Your sister loved the idea of us hooking up to spite you.

Transcript

I'd like to tell you all a story, and I think the way I'm going to approach that is simply to be me, here, present day, recounting the tale rather than trying to do some ill-equipped, very amateur acting. I'll simply tell you the story from where I sit, me and the microphone. So, I was kicking around a couple ideas of stories to share, and the one that I settled on is the story of the time I slept with a friend's sister, purely motivated by spite for a perceived wrong done to me by her brother, and I laid that out, plain as day, going into it, and we'll call her Lacey.

Lacey was mature and confident and exuded such sexual prowess beyond her years and age that she was able to hear that, not be offended by it, clap right back with an ulterior motive of her own that she was requesting my assistance and lending of support in achieving a certain vibe and effect to, and the whole thing has been etched in my memory ever since as a uniquely hot, nearly one-off encounter. We had the one encounter and then couldn't quite coordinate, but not for lack of expressed interest by both of us, and then a number of years later we did reconvene. So, yeah, let me take it from the top.

So, for propriety's sake, let's say that we were community college students. You can perhaps infer the actual chronological period of my life during which this story took place, but for our purposes here today, everyone is above 18 years old and we're community college students. Your boy Benny Ruthless found his employ at the time, among other things, selling marijuana.

It was the late 90s, early aughts. It was a time ago when, you know, that wasn't sold at the Apple Store looking dispo, but still was a veritable cash crop to be reckoned with. I made the ill-judged decision to sell an eighth of my fine cannabis flower to Tim.

Tim was a little bit loose-lipped, to say the least, and my whole burgeoning empire crumbled before my eyes quite rapidly at that point. Utter shock and disbelief. How could I have been so cataclysmically stupid as to sell to Tim, who would go ahead and snitch me out?

So, you know, my juvenile delinquent mindset ran deep at the time, and a message needed to be sent that this type of snitching would not be tolerated, and so I picked an altercation with Tim, which ended in really a veritable draw, and us being, you know, pulled apart, and additional days being tacked on to my pending suspension from school. So, you know, it was not the loud and clear resounding rebuke to the tattletailing ethos that had been desired, so I decided I would need to get creative. Hmm, how might I go about sending a clear and resounding message to our friend Tim that he had erred in his ways that would deter those who might otherwise seek to follow suit?

Hmm, I lamented and anguished and pondered on the question, and when it came to me, I couldn't believe I hadn't thought of it earlier. Tim's younger sister very openly had a massive crush on me, was really quite infatuated with yours truly, something that she barely sought to conceal anytime I had been at Tim's house. She lingered in the adjacent room and, you know, just made every effort to be in contact and close to me, and in recent years had started to look pretty damn good, if I didn't say so myself.

You know, there was the age difference, and your boy Benny Ruthless has naturally gravitated towards women a few years older than him, so that was outside of our natural proclivities, but, you know, as I also like to say, variety is the spice of life. So the thought came crashing down and I knew that this was the plan. Tim had the quintessential protective older brother vibes, Lacey had the indispensable, slutty, into me vibes.

See, you know, if he wouldn't, if he had been someone who wouldn't even be phased by that, who would just roll his eyes and say, well, it's none of my business who my sister sleeps with, then it might not be the most effective retaliation, but he was very antiquated in his views about this and viewed it as something of a personal affront, the idea that somebody should uh, yeah, make a conquest over his sister or whatever bizarre patriarchal dated thinking was going on there. You know, I honestly just can't relate, but I first wanted to clarify just one thing. I didn't quite feel right with the possibility that Miss Lacey was a virgin and would be having sex for the first time under such pretense.

So I asked around, I asked a mutual friend of ours, the, uh, who the luscious and incredibly sexy Kate Randy, who, you know, deserves a story of her own, uh, confirmed for me with great excitement that no, of course, Lacey was not a virgin and I should, uh, feel a green light across possible concerns to go for it. Yeah. And this coming from a mutual friend that I had had repeated flings with really, so having her blessing and actually her excitement, uh, really parked up my enthusiasm for the, the whole undertaking.

