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About halfway through the day I texted Mr. Lewis to ask for his favorite movie. I wanted to make sure that our movie picks for that night were either on a streaming service that Mr. L. actually had, or that I'd bought them beforehand so we could watch them anyway.
The movies had been my idea. I was going to be going to college for psychology soon and I loved the idea of Chad, Daddy, and I all sharing a movie that we loved along with an explanation of why we loved it.
So, at around 6pm, that was what we did. I went first, to lead by example. I started by telling them both why The Princess Bride was my favorite movie of all time, and what I liked about it. Then we watched it. Then I talked with them about any parts that they loved or hated and I shared my thoughts on it.
I had a slightly difficult time getting the guys to pay attention to both the movie and my words since I'd changed back into my old highschool uniform once we'd gotten back to the house, and I'd made a point of saying that my panties were a mess so I was just going to go without. But, after 1-3, "my eyes are here Chad"'s, and 2-4, "The movie is on the T.V., not my breasts Daddy"'s, they eventually started to behave. A bit.
We were not 10 minutes into Chad's pick, Starship Troopers, when Mr. Lewis started to rag on it, hard. I scolded him a bit, and reminded him that the point wasn't to see it the way that he always had, but to appreciate what Chad saw in it. He grumbled at me, and watched the rest with his arms folded across his chest in an oddly defiant pose. But, at the end of the movie when Chad started gushing about all of his favorite parts, I excitedly backed him up and talked about how I liked some of them for totally different reasons.
Honestly, it was really cool to watch Mr. L. slowly come around, and kind of get into it with us. He still wasn't a fan or anything. But I felt like he genuinely got what we liked about it by the time we were done, and we'd admitted to getting why he didn't like the parts that annoyed him.
After that, it was time for his movie. It was some war movie that I'd never seen before called Heartbreak Hill, and before we got started I pointed out that we were out of drinks and asked Chad to make a quick run.
Mr. Lewis said we didn't need to because there were beers in the bottom drawer of the fridge, but that was followed by a slightly awkward moment where I reminded him and Chad and I were both 19, and neither one of us could legally drink yet.
He blushed a bit, but handed his Son some cash (who uses cash?!?) before giving him directions to a grocery store that Chad had been to 1,000 times before, and twice this trip. Chad gave him the confused "What gives Dad?" look that his instructions deserved, but if Mr. Lewis noticed, he didn't show it. Chad looked to me for back-up, but I just shrugged, and with a head shake directed at this Father, he was out the door and off to get us more drinks and snacks.
Once Chad was gone, I turned to Daddy, and, once again, if he noticed the look I was giving him, it didn't show. But that only made my grin bigger. "Does it bother you Daddy?" I asked, seemingly out of nowhere. He shook out of whatever thoughts had been distracting him, and looked up at me.
The mischievous grin from before was still there, and now he definitely noticed it. But I wasn't giving him any time to steel himself. So almost immediately after he asked me what I meant, I planted myself in Daddy's lap, and said, "My Age. I know some guys like it, while others are bothered by it. So, does it make you uncomfortable when I say that I'm 19, fresh out of highschool, or not even in college yet?" I gave him a second to think it over, even as I could feel him getting hard through his sweatpants.
Then I followed my question up with, "Or does it, maybe just a little bit, turn you on?" I was really asking. Some guys I could read like a book, but Mr. Lewis had this gruff exterior, and this amazing protectiveness of his Son that tended to hide his feelings for me behind a layer or two. Sometimes I could tell EXACTLY what he wanted to hear, and other times I didn't even know how things I'd already said had gone over.
I turned from sitting on him sideways, to straight up straddling him on the couch. I just wanted to be looking in his eyes when he answered me. But as he groaned and reached into his own pants to "adjust", he admitted, "It, just a little bit, turns me on." In my head I heard, "You turn me on", and it made me want to bounce on his cock in gratitude. But, Chad wouldn't be gone THAT long. Besides, today was supposed to be about teasing.
So, I posed one more question. "Daddy... a lot of the time, the games that Chad and I play, they don't, necessarily, conclude." In response the look that Mr. L. gave me told me he didn't quite understand what I was saying. So I went for a more direct approach.
