(This one is so long too! I SWEAR tried so hard to keep it shorter but I just failed completely lol. I even broke it up into little sections thinking that’d help and there’s a couple parts where I mention trying to keep it brief and you’re going to be like “wtf is she talking about this long af” but whatever I’m not changing it. So here we go!)

Trina: I have a younger cousin Trina who is in her first semester at college right now. She’s not really my cousin, it’s a tedious connection but I call her my cousin. Now obviously I’ve known she was a hot little thing and she gets plenty of attention from boys, but I didn’t really realize how much we had in common until one day she confessed to me that she’d been fucking not one but two of her professors for good grades and I in turn shared that my whole life is naught but an intricate web of sexual relationships, favors, and tensions and we sort of bonded over that. I’m also secure enough to admit that I am vaguely threatened by her. I’m a beautiful desirable woman with very high confidence, all of my life experience affirms this. But I am, let’s say, closer to my milf era, and maybe on the other side of that fleeting youthful beauty that that an eighteen year old has. And that’s 100% fine I’m not trying to be an innocent little girl for anyone. But everyone once in a while Trina says stuff like “Did Snapchat exist when you were in college?” and then I do want to murder her.

Sexy Tom: So anyway put a pin in that for a sec as I explain that I don’t really have a boss the way most people do but I have a rotating cast of boss-ish people. One of these is a guy me and the work girls call Sexy Tom (actually we call him Tom Tom, articulated to mean the same thing but in a way that doesn’t really translate to the written page. And obviously the name isn’t really Tom either so its more like “naaame name” but just work with me here, okay?) Sexy Tom is just one of these corporate guys who can absolutely get it. He’s proper and loose at the same time, he speaks in corporate speak but he makes it sound natural and he has such confidence almost resembling a smirk in his eyes when he talks that he sounds completely sincere but also slightly ironic at the same time. You see what all the other guys are going for when he talks. He could tell you you’re fired and you’d apologize to him for having to fire you and then he’d give you a look and you’d apologize for apologizing. He has that kind of aura. He’s got salt and pepper hair so you know he’s in charge but also one time on a boat he had his shirt unbuttoned just enough to reveal a hint of a chest tattoo? Ugh fucking kill me.

Sexy Tom is married I think with kids but the the man absolutely slays vagina. Like, for sure I had to buy new underwear every time I spoke to the man, and we did have a flirty report, but he also had that vibe where maybe he was a serious devoted family man and would smack you upside the head for even suggesting anything, which honestly just made him hotter, except that he could ruin my career which I do take very seriously. Which of course made him even hotter.

Sorry, this literally IS me trying to keep it as brief as possible. Those are the only characters who really matter in this story.

The BJ: We did some good work at work one day and we were all celebrating with some cocktails and I was giving Tom my brightest eyes and did a toast to him and sat next to him and basically just ran down the slutty secretary playbook, but he’s so cool he wasn’t giving me anything back and just when I thought hope was lost he squeezed my butt! Just one quick hard squeeze right there at the table, it was so subtle. Someone else was talking and he wasn’t looking at me and neither of us acknowledged it, but my heart and my pussy just melted instantly!

So naturally about 45 minutes later I was kneeling down in front of him in one of the comfy chairs unzipping his pants and taking his cock out, both us of still in our work clothes. And it was as big and beautiful as I’d hoped! I joyously put it in my mouth and went to work, just rewarding him for being him, and he gently stroked my cheeks and ran his hand through my hair. He did a very calm sort of dirty-talk monologue while I blew him, not dissimilar to how he talked during meetings, very self important and vaguely inspiring but not totally coherent - Which is good, no one should be coherent when their cock is in my mouth - I looked up at him with big listening eyes as I moved up and down him and he spoke esoterically about success and excellence and stuff like that sometimes looking down at me and sometimes staring stoically off into the distance. I was happy for him. He was having such a good time right now. I kind of wished I could be him, sitting there basking in financial success having my dick sucked by me. What a good day. He even sipped his drink a couple times, like he was Daniel Craig or something. Get it, Tom.

