Business Trip Surprise

To set the scene a little, I'm required to travel for work several times per year. Most of the time, it's a conference of some sort where I sit in a hotel ballroom for six or so hours to try and learn something new about my industry and network with my peers. The conference organizers almost always inevitably chose Las Vegas as the conference location. After many years of attending these things, I have cultivated a healthy dislike of Sin City. I couldn't be bothered to hit the town after dinner every night, and I always went back to my room to watch TV, catch up on e-mail, and go to bed at a reasonable hour. This brings us to the start of our story.

The decision to send me to this conference was made at the last minute (I only got about five days' notice), which wasn't uncommon. I always had things ready to go so I could pack and be out the door within an hour if needed. I completely forgot to mention it to my cousin until the day before when he saw me packing and asked where I was going.

"Vegas, remember?" I asked.

"No? You never mentioned going anywhere," he responded.

"Oh. I could've sworn I did. Sorry about that. It was last minute, and they just told me a few days ago," I said.

Sometimes I would know months in advance, and I usually told him as soon as I knew.

"What am I supposed to do?" He asked.

"About what?" I responded.

"Everything!" he exclaimed.

"Like..?" I asked.

"I don't know. Groceries?" He said.

"Well, I don't leave until tomorrow, so we can make sure you have everything you need today," I said. "We can go now if you want, or I can leave you some money, and you can go get whatever you want when you have time."

"Money is fine," he said.

I finished packing, we had dinner, hung out on the couch watching TV, and started getting ready for bed. A typical evening.

While he was in the shower, I set out a chastity cage, jockstrap, and a pair of his baseball socks. He always got dressed in his bedroom.

I was in my room, making sure I had everything I'd need packed and ready to go the next day when I heard his voice from his room.

"Oh, really?" He asked.

"Yup. I need a reminder of what I'm going to be missing all week," I said.

"Hah, fine," he said.

He came into my room wearing the jockstrap and baseball socks, and I could see the bulge of the chastity cage under the jockstrap. He got under the covers and said, "You better fuck me good tonight. It's gonna have to last me until you get back."

"I think I can manage that," I said.

I pulled his arms to the edge of the bed so he was on his back with his head hanging off the side of the bed. I stuck my dick in his mouth, and he immediately started sucking. I played with his balls and started to finger his hole. He moaned around my dick and then I flipped him over onto his stomach. I got on top of him and slowly pushed the tip of my dick into his tight asshole. As soon as I felt the pop pushing into him, I went balls deep in a single stroke.

"Oh, fuck," he moaned as I started pumping inside him.

"Right there. Keep going," he said.

I kept fucking him just like he told me to, and he said, "Fuck. I think I'm gonna cum."

I flipped him over, felt up his chest, and pinched his nipples as I continued to drill him. He put his feet on my shoulders, allowing me to go even deeper.

"Fuck! I'm coming!" he said breathlessly as he erupted through his cage, all over his stomach and chest. Watching him blow his load all over his tight abs and smooth chest made me lose it, and I came deep inside his ass just seconds after watching him cum.

I sat with my dick in his ass for a few minutes while we both caught our breath. "So... are you going to pull out anytime soon?" he asked. I slowly pumped in and out of his ass and asked, "Do I have to?"

"No, he said, but if you want to go again, you should make it quick. It's getting late," he said.

"Fine," I said in mock disappointment as I slowly pulled out of his ass. "Go clean up so we can go to bed."

He wiped his semen off his belly and put his fingers in his mouth while locking eyes with me.

"Hot," I said.

He got up and went to the bathroom. I quickly got up and went to his room to find the keys to his cage and put them in my backpack. I got back in bed before he came out of the bathroom.

"Holy shit, bro. You blew your load DEEP inside of me. I couldn't even push it out," he said as he got into bed with me.

"Don't get pregnant," I said jokingly.

"It's kind of hot, knowing that your load is still inside me and probably will be most of tomorrow," he said as he started to fall asleep.

"Don't worry," I said, "you know I'm gonna fuck you again in the morning since you're wearing all my favorite things to sleep in."

"Yeah, only because you're leaving. You know I hate waking up locked with morning wood," he said.

"I know. I think it's super gay that you're doing that for me," I teased.

"Shut up," he said with a smirk. "You just came inside a dude. Your cousin."

"That makes me a degenerate," I said as I kissed him, pushing my tongue between his lips and grabbing his crotch.

