The Jenna Arrangement

FORWARD: This picks up immediately after the events in chapter 14.

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

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I'd only been in the shower for a few minutes when there was a knock at the door. "Tommy?" called Jenna, "can I come in?"

"Of course," I called back. I assumed she had to pee, so imagine my surprise when, a minute later, the shower curtain slid open and a fully naked Jenna stepped in to join me.

"I just wanted a little alone time with you," she sighed as she slid into my arms under the warm spray. My hands fell naturally around her body. Every time touching her still felt like the first time.

After a loving kiss, she looked up at me questioningly. "I also wanted to make sure you're okay about everything that happened. That there's no, you know, regrets or misgivings."

"None at all. I had an amazing time. How about you?"

Jenna's already bright smile widened. "No regrets at all. No jealousy. I was happy to share you with my friends like that. Although frankly, I was kinda surprised that Trish wound up being the only one who touched you."

"Well, in the spirit of honesty, Michelle did wind up groping me in the hallway earlier tonight."

Jenna's eyes widened, but didn't look upset. "Oh really?"

"Yeah. Only for a few moments, though. Just teasing me a bit."

"How did she grab you? Like this?" she asked playfully, taking my cock in her hand.

"Y,yeah," I stammered, "just like that."

"Did she stroke it like this?" Jenna purred as she caressed my still sensitive shaft.

"Yes."

"And did you get hard for her?"

I was already swelling in her hand as I again responded, "Yes."

Jenna let go of my cock and threw her arms around my neck. Her kiss was hot and urgent.

Our hands caressed each other's wet, naked bodies as our passion built, my now almost full erection pressing up against her belly. Jenna rubbed her warm, slippery skin against it, coaxing it all the way back to its full glory.

I was pleasantly surprised at how quickly my body had responded. It had been quite some time since I'd been having sex on anything resembling a regular basis, let alone multiple times a night, so of course I had concerns about being able to keep up with a much younger woman's sex drive. But so far at least, I'd been performing quite well in that regard. Maybe it was the regular workouts keeping me in shape.

"What are you thinking?" Jenna asked, bringing me back to the moment.

"What? Oh, sorry. Just thinking that joining the gym turned out to be a really good investment."

Jenna looked confused for a moment. Then my cock moved, pushing harder against her, and an understanding grin lit up her face. "Ah, I get it. Increased energy and stamina, huh?"

I grabbed her ass, pulling her even closer against me. "Damn right."

I caressed her ass for several moments, but as I started to slide one hand lower, between her legs, to explore her deeper, she stopped me.

"I'm...still bleeding," she explained with embarrassment.

I pulled my hand back and reached up to touch her face. "Hey, it's okay, no worries."

Jenna flushed even deeper. "Would...would you still...fuck me? I was gonna wait til tomorrow, but I really need you right now. Unless you think it's too gross, or..."

I cut her off with a kiss, then spun her carefully so that her back was to me. I hugged her close, my cock now pressed firmly between her soft, round bum.

"Jenna, I love you," I spoke in her ear, "and there's nothing gross about your period. As long as you're comfortable, I'm more than willing...if you can't already tell."

Jenna objected no further as my one hand fondled her breasts, feeling her nipples stiffen, my other sliding down over her belly to her rounded pubic mound, fingers twirling through her fine red pubic hairs before finding the soft pink folds covering her clit. Spreading them gently, I lightly teased her already swollen button.

Jenna moaned softly, her ass now working itself up and down along my shaft, the spray from the shower naturally lubricating everything.

After a few moments of playful teasing on both our parts, she was ready.

Jenna leaned forward, bracing her arms against the wall of the shower stall, bending low and spreading her legs, presenting herself to me. She looked back over her shoulder with imploring eyes. "Just fuck me, please."

Her pussy was warm and willing to accept me, and I was inside her in moments.

Jenna gasped as I eased my full length into her, and immediately began to rock herself back and forth on it, her pert breasts swaying with each thrust. I held her hips and worked with her, matching her movements.

Our pace was slow at first, allowing me to feel every sublime contraction of her vaginal muscles as they squeezed closed behind my retreating shaft, only to expand around it again as I reentered her. She was incredibly tight, and it was only the fact that Jenna lubricated so naturally that allowed my passage into her easily.

"Fuck, that's nice," Jenna cooed. "I can feel every inch of you opening me up, stretching me, filling me."

