The Second Day of Spring Break

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Day two of our spring break adventure. A new development.
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The Morning After

It was mid-morning Saturday, and I was woken up by the sound of frustrated groaning. Dillon's head was on my chest, and one of his legs was across my legs. I could feel his hand tugging at his cage and his hips grinding against my leg. Once I realized what was happening, I started laughing.

"What's wrong, baby?" I asked.

"Fuck you," he said frustratedly. "I've got morning wood, and it's got nowhere to go."

"Hot," I said, "Let me see."

He rolled onto his back and pulled the blankets back, and lifted his skirt. Sure enough, his dick had filled the cage completely, and it was standing straight up, straining against the cage. A little bit of precum was coming out of the tip of the cage.

"Looks painful," I said teasingly.

"IT IS," he said, quickly losing patience with my bullshit. "And I'm NOT your baby."

"Oh, I'm so sorry," I said, exaggerating the last two words as I kissed my way down his chest and stomach.

I looked up at him, and I could see the frustration leaving his face as I continued kissing my way down his body. When I got down to his cock, I licked through the opening at the tip.

"Mmm," I said teasingly, "I wish I could have more," I said.

"Bitch! You're the one with the keys. Unlock me right fucking now, and you can have all you want!" he said incredulously.

"You're right!" I said in faux absent-mindedness.

"You're not going to unlock me early, are you?" he asked dejectedly.

"Not a chance," I said with a chuckle.

He dropped his head back down on the pillow, and I put his locked dick in my mouth and started licking his balls.

His head jerked back up. "Whoa!" he said in surprise.

I pulled my mouth off. "What's wrong? Do you want me to stop?" I asked.

"No! Keep going!" He pleaded.

"Okay," I said, "just keep it down."

I put my mouth back on his locked dick and ran my tongue all around his balls and groin while slurping on his locked shaft. I moved down to his balls and tugged on the tube to give him at least SOME sort of sensation. I started to suck on his balls while I used the tube to stroke him. I could feel his body start to tense up like he was approaching climax, so I stopped completely and said, "Are you hungry? Let's see if Ben is up."

The look on his face was priceless. It was a mixture of disappointment and frustration.

"Just wait until I get unlocked," he said warningly.

"Ooh, I can't wait," I said in mock fear. "I'm sure the 90 seconds of pounding you're going to give me will really teach me a lesson. Splat." He threw a pillow at me as I closed the bathroom door behind me.

After I finished in the bathroom, Dillon went in, and I waited for him before going out into the living room. He came out and was a little surprised to see me standing by the door.

"What's up?" he asked.

I smoothed his shirt and adjusted his skirt to buy time.

"About last night," I said.

"Forget it," he said. "We can talk about it later."

"It's just, maybe you're not wrong," I said.

"I know," he said. "And maybe I don't want you to be, but I promise we can talk about it before the week is over. We'll have a definite answer before I go home, okay?" He leaned down to kiss me and then quickly pulled away before his lips could reach mine.

"Hah!" he said as he walked out into the living room.

"Rude," I said in protest.

Ben was on the couch, watching TV. He had changed out of his baseball uniform at some point, and he was now in just a pair of micro trunks, a compression shirt, and mismatched ankle socks. His hair was still wet from the shower.

"Hey," Dillon said by way of a greeting.

"Hey," Ben replied. "So... Are you guys like... A couple now..?"

I could feel my face turning red.

Dillon looked at me knowingly.

"Definitely not," Dillon said. "But if you act right, I might be your new daddy by the end of the week," he said with a smirk as he stood in front of Ben and bent over to touch his toes, putting his ass in Ben's face.

Ben slapped Dillon's ass a little harder than I think he intended to.

"Ooh, someone's a little cranky this morning," Dillon said, standing up suddenly.

"It's this fucking cage," Ben said. "I woke up with the worst morning wood, and it had nowhere to go. I've been awake since like 6:00 listening to you two talk about talking by the end of the week."

My face turned red again.

"Told you this place isn't soundproof," Dillon said to me.

"Right," I said pointedly. "I'm going to make some coffee and possibly put some whiskey in it," as I made my way into the kitchen.

"Ooh, yummy," Dillon said as he followed me.

I got the coffee going, and Dillon jumped up to sit on the counter. I was facing away from him, and he pulled me in between his legs and put his arms around and legs around me. He put his chin on my shoulder, and I absentmindedly put my hand on his leg and started rubbing his stockinged thigh.

