The Jenna Arrangement Pt. 10

ALL CHARACTERS ARE AT LEAST 18 YEARS OF AGE OR OLDER

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The week dragged by. Jenna was busy with classes and shifts at the diner, while my job kept me occupied as well.

When I wasn't working, I found myself spending extra time at the gym. Some nights I did my usual routine, others I just took advantage of the pool, hottub, and / or tanning booth. I hadn't been working out all that long really, only a few months before I met Jenna, but was finally starting to see some results beyond my first few pounds of initial weight loss.

Wednesday morning I texted her to wish her luck on her art project. About an hour later she replied, "Thanks. Will do.💋"

I was just sitting down to dinner Wednesday night when Jenna called.

She filled me in excitedly. "I can't talk long, gotta get ready for my shift at the diner, but I wanted to let you know the art project went great! I think Trish and I both did really well on it!"

"Awesome. Great job. I'm glad it went well."

"Thanks again for your help," she said. "I know things got...out of hand...later, but you really did help us both so much."

"You're welcome," I replied, "I'm happy it helped."

There was an awkward silence for a few moments before Jenna spoke again. "I'm off Friday night. Can we get together and talk?"

"I'd like that," I answered genuinely.

I wasn't comfortable with the idea of getting together at Jenna's place any time soon in case I ran into her roommate again, so we made plans for me to pick her up and find somewhere quiet to eat and talk.

When I pulled up in front of her dorm Friday night, I texted Jenna to let her know I'd arrived. I was too afraid to knock in case Michelle was there.

Jenna texted back: "Still getting ready. Michelle is here. She'd like to talk to you. Come to the door, she'll let you in. It's okay, promise. 💋 "

I practiced my breathing exercises for a few moments to ease my tension, then made my way to the door.

It opened before I could knock. Michelle was standing there. Thankfully, she was smiling.

"Tom, right? Come on in." Noticing my hesitation, she laughed. "Don't worry, I won't bite, I promise."

Once inside, Michelle invited me to sit. I didn't want to sit on the couch, afraid it would stir up memories of the last time she saw me seated there, so I opted for one of the single chairs. Michelle took the other chair across from me.

"So I wanted to apologize for the way I treated you that night," she began. "Jenna explained everything to me, and assured me you had nothing to do with it. We had a little chat about rules and boundaries when it comes to male guests in the house, and we're cool now. Sorry if I came off as a psycho bitch."

"Thank you," I said gratefully, "but you have nothing to apologize for. Your reaction was completely understandable given the circumstances. Jenna and I are going to have our own chat about rules and boundaries tonight."

Michelle looked at me solemnly. "Good."

She looked like she wanted to say more but was stopping herself. I'm sure it was probably a question about how I'd met Jenna, or the age difference, or both. I could read it in her eyes.

But she didn't ask. Instead she stood. "I'll go check on Jenna."

I'm sure you're probably wondering at this point, so I suppose I'll just confess and say that yes, I did check her out as she walked away.

Michelle was tall, with legs that seemed to go on forever. She appeared to be of Filipino descent, with long, straight black hair that fell halfway down her back.

Her hips and ass were incredibly curvy in her skin tight yoga pants. I tried not to stare too long, but my will was weak and my gaze never left her until she disappeared down the hall.

"Put your eyes back in your head, old man," I chided myself silently. "Last thing you need is to be caught staring at her. By either of them."

Jenna came out a few minutes later, and as usual, she was stunning.

Her outfit was adorable in its simplicity; form fitting, high waisted denim shorts with brass buttons that ran down each side of the oversized pockets, and a black, sleeveless top with a loose fitting, lacy turtle neck.

Her hair was swept back and held in place with a shiny rainbow colored butterfly clip.

Her black, low heeled pumps added a few inches to her height, with gold buckled straps that criss crossed around her ankles.

Her make-up was similar to what she'd worn that night after our date at the lake, and as her emerald eyes met mine, she smiled hopefully.

I stood to greet her. "Hey. Wow! You look...great," I stammered nervously.

I was debating on whether to go in for a hug or kiss when Michelle came up behind her. I decided to save any displays of affection for later.

"Thank you," said Jenna. She looked nervous and self conscious, as if not sure how to act at the moment either.

Michelle looked at the two of us just standing there shuffling on our feet and laughed. "Oh go on, hug him," she prodded Jenna, "you know you want to."

