A gay story: 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.
“Says the guy who went to a glory hole, came in my mouth, took me home, fucked me up the ass, and cuddled with me all night,” Dillon retorted.
“Fair enough,” I said. “But, in my defense, the glory hole started as anonymous — you could’ve been a girl, and when we got back, you shaved your legs, pubes, chest, and underarms and dressed like a girl…”
“Are you trying to pick a fight just for the makeup sex?” Dillon asked incredulously.
“Hmm, maybe,” I responded introspectively. “I’m going to get out of your way so you can finish and maybe get unlocked before it’s time for you to go home,” I said quickly as I went to my room.
“Good idea,” Dillon responded with a hint of irritation.
I grabbed his duffel bag and said, “I’m going to put this in Ben’s room so it’s out of the way.”
“Whatever,” Dillon said shortly.
I took the duffel bag into Ben’s room, and dropped it on the bed. As I turned around to leave Ben’s room, I stopped, turned back around, and slowly unzipped the duffel bag. There was all Dillon’s baseball stuff — uniform, jockstrap, cup, glove, and cleats. And then there were his regular clothes.
When Dillon took a shower the night before, he used my bathroom, and he left the things he was wearing on the floor of my bathroom. I didn’t mind, of course, and I knew he was going to pick it all up when it was time for him to go home.
I looked through the regular clothes he had packed and pulled out a pair of socks, underwear, jeans, and a shirt. I took it back into my room, closed my door, and dressed in Dillon’s clothes. I put on the shoes he was wearing the day before, got on my bed, and turned on the TV.
Apparently, I had fallen asleep watching TV in my room because I was woken up to Dillon saying, “I have that same shirt.”
“Same underwear, too,” I responded without missing a beat as I pulled the waistband of his jeans down to show him what I was wearing.
“Dude!” Dillon exclaimed.
“You weren’t wearing them, so I thought I would,” I said with a grin. “Plus, you can’t go home from an away game with no laundry to do.”
“I didn’t think about that,” Dillon said.
“Lucky for you, I have plans for you to get dirty in your uniform later,” I said with a smirk.
“Oh, boy…” Dillon said apprehensively.
“Don’t worry, you’ll have fun,” I said. “How’s the homework coming along?”
“I decided to take a break,” Dillon said. “But I’m over halfway done.”
“Breaks are good,” I said. “What do you want to do?”
“Honestly, I think I want to ride your face,” Dillon said matter-of-factly.
“Well, someone’s not shy anymore,” I said.
“It took me a little bit to warm up to you again. It’s been a while,” Dillon said shyly.
“I get it,” I said. “No one is stopping you from coming over any time you want.”
“Yeah, I know,” Dillon said, “But sometimes I just wanna hang out with you one-on-one and not just be a fleshlight for you and Ben.
“Fair enough,” I said as I scooted down on the bed to lay flat on my back. “Come on.”
“Holy shit, seriously?” Dillon asked in disbelief.
“Hurry, before I change my mind,” I said.
Dillon climbed on top of me, facing away from me, and sat on my face. I licked his balls, sucked on them a little, and licked his taint. He was absolutely hairless — I was impressed that he got a razor back there without nicking himself.
I worked my way to his ass and started to swirl my tongue around. Dillon was gyrating his hips, and I felt his hands going to work on the button of the jeans I borrowed from him. He pulled my dick out and started stroking it with his hand while I continued to eat his ass.
Then he leaned down and put my dick in his mouth. I sat up a little so I could keep eating his ass while he sucked my dick. Just as I was about to cum, I heard his phone start ringing. He stopped sucking my dick, got off me, and said, “Break’s over. I’ll be back when I’m done!” As he walked away in those high heels and he spanked his ass on his way out of my room.
“Not cool!” I exclaimed as he laughed.
A few hours later, Dillon came back in my room and said, “I think I’ve done as much as I can for today. I’m fried.”
“Cool. I’m starving,” I said.
“Me, too,” Dillon said.
“Do you want to go out or order in?” I asked. “I don’t feel like cooking.”
“Well, I kind of don’t want to take off these shoes. I like being taller than you, but I’m not brave enough to wear these outside,” Dillon said.
“You know you can put them back on after you take them off, right?” I asked teasingly. “You can just say you want to order in. I’m buying either way,” I said.
“Hmm, let’s just order in,” Dillon said, “I don’t want to run into anyone who might recognize me and have it get back to my mom.”
“Good point,” I said. “Go ahead and order whatever you want from wherever you want,” I said as I handed him my credit card.
“Thanks, daddy,” Dillon said in a sweet voice.
“I’m… equally disturbed and turned on by that. Knock it off. I think,” I said awkwardly.
Dillon laughed and went to get his phone from the living room to order food.
After a few minutes, he came back into my room and said, “Okay, 35-45 minutes. Think you can finish before the food gets here?”
“There’s only one way to find out,” I said enthusiastically.
Dillon laughed and climbed on top of me, kissing me passionately. His tongue felt warm and silky soft on mine. He worked his way down, kissing my neck, chest, stomach, and eventually my dick. He opened the jeans, pulled my dick out, and started sucking like he was trying to siphon gas through a ten-foot hose.
I tossed him off of me, flipped him onto his stomach, and shoved my dick up his ass. I grabbed both arms, pinned them behind his back, and used them as leverage to pull myself into him with each thrust.
I could feel his legs kicking behind me as he bit down on the sheets. I let his arms go, laid on top of him, and used my feet to spread his legs as I wrapped my arms around his torso and held his throat in my hand.
“Oh, fuuuuck. I’m gonna cum…” Dillon said with a moan.
