The Jenna Arrangement

"Happy birthday, Tommy!"

Groggy as I was, I couldn't help but smile as Jenna and Trish entered the bedroom. Jenna carried a serving tray with a plate of bacon and eggs, while Trish held a mug of fresh brewed coffee.

Even more invigorating than the delicious smell of java were the outfits my two young lovers were wearing.

Jenna wore an adorably sexy top that I can only describe as some type of cropped babydoll - bra hybrid. The diaphanous white fabric perfectly conformed to her pert breasts, trimmed underneath the cups by a lacy white skirt with frilled pink edging. Her boy short style bottoms were just as see through, leaving little to the imagination.

Trish looked stunning as well in her navy blue teddy, the swoop neck open all the way to the naval. Delicate lace framed the edge, highlighting her ample cleavage.

Jenna moved to one side of the bed, carefully placing the tray of food over my lap. Trish approached from the other side to hand me the coffee. "Cream, two sugars, just as you like it."

"Aw, you remembered." It was actually cream, one and a half sugars, but I wasn't about to get nit picky over it. Especially since I was getting a very intimate view of her luscious breasts as she leaned over to proffer the mug.

As I enjoyed my breakfast, I remarked on just how special this birthday was. I'd "celebrated" my previous one on my own; no friends, no family. I'd initially met Jenna in February of last year. But my birthday falls in April, and I hadn't seen her again until that May.

Since then, though, we'd spent as much time together as two people could, given our situations. And had some truly memorable adventures along the way.

And by the looks of them, the ladies seemed keen on continuing those adventures. Like, immediately. Jenna was already tugging at my pajama shorts.

"I can't believe I'm saying this," I laughed as my quickly swelling cock sprung free, "but I just finished eating! Maybe we need to wait a bit, let me digest."

"Oh relax, cowboy," Jenna chided playfully. "That's just for swimming. And besides, for our first gift of the day, you don't have to do anything besides lay back and enjoy."

There was certainly no further argument from me as the girls climbed on to the bed and began smothering me in kisses, kisses that quickly worked their way down my body, their intended target now fully engorged and twitching in anticipation of their arrival.

Soon enough, lips found my hot, hard flesh, joined quickly by tongues, dancing along the length of my shaft, fluttering and swirling over the head.

Raising my head from the pillow, the view was breathtaking: Two adorable, happy, smiling faces, ravishing my cock with zeal. Two pairs of eyes, Jenna's emerald green,Trish's deep brown, gazing up at me with love and lust. It was enough to make an atheist feel he'd died and gone to Heaven.

It was also almost too much. "Ladies, if you're looking for more, you'd better slow down. You got me right on the edge here!"

Jenna pulled her mouth from my cock and flashed me her trademark grin. "Oh, really? I know just what'll push you over, then."

In a flash, she was moving, her lithe body repositioning over me to straddle my face Reverse Cowgirl style. Her pussy was clearly visible through the transparent shorts; pink and puffy and very wet with her arousal.

Jenna lowered her ass and I buried my nose in her, breathing in her scent. With a yank, I pulled the loose fitting cloth aside and plunged my tongue deep inside.

Jenna squealed with delight before leaning down to Trish, who was currently bestowing her vaunted deep throat skills upon me. My cock was now a time bomb, ticking away the final moments before the inevitable explosion.

Sensing I was close, Trish pulled off. Grabbing my spit slicked shaft, she pointed it towards Jenna, who took the head between her lips, applying suction while Trish stroked.

I quickly lost control, almost bucking Jenna off me as I writhed beneath her. She somehow managed to hang on, keeping her lips tight around me as I erupted multiple blasts into her mouth.

My body continued to quake uncontrollably even as Jenna finally released me. When she and Trish moved to lay beside me, I simply held them tight, sharing soft, intimate kisses.

When at last I regained the ability for rational thought, I broke the silence. "Ladies, thank you. So, so much. That was truly incredible."

"You're welcome," they replied in tandem.

"Maybe after a little break, we can continue this," Jenna offered. "Plus, second surprise, I also have dinner reservations for us later tonight. That steak house you kept saying you wanted to check out. I'll finally get to wear that black dress you bought me for my birthday!"

"Are you sure?" I couldn't help but ask. "That place is... a little pricey."