Jenna hesitated, looking at me, still unsure.

I stilled her fears by taking her in my arms and giving her an affectionate (but very chaste) kiss, then hugged her close. "It's good to see you," I said softly.

I could feel Jenna's tension melt away in my arms. She hugged back, then pulled away.

"Okay, okay," said Michelle, "you kids get going, have fun." There was a notable amount of sarcasm in her voice as she said it, and I saw her dark brown eyes glance in my direction. But her face was full of good natured humor, so I tried not to take it personally.

Just as we reached the door, Michelle called out, "Wait. Just one more thing."

We turned to face her. "I don't want you to think you're not welcome here," said Michelle, addressing me. "You are. Any time. I'm usually at my boyfriends on Friday and Saturday nights, if you prefer some...privacy."

To Jenna, she said, "Just make sure you let me know if he's coming over when I'm here. If I'm at Dave's, text me. I'll make sure to call or text you if I'm coming home. If all you're doing is hanging out, I don't mind coming home to that."

She paused, then grinned slyly. "But if anything ELSE is hanging out, just do me a favor and limit that to your bedroom."

I flushed furiously and pretended there was something incredibly interesting on my shoes while Jenna blushed and nodded. "Will, do, I promise."

I was glad to be out of there.

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We tried three different restaurants, all of them packed on a Friday night, before Jenna suggested getting some Chinese takeout and going back to my place.

After an internal debate about just how clean my apartment was or was not, I decided to risk it and agreed. We needed to have a serious talk, and it would best be done in private anyway.

We caught up with general chit chat as we ate, and Jenna seemed in good spirits.

When we finished, Jenna spent some time admiring my assortment of Star Wars and Marvel stuff. "You've got quite a collection," she said as her eyes roamed my shelves and displays.

"Thanks," I said. "I was hoping you didn't mind dating a middle aged geek."

"Haven't you heard?" Jenna grinned. "Geeks are cool now."

We sat on the couch, sipping on some ice tea. I'd considered having a beer, but wanted to remain clear headed for the conversation ahead.

"So we need to talk about what happened," I started, "but before we do, I just want you to know: I'm not angry. At least, not anymore. And I don't want you to feel like you're on trial here or anything. I just want to be able to discuss things openly and most importantly, honestly, okay?"

Jenna nodded, offering a tight smile.

"So I guess I wanna start with what made you get Trish involved, and just how involved was she?"

Jenna lowered her head as if ashamed, and was about to speak when I stopped her. Lifting her chin, I turned her face towards mine. "Hey, you don't have to feel embarrassed or guilty. We're done with that, okay? I just want to talk about it."

Her smile brightened at that, and she looked more relaxed.

"Okay," she began.

"It really did just start as a way to help her practice. She called me after you left that night after the movie, and she was actually the one who suggested it. I was surprised, but the more I thought about it, the more I figured it could work both ways. It would be a legitimate way to help Trish, but also maybe a fun way for you to, you know, indulge your fantasy a bit. So I told her yes."

I nodded. "I appreciate your intentions. But you really should have asked me first."

"I know," Jenna conceded. "But I honestly didn't start out with intentions to, well, tease you, get you worked up. Although we did talk about the possibility. That you might get an erection, how we'd handle it, you know.

"We were both surprised you DIDN'T get hard, actually. Trish even commented on it when you took that bathroom break. She seemed almost disappointed.

"I guess that's when I first got the idea to try and tease you into it. I was kinda warming to the idea of, well, showing you off. Plus, the wine was kicking in," she grinned sheepishly.

I took this all in carefully. I suppose I understood it. Jenna knew of my...fetish? fantasy?...of being naked and aroused in front of a woman, how I'd talked about it being liberating and freeing, and assumed I'd be thrilled to be able to do it around Trish.

"Was Trish aware you were gonna tease me like that? Try and get me going?" I asked.

"Well, yeah. She kinda suggested it. Well more like hinted around at it. After dinner, when you were in the bathroom again, she said something like 'I'm surprised you haven't gotten his motor running yet.' That's when I decided to...take off my panties." Jenna blushed heavily.

I had to try hard, really hard, not to think back on that moment.

