The Jenna Arrangement Pt 29

"I'm sorry, Michelle wants me to do what exactly?"

When Jenna video called me, I was of course excited to see her. But nothing could have prepared me for the bombshell she dropped.

"She wants your help in making a custom video for one of her Only Fans clients," Jenna repeated.

I was flabbergasted. "Help? What do you mean, help? Help how? Because I'm assuming you mean..."

"Look," Jenna cut me off, her amusement at my reaction obvious, "she's right here. Why don't I just let her explain?"

Before I could object, Jenna handed the phone over to her roommate. "Hey, Tommy, good to see you. How was your summer?"

"Fine. Good." I wasn't going to let her attempt at small talk disarm me. "Now how about you tell me what this is all about."

Her face turned only slightly more serious. "Okay fine, right to it then. So I've had a request from a client, a very affluent client. He wants a custom video. Even sent me a script for it. He's willing to pay quite a bit of money for me to record it. And I could use the payday.

"Only problem is, it would require a... male partner. And I don't have a boyfriend currently. So I thought of you."

"Hold on," I gasped, "are you seriously suggesting..."

"Slow down," Michelle interrupted. "No. I'm not asking you to fuck me. I wouldn't have asked that even if you weren't already involved with both Jenna and Trish..."

"Hey, Tommy!" Trish's voice came from somewhere offscreen.

"Hey, Trish," I responded. "You're in on whatever this is too, huh? Guess that shouldn't surprise me."

"Yeah, I'm..." Trish's voice was silenced by a glare from Michelle. "Trish! Geez, let me finish, will'ya?"

Turning back to her phone screen, Michelle continued. "So the video this guy wants is a JOE. I'm assuming you're familiar with what that is?"

"Jerk Off Encouragement. Yeah, I'm... familiar. But aren't most of those just videos where the woman performs solo?"

"Normally, sure," Michelle acknowledged. "But like I said, he wants something special. He wants an actual dick in the frame, not just me performing to some rubber penis."

"And..." Michelle took a deep breath here, and even through the video screen I was pretty sure she blushed. ".... he wants a facial finish."

"Ah." I really couldn't think of a more verbal response. Mental images flashing through my brain of coating Michelle's lovely face with my cum made thinking rationally rather difficult at the moment.

Jenna leaned back into frame. "We've already discussed the details hun, and I'm cool with it. She's not gonna blow you, or even jerk you off. She's gonna be role playing, dirty talking, touching herself. You'll just be watching and masturbating. You know, like you do to her videos already." Jenna flashed her adorable smirk and wink combo, and now I was the one blushing. "Just this time, you get to finish on her in person."

My silence held as I contemplated Michelle's wild offer. Sure, I'd fantasized about her. Especially since she'd given me access to her Only Fans profile. But I was more than happy and satisfied with my relationship with Jenna, and of course we also still had Trish joining us on occasion, although it had been awhile there.

The closest I'd come to seeing Michelle naked in person was at Jenna's birthday party, when I'd played Nude Butler to a room full of lingerie-clad young women. Now I was being offered the opportunity to not only see her fully nude up close and personal, but to openly masturbate to her as she performed.

I suppose I wasn't all too surprised that Jenna had already agreed to this. She knew me very well, including my kinks. It was those kinks that had brought us together, after all.

Still, I had a few questions. "Why me? I'm sure you could find a willing single guy on campus."

"That's not as easy as you'd think," Michelle said. "Sure, I could find a willing guy. But he'd certainly want to do more than just jerk off on me. That's if I could even convince him to perform on camera. A lot of guys are squeamish about that."

I couldn't help but wonder how squeamish I'd wind up being; while Jenna and I had made a few personal recordings, we'd never considered putting any of it online, even for her own OF page.

"Besides," Michelle continued, "believe it or not, I'm not into random guys. Especially for something like this. I need someone I can trust. I know we don't know each other that well. But I trust Jenna. And Jenna trusts you."

"Fair enough," I acknowledged. "And I appreciate that trust. Although I suppose we'll have to have a little talk about boundaries and details at some point, just so we're all on the same page here. I don't want any misunderstandings or misgivings later."

"Agreed," said Jenna. "I'm not working this weekend. So I'll be here for it. Michelle agreed she'd prefer me to be present."

"Hey! What about me?" Trish chimed in again. "I wanna watch too ya know!"

