Summer Brea

It was approaching the end of the semester, and Dillon worked his way off academic probation so he could get back on the team. But it wasn't all great news. His program advisor recommended but didn't require, that Dillon enroll in some supplementary courses during the summer break.

Dillon's parents had planned a summer vacation many months in advance, and they were ready to cancel everything, even the non-refundable parts, to stay home so Dillon could take the recommended courses and not fall behind in the new semester.

Ben being the sneaky little genius he is, told me all about the situation before he coyly asked what I thought about Dillon moving in with us for the summer. Of course, I could never say no to either of them, so that's the plan we hatched.

At the end of the semester, a day before Dillon's parents were leaving, we went to pick Dillon up.

I had met with Dillon's parents previously when he stayed with us for spring break, but I was happy to meet with them again. It was a pleasant meeting, of course. They explained to us that they were going on a cruise and wouldn't be reachable while they were at sea, but they'd check in with Dillon as frequently as they could. I reassured them that he'd be under my constant supervision since I had transitioned to a full-time work-from-home position. Dillon mentioned something about time zone differences and school schedules as an excuse for not being able to respond immediately, but he would check in when he could, too. Smart kid - already laying the foundation of an alibi.

It was Sunday afternoon when we went to pick Dillon up from his parents' house. He rolled out of the house with two large suitcases, his backpack, and his baseball duffle bag.

"You know I own a washer and dryer, right?" I asked jokingly, knowing full well that at least half of the things in his bags were shoes, costumes, and sex toys.

"Yeah, I know, but I don't want to be a bother," Dillon said shyly.

"If I thought you were a bother, you wouldn't be staying with us," I said as I lifted a suitcase into the trunk of my car.

His parents handed me an index card with all the names of the different places they'll be along with the dates and contact phone numbers.

"He'll be fine, I promise. And he's going to get straight A's. I've seen his course list, and I'll be tutoring him personally," I said.

"If he forgot anything, although I can't imagine he did," I began as I lifted the second suitcase into the trunk of my car, "Would it be okay for me to bring him back to get it?" I asked his parents.

"Yes, of course," said his mother. "We just don't want him unsupervised with us being on the other side of the world. Just be sure to set the alarm before you leave."

"Perfectly understandable," I said.

Dillon said his goodbyes, and we all got in my car.

We got back to my place and got out of the car. Everyone grabbed a bag and walked up to the front door. Dillon unlocked it with his key and made his way inside.

"My key still works," he said with a tone of surprise.

"Why wouldn't it?" I asked.

"I dunno, I just thought it was all talk," he said. "My parents don't trust me home alone. Why should anyone else?" He asked.

"Dude. You threw a party, and your parents literally had to remodel - I can understand why they're not down with doing that again," I said.

"Ugh, when is everyone going to let that go?" He asked.

"You parents? Probably when they're done paying off the loan they had to take out to fix everything. Me? Never," I said with a laugh.

"They're doing alright. Did you see all the places they're going? Kinda bummed to miss it, but I did it to myself," Dillon said.

We were all still standing in the foyer of my apartment.

"Okay, you know the drill," I said.

The boys kicked off their shoes by the door, and Dillon started to undo his pants.

"No! Not THAT drill," I said with a laugh. "Go put your shit away."

I was genuinely curious to see which room Dillon would pick. I knew he and Ben would fool around when they had a private moment together, but Ben wouldn't necessarily tell me those types of things first thing when he got home. Which is totally understandable. Everything was very casual, and after all, it was just sex.

Dillon went all the way to the end of the hall and went into my room.

"Nice," I thought to myself.

Dillon came back out for the rest of his bags and repeated the process.

"I'm going to unpack a few things," Dillon said from the end of the hallway.

"Go for it," I said. "There's room in the closet and dresser."

Ben crossed his arms and gave me a look that could only mean, "Really? You made room for him?"

"What?" I asked, "Is your room even suitable for habitation?" I asked.

"Of course not," Ben said. "I'm a free spirit."

"You're something," I said as I rolled my eyes.

Ben and I sat on the couch and turned on the TV. We had some idle chat about what to do over the summer and how we can both help Ben stay on track so he actually passes.

"Are we going anywhere else today?" Dillon asked from the end of the hall.

I looked over at Ben, and he shook his head while shrugging his shoulders.

"Probably not," I said. "What's up?"

"Just wondering if you guys were waiting for me to head out or something," Ben said.