"Yes, I'm sure," Jenna said firmly. "Now stop being a cheap bastard. Besides, Trish and I are paying for it, not you."

"Fine." I knew better to argue with her, especially when she had that look in her eye.

Sitting up, I positioned myself on my knees at their feet and looked down at my two lovely, scantily clad beauties, laying so comfortably together.

"Well, looks like we have some time to kill before our dinner date then," I grinned at them. "In the meantime, I'm in the mood for a snack."

Taking the knees of each girl, I parted their legs.

"Now... who wants to go first?"

***

Dinner was amazing; the company, even better. We turned quite a few heads as we made our way to the table. Well, it was more likely the girls drawing the attention than me. But one of my favorite things about going out in public with Jenna and Trish was the stares we'd get from horny, jealous guys and curious women who were probably wondering just what these beautiful young ladies saw in me.

By the time we'd returned home, we were all more than a little stuffed. Stripping out of our dress clothes, we collapsed to the bed; me in just my boxers, Jenna and Trish in tee shirts and panties.

As sexy as the situation was, the three of us were exhausted, having spent most of the morning and afternoon fucking each other's brains out. So instead we just snuggled, enjoying the quiet intimacy.

Quiet, that is, until Jenna burped. "Oops," she giggled. "Pardon me."

"That's it, we're breaking up," I smirked, with more than a hint of sarcasm.

"Oh, REALLY?" Jenna tried her best to look angry, but I was now much better at being able to tell when she was just playing. "Well, then. Guess it'll just be me and Trish from now on, right Trish?"

Trish suddenly looked sad. "Um, speaking of that, I suppose now is as good a time as any to talk to you guys."

"What's wrong?" Jenna asked, concerned.

"Nothing," said Trish, her eyes welling up. "Nothing is 'wrong' per se, just... okay fuck it, just out with it I suppose. I met someone."

I'm not sure who was more surprised, me or Jenna.

"Really? Jenna gasped. "That's... well, isn't that a GOOD thing? A good thing that you didn't even tell your bestie in the whole world about already, but still... When? Where? Who...?"

"Jenna, slow down," I cautioned. "Let her talk."

"Oh. Right. Sorry, Trish."

Trish managed a smile despite her otherwise glum appearance. "It's okay. And I'm sorry for not bringing this up earlier. But I wanted to wait until... Well, I'm not even sure, honestly. But I guess until I was sure it could go somewhere."

"Go somewhere?" Jenna looked awestruck. "You mean like, get serious? You're already serious about this guy?"

"Yes. No. I don't know!" Trish looked flustered. "I just know I like him. A lot. There was a spark. And I'm pretty sure he felt it too. So far it's just been lunches in the cafeteria and a couple of coffee dates. But we're going out officially next weekend. To a party. Not some drunken frat party, but a get together at his place, a mix of his friends and family. They're having a barbecue and he actually wants me to meet everyone and..."

Trish could no longer contain her emotions, simultaneously laughing and crying. "No guy I've ever dated has wanted me to hang out with his friends, let alone meet his family! And we haven't even, you know... well, okay, some heavy kissing, but..."

"But, isn't that a good thing?" I asked. "It sounds like things are going well. So why are you upset?"

Trish seemed unable to look either of us in the eye. "Because if things do get serious, it means I'd have to... to end things with you two."

"Ah," Jenna nodded. "I can see how things could get... complicated there. But hey, don't feel bad about it. Just go with your heart. Tommy and I will understand, whatever you choose."

Taking my hand, Jenna turned to me for confirmation. "Right?"

"Of course," I agreed. "Look, Trish, I'm not gonna lie and say we won't miss sharing our bed with you, but it won't mean we can't all stay friends. Jenna and I just want you to be happy. Whatever you feel you need to do, we're here for you and support your decision."

"Thank you, both of you." Trish looked relieved. "I was really just afraid of hurting you guys. I love you both, very much. But if I'm being honest, I still sometimes feel like a third wheel. I mean, no offense, Tommy, I know you do your best, but it's plainly obvious who you have deeper feelings for, and it's not me. And that's fine, I knew that going into this. But I kinda feel like I need my own thing, someone who puts me first in the relationship, ya know?"

"Hey, you don't have to explain yourself to me," I told her. "I'm happy you may have found someone who gives you what I can't. And I hope it works out, I hope you find happiness with him."