I kept doing exactly what I was doing when he said that, and I could feel his asshole start to clench around my dick as he approached climax. His breathing got faster, and just as he came, he let out a huge, “Uhhhhhhh!”
I pulled out, flipped him over, pinned his legs up so his knees were up by his ears, and I pushed all my meat into his ass, taking long and steady thrusts as I finished deep inside him.
I let his legs down, and he immediately wrapped them around me, crossing his ankles behind my back.
I relaxed on him and said, “Okay, what are we going to do with the next 43 minutes?” He laughed so hard he pushed my dick out of his ass.
“That was pretty funny,” he said as he looked at his phone, “But that was a pretty good session. The food will be here soon. Do you mind answering the door so I don’t have to get dressed?”
“Of course not,” I said as I kissed him.
“Careful,” he said, “I could get used to this.”
“I’m certainly not stopping you,” I said.
“I know, but you know it would make things weird with Ben,” he said.
“I know,” I said. “It’s already a weird situation as it is. I don’t want him to feel left out if I start seeing his best friend. Plus, what if we don’t work out?”
“Yeah, I know,” Dillon said a little dejectedly.
“Cheer up,” I said. “You know I’m always down to fuck you.”
“Thanks,” Dillon said even more dejectedly.
“Aww, I’m sorry. I won’t tease anymore,” I said.
“Eh, it’s alright. I know you’re just messing with me,” Dillon said.
“We can always be a throuple,” I said hopefully.
“Hmm, maybe!” Dillon said. “I’m gonna try to get cleaned up before the food gets here.”
He uncrossed his ankles, and I rolled off of him so he could get up and get cleaned up.
While he was in the bathroom, my doorbell rang. I got up, and answered the door, and set the food on the table.
Dillon came out into the living room wearing a compression shirt and really short boxer briefs, and of course, the high heels were still on. The boxer briefs were the kind that showed the bottom of his butt cheeks. The pouch of the boxer briefs cradled his locked package perfectly.
“You really like those heels, don’t you?” I asked.
“I really do!” he responded excitedly.
“Well, you can wear them as long as you want,” I said. “Let’s eat.”
We watched TV while we ate and talked, and he said it’s been nice spending time with me, even if he was getting used like a fleshlight.
“I wouldn’t say that was my primary motive for having you over,” I said defensively.
“I know, I know,” Dillon said. “It was more pro than con. I low-key like that you can’t keep your hands off me. I’m not out at school, so it’s not like I can be in a relationship openly. Plus, I like older guys.”
“Easy! I’m not THAT much older,” I said in mock shock.
Dillon laughed, “I didn’t mean it like THAT. You’re more of a big brother than a daddy, but you’re a DADDY, you know what I mean?”
“Not really,” I said, “But keep it up, and you’ll find an extra egg roll in your mouth soon.”
“Don’t threaten me with a good time… DADDY…” Dillon said with a laugh.
We finished eating, and Dillon said he was going to get some more work done. I asked him if the TV would bother him or if he preferred that I went to my room. He said the TV wouldn’t bother him so I stayed in the living room, but I turned down the volume a bit.
Dillon went back to the table and started reading. I watched him study for a little while. He was focused and never caught me staring at him. He leaned back in his chair and put his feet up on the table. The high heels really did look good on him. They fit perfectly, and the way his calf muscles flexed when he walked was so sexy.
After a few more hours, I heard Dillon sigh and stretch. He stood up, touched his toes, and cracked his neck.
“That’s it. I think I’m done,” he said. He sounded tired.
“Like, done-done? Or you’re just not gonna do anymore today?” I asked.
“Both,” he said. “I’m already off the team, I’m missing the game today, and I’m burnt out. Isn’t that punishment enough?” He asked.
“It’s a shitty situation, but there’s only one person who put you there and only one person who can get you out,” I said.
“Yeah, I know,” he said as he walked toward me. “It just feels like I’m being kicked while I’m already down,” he continued as he straddled my lap and put his head on my shoulder.
I put my arms around him and said, “Well, let’s distract you and try to cheer you up.”
“What did you have in mind?” he asked, muffed as he spoke into my neck.
“Well…” I started.
“I know that tone,” he said as he sat up with a smirk.
“Okay, fine. You’re onto me,” I said in mock defeat.
“Spill it. Your ideas are always super pervy, but they do cheer me up in the end,” he said, smiling.
“Well, it’s going to involve taking those heels off,” I said as I started to unbuckle an ankle strap.
“Aww, boo,” Dillon said.
“But don’t worry,” I said as I unbuckled the other strap, slid the heels off, and started rubbing his feet, “you can relax for a little bit.”
“Oh, my God!” Dillon exclaimed. “I didn’t realize how much my feet hurt. That feels amazing!”
I tapped his thigh and said, “Sit next to me. Put your feet on my lap.”
I put the heels on the floor and started rubbing Dillon’s feet and calves. Dillon let out little moans of pleasure. After a few minutes, he asked what I had in mind.
“Well, you mentioned that you’re missing the game today,” I said. “But there’s no reason you still can’t put on your uniform and get dirty.”
“Yeah, I kind of figured that’s where this was going,” Dillon said with a grin. “I can do that, sure.”
He put his feet down from my lap and stood up.
“Wow!” he exclaimed. “How do girls do this all day?” he asked.
“Not sure, but I’d say you’ve been doing pretty good. You’ve been wearing them since before I woke up this morning,” I said.
“Yeah, so about 12 hours, I guess,” Dillon contemplated.
“Okay, go gear up,” I said. I’ll be here.
“Yes, daddy,” he said as he picked up the heels and walked down the hallway.