"So Trish was consenting, and even goading things along a bit. I suppose I'm okay with that. She seemed to be having fun with it, and if I'm being honest, so was I. So I can't really be mad at that, but still, in the future we should at least talk about it first, so I'm aware everything is consenting, and what the boundaries are."

Jenna nodded in agreement. "Of course. I suppose I should tell you this as well: Trish and I...well...she used to come over and watch guys on Omegle with me sometimes. We'd get tipsy or smoke some weed and tease the guys mercilessly all night. So it wasn't exactly her first time watching a naked guy get a boner."

My eyes went wide. "Really?"

"Yeah. We always stayed dressed of course, but sometimes we'd...make out, on cam. Not our whole faces, but enough that the guys could figure out what was going on." Jenna was still blushing, but didn't seem embarrassed to admit all this. "We even felt each other up a few times. Over the clothes," she added quickly.

Jenna must have seen something in my face, because she giggled softly. "Hey, don't get any ideas, cowboy. We were just goofing around."

I gave a "Who, me?" shrug, and we both laughed.

"Well I'm glad that Trish was aware enough of what was going on and had agreed to participate. And if I'm being honest, I wouldn't be against doing something like that again, only if you're okay with it. And in a more controlled environment of course."

I paused for a moment, then continued. "Now let's talk about Michelle. I don't wanna harp on this too much, and I'm glad you patched things up with her.

"But I want to be clear that's not what I'm looking for. I'm not some pervert looking to flash unsuspecting women. I know in porn the women swoon when they walk in on some guy jerking off, but that's not reality. Reality is what happened that night, or worse, having the cops called on you.

"I appreciate that you've embraced my little fantasy, but I just want to make it very clear I'm not interested or excited by the idea of exposing myself to a woman without her consent, okay?"

"I understand, completely," said Jenna. "The more I thought about it, the more horrible I felt. Because I knew if the roles were reversed, and I was the one naked and exposed to someone unwillingly, I'd be more than a little upset too."

"So we're both in agreement there; no more non-consensual participants. "

Now that we'd ironed all that out, I figured maybe we could lighten the mood a bit.

I was about to suggest watching a movie or something when Jenna spoke up.

"So...so you said earlier you wouldn't mind doing something again with Trish," she began. "I...I think I'd like that."

"Really?"

Jenna laughed at my obvious surprise. "Really. I was a little nervous about it at first, because I thought I might get jealous even though I told you I wouldn't. But once you got hard, and I could tell Trish was enjoying looking at you, well...I was enjoying showing you off, and...it was a turn on."

"Wow," I said, a bit stunned. "What made it a turn on for you?"

Jenna looked a little flustered. "I dunno. I guess I started imagining what Trish might be thinking, wondering if she was getting horny looking at your cock, if she was imagining doing things to you. Wondering what you were thinking, whether you were hard for me, or for Trish, or both of us."

"That's...fantastic, actually."

It was Jenna's turn to look surprised. "Really? Thought you might think that was weird."

I tried to explain. "There's nothing weird or wrong about it. And I want us to be able to share these kinds of things openly and without judgment if we're going to explore them. I like being watched, you like watching. And now we're both enjoying the idea of having another person involved. As long as we're both okay with it and discuss boundaries beforehand, I don't see why it's something we both can't enjoy. "

"Well one boundary I wanna set right now that I don't want Trish touching you," said Jenna. "She can look all she wants. She can even flash or tease you if she wants to..."

Jenna's hand was suddenly hovering just above my zipper. "...but only I get to touch this, okay?"

The sexual energy in the room had just gone from zero to one hundred in the space of about three seconds.

Jenna leaned in close enough that I could smell her light jasmine perfume, and her eyes fixed on me with her sexy yet somehow still innocent gaze.

"I am still allowed to touch this, right?" Jenna purred. Her fingers were dancing in the air mere centimeters from the bulge that was rapidly expanding in my jeans.

"Of...of course, darlin'," I stammered. "Anytime you want."

"Good," Jenna grinned wickedly, "because I definitely want to."

Her hand closed the distance, her palm now resting on my cock as it struggled, trying to escape the confines of my jeans.

Jenna helped it by undoing the button then slowly pulling down the zipper.

Her head rested on my shoulder, and her soft, sultry voice was in my ear.

"So was it seeing my pussy that got you so hard that night?"

"Y..y..yes," I stammered.