Trish fell into our arms and we embraced in a group hug. "I love you guys," said Trish. "Thanks again for being so understanding and supportive. And hey, it's still very early in this relationship; I have no idea if it'll truly work out. I just know I want to give it a chance. And to do that, I need to focus on building it with him, not splitting my attention... and my affections. If that makes any sense."

"Makes perfect sense to me," Jenna assured her. "But I do have one more question. Well no, way more than one. But let's start with... What's his NAME?"

Trish couldn't help but laugh. "Miguel. His name is Miguel. We met on campus. It's a funny story, actually..."

As Trish spoke of him, Jenna constantly prodding her for more details, I could see it in her eyes. She was definitely smitten.

While part of me was sad that I'd likely no longer be intimate with Trish, I was mostly happy that she'd found someone, and wished her all the best with it.

***

The next morning, Trish was up and out early. Now that she'd fully opened up to us about her new boyfriend, she'd decided to call him and meet for breakfast.

That left Jenna and I alone to sleep in and cuddle.

"Guess it's just you and me again, cowboy." Jenna's breath was warm on my neck as she spoke. "Disappointed?"

"Not at all," I answered firmly. "You've always been more than enough for me, Jenna. Sure, I really care for Trish, and she was certainly a wonderful bonus to our relationship, but you're the one I fell in love with, the one person I truly want to be with."

"Mmmm," Jenna purred, "that's the kinda sweet talk that'll get you some morning sex."

With a giggle, her nude body moved over mine, and we became one. It was astounding to me that, after not quite a year together, we still felt so connected, so in tune when we made love. Every time entering her felt like the first time. And every orgasm? The best I'd ever had.

During an interlude, Jenna was again snuggled beside me. Lifting herself up on an elbow, she looked down at me with those brilliant green eyes. "So I was gonna bring this up last night before we got sidetracked by Trish's big announcement. After that, I figured it'd be better to wait."

"What's on your mind, darlin'?"

"Well, I've been thinking a lot about something we discussed a long time ago and decided I'd be interested in trying it."

"Butt stuff? Finally?" I quipped.

Laughing, Jenna smacked my chest playfully. "No, you jerk! I meant the swinger's club. You remember? We talked about going sometime, watching other people fuck..."

Her face flushed with a mix of embarrassment and excitement as she finished. "... letting people watch US fuck."

My cock, which had been resting comfortably at half mast during our little break in the action, was already starting to swell. "You're serious?"

"Yes," she nodded. "But right up front, I'm not looking to fuck any other guys. We can talk about you, what your options are, but..."

"Jenna, stop." Sitting up against the headboard, I put my arm around her and pulled her to me. "Listen, I'm not interested in going there to have sex with strange women. You're the only woman I want to be with, Jenna."

"And Trish if she decided to rejoin us," Jenna interjected playfully.

"Okay, fine," I chuckled. "And Trish. But seriously, Jenna, if we decide to do this, we'll need to discuss boundaries, what we are comfortable with, and what we're not. But please understand: I'm not interested in hooking up with a stranger. If WE ever decided to bring another person into our bed again, it would have to to someone we both cared about and trusted."

Jenna let out a sigh of relief. "I'm so glad you said that. I know we've had our fun playing here and there, teasing others, and of course sharing Trish. But she was a special exception. Someone we both, as you say, trust and care about. Someone we love."

"So we're in agreement there," I said. "That doesn't mean we can't have fun, interact with others. But again, how far we can go should be established before we set foot in the door. That said, my biggest fantasy when it came to taking you to a swinger's club was showing you off, making other men jealous of the beautiful young woman I was with. Having them want you, but not being able to have you."

I moved up and over her, positioning myself between her open, inviting legs. "I want them to watch while I fuck you, watch as I make you moan and squeal, wishing it was their cock making you scream, not mine."

Jenna pulled me to her, guiding me in. "Ohhhh, fuck yes! I'd be your little sex toy, your plaything, your slut! But only for you, Daddy!"

Her lips found my ear, her teeth nibbling at my lobe. "I'll be your love's whore."

***

Later... much later... we found ourselves at my kitchen table, eating a long delayed, much needed breakfast. As we ate, we discussed the more practical details of our excursion.

