The Jenna Arrangement Pt. 19

ALL CHARACTERS ARE AT LEAST 18 YEARS OF AGE OR OLDER.

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"Of course you can go. Why would I mind you going to a strip club?"

I hadn't been to a strip club in years. But my new friend and coworker Mike had invited me to go with him for the evening.

It's not that I expected Jenna to object, really. But Trish had gone home Wednesday night, (with the promise to return on Saturday and spend the weekend,) and while Jenna seemed to be in good spirits considering the drama her mother and her pervert boyfriend had put her through, I was wary of leaving her alone. She also had her period, and hadn't been feeling well the past few days.

"Look, seriously, just go," said Jenna. "I'm glad you made a friend. You need to get out more, do GUY things."

"I appreciate that," I said. "And you're right. But I was worried about, well....first, leaving you by yourself. And second, that you'd..."

"What, object to you seeing some tits and ass?" Jenna broke in. "Are you planning on fucking any of them?"

"No, of course not!"

Jenna's trademark grin lit up her face. "Then go! Enjoy! Have a few beers, stick some dollars in some G-strings! Get a lap dance! Find a dancer with bigger boobs than mine and motorboat her! I won't mind."

"You'll be okay by yourself for the night?" I asked.

Jenna sighed, but her smile remained. "I'm fine. Truly. In fact, I think I'll use the alone time to work on my Only Fans content. I've been neglecting it all week. Although I can only do so much until my period is over."

Jenna took my hand. "Look, you go check out some strippers. I'll be checking messages and flirting with customers."

Her hand dropped to my crotch, rubbing it as she licked her lips. "And maybe when you get home I'll take care of you."

"Deal," I grinned. I pulled her to me, our bodies close, and kissed her hard.

I suppose before I go any further, I need to provide a little background.

I work for a company that sells and installs fire alarm systems. While I do work on some installations and repairs, my main job is to inspect them. The state requires all public buildings to have their fire systems inspected annually to make sure they are maintained and in proper working order by an outside contractor.

That's where I come in. I spend most of my days on the road, traveling around to various companies, schools, churches, hotels, shopping centers etc. Some days I'd spend at one large location, others traveling around inspecting several smaller ones.

It's a pretty easy job, although rather dull and routine. But at least I'm not trapped in a cubicle somewhere.

Mike was hired a few weeks ago to be my assistant. The idea was for him to help me on the larger inspections and, once fully trained, to be able to go out on his own and take some of the smaller jobs off my plate.

For now, he'd been riding with me everyday in my company truck.

We hit it off pretty quickly, despite him being several years younger. It began easily enough with both of us having the same tastes in the classic rock music we'd listen to while traveling around. We also bonded over football, both fans of the same team.

I hadn't had a male friend....hell, I hadn't really had ANY friends in quite a long time. But after my conversation with Jenna awhile ago about our futures and trying new things, I'd decided to open myself up to the possibility.

So when he invited me to his place a few Saturdays ago to play some pool, I accepted.

There I met his wife Ellie, a lovely woman, and their teenage daughter, Megan.

We spent the afternoon hanging out in his basement "man cave," playing pool and drinking a few beers. Later, Ellie cooked us a wonderful dinner.

Naturally, they asked questions about my life and relationship status. It was the only time I felt uncomfortable. While not wanting to lie, I also wasn't quite ready to share everything. I did tell them about Jenna, that we were a relatively new couple, but didn't go into too many details on how we met. Nor did I discuss the age difference.

"Well, she sounds like a lovely woman," Ellie said, "Perhaps next time she can join us, I'd love to meet her."

"She's...away for the summer, visiting family," I said, keeping as close to the truth as I could without getting into details, "but sure, when she gets back, that would be nice."

The words surprised me even as they left my lips. Would I actually be comfortable bringing my just turned twenty year old girlfriend over? They didn't seem like the judgemental types, but still, I'm sure they'd think it odd.

Or maybe I was still just projecting my own fears and insecurities.

I was a little surprised when Mike had suggested going to the strip club Friday night. "Ellie doesn't mind that kind of thing?" I asked tentatively. I didn't want to make him uncomfortable about it if he was sneaking around without his wife's permission.