We went to sleep after a little bit of groping and fingering.

The next morning, I woke up to my alarm and already had a huge erection. I set my alarm a little early so I'd have time to fuck him before I had to leave for the airport. He was sleeping on his stomach, with one knee up, the jockstrap framing his ass perfectly. I grabbed the bottle of lube from the bedside table and lubed up. I slowly climbed on top of him and started to push into his ass. He woke up right as I felt the pop, and I started pumping slowly.

"Oh, fuck," he said in surprise.

"Good morning," I said with a smirk, and then I kissed him. We made out while I fucked him, and then I grabbed his arms and pinned them behind his back. I fucked him harder until I came deep inside his ass again. I squeezed out as much as I could from my dick, and then I reached over to the bedside table to get a jeweled butt plug. I put the butt plug in his mouth to lube it up with his spit and warm it up a little as I slowly pumped his ass with my dick again.

I pulled out of his ass and took the butt plug out of his mouth, and put it in his ass.

"I gotta start getting ready, or I'm going to be late," I said as I got out of bed. He rolled onto his back, and I climbed back on top of him, sitting on his chest and putting my dick in his mouth. He sucked on it for a little bit, and then he said, "Go take a shower. Don't be late."

"Feel free to join me," I said.

"It's so early," he complained.

"You don't have to," I said. "I just thought I'd offer."

"You don't need to offer. I know I can join you whenever I want," he said.

"That's right!" I responded as I climbed off of him and headed to the bathroom.

I got in the shower, and a few minutes later, I heard the door open.

"I smell like sex," he said.

"I wonder why?" I asked sarcastically.

"Shut up and move over," he said with a laugh.

We showered together and got out together. As we were drying off, he asked, "Do you need me to do anything before you go or while you're gone?"

"Well, since you're asking," I said, "Would you mind taking me to the airport?"

"Sure!" he said happily.

"Awesome," I said, "I want to head out as soon as I finish getting dressed."

"No problem," he said.

I went into my bedroom and saw the socks and jockstrap he slept in on the floor. I picked them up, sniffed them, and he laughed.

"You're such a freak," he said.

"Yeah? Then this is really gonna blow your mind," I said as I put the jockstrap on, followed by the socks and then my jeans, which were probably his jeans, and one of his shirts. Then I walked over to the shoes he was wearing yesterday that he left by my closet and put those on.

"That's so fucking hot," he said.

"I'm gonna wear this until I go to bed tonight," I said. "Go get dressed so we can get outta here."

Instead of going to his room, he went into my closet and came out wearing a pair of my boxer briefs and a t-shirt. Then he picked up the jeans I was wearing yesterday and put those on, followed by putting on a pair of my shoes without socks.

"I'm still wearing the butt plug, too," He said. "I'm gonna keep your seed inside of me until I can't hold it in any longer."

I grabbed his ass and pulled him toward me as I tongue fucked his face.

"Let's go before I'm late," I said as I wiped my mouth.

We got in the car and headed to the airport.

"I'd give you road head, but you're still locked," I said teasingly.

"Yeah, yeah. I figured I'd leave it on for you until I got home," he said. "Then this thing is coming right off and I'm gonna stroke it to the memory of last night and this morning.

"No, you're not," I thought to myself, but "Sounds hot. Send me a video," is what came out of my mouth.

"You know I will," he said with a grin.

We got to the airport, I got out, got my luggage, and hugged him. "I'll text you when I get to the hotel," I said.

"Sounds good. See you in a week," he said.

I checked my bag, got through security, got to my gate, and about 20 minutes later, I got a text message from my cousin.

"Did you hide the keys to my cage?" he asked.

"No?" I responded.

"I can't find them," he said.

"Getting on the plane soon," I responded.

"You swear you didn't hide them?" he asked.

I got on the plane, took the keys out, put them on the tray, took a picture, and sent it.

"Swear," I said.

"OMG, I can't believe you!" he responded.

"I didn't hide them. I took them. Enjoy your week," I said.

"Ugh, I'm so mad at you right now," he responded.

I responded with a thumbs-up emoji.

"Have a safe flight," he said a few minutes later.

I responded with a heart emoji.

"Shut up," he said.

The flight and trip to the hotel were uneventful. As promised, I sent him a text when I got to my room.

"I'm still mad at you," he responded.

"Aww, I'm sorry little cousin. Did I ruin your plans with Dillon?" I asked.

