Part three of a nine part series! You'll probably be happier reading parts one and two before heading into here. Just a reminder, everyone in this story is over the age of 18.
*
I woke up with my cock nestled firmly in someone's bottom.
Still in post-orgasmic stupor from the night before, I naturally assumed I was in bed with the beautiful, buxom Sarah. We had 'acted out' together the night before, after all. So I did what any right thinking male would do in that situation, I grabbed her hips and ground myself into her. Guys think this is romantic, you know.
But when my hands wrapped around Sarah's ample ass I realized, it wasn't all that ample after all. It was more taut. Muscular.
I realized, then, that I must be pressed up against Kelsey. The thin teenager's bottom would absolutely be so tight, so tiny. If anything then, I redoubled my efforts to rub. After all, Kelsey had been the more enthusiastic of my two playmates the past few days. I expected her to push back ardently and, of course, she did.
But then another thought entered my sleep-addled brain. This push felt far too aggressive for the tiny, virgin Kelsey. She was certainly assured but never so strong. The person currently engaged in rubbing her backside against my steely member was driven, athletic. Not at all like Kelsey's small, supple body.
And then, all in a rush, I remembered.
I was not sharing a bed with the terminally sexy and supposedly unavailable Sarah with whom I'd started some sort of strange, exhibitionist-only orgasm club. I was not under the sheets with the teenaged, nubile, probably a little too excitable, supermodel-esque Kelsey who had begun her own sexual exploration society with me the previous day.
Oh no. I was in bed with the supposedly "safe" member of our frolicking foursome: Julia, my roommate, best friend, and apex tom-boy. The only girl I hadn't been with on the trip -- could never be with -- and I was currently grinding on her hardcore.
And she was grinding back.
By the time I was putting it all together, Julia was already pulling away. She slid out of the bedsheets and stood over me, a goofy grin belying her otherwise stern stare.
"Well that was interesting," she said.
"Sorry," I said, "I thought you were..."
I looked over to the other bed where bffs Sarah and Kelsey were still asleep, snuggling in a way that was suspiciously suggestive to my male eyes.
"Someone else?" Julia asked. She waggled her eyebrows at me. Her little tits did their best to wag along with them.
She had me in a bind. I couldn't admit that I thought she might be Sarah or Kelsey. Everything going on in the backseat of the car (and at baseball games, and the hotel hot tub...) was still supposed to be a secret. I wasn't sure how Julia would react to knowing I had turned our baseball road trip into a rolling orgy, but I was pretty sure it would be in the realm of horrific, friendship-ending, freak out.
"Anna," I said, name-dropping my ex-girlfriend, "We used to spoon in bed, in the mornings. I guess I just..."
"It's OK dude," Julia said, punching me on the shoulder, "We're cool."
She went over to her suitcase, grabbed a bunch of clothes, then went to the bathroom to get changed.
"Was kinda nice, actually," she said, almost to herself as she stepped away. For all my talk about Julia being a bit of a boy at heart, she was definitely a woman. One I wouldn't mind slipping out of those t-shirts and...
Nah. Who was I kidding? She'd suplex me sooner than kiss me. Besides, I thought -- looking at the two beautiful women wrapped around each other in the neighboring bed -- I had more than enough to keep me busy.
*
Our Midwest Baseball Tour's next stop was a night game at Wrigley Field, which gave us plenty of time to explore Chicago. This meant no more backseat fun for me, at least for a little while.
But a day of non-driving didn't mean we would be slowing down. According to Sarah, she and I now had a regular after hours appointment for an evening of look-but-don't-touch in the hotel hot tub. And I'd have been shocked if Kelsey didn't formulate some follow up to the previous day's debauchery.
As I got dressed in the bathroom, I could hear the three women talking in the next room. I didn't know what I was in for, but I was definitely up for it.
*
After so much time riding in the car, we all agreed to walk up to Lincoln Park Zoo. It was early morning on a weekday, the traffic was heavy, but the sidewalks were mostly empty. It was our first warm morning of the trip, and the sky was almost as blue as Kelsey's eyes.
As expected, Sarah was acting especially distant -- her standard M.O. for mornings after. Her guilt had a definite wax and wane -- strongest after waking up to the cold reality of what she'd done the night before, then slowly degrading as the day went on. She had barely said hello to me that morning and now was walking well ahead with Julia.
Kelsey, on the other hand, was almost too much. Half the reason we were lagging behind was I had to keep stopping her from grabbing at my crotch. It's not like I didn't appreciate the thought, but this was all supposed to be very super secret, remember? Kelsey... she did not seem to remember that.
"No, I get it," Kelsey said sulkily.
"I just don't want to hurt anyone's feelings," I said.
"I understand about Julia," Kelsey said, "She's your friend and I don't want to screw that up by screwing around too much. But Sarah? I promise you, you don't have to worry at all about Sarah."
I grinned goofily. Kelsey continued.
"I had fun yesterday. Did you?"
"Yes!" I practically shouted it, then looked around and said more quietly, "Of course."