“Shut up!” I said with a laugh.
I heard the door to Ben’s bedroom close, and I got up to look down the hallway. Since I had put Dillon’s duffel bag in Ben’s room, I assumed he went in there to get dressed. I went to my room and pulled out my “toy box” from the closet. I grabbed rope, lube, a Hitachi Magic Wand, and a ball gag.
I went back to the living room, dropped some of the rope behind the couch, both ends, but I left a loop at the top, and then got on the floor to pull the rope out from under the couch, so I had a bit coming up from the back of the couch and out from under in front of the couch. I took either end of the rope and pulled them to either side of the couch and around the two front legs. I put the lube, ball gag, and magic wand on the end table and poured myself a drink in the kitchen.
As I was coming back to the living room, I heard the click-clack of Dillon’s cleats coming down the hall. He was dressed in his baseball uniform, complete with his cap, eye grease stripes on his cheeks, and batting gloves.
I stood up to check him out and said, “Cup check!” while tapping his crotch suddenly. My knuckle was met with a plastic knock.
“Good boy,” I said.
“I thought I’d be authentic,” he said as he adjusted his cup. “It’s a little weird wearing a cage underneath it. It barely fits right,” he said.
“Speaking of barely fitting right,” I said. “How was the morning wood?”
“Brutal,” he said pointedly.
“I’m surprised you didn’t wake me up for some relief,” I said.
“You looked so peaceful, and you probably needed the rest after yesterday,” he said, almost caringly.
“You’re probably right. I appreciate that,” I said. “Now sit down. I’ve got plans for you,” I said as I pushed him down onto the couch.
I got on the floor, and grabbed the end of the rope that was wrapped around the left leg of the couch, and started to tie it around his ankle. I did the same with the other side, and other ankle, and then I pulled the loop of the rope from behind the couch, causing his legs to spread. I pulled as far as he was still comfortable, and he was pretty flexible, so his legs were pretty well spread. I took the length of rope from behind the couch and told him, “Put your hands behind your head.” He did as he was told, and I tied his hands together behind his head. Now, he was in a situation where if he tried to bring his feet together, it would pull his arms further back behind him, and if he tried to bring his arms down, it would spread his legs even more.
Lastly, I told him to open his mouth, and I placed the ball gag in and fastened it behind his head. It was a red silicone ball gag with leather straps and a little loop build into the buckle that I could put a tiny luggage lock on to prevent him from unbuckling it without permission.
“Don’t go anywhere,” I said ironically.
I went to the kitchen and rummaged around my junk drawer to find a luggage lock. I found a tiny brass lock with the key in it. I tested the key and the lock popped open. “Perfect,” I said. I left the key on the counter and went back into the living room. I tugged on the ball gag, and there was a little too much give, so I tightened the strap just one more notch, which was a bit much, but it didn’t hurt him. That ball gag definitely wasn’t going anywhere now. I put the lock on the loop and clicked it shut.
He was already starting to drool. I licked the corner of his mouth, and he moaned with desire.
“Are you ready for this?” I asked as I picked up the magic wand.
The look of confusion on his face was fantastic.
I turned on the magic wand and placed it on the middle of his cup for a few seconds. He started to moan, and I took the wand off.
I continued to tease with the wand, occasionally licking his neck and face while gently pinching his nipples.
His breathing was intensifying, and I started to feel bad for him.
“Okay, okay. I’ll let you cum,” I said as I placed the wand on the cup and held it in place.
After a few minutes, he was breathing hard, trying to gyrate his hips to find just the right spot. Apparently, he found it because when it was just right, he froze in place, shut his eyes tight, held his breath, and then suddenly let out a big sigh of satisfaction as he convulsed with each ejaculation.
I continued to hold the wand on his cup and the look of surprise on his face said it all.
“Yup, you’re gonna go again,” I said devilishly.
I started to get him all worked up again. Repeating everything I did the first time. Licking his face and neck, playing with his nipples, except this time, I stopped when I could tell he was getting close again.
“You know, you’ve been such a good boy this weekend. I think you deserve a reward,” I said as I unbuckled his belt.
I unsnapped his baseball pants, but his legs were spread so far apart, I wasn’t able to get them down past his hips.
“Okay, I’m going to lift this side of the couch so you can bring your legs together, just for a second while I pull your pants down, but then the rope is going right back around the leg of the couch where it is now, got it?” I asked him.
He nodded fervently.
I lifted one side of the couch just enough to pull the rope out. He pulled his leg closed, and I pulled down his pants and jockstrap around his ankles. There was a big, sticky mess inside his cup.
“Okay, spread,” I said, and he complied.
I put the rope back around the leg of the couch and pulled on it to make sure it was back where it was.
I could see his locked dick straining against the cage, and I turned the vibrator back on and held it on the cage.
I didn’t think it was possible, but his dick was straining even more.
“Poor little guy, just wants to come out and play,” I said teasingly.
Dillon shot me a look of contempt.
“Don’t worry, your reward is coming,” I said. “I’ll be right back,” I teased as I placed the vibrator on the couch between his legs and took his belt off his pants to strap the handle of the vibrator to his thigh.
He started to moan with incomprehensible pleasure.
I went to my room, grabbed the keys to his cage, and grabbed a towel out of the bathroom.
I came back to the living room, put the towel over his face, undid the belt from around his thigh, and turned the vibrator off.
He was breathing hard, and I asked, “Are you ready?”
“Mm-hmm,” he muffled around the ball gag.
I unlocked him and slowly took the cage off his dick. I set it down on the end table and grabbed his dick in my hand and started stroking.