But I knew I had him on the rocks when he hard-pivoted to sexual experiences. He closed his eyes and started reminiscing about interns he’d fucked, a subject matter in which I was extremely interested, but before any clear narrative formed he grasped the sides of my head and tilted his neck back in ecstasy as he unloaded into my mouth. We were both in nice clothes so I was extra careful to keep swallowing and swirling him with my tongue to make sure every drop made it down my throat before I let him go, which of course probably prolonged his orgasm but even so he was soon fully drained and the last of the evidence had disappeared down into my tummy and I let him slide out of my mouth. It’s a little hard to explain if you don’t get it, but I was so pleased to have provided such an enjoyable and sexy experience for him. I swear I could feel his cum warming me from the inside.

I almost expected him to dismiss me with a wave, but instead he patted the seat next to him. I moved up next to him and my heart fluttered as we engaged in what is the closest to cuddling I could imagine a man like that partaking in - which meant he sat with his drink in one hand and the other on my ass as I draped myself over his lap. He took a sip and very characteristically told me I was “a good kid” which I interpreted as extremely flattering (even though it really it was a pretty belittling thing to say to someone who’d just helped you make a bunch of money but whatever). We chatted a bit and I asked him about the interns and he seemed surprised I had been listening but recovered quickly and dismissively said that sort of thing doesn’t really happen anymore. I told him he deserves some new interns and he chuckled politely and squeezed my ass a few more times before declaring that we should go, and I went home feeling like a giddy schoolgirl.

The Problem: So, believe it or not, my encounter did not cure my crush on Tom but rather intensified it. A go-to fantasy of mine while touching myself and even while with other men (I briefly had a boyfriend during this time too, but that’s a story for another day) became a catalogue of made-up scenarios of Tom having sex with supple young interns. Sometimes they threw themselves at him, batting their eyes, bending over, desperate for his affection, and he tried vainly to resist until the temptation became too much and he had to experience them. Other times he would call whichever one tickled his fancy into his office, furious about some made-up transgression, insisting she’d never work in this town again unless she fucked him right then and there, and she’d beg and plead but ultimately acquiesce her pussy to his whims. So yeah I was definitely obsessed.

The Plot: The line between a daydream and a plan is a precarious one and it’s hard to pinpoint exactly when they started to bleed into one another. I can say for certain that I was fixated on Tom fucking interns in a theoretical sense, but obviously I would have to be involved in a practical sense. I also knew he had an annual birthday party at the end of October and so over time the idea of giving him a threesome with myself and an intern for his birthday became tickling.

Obviously I did not have an intern (I wasn’t even sure if Tom’s company still had interns, let alone be in a position to talk one into group sex with her boss) but right around this time I had that conversation I mentioned way back in the first paragraph with Trina and I figured what the hell, any old college kid would probably work, in fact she was even younger than an intern would be(, which I feel like is… better anyway?... right? Like if we’re going to fetishize nubility we might as well go all the way with it?). If there was a true catalyst between a daydream and Ocean’s Elevening a scheme, this was it. It actually wasn’t that hard to talk Trina into it. The “intern/boss” dynamic did nothing for her, but she was surprisingly just into the idea of being given as a birthday present to a sexy older man so. Hey whatever works. (She also said she liked that I’d “be there to protect her” which I sort of rubbed me the wrong way. Like I get it but also kinda bitchy. I’m not your pimp, ho. You’re here to make MY fantasy come true. Anyway. She said yes and that’s what matters.)