"My uniform looks good on you," Dillon said.

"It looks better on you," I said.

"I know," he said.

Ben walked into the kitchen, saw us, and rolled his eyes. "How have you already gotten to the cuddling phase?" He asked in mild disgust.

"It's the outfit," I said. "It's totally turned him into a girl. You'll see when yours gets here today."

"My what?" Ben asked, genuinely confused.

"Your outfit," I said.

"I don't get it," Ben said, still confused.

"I ordered an outfit just for you, and it should be here today, if it's not already here," I said.

I pulled my phone out of my back pocket to check on the order status.

"Not quite, but it's close. We have some time. Come here," I said.

I tapped on Dillon's leg so he would uncross his ankles, and Ben reluctantly shuffled over to us. I put my arms around him as he put his head on my chest. Dillon put his arms around the both of us, and I let my hand wander down to Ben's ass and gave it a squeeze. Ben chuckled and said, "You're such a perv."

I drank my coffee on the couch and scrolled through my phone while the guys flipped through channels on the TV. There was a knock on the door, and Ben got up to answer it. He brought the box inside and set it on the coffee table.

"Go for it," I said.

Ben opened the box and started to go through everything in there. The outfit I put together was similar, but not identical, to what Dillon was wearing. I could tell Ben was starting to get jealous of the attention Dillon had been getting, and I didn't think getting him the exact same things would be the best solution.

He unpackaged everything, and he was looking at it, a little intimidated.

"You can get dressed any time you want," I said. "If you want to wait and do a 24-hour thing like Dillon or just do it now to see how it looks and then change back and put it on again later. Whatever you want."

"You just want to fuck both of us dressed like this at the same time," Ben said knowingly.

"Well, yeah. That, too," I said with a smirk.

"Fine," Ben said. "You're lucky I kind of like you."

Ben stood up and got completely naked. Throwing each piece of clothes at my face as he took it off.

"I've only been wearing that for like an hour and a half, so no need to perv out on it," Ben said teasingly.

I held his underwear on my face and inhaled deeply while grabbing my crotch anyway, and both guys laughed.

Ben made a big show of getting dressed, which I enjoyed. I was starting to get concerned that he was feeling left out, or he was getting upset that an intimate relationship may be developing between Dillon and me, and he'd be squeezed out.

Ben started with the stockings, which to my surprise, were fishnets.

"Classy," Ben said sarcastically.

"Nothing but the best for my favorite slut," I said.

He put his foot on my knee and worked the stockings up his leg, repeating the process with the other leg. He put on the garter belt and clipped the tops of the thigh-high fishnets in place. He turned around and asked, "Are the seams straight?"

"Yup," I said.

He pulled on the panties, shimmying them on the same way Ben had to over his muscular thighs, but they fit perfectly just over his hips. He pulled the thong up into his ass and turned around, and asked, "How's it look?"

"Perfect," I said.

He got the shirt out and pulled the tags off. This one was a button-up shirt instead of a pullover, so of course, he didn't have any trouble putting it on, but it was tapered, and the material was stretchy, so it hugged his torso beautifully.

"How come he got an easy shirt to put on?" Dillon asked jealously.

"Because I like him more," I said matter-of-factly.

Ben buttoned the shirt, leaving just the top two unbuttoned.

"Here comes the scary part," Ben said as he sat on the couch.

He pulled the shoes out of the shoebox and held them up. They were similar in style, but not identical, to the ones Dillon was wearing. Same heel height, of course.

He set the shoes down in front of the couch and slipped his right foot into the right shoe. The shape of the shoe forming his foot into a pointed, tip-toe position accentuating his arch drove me wild with desire. He adjusted the shoe a bit as he pushed his foot in and bucked the ankle strap. He repeated the process with the left shoe.

He stood up awkwardly and took little steps to turn around and said, "I don't know how girls walk around in these all day."

"Practice," I said. "I know you know there's one more thing in the box."

Ben sighed and said, "Fine."

He pulled the last package out of the box and unwrapped it. It was a metal butt plug with a green jewel on the end to match the skirt he was wearing. He stuck it in his mouth, walked over to me on the couch, he put his foot up on the armrest of the couch, locked eyes with me, pulled the butt plug out of his mouth, and started to work it into his butt, never looking away from me. He winced a little, but once it was in, he took his leg down, turned around, spread his cheeks, and asked, "Is it straight?"

I reached up to adjust it and said, "So aggressive. Yes," and I put his thong back and flattened his skirt.

