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Hello all! Before I start the next story in my “The Senior” series, I wanted to share that since I began writing, uploading, and reuploading these stories on here some things have changed. While I have been sharing my experiences with wedgies on here, these stories thus far have been about my experiences with them as a child and teenager. This didn’t initially bother me because I was sharing and, in a way, reliving these memories through my writing. But it bothers me now. 

Had my experiences with Chase concluded while we were both underage, I would have just stopped writing these stories all together. Yet this is not the case. So, this next part (and the final part following that) will take place four years after the previous story. When we were both consenting adults. I hope you enjoy,

I was sitting at home alone. Well, I was sitting alone in the house where I grew up. I was visiting my parents during a short summer break from the musical theater conservatory I was attending. I hadn’t been home in over ten months. The conservatory went by a unique school schedule, so the week I was home didn’t coincide well with my parent’s work. As both are teachers, they still had school. It was nice being away from my classes, rehearsals, and at my part-time work in Times Square retail. So, things were busy. I was on the couch, a bag of pretzels in my lap as I watched some current popular TV show. My phone vibrated.

“Hey”, the text read.

I immediately recognized the phone number. I had deleted his contact multiple times. I even blocked the number once. Yet, those numbers were as familiar as his name.

“Hey”, I text back.

I pause the TV, redirecting my attention to my phone. I pushed the bag of pretzels aside. The text bubbles (a new IOS feature at the time) visualized three dots, Chase writing a response.

“I saw you were in town. How have you been? Chase texted.

At this time, it had been years since we had communicated with each other. And even longer since we’d last seen each other. Last time I had seen him, I was a Junior, and he was in town on Spring Break from his college in Colorado. We’d met up at my place and almost gotten caught by my parents. We quickly averted detection by sneaking out through the garage, but the stress of the moment gave me pause. Had me so scared of being discovered as anything other than “appropriate” or “normal” that I had (again) cut Chase out of my life.

“I am in town, I’ve been pretty good” I type on my phone, before deleting it.  

“Yeah, it’s been chill”.

I send the text and quickly place my phone face down as far away on the couch from me as I can reach. The phone immediately vibrates, but I force myself to remain still. The similar pattern presenting itself. He texts, I reply, he texts, I reply. Then minutes go by with nothing. Those minutes used to torture me, even when sometimes those minutes turned to hours, or the rest of the night. I promised myself I wouldn’t obsess over this again. That I was better than this. I remained still for just over five minutes before gently reaching over to my phone.

“Give any wedgies in the big apple yet?” Chase texted.

He skipped passed the unnecessary formalities. I hadn’t wedgied any guys in NYC at that point. There wasn’t any time, and I had my own revelations I was working through. Within a month of living in NYC, I had come to understand and accept that I was so far in the closet that I found Christmas presents. I had started trying things on in my new “out” life. Mostly through chats on dating apps or…. well, that’s all I did. I was out to my classmates at school, but back home I slipped back into the guy I was before I moved to NYC. Chase had been out for years by this point.

“I haven’t, too busy! Lol =(“ I reply.

“I have been thinking about the one’s you’d give me.” Chase texts.

“Really?” I reply.

“Yeah, it was hot”. Chase replies.

I politely ignored the fact that I was sporting blushed cheeks. Also, my hard on. I was ignoring that too. My phone vibrated.

“Wanna come over? I can pick you up.”

I looked at the phone in disbelief. After all that we’d been through. The shame that I felt and sometimes still have. The times that we’d avoid each other at all costs. Here he was again, offering to pick me up. To spend time with him. To wedgie him. It’s as if the closeted, hidden high school version of myself peeled away. I stood up and hopped in the shower, but not before typing and sending my response.

“Sure, you know where I live.”