"Nope. Take your time," I said.

After a long while, I heard my shower turn on.

"He's settling in fast," I said to Ben.

"Guess so," Ben said as he pulled his shirt collar away from his neck and gave himself a sniff test.

"You're fine," I said. "No need to join him."

"I was going to JOIN him," Ben said defensively. "I have my own shower, but I wanted to make sure I didn't stink."

"I'd tell you if you were stinky," I said as I nudged him playfully. "Don't make his stay with us weird. We can take turns."

"What if he doesn't want to?" Ben asked a little dejectedly.

"That's what this is about? Because he picked my room instead of yours?" I asked.

"Not just that, but kind of," Ben said.

"I'm sure it had nothing to do with who, and more with what," I said. "You know my room is bigger. Plus, I don't have a bunch of 'maybe' clothes all over the place, so it's a little more inviting."

"Yeah, I know you're right," Ben said. "But still, you two are going to be doing what you two do when you're in bed together."

"I mean, I can't say either way, but you're probably right," I said.

"Great," Ben said disappointedly.

"No one is stopping you from joining us. We've all slept in my bed before," I said encouragingly.

"Yeah, that's true," Ben said a little more happily.

"I mean, come on, it's a king-size bed. The two of us can be in bed comfortably and never touch. What's a third with some light touching?" I asked.

"Mmm... Good touch," Ben said as he envisioned it.

"Alright, calm down. Horndog," I said to snap him back to reality. "There's going to be plenty of time for all that over the next few weeks."

"Okay, fine. I know you're right, but it's gonna be a fun next couple weeks," Ben said with a smile.

"Did you hear the shower turn off?" I asked.

We were both quiet for a moment.

"No, but it's off now," Ben said.

"I wonder how long he's been out of the shower," I mused.

"Eh, whatever. He'll come out when he's ready," Ben said with a shrug.

We went back to watching TV and making small talk when suddenly Ben and I heard the telltale click-clack of high heels coming down the hallway.

Dillon walked into the living room wearing the six-inch stripper heels I had gotten for him over spring break. His legs were shaved smooth. He was wearing a pink tartan-patterned pleated skirt that just barely covered his bulge, a white polo shirt that looked like it was one size too small, and a pink spiked collar.

"Hey, boys," he said with a smirk as he reached his hands up above his head, which lifted the bottom of his shirt up above his navel, revealing that he had shaved his armpits and pubic area, too.

"Hey," Ben and I said together.

Dillon turned around and lifted his skirt to show he was wearing boy short panties that had "Daddy's lil fuck toy" printed across the ass.

Dillon walked over to us, stood right in front and between us, turned around, and started to sit down. Ben and I both instinctively moved away from each other a bit, just enough to make room for Dillon to sit between us.

Dillon stretched one leg out, placed it on the coffee table, then crossed his other leg on top of it, leaned back, put his arms around Ben and me, and asked, "So what are we thinking tonight? Pizza? Chinese?"

I ran my hand up Dillon's leg to feel how smooth it was and said, "Dressed like that? You can have whatever you want."

"I know what you like," Dillon said. "I know what you BOTH like," he said as he looked between me and Ben.

"I'm down for anything," Ben said in response to Dillon's question about dinner.

"We know you are, slut," Dillon said with a laugh.

"I meant for dinner," Ben said defensively.

"Yeah, I know. You'll put anything in your mouth," Dillon said, continuing to tease Ben.

"You're such a bitch!" Ben said teasingly.

"Yeah! Why do you think I'm dressed like this?" Dillon asked ironically.

"You're just jumping right in on the first night, trying to get turned into a finger trap," I said.

"You know it," Dillon said. "Let's just get all the tension gone right from the get-go and not worry about who's sleeping where or why and who's gonna bang me first. The only fair way is for both of you to bang me at the same time. And he was right," he said as he looked at me. "I picked his room because it's bigger, and there's really no reason you can't join us at the end of the night."

Ben and I both looked at each other and then at Dillon.

"Your walls are much thinner than you think," Dillon said with a smirk. "But I do love that there was already competition for me before we even got here."

"Well, okay. You two take care of dinner," I said to Ben and Dillon, "And I'm gonna go see what my room looks like."