Jenna and Michelle both laughed. "Of course," said Michelle. "The more the merrier. Besides, I could use you as an extra cameraman. You can record some side angles."

"Wait, back up a second," I jumped in. "This weekend? That's when you wanna, um, shoot this thing?"

"Yeah, why?" Michelle smirked. "You had other plans?"

"No, just..."

"Good," said Jenna. "So what do you think, cowboy? You're in, right? Come on, it'll be fun, I promise."

I pretended to think it over for a moment. But seriously, what idiot would turn this down, right?

"Okay, I'm in."

"Great," said Michelle. "Thanks, Tommy. I've had a couple of personal things come up, and I could really use the money. So I appreciate you... cumming to my rescue here."

I had to chuckle. "Couldn't resist the pun, could you?"

Michelle just smiled and shrugged. "Oh, and one last thing. My client really wants a big, messy facial. So if you could, you know, save it up over the next several days, I'd really appreciate it."

The next several DAYS? My face must have given away this thought, because Jenna couldn't suppress her giggle. "Think of it this way; Trish and I will both be here. Watching. And we're already really missing you, hun. So we're gonna want you after. Like, really badly. So the more you save up your stamina for this weekend, the better. Trust me."

I was hard already just imagining it. "I'll... do my best."

"Good boy." The sultry tone of Jenna's voice didn't help my erection issue at all. I was definitely going to need a cold shower after this call ended.

"Great! Then it's settled," said Michelle. "See you Saturday, Tommy."

💡 📷 🎬

It was the longest week of my life. Not helped at all by the fact that Jenna, Trish AND Michelle were constantly texting me selfies. Not nudes, just cute, sexy poses in tight, revealing outfits. Attached to those photos were little notes:

"Thinking of you. ❤️"

"Can't wait til this weekend. 🤗"

"See you soon. 😉" etc.

It made it very difficult to keep my mind off it.

By the time Saturday came around, I was a frustrated mess. Fortunately the girls had told me to come over early. Jenna hugged me at the door; a simple, innocent hug that had me wanting to tackle her to the floor and take her.

Instead, I managed to maintain my composure as I greeted the others. It was then that I noticed there was one more person there.

"You remember Carrie, right?" Jenna asked.

I tried to mask my surprise. I had forgotten they'd made arrangements for her to room with them this year. "Of course. We met this summer. How's your dad?"

"Great, thanks," Carrie beamed. "He's actually on his way over with his new girlfriend, they're taking me out for the day. So you'll get to say hi when he gets here."

"I'm looking forward to that." Inwardly, I sighed with relief. I had no idea how much Carrie knew about anything when it came to the full extent of my relationship with Jenna and Trish, let alone whether she was aware both Jenna and Michelle sold sex content on Only Fans. And I certainly had no clue if she would approve of what we'd be doing with Michelle later. So I was thankful she wasn't going to be around for it. As interesting as the idea of including her might be, I was already nervous enough already.

The time ticked by slowly as we all socialized and caught up. The girls, as usual, did most of the talking, filling me in on their classes, etc.

Eventually Carrie's father Bill showed up, and after catching up with him briefly, and meeting his lovely girlfriend, they departed, leaving us free to finally get down to business.

Michelle didn't hesitate. "So everything is set up in my room, if you all are ready."

"Hell yeah!" Trish cheered. Jumping up from the couch, she started following Michelle to the bedroom.

Jenna remained seated by me. "You two go ahead and set up. We'll be there in a minute."

When they were gone, Jenna turned to me. "So I just wanted a minute alone, obviously. Mainly just to assure you again I'm fine with this. And to see if you had any questions or reservations."

"I don't have any reservations as long as I know you're good, darlin'. But I suppose I do want to know what my boundaries are here. I know I'm supposed to just jerk off on her. But what about any possible physical contact? Am I supposed to touch her? Am I ALLOWED to touch her? What about her touching me, or..."

Jenna took my hand and smiled. "I understand your concerns. And I really appreciate them. One of many reasons I love you." Leaning in, she gave me a quick yet affectionate kiss. "I've been thinking it over myself the past few days, wondering how far I'm comfortable with. So I talked it over with Michelle. And here's what we both agreed on.

"She's got a script to act out. She's going to encourage you to jerk while watching her, then get up close and personal so you can cum on her face.

"She's not going to blow you.

But I'm okay if there's some... contact, here and there. If she wants to touch or tease a little or something.

