The Jenna Arrangement Pt. 14

Jenna giggled. "Be careful what you promise, cowboy. My monthly visitor should be checked out by then, and I'm gonna want to cram the next three months of not being with you into one day."

"Challenge accepted," I said with a laugh.

I hit the gym several times during the week, and made a point of using the tanning booth. If Friday night worked out, I didn't wanna look like Casper the Friendly Ghost in a room full of beautiful young women.

Wednesday, I dropped my tuxedo off at the dry cleaners, in need of a good pressing and a few minor alterations. They promised to have it ready by Friday afternoon.

I also went shopping to find Jenna a birthday present. I'd already bought her that black dress at the mall, but I wanted to get her something she could wear on a regular basis, like a piece of jewelry.

I eschewed the overpriced chain stores at the mall and instead visited several local jewelry shops before finally finding what I was looking for. It was still a little pricey, but I had enough room on my credit card and figured I could easily pay it off in a few months. They gift wrapped it for free, so there was that.

Thursday, I got a haircut, then went to spend some time with Jenna, who'd invited me over. She was originally supposed to work, but things were so slow they told her not to bother coming in.

I tried talking her into coming to my place instead, but she insisted I come there, despite Michelle being home, promising me some of the leftover lasagna she'd brought back from the diner the night before. I'd wanted to avoid any possible complications or slip ups about the plans for Friday night, but I also didn't want to seem suspicious by refusing her offer. Plus, I really did miss her.

As we sat and ate, I was beginning to suspect her insistence on me coming there was to get Michelle and I better acquainted, with the ulterior motive of perhaps convincing Michelle to change her mind about the No Boyfriends rule.

Michelle was friendly and courteous, of course, but deftly avoided the topic of the party, and dodged Jenna's attempts to bring it up. Occasionally though, she'd give me a knowing smile.

We said goodnight at a reasonable hour, although Jenna was reluctant to let me go. "I'm so tempted to ask you to spend the night," she sighed as we stood at the doorway, "even though I'm still not quite up for, well..."

I held her close. "Jenna, I'd be more than happy to spend the night without having sex. I'd just want to be with you. But I didn't bring a change of clothes and I have to go to work early. Plus you need a good night's sleep, big day tomorrow."

"I know. I'll just miss you." Jenna gave me one last kiss, and I made my way home.

***

Finally, it was Friday. I did have to work, but I'd already arranged to get off early so I could get everything ready.

I went to the gym for a quick, rare afternoon workout, showered, then picked up my tuxedo, trying it on as soon as I got home.

The alterations made it fit perfectly. It was basic enough that the style was timeless; simple, classy and elegant. I also gave my dress shoes a quick clean and buff before adding them to the ensemble.

I admired myself in the mirror as I fixed the clasp of the black bow tie. "Not bad, old man," I said out loud, "you clean up well." Then I laughed at myself. "You might be better off keeping this thing on all night."

I stripped off the tux, hung it up carefully, then took a nap. I had no idea how long this night might last, and I certainly wasn't the party animal I used to be, so the more rested I was, the better.

I awoke to my alarm two hours later.

I'd had an erection when I woke, and briefly considered taking care of it, but rejected the idea quickly. I hadn't jerked off all week, saving it up so that if I did indeed get naked for the ladies, I would hopefully be fully aroused the entire time. So I ignored my dick and instead headed to the bathroom.

I took some time grooming myself. I wasn't overly hairy, but wanted to trim things up a bit, especially in the nether regions. I also shaved, trimmed my nose hairs, and cleaned, clipped and filed my nails on both hands and feet.

I took a shower. After drying off, I rubbed myself down with body lotion to soften my skin, then put on some aftershave, deodorant, and cologne. All had the same matching scent, just a light hint of mint and spices that left me smelling fresh and natural, not reeking of overpowering perfumes.

I dried and styled my freshly cut hair, using just enough product to keep it in place.

I couldn't remember the last time I'd groomed myself this thoroughly.

I gave my naked body one last lookover. The slightly reddish hue of the artificial tan had faded, as I'd hoped it would, to a more natural looking color. While I was certainly no Adonis, my muscles were looking well toned and my stomach a bit flatter. It would have to do.

I put on the new pair of boxer briefs I'd also purchased earlier in the week. I'd briefly considered a Speedo, but there was no way in hell you'd ever catch me in a banana hammock, even as a joke.