When I opened Chase’s front car door, he looks at me and it was simultaneously as if time hadn’t past while there were also apparent timely differences. Both of us now sported stubble, mine being closer to a beard. Yet, he still had that stupid plush dice dangling from his windshield. We chatted. I don’t remember about what. It was small talk, but I do remember there was a moment when he said something along the lines of “maybe you can’t do that, but you can give a good wedgie”. I remember how my hard on never subsided while sitting in his car. It’s funny what remains of your memories over time.

Chase pulls into the garage of his house. I had never been here before. He gets out of the car and nonchalantly enters his home, knowing I’d follow. There was a black lab that excitedly greeted me. I followed Chase into his room, and he closed the door behind him.

Chase’s room was the standard expected room of a teenager. Sports posters on the wall. His bass on a stand in the corner. A pile of clothes scattered on the floor. Chase noticed me looking at the pile.

“Find any underwear in there?” Chase asked.

“A couple” I reply.

Chase walks up to the front of his bed, taking off his grey zip-up and then tossing it on the ground. He stares at me a for a second as I stare back at him. He’s wearing a slim fitted light grey t-shirt and jeans. Chase then turns around, his back now facing me. I remember feeling awkward standing in that silence. Like I didn’t know how to fill it. We used to have so much to talk about. There were still things that should be said. Yet, I remained silent, lost in where to start.

“Do it” Chase said quietly. Almost as if through an exhale of breath.

His words snapped me out of my haze as if we were in high school flirting in our distant way. Our words and jokes that were just between us. Because no one, not even each other could ever know our true desire for the other. Except, we weren’t in high school anymore, and both of us since then had come out to our close friends, but more importantly to ourselves. That layer of shame was no longer relevant nor present. Nothing was stopping me.

“Do what?” I teasingly ask, taking a couple steps closer to him.

“Give me a wedgie. Please” and then he said my name. I don’t know why, but I found that hot. I was now directly behind him. It was again as if time hadn’t passed. Like I’d done plenty of times before, I lifted his shirt and fingered my way through the waistband of his jeans which also donned a brown leather belt. Once my fingers obstructively found the underwear, I made the waistband of them visible with a gentle tug. The underwear’s black waistband donned the word Hanes stitched multiple times in skinny white letters. The fabric underneath the waistband was dark grey.

I looked forward and clocked my own eyes in the reflection of the full body mirror to the right of Chase’s nightstand. I then locked eyes with Chase who was also staring at me through the mirror. It was like old times. I sharply tugged on the Hanes waistband and Chase arched his head and groaned as simultaneously the leg holes of the underwear came in full display above his jean’s waistband. That was new.

“I was curious” Chase said smirking slightly at me as I had him up on toes as held his underwear up in my grasp. Then I lift upward on my toes almost lifting Chase off the ground by his light grey briefs. My cock is at full attention now, obviously visible through the front of my black joggers. As I continue tugging at Chase’s underwear, on the occasion tug the bulge would briefly drag or rest on Chase’s ass. He knew where I was at.

I continue tugging, alternating between slow gradual pulls and quick pulsating tugs. On each pull, Chase varied his sound responses. Some were groans, quick exhales, and my personal favorite the occasional “ooh” or “ahh”. I got the grey briefs all the way up to his neck at the highest but I would then mess around with this wedgie by snapping the briefs against his back multiple times. I would also tug while pushing him forward only then to pull him back towards me, inching the underwear further in his butt. I at this point have never wedgied Chase in briefs. This made it exciting and new in a way I couldn’t begin to explain at the time, but thinking back on it I was likely excited by the arousal of it all.

The grey briefs were bunched, leg holes and all were above his jeans. I reach my hands in front of Chase, gently moving my hands towards his belt buckle. I slowly start navigating the belt buckle loose and I unbutton his jeans. I then abruptly pants Chase, leaving his wedgied ass full on display. Chase turns his head back towards me, smirking.

“Having fun?” He asks as he slowly pulls his briefs out of his ass and back into place.

