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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 pendik escort 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 maltepe escort 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.
Kelsey paused as she came over and looked down at my crotch. Satisfied that she’d gotten the correct reception, the bombshell blonde turned and stalked off. I was more than happy to watch her little butt go by.
I thought for sure by now someone would come over and put a stop to this, but when I looked, no one was paying attention. Certainly, there were cameras hidden somewhere and I imagined someone in security was having a heck of a day. Enough to not say anything about our display.
I heard a bit of back and forth coming from the changing rooms.
“…yes, you do.”
Sarah sort of stumbled out from the back. She was wearing a deep, almost black green one piece. The suit was conservative, but that didn’t make Sarah’s body shine out any less. Her breasts seemed ready to rip right out and her butt was escaping out the back, as well. A few, timid shoots of Sarah’s pubic hair poked out of the gusset.
She nodded at me, shyly.
“I’m not doing anything wrong,” she said, defiantly, “Just getting a friend’s opinion on a bathing suit. And, as a guy, I’d want you to tell me if I look good. For my boyfriend.”
I still hadn’t said a word.
“So this is fine,” Sarah continued, “Trying on outfits is good for my relationship. For him.”
Her eyes drilled down, daring me to disagree. I just nodded my head.
“Fine,” she said, and then without a word turned to walk away.
“You look really good,” I said. Sarah turned. Her whole body seemed to blush. Then she skipped back to the changing rooms.
Then one by one, all three girls came out again to model different suits. Julia brought out another one-piece, something that (*gasp*) opened in the back and showed off some very shapely leg. She tried to do her little act again but couldn’t stop laughing and practically limped out of sight.
Kelsey wore something a bit less skimpy than the first go — a blue thing that she clearly had picked out with someone else’s more modest interests in mind. I made a big show of telling her to “go in there and get less clothes on, young lady.” To which she happily agreed.
Sarah came out in basically the same suit as before, just red instead of green, and it wasn’t her color. It made her beautiful brown skin look orange-y. Too bad. I usually love a woman in red.
“You look incredible, as always,” I told her, “But I think Rob would prefer the green one.” She nodded her appreciation before heading back.
“Last ones!” I heard Kelsey call from inside the changing rooms.
I tried my best not to be too disappointed. The show had to stop some time, I suppose, but I would have been happy to see swimsuits till the store kicked us out. It’s these kinds of sacrifices that make me such a good friend.
Julia, again, was first to go. I didn’t recognize her at first. She was wearing a bright green one-piece, low cut in all the right places and crisscross strapped at the back. I gaped at her bare legs and arms — toned and tan. The suit showed a bit of her well-formed bottom and the big surprise: a pair of honest-to-goodness breasts standing out from her chest. I knew my roomie wasn’t totally tit-less, of course. But it was still surprising to see my besties’ breasties poking out rather than hidden under a loose-fitting kartal escort t-shirt. She wasn’t in Sarah territory, I grant. Or even Kelsey country. But still. Wow.
No little pretend show, this time. No giggling, either. She just smiled and crossed her arms right under her tiny tits. Stared at the ground. She was still wearing her thick black glasses and somehow it made her all the more amazing.
“It’s terrible, right? So totally not good. I’m sorry. I’m gonna go back and…”
“You look fucking amazing.”
“You… you don’t think it’s a little…?”
She gestured at herself as she said it. I just shook my head, too shocked for words.
“Oh whatever,” she said, playing it off and punching me for good measure, “Thanks dude.”
She walked back inside, but I could see the spring in her step as she went back. She came out a moment later and went to the front to go pay. I noticed she was clutching that little green suit to her chest as she went by.
I waited for a bit longer, but still no one showed. Then Sarah came out, fully dressed, holding the dark green bathing suit from before. I cocked my head at her. I was about to ask what had become of her final showing but Sarah spoke before I could start.
“Kelsey’s having trouble with her last suit,” she told me.
“Oh. OK,” I said, “No worries.”
Sarah rolled her eyes at me.
“She wants you to go in and help her.”
“Wait. Shouldn’t one of you girls be able to…”
Sarah’s death stare grew deathier.
I slowly stood. Then stopped.
“Is this alright? I mean…”
Sarah smiled at me.
“I don’t see anyone looking,” she said.
“You mean you’re…” I tried to say it without saying it. To look her in the eyes and somehow ask every question I’d been too terrified to ask all trip without saying a word.
Sarah just grabbed my shoulders, turned me toward the changing rooms, and gave me a shove in the right direction.
I guess that was my answer, then.
The changing area was one long row of rooms running down one side. Each opening was covered by a thick curtain that hung about half a foot off the ground. Kelsey’s most recent bathing suit was hanging carelessly over the furthest back curtain rod.
I knocked at the wall by her door to let her know I was there. A long arm reached out, grabbed my shirt, and pulled me inside. Kelsey was wearing a cute little bikini, sky blue with white stripes. There were string ties at the sides of the bra and bottoms. She didn’t seem to need any help getting it on, I thought, stupidly.
In one swift motion Kelsey dropped to her knees, pulling my shorts down with her. This was now the second time she’d done that and, wow, was she good at it. My cock was in her mouth before I could even breathe.
“Mmmmmhm,” she agreed, nodding her head a bit as she ran her tongue around my shaft. It seemed like she’d managed to maybe get another good inch in compared to the last time she’d orally assaulted me.
“Cameras…” I managed to groan out.
Kelsey pulled her head back with a loud smack. My cock bobbed a bit in the open air, covered in her saliva and already feeling cold.
“Don’t care,” Kelsey said, then grabbed my dick with her hand. She gave him a couple of pumps, all the while smiling like she’d won the science fair.
“If I end up on YouTube, so be it,” she said, then dove back down onto my dick, nearly knocking me through the curtains. Noticing my distress, Kelsey spun us around and pushed me back so I was sitting on the wooden bench — all the while keeping my cock firmly contained between her lips.
“Mmmmmm,” the sexy teenager groaned, using her newfound leverage to start stroking me back and forth with her lips and tongue. She reached with her right hand and found my balls, lightly caressing my sack with a tenderness that was completely counter to the vehemence of her vacuuming.
I leaned my head back, just enjoying at first. Then I saw my opportunity. Sitting this way gave me the added benefit I’d been looking for before: access. I reached over and found Kelsey’s breasts, caressing them in my hand over the cottony bra cup. She seemed to sigh as I grasped, and shifted herself slightly to ensure my hand got at her precocious, perky boobs.
Taking that as a sign to continue, I slipped my hand down inside the bra cups and rubbed at her bare breasts. Their little nip stuck out, jauntily, tickling at my palms. I wanted to reach down and suckle, but I wasn’t going to pause my enthusiastic partner’s pleasuring.
In fact, rubbing and squeezing at her tits seemed to encourage Kelsey all the more. She started sucking with abandon, one hand still on my balls, the other running up my shaft in concert with her lips.
She was a fast learner, my little teenage cock queen. Much less teeth this time and better able to control her breathing, Kelsey quickly reached an ever increasing rhythm. Her innocent face was screwed up tight in concentration over my dick, displaying her trademark cocksucker’s double chin.
The bra was getting in the way of my enjoyment, so one-handed, I pulled the bikini top right over Kelsey’s head. I sighed, contentedly as I held the matching pair in my palms.
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