These were simple, black, with an almost velvet sheen and touch to them. They were form fitting but comfortable, and designed to highlight the package up front, which they did, quite well in fact.

Turning around in the mirror, my ass looked pretty damn good in them too. If Jenna objected to full nudity, perhaps I could convince her to let me strip down to just these.

I checked the time; almost 6pm. I made myself a light meal, then went and put on some jeans and a tee shirt. I'd wait til I got to the dorm to put on the tux.

I packed a small travel bag with a change of clothes and some basic sundries that may be needed depending on how the evening went. I was hoping that, no matter how things went at the party itself, I might perhaps still get to spend the night with Jenna. I also packed Jenna's birthday gift, and the condoms...just in case.

I received a text from Michelle at 6:45pm telling me they were leaving. Almost immediately after I received a text from Jenna with a picture attached: Her in the stunning red party dress, and Trish in her blue skater dress. They both looked ravishing.

Her text read: "Wishing you were here. ❤U."

I texted back, "Love you too. Have fun!" then packed my things in the car and headed out, hopeful yet cautious about what lay ahead for the evening.

***

Almost everything was out on the kitchen counter for me when I arrived. The alcohol supply consisted of one bottle of rum, one bottle of vodka, and several bottles of wine. There was also beer in the fridge, and I helped myself to one. I didn't want to drink heavily of course, I wasn't there for that, but it did help take the edge off my nervous excitement.

The snacks were also pretty basic; boxes of microwave popcorn, bags of nachos, chips and pretzels, a store bought cheese and cracker plate, and a couple of boxes of frozen soft pretzel bites and mini crescent dogs, AKA "Pigs In A Blanket." There were also a variety of dips and sauces, as well as paper plates.

None of it would take long to prepare, and most I wouldn't want to open until just before they arrived. Still, I spent some time familiarizing myself with where everything was and locating a few other items I'd need.

With time to kill, I found myself channel surfing, but nothing truly held my interest, my mind too preoccupied with how this could go.

I should have been used to the idea of being naked in front of women by now, having done it with both Jenna and Trish. But Michelle would now also be a part of it, willingly this time, along with at least two other new girls I hadn't even met yet.

I found myself talking to myself. "Relax. You're not here for an orgy, or to do anything with them really. Don't worry about whether they find you attractive or whatever. Be polite, be friendly, be respectful, and have fun with it, right?"

My fears kept trying to creep in. "What if Jenna objects? What if she gets angry about it? Or what if she goes along with it for her friends, but winds up resenting it?"

I practiced my breathing exercises to calm myself as my dialog became internal. "It will be fine. I won't do anything unless I'm sure she's okay with it first. And if things get weird I'll just end it, get dressed and go."

The second beer I'd drank was a mistake, and I found myself urgently needing to pee. "No more beer," I told myself, "unless you wanna spend half the night in the bathroom."

I relieved my bladder and used some mouthwash to freshen my breath, and as I turned to exit, spotted something that froze me in my tracks.

It was a laundry basket. With the lid open. And, sitting right on top, was a silky black thong. The only two people currently living here were Jenna and Michelle. And I'd never seen Jenna wear a thong.

I slowly put out my hand, reaching for it, wanting to touch the soft, tiny gusset. I could see a white stain there clearly, and I desperately wanted to smell it, to sample what I was pretty sure was Michelle's most intimate scent.

Instead, my hand closed the basket lid.

"No," I berated myself firmly. "No fucking way are you going to invade her privacy like that."

The spell broken, I turned and exited the bathroom.

***

I got a text from Michelle at 11:05 pm. "On our way back. Approx 20 minutes."

I put on the tux, then started setting up the snacks. I'd found their wine glasses and poured several, setting them on a silver tray. I practiced balancing it for a few moments to make sure I still knew how to carry it properly, hoping like hell I didn't drop the damn thing. Then I filled two ice buckets, one to chill the open bottles, the other for the mixed drinks.

I'd just finished laying everything out when I heard them coming up the walkway, all laughter and bustling energy.

Thinking quickly, I draped a white hand towel over my arm and, balancing the wine tray, made my way to the living room so I could greet them when they came through the door.

I stood straight and rigid, one arm behind my back, the other holding the tray, approximating, as best I could, the look of a formal butler.

Still, I trembled a little as I heard the key in the lock.