"I like to tease. And I think that experiencing that pleasure, and touching those fantasies, is more important than just getting off. But a lot of people can't handle that. So, if you could touch me, and be touched by me, would you want to... even if you knew that it wouldn't end in climax; in you cumming?"
He didn't need long with that one, and after a second or two, he gave a firm nod. Mr. L. was one of those old guys who could do that. Just give a nod and like, it was the whole conversation. Over and done. But this was teasing, and, I was crazy fucking good at teasing. So I gave him one last chance to change his mind.
I reached down in between us and I gripped his cock after sending my hand down into his pants to find it. After I'd given him a few seconds to get his moan out and open his eyes again, I very clearly lifted my body a bit, and pointed the tip of him at my pussy. Then, with perfect communication skills, I asked, "Are you sure?"
He said yes. So I followed through, and within moments I was biting my lower lip and fighting back little whimpers of pleasure as Daddy's big cock slipped past my entrance and began to slide along my insides, spreading me open as it went. When I was firmly planted in his lap, his dick all the way inside of me, I needed a good minute before I could properly speak again.
Fuck but this was LEGIT my ultimate fantasy!
After I could think again, I leaned in to whisper into his ear. I made a little sniffing noise, then in a teasing whisper I said, "Uh oh Daddy...", I began. Then I gave a tiny roll of my hips before adding, "Have you been pumping some tight, young, pussy again?"
When I said it, Daddy involuntarily gave his hips a hard upward thrust that had me moaning and gripping whatever parts of him I could get my hands around. After that, I tried to be quiet. I didn't always succeed, but I tried. So basically, for the next 10-15 minutes, I just sat in his lap, and ever so gently, worked my way up and down the length of him in torturous slow motion.
By the time we heard Chad's truck pull back into the driveway, I was so turned on that I legit needed a minute just to catch my breath before I could even move away. Which was why Chad had time to come inside, call out to us, put most of the drinks and snacks away, AND put together a little kit to bring us before I finally managed to swing a leg over and pull Daddy's big cock out of the place that I most wanted it to be in!
Thankfully though, we didn't ruin the game! I managed to be back in my seat, and Daddy managed to pull a blanket over his still hard and still slick with my wetness dick, before Chad rounded the corner and asked what we'd been up to while he was away. In reply, I grinned at him and teased, "Sweetie, you weren't gone THAT long. Now, if you want to make a few more grocery runs..." At that, Chad gave chase, and I managed to keep out of his grip for a solid 30 seconds as he chased me around the living room laughing. But eventually, he got his hands on me, put me over his knee, and I found myself glancing over at Daddy watching us as Chad gave me the spanking I'd been asking for. As he did, my genuine laughter devolved into genuine moans.
Neither of the men seemed to mind though.
A few hours later, it was bedtime. Heartbreak Hill had actually been pretty good. I think Chad enjoyed it more than I had, but I had to admit it had been better than I thought it would be.
Just like the night before, I asked Daddy for permission to be loud, and to really enjoy getting to spend my second night as Chad's Fiance'. And just like the night before, Daddy had agreed to let us have loud, shake the walls sex. Of course, I took no small pleasure in knowing that he'd be listening in from down the hall.
As Chad and I got ready for bed in his room, I decided to poke a little more at his "Whore" fantasy, and I had to admit, it was way more elaborate than I'd been expecting. Like, my Mom loved the word, and I'd always liked it, but Chad was talking about roleplaying me being like, an actual prostitute. Which was very new for me, and only a big no-no in our community. We hung out with swingers and kinksters, but the kind of thing he was hinting at was strictly forbidden in all of our playgroups. The problem was, if you handed someone money and then had sex with them, the law got really iffy on whether or not that could be considered pretend. And the world had more than enough prudes that hated people who were comfortable in their sexuality. Especially if those people got together and had levels of fun that they themselves would never be able to even imagine!
Still, as Chad told me about his fantasy, an idea began to form in my mind. A terrible, wicked, sinful idea! So, you know, one of the good ones. But it would have to wait, because as Chad was getting undressed in the bathroom, I attacked him. I covered him with wicked little kisses, and once I got my mouth on his, we ended up knocking things over, breaking things, and pawing at one another as we fumbled towards the bed.
