Dreaming of Leather men

by StrykerJ

22 Jun 2021 1786 readers Score 9.7 (26 votes) PDF Mobi ePub Txt


Introduction
Benson Long found out that the love of his life had been living right next door all that time. The Ebony jock, Theo Cummingham, had been bullying Benson all through his childhood. But Theo secretly just did that to be near Benson. After his confession, the boys decided to give their love-hate relationship a try.
This is an 8 part series describing the fun Benny had discovering his preferences.


A bully, a friend, and a lover.

Mary - one of Theo's little stepsisters - bumped into me when I nervously walked upstairs to Theo's room. She looked up in surprise at the leather-wearing tough guy she had run into.
"Sorry, Mary... Are you okay?" I asked of Theo's little sister.
"Oh... Hello... Benson... What are you doing here?" she asked, surprised.
"I will have dinner with you later, Mary... If that's okay with you, of course?" I smiled down at the little girl.
"Yes!..." She giggled and ran upstairs to the attic, where she slept with her two sisters. I had babysat the triplets a few times. So I knew them quite well.

But suddenly, it struck me as a little weird. I was going to make out with their 19-year-old big brother in their home. It made me very apprehensive. So much so that I had to pause and think before knocking on Theo's door.
"Just go in there... Treat him as if you have been lovers for years now!... It will be fine... Big-T will be just as nervous as you are... Go on, you got this, stud!" said my manly inner voice convincingly to me.

I took a deep breath and puffed up. I zipped up my thick leather biker jacket halfway and adjusted the stiffening package in my stonewashed jeans. Ready for a nice dinner and a hot show afterward. Then, knocking on Theo's bedroom door, I entered unannounced. Perhaps I tapped the door a little weaker than I should have done.
"Go away... Mary, let me be!" shouted Theo meanly from his room. I smiled to myself and opened the bedroom door anyway. "I said... go away, Mary!" called Theo. With his back still turned toward the door. Not knowing it was me who entered his room.

I slammed the door shut behind me and grasped Theo around his back. One arm over his shoulder, the other around his waist. Pressing his naked torso tightly against my classic biker jacket. Then, laying my chin on his other shoulder, I looked Theo deeply into his eyes. I said teasingly, "Hi... my name is Benny, not Mary... And you are?..." Theo grinned at me. I asked, "Have the triplets been bothering you again, big boy?... You do know they only want you to play with them, don't you?... You're their hero... So act like one, Jeez!"
"Oh shit... I had not expected you yet... I am still getting dressed... Sorry, man,... Dang, dude, you look ready to play!" replied the stunned Theo in pleasure.

"You're right, Big-T... Tonight, you and I will play instead." I softly joked. Cupping my hand over his black nuts in the cool leather jeans he was wearing. Theo sighed longingly and laid his head back onto my shoulder. Closing his eyes in utter pleasure. After a moment or two of sheer bliss, Theo grasped my fondling hand in his. Guiding it up and down his cock-bulge. Whisperingly moaning, "Oh Gawd... mmm... I have been dreaming about this moment all day, Benny!... I was scared stiff, not knowing how to start this... Oh fuck, boy... Hold me tight... Shit, man, I do like this!" Theo trembled a bit in my arms. So I held him even tighter. Our leathers creaked as I squeezed Theo close, pressing him hard against my chest. My stroking hand found his pierced nipple. I rolled it softly between thumb and forefinger. Making Theo cringe in pleasure a little.

I spun Big-T around and kissed the poor fool. Apparently, Theo was just as hungry as I was. Right then and there, we literally started to eat each other's lips. Moaning and panting, Theo had taken hold of my face. And I hung onto his sexy leather-clad ass. Grinding our bulges together. He was obviously figuring out what to wear for our date when I had walked into the bedroom. He had not gotten far yet. Big-T had only put on a sexy leather pair of jeans. He had been figuring out what to put on next.

Once we reluctantly broke apart, Theo looked me up and down in total astonishment at what I was wearing. He let his eyes glide from the sexy silver earring in my right ear and my butch back-to-front baseball cap with its leather flap. Down over my heavy leather biker jacket and my stonewashed jeans with a black metal studded belt. Al the way to the pointy black cowboy boots. Theo was utterly amazed. He had never seen me look this macho, with a matching cool attitude to boot. Big-T's eyes nearly rolled onto the floor, with his mouth gaping wide open.

"Like what you see, boi?... Tonight, I am gonna whoop your ass for a change, bitch!... Mr.B is in the house!" I gleefully called.
"Jesus, man," panted Theo hotly, "Those fuck'n boots!... God, you look so cool in those, Benny!"
"I am glad you approve, stud... I will kick your nuts with these if you don't do as I say!" I joked. Wiggling the toe of one of the black pointy cowboy boots in his direction.
"Ha, I bet you do, master!" laughed Theo naughtily.
"Just call me Benny, you fool!... I may look the part... But tonight, I hope we can take it nice and slow, Theo... You're not quite my first... but still... I've got a lot to learn." I sighed as we hugged and kissed again.