"Me too," Kelsey said, "We're just having a good time and there's nothing wrong with that. You don't want to be so out in the open. I get that. But we can still have fun, right?"
Then Kelsey reached down and grabbed my dick. Maybe what I needed now was a little less fun.
*
Kelsey and I caught up with the other two girls and we walked together. Three babes and a boy. As we went, it seemed to me like the entire city was staring at us and I could see why.
Sarah's body seemed to scream sex and knowing how she looked with all her assets out only increased the volume for me. I could still picture her face contracting with pleasure as my sperm splashed against her skin. Her impossibly bounteous breasts practically shining in the hot tub, shaking as she reached release. Whenever she was near I could smell her perfume, and it made my cock just ache.
Then there was Kelsey. I mean, the whole city seemed to do a double take at Kelsey -- this statuesque blonde with large, kind eyes and a body you usually only saw in magazines. Slender, but not skinny. Striking. She looked as if she were airbrushed in from some otherworldly photoshoot. The goddess amongst all us mortals. The girl who had gone down on me hardcore the day before. Her little pink lips desperately clinging to my cock.
Compared to the other two women, Julia was... Julia. My roommate and (probably) best friend. But that's what made me stare, honestly. And our accidental encounter that morning only accentuated my issues.
I'd spent a year living with her and somehow it hadn't dampened her mystique a bit. Brown hair up in a ponytail, t-shirt and jeans that did more to hide her body than reveal it. Even her eyes -- a striking green, I knew -- were concealed behind black-framed glasses. Knowing the Supergirl behind the Kara Danvers (look it up), made me feel like I was in on a special secret.
Julia was more athletic than the other two girls. Her body more toned. And of course, the fact that we got on so well only made me wonder about her all the more. I could be myself with Julia. That was an even bigger turn on than all the boobs and butts in the world combined.
So yeah. I could understand why everyone was staring. I'd've been looking, too, if I wasn't the lucky bastard who got to be with them.
*
Nothing of interest happened at the zoo. Not even the animals were humping. Then we went to Gino's East for lunch. The food was good, but the girls were all well behaved. Kelsey had clearly taken my admonishment seriously. Maybe a bit too seriously? I mean, a little under-the-table touching would have been fine, right? I didn't even get a toe tap.
After lunch, we went window shopping. The weather had gone from good to gorgeous and the world just seemed generally happy to be out and about on the wide sidewalks of Michigan Avenue. The women went from store to store, talking and turning heads.
Then we passed a clothing store and Kelsey stopped, staring into the window.
"I want to go in and find a bathing suit," she said, "Sarah said you guys went in the hot tub last night and I want to go, too."
I shot Sarah a look and her cheeks went a little pink. What had the sexy brunette said, exactly?
"I could use a suit, too," Sarah said, "I mean...ummm, another one. I only packed the one and it's still a little, um... wet."
"OK, I guess we should all get bathing suits for the pool tonight," Julia said. I just nodded and followed the girls in. Just happy to be supportive.
The store was beyond busy, probably almost all tourists like us, and it was certainly more than the staff could handle. I felt like a salmon, fighting through the crowds to the back where the bathing suits sat. The place smelled like a clothing store, the scent of fabric and whatever chemicals are used to clean fabric. They were playing something loud and thumping that seemed to just go on forever. You know the one.
We were pretty much alone back by the bathing suits. Each girl took turns holding up an outfit and posing. It gave me plenty of time to picture them in their potential new outfits and it was wonderful, willing torture. Kelsey kept holding up skimpy bikinis, practically setting my groin on fire. Sarah and Julia, meanwhile, looked at far more conservative outfits that still sparked my expansive imagination.
Each woman chose a few suits to try on, then tried to find a salesperson, but the entire section of the store seemed to have been abandoned in the chaos. Finally, the girls gave up and decamped to the changing rooms as a group, potential purchases in hand. I was told to sit on a small, only somewhat uncomfortable chair near the door and await the fashion show. The building could have started to collapse and I'd have stayed glued to that spot.
While I waited, I looked around the store. The place was pretty big and we really were alone back there. Like sharks to blood, the front of the store was a feeding frenzy of shoppers, leaving our own waters quite calm. I probably could have tried on a bathing suit right in the middle of the store and no one would have noticed.
Julia came out first, wearing a navy blue one piece that was about an inch of extra material away from being a wetsuit. She made it work though, vamping and twirling like a fashion model out to stun the crowd. I'd never seen my tom-boy roommate act so girlie. Then she burst out laughing, breaking the illusion. I could hear her giggles echo as she scampered back to the changing rooms.
I barely had the chance to recover when Kelsey came out in a yellow bikini that was way more revealing. She posed just as Julia had done, but was clearly taking her moves far more seriously.
Kelsey had grown into the classic model body, but that came with the expected drawbacks, as well. Some tits, less ass. Yet her suit still somehow managed to leave a good bit of her best bits showing. Quite the accomplishment.