I got up from the couch and went to my room. It looked exactly the way it did when I left to pick up Dillon with the exception of two suitcases in the corner. I opened one of the drawers I had cleared for Dillon, and his socks, underwear, and a few accessories were all neatly arranged. He brought leather ankle and wrist cuffs. There were a few ball gags, butt plugs, different chastity cages, and nipple clamps. He was definitely ready for a party.

I looked in my closet and saw he had hung most of his shirts, and his jeans were folded neatly in a pile on the shelf. On the floor, in the closet, he had no less than 12 pairs of shoes, all arranged in two rows and stacked on top of each other. On the other side of the closet was his duffel bag that he used for baseball. His uniform was folded on top and his cleats were on top of his uniform. I picked up one of his suitcases, and it felt empty, but it was zipped shut. I didn't want to snoop too much.

I poked my head out of my bedroom and asked, "Do you mind if I put your suitcases in storage so they're out of the way?"

"Yeah, that's fine. They're completely empty. Thanks!" Dillon said.

"Hey, Ben! Come grab these suitcases and put them in storage. While you're down there, bring up the box that's labeled 'Easter Decorations,'" I said.

"Dammit!" Ben exclaimed as he got up and came into my room.

He grabbed the suitcases and said, "I'll be right back," as he left to take them to the storage unit.

As soon as I heard the door close, I called for Dillon to join me in my room.

I went to the dresser, pulled out a chastity cage, tossed it to Dillon as he walked in, and said, "Put it on."

"Aww, man! You found those already?" Dillon asked defeatedly.

"Of course. You think I'm gonna let you try to bury that cock in me on the first night?" I asked.

"What if I use it to make Ben moan?" Dillon asked pleadingly.

"Tempting," I said. "Lock it up, and we'll see how it goes later."

Dillon lifted his skirt right in the middle of my room and put the chastity cage on. He handed me the keys, which were on a necklace, and I put them around my neck.

I heard the front door open and said, "Quick, get on your knees in front of me."

Dillon trotted over in his heels, stood in front of me, got on his knees, and put his hands on my hips.

I could hear Ben coming down the hall, so I put my hand on top of Dillon's head and leaned back a little.

"Oh, what the fuck?" Ben exclaimed as he walked into my bedroom.

I started cracking up and turned around to show Ben that my pants were still on and the zipper was closed. Dillon started laughing, too, and said, "I'm sorry, it was perfect timing, and I couldn't help myself."

Dillon put his hand out as if to ask me to help him up. I grabbed his hand and give him a little pull as he stood up. He was a little unsteady on the way up, and I quickly put my hands on his waist to make sure he didn't fall. We locked eyes for a moment, and then Dillon smirked as he put his hands on my shoulders and said, "My hero."

"Will you two knock it off?" Ben asked pleadingly. "The food's going to be here any minute, and if the delivery guy is someone we know, I'm gonna make Dillon answer the door dressed like that."

"You're not gonna make anyone do anything," I said. "But, if you don't play nice, I'm gonna make you lock up, too."

"Too?" Ben asked, catching onto the operative word.

Dillon turned to face Ben, lifted his skirt, and lowered his panties to reveal his locked dick.

"Yup, 'too,'" Dillon said with a hint of resignation in his voice.

Ben's hands were still on my shoulders, and my hands were still on his waist.

"You being taller than me is weird," I said as I took my hands off his waist.

"You're like an inch taller than me, if that," Dillon said as he took his hands off my shoulders.

"Yeah, when we're both barefoot, but you're wearing six-inch heels so now you're like five inches taller than me, and it's weird. You're usually on your back when you wear those for me," I said jokingly.

"Fair enough," Dillon said. "I think Ben should dress up, too."

"I'm not opposed to that," I said with a smirk.

"I know you're not, perv," Ben said jokingly. "I'll think about it, but you have to promise not to start without me if I'm gonna take forever shave everywhere," he said.

"Well, I don't think Dillon has much of a choice but to wait," I said with a smirk.

"Yeah, but he's a cock-hungry slut, and you'll stick your dick in anything that stands still long enough," Ben said knowingly.

"True," I said. "But, I suppose we can wait for you if you're going to put in all that effort."

"Alright, fine," Ben conceded. "The food isn't supposed to come for another 40 minutes. I think I can be done before then," and he went to the bathroom and started the shower.

Dillon and I sat on the couch and he put his legs across my lap as we watched TV.

"Is this okay?" he asked playfully.

"I dunno, wouldn't wanna get started without him," I said mockingly.

"Remember that time you went to a glory hole?" Dillon asked, almost seductively.