Jenna's fingers were running lightly over my boxer briefs, torturing my cock still confined beneath the cloth. She kissed my neck, nibbled my ear, then whispered into it.

"And you liked showing it off for Trish, didn't you? I saw you looking at her, you were so excited you were practically dripping."

Jesus, I had forgotten Jenna could be this seductive.

"Yes," I groaned, "I liked that she was looking, that she could see it. I was wondering what she was thinking, if she was getting turned on from it."

Jenna's hand gripped my shaft over my boxers. It was pulsing in her hand.

"You wanted to jerk off for her, didn't you?" Jenna purred.

"Oh God, yes." I was so fucking turned on I could barely breathe.

"And I ruined that for you," she sighed. "But I know how to make it up to you."

Suddenly Jenna was tugging at my boxers, pulling them down along with my pants. She had to drop to the floor to take off my shoes, then finished removing my jeans and underwear.

She came back up over me, kissing me lustfully, then lifted my shirt up and over my head.

Tossing it aside, she then stood, pulled out her phone, and started scrolling. I was about to ask what she was doing when the music started playing.

It was a sultry, R&B style song that I didn't recognize. Jenna put her phone down on the arm of the couch and began to dance.

She started simply enough, with a wiggling of her hips as she swayed her body provocatively.

Her hands went to her waist, caressing herself over her shorts, then moved slowly up to her breasts, squeezing them gently as her body continued gyrating.

Her eyes met mine. "What are you waiting for? Jerk it for me, cowboy."

She was so sexy and confident. I immediately obeyed, taking my throbbing shaft in hand.

Jenna gave me a sexy grin, then went back to dancing for me.

I'm gonna be honest: she wasn't the best dancer I've ever seen. But what she lacked in skills she more than made up for in personality. She was just having fun, and of course, so was I.

Jenna slowly began lifting her shirt, exposing her toned belly. It crept higher and higher as she swayed before me. She then turned her back to me and pulled it up over her head.

Or at least tried to. Her shirt got stuck and she struggled with it for several seconds before finally managing to get it over her head.

Jenna laughed. "I really didn't think this outfit through when I decided to do this," she giggled.

"So you planned this beforehand?"

"Well, not really. At least not the striptease. But I did pick out what to wear under my clothes on purpose."

Jenna turned as she spoke, her hands over her breasts, then slid them away to reveal her bra.

It was a sheer turquoise mesh that left nothing to the imagination.

"You like?" Jenna asked.

"Oh yes," I moaned, feeling my cock swell in my hand at the sight of her perky breasts, nipples clearly visible through the mesh.

Jenna smiled, found the rhythm of the music, and again began to sway her hips.

Unsnapping her shorts, she slowly worked them down. Again turning around, she continued to lower the shorts inch by tantalizing inch, revealing the matching turquoise panties beneath. They were just as see-thru as her bra, showing off the creamy smooth skin of her adorable little ass.

Jenna lowered her shorts to her ankles, bending over as she did so. Even the gusset was mesh, and I had a full view of her tight butthole and the plump folds of her vulva pressed together snugly under the almost invisible fabric.

Jenna almost tripped as she struggled to get her shorts over her shoes. Once she finally managed to kick them off, she straightened up and turned her head over her shoulder towards me with a frustrated sigh. "Sorry, I'm not very good at this. Maybe I'm not cut out to be a stripper."

I smiled at her reassuringly. "Don't worry about it, darlin', I think you're amazing. I'm certainly enjoying myself, can't you tell?"

Jenna's eyes found my cock, my hand stroking it with a firm grip, and grinned.

Then she turned to face me fully, and my jaw dropped.

Her panties were just as see-thru in the front as they were in the back. My eyes fixed on them, admiring every detail they revealed.

I'd caught glimpses of Jenna's auburn bush before, but now I saw it fully in all it's natural but neatly trimmed glory.

It framed her vulva perfectly, plump and fair and coming together at her cleft, revealing only a hint of her delicate pink labia. Her clitoral hood jutted prominently from the top of her slit.

This was the most exposed Jenna had ever been in front of me, and I had to stop masturbating for fear I'd cum far too soon.

"Hey," Jenna smirked, "my eyes are up here."

I met her humor filled eyes and finally managed to speak. "Jesus, that's sexy. You're so fucking beautiful."

As a second song now played from Jenna's phone, she once again started swaying to the music, making her way to me slowly.