"No," he responded right away.

"Maybe," he followed up a minute later.

I didn't respond. Instead, I checked flights from our home airport to Vegas, and the next flight wasn't until first thing in the morning, which was fine because it was already close to 8:00 PM in Vegas anyway. I bought him a ticket for the duration of my trip, and then I sent him a text message that said, "Check your e-mail."

"Are you serious?" he asked a few minutes later.

"See you tomorrow," I said.

"Holy shit. What do I pack? What should I wear?" he messaged me back.

"Calm down," I said. "Wear whatever you want. I'll be busy during the day, but we can hang out in the evenings."

"Thank you," he said a few minutes later.

I sent him a picture of me wearing his jockstrap and socks still, and then he sent me a picture of the butt plug still in his ass.

"If you're going to have Dillon over, be sure he puts a load deep inside you and send me a video," I said.

"Will do," he said.

We messaged each other back and forth for a little bit, and then he said he was going to pack and go to bed. I sent him the name of the hotel and my room number. I told him I'd leave an envelope at the front desk with a key in it for him and to get settled in once he got up to the room.

The next morning, I woke up to a few videos in my text messages of Ben getting used like a fleshlight. One video was Dillon throat fucking Ben, and another video was Ben's ass getting impaled by Dillon. The last video was from Dillon, and he was putting his socks and underwear that he was wearing when he came over into Ben's bag that was already by the door with a message that said, "For you. Maybe I can come along next time, too."

I went about my day at the conference and got a play-by-play from Ben throughout the day. Dillon offered to take him to the airport and offered to pick us both up since I arranged for Dillon's return flight to be the same as mine.

Then I got a flurry of messages from Ben. He got stopped at TSA. I don't know if it was a random selection or if the cage showed up on the body scanner.

"Omg. TSA stopped me, did a pat down, and then asked what was in my groin. I tried to tell them it was a chastity cage, and I didn't have the key with me, so I couldn't take it off. They took me into a little room off to the side so they could see it, and it was so embarrassing!"

"Were you wearing the butt plug?" I asked.

"No, I didn't put it back in after last night, but I also haven't shit since the night before so now both your two loads and Dillon's load are deep inside me. I feel like such a slut," he said.

"Good, keep that shame and embarrassment in mind when you realize you're flying to me just to get fucked again. Whore," I said.

"Omg, reading that is making me hard in my cage. Getting on the plane. See you soon," he responded.

I went about the rest of my day and got up to my room around 6:00. I checked on the status of Ben's flight and saw it would be landing soon. I decided to take a shower and beat off to the videos that Ben sent. Watching Ben get used by Dillon was super hot.

A short while later, I got a message from Ben saying he was on his way to the hotel. I told him I was in the room and to come straight up and that he could get his key in the morning from the front desk.

I was watching TV, and there was a knock at the door. I looked through the peephole and saw Ben. I opened the door, and he came in. I was wearing just a t-shirt and underwear.

"Long time," Ben said with a smirk.

"Too long," I said with a smirk.

I grabbed his ass and made out with him as the hotel room door closed softly.

He started to undress. First, he kicked off his shoes, which I noticed were Dillon's, and then he pulled off his shirt and dropped his pants. He was down to his socks and underwear.

"Can you PLEASE unlock me now?" he begged.

"I suppose," I said as I walked over to my backpack to get the keys.

I made a little bit of a show pretending to look for the keys.

"Uh oh," I said.

"What do you mean 'uh-oh?'" he said with a trace of panic in his voice.

"I could've sworn I put the keys in this pocket when we were home, but they're not there. They're not in any of the pockets," I said.

"Shut up," he said. "You're just fucking with me."

"Look for yourself; they're not there," I said.

He walked over to me and started to rummage through my backpack.

"Where can they be?" he asked, slightly more panicked.

"I'm not sure," I said. "If they fell out, it could've been anywhere. I pulled them out on the plane to send you a picture and then I put them right back... Oh..."

"Oh? What do you mean, 'oh'?" he asked.

"I MIGHT have put them in the seatback pocket to get up and let someone get to their seat," I said sheepishly.

"Holy shit. So BOTH keys are in an airplane that could be anywhere in the world at this point?" he asked, getting more and more annoyed.

"That's about the size of it," I said.

"Well, now what the fuck do I do?" he asked.