To my relief, he laughed. "Oh no, she doesn't care, trust me. She's very...understanding about it. Look, I don't want you to get the wrong idea. I love my wife, and we're very happy together. And she understands a man's needs. It's not like I go to strip clubs all the time. I just thought it would be fun, but if you're not into it, or your girlfriend has a problem with it, I get it, no biggie. Just an idea."

"Oh, I doubt Jenna would object," I said. "But..." I paused for a moment, considering just how much I wanted to tell him.

Fuck it. If I was trying to make an actual friend, lying to him wasn't a great way to start.

"Jenna's back from visiting her mother," I explained. "There was, unfortunately, some...drama. Personal stuff. So she came back early. She's..." Again I hesitated, because I knew the more details I gave, the more questions I'd probably get.

"She's staying with me for now, until she goes back to college in the fall. And I'm just worried about leaving her alone at the moment."

As expected, Mike looked surprised. "You're dating a college girl???"

I nodded and smiled sheepishly, waiting for his reaction.

Mike was silent for a few moments, considering this revelation. Then broke into a wide grin. "Damn! Good for you, dude." To my surprise, he asked no further, prying questions.

Instead, he simply said, "Well, talk it over with her I guess, and let me know. I'll understand if she's not cool with it, or you decide the timing is bad."

Jenna was, of course, "cool with it." And so Mike and I met at the club around 8 PM, each of us having taken an Uber. We didn't plan on drinking heavily, or at least I knew I didn't, but it was the safest option and ensured neither of us would be driving home later after "one too many."

8 PM was still rather early as strip clubs go; the crowd usually not packing in until later. But that was fine with us. "I can't be out too late," explained Mike. "Ellie is understanding, as I said, but I don't want to take advantage. Besides, she's usually waiting up for me, if you know what I mean."

"Oh, I get it," I chuckled. "Jenna has suggested she might be 'waiting up' for me when I get home, too."

Mike laughed. Clapping me on the shoulder, he led me to the bar. "Come on, the first round is on me."

It was a pretty nice place as strip clubs go, clean and upscale, but not outrageously expensive.

There was currently only one dancer on the stage, a young black woman with massive tits and incredibly thick ass. She was currently topless, stripped down to only a G-string. From what I recalled of the place, that was legally as far as they could go, at least on stage. The lap dance booths and VIP rooms were a different matter, depending of course on how well you tipped.

We hadn't even ordered our drinks yet, but Mike was already waving the dancer over, extending a crisp dollar bill in her direction.

"Hey handsome, welcome," she purred, already pouring it on. Turning, she pointed her dark, plump ass towards Mike, who immediately slid his tip into her G-string.

She next turned to me, dangling her lovely breasts close enough for me to place my obligatory tip in her warm, slightly sweaty cleavage.

"Thanks, sugar; if you want a lap dance later, I'll be available in a bit," she offered with a sultry smile.

I nodded politely, groaning inwardly. I'd forgotten just how fast they went for your wallet. Still, I knew that going in, right? I suppose I just needed to lighten up and roll with it.

And by the time our second round of drinks arrived, I had. The parade of girls seemed almost endless, with each new dancer arriving on stage, dancing and stripping down from their wild assortment of outfits to the lingerie concealed beneath, then finally to nothing but their bikini bottoms or G-string before gathering up the pile of bills tossed on stage by the growing crowd of increasingly excited and intoxicated men.

After stepping off stage, they'd then of course make the rounds, soliciting more tips from the patrons and offering lap dances or visits to the backrooms.

While I'd managed so far to decline any lap dances, I'd relaxed enough to enjoy myself, and the attention from the ladies as they ground up against us, teasing us with their wares.

While there were a variety of beautiful women, all shapes, sizes and colors, none of them really caught my eye, maybe because I knew I had a cute little redhead waiting for me at home.

We'd just gotten round three when the DJ introduced the next dancer: "Guys, put your hands together and make some noise for Blondie!"

My heart skipped a beat as the long legged, big busted blonde took the stage in her school girl outfit. "I know her!" I thought.

She took the pole, wrapped her legs around it and began a slow grind. Flipping her gorgeous locks back, she turned her head, and her blue eyes met mine. Her brightly glossed lips smiled in recognition.

It was Tammy! One of the young ladies Michelle had invited to the Girls Night / Birthday party for Jenna.

"Blondie" never missed a beat as she launched into her routine, gyrating on the pole, then lifting her plaid skirt to reveal the hot pink G-string beneath it, shaking her firm, tight ass to loud hoots and hollers.