A quick Google search revealed the club I had heard about many years ago was indeed still open and thriving. Since it wasn't very far, just over the bridge into the city, we decided taking an Uber was our best option. Although Jenna was still a few months away from being able to drink legally, she occasionally enjoyed smoking a little weed, especially if she wanted to relax and loosen up a little.

And while I wasn't a big drinker or smoker, I might want to indulge a little myself, although of course I'd need to be cautious, lest it affect my... performance.

Now that we'd finally agreed on the idea, we were very excited, and decided not to put it off any longer. A quick comparison of our calendars showed we were both free the coming Saturday night, and so I immediately purchased the tickets.

Jenna was only slightly miffed. "Hey! I was supposed to pay! Your birthday, remember?"

"Ah, come on," I laughed, "it's not like they were that expensive. But tell ya what; you pay for the Uber, then."

"Deal." Jenna practically squealed with excitement. "I can't believe we're actually doing this! I'm gonna go shopping this week, find something special for the occasion."

***

The week dragged by, as time tends to do when you have something exciting coming up.

Jenna spent Friday night at my place, and while we'd at first made a big show about "saving our energy" for the following evening, that pretense quickly fell by the wayside when we crawled into bed, attempting to get a good night's sleep.

The next morning was only slightly less difficult for us to keep our hands off each other. But while we'd engaged in our usual morning snuggles and even showered together, we both agreed to save our stamina for the club.

As we prepared for the evening, we again spent a lot of time discussing both our boundaries, and what we each were hoping to get from the experience.

I found it comforting to realize we were very much in agreement, and that neither of us had any reservations. We trusted each other implicitly and knew that if there was ever any jealousy or discomfort, that we could talk about it and work through it together.

Finally, it was time to get ready. There was no real dress code for the place, especially since many eventually wound up naked anyway. Still, Jenna and I had decided that, at least initially, we'd dress to impress.

Jenna had bought something she planned on changing into, something she wanted to reveal as a surprise later. But still, she needed something to wear there, and went with the form fitting red dress she'd picked out last year for the Girls Night party with her friends. She looked stunning in it, especially with her hair and makeup done. And of course there were matching shoes she half jokingly referred to as her Fuck Me Pumps.

I cleaned up pretty well myself, freshly shaved and having gotten a haircut earlier in the week. Jenna had helped pick my outfit; A lightweight black blazer over a form fitting red tee-shirt that matched her dress perfectly. Freshly pressed blue jeans and a pair of knitted Oxford dress shoes completed the ensemble.

Giving myself a look over in the mirror, I was, for a rare change, pleased with what I saw. I'd been keeping up with my routine at the gym, and also been eating healthier, thanks mostly to Jenna. While I still wasn't in perfect shape, I'd certainly managed to lose a few pounds and tone myself up enough that I might even be able to take my shirt off and not feel self-conscious.

Having had two college age lovers had certainly boosted my self esteem, but I'd always still have insecurities about my looks.

Not tonight though, I promised myself. Tonight, I was a fucking rock star.

Jenna agreed. "There's my handsome stud." Her arms enveloped my waist as she came up behind me. I was too tall for her to look over my shoulder, so instead, almost comically, she popped her head around my right shoulder to take a better look at me in the mirror. "Damn, but you look good. I'm gonna have to beat all those MILFs and Cougars off with a stick!"

I couldn't help but laugh. "Ah, so you're saying it's only the older women there you're worried about?"

Jenna held me tighter, her hand moving between my legs as she responded. "Older, younger, doesn't matter. They're all gonna want you. Want this. But they gotta go through me first."

I turned to face her, putting my arms around her as well. "Why Miss Sinclair, is that jealousy I hear? And while I appreciate the compliment, the truth is it's gonna be me having to fight off every horny guy in the place trying to get to you, darlin'."

Jenna blushed but smiled. "Don't you worry, they can look, but can't touch. And I have an idea that'll send exactly that message."

"Oh really? And what exactly did you have in mind?"

Jenna leaned up on her toes and kissed me. "You'll see."

I considered pressing the question, but decided to let her have her secrets for now.

***

The Purple Orchid Club was already filling up as we arrived, but the line moved quickly enough.

We were required to check our phones at the entrance, and there was a quick inspection of Jenna's clothing bag as well as her I.D. They checked mine as well, more of a formality really, then put an ink stamp on my hand that I would show the bartender to verify I was old enough to drink. Like that really might be in doubt.