Once again, Chad, my beloved Fiance', who was hung like a fucking donkey, was keen to the idea of his Dad hearing how hard he was fucking me. So that night we actually damaged the wall with how hard we managed to bang the headboard into it. I screamed nice and loud, because Chad made damned sure that I had no choice in the matter, but also because I wanted Daddy to hear how good I was getting it just down the hallway.
Chad and I were at it for quite some time, and just like the previous night, once we were done and showered again, Chad was exhausted and halfway to sleep in a bed that was wayyyyyyy too small for just him. Let alone the both of us!
I slipped down the hallway to Daddy's room once more, but this time I could clearly see that he'd made good use of the lube and the tissue box that was on his nightstand. Maybe because of that, nothing really came of my being there. I slipped into bed alongside him, but Daddy just gave me some praise for my breakfast that morning, told me he enjoyed movie night with us, and gave me a very innocent kiss before saying "Goodnight babygirl". Which was SUPER unfair because when he called me stuff like that it was HUGE fucking turn on for me! Still, Chad had given me ideas. So, for right in that moment at least, I was content to be happy with what I'd already gotten, and in no time at all I joined both of my men in sleep.
The next morning I made my guys breakfast again, but, although I still teased them a bit in the process, this time there was no sex on the table. Literally or metaphorically. No, it was our last day there and with about a 3 hour drive ahead of us, the plan was to leave before noon. Or at least, that was Chad's plan. I had some plans of my own though. The problem was, I was slightly less sure of myself than usual. So I let Chad know that I wanted to talk to him about something before he finished packing the car.
We ended up in Chad's old room with the door closed. I let him know right away that I had a roleplay in mind, but I wanted to clear some stuff up with him. I hate when someone says, "we need to talk" and then leaves me freaking-out internally for 10 minutes instead of just spitting out whether or not we're cool, right at the fucking begining. So, I let Chad know what this was about right away.
Chad had been super into me calling myself a whore. We'd talked about it, and he had gone a step further and said that it was a roleplay that he'd like to explore. But, we hadn't actually done it yet, and with anything new, it's pretty easy to accidentally cross a line.
I didn't want to give too much away, but I also didn't really have a choice but to ask my questions. So, I framed the whole thing as, when we get back, if we go to a kink event, and the opportunity comes up, would you want to...
I started with; is the character me, or does he want me roleplaying as someone else, to get that degree of separation? Adorably, Chad actually blushed and looked away when he said that he wanted it to be me. So, naturally, I asked a bunch of questions that I knew the answers to just to tease him a bit, and get his temperature up. I asked him if I should wear some slutty prostitute clothes for the RP or just regular clothes. Then I asked him if I should keep my engagement ring on so that everyone involved knew that I was his fiance, or take them off and play it low key. I asked if he wanted to watch, or hear about it after the fact, and so on and so forth. Once I was pretty clear that I knew what I could and couldn't say, and what he did and didn't want to see (basically he wanted it as dirty as possible), I asked my last question.
First though, I told him I was done, and we should probably get going. He got up to go finish packing the car, and then to wait for me. I let him know that I'd dressed a little sexy for some last minute teasing during breakfast, but that I wanted to change into some comfy clothes for the ride home. Then, as if it was a last second, total "oops" moment, I did the obligatory forehead slap, and told him that I totally forgot to ask him something. Then, very, no pressure, nothing to worry about right now, I asked him if he thought that the list of people who didn't need to wear a condom with me should be expanded from just him, to him and his Dad. We'd had a similar talk about all of this yesterday when we were cruising around his old neighborhood, and I'd gotten the impression he was cool with it. But, there was a big fucking difference between getting the impression something was okay, and confirming it.
Chad didn't hesitate, he was totally okay with it. Now, in retrospect, him jumping to say he was fine with his Dad riding me raw might have had something to do with spending the 20 minutes leading up to that question talking about how badly Chad wanted to see me be a dirty, dirty, whore. LOL. But, I had my answers. So when Chad left his room and went out to finish packing the car, I set my real plan for that morning in motion.
To put it mildly, I planned on going out with a bang.