Michelle came through first, followed closely by Jenna. Trish was directly behind her, covering her eyes. Two new faces I didn't recognize trailed behind them. Between the tittering laughter and their clumsy wobbling as they entered, it was pretty obvious that, while they may not have been able to legally buy drinks at the club, they'd all managed to get a pretty good buzz on somehow.

Jenna was complaining good naturedly. "Okay, okay! I'm inside now! Can I open my eyes already???"

Michelle caught my eye, grinning widely. I smiled back, then tightened my formal stance.

Michelle nodded at Trish, who pulled her hands away with a loud, "Ta DA! Happy birthday!"

Jenna's eyes met mine, and her face lit up with joy. "Tommy???"

I bowed slightly, holding out the wine tray one handed, my eyes never leaving hers. "Good evening, young miss, and happy birthday. I hope the evening's festivities have been to your liking so far. Would you care for a drink?"

Michelle had barely enough time to rescue the wine tray before Jenna almost tackled me with her hug. She smelled faintly of vodka and weed.

"Oh my God, I'm so happy to see you!" Jenna squealed. She kissed me hard, then pulled back. "Nice suit! You look amazing!"

"So do you," I said. "I knew that red dress was the one."

Still grinning ear to ear, Jenna asked, "Who's idea was this?"

I nodded towards Trish and Michelle, who were already helping themselves to the wine.

Jenna ran over and hugged them. "I love you guys! Thank you so much! Best birthday present ever!"

"Oh, we've only just gotten started with the surprises," Michelle said, giving me a sly wink.

Jenna saw the wink and looked back at me, happily confused. "Really? Like what?"

"We'll get to that," I said, taking the wine tray back from Michelle and repositioning it in my hand. "But first, why don't you introduce me to your other friends?" I nodded my head in the direction of the two young ladies I'd seen come in earlier, still standing near the door.

Jenna gave me a quizzical smile, still not quite catching on to my butler act. But she waved her friends over excitedly.

"Tammy, Nikki, this is Tommy, my boyfr..."

"Butler," I said, cutting her off with a smirk. "Tonight, I am your butler. Your wish will be my command." Jenna again looked at me, understanding slowly dawning on her face. "I love you," she mouthed silently. I simply winked back.

Turning to her friends, I greeted them with a bow. "Tammy, Nikki, it is my great pleasure to meet you. For tonight, I think it best you call me Thomas, my formal name. Now, may I offer you ladies a drink?"

Tammy, a stunning blonde that looked like every head cheerleader you've ever seen, laughed and gave me her best, if slightly inebriated, attempt at a curtsey. "Nice to meet you, Tommy, I mean Thomas. Thank you," she giggled as she took a glass of wine from the tray I'd extended.

Nikki, a curvy, athletic looking young woman with skin almost as dark as her glassy, slightly red eyes, took her drink with a wry smile. "Why thank you, kind sir," she said, deciding to play along. "It's nice to make your acquaintance."

"Okay, ladies, listen up!" Michelle's voice rang out across the room. "Time to get out of these dresses and into our PJ's!"

Michelle came over to the new girls. "Tammy, Nikki, you can change in the spare rooms. Let's all get comfy, and then we can really get this party started!"

As she guided them towards the hallway, I saw her speaking softly to them. Tammy and Nikki looked back towards me over their shoulders, giggled, then nodded at Michelle.

"What's that about?" Jenna was at my side, watching them leave.

Before I could respond, Trish swooped in. "Jenna, we need to talk. Let's go in your room."

Jenna looked very confused, especially when I followed them both into her room and closed the door. "You guys gonna tell me what's going on or what?"

"Okay, so..." Trish took a deep breath, trying to decide how to start.

I helped her out. "Trish and Michelle had an idea to do something special for your birthday, but I'd only agree to it if you did."

Jenna still looked confused. "And?"

"And..." said Trish, steeling herself, "we knew you wanted Tommy here. So we invited him to come and be our butler." She paused before finally spitting out, "Our NUDE butler."

Jenna was dumbfounded. She looked at Trish, then me, then back at Trish. "This was YOUR idea?"

"And Michelle's," said Trish nervously.

Jenna whipped her head back at me. "And you agreed to it?"

"Only if you agree to it, Jenna," I said firmly. "Trish and Michelle thought you might find it fun. But if not, then I'll remain a fully clothed butler. Nothing else happens unless you're on board."

Jenna sat on her bed, stunned. "You guys planned all this behind my back?"

