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?"
