A Familiar Sensation

Ben played a lot of team sports when he lived with me, and every once in a while, the team would travel for away games. I almost always was able to make it, which I enjoyed because I got out to support my cousin, and he always ended up staying in my room as kind of a flex that he didn't have to share with one of his teammates; plus the other benefits that came along with being alone with each other. But there was one time when something came up with work, and I wasn't going to be able to make it.

I dropped him off to meet up with his teammates so they could get going to their destination and went back home. I fired up my laptop to get the details of the project that was keeping me from traveling that weekend, and I read the e-mail that was postponing the project until the following month. Figures.

I checked airfare for the destination of Ben's game and it was ridiculously expensive to just hop on a plane a few hours after the team just to spend the weekend to catch the game and fly back. I sent Ben a text to let him know my project got pushed back, but that airfare was crazy expensive, and I apologized for missing his game. He responded with, "No worries. It'll be the first time I'll be able to sit right in weeks, but don't worry. You can wreck it as soon as I get back."

"I'm already looking forward to it. Good luck," I responded.

With my weekend now free, and no one to do, I started browsing some hookup sites. I had never actually met up with someone in real life. I usually just beat off to the thought of fucking a stranger and then going home, no strings attached. I came across a listing for a glory hole that wasn't too far from me. At first, I thought to myself, "Nah, that's weird. I don't wanna stick my dick in a hole and have a complete stranger suck me off." But then, the more I thought about it, the more it intrigued me. I put it to the back of my mind for the time being and went to poke around in Ben's room.

The best way I could think to describe his room is "organized chaos." Sports equipment all over the place, random piles of clothes, and even the "clothes chair." You know, not clean, but not dirty enough to wash yet.

I got undressed in his room and then started to put together an outfit from the clothes all around the room. I decided on a black jockstrap, mismatched ankle socks (one black one and one white one -- same style, though), a pair of jeans, a polo shirt, and a pair of high-top Jordans.

I went back out to the living room to relax and watch TV, but the thought of the gloryhole kept persisting in the back of my mind. I pulled my phone out and looked at it again. 10:00 PM, and the location wasn't that far away. Maybe a ten-minute drive.

Thinking about how I'm 100% wearing Ben's clothes and the thought of getting my dick sucked by some rando was making me hard. I looked at the time, and it was barely 5:00.

I went back into Ben's room after a while and started rummaging through his drawers. I knew he had one in there somewhere. After a few minutes of searching, I found it. A silicone cock ring. I reached down the front of my pants and slipped it on over my dick and balls. I adjusted it to where it was so comfortable, it didn't feel like I was wearing it at all. My dick started to grow, and I tucked it down so my bulge filled the pouch of Ben's jockstrap. I opened my pants and admired my package in the mirror.

I went back to the living room and pulled out my laptop to rub one out. Surely that would get the idea of a glory hole out of my head. I found some good porn and started stroking through the zipper of the jeans I borrowed from Ben. I pulled the jockstrap to the side and had my meat out. It looked a lot like a glory hole. Then, before I knew it, I was looking up glory hole porn. I think the decision was already made, and I didn't want to admit it.

I closed my laptop, stuffed my junk back in my pants, and adjust the jockstrap so everything was tucked away, and decided to go for a walk.

I don't know how long I had been walking, and it was starting to get dark so I turned around to go home. As I was walking back up to my place, I saw my car and I checked the time.

"Fuck it," I said to myself. "I can go get dinner and see how I feel about this stupid glory hole after."

So, I went to have dinner, nothing fancy, and I scrolled on my phone, and I ended up back on the advertisement for the gloryhole. It got updated. "If this is up, it's open." I decided to go check it out.

I got in my car and made my way over there.

When I got to the address, it was for an adult bookstore. I had actually been there a few times to get toys, chastity cages, butt plugs, etc. I had never been in the booths before. They had these booths where you could watch movies for a few bucks. I went all the way to the end, but the one at the end was occupied. The one next to it wasn't, so I went in to try and figure out what I was supposed to do. When I got in, I saw a hole in the wall that connected to the first booth I tried to go into. It was about the size of an apple at waist height. I picked a movie to start playing, pulled my dick out, and started fondling. It was pretty dark in the booth, but I saw movement coming from the hole. It looked like there was a piece of cloth covering it from the other side. I used my phone's screen as a light and I could see a mouth on the other side of the hole.