“Mmmmmm,” I heard from under the towel.
I wordlessly put my mouth on his dick and started sucking. Lightly and slowly to start.
“MMMMMM,” was the response.
“Do you like that?” I asked coyly.
“Mm-hmm, mm-hmm,” he responded.
“Then you’re really going to like this,” I said as I quietly pulled down my pants and underwear.
I grabbed the lube from the end table, put some in my hand, worked it onto his dick, and then put some on my asshole.
I stood in front of him, facing away from him, and slowly lowered myself onto him.
“OH EYE GAH,” he tried to get out.
“That’s right, you’ve earned it,” I said as I slid all the way down to the base of his dick.
I slowly went up and down. I didn’t want to go too fast because I didn’t want him to finish right away.
I’d stop right at the tip of his dick, and he tried to thrust, but the rope was doing it’s job and kept him right in place. For every inch he tried to give, I pulled away further and further.
“Okay, are you ready for the real thing now?” I asked.
“Hmm?” Dillon asked confusedly.
“I’m going to untie you and you can do whatever you want,” I said.
“Mm-hmm!” he said excitedly.
I reached behind his head and freed his wrists. He immediately grabbed my hips and pulled me down. He wiggled his legs together and stood up with me on his lap. He was stronger than I thought. He pulled the towel off his face and tossed it to the side, and then he turned us around so I was facing the couch, and he pushed me down, held onto my hips, and really drove it home.
He fucked me so fast and so hard that I felt his hot, sticky jizz being shot deep inside me before I knew what was happening. He finished with a few final thrusts, slowly pulled out, grabbed the towel, wiped off his dick, and pointed to the ball gag.
I was trying to catch my breath, and I said, “Kitchen counter.”
He untied the rope from his ankles, pulled up his jockstrap and pants to mid-thigh, and walked to the kitchen.
He unlocked the ball gag in the kitchen, came back out to the living room, and said, “Best. Reward. Ever.”
He picked up the towel, wiped out the inside of his jockstrap the best he could, started to pull it back up, stopped, and asked, “Do you want me locked again?”
“Wow, did it really only take a day to break you?” I asked jokingly.
“Shut up,” he said. “You said I had to stay locked until I got caught up with my work.”
“Well, how much more do you have left?” I asked.
“I dunno. I can probably get it done before I go home tomorrow,” he said.
“Okay, well if you promise me you’ll get it done before you go home tomorrow, you don’t have to lock up again,” I said reluctantly.
“Yay! Thanks!” he said joyfully as he kissed my cheek.
He pulled the base of the cage off, set it down on the end table, and pulled his jockstrap all the way up. He turned to face away from me and asked, “Are the straps twisted?” He just wanted me to look at his ass. “Nope, you’re good,” I said.
He pulled up his pants, zipped up, and snap them shut. He took off his gloves, put them in his back pocket, and picked up his belt.
“You don’t have to stay dressed in that if you don’t want to,” I said.
“I don’t mind,” he said. “Plus, I know you want to fuck me in it.”
“You’re absolutely right,” I said.
I was sitting on the couch, and I pulled my underwear and pants back up.
“You don’t want to go clean up?” he asked.
“That load is so deep, it’s not coming out until tomorrow,” I said.
“Hmm, good point,” he said with a grin as he sat next to me and put one leg over mine. He took off his baseball cap and put it on me.
“Cute look,” he said. “You should keep it. I have more.”
“Thanks,” I said a little awkwardly.
He adjusted his pants, socks, and baseball stirrups and rotated his foot.
“No matter what I’m wearing, I’m comfortable with you,” he said.
“Are you asking me to go steady?” I asked jokingly.
There was a heavy pause.
“I think so,” he said.
“Then I think so, too,” I said matching his energy.
“Shut up,” he said. “It would be too complicated and weird.”
“I’m okay with complicated and weird. Look at you, glory hole boy,” I said.
“Shut up!” he said with a laugh. “Fine. We’ll talk about it later.”
“Maybe we can fuck on it,” I said as I grabbed his cup and jostled it around.
“Hmm. Maybe,” he said lustfully.
We sat together in silence for a few minutes with his head on my shoulder, and I said, “So you really just wiped your load out of your jock and put it back on like nothing?”
“I mean, I normally get all sweaty and gross in it for at least two and a half or three hours. I don’t see how it’s much different,” he said with a shrug.
“Gross. You really are a boy,” I said.
“I can take it off if you want,” he said threateningly.
“That might not be such a bad idea. You can borrow one of Ben’s. Top drawer of his dresser,” I replied.
“Seriously?” Dillon asked.
“No, of course not. I’m just saying, if you WANT to, you have options,” I said.
“Okay, I was rethinking this whole situation if you’re gonna be weird about a dirty jock,” he said.
“I literally had my tongue in your asshole earlier. I think I’m okay with a crusty jock,” I said.
Dillon turned red. “I forgot about that,” he said.
“I was that memorable, huh?” I asked teasingly.
“I was trying to give you blue balls since you had me locked up,” he said jokingly.
“Hey! You locked yourself up! I just took it a step further,” I said.
“True. That kind of backfired on me, didn’t it?” Dillon said.
“Yeah, but it worked out in the end,” I said.
“So what do you want to do now?” Dillon asked.
“I didn’t really have anything in mind. My whole weekend was cleared to work on this project that got postponed,” I said. “Is there anything you want to do?” I asked.
“Well, I don’t really want to go out, and not just because I don’t want anyone to see me. I kind of like just being here with you,” he said shyly.
“We can do that,” I said. “Do you want to watch a movie? Have a drink? Play a board game?” I asked.