I then lifted Chase toward me by his hips, so that his neck was right up against my face. I kiss his neck. Chase moans. I kiss his neck again, but this time as Chase moans I kiss him on the lips. Our first kiss. This right here was all I had ever wanted. His lips on mine.  He didn’t pull away. He turned around wrapping his arms around my shoulder as we continued kissing. His tongue quickly made its way into my mouth, and mine in his. I don’t remember gripping his waistband as we continued kissing, but when I opened my eyes for the first time as Chase was kissing my neck, I saw myself through Chase’s mirror, with his grey briefs lodged up his ass so hard that besides the fabric in my grasp there was no indication Chase was even wearing underwear. It was lodged that far up his perfect round ass. I tugged again sharply with my right hand while my left hand pulled Chase’s head back by his hair.

For a moment, we both simply stared at each other. No longer seeing the scared kids we were years before, but instead seeing ourselves as the men that we are. Men that are kind, yet long for another man’s attention, lust, maybe even love. Yet, in that moment we just remained present. In our own kinky way.

The kissing and the wedgies continued. I even let him briefly tug my blue Jockey boxer briefs softly up my butt, but he remained eager for his flossing. The only thing keeping me from ripping his briefs clean off him was the continued kissing, it was proving to be a weakness of mine. Over the next couple of minutes, Chase kissed his way down my body. From my lips to my neck, to my nipples, and further down my stomach. Chase was on his knees now, alternating between looking at my throbbing bulge and up at me. He looked so beautiful looking up at me, as if I could solve all his life’s problems. Chase slowly then lowered my black joggers off me while still looking at me. Pre cum was already staining the front of my blue boxer briefs as Chase lowered those too. This wasn’t his first time seeing my cock. Back in our high school days we dared each other to hold the others cock in the car for a minute. But this was certainly different. Especially because this time Chase was licking the pre cum off the tip of my cock before putting the rest of it in his mouth.

I audibly moaned as my cock was blown for the first time, overwhelmed by the sensation of it. The newness of it. The excitement of it. All of it felt like a lock was finally clicking open. My whole body recoiled when Chase took a moment to merely tickle my cock with small kisses. He’d told me he was hooking up quite a lot in college in the text exchanges we shared when we chatted briefly after he came out. Back when I was still so scared to accept that part of myself. Before I ghosted him.

“I always thought that you had a hot cock” Chase said looking at me.

I looked down at him, feeling aristocratic as I noticed his grey briefs still lodged up his ass. Chase went back at my cock again; except this time, I cupped the back of his head with my left hand, gently pushing his head inward so my entire cock could face fuck its way down his throat. My other hand between thrusts reached down Chase’s back to grip the grey briefs. As I alternated between thrusting my body forward and pulling on the underwear, I felt closer to myself. As if I was about to descend on the first drop on a roller coaster. I felt drops of sweat trickle off my chin. I looked down then, only seeing Chase’s brown hair and his briefs gripped in my hand halfway up his back, lodged up his ass.

It was then when I remembered the time he yelled at me after we got caught by a police officer. We were rubbing each other’s cocks in an empty parking lot with sunshades over the window of Chase’s car. How scared we both were. How we reacted differently. And then, how when I was a Junior in high school when I saw he had posted a picture on Instagram with a guy. A boyfriend. How betrayed I felt. How exposed that post made me feel. But also, how lonely it made him feel as well.

I gently let go of Chase’s briefs and removed myself from his mouth, pretending like I heard my phone vibrate. I made up something about my mom wondering where I was and that she needed me home. Chase understood, we dressed, and he drove me home. When we got back to my house, there were no other cars in the driveway.

“She wanted me to be ready to go by 4”. I said, trying to talk my way out of the lie.

Chase seemed like he understood, but I must give him more credit. It’s possible that Chase knew I was lying. Still, before I could get out of the car he stopped me. Gently his hand clasped into mine. Again, something new. He leaned in and he kissed me gently. For a moment, I succumbed to it. The desire and lust I still very much had from the past hour’s activities. Tongues touched. He still grasped my hand. And then as if I teleported, I was locking my front door, and he was driving away.

I was just trying to read 🤓