Now, these booths weren't super sturdy. They were a step above public bathroom partitions. The doors were full-length, and they closed, but I'm sure they could be unlocked from the outside.

Again, I said, "Fuck it" to myself and stuck my dick through the hole. Immediately, I felt the soft, warm sensation of a mouth start sucking on my dick. I kind of watched the porn I rented at the same time, but I started to focus more on this hole. I got closer to the wall, pressed all the way up against it, and put my balls through the hole, too. I felt the mouth go down as far as he could, and then he licked and sucked my balls, and then went back to sucking my dick.

Just as I was getting close to finishing, he did this thing with his tongue where he swirled the tip of his tongue around the head of my penis, and tried to deepthroat as best as he could with a wall in the way, all while fondling my balls.

He started focusing just on my dick, and I blew a big, hot load in his mouth. I could feel him sucking, and I could hear him swallowing. It felt amazing. When he took his mouth off, I pulled out of the hole and used some paper towels to clean myself up.

Then I heard a voice come from the hole, "How does it feel to be my first?"

"Dillon?" I asked in surprise.

I tucked my junk in, zipped up, and got out of the booth. I waited in the hallway, but he didn't come out. I got my phone out of my pocket and called him. Moments later, I could hear the buzzing of his cell phone coming from the booth that just sucked me off. I went back into my booth and spoke into the hole. "Get out here! Let's go!"

He came out of his booth, with a look of embarrassment on his face.

"Come on. We'll talk in the car," I said.

He walked to the front of the store without saying a word and went outside. I followed him, unlocked my car, and we both got in.

"Holy shit, dude! What are you doing? Why aren't you at the away game?"

"I got benched for academic probation," Dillon said.

"Okay, and you think sucking dick is going to fix that? Where does everyone think you are?" I asked.

"My mom thinks I'm at the game. She doesn't know," Dillon responded.

"Where are you staying until the team gets back?" I asked suspiciously.

"I don't know," Dillon said. "I haven't gotten that far yet."

"Okay, well. You're obviously staying with me. Where's your stuff?" I asked.

"Oh, I put it under some boxes behind the store. It's just a backpack and a duffel bag with my team gear," Dillon said.

I started the car and drove around to the back of the store. Dillon got out, grabbed his stuff, tossed it in the back seat, and got back in.

"Fucking hell, bro... Thanks for the head, but this isn't you," I said.

"I thought that dick looked familiar," Dillon said with a smirk.

"It's not funny!" I admonished. "You could've gotten hurt or caught something. Was I really your first? Do I need to get tested?" I asked.

"You were the first," Dillon said earnestly.

"Tonight or ever?" I asked suspiciously.

"Ever! I swear!" Dillon exclaimed.

For whatever stupid reason, I believed him. We talked on the way back to my place, and apparently, this was the first game he had been benched from, and he didn't want to tell his parents, so he just acted like he was going with the team to the away game. He didn't know what to do, and he figured he could hang out in the booth for a while so long as he kept renting movies and he got himself so worked up, that he talked himself into being a glory hole. The reason he moved up the time was because he was starting to lose his nerve.

"What the hell were YOU doing at a glory hole?" Dillon asked me.

"I have no idea, man. This is the first away game I haven't been able to go to. I got bored after I dropped Ben off, started poking around in his room, got dressed in 100% his stuff, got myself worked up, and decided, "Fuck it," I explained.

"THAT'S what it is. Something was a little off. I mean, I know you guys share clothes and shoes and you basically dress the same, but Ben wore that exact outfit like two days ago," Dillon said.

"Yeah, you've seen his room. I just picked stuff that was lying around. I'm even wearing one of his cockrings under his jockstrap," I said matter-of-factly.

"You two are too much," Dillon said. "But... I'm glad you were the first one to show up. I was so nervous, and I was about to leave when you came in. I just wasn't sure where I was gonna go after I left."

"Well, not to get too 'big brother' on you, but you gotta get your shit together. Promise me you'll never do that again," I said.

"I like the sound of 'big brother,'" Dillon said with a smirk.

"Dude! Promise me!" I said with a little bit of heat.

"Okay, okay! I promise!" Dillon said.

I felt myself relax a little. He was a good guy, but definitely needed some direction in his life.