“Board game?” Dillon asked mockingly. “What is this? 1945?”
“Yeah, imagine us getting this cozy in a foxhole,” I said.
“Okay, why don’t you get comfortable while I find something to watch?” he asked.
I stood up, kicked off his shoes I had been wearing all day, took off his pants I had borrowed, and sat back down.
“Done,” I said.
“Well, that was easy,” he said with a grin. “Do you want anything from the kitchen?”
“Would you mind topping me off?” I asked as I handed him my glass.
“Again?” He asked with a smirk.
“Hmm, maybe not quite so soon. You’re bigger than I remembered, and I’m a little sore now,” I said.
“Aww, and you even used lube,” Dillon said with a pout.
“It’s okay,” I said. “I’m sure I’ll be fine by tomorrow.”
Dillon went to the kitchen and, a few minutes later, came back with a few snacks and two drinks.
I handed him the remote and said, “You said you wanted to pick.”
“Well, I didn’t think you were just gonna take your, my, pants off and call it done,” he said.
“Our pants,” I said playfully.
“Hah, I like it,” he said as he took the remote from me.
He sat down next to me, put his feet up on the coffee table, and leaned against me.
He scrolled movie options for a while before just hitting play on something and setting the remote down.
“It’s not like we’re going to watch the whole thing anyway,” he said mischievously.
“Well, in that case, you should take your pants off, too,” I said, matching his energy.
“Good idea,” he said as he stood up.
He unbuckled his belt, unsnapped and unzipped his pants, lowered them to his knees, sat back down on the couch, and asked, “A little help?”
I pulled his pants off over his cleats and tossed them on top of “our” pants that were on the floor next to the couch.
He unbuttoned his jersey and tossed it over me, landing it on the pile of pants. His undershirt was a typical 3/4 length compression shirt that was stretched tight across his chest, and I could see the definition of his abs.
He put his leg over mine and leaned against me again.
We got about halfway through the movie before he started rubbing my crotch.
“It’s so weird to see you in my underwear,” he said.
“Careful, or I might keep them,” I said. “They’re pretty comfortable.”
“Only if I get to keep something of yours,” he said.
“Sounds like a fair trade to me,” I said.
He pulled my dick out and got on his hand and knees on the couch, and started sucking it. I reached behind him and started fingering his ass.
He got me good and slobbery and then laid on his back, with one leg up on the back of the couch, and said, “Fuck me.”
I got on top of him, worked my dick into his ass, and started pumping. He put his arm behind his other leg to hold it up so I could go deeper.
He took the hat he had given me off my head, turned it around, and put it back on me so I could lean down and kiss him.
“Yes! Just like that!” he exclaimed in between kisses.
I did exactly as I was told and kept pumping, just like that, and then I started to erupt deep inside him again. I leaned back and saw the tip of his dick poking out from the top of his jockstrap’s waistband.
I grabbed his dick with my hand and played with the tip using my thumb. There was a little bit of precum that I licked off my thumb while looking him straight in the eyes.
I pulled out of his ass, sat up on the couch, and said, “Put it in my mouth.”
He stood on the couch, with each foot on either side of my legs, and put his dick in my mouth. He held on to my head and started off slowly, but quickly progressed to skull fucking me.
I pulled back, looked up at him, and said, “You better shoot it down my throat.”
He put his dick back in my mouth and was going all the way in so I was deep throating him. He found just the right spot where he could pump in and out of my throat, and just as he was cumming, he pushed all the way to the point where my nose was squished up against his body. He held my head in place while I felt his cock throbbing in the back of my throat.
He slowly pulled his dick out; I sucked and licked the tip as it passed over my tongue.
He tucked his dick back into his jockstrap and pulled the cup out of the pouch, and put it on my face. I took a deep whiff and rolled my eyes.
“Okay, you smell pretty good,” I said as he tossed the cup on the other side of the couch.
“Thought you might like that,” he said.
“You were right,” I said. “I have no idea what’s happening in this movie. Do you want to go to bed?” I asked.
“Sure,” he said with a shrug as he stood up.
I got up and followed him down the hall to my room. The click-clack of his cleats echoing in the hallway filled my ears.
He sat on the bed, held a foot up at me, and asked, “Do you mind?”
I walked over to him and unlaced the cleat, pulled it off his foot, held it up to my face, and inhaled deeply.
“I don’t think I ever realized how much I like how you smell,” I said as I dropped the cleat and held his foot to my face.
“Good, because I can’t control that,” he said with a laugh. “Take the stirrup off; it won’t stay on through the night, but I’ll leave the socks on.”
He lowered his foot and gave me the other one so I could repeat the process.
He stood up in front of me and for the first time that weekend, he was back to being shorter than me.
“I forgot how little you are,” I said teasingly.
“It’s literally just an inch and a half,” he said annoyedly as he took off his shirt and tossed it in my face.
“I know, I know. I just like teasing you,” I said.
“I know,” he said as he got into bed.
“So just a jockstrap and socks tonight, huh?” I asked.
“You don’t mind, do you?” he asked.
“Not at all!” I said.
I took off my shirt, so I was just in his boxer briefs and socks. I got in bed with him and turned off the light. He laid his head on my chest, put an arm and leg over me, and was quickly asleep.
The next morning, I woke up before Dillon. He was on his back and looked serene, sleeping next to me. I lay next to him, admiring his athletic physique. I slowly pulled back the covers to see the outline of his morning wood in his jockstrap. I couldn’t help myself. I slowly went down to his crotch and pulled his dick out from the side of the jockstrap pouch, and put it in my mouth.