Phase two was a location. I’d originally imagined sneaking off to a hotel until it proved ridiculous to get the birthday boy away from his own party. However, there was a haunted house at the venue for a different Halloween party that I’d confirmed would not be staffed that night so I settled on that as our location. Phase three was getting Trina in. Obviously it’d be super sus to bring my 18 year old cousin who never met my boss to his birthday so we had to elaborately sneak her in the back. I overestimated this one. I just opened a door and she walked right in and went to the haunted house room. Nobody cared. A character who didn’t make the cut as “important to the story” (aka one of the girls who calls him Tom Tom with me) pulled Tom away from the party (and his wife) and insisted he go through the haunted house blindfolded for a birthday surprise (the blindfold was originally to counteract the haunted house. It was dark and there were some weird red and orange lights and spooky props, it didn’t make sense with the fantasy. Neither did the blindfold honestly but at least that was kinky in its own way. I was going off book. Sometimes on a heist you gotta improv) Our wild midpoint event was when we were waiting in the haunted house, with Tom on his way, some staff member walked in! Everything was risk! The plan could be completely ruined! The drama! The suspense! Except he saw us in there he just said “oh sorry” and left. So, honestly it all went pretty smooth.

THE MAIN EVENT: We heard Tom and work girl outside which was our cue to undress and we were quickly both naked. Finally Tom came in blindfolded and I closed the curtain behind him and lead him to the center of the room where I squatted next to him and pulled his cock out and gave it a few teasing licks. I’d imagine as a man when someone pulls you away on your birthday and says there’s a special surprise for you, you kind of hope it’s sex but you also don’t really expect it to be. Well this time it was. He whispered his wife’s name in confusion and I chuckled as his cock grew in my hand. It was even nicer than I remembered. Then down my throat it went. He gasped and weakened at the knees and he instinctively grabbed my hair. He moaned pretty loud and I had to spit him out for a second to shush him. He was clearly disoriented and also seemed to think his outburst had cost him the privilege of his experience and he reached up to his blindfold with a desperation I’ve never seen on him but before he took it off my lips found their way back around his cock and his panic subsided and his cool returned. He was understanding what was happening.

But it had only just begun. When I felt he was sufficiently fluffed I released him again from my mouth and lead him by the cock over to Trina who had been patiently waiting on a blood-covered work bench and quickly leaned back and spread her legs revealing an, admittedly, very very cute and taught little smooth pussy. He was about to have the time of his life, there was no question. I guided him right to her threshold but let him do the honor once he realized where I’d lead him. But even as he pushed into her there was amazement beneath the pleasure on his face - he was just comprehending that there was not one but two of us here for him. And I will say, it was truly hypnotic watching such a distinguished and dignified man’s big beautiful cock work its way into Trina’s petite little body, squeezing into that tiny hole. She squealed with delight which confirmed to Tom, who surely already knew based on what he was feeling, that he was indeed getting a very special treat today. He reached out to me, grasping blindly at my face, and finally finding it and shoving his fingers into my mouth which I promptly sucked as the last of his cock disappeared inside Trina.

He wasted no time enjoying her. He started off slow and gentle but quickly picked up speed and soon lost himself. I repositioned to lay my head on top of her stomach and when he realized this he pulled out of her and thrust into my mouth and I sucked him briefly before he went back into her pussy for a few thrusts. He repeated this pattern several times before Trina started to moan - and I swear that slut was faking it but she insists she wasn’t - which made him give up on my mouth completely, and even though he was fucking her more and more frantically she clenched up and sputtered that she was cumming and soon after he moaned and slammed conclusively into her so forcefully I almost fell off the table and it became apparent he was cumming inside her. He was definitely not supposed to do that. Oops. Comes with the territory I guess. If it was any consolation he clearly was having a religious experience as he held himself locked fully inside her with his head cocked back and mouth, seemingly in pain, for what seemed like a full minute.

I was more than a little jealous it was her body and not mine that was giving him this incredible pleasure and that I’d been effectively left out of the conclusion, and I actually felt a jolt of smug satisfaction when he finally slid out of her and a little stream of cum immediately followed. “Good job” I told him as I pulled his hips towards me and put his cum-soaked cock back into my mouth. “Did he cum in me?” I heard Trina ask behind me. What do you fucking think, Trina? I was obstructing her view of the action, but c’mon. “Mmmhmmm” I said sucking both of their cum of his semi-hard cock. I sort of hoped she’d freak out or cry or something but she said nothing else about it.

