The Florida Trip Pt. 01

"I've told you this," I said.

"I know," Alyssa said, like a child eager to hear her favorite fairy tale, "Tell it again."

"The four of us squeezed into that little car, yes," I said, "And I guess, being so close together, something happened."

"Do you think it'll 'happen' again?"

"Small car. Long drive. Maybe. Do you want it to?"

"You made it sound so exciting," Alyssa said, "All of you together like that. You wouldn't mind if we, like, fooled around a little, would you? Both of us, I mean. Nothing serious. Like we talked about before."

About a month into our relationship, Alyssa had told me about some hookup party her friends were having, and I'd balked. Alyssa got angry, gave me the whole "we're dating, but you don't own me" speech. If I couldn't handle it, well, there were plenty of men ("grown-ups" was the word she used) who would.

We were clearly at a breaking point. So, with nothing left to lose, I'd told Alyssa about the baseball trip. How I'd gone on this wild journey with three women and no strings attached. And I told her the truth, that at the end of the trip I'd learned that I wasn't meant for long-term relationships. That having fun was more important than having feelings.

I got so into my story, I was sure it was the last conversation I'd ever have with Alyssa. Instead, she seemed impressed. Like she was seeing me in a totally different way. And so we agreed that, in the future, it was fine for both of us to fool around. With caveats, of course.

I'd never had an 'open' relationship, so Alyssa helpfully explained the ground rules. The big one, like most things where sex is involved, was consent. No one could do anything without their partner's permission. We had a whole big talk about it and afterwards I felt both very mature and also very horny.

Despite all that setup, neither of us had done anything. In fact, since we'd started dating, I'd only been with Alyssa and she'd only been with me. But that door had been left open with the understanding that Alyssa would, again, want to step through it. And I could either come along or be left behind.

I looked over at my redheaded girlfriend. She was super pretty and so out of my league. Alyssa smiled at me, coyly. She wasn't really asking me a question.

"I don't see any harm in doing a little bit," I said, "So long as everyone is into it."

Alyssa cheered and clapped a little. She leaned over and kissed me on the cheek. The peck on the cheek turned into a kiss on the lips. Deftly, Alyssa slid her hand down, under the waistband of my pjs, and found my cock. The redheaded girl smiled at me -- that dangerous, sexy grin -- and stroked me hard.

Alyssa slid her bottoms off and climbed up on top of me. Another kiss on the lips. Alyssa didn't even bother taking my pants off. She just steered my cock to her waiting pussy. Slowly backed down.

"I want... I want Julia to lick my pussy while I ride your cock," Alyssa said. My eyes went wide, and I looked over at our door. It was shut tight, but still. I knew Alyssa was bi. She'd told me she had a crush on my roommate (who could blame her, really). But I didn't expect it all to come out like this.

"I'd think that's up to Julia," I said.

"Ohhhhh FUCK!" Alyssa said, sliding all the way down my shaft. She leaned back and started to rub her clit.

"Yessss...OH! That fffffeels so good," Alyssa said. Her eyelids fluttered shut and I thought she might be imagining it right there -- my athletic roommate licking my girlfriend's snatch while she rode me.

"I think... Oh I think I want to lick Kelsey's pussy while you fuck her, too," Alyssa said. She was rubbing even faster now. Her hips bucking. Head lolled back.

"You haven't even met Kelsey," I said.

"Going to be so SO gooooood..." Alyssa said. Her body crested and she froze. Tits pointed to the sky and shaking. Alyssa leaned forward. She hung her breasts over my head, inviting me to suckle. I took her little pink nipple into my mouth. Tried my best not to bite down while Alyssa began pumping her tight ass up and down. Working my cock. The dregs of her own orgasm now hungering for the beginning of mine.

"What about you?" Alyssa asked, "You want to fuck Sarah while you lick my little pussy? Oh, I bet you do."

The picture filled my mind as soon as my girlfriend said it. The image of it gripped me as tightly as Alyssa's sweet snatch squeezing at my cock. I groaned.

"That's it," Alyssa said, "Attaboy. Think about it. I'm riding Julia's face while you're plowing me from behind. Little Kelsey is licking your balls and all you're going to do is... CUM! Oh FUCK!"

My cum raced up my shaft and filled Alyssa's pussy. She'd barely ridden my dick at all. She'd given me more than I could take, all that talking. Pleasure exploded out of me as I blasted into my girlfriend's snatch.

Alyssa started to laugh. Rocking back and forth on my cock as she milked me for every last drop. My dick went soft and Alyssa fell off to my side. Gasping. She reached for a tissue to wipe herself off. Handed me one, as well. Still chuckling.