"Which time?" I asked.

"Um. You went more than once?" he asked as he sat up.

I started to laugh and said, "I didn't think you were the jealous type. It was just once and it was your pretty little mouth on the other side of that hole."

"You were so close to not getting a blowjob tonight," Dillon said as he sat back and put his legs back on my lap.

"Oh, no" I said in mock disappointment.

"Shut up," Dillon said as he threw a pillow at me.

I caught the pillow and put it behind my head as I leaned back.

"You can start now, if you want," I said smoothly.

"We promised we would wait," Dillon said disappointedly.

"Well, does a hand job count?" I asked mischievously.

"I think so," said Dillon.

"What if you just rub your feet on my crotch in those high heels?" I asked.

"Totally. I'm just trying to get comfortable, right?" Dillon said with a glint in his eye.

We continued to watch TV, and Dillon was rubbing my dick through my jeans with his high-heel-clad feet.

I was rock hard when the doorbell rang. The food was finally here. I answered the door, brought the food in, and set it down on the coffee table.

I heard the click-clack of high heels coming down the hallway, and Dillon said, "Perfect timing!"

Ben was dressed almost identically to Dillon, except his skirt was blue, and he wore a black spiked collar.

Ben was holding something in his hand, and he said, "I think Dillon should wear this to get warmed up since we're going to be tag-teaming him later," as he held up a medium-sized butt plug.

"Oh, good idea!" I exclaimed.

"What? Wait. Are you sure about that?" Dillon asked nervously.

I sat on the couch and said, "Come here."

Dillon stood in front of me. I grabbed him by the waist, and pulled him down toward me and bent him over my lap. I lifted his skirt and pulled his panties to the side.

"You'll thank me later," I said.

Ben put the butt plug in his mouth, and I spit on Dillon's asshole.

"Take a breath," I said.

Dillon took a deep breath and said, "You're lucky I like you guys," and exhaled slowly.

Ben slowly worked the butt plug into Dillon's tight little pink asshole, working it slowly in and out until Ben was able to get it deep enough that Dillon's asshole swallowed the plug, and it settled neatly in place. It was a pink heart-shaped crystal.

"Aww, it matches his skirt," I said.

"It actually feels really good," Dillon said.

"Told you he's a cock-hungry slut," Ben said as he put Dillon's panties back in place.

Dillon stood up and wiggled his hips a little. "Perfect," he said.

We all sat down, ate, and watched TV. Ben and Dillon dressed like schoolgirls and acted like it was part of their daily routine, perfectly normal.

"I forgot how easy these are to walk in," Ben said as he held up his leg, admiring the shoe and smoothness of his leg.

"Right?" Dillon said in agreement.

After a while of watching TV and small talk, I said, "Okay, I think it's time."

"Finally!" Ben said.

"You could've said something earlier," I said.

"You're not the ones with a hunk of metal up your ass," Dillon said.

"I wonder if we can fit both of our dicks in there," Ben contemplated.

"Absolutely not," Dillon said. "Well, maybe. We'll see how it goes."

"He's such a slut!" Ben said laughingly.

"Only for you two!" Dillon said defensively.

"Okay, okay. You're both sluts. Now, calm down before you get a spanking," I said.

"Now I'm definitely not going to calm down," Dillon said.

"Oh, yeah?" I asked. "Stand up."

Dillon stood up immediately, and I reached under his skirt to pull down his panties. I let them drop around his ankles and told him to bend over.

He bent over and lifted his skirt just above his butt and I gave it a sharp smack.

"Ooooh, that was perfect," he said.

Ben matched my force, and Dillon said, "Oh, my God. Yes!"

I started to get hard watching Dillong get so turned on from getting spanked.

I stood up and said, "Kick those panties to the side. I don't want you to trip when I start tossing you around."

Dillon kicked the panties to the side and said, "Yes, daddy."

I grabbed him by the neck and kissed him passionately while groping his locked dick. Then I immediately turned to Ben and did the same thing, except he wasn't locked. I grabbed his hard dick and started to stroke it.

I broke apart from Ben and said to Dillon, "Blow him." Dillon got down on his knees and immediately started sucking Ben's dick. I stood there, watching and stroking inside my boxer briefs. I stood right next to Ben and pulled my dick out. Dillon immediately started sucking my dick while stroking Ben's. Dillon went back and forth between me and Ben for a few minutes before I said, "Now both."