I started sucking on the tip, gradually making it all the way down his shaft. After a few moments, I felt his hand on the back of my head, gently pushing encouragingly. I looked up and locked eyes with him as I continued to blow him.
“Good morning,” he said with a smile.
I turned around and got on top of him in the 69 position. He pulled my dick out and started sucking, and we blew each other for a short while before I started fingering his hole.
I got off of him, turned back around, lifted his legs onto my shoulders, and asked, “Are you ready to get fucked?”
“You know I am,” he said.
I slid my dick into his ass, and his tight, warm hole felt amazing as I went all the way in. I started pumping slowly as I stroked his dick with my hand. Eventually, my rhythm increased as I held onto his dick for leverage, and I came deep inside him again.
I pulled out and lay next to him, admiring him again. I was on my stomach, caressing his stomach, tracing the outline of his abs with my finger.
“My turn,” he said with a grin.
Before I could say anything, he was pulling down my boxer briefs, tossed them across the room, sat on my thighs, and slid his dick into my ass.
I inhaled sharply, and he slowed down.
“You good?” He asked.
“Yeah, just be gentle,” I said softly.
He put his hands on my back as he started pumping my ass with his dick, starting off slowly and gradually going faster and faster.
Suddenly, he pulled out. He couldn’t have finished that fast, could he?
“Bend over the edge of the bed,” he said.
I guess he wasn’t done yet. I did what he said. He stood behind me, put his right foot up by my shoulder, and worked his dick back into my ass. I had my hands up above my head, and I was gripping the sheets as he plowed into me.
He readjusted his stance, and before I knew it, his foot was on my face, pinning me down with both his dick and his foot. It was so hot, I thought I was going to cum again just from getting fucked. I grabbed his ankle to encourage him to keep his foot on my face, and he started fucking me faster and faster until he came deep inside my ass again. I could feel his dick throbbing with each squirt of hot, sticky jizz. Those throbs were my favorite.
He took his foot off my face, and pulled out of my ass.
“I could get used to this,” he said.
“I’m gonna have to if you’re gonna keep fucking me like that,” I said as I stood up.
“I’ve lost track of how many of your loads are inside me just from the last few days,” he said with a grin.
I walked over to my bedside table, opened the drawer, and pulled out a jeweled butt plug.
“Turn around,” I said as I walked toward him.
“Oh, boy…” he said as he turned around.
I got right behind him, put my arm around him, and put the butt plug in his mouth. He sucked on it as I pulled it out of his mouth, and I put it in his ass.
“Come take a shower with me,” I said.
“Yes, daddy,” he said in a sweet voice.
We went into the bathroom together and got undressed. I started the shower and got in. Dillon followed right behind me. It wasn’t a huge shower, but it wasn’t super tiny, either. We both fit just fine, and there was enough room for a third, but we had to take turns under the shower.
We were getting cleaned up when Dillon accidentally on pupose dropped the soap. I laughed and said, “Maybe later — leave the plug in. You can definitely blow me, though.” Dillon shrugged and said, “Better than nothing,” and got on his knees. He gave me an enthusiastic blow job, and after a few minutes, he stopped and stood up.
“Oh, is that what we’re doing today?” I asked.
“Yup!” Dillon said matter-of-factly. “This way you don’t forget to fuck me one last time before I head out.”
“About that,” I said as I finished rinsing off and stepped out of the shower.
“Yeah?” Dillon asked with a note of confusion in his voice.
“I have an idea I want to run by you. Meet me in the living room after you’re dressed,” I said as I picked up the jockstrap Dillon had been wearing and put it on.
Dillon started to wash his hair and body as I walked out of the bathroom.
I looked around and saw clothes strewn about everywhere. I started to pick up Dillon’s things and took them with me into Ben’s room, where his duffel bag was still on Ben’s bed. I put the clothes he had worn over the weekend in the duffel bag and pulled out the knee high baseball socks Dillon had been wearing the day before. I put those on and then grabbed a pair of Ben’s jeans and a shirt from Ben’s various piles of clothes. I stepped into a pair of Ben’s shoes — a well-worn pair of Osiris D3 2001 in black and white, a personal favorite of mine.
I heard the shower turn off and I made my way to the living room, where there was more clothes still. I saw the plastic protective cup that Dillon was wearing with his jockstrap and I quickly grabbed it and put it back into the pouch of Dillon’s jockstrap that I was now wearing.
I couldn’t believe I was wearing Dillon’s cum-stained, sweaty jockstrap, especially after just getting out of the shower. Just the thought of it was turning me on.
Dillon came out into the living room, completely dressed, carrying his duffel bag. He was picking up his clothes as we walked around the coffee table to sit next to me.
“I tossed some of your stuff in there already,” I said, hoping he wouldn’t notice he was missing a jockstrap and a pair of socks.
“I noticed, thanks,” he said as he rolled up the jeans I borrowed and his baseball uniform pants and tossed them in his duffel bag.
“You okay?” I asked. He seemed a little off.
“Yeah, I’m fine. It’s just… time to go home… ya know..?” He said a little sadly.
“Aww, it’s okay. You know you can come over any time you want,” I said. “Would it make you feel better if I gave you a key?” I asked.
“Actually, yeah,” he said.
“Then I’ll give you a key. I mean it; you can come over any time you want. No one has to be here, but you can’t bring other people over — that’s my only condition,” I said.
“I’d only come here to see you and Ben, anyway,” he said.
“And definitely the next time you need some place to crash, right?” I asked.
“Probably,” he said with a smirk.
“You better,” I said.
“Okay, fine. You talked me into it. I promise,” Dillon said. “So what’s this idea you have?” he asked.