"Are you hungry?" I asked. "I can't imagine you would be after the load I just fed you," I said with a smirk.

"Shut up, perv! You're the one who went to a glory hole because you were bored and horny," Dillon said.

"Well, if I had known you weren't going to the game, I would've picked you up for the weekend -- which is what is happening now, but with extra steps," I said.

"Fine. You're right. And yes, I'm hungry," Dillon said.

"Good," I said, "because I was nervous as hell in that glory hole, and I can probably work up a real load for you as soon as we get back."

"Oh, my God!" Dillon exclaimed.

"I'd like to say I'm kidding, but I'm not, but we can drive through for you somewhere," I said.

"Thanks, jerk," Dillon said.

"No problem, bitch," I responded.

We drove through somewhere, got a bunch of food, went back to my place, and we talked about his academic situation. I told him he's always welcome to come over to my place to do his homework and that he needs to improve his grades to get back off the bench, and that's the only way to do it.

After he finished eating, he asked if he could shower and borrow a few things. I told him of course he could, and to pick whatever he wanted from my closet or Ben's closet.

While he was in the shower, I cleaned up a bit, poured a drink, and then turned on the TV. After a while, I heard him come out of the bathroom and go into my room for a few minutes, and then Ben's room.

I lost track of time while watching TV. It could've been 20 minutes or an hour -- I honestly couldn't tell you.

After a while, I heard the tell-tale click-clack of high heels coming down my hallway. Dillon walked out in front of me, and he was wearing the ridiculous 6-inch stripper heels I got for him and Ben over spring break, thigh-high stockings, a plaid miniskirt, a garter belt, and a leather chest harness.

"It's the only way I can think to repay you," Dillon said in response to what must have been a look of surprise on my face.

"You don't need to repay me," I said, "But you definitely don't have to change into something else."

Dillon lifted his skirt to reveal himself locked in a chastity cage as he handed both keys to me.

"Good," he said, "Because we're just getting started. The team doesn't get back for two days and now you're stuck with me."

"Well, tell you what, if you get caught up on homework and missing assignments or whatever else, I'll unlock you. Otherwise, I'll give the keys to Ben to give to you on Monday," I said.

"What?!" Dillon asked in surprise.

"You're already dressed like a schoolgirl. Hit the books!" I said with a laugh.

"Can I get started on it tomorrow? I spent all that time in the shower shaving from my neck down," he said as he put his foot up on the couch next to my leg.

"You can start whenever you want, but you're not getting unlocked until you're done," I said with a smirk.

"Fine," Dillon said as he sat next to me.

"You're so cute when you pout," I said.

"Shut up and pull your dick out," Dillon said.

I unbuttoned and unzipped my jeans, and Dillon grabbed my dick and started tugging. I got hard almost instantly and then he started sucking my dick. He started to swirl his tongue around the tip of my penis again and I said, "That's how I knew it was you. That little tongue swirl you do."

"And you still finished?" Dillon asked.

"Obviously," I said, "It was a lot easier when I thought it was you.

"I'm already going to fuck you. You don't have to gas me up," Dillon said with a smirk as he stood up, turned around, held my dick in place, and guided it into his ass as he lowered himself onto my lap. Once my dick was in, he let go and slowly went all the way down, taking every inch of my meat.

"Ffffuuuuuuck," Dillon said. It was a mixture of pain and pleasure.

He spread his legs over mine and planted his high-heeled feet firmly on the ground as he started to ride me. He leaned back and laid on me as I ran my hands up and down his body. I grabbed his locked dick, played with his balls, pinched his nipples, and grabbed his throat as he started to ride me faster and faster.

I was getting close to blowing my load deep inside his ass, but I didn't want it to be over yet. I picked him up off of me, tossed him on the couch, flipped him over, held onto his harness, and fucked him from behind like the little slut he was.

I stood him up, grabbed him by the throat with one hand, and grabbed his locked little dick with my other hand as I thrust deep inside of him. His moans of pain and pleasure filled my ear as he licked and nibbled my earlobe.

Finally, I pulled out, flipped him onto his back, got on top of him, put my dick back in his ass, and started to fuck him missionary style. I was getting so close to cumming, and he could tell I was almost there. He leg-locked me and said, "Fuck me! Fuck me like you mean it, daddy!" Before I knew it, I was blowing a huge load up his ass, he was moaning with pleasure, and it just kept going. I collapsed on top of him in pure post-orgasm bliss. My dick still inside of him, sweat glistening on my forehead. He ran his fingers through my hair with one hand and put the other hand around my torso.

