the back of the sofa, spreading her legs wide, her cheerleader’s skirt bunching up around her hips as Jacob’s fingers explored the glistening wet patch of red hair at her crotch.
She panted as he began stroking her clit, whimpered as he first pressed his fingers into the folds of her pussy lips, and cried out as he penetrated her with first one, then two, then three fingers. I kept up my slow but steady rhythm on his cock as he brought Kylie closer and closer to orgasm, watching as he grabbed her by the hips, pulled her closer, and brought his tongue to her clit to finally push her over the brink of a dramatic orgasm.
Once Kylie could pull herself to her feet again, she and I both climbed off the couch and followed Jacob’s instruction to remove our tops. We then kneeled before him as he stood, and began taking turns stroking and sucking his throbbing cock. I watched Kylie’s beautiful tits bounce up and down as I took Jacob’s balls into my mouth while she sucked in his entire shaft once again.
After a few minutes of this delightful attention, Jacob was finally approaching his own climax, and asked Kylie’s permission – he already knew that he had mine – to shoot his load all over our chests. This was a favorite activity of ours, and I never tired of the feeling of his wonderfully warm cum dripping from my skin.
But this time was different. I couldn’t take my eyes off of Kylie as I watched his cum hit her chest. Her beautiful eyes, her luscious hair, her hard nipples, all distracted me from the usual sensations of his cum on my skin. Before I knew what I was doing, I took her into my arms and began licking his cum from her skin. If Kylie was surprised, she certainly didn’t object – in fact, she returned the favor.
“You don’t know how happy this makes me, girls, that not a drop will go to waste,” Jacob said as he sat down on the sofa, spent, to watch us.
I arched my back as her tongue first found the sensitive skin around my hard nipples, sucking the cum from them and then nibbling gently. I pushed her to the floor, pressing my body against hers, and ground against her, reveling in the sensations of breast against breast, clit against clit. The thought that I was making out with another woman – a first for me – flitted briefly through my mind, but if I should have stopped to consider my actions, the heat of the moment was too much to allow me to do so.
Kylie moaned, “oh, god, Jennifer, that’s amazing,” as she rolled us over, pushing my legs apart and rubbing against my clit with her thigh. Our instincts directing us, we shifted our position until our legs were interlaced and we could truly grind against each other, our dripping-wet pussies lubricating our motions, as we pushed closer to climax.
Before allowing us to become completely lost in the moment, I slowed our motions, pulled Kylie close, and whispered in her ear. She giggled and smiled in agreement, and we scrambled up off the floor. I disappeared into my bedroom for a moment, and returned with my hairbrush and two hair ties for each of us – in colors matching our uniforms.
With Jacob still comfortably resting on the sofa, Kylie and I stood before him, taking our hair down from the single ponytails we’d started with, and slowly taking turns brushing each other’s hair, tying it up into two pigtails. About halfway through this process, Jacob began stroking his cock once again, barely able to contain his excitement as he watched us.
“I think we should continue this in the bedroom, girls,” Jacob said as I put the finishing touches on Kylie’s pigtails, her red hair shining in my hands as I tied it up.
I didn’t need any further encouragement, putting the brush down on the coffee table as we all hurried for the bedroom. Jacob took the time to remove all of his clothes, which he hadn’t done earlier, as Kylie and I made ourselves comfortable on my king-sized bed.
I began kneading and sucking Kylie’s tits as Jacob grabbed her hips, pulled her towards the edge of the bed, and began rubbing the head of his cock slowly back and forth against her pussy lips. Just as soon as she couldn’t stand the suspense any longer, he plunged fully into her, and she cried out in delight at the intensity of the penetration.
After a few moments, he pulled out of her again, climbed on to the bed with us, and without warning, plunged into me from behind, doggy style. I cried out as he bottomed out inside of me, and then he remained there, still, as Kylie, still lying on her back beneath me, reached up and fingered my clit.
As I began moaning in pleasure, Jacob gradually began moving in and out of my pussy, increasing his pace until he was pounding furiously. Her fingers never once leaving my clit, Kylie reached up and caught my lips in a kiss, where we remained as I rode out the waves of pleasure of one of the most intense orgasms of my life.
After what seemed like hours, my pussy sore but satisfied from the intense pounding Jacob had just given me, I collapsed to the bed to watch him turn his attention to Kylie. He flipped her over onto all fours, slowly pressed into her, and then grabbed her pigtails as he began fucking her just as intensely as he had fucked me a few minutes before.
I knew he was close to his own climax now, and that if Kylie could hold out long enough, she’d have the satisfaction of reaching orgasm with him. Crawling beneath the two of them, I positioned myself so that I could give attention to both her clit and his balls with my hands. As soon as I found their rhythm and added my touch, they both began to pant in pleasure, and it wasn’t long before both collapsed to the bed with me, completely spent.
The sun woke me up the next morning, and I found myself lying with my spooning with Kylie, with Jacob nowhere to be found. I woke her with gentle kisses and nibbles on her earlobe, and we both spent a few luxurious moments lounging, remembering the myriad sensations of pleasure from the night before, before realizing we should get out of bed and see what had become of Jacob.
I called out his name, and once there was no answer, I knew he’d already been up and out on his way to work. Nothing would slow down that man’s work ethic, least of all the fulfillment of a sexual fantasy. I smiled to myself. He’d probably be even more of a task-master than usual that day.
I walked into the kitchen, still wearing my cheerleader’s skirt, and still covered in dried sweat and cum. He’d made coffee. He’d made breakfast. And there was a note. I picked it up and carried it back to the bedroom, where Kylie was sitting on the edge of the bed, stretching. I handed her the note, and she read it aloud.
“Jennifer, don’t forget our 9am. Kylie, I want you to be there, too. Thanks you two, that was awesome.”
We both glanced at the clock next to my bed, which read 8:20. Yikes. Given that we both desperately needed a shower, we’d be pushing it to make it to the office on time.
“We’ll have to shower together, Kylie, or we’ll never make it.”
“Guess so, Jennifer. Let’s go!”
I unzipped her cheerleader skirt and she mine, until we were both naked for the first time since changing our clothes together the night before. I took her hand and led her into the bathroom, turned on the water and waited for the temperature to rise, and then pulled her in to the shower with me.
I can’t speak for Kylie, but her actions showed that she was still just as turned on as I was. For a few moments, we allowed ourselves to be pulled into the moment, rubbing our soapy bodies together, our hands exploring, before I finally stopped us, thinking of Mr. Johnson’s disappointment if we were to arrive late to work.
“We’d better cool it, Kylie, and get going.”
She smiled and we finished our shower. We took turns with the blow dryer, and then I helped her to some of my clothes. Turns out Mr. Johnson isn’t the only one in this situation with incredible luck: the fact that Kylie and I just happened to be the same size meant that she could avoid the ‘walk of shame’ back at the office. Instead of the outfit from the day before, she could choose from my well-stocked closet of tailored suits and present herself professionally.
“So, Jennifer,” she asked me as we arrived at the office, “do you think we’ll ever get the chance to do this again?”
“Don’t worry, Kylie. Once Mr. Johnson discovers something he likes, he doesn’t let it go.”