Cause she really was, was our friend. Kate Randy was very excited to hear that I was going to actively pursue sleeping with Lacey, whatever the pretense may be. I believe she said a good handful of times that she wanted it recorded and posted on the internet or live streamed out, or could she just sit across the room and watch and, you know, in retrospect, I wish I had taken her up on that because, yeah, well, hindsight is 20, 20, but so equipped with this information, I sought out to make my desire known to miss Lacey.

And I was operating from the assumption here that, you know, she had been into me and sort of vying for my attention for years, really my hope in so many words was that simply revealing my state of willingness and interest would be enough to galvanize things going forward. And in essence, that's exactly what happened. I'm dating myself a bit here, but I, uh, send her a message on MySpace.

Let's see, that was a Tuesday night. I messaged her on MySpace on Tuesday night and I wanted to get out in front and establish the ulterior motive because my overall sense was that miss Lacey had a certain sexual prowess and maturity about her where she would, which, you know, is a bit in conflict with my previous is a bit in conflict with my previous concern that perhaps she, uh, was completely inexperienced, but, you know, I think that that was more just a just in case given we were, but, you know, early community college students. So having had that far-fetched doubt quelled, I had a strong sense that miss Lacey was sexually confident and clear and nonjudgmental nonjudgmental in a way that would transform this quote ulterior motive into a raunchy sort of window dressing around the whole vibe of the encounter.

I thought, you know, she probably liked some dirty talk and liked some role play, however, mild or insinuated. So I opened up with a message saying, your brother's really something. He's on my shit list for sure.

So decidedly platonic message, they didn't get along very well. So I knew that that would land from there. I'm going to say it was all of six more messages exchanged and 45 minutes passed before miss Lacey was on her way over to my parents' house where I lived at the time where we would fuck in their basement, less than 10 messages, less than an hour from the first time we interacted individually, privately.

God, I love a fucking confident slut like that. That's willing to act on their desires and knows what they want and seizes the opportunity. She very much picked up that I wanted a spite against her brother, fucking his sister, degrading and humiliating him kind of vibe.

And she was very turned on by that. And in turn requested of me that we could taunt her boyfriend at the next school over, who in her words, wasn't hitting it right. And I of course was more than happy to oblige and incorporate that vibe in.

I honestly was almost a little intimidated by how confidently she came right back at me. She sent me, among the small handful of messages exchanged before she made her way over, a picture of her in a bra and panties, a picture of her topless, and then a picture of her spreading her legs and fingering herself. It was a bit on the blurry side given we were working with flip phones, but the fact that she had these ready to go and not only that, but made a rather astute observation that most of the women I dated at the time were of a particular body type that was a departure from hers.

They mostly had smaller tits than our dear Lacey did, whose breasts are rather large and incredible in every fucking sense of the word. She came back at me so confidently saying, I noticed that you gravitate towards chicks with small tits. You're not intimidated by my girls, are you? I should have called them her girls.

And inside, I thought to myself, I'm not intimidated, but goddamn, you do have some big titties, Lacey. I can't wait to play with them and bounce them around. So yeah, I was flustered.

You know, you don't expect all that self-assurance coming back at you from a young woman who a few years earlier was your friend's shy little sister, but goddamn it, it's hot when it does come back. So she came right back at me, sending me these pictures and telling me, yeah, you're not used to a woman with big tits like these, huh? And then she said to me, my boyfriend says that they can't be titty fucked without covering up a whole dick.

He said, it's not just him, but nobody would come out the other end, but I just really want a picture of somebody sliding their cock in between my cleavage and the head of their dick poking out and me reaching for it with my tongue. What you working with over there? Do you think that's something you might be able to accomplish? I looked at her photo again and pictured in my mind the glorious fucking rack that I saw every day around campus.

And I was not so sure, but of course I erred on the side of maintaining some mystery and interest and said, why don't you get your sexy ass over here and we'll find out. I can't wait to titty fuck you. You're going to feel this fucking cock slide in between those fucking girls real soon here.

I'm going to fucking spit in between the fucking cleavage. You're going to see me fucking mounting your fucking chest and a fucking thin line of spit dripping, landing perfectly in the path of the strokes of my fucking cock as I fuck between those titties and you squeeze them together so nice. And the.