A good 30 to 40 minutes later, I was done with my outfit and my make-up. Just in time to, because as I was applying the final touches in the mirror, I got a text from Chad letting me know that we were all packed, and he was waiting for me in the car. So, I opened the door a crack, and called out for Daddy to please come to the door so I could talk to him.
When he got there, I spoke to him through the door as if I were naked and covering up, even if my red lips and dark eyeshadow 100% gave away that this was not the case. I told him that I would like to do one last roleplay with him before I go, and when he pointed out that "Chadwick" (snort!) was already in the car waiting for me, I explained that this was actually FOR Chad, and believe it or not, that was part of it.
It was a hard sell, at first. Mr. Lewis was still very new to roleplay and kink (although he was no fucking slouch in the bedroom!), so the idea that the part of this that was for Chad was, just him watching it, didn't quite click, right away. Still, as I told him the whole thing, Mr. L. kept adjusting his collar, and changing the way that he was standing; so, I was pretty sure he was liking what he heard.
For the last part of it, I told him that we would need two big bills. Like two fifties or two hundreds. I turned to go and get the money that I'd taken out yesterday when Chad and I were driving around, but Mr. L. cut in, telling me that he had that. Like... on him! CASH... I swear, I do not understand older Men sometimes. The odd need to have a large sum of paper money on him aside, Mr. L. seemed to understand the plan, and it didn't take a ton of convincing to get him to go along with it. Although, I did still give him the money that I withdrew instead of using his. After all, I'd be getting it back soon enough...
The last step in my plan was shooting my fiance' a quick text. I texted Chad the emoji that we used as code for: what you are about to see is roleplay, not real life. And I had a good bit of fun imagining him turning red at that. I could just see him sitting out there, as he went from wondering why I was taking so long, to wondering what naughty, sexy, game I'd come up with!
Once he knew it was part of an RP, I let him know that guys at work had made a mistake, and put the one way mirror the wrong way on our front door. Then I let him know that I would be running late because his boss, our boss, gave me a great idea for how I might earn some extra money to save up for our wedding. So he definitely shouldn't pick me up on time, since I was going to be, um, putting in some extra hours.This laid some fun groundwork because it implied that we worked in the same place, so Chad would be picturing his coworkers, people who knew. Also, Chad's boss was his Dad. So, I thought that bit was funny, but I hoped Chad just picked whichever idea he thought was hotter. Or better yet, I hoped he liked both!
I worried that he might not pick up on the mirror thing. Like, I'd be pretending that we couldn't see him but he could see us. But I also didn't want to over explain it. In the case that Chad wanted to picture like, a generic boss and not his Dad, I figured I wouldn't need to explain why I might be calling my boss/client, Daddy. 1st of all, let's be honest, a guy Daddy's age getting a prostitute my age would probably be super into it. Second of all though, Chad knew that it was a big kink of mine too. So it would have made total sense for me to do it, even if it wasn't Daddy. But god was it so fucking hot for me that it was!
A few minutes after my texts Daddy and I got into position and were ready to start this little show that I'd planned. Chad was still sitting in the car in the driveway, parked right in front of Mr. Lewis's kitchen door. The wooden door was wide open and out of sight, leaving only the glass door that kept the mosquitoes out, between the kitchen and the outside world. Chad had a great view of me as I rounded the corner. The heels on my boots clacked loudly on Daddy's kitchen floor as I made my way over to that glass door, and, pretending it was a mirror on my side, I took a moment to touch up my lipstick. Chad's favorite shade of, fuck-my-face, red. Naturally.
I had on a pair of black, knee-high hooker boots. Fishnet stockings that ran up into a short, tight, leather skirt, with a zipper down the side that made it oh so easy to remove. The top was a crop leather jacket that, like most tops, simply did not fit me right because of my breasts. The end result was a jacket that was meant to show off my midriff, but instead ended up showing off underboob as well. And, of course, I had the zipper down enough to offer up a generous length of cleavage line to boot. I still had my hair up in pigtails, but honestly this outfit was more, Me, than a lot of the stuff I'd worn that weekend. I normally trended pretty heavily towards slutty goth with my regular clothes. I just hadn't wanted to scare off Mr. L. on our first meeting. The end result was that my pigtails, despite being the same, now looked more in line with my bad girl persona, than my innocent teen one.