I was surprised to see there was very little blood as my cock slid in and out of Jenna's narrow slit. What did trickle out was washed away quickly by the shower spray.

As Jenna's moans became louder, her bucking became more urgent. "Fuck me harder," she pleaded. "I'm...getting close. So...fucking...close!"

I quickened my pace, my balls now slapping up against her clit with each deep penetration.

Jenna was supporting herself one handed against the wall; her other tried in vain to stifle her increasing squeals of pleasure.

She threw back her head and let loose a long, muffled wail and her pussy clenched around me, her climax rippling through her in waves.

I continued to fuck her for several more minutes until finally, despite having just had a mind blowing orgasm myself not all that long ago, I felt the tingling sensations that signaled the approach of another.

Jenna felt it too. She looked back at me, her desire palpable. "Cum in me," she begged, "I wanna feel it! I need to feel you fill me! Yes, yes, I feel you swelling up, oh FUCK that's deep, so fucking deep! Right there, yesssss..."

I lost control as my cock erupted for the second time that night, pounding her roughly with thrust after wet, smacking thrust, until my balls were again completely drained. Jenna kept matching my thrusts in intensity, and the sounds of our sexual lust echoed through the tiny bathroom.

Finally spent, I removed myself from Jenna carefully, then turned her back around to face me.

"I love you," she whispered.

"Love you too, princess."

We held each other close for a little while, kissing and lightly touching. When the water started to cool, we realized we'd better clean ourselves before we ran out of hot water.

As we washed up, Jenna giggled suddenly. "Well, THAT'S a new sensation."

Seeing my confusion, she explained, "I'm used to feeling blood trickle out during my period. But I'm not used to feeling cum dripping out of me. Strange, but not entirely unpleasant."

Reaching down, she parted her delicate pink pussy lips and squatted a little. I watched, fascinated, as she squeezed out a huge glob of my cum. It hung in a long string for several moments before dripping into the tub to be washed down the drain.

"That's a couple more firsts for me," she continued, sounding amused. "First shower sex, first time I've had sex on my period, and first time I've let a guy cum in me without a condom."

I'd been so in the moment I hadn't even considered that. "Well, I suppose it's the least risky time to do it," I mused.

Jenna shrugged. "Definitely lowers the odds of getting pregnant, although it's not impossible." When she saw my worried look, she laughed. "Don't forget, I'm on the pill, too. I think you're safe for now, cowboy."

I stepped out after finishing, but Jenna lingered. "You filled me up pretty good. Between your cum and my period, I may need a pad instead of a tampon."

"Sorry for the mess."

"Don't be," she smiled. "No regrets. But after this, it's back to condoms."

Giving her one more kiss, I wrapped myself in a towel and ducked out while Jenna remained behind to tend to her "lady business."

I almost bumped into Trish, standing in the hall. "I really gotta pee," she pleaded, "is she done in there yet???"

"She should be out any second," I said. "Sorry we took so long."

I turned towards Jenna's bedroom and had just grabbed the doorknob when Trish put a hand on my shoulder. "Tommy?"

She looked nervous, and a bit off balance as I turned to face her. "I'm more than a little drunk," she said, slurring slightly as if to emphasize her point, "and I'll probably either regret or forget this tomorrow, but..."

Trish moved in before I could react, put her hands behind my neck, and plunged her lips against mine, giving me a wet, sloppy kiss. Then taking two steps back, looked me dead in the eye and lifted her cami.

Her breasts were large, round, and almost milky white, so fair I could see the veins beneath her skin. They were capped off with large, dark areola and nipples the size of pencil erasers.

Trish shook them back and forth a few times, their firm, heavy flesh swaying left and right, then yanked her shirt back down and turned to the bathroom. "Jenna, I'm coming in, whether you like it or not!"

She was gone behind the door before I could so much as exhale from my shock.

I decided it was best not to mention what just happened to Jenna, at least not tonight. Trish was drunk, and while she'd broken the "no lips" rule, (come to think of it, so did Michelle earlier, but that was only a peck on the cheek) I don't think she meant any harm by it.

And she was probably right. She'd forget all about it by morning.

***

Jenna joined me in her room several minutes later. She looked at the tee shirt and sweat shorts I'd put on with mock disappointment. "Quitting on us so soon?"