He stood next to Dillon, and they were back to being roughly the same height again.

"You know what to do," I said.

"So demanding," Dillon said as he put his arms around Ben's neck, and they began to kiss.

A few minutes later, an odd chiming noise started to come from my phone.

"What the hell is that?" I asked.

"Keys! Where are the keys?" Dillon asked excitedly.

I dug my phone out from between the couch cushions, and I saw "24-hour timer" on the screen.

"Damn, already?" I asked.

"Where are the fucking keys?" Dillon asked impatiently.

"I thought they were on the coffee table," I said.

Dillon started picking up all the empty packages and looking for the keys.

"Maybe they fell?" I asked.

Dillon got down on his hands and knees and started looking under the coffee table and under the couch.

"Did someone move them to an end table? Or are they in the kitchen?" I asked.

I looked at Ben and held a finger to my lips -- the universal shush -- as I held up the keys in my hand.

Ben stifled a laugh, and Dillon looked up at him and then at me. I started cracking up. I have the worst poker face.

"You're such an asshole!" Dillon said as he grabbed at my hand.

"Easy, now," I said calmly. "A deal's a deal. Come here and keep your hands behind your head until I say."

Dillon stood in front of me, doing exactly as I said, and I moved his panties to one side, unlocked his cage, removed the tube slowly, and then the ring. I massaged his dick and balls gently, especially around where the ring was, and he became erect almost instantly. Dillon tilted his head back, keeping his hands behind his head the whole time.

I put my mouth on the tip of his cock and gently sucked on it, going deeper and deeper with each stroke until I was deepthroating him, gently fondling his balls.

"What's it gonna be?" I asked. "Are you going to punish me for teasing you?" I looked at him pleadingly. "Or are you going to fuck Ben like the bitch he is?"

"Hey!" Ben said indignantly.

"Both," Dillon said as he put both of his hands behind my head suddenly and started skull fucking me right there in the middle of the living room.

"Oooh, hot," Ben said as he stood behind Dillon, holding the base of his cock and fondling his balls.

Dillon pulled his dick out of my mouth and said, "Stand up and turn around."

I stood up and turned around, but he was way too tall in the shoes he was wearing.

"Fuck!" he said. "Take off those pants."

I took off the pants and tossed them to one side.

"Get on the armrest. Doggy style," Dillon said.

I got up on the armrest, and he put his leg up on the couch next to me. I felt him spread my cheeks and spit on my ass, and then I felt the tip of his penis press right up against my asshole. I gripped the edge of the couch, bracing myself for what was about to come, because I knew it wasn't going to be gentle, and I was right. As he struggled to get his dick in my tight ass, I tried to relax, and then he reached up, grabbed my hair, and pulled back on my head -- hard. At the same time he pulled on my hair, he thrust his dick into my ass as deep as he could go. He gave me every inch of his dick. I collapsed forward onto the armrest, but I didn't really have anywhere to go since he was still holding onto my hair, and the armrest was holding my hips up. He laughed smugly and said, "I told you I'd make you pay." He jackhammered my ass with all the vigor a horny 18-year-old guy has, but then he stopped suddenly and said, "Flip over."

I did as I was told.

He pulled out, and I flipped onto my back. He grabbed a cushion and put it under me to raise my hips up a bit and put his dick right back inside me. He put my feet on his shoulders and grabbed my dick, and started jerking me off with one hand while unlacing one of his cleats I was wearing with his other hand. Ben took this as an opportunity to start sucking my dick and join in. He got on his knees on the side of the couch to put his mouth to work.

Dillon finally got the cleat unlaced and took it off my foot. He held the cleat up to his face and inhaled long and hard while thrusting deep inside my ass just as long and hard. He dropped the cleat and grabbed my hips, and started to jackhammer my ass again. Ben took his mouth off my dick because there was just way too much going on, so he switched to using his hand to jerk me off.

I put my foot on Dillon's face, rubbing the sweaty sock that he had worn the day before and I had worn for the last 24 hours inside his cleat, all over his face. That seemed to have done the trick because it was right at that moment that Dillon started to tense up, and I could feel my ass getting filled with intense heat, which is what set me over the edge because I erupted all over Ben's hand and Dillon's shirt that I had been wearing for the last 24 hours.

Dillon's thrusting started to slow down, and Ben kept stroking me, milking every last drop out of me. Dillon was panting, catching his breath, and Ben collected as much jizz off my cock as he could with his hand and wiped it Dillon's open mouth while laughing hysterically. Dillon swallowed it, licked his lips, and said, "More."