Strutting with confidence across the stage, she slowly unbuttoned her billowing white uniform shirt, pulling it open to reveal a matching pink bustier. Her breasts bounced with every movement as she continued to dance and writhe.

Tammy made her way directly in front of me, bending over and giving me an incredible view of her cleavage before deftly turning on her heels, reaching behind her, and unzipping the bustier.

It dropped to the floor as she spun again, her hands now over her breasts. She did a lap around the stage, still holding her breasts as the men rained dollars upon her, stopping again directly in front of me before arching her back and tossing both hands straight up in the air in Victory formation, revealing her spectacular, natural boobs fully to the crowd.

Tammy looked down at me with a knowing grin. I couldn't help but smile as I reached out and offered her a tip.

She bent low and wrapped her breasts around my hand, trapping the bill between them and pulling it free. She dropped me a quick wink, then made her way around the stage, collecting more tips.

For her finale, she again took center stage and slowly pulled off the skirt. Standing clad now only in the miniscule G-string, she grabbed hold of the pole then dropped to a crouch, her legs swinging open and closed, teasing the audience.

Dropping to her hands and knees, she crawled across the stage as still more money flew onto it, again stopping right in front of me. Rolling over to her back, she spread her legs wide, lifting them almost straight up in the air.

The tiny piece of fabric she wore barely concealed her cleft. Her smooth, plump vulva, however, were clearly visible, damp with the sweat of her exertions. The natural blonde pubic hair I'd noticed under the lingerie she'd been wearing at the party was now gone, leaving her rounded pubic mound smooth and bare.

Tammy, AKA "Blondie," sat up and, again making eye contact with me, reached between her legs and ran two fingers along the edge of the thin strip of cloth covering her slit and, for just a moment, I thought I could make out a hint of her labia.

Then she was up and moving around the stage, collecting still more money, before taking the pole one last time and performing an almost gymnastic routine that whipped the crowd into a frenzy.

She finished her routine to loud cheers and a rain of cash tossed onto the stage. Quickly, she gathered up the money as the DJ introduced the next dancer.

"Dude, I think she really likes you," Mike's voice was close in my ear, speaking loudly over the din. "If you don't get a lap dance from her, I sure as hell will!"

I debated on telling Mike I knew her, but instead just smiled and laughed. "Well, maybe."

I lost track of Tammy once she left the stage, and was wondering if she'd make her way over at some point or intentionally avoid us. She didn't seem at all embarrassed to have recognized me, but that didn't mean she necessarily wanted to actually talk to me.

Then I spotted her, making the rounds at the bar, coaxing tips from the guys one by one. She was wearing only the bustier, G-string, and heels.

Eventually she made her way to us. "Tommy!" she exclaimed, throwing her arms around me. The shocked look on Mike's face was almost priceless.

"Hey, Tammy, I didn't know you worked here."

"Yeah, just started this summer; a girl's gotta make a living," she said with a grin.

"You two know each other?" Mike broke in.

Tammy laughed. "Yeah, well, sorta. We met at his girlfriend's birthday party. It was...quite the night."

I laughed nervously, hoping she wouldn't start going into details. "Yeah, it was. Oh, and by the way, this is Mike, a buddy of mine from work."

"Hey, Mike, nice to meet you," she purred, giving him a hug, then turned so her ass faced him and bent forward slightly.

Mike stared blankly at her round, tan bottom for a moment before remembering to tip.

To my surprise, Tammy then plopped herself in my lap and wrapped an arm around my shoulder. "Do me a favor? Buy me a drink? The manager doesn't like us socializing with the customers too long, but if you buy me a soda, I can stay and chat for a bit."

I flagged the bartender down and ordered her soda, which arrived promptly.

"So how's Jenna? I guess you don't get to see her much since she went home?" Tammy asked.

"She's fine," I replied, "she's actually staying with me for the summer now."

"Really? That's great," exclaimed Tammy. "Maybe we can get together again sometime! You know...hang out."

If Mike picked up on the innuendo behind the way she stressed those last two words, or the wink she dropped me, he didn't show it. "Sure," I replied, "I'm sure Jenna would be happy to see you."

Tammy remained on my lap for several minutes, sipping her drink slowly as we chatted amicably. She did most of the talking, really, and while I nodded and smiled and interjected when appropriate, I found it difficult to truly pay attention to what she was saying.