"I think I've had more than enough of being Sir Thomas, Nude Butler, for one night," I laughed.

Jenna hugged me, her towel slipping away as she did so. I held her naked body tightly. My mind was already wanting her again, but I knew there was no way in hell my body would cooperate a third time.

So instead I watched her get dressed. Jenna saw me looking at the string of her tampon dangling between her legs as she slipped her panties on and blushed. "Should be gone by tomorrow, hopefully."

Instead of putting her romper back on, she dressed in a simple, cute pajama set. "Gotta wash that romper," she said, giving me an accusatory grin, "you got cum all over it."

Now I was blushing. I knew I'd cum a lot from the double handjob I'd received earlier, but assumed most of it had landed on me. It seemed I was much messier than I'd realized.

Once dressed, we went out to rejoin the party. We entered the living room to a round of applause, and now we were both blushing.

"Jesus, and I thought I was loud," cracked Michelle, producing laughter from the other girls. Moments later, Jenna and I joined in.

Trish waved us over to rejoin her on the couch. I'd only made it one step before Jenna held me back. "Let's get a drink," she said suddenly. I caught Trish's nervous glance our way just before Jenna grabbed my arm and directed me towards the kitchen.

Jenna poured herself a small glass of wine while I fixed a rum and Coke for myself. "Trish told me she kissed you," she said, so quickly and casually that I spilled soda all over the counter.

"Um, yeah, sorry. I was gonna say something when the moment was right. It was nothing, just a smooch on the lips. She did it so fast I didn't have time to react."

Jenna smiled. "Relax. I can't really get pissed about a drunken kiss when I just let her help me jerk you off, can I?"

Jenna helped me clean up my spill, and as we gathered up our drinks, she spoke softly in my ear. "She's got great boobs, doesn't she?"

I looked at her warily. Her face showed nothing but bemused smugness. "Trish told me everything in the bathroom. I'm not mad at you, or her. Just next time, don't be afraid to talk to me, okay?"

"Okay." I slowly shook my head, chuckling. "You're really something special, you know that?"

"Just don't you forget it," she said with a sudden seriousness that quickly erased my smile.

Then she softened, took me by the hand, and led me back to the living room.

The ladies had started a movie, one that apparently featured several half naked, buff young male strippers. Nothing I was at all interested in watching of course.

Exhaustion crept over me as I finished my drink, and I decided it was time to call it a night. Although I realized I hadn't really considered whether I was welcome to stay there or not.

Jenna, noticing my yawns and drooping eyes, solved my problem for me. "Michelle, you don't mind if Tommy stays here tonight, do you?"

"Of course not," said Michelle. "I know he didn't drink much, but it's way too late for him to be driving home. Besides," she finished with a grin, "looks like you really wore him out."

Jenna giggled, then stood and pulled me up from the couch. "Come on, sleepy head, let's get you to bed."

I said goodnight to the other ladies, all of them hugging me and thanking me for a wonderful time. Despite being exhausted and completely spent sexually, the feel of their soft, warm, scantily clad bodies against mine was still a special thrill.

Trish was the last to hug me. "Thanks, Big Guy," she said softly. To Jenna, she said, "and thank you for...sharing. Are we good?"

"We're good," Jenna assured her. The two girls embraced warmly.

With that, we retired to Jenna's bedroom. Her bed was much smaller than mine, but I didn't mind. It just meant we had to sleep close.

Jenna snuggled up beside me and kissed me goodnight. "Thanks again for making tonight so special," she said sleepily. "Best birthday present ever."

That's when I remembered the gift I'd bought her.

It would have to wait til tomorrow. Jenna was already snoring.

Minutes later, so was I.

***

Morning came and went as we all slept through it.

But eventually, we all stumbled out of bed. Although tired and a little sore from being on my feet most of the night, at least I wasn't nursing a hangover. The ladies weren't as lucky.

I was glad I'd showered last night, because the bathroom had become Grand Central Station, with all of them jockeying for positions to shower, do their hair, or simply pee.

I did my best to stay out of the way and planted myself at the kitchen table, sipping a cup of freshly brewed coffee while watching them bustle around, getting themselves together.

The ones waiting to shower were still in their outfits from last night, and I had an interesting moment of confusion when Nikki walked by, appearing completely bottomless. Then I realized that the G-string she'd been wearing had simply disappeared inside her ample round ass.