"I've read the script. The idea is she's intentionally teasing; a Look But Can't Touch scenario. So I don't think she'll be asking you to touch her directly."

"Okay." I nodded. "Certainly wasn't planning on touching her without your permission, or hers, obviously."

Standing, Jenna guided me up with her. She slipped into my arms. "Just relax," she said, "I want this to be fun for you. For all of us."

After another, more prolonged kiss, I followed her to the bedroom.

What I found quickened my already racing pulse. Michelle had stripped down a tight pink sports bra and matching thong panties. She smiled when she saw my reaction. "Oh, don't look so surprised. You've seen me like this before."

"True," I chuckled. "But it's been awhile."

"So here's the script," Michelle said, handing me a stack of papers. "Don't worry, you don't have any lines. I just wanted to go over it with you so you'd know what to expect. It gets a little... weird. He originally wanted a Daddy / Daughter thing, but I find those a little creepy, so we settled on the 'Mom's Boyfriend Walks In On Me' scenario.

"It's a little all over the place; he wants me to be mean, almost dominating, but also wants me to call him 'Papi.' And to use his name once in a while too, so don't get confused if I call you Jimmy, okay?"

"Got it," I smirked. I suppose I couldn't really fault the guy the 'Papi' thing; Jenna had called me Daddy several times during some of our role playing, and, being honest, it turned me on too.

I read over the script quickly while the girls adjusted the lighting and cameras. Michelle was well prepared, even had a laptop set up as a monitor screen so we could see the shots as they were being filmed.

She also had two cameras going. Jenna would be manning the main digital camera, and after the intro would be standing on a stepladder behind me, filming over my shoulder to catch the action.

Trish would be using Michelle's cellphone and shooting from alternate angles that Michelle could edit in later. It was quite the production, honestly.

Once everything was set, it was time to begin. "Don't worry about mistakes," Michelle instructed. "If I flub a line or something goes wrong, just keep filming. I can fix it in editing."

With that, we took our positions. For me that meant stepping out of the room for the moment. Jenna followed me. Trish moved off to the far side of the room, out of the shot.

For Michelle, it meant laying on her bed, pretending to be asleep.

"Okay," Jenna called out, "Hitting record now. Action in 3...2...1. Go."

With that, Jenna moved to the door. We'd left it open a crack and Jenna was filming through it. It was a standard tactic. The idea was that it was from the viewers point of view, spying inside the room.

Michelle lay motionless on the bed, slightly to her side, her body positioned in a way to highlight her long legs and of course her round ass. I watched over Jenna's shoulder as she zoomed in, slowly moving the camera up and down Michelle's body.

Michelle stirred, parting her legs, giving the camera, and me, a stunning view of her pussy, exposed save for the string of her thong running up the middle. She already looked slightly wet.

Another shift and now she was on her back, legs fully parted. I thought back to the tantalizing glimpses of her plump mound and puffy vulva during Jenna's birthday party. This was a much more blatant display. Of course, I'd also seen her pussy on her Only Fans videos, but there is nothing quite like seeing one live and in person. I longed to get closer to it, but I wasn't counting on that. I had to remember this display wasn't just for my benefit, that essentially I was just an actor in a role. Not even that, really, more like a stand in.

Still, it was more than enough to get the blood flowing.

Jenna moved to center herself near the foot of the bed as Michelle began slowly caressing her almost nude body.

One hand found her breasts, massaging them first over, then under the snug sports bra. Her other hand traveled down between her legs, teasing herself with the lightest of caresses before using her fingers to part her dark folds, exposing the lovely pink within.

Michelle made sure to keep her eyes closed, as if she were still in some half asleep dream state, as she continued her slow, sensual explorations. Jenna and Trish were both filming, although by the looks of them, they were becoming just as aroused by the performance as I was.

Finally Michelle sat up, opening her eyes. "Okay I think that's enough of that. Now, Tommy, move into position and Jenna, get behind him and shoot from there. Trish, just shoot from wherever, be creative, but try to stay out of Jenna's shot."

We all quickly found our positions and, when ready, Michelle again directed. "Now Tommy, go ahead and take out your cock. Jenna, make sure you frame it to get both me and his dick in the shot."

I unzipped as instructed, my cock springing free gratefully. Michelle couldn't help but smirk knowingly before resuming her position. "Everyone ready? Okay action in 3...2...1... go."

Michelle resumed masturbating as I began to stroke myself. After roughly thirty seconds or so, Michelle's eyes flew open and she began her performance.