After a while of intense tonsil hockey, Theo asked me to help pick out what to wear over the leather jeans. Apparently, my wish for a leather-look had thrown him off. Thinking he should go for his toughest look. But having some issues getting it right. I looked at half the content of his closet spread out on his double bed. "Hmmm... You want to go extreme or understated?..." I asked him. Theo looked shruggingly at me. I had never seen Big-T this indecisive before. I picked up an ochre yellow hoody and a nice bodybuild shirt. I handed them to Theo, and he sat on the bed to put on a pair of butch biker boots. He completed the look with his gold bling from the jewelry box on his bedside table.

I pulled him off the bed and looked Theo up and down.
"Fuck, that is a cool look, stud... But I would tone it down a notch... Put on your black Nike high-tops instead... We don't want your sisters to get the wrong impression about their big bro... Now, do we?" I said, nearly drooling over this hot fucker's look. If I did not know better, I would say he was dressed to go on a gangbanging cruise with his mates.

Theo quickly put the rest of his clothes away. Giving me the time to look around his bachelor pad. Not a single poster of a scantily clad woman in sight. Something that I had half expected to find in his room. Instead, some cool big-bikes and extreme bodybuilders adorned his bedroom walls. It was a proper jocks room. I tentatively asked Theo, "So... Ummm?... T... How would you describe yourself?... I mean... are you straight, bi, curious, or plain gay?" Theo turned around at me and thought about it for a moment. "You don't have to answer if it makes you uncomfortable... Sorry that I even asked," I said, instantly regretting my forward question.
"Oh no, it's not that... No problem, in fact... But I just never thought of it like that, bro... I think... Well, maybe 15% straight, 25% bi, and 60% gay, I guess..." he tentatively answered, "But tonight... Tonight I am all yours!... Leathers and all!"

I unzipped my leather jacket and hung it over Theo's coat. Placing my hands on Theo's shoulders while he grabbed me in close with his hands around my waist. Theo looked at me and tilted his head. He sighed deeply and said, "Tonight is gonna be great, Benny... I think... well... Ummm... I think I may be in love with you, Ben," whispered Theo softly, "And I am not just saying that either... Oh Gawd... All those times I kicked your ass... I... Ummm... I just wanted to be close to you, buddy... I am so sorry, man!... I truly am... I was horrible to you all these years," confessed Theo. Looking pretty weak and uncomfortable at me. Not at all like the butch alpha gang leader he normally portrayed.

It was true, though. Theo and I grew up together, living next door from each other. Our parents got along very well. But, unfortunately, the same could not be said for Theo and me. Ever since Theo discovered he could force others to his will, I was the center point of his attention. He bullied me all throughout my teens. Making good use of my insecurities and weak appearance. And when he started to gather a posse around him, things got even unfriendlier for me. They regularly kicked my butt. Theo Cummingham was the worst of them. But, now that I knew he just wanted to be near me, it somehow all made sense. He did like to hold me tight, while his boys did a number on me. But when they went too far, Theo always stopped them. Heck, the few times the gang threatened to sexually abuse me, Theo made sure I wasn't harmed. Well, not too bad anyway. I just wished he hadn't waited to confess his desires until tonight.

"It's okay, Big-T... Tonight, I am gonna whip your ass raw anyway... fucker!" I joked. Still, his confession had me a little stunned. Theo shuddered when he saw the dirty glint in my eye. This was probably the first time he had seen that little hint of a budding butch bully in my new attitude. And Theo was visibly enjoying that.

Aunty Jesmin called up, "Dinner is ready!... Go wash your hand's Girls!"

I grinningly looked at Theo. We both ran for the bedroom door. Pushing and shoving our way through it into the upstairs hallway. Giggling like little schoolboys. Not wanting to give the other the right of way. In the kitchen, I walked over to the sink to wash my hands as well. Helping the triplets, Mary, Lily, and Zoey, to dry off afterward. Silently motioning to Theo to set a good example for his sisters by also washing his hands. This earned me a broad smile from Jesmin. I could see her thinking that I would be just the right guy for her firstborn. Somehow she had always known her boy was gay. But Jesmin had been unable to make Theo stop and smell the roses.

Dinner was pretty uneventful but extremely nice. Aunty Jesmin had made us a real feast meal. I entertained the girls a bit with some silly jokes and stories. This was as much for their enjoyment as to show Theo how easy it was to engage with his little stepsisters. After dinner, the girls wanted to hear me play their father's guitar again. I looked over at Jesmin, and she nodded, agreeing. So we went into the living room, where Theo and I played them a few tunes. Theo had run upstairs and got his bass guitar. The girls sang along with all the popular songs until it was their bedtime. Jesmin brought the triplets upstairs. Theo took me back up to his room as well. I got the sense that Big-T would have happily skipped dinner and screwed my brains out when I arrived at the Cummingham's. But that's how things go sometimes. You need to wine and dine your date before you get to the one thing you have been hoping for all day.