“Well, I was thinking, why don’t you text your mom to tell her you’re catching a ride with Ben and that I don’t mind dropping you off at home since we’re already going to be out that way anyway?” I asked.
“Oh, sure. That would be great, thanks,” he said gratefully.
“Finish putting your stuff away because it’s almost time to go if we’re gonna be on time,” I said.
Dillon got up from the couch, collected all his work from the table, and put it all away.
After everything was put away and he was ready to go, he came back and sat next to me on the couch.
I looked over at the heels that he had left on the floor and said, “You know… we have a little bit of time before we actually have to leave,” as I looked at the heels. “One more time?” I asked.
He kicked off his shoes, pulled off his socks, and dropped his pants so fast; it was almost comical. He stepped into the heels and fastened the ankle straps. “I thought you’d never ask,” he said as he stood up and bent over in front of me.
“So you were just going to keep that butt plug?” I asked.
“I’ll bring it back,” he said as he pulled out the butt plug and set it down on the end table.
I pulled my pants and the jockstrap I borrowed from Dillon down. Thankfully, he didn’t notice as he started sucking my dick.
I stood up, bent him over the couch, and started fucking him slowly. His knees were up on the couch and I grabbed one of his ankles for leverage.
Dillon started moaning. “Yes! Fuck me! Make me yours!”
I pounded him deeper and faster. I let go of his ankle and gripped his hips as I unloaded deep inside his ass.
“Your’re such a good little slut,” I said as I pulled out and wiped my dick on his ass.
“And you’re a dick!” he said with a laugh. “Did you really just wipe your dick on my ass? I barely got out of the shower.”
“Just marking my territory,” I said with a smirk. “You told me to make you mine.”
“Okay, I can’t get mad at that,” he said as he walked down the hall to the bathroom. The click-clack of the high heels faded as he walked away.
After a few moments, he came back out, grabbed the butt plug and put it right back in his ass like it was nothing.
“I’ll bring it back next weekend,” he said as he kissed my cheek.
He sat down on the couch and held his foot up. “Would you mind?” He asked.
I undid the ankle strap and slipped the high-heeled shoe off his foot. He lowered his foot and raised the other so I could repeat the process.
I set the shoes down on the couch as he got dressed again. I pulled my pants up and said, “I think we should head out so we’re not late meeting the team.” I walked into the kitchen and started rummaging in the junk drawer.
“Yeah, I suppose,” he said a little dejectedly as he put his shoes on and stood up.
“Cheer up,” I said as I handed him a key to the door.
He smiled and said, “I thought you were just talking about it. I didn’t think you’d give me a key today.”
“Yeah, well. Just don’t do anything weird, like stand over me at 2:00 in the morning,” I said.
“Even I’m not THAT weird,” he said with a laugh.
He gathered his things, and we left. He put his bags in the trunk of my car and we went to pick up Ben.
Once the team arrived, I saw Ben looking around for me. I waved my arm to get his attention and he came jogging over. He was surprised to see Dillon in the car.
“Hey! What’s up? What are you doing here?” Ben asked Dillon.
“It’s a long story,” I interjected. “I’ll tell you later. We’re gonna take Dillon home,” I said.
“Ooh, sounds fun, but I need to shower first,” Ben said.
“His home, not ours. Horndog,” I said with a chuckle.
“Oh, boo!” Ben said half-jokingly, half-disappointedly.
“I know, I know. I’m sure you’ve got lots of laundry to do, but if you clean your room, your friend can come over next weekend,” I said mockingly. “Get in, and let’s go.” I said.
Ben tossed his stuff in the back seat and we got in the car and drove Dillon to his place. Ben was telling us about the game, giving us the highlights and how he had to share a room with one of the other guys, and it was weird with me not being there.
We got to Dillon’s place, and I pulled into the driveway, put the car in park, and popped the trunk so he could get his stuff.
Dillon and Ben both got out of the car. Dillon got his stuff out of the trunk, and Ben moved around to the front seat. Ben and Dillon dabbed it up and hugged before Ben got his stuff out of the back seat and put it in the trunk. While Ben was doing that, Dillon came around to my window, leaned down, and said, “Enjoy my jock and socks, perv. You didn’t think I would notice? I’ll get them from you next weekend.” He smirked over his shoulder and started to walk up the driveway.
Ben got in the front seat and asked, “Why did Dillon have his duffel bag if he’s benched for his grades?” Ben asked.
We waited for Dillon to get inside before we left, and I explained most of what happened while Ben was away for the weekend.
I asked how Dillon’s home life is, and Ben said he didn’t know.
“You two don’t really sweat the details, do you?” I asked jokingly.
“Yeah, I guess not,” Ben said introspectively.
I told Ben I had given Dillon a key and said we had an open-door policy, and he’s always welcome. Ben liked that I looked out for his friend.
We got home, and I helped Ben with his duffel bag while he grabbed his small suitcase, and we made our way inside.
Ben immediately spotted the high heels I had left on the couch, turned around to look at me, and said, “Oh, THAT’S what you two were doing all weekend!” A little accusingly and a little hurt.
“Well, kind of,” I said defensively, “But there’s more to it.”
Ben crossed his arms and looked at me expectingly.
“Okay, tell you what, go take that shower you wanted and I’ll tell you everything you want to know,” I said.
Ben thought about it for a moment and asked, “Everything? Do I even want to know? Did you do it in my room!?” I laughed and said, “Everything, and we didn’t do anything in your room. I promise.”
“Fine,” Ben said, “But you better tell me EVERYTHING!”
“I will, I promise,” I said.