"That was fucking hot," Dillon said as he uncrossed his ankles from behind me.

"Yeah, I got super sweaty," I said as I pulled out of his ass and pulled on my shirt.

"Uh, that's not sweat..." Dillon said.

I looked down at my stomach, and I saw a glob of fluid at the bottom of my shirt.

"You made me cum," Dillon said with a hint of embarrassment.

"Well, that's the only way you're gonna cum this weekend, so I'm glad you got yours, too," I said as I pulled off my shirt and used it to wipe off my dick.

He went to the bathroom to clean up and came back to the living room after a few minutes.

"It's really deep inside me. Nothing came out," he said.

"Good," I said with a laugh.

He sat next to me on the couch, pulled a blanket over himself and watched TV with his head on my shoulder for a little while.

It was sometime after midnight when I said, "I think I'm ready for bed. You know you can sleep wherever you want." There was a hint of an invitation in my voice.

"I know, thanks. I think I'm gonna finish this episode before calling it a night," Dillon responded.

I went to my room, got undressed, showered, put on a pair of boxer briefs and a T-shirt, and got in bed. I'd like to say I was surprised to find Dillon in my bed, but I knew that's where he'd end up.

He rolled over to face me and said, "I hope you don't mind. You said I could sleep wherever I wanted," as he put his leg over me.

"You know I don't mind," I said. "I was hoping you'd pick here instead of Ben's bed or the couch."

"Then, why didn't you ask me to?" Dillon asked.

"I didn't want to make you feel obligated," I said.

"Obligated how?" Dillon asked.

"Letting you stay here without telling your parents where you are maybe?" I said.

"I'm 18. I can sleep over at a friend's house if I want to," Dillon said.

"Okay, okay. Don't get your panties in a twist," I said.

"I'm not wearing panties," Dillon said with a smirk.

"No, you're not," I said as I grabbed his ass and kissed his neck.

"Mmm, I like that," Dillon said.

"I know. Shut up and go to sleep," I said.

"Do you mind if I sleep in this?" Dillon asked.

"Not at all," I said. "But, do you want to take those heels off? I'm too tired for a round 3 tonight."

"Sure," he said. "Maybe, if you're lucky, I'll put them on again tomorrow."

"Oh, I know you will. I'm feeling pretty lucky," I said.

Dillon unbuckled the ankle straps and let the heels fall to the floor.

"Go ahead and get naked. You spent all that time shaving, after all," I said.

Dillon undid the fasteners on the garter belt and slid the thigh-highs off, and then he took off the garter belt and skirt. Finally, he pulled the chest harness up and over his head and let it all fall to the floor -- the only thing he was wearing at this point was the chastity cage. He curled up on my chest, put a leg over my body, and said, "Goodnight."

"Goodnight," I said as I put my arm around him.

The next morning, I woke up, and Dillon wasn't in bed anymore. I got up to use the bathroom, and went out to the living room where I saw him in the kitchen wearing nothing but the stripper heels, making breakfast.

"Bold move, frying bacon in the nude," I said.

"I'm wearing a cage and heels," Dillon said flippantly.

"Like a good little sub," I added.

"Shut up," Dillon said embarrassedly.

We ate breakfast, and I asked him if he wanted help with any of his schoolwork or if he just needed a quiet, distraction-free space to work in. He said he understood the material, but just wasn't doing it, and that he could probably get it all done the same day if he really sat down and focused on it. I told him I didn't have any plans for the weekend because I thought I was going to be working on a project, but I'd stay out of his way and let him set up at the table so he could spread out.

He sat at the table, still nude, and wearing heels, and I asked him if he wanted to get comfortable or put something on.

"I'm pretty comfortable," he said.

I looked at his feet and raised an eyebrow.

"They're not that bad, once you get the hang of them. They've got a tall platform and if I put most of my weight on my toes when I walk, I can actually get around pretty easily," he said.

I stared at him blankly.

"Shut up," he said. "I like these, and they're cute. Do you WANT me to take them off?" He asked threateningly.

"No, no, no!" I said, "It's just... that was pretty gay, bro," I said.