I rolled over and kissed Alyssa on the mouth. She grabbed my cheeks and held me there, staring right at me with her pale green eyes.

"This trip is going to be AWESOME!" she said.

*

That night, I dreamt about being back in Julia's Beetle. On the baseball trip. Nothing sexy at all was happening. Instead, I found myself in the backseat, smushed against the window with nowhere to go. Julia honking the horn. Beep beep beep! I twisted and bent in my seat, trying to get comfortable. It was hot and the air was short. Gasping.

Burning.

Beep! Beep! Beep!

I woke up with my back aching. My phone alarm blaring. Just the idea of being in Julia's little car had given my body flashbacks. I switched off the beeping alarm and lay back. Tried to catch my breath. God -- what was going to happen to me when I was actually in the car? The last time there'd been four of us and we'd barely fit. Now we were five. Alyssa and I'd fantasized about fucking around on the road. How were even going to fucking fit?

My girlfriend rolled over and rested her head on my chest. "How did you all fit in that little car?" Alyssa asked. Clearly my psychic abilities had reached a whole new level overnight.

"Like I said, it involved putting our parts into each other's parts. Purely for convenience of storage," I told her.

"Uh huh."

We slowly rolled out of bed and got dressed. The sun wasn't even up yet, but we couldn't bear the thought of turning on a light. When we walked out of our room, we saw that Julia's door was already open. Her luggage was gone.

We didn't even bother with coffee. We just clambered down the stairs, suitcases bouncing behind us. I was nauseous with the early morning wake up. The adrenaline of the upcoming adventure. The fear of how overstuffed Julia's Beetle would be.

But when we got outside -- under the cold, still-dark skies -- Julia's car was nowhere to be found. Instead, my cute roommate was standing there on the sidewalk, smiling from ear to ear.

"I have a surprise for you guys," she said.

"If it's lube we already brought two tubs-worth," I said. Alyssa punched me in the arm. Julia turned to the side and pointed at the car parked across the street from her. Some shiny, white van-like thing that none of us would be able to afford for another ten years post-graduation.

"Did you hire a limo?" Alyssa asked.

"It's my brother's. He said we could use it," Julia said. She ran over and posed in front of the car, arms outstretched, like she was giving it away on a gameshow. "Isn't it great?"

Our new ride was a Honda Odyssey, bright like it was right off the lot. It was a monolith. A monument to the momentousness of our trip. It shone like a pale beacon under the starlight.

"I told my brother about everything with Brandon and the trip and how my little Beetle was barely adequate, and so he drove his car up here last night." Julia's eyes were shining as she said it. Her voice thrummed with excitement. "Isn't he like, the best brother ever?"

We had to agree that he was. We put all our things into the trunk and the back was still so empty I almost ran upstairs to grab more stuff before Alyssa stopped me. The back seats had more legroom than our living room couch. It was like moving from a studio apartment to a mansion. Almost overwhelming to find ourselves with so much space.

Julia grabbed the wheel, of course, while Alyssa took shotgun. I got in back, but it was hardly a sacrifice. More like being chauffeured than suffering in the shit seats.

"It's really comfy back here," I said, "Maybe a bit too comfy."

"Looks perfect to me," Julia said and stared back at me, knowingly. She didn't need to speak the warning for me to hear it clearly.

*

We drove down to New York City in darkness. Near silent. Like sneaking into the city. I dozed in and out through most of it. By the time I was wide awake again, we were turning off the highway. The sun sneaking slightly above the horizon.

As we slowly wended our way around Manhattan, it began to rain -- a morbid, drizzly thing. One last eff you from the northern weather gods. With the wet and the early morning sun, I could hardly tell one street from another. But Julia navigated it with ease, taking every turn with absolute assurance.

Then we slowed and I saw her standing on the side of the street: Sarah, the sexiest woman I'd ever seen. She was next to an anemic looking tree, under a blue umbrella, wrapped in a tan heavy coat. She could have been wearing a burqa -- I felt like I'd have recognized her immediately.

I felt my heart ache a little, seeing Sarah again. Then that desire got washed away by a wave of guilt. My girlfriend was in the car with us, for God's sake. All other conversations aside, I couldn't just openly perv on another woman.

Julia double-parked in front of Sarah's apartment. We opened the doors and climbed out. I was stiff in more ways than one, and I slowly made my way over to Sarah. We hadn't spoken in months. Would this be as awkward as I feared?

"Ben!" Sarah wrapped herself around me. Her ample chest pressed into me through all those coats. I could smell her vanilla perfume. Feel the warmth of her cheek against mine.