I tried not to stare at her, or any of the other ladies too long. They didn't make it easy though, especially when Michelle came through next, fresh from the shower and wearing only a towel.

Tammy joined me in the kitchen. Pouring herself a cup of coffee, she sat across from me at the table, still in her lingerie as she waited for her turn to shower.

The bright sunlight shining through the kitchen window made her lace top even more sheer and see-through, making it impossible not to notice her perfect breasts, as they were completely visible through the top, including her puffy pink nipples. Tammy either didn't realize this, or didn't care.

I decided to break the awkward silence by making small talk. "So how did things go at the club last night? Did you ladies have fun?"

"It was alright, I guess," she answered. "Not as crowded as we thought. And not a lot of cute guys. The DJ was pretty good, though, and we danced a lot. You should have seen Jenna, though. She was killing it in that red dress. Every guy in there was trying to hit on her or dance with her."

"Really?" I smiled, imagining the scene.

"Yeah, but don't worry, she blew them all off."

"Oh I wasn't worried about that," I said. "We have a very open and honest relationship, and I trust her. But she's a beautiful young woman, I'd be surprised if the guys weren't hitting on her."

Trish smiled, "Yeah, I noticed you two are very...free, and trusting about things. I don't know if I would have been as comfortable as she was last night if you were my boyfriend; I'd probably have been very jealous."

I shrugged. "We communicated a lot; before, during and after. Making sure we were both okay with everything. That's really the key."

Trish nodded with a sigh. "You know, Michelle warned me beforehand you were an older guy, and I thought it was kinda weird. But seeing you and Jenna together, I get it now. I may have to start dating older men myself," she laughed.

Before I could reply, Jenna came in, fresh from the shower, hair still damp but fully dressed in a simple tee shirt and shorts. "Shower's open if you want it, Trish."

"Thanks," said Trish, then turning to me, "It was nice talking to you."

I again had to avoid staring too long as she stood, because her lacy shorts were just as sheer as her top, to the point I could clearly see her soft patch of natural blonde pubic hair over top the folds over her rosy pink vulva.

Jenna took her seat as she walked away. "She really does have a beautiful pussy, doesn't she?"

"How do you always catch me looking?" I asked with a grin.

Jenna shrugged with a smug little smirk. "You guys think we don't notice when you look. But we always do."

"Do you think Tammy noticed?" I asked, curious.

"Oh, she did," Jenna said, "you were too busy staring to notice the smile she gave me."

All I could do was shake my head and laugh. "Sorry, but it's not my fault there's so much eye candy around here."

"You need a distraction," Jenna grinned, "Come on, help me start cooking breakfast."

***

After breakfast, everyone pitched in to clean up the place. Michelle then gathered us all into the living room. "Before everyone starts heading out, we never got the chance to give Jenna her birthday presents."

Jenna sat in one of the single chairs as her friends went and got their gifts. I debated on getting mine, but decided to wait until later, when we were alone.

Jenna opened Trish's gift first. It was a box containing an assortment of art supplies; pencils, brushes, sketchbooks, etc. "I couldn't decide what to get you, so I went with something practical," said Trish.

"Thank you," replied Jenna, "I really appreciate it. Nothing wrong with practical."

"Open mine next," said Michelle, " it's practical, too."

Tammy and Nikki gathered next to Michelle, giggling with expectation as Jenna took the rather large box and began tearing off the wrapping paper.

It opened to reveal a variety of sex toys.

Jenna sorted through the contents, blushing furiously but also smiling and laughing as she pulled out the various items.

The largest was a pink wand massager with a bulbous, vibrating head. "It has multiple speeds and settings," explained Michelle, "a USB charging port so you'll never need batteries again, and it's hell of a lot more quiet than your 'Old Faithful.'"

Next was a toy labeled "Breathless." It was smaller than the wand, slightly curved, with a small hole on one end. "This one sucks your clit," said Michelle. "It also vibrates, but really it's all about the pulsing suction. You'll get some mind blowing orgasms from it, trust me."

"I have that one, too," Tammy interjected. "Personally, it's my favorite. I get multiples every time!"

The third item was a very realistic looking penis, complete with testicles and a suction cup base. It wasn't overly massive, perhaps six or seven inches long. "For when you really just need to be filled," said Michelle. "It doesn't vibrate, but if you combine it with the clit sucker, you're gonna need to change your sheets after."