"If I get unlocked, I've got a huge load you can swallow," Ben said hopefully.

"Nice try," I said. "Plus, we all know you can be milked while locked. Something to look forward to in about an hour."

"An hour?" Ben asked disappointedly.

"Yeah," I said, "Your friend over here revenge fucked me pretty good."

"I told you I'd make you pay," Dillon said with a thrust of his hips. He was still inside me.

I laid back on the couch, and Dillon started to pull out.

"Wait!" I said. "Give me a minute."

"Okay," Dillon said as he slowly started going in and out of me again.

"I mean, that's not exactly what I meant, but I'm not opposed to that either," I said with a smirk.

Ben started walking around the living room, practicing in his heels and looking at his reflection in the TV.

"You're right; these shoes make my legs and ass look great," he said.

"Okay, you can pull out," I said to Dillon. "Slowly."

Dillon pulled out and stood up, and I laid on the couch for a minute. While I was recovering, Dillon got down on his knees next to me and start to lick the semen off my dick and belly. He spread my ass and said, "Oof, that looks painful."

"It's been a while since you've fucked me. Maybe we can use lube next time," I said.

"Well, you better get used to it," Dillon said.

"Oh, yeah?" Ben asked. "Why's that?"

"I mean, for spring break," Dillon said hurriedly, turning a little red.

"Right," Ben said incredulously.

"Okay, I'm gonna take a shower. Can you guys wait for me to come back out before you start fucking?" I asked.

"Sure," Dillon said. "I need some time to recharge. Maybe I'll join you?" He asked.

"Sure," I said, "But you're not fucking me again today."

"We'll see," Dillon said with a smirk.

I went into my bathroom, got undressed, piled all of Dillon's baseball gear into my dirty clothes hamper, and got in the shower. Dillon followed behind me a few minutes later. I took a quick shower just to get the sweat and jizz off of me and went into my bedroom to get dressed.

I went back to the corner where I left the stuff Dillon dressed me in before I put on his baseball uniform the day before. The compression shirt, neoprene shorts, mismatched ankle socks, Dr. Marten boots, and leather harness.

Dillon seemed to be taking his time in the shower, so I went back out into the living room.

"That was fast," Ben said.

"Yeah, I didn't want you to get jealous and think we were fucking without you," I teased.

"Shut up," Ben said.

There was an awkward silence, which was unusual because we've only ever had comfortable silence between us. Something was changing.

"What's up?" I asked.

"Nothing," Ben said.

"Look, this doesn't have to be a week-long fuck fest," I said. "We can just hang out or go somewhere."

"It's not that," Ben said. "Fucking is fun, and it's getting spread around pretty fairly. I'll admit I was jealous that you were going to give Dillon more attention because he's new, and he's only staying for a week, but I know you're not like that."

"Is it the possibility of a relationship that has you worried? You think you're going to get pushed out or turned into a third wheel?" I asked.

"Yeah," Ben said after a long pause.

"Well, try not to think about it. I mean, it was fun to think about for a bit last night, but I don't think that's what he wants. He said we'd talk about it before the end of the week so I'm not gonna bug him about it. I don't need another fucking like I just got on the couch. I'm not gonna sit right for the rest of the weekend. If he just wants to fuck, that's fine. He's got two dicks to pick from. Chin up, little cousin. I've got some balls to rest on it," I said with a smirk.

"You're such a perv," Ben said with a laugh. "Thanks. I really wasn't sure what was going on with all the whispering and private conversations."

More silence, but this time it was the familiar comfortable silence.

"You look pretty good dressed like a girl," I said.

"Shut up," Ben said. "And thanks."

"Come on," I said as I stood up.

"What?" Ben asked.

"Stand up," I said as I held out my hand to help him up off the couch.

Ben grabbed my hand, and I helped him up. He towered over me in his six-inch heels. I continued to hold his hand, and I led him into his bedroom and closed the door behind us.

"What's going on?" Ben asked.

I grabbed him by his waist and pushed him onto his bed. I climbed on top of him and started to kiss and bite his neck. Ben started to laugh, and he wrapped his legs around me. I held him down by his throat and kissed him deeply, then I pulled his panties off, stuffed them in his mouth, grabbed the bottle of lube off his nightstand, lubed myself up, pulled out his buttplug, wiped the excess off up his ass and plunged my throbbing dick into his hungry little asshole.