We both nodded. I was tense, unable to gauge her reaction at all.

Jenna sat quietly for a moment, looking deep in thought. Then she jumped up excitedly. "I LOVE this idea!"

I don't know who breathed a louder sigh of relief, Trish or myself.

Jenna threw her arms around us, hugging us close. "I have the best friends ever!"

Jenna seemed a little tipsy, giving me cause to worry about her judgment, but I held off saying anything for the moment.

Jenna turned to Trish. "So Michelle's in on this. But what about Tammy and Nikki? I don't want to freak them out or make them uncomfortable."

Okay, so perhaps she wasn't as impaired as I'd thought, if she was considering the other girl's feelings.

"Tammy and Nikki are aware," said Trish. "Michelle told them all about it before inviting them to make sure they'd be up for it. Our original plan was for Tommy to be naked when we walked in, but he insisted we made sure you were cool with it before going that far."

Jenna looked up at me. "Really? Thank you. I think that may have been too much of a shock to my system," she said. "I'm glad I had a moment to think it over first."

Jenna sat back down. "So...how do we start this?"

"I don't really know," I laughed nervously, the reality of the situation now truly hitting me. "I hadn't actually put much thought into it besides getting your permission."

Trish spoke up. "The idea Michelle and I had was that Tommy would act as our server tonight, bringing us snacks and drinks and stuff. None of us want to do anything more than, you know, look at him. Like those CFNM parties we'd talked about. No sex or anything. Just a naked guy serving a room full of women."

Jenna nodded, her trademark grin lighting up her face. "I have a few ideas," she said. She glanced up at Trish. "Can I talk to Tommy alone for a minute?"

"Sure," said Trish, "I'll go get changed in Michelle's room."

After the door closed, Jenna directed me to sit beside her on the bed. "First of all, I love you," she said.

"I love you too."

Jenna looked me directly in the eye. "Are you truly okay with this?"

"I am," I nodded, "only as long as you are. You call the shots. You decide how far anything goes. And if you say the word, it's over. I put my clothes back on and leave."

Jenna looked at me deeply. "Do you trust me?"

"Implicitly."

Jenna leaned in and kissed me. "Then let's do this."

Jenna stood, then grabbed the jumper she'd bought at the mall from her dresser. "I'm gonna go change in the bathroom. Wait here, stay dressed for now. I'll come get you in a few minutes."

She saw the disappointment I must have had on my face at not being able to watch her undress, and smiled apologetically. "Sorry, but I have to, well, freshen up a bit too. Lady stuff, you know."

She blew me a kiss and was out the door.

I sat on the edge of her bed, calming myself. It wasn't long before I heard a flurry of activity coming from the hall. Female voices, giggling and excited, making their way into the living room. I could hear Jenna, but couldn't quite make out what she was saying. She spoke briefly, then footsteps signaled her approach.

Jenna opened the door. The sight of her now in her adorable, form fitting jumper made my heart race.

She saw my look and smiled. "Save it for later, cowboy. We're ready. Are you?"

I took one last deep breath, held it, then exhaled slowly. "Ready as I'll ever be."

"One last thing," said Jenna in a low voice. "If you start feeling uncomfortable in any way, tell me you're 'feeling cold.' I'll get you out of there, okay?"

"I don't think I'll need to, but okay," I said. "Same with you. If things go too far, tell me you're not feeling well or something. We can come back here and talk it over."

"Agreed," nodded Jenna. She kissed me passionately, stirring my desire, then took me by the hand and led me to the living room.

The sight that greeted me there was a fantasy come to life. The four young ladies had changed into their sleepwear, and my eyes couldn't decide where to look first.

They settled on Trish, in her purple cami and shorts, toying with the curly dark hair that cascaded down to her shoulders as her gaze met mine. She angled her body subtly towards me, her breasts shifting loosely with her movement, and dropped me a wink.

Michelle sat next to her on the couch, wearing a lacy pink babydoll that, with the way her legs were crossed, wasn't quite concealing the matching panties beneath. Her dark nipples stood out clearly beneath the lacy fabric.

Tammy and Nikki had taken the two adjoining cushioned chairs that had been moved closer to the couch, forming a crude semicircle.

Tammy, the All American blonde, wore a rose colored two piece mesh lingerie set, with crisscrossing straps that ran across her ample cleavage. The floral lace shorts were sheer, enticing me with the hints of milky skin they revealed beneath it.