Sarah had grown her light brown hair a bit longer. Her face looked a little thinner, like stress had worn her down. But her body, wow, it was still as amazing as I'd remembered. Maybe even a little better. Curves in all the right places.

Sarah pulled back and smiled. Those deep brown eyes shining back at me. God, even with the obvious exhaustion -- the tension -- that girl looked so good. Oh so sexy Sarah. Being in her arms now, it felt better than I'd ever remembered.

"It's so nice to see you," Sarah said. She started to move forward, like to give me a kiss.

"Hi, I'm Alyssa," my girlfriend said, getting between us. The redhead extended her hand and Sarah shook it. "I'm Ben's girlfriend."

"It's nice to meet you," Sarah said, genuinely.

"Uh huh."

Sarah turned and found Julia, hugging her with almost the same excitement as she'd shared with me.

"You look good," Julia said, "You lost some weight?"

"Just a little," Sarah said, "You lost your glasses!"

"I got contacts," Julia said.

While the girls talked, Alyssa and I started loading Sarah's suitcases. But as we did, I felt another pair of eyes on me. I looked up and saw a young woman staring at me, standing by the brownstone steps.

This had to be Sarah's younger sister, Chloe. She was wearing a purple raincoat that went down to her waist, a pair of tight blue jeans, and tan strappy sandals. Wishful thinking, I suppose.

I went over and introduced myself. She was slightly shorter than Sarah. Slimmer in face and build. And chest. But the resemblance was still uncanny.

Then Chloe turned and reached down to get her suitcase and Oh My God. While Sarah's backside was merely nice, Chloe's was clearly incredible. Round and thick -- even under denim it looked amazing. I say this as someone who is usually more into the T than the A: Chloe had an ass for the ages. Almost the perfect upside-down heart shape and plenty prominent.

I stared, dumbfounded for a moment. I felt Alyssa brush against me none too subtly. I startled and turned to pick up Sarah's suitcase. Like that had been my intention the whole time.

"Amazing, huh?" Alyssa asked, following me back to the trunk of the Odyssey.

"Yeah, look at all the room we still have back here," I said. Alyssa waggled her finger at me and skipped away.

"It is a really big car," Sarah said, almost wistfully, watching as we reorganized everyone's things.

"I know, isn't it awesome?" Julia said.

Sarah started to climb into the backseat, but Alyssa stopped her.

"I want to sit with my boyfriend," she said. Sarah nodded dumbly.

"Come sit with me, Sar," Julia said, "We have lots to catch up on."

I climbed into the back with Alyssa and Chloe. Sarah's younger sister took the third row to herself while my girlfriend sat in the bucket seat next to me. There was less room for all of us in my apartment, I swear.

Julia got behind the wheel and keyed the ignition. As we started to pull out, Alyssa gave me a wicked look. Before I could blink, the saucy redhead leapt into my lap.

"Oh no you don't!" Julia said, slamming the brakes. She adjusted the rearview mirror and looked back at us, sternly. "This is my brother's car and I promised he'd get it back in one piece. No food, no drinks and definitely none of our usual... shenanigans. We get one stain in this car? He'll kill me. And I'll take all of you idiots down with me. Understood?"

Alyssa glared up at the mirror for a moment, like she might put up a fight. But then she meekly slid off me and settled into her own seat. "Understood," she said, pouting.

"Shenanigans?" Chloe asked.

"Julia's rules," I said, "No shenanigans, hootenannies, or ragamuffins allowed."

"I knew I should have left you in Buffalo," Julia said. She put the car back in drive and peeled off.

*

The next stop was New Jersey so we could meet up with Kelsey and her boyfriend, Kevin.

We went over the George Washington Bridge, as empty as I'd ever seen it, and got onto the Parkway. Soon we were slowing, once again, into a very different neighborhood than the one we'd gotten Sarah at. Tall old oaks and even larger houses. Bright white shutters and shining, obsidian BMWs.

It was weird pulling up in front of Kelsey's place. I'd spent half my high school years there, hanging out with her older brother, Jim -- my former best friend. He and I had barely spoken since the baseball trip. We weren't completely on the outs, but the friendship was clearly terminal and neither of us was interested in taking the time to resuscitate the patient.

I got out of the car and pulled my jacket tight across my chest. The weather had cleared, and the sky was bright, ice blue. Sarah got out of the other side of the car and we both walked up the driveway to Kelsey's door. I'll be honest, my heart was pounding in my chest. Seeing Sarah again had already gotten my engine going. My anticipation for Kelsey had me absolutely racing.