"I guess the first step is to have a drink. Help yourself to the minibar," I said.

"I don't want a drink! I want to get this damn cage off!" he exclaimed.

"Okay, I'll have a drink," I said calmly. "I mean, I guess this makes you a permanent bottom now."

"Not funny," he said.

"It kind of is," I said. "First, I fucked you twice within eight hours, and then Dillon came and fucked you. Seems like we're off to a great start," I said.

"When I get this off, I'm going to fuck you so hard," he said. "This is getting right up there with you pushing me about the baseball team hazing me."

"Whoa," I said. "Okay, calm down. I'll see if I can get it off. If I DO get it off, do you promise to stop being mad?"

"If you can get it off without calling a locksmith or sending me to the hospital, yes. I'll stop being mad," he said.

"Do you promise?" I asked.

"Yes, fine. I promise," he said.

I reached behind his ear and made the keys appear using that cheesy sleight-of-hand trick that people use to make quarters appear out of kids' ears.

"Oh, my God! You're such an asshole!" he said as he pushed me.

"Yeah, I know," I said. "Lay down."

He got on the bed and laid on his back. I pulled his underwear down just far enough to unlock his cage and take it off.

"While you're down there..." he said.

"Don't mind if I do," I said as I put my lips around the tip of his dick.

"Oh, shit. Really?" he asked in surprise.

"Mmhmm," I said as I started sucking, and he got hard almost immediately. He grabbed my head and held it in place while he thrust in and out of my mouth.

Once he let me up for air, I said, "I haven't eaten yet. I want you to feed me."

"Holy shit. Okay, I'm not mad anymore," he said.

"Where do you want me?" I asked.

"On your knees," he said.

I got on my knees in front of the full-length mirror. He took his underwear off completely, put Dillon's shoes back on, walked over to me, and stood in front of me. I opened my mouth and looked up at him. He caressed my face and then put his dick in my mouth. He started off slow and put his hand on top of my head. With each thrust, he went a little deeper until, finally, I was deep-throating all eight inches. I put my hands on his hips and pulled him toward me to establish a decent rhythm. I looked up at him and saw he was watching me blow him in the mirror. I kept going and made eye contact with him in the reflection. Once we locked eyes, I put a finger up his ass and really started working his dick with my mouth.

"Oh, fuck," he said. "I'm... gonna cum..."

I kept pulling him toward me with my finger in his ass. Sucking his dick, going all the way down to his balls until finally I felt his hot, sticky load spewing out of his dick. I went all the way down as soon as I felt him ejaculating and let him squirt it all down my throat.

"FUUUUUCK," he said with a moan as he grabbed my head and gave me three or four good thrusts as he finished.

I pulled back, sucking out as much as I could, and then showed him his jizz on my tongue, closed my mouth, swallowed, and then showed him my clean tongue.

"Fuck, that's so hot," he said.

I grabbed his dick and stroked it with my mouth open, trying to get every last drop of semen out of him. He had just a little bit more for me, I put it on my tongue and closed my mouth. But this time, I didn't swallow. I stood up and kissed him, putting his jizz in his mouth with my tongue.

"Aww, man. I always fall for that!" he said. "I don't even care this time because that was totally worth everything that happened today."

"Wow, really?" I asked. "You're not going to fuck me in the ass to teach me a lesson?"

"Not this time," he said.

"What if I want you to?" I asked teasingly.

"Well, maybe," he said. "But I need a few minutes before I can go again."

"No worries," I said. "Do you want to check out the strip or go eat or anything?"

"I could eat," he said.

"I already had a bunch of meat and dessert," I said with a smirk, "But we can find somewhere to eat."

I'll get dressed really quick, and then I'll be ready," I said as I walked over to his bag and unzipped the outside pocket. I pulled out Dillon's underwear and socks.

"Wait, what?" he asked.

I pulled off the underwear I was wearing and put Dillon's underwear on. Then I put Dillon's socks on and went to put my jeans and shoes on, which were really Ben's jeans and shoes, and Ben said, "Wait," as he kicked Dillon's shoes off. "Put those on," he said. I inhaled the scent from the shoe deeply and put them on.

"When did Dillon put his clothes in my bag?" he asked.

"Sometime last night or early this morning, I guess. I got a video from him putting the clothes in there and a message saying it was for me," I said.

"That's literally what he was wearing yesterday when he came over. I guess he either borrowed something or went home commando," he said.