Sitting up on the bed, she did an intentionally bad job of trying to cover herself. "Jimmy! What are you doing??? You can't just barge into my room like this! How long have you been standing there? And..."

Here she paused, her eyes growing almost comically huge. "... and why is your cock out???"

As the script called for, I pretended to try and cover my erection as Michelle continued her lines. "Oh, don't try and hide it, I saw you! Jerking your cock to me while I was touching myself! Can't a girl get any privacy? Fucking creep! Just because you're dating my mom doesn't give you the right to perv on me! Now get out!"

With the way Jenna was positioned on the step stool just behind me, I couldn't move from position. So instead Jenna swung the camera towards the door, turning back when Michelle called out, "No, wait!"

Sitting back on the bed, her hands no longer covered herself. Instead she parted her legs wide, again exposing her still slick pussy. "You wanna watch? Fine, you can stay and watch. On one condition: You talk Mom into letting me go on that trip for Spring Break. And YOU pay for it."

Michelle paused as if listening to a reply, then continued. "Oh come on, I know you have money. And I'm sure you can talk Mom into it. You better; otherwise I'll tell her what a fucking pervert you are."

Again she paused, then smiled wickedly. "Good boy. Thought you'd see it my way."

With that she began caressing herself, her hands sliding all over her ripe, toned body. "Go ahead then. Jerk your cock. Jerk it to this young, tight Filipino body. These firm, perky tits. This flat, firm belly. These long, sexy legs."

Scooting to the edge of the bed, Michelle once again opened her legs wide. "But I bet what you REALLY wanna see is this tight, wet pussy, right? Well go ahead then, perv. Get down here and take a closer look."

I hesitated, unsure what to do. Then Michelle broke character. "Okay Trish, get over her and film some closeups. Tommy, Jenna, just stay where you are for a minute."

Trish knelt between me and Michelle, partially blocking my view as Michelle got back on script. "Look how wet I am, how excited. I bet you wanna taste me, don't you? Well you can't, perv. But go ahead and look. Better yet, take a big whiff. I bet you love how my pussy smells, don't you? I bet you've been sneaking in here and stealing my panties from the laundry basket, haven't you?"

I couldn't see, but the slippery wet sounds now filling the small room clued me in that Michelle was finger fucking herself.

Suddenly I felt a hand on my cock that was not my own. Jenna had stepped down off the ladder and had reached around from behind me. I turned my head to offer a silent question. She just offered me that devil may care smile as her hand squeezed my throbbing shaft.

"Jenna! Don't you dare!" We turned as one to see Michelle now sitting up, glaring at us. "If you make him cum before he's supposed to I will seriously kick both your asses."

"Sorry," Jenna and I replied in unison. "Couldn't help myself," Jenna added.

"Whatever," Michelle sighed. "Tell you what; get over here, both of you. Time for the next part."

I gulped audibly, knowing what was coming. I just hoped I'd be able to contain myself.

Michelle lay back on the bed. Kicking off my now cumbersome pants and boxers, I moved between her parted legs, stopping just short of her opening.

Jenna stood beside me and, after throwing me an assuring glance, began to film.

My worries about things possibly going beyond the boundaries were quickly quelled when Michelle barked," Okay, back into character. Just remember, keep that thing out of me and don't you dare fucking cum yet."

"Gotcha," I managed.

"Okay, action in 3...2...1... Oh that's it, get in close, so close to my little pussy. You wanna stick it in me, don't you, Jimmy? Oh I bet you're just aching to fill up my tiny little hole with that big, huge cock of yours. To shove that big, throbbing..."

Michelle suddenly burst into a fit of laughter. "Oh fuck me, I hate this shit sometimes! This dialog is... just so...stupid!"

"Hey, it's porn, right?" I couldn't help but grin. "It's supposed to be cheesy and over the top."

Michelle finally managed to contain herself. "True. You guys and your insecurities about your dick size, though. Always need us telling you how BIG and THICK it is."

"Tommy doesn't need me to tell him that," Jenna giggled."He's got nothing to be insecure about."

"That is true," Michelle replied, one eyebrow arched as her gaze fixed directly on my still raging erection. "And part of me wishes... no, nevermind, forget it. Let's keep going."

And so we did; Michelle and I resuming our positions while Jenna and Trish filmed. Once again my cock was dangerously close to Michelle's pussy as we masturbated together.