The door swung open and there she was. Like I said, Sarah was the sexiest woman I'd ever seen. But Kelsey was the most beautiful. Time dulls things. You tell yourself that nothing is as intense as you remember it. When I saw Kelsey in the open doorway, it all came flooding back.

Blonde, incredible Kelsey. I mean, wow. She'd cut her blonde hair to shoulder length and it looked good, accentuating the almost impossible beauty of her face. Kelsey was no Sarah in the curves department, but it seemed like her chest had filled out a bit since I'd last seen her. She was wearing a bright yellow sweater and dark blue jeans. Dress-down casual Kelsey looked better than most people did in their finest.

She gave us both a tight hug. We stepped back and stared at each other, grinning like idiots. Kelsey's bright blue eyes shone, like they could warm the world. Lord knows I started to feel a bit sweaty just looking at her.

"I can't believe this is happening again," Sarah said.

Kelsey stiffened slightly. "My boyfriend, Kevin, is upstairs finishing off a shower," she said.

I looked over at the pile of suitcases sitting behind Kelsey in the foyer. "Let me help load your car," I said.

We each grabbed a bag and went down the front steps. As soon as Kelsey walked onto the lawn. Julia shrieked like a pre-teen girl at a Taylor Swift concert. I never knew my tomboy roommate could make such a sound.

"Little slut!" she screamed and raced up to Kelsey, wrapping herself around the blonde girl like a snake on its prey, practically tackling her to the ground.

"Be quiet!" Kelsey said, then more softly, "Shut up about that stuff, seriously."

"What, are your parents home?" Julia asked.

"No, it's just... Kevin," Kelsey said, "He thinks I'm a nice, wholesome girl and I don't want you guys convincing him otherwise, OK?"

Julia nodded understandingly, but I could see a little bit of disappointment in her eyes as she let Kelsey go.

Alyssa and Chloe heard the commotion and came out of the car to say hi. I swear I saw Alyssa go weak in the knees when she saw Kelsey for the first time.

"I thought you were exaggerating before," Alyssa whispered in my ear, "I mean, Sarah's cute and all, but Kelsey? Holy fuck! I think you might have sold her short a bit. I didn't think there were people who really looked like that without retouching."

After I introduced Alyssa to Kelsey, Chloe went up to her to say hello. "Wow," the beautiful blonde said, "You've really grown up Chlo." Sarah and Kelsey had been friends as kids, so clearly Kelsey knew Sarah's younger sister, too. They gave each other a tight hug.

"Seriously, you look really good," Kelsey said. Chloe blushed a bit and smiled. "I didn't realize you were coming. What happened to Julia's boyfriend? Brandon?"

"He's dead, hopefully," Julia said. Kelsey's eyes went wide. Still a bit innocent, I suppose. "We broke up. Well, he broke up with me. Ben scared him away."

"I did no such thing," I said, as if I had no idea what she was talking about. But deep down I felt like I did know, and it scared the hell out of me.

"Well anyway, he sucks," Julia said.

"I think we can all agree with that," Sarah said.

Finally, Kevin came down the stairs, carrying the rest of the suitcases. He looked exactly like the pictures I'd seen of him -- tall with light brown hair, jutting cheekbones, and big blue eyes. People like this weren't supposed to exist, but here they were in suburban New Jersey, willing to be spotted with us lowly peons.

Kevin had a firm handshake and a boyish, charming smile. Damn, Kelsey had done good. I could tell my girlfriend felt the same way. Already flushed from meeting Kelsey, she went practically ruby red after Kevin gave her a hug hello.

"Wow," she said to me, "I mean, wow."

"I know," Julia said, "there's still so much room in the Odyssey. We could probably all go in the one car."

"That's OK," Kelsey said, "I think it'll be easier if I ride with Kevin in his car. That way we can switch things around, if needed. Besides, why crowd in if we don't have to?"

"Why indeed," Alyssa said, grumbling to herself.

With everything loaded, we reassumed our seats in the Odyssey -- Julia driving with Sarah up front and me, Alyssa, and Chloe in the back. Kevin slammed the trunk of his little blue sedan and climbed into the car with Kelsey. He leaned out the open window and gave us all a thumb's up.

We were finally -- FINALLY -- ready to begin our road trip.

*

Julia got back on the highway, heading south to hopefully warmer weather. We spent the first few hours of our epic drive ice cold. Like we were all starting from scratch. Julia blasted the tunes. I stared out the window. Lumps of grey snow piled everywhere. Trees looked more like twigs. No one sat on each other's laps or even gave each other a longing look. We were five friends, siblings, and lovers on a long drive. Suddenly feeling like strangers.