Tom reached up and undid his blindfold. He blinked a few times with a slightly puzzled look as he looked into my eyes as I slowly ran my lips up and down him. “I thought that was you” he said and gently ran his fingers through my hair, which fucking slayed me. He looked over at Trina and then down at the mess he’d made in her pussy, which was still tiny but noticeably stretched open and kind of smooshed with a tiny stream flowing from the depths. I felt his cock twitch in my mouth. “Who is that?” He asked me. “She’s your birthday present” I said inbetween slurps. “An intern.” His cock twitched again, noticeably hardening again now. “You got her for me?” He asked. “Mmhmmm. Did you like her?” “Mmhmmm” “Good.” He was almost fully hard again now.

Trina moved to stand up but Tom and I stopped her in unison. “I was just gonna clean-“ she started to say like an idiot. “I know. Wait.” I told her as I spread her legs back open to give Tom a clear view of what he’d done to his present.

Tom was already rock hard again and I raised myself up to sit next to Trina on the murder bench and leaned in and kissed his neck. “What’d your wife get you?” I whispered into his ear. “A bike” he whispered back. “Was my present better?” I asked him as I wrapped my legs around him and guided his cock into my own pussy. “Yes” he said. “She’s only a freshmen” I told him, finally getting to feel Sexy Tom inside of me. “Actually too young to be an intern”. He felt just as good as I’d always imagined. “I could tell” he said “She’s almost as tight as you” he added with a wink, which was a very nice thing to say and made me extra wet.

We continued on this way with our dirty talk objectifying Trina’s age and fetishizing infidelity as he fucked me good on hard on the table next to Trina. She was noticeably less interested in this second round between me and Tom but she was a good sport and sat there with her legs spread and pussy on display for our pleasure as a little puddle formed under her.

I asked Tom if he’d gotten a birthday fuck from his wife and he said they usually do at night but he might not be able to manage it today, and the thought of Tom turning his wife down on his birthday because of my gift sent me into an eye-rolling orgasm, way better than Trina’s dumb orgasm. I tried to continue the dirty talk after this, but Tom reached down and wet his fingers in Trina’s pussy and delivered the juices into my mouth, possibly just to shut me up, but I obediently slurped it down and then quit my yapping to allow him to enjoy my pussy in silence with his own thoughts. It was his birthday after all. Before long his breathing reached a climax and his arms clenched up and his cock throbbed inside me as it released its second load of the day into its second pussy. And it still might get a third pussy later. What a lucky cock.

When he was all good and finished he took a step back with a satisfied smile. He looked at us both, side by side on our backs, legs spread open, his handiwork evident in each of our pussies. He told us it might be the prettiest thing he’s ever seen and asked for a photo of us which of course I let him take. When he had his prize I told him he should get back to the party and he took his exit with a smile on his face. Me and Trina redressed, quickly went to the bathroom to clean up, then disappeared into the night. Mission successful.

So that was that! I’ll be honest, it was kind if a failure in terms of achieving my goal. It didn’t really feel one bit like Tom had fucked an intern with me. But we did have some great kinky sex and I got to watch him fuck a girl a fraction of his age, so maybe that’s all I wanted all along. Overall I have no complaints.

As a thank-you for her participation I bought Trina plan B. Hopefully she doesn’t have Tom’s baby. I should probably check in with her actually. Tom obviously never brought it up but he gives me knowing glances at work occasionally now. Sometimes even a smile. He’s a pro, he’s subtle about it, but I can tell he loved my gift. I like to imagine he looks at his photo every single day and thinks about his present so that has slightly cured my obsession. Maybe he fantasizes about me and Trina as much as I fantasized about him. Or maybe he lives such a James Bond lifestyle it was barely even memorable to him. Who knows!

Anyway thank you for reading!! Sorry it’s so long again!! I’ll really try to do a shorter one next time!! I love you all!