The scent of her perfume, mixed with her perspiration from her earlier exertions, was intoxicating. Then there was the way she'd shift her body on my lap as she spoke or laughed, her breasts occasionally brushing against my chest, and her all but naked ass pressed firmly on my groin. I could feel the warmth of her soft bare skin under my arm, wrapped as it was around her waist, although I made sure my hand traveled no further than her hip as I held her.

My cock was definitely noticing all of this as well, and reacted accordingly.

Tammy squirmed yet again on my lap as she leaned closer to speak directly in my ear. "If you're interested, and it's not too weird for you, I'd love to take you to the VIP room. Don't worry, I can get you a 'special discount.'"

I wasn't at all sure how to handle this invitation. Noticing my hesitation, Tammy continued, "Look, I'm not trying to do anything that would get you in trouble with Jenna, I promise."

"I really appreciate the offer," I smiled nervously, "just...let me think about it, okay?"

"Sure," said Tammy, "no problem. I get it. Tell ya what, let me finish my rounds, collect a few more tips, and I'll be back in a bit."

Tammy hopped off my lap, gave me a quick peck on the cheek, and was off.

Mike was staring at me, wide eyed, with a huge grin. "Dude. I think she's really into you." I had no idea how to respond to that other than shrug and sip my drink.

My phone started buzzing in my pocket. It was a text from Jenna: "Hey, I'm suddenly not feeling well, so I think I'm gonna crash early. Sorry, I know I said I'd wait up. I'll make it up to you, I promise."

"Excuse me, I'll be right back," I told Mike, then made my way outside to call Jenna.

"You okay?" I asked when she picked up.

"I'm fine, just...cramps. They're usually gone by now. But I'll live, nothing I haven't dealt with before."

"I can come home early if you'd like," I said.

"No, stay, have fun, please," Jenna said. "Find yourself a cute stripper you can jerk off to later. I just feel bad I'm not up to taking care of you tonight myself."

"Don't worry about that, darlin', just get some rest. Hey, speaking of cute strippers, you'll never guess who I ran into. Turns out Tammy works here."

"Really?" Jenna gasped. "Wow, that's wild. That must have been weird, running into her like that."

"Yeah, but she seemed fine with it. She even..." I paused for a moment, then decided it was best to be honest. "She even invited me for a VIP dance."

"Did you do it?" Jenna asked, not sounding upset or on guard at all.

"No, not yet," I said. "Although being honest, I was considering it. Glad you texted, because I wanted to run it by you first."

I could almost see Jenna's smile as she sighed. "I already told you: have fun. My only rule is she doesn't fuck you, okay?"

"Don't worry, I don't think that's her intent, and it's certainly not mine." I assured her.

"Then go enjoy yourself, cowboy."

I returned to the bar to discover Mike missing. Looking around, I spotted him on one of the couches, getting a lap dance from the busty young black woman we encountered when we first arrived.

I'd just finished my drink and was about to order another when I felt an arm slide around my waist. "Hey," said Tammy, "You still thinking it over, or...?"

Her smile was brilliant and genuine. I couldn't resist. "I'd love to," I said.

Tammy took my hand and led me past the couches where several dancers were performing. I caught Mike glancing my way and gave him a quick nod before Tammy pulled me along still further, down the hall that led to the "VIP Area."

"You'll have to pay the bouncer twenty bucks, that's the minimum cover, but the rest is on me, okay?" Tammy said.

I gave the huge, muscular man a fresh twenty, then Tammy leaned up to him, whispered in his ear for a few moments, then produced a small wad of cash from the little purse she'd been carrying it and handed it to him. He gave her a knowing smile and a nod, then opened the door to the room.

"Have fun, my man," he said as we passed through, then closed the door.

The room was small, dimly lit, but clean, with a dancer pole in center and a small leather ( or more likely faux leather) couch against the far wall. The walls were covered with mirrors. On the left side was a door marked with the universal symbol for a restroom. Speakers mounted in the upper corners pumped in the music, but at a much lower volume than the main stage.

As Tammy led me to the couch, I asked, "Why did you pay him?"

"Oh, just to make sure we weren't bothered for a while. Twenty is the minimum charge for fifteen minutes, but I told him you're a friend and I didn't want to rush things."