Ben disappeared to his room, grabbed a few things, and got in the shower. I heard the water turn on, and after about 20 minutes, I heard Ben coming down the hallway.
He was wearing his leather chest harness and a pink miniskirt. He sat down on the couch wordlessly and started to put the heels on.
“Hopefully, this is okay, and you’re not too tired for me,” he said with a hint of jealousy.
“It’s always okay, and I’m never too tired for you,” I said confidently.
“Are those my shoes?” he asked as he looked at my feet.
“Yup,” I said. “I knew you wouldn’t mind.”
“You’re right… So… Tell me everything…” he said as he sat back and crossed his legs.
I sat next to him and shared every detail of what transpired over the weekend.
“A glory hole?” he asked, equally incredulous and disgusted.
“I’m not proud,” I said. “But it worked out for the best for both of us.”
“Well, given what could have happened to either of you, it was the best possible outcome,” Ben said matter-of-factly.
“So, am I in trouble?” I asked, trying not to sound too condescending.
“No, of course not. I’m just jealous,” Ben admitted.
“How much did you miss me this weekend?” I asked with a grin.
“You know how much, but I don’t want to know the answer if I ask you that same question,” Ben said jealously again.
“Aww, no one can replace you,” I said. “Stand up, let me take a look at you,” I said.
Ben tried to suppress a smile, but he stood up and turned around. I started to push down on his shoulders and said, “Get on your knees.”
He happily obliged and started to undo my pants.
“Nice jock,” he said sarcastically.
“I stole it from Dillon. Socks, too,” I said.
Ben rolled his eyes and pulled my dick out to start sucking on it.
“Tastes like him,” Ben said, trying to make me jealous.
I stood him up, turned him around, and slipped my dick in his ass.
Ben gasped in surprise as I pushed all the way in.
“That’s because I fucked him in the ass, standing right where you are, wearing those same shoes almost two hours ago,” I said as I held onto his chest harness, bent him over, and started thrusting.
Ben moaned in pleasure as I continued to fuck him and reached down to stroke his dick.
Just as Ben started to cum, I began to thrust faster, making sure we both came at the same time.
I pulled out of Ben’s ass, spanked him once, and pushed him onto the couch.
“You’re such a dick,” Ben said as he caught his breath.
“You are what you eat?” I asked ironically.
“Oh, my God! You blew him, too?” Ben asked incredulously.
“Well, he started it,” I said defensively. “Don’t worry, you can reclaim what’s yours as often as you want today and all next week,” I said. “I’m not sure if anything is going on next weekend, but don’t be mean to him when you see him tomorrow. He was in a tough situation and really bummed about missing the game.”
“I know!” Ben exclaimed. “That’s what’s making it so hard to be mad.”
“Okay, okay. Let’s stop trying to piss each other off,” I said. “Truce?”
“Yeah, I think that’s best,” Ben said.
“You’re definitely keeping those shoes on,” I said.
“And you’re definitely going to change out of that jock,” Ben said.
“Socks, too?” I asked.
Ben rolled his eyes and asked, “What happened to the truce?”
“You’re right! I’m sorry,” I said.
“Maybe if you can stop being an asshole for two minutes, you can change into some game-worn gear before I put it to wash,” Ben said with a smirk.
I kicked off his shoes and stripped down from the waist down.
“That’s more like it,” he said as he walked over to the laundry room to get his duffle bag.
He walked slowly into the living room, knowing how much I like the click-clack of high-heels on wood floors. He dropped his duffel bag at my feet and said, “Help yourself.”
I bent down, unzipped his duffel bag, and was immediately overwhelmed by the scent of musky sports gear.
“Oof! No wonder you wanted to take a shower when you got home. I know you showered after your game and this morning, but I bet half the dudes on your team skipped. I can only imagine what it smelled like on your way home,” I said as I picked through his gear.
“Exactly,” he said.
“So, I can pick anything?” I asked.
“Anything,” he said. “But, I get to watch you put it on.”
“Fine by me,” I said. “Not like I wasn’t just balls deep in you five minutes ago.”
“Yeah, yeah. Get dressed, or I’m gonna be balls deep in you in a minute,” he said.
I froze in place.
“Oh, yeah?” Ben laughed. “I can get it up again.”
“I bet you could,” I said as I pulled out his jockstrap, cup, socks, and stirrups he wore for his game. “Is this game-winning gear?” I asked.
“Yup, that’s what I wore on gameday,” he said.
I pulled everything on, and put on his cleats.
I sat next to him on the couch and he put his leg over mine.
“Nice and smooth,” he said.
“I love it when you shave everything,” I said as I lifted his arm over his head to inspect his armpit.
“I know,” Ben said with a smirk.
We spent the afternoon talking about how the game was and how his trip was, but we ended up going to bed a little early since we both had to get back to regular life the next day.
“One more before bed?” I asked Ben as I grabbed his crotch.
“Only if you let me sleep with you,” he said.
“Did you have someone else in mind?” I asked.
“I mean actually sleep. In your bed. Idiot,” he said teasingly.
“Oh, sure!” I said. “It’s been a while since you’ve done that. It might motivate me to wake up early tomorrow.”
We went to my room, where I blew him, and let him cum down my throat while he pinned me to the mattress and fucked my face. I fucked him one more time, kicked off his cleats, and fell asleep in his stinky, dirty baseball gear. He fell asleep in the chest harness, skirt, and high heels. I woke up before him, and he was practically in the same position he was in when I rolled off of him the night before.
He was lying on his stomach, so I ate his ass and fucked him one more time before we both got up to shower and get ready for the day.
“See you tonight,” I said as I left for work.
“Have a good day,” Ben said as he left for school.