In the hallway, Theo had grabbed my hand and pulled me inside his bedroom. He fumbled with the lock on his door, thinking we would get some privacy at last. It was obvious that Theo was a little nervous too. So I asked if he had some tunes that we could listen to while we got comfortable. That put his mind on a different track and helped him to relax. There was nothing left of the butch, tough-guy attitude I was so used to. Theo scrolled through his playlists as I suggested something slow with a nice beat. Then, a sweet and rhythmic Bob Marley tune started to play from his sound system.

I tapped Theo Cummingham on his shoulder, and he looked up at me in surprise. Laying a tender hand on his cheek, I softly turned him around and kissed the ebony stud. We got into a groove and started kissing to the beat of the song. Rocking back and forth to the music. Dancing in the middle of the bedroom. With me rubbing my fingers through his short dreadlock mullet with shaved-up sides. Theo had laid his hand on my love handles and pulled me in closer. God, this hunk looked so delicious. He was a great kisser, and Theo smelled good too. While we snuggled a bit, I pulled the ochre yellow hoodie up over his head. Exposing the gorgeous ebony biceps on Theo's arms. I kissed and worshiped the huge guns. He was a really well-trained jock. And since he loved to show off, he flexed his biceps for me. He wasn't a bodybuilder as such. But big and muscular nonetheless. Theo had more of a swimmer's build. Big pecs and a tight, well-defined sixpack.

After he had lost the hoodie, I nearly ripped off his workout shirt as well. Exposing more of the goodies. His nipples were pretty big and hard. Eager as he was, Theo wanted to get into my pants too. But I hit his fumbling hands away. I wore a surprise for him under my faded stonewashed jeans that I did not want him to see just yet. Instead, I started to take off my black polo shirt. The shirt had a small logo of the leather shop I had been to last Thursday. Theo grinned dirty as he recognized it. His hand stroked my - nearly none existent - pec. Big-T got excited nonetheless. He felt the leather chest harness I was wearing underneath the tight polo. Theo shuddered as his fingers followed the strap over my torso. Excitedly, he helped me pull the polo off over my head. Exposing my naked chest to him.

A little embarrassed for my lack of muscular physique, I said, "Don't look so surprised, boi... I only wear this as compensation for my lack of strength, and for utter love of leather." I had grabbed my leather biker jacket and swung it over my shoulders again.
"Oh fuck... Will you look at that... You don't need it, Benny... You'll make up for that with your attitude alone!... I'll happily submit to you, master!" said Theo looking submissively up at me.
"I am looking for a little bit more than that, Theo... And tonight, I really would like to be your bottom..." I sighed as I said it.

"Oh... but... huh, what?... I thought you were a..."stuttered Theo, "... After what you did yesterday, you had me convinced that you prefer to take full control, sir?"
"T... I would probably agree with you... But I have only been fucked once before... So I'd love it if we could take it in turn... perhaps?" I asked a little shyly.
"Who was the guy that made out with you?... I'll kick his balls... It wasn't that Jeff Skyler, was it?" announced Theo, a little annoyed.
"Nope!... This guy would probably nail you to a tree and use your bullying nuts for target practice, though, if you keep talking about him that way," I said laughingly. "It's Mark's man... Lt. Philip Parks!... And he did me on my request... Just so I could feel what it would be like... But fuck, that dude is huge, man!... 9.5 inches and as thick as a baseball bat... The length I can deal with, it's his girth that got me worried... But it worked out fine in the end." I answered to a red-eared Theo. His eyes were wide in amazement at my openness.

"So... Ummm... Theo... I think I can handle your dick... Just go slow on me at first, though... I'd like to enjoy this too... " I said as I looked hornily into Theo's eyes. "... As soon as you have loosened me up, you can do whatever you like with me..." I said clearly. "Theo, I know you got plenty of experience in rough bedroom workouts... Ha!... You keep me awake once or twice a week... Banging your girls and boys as if you are trying to nail them onto the wall beside me..." I joked, "...Dude, you really need to move your headboard away from the wall... Or someday, you end up in my bedroom!" Theo and I laughed so very hard. We ended up sitting on his bed, where Theo took off his sneakers. Throwing them haphazardly halfway across his room.

Big-T wore nothing but his leather jeans now. And Shit, even watching Theo in nothing but his jeans and naked torso could excite me enough to cream my pants at this point. So I laid my hands on his thighs and started to lick the leather crotch.
"Oh... Ah... So nice, bro... Yeah, lick that bulge, dude... Shit, this is so hot... I have never felt this before... Oh fuck... Arghhh... O! stop!... I am about to... Oh, Shit... Arghhh... God, fuck!" screamed Theo. My tongue tease had him cumming inside his leathers in ecstasy. I unbuckled his belt and unfastened the buttons. Opened the leather pants up and proceeded to eagerly lick his spilled man juice off his tight chest. Taking the still rock-hard and twitching member into my mouth, sucking the last remanence out of the gorgeous ebony drinking straw.

However, when I looked up at Theo, I realized that he was utterly embarrassed by the premature ejaculation. I didn't mind, though. It tasted nice, and I knew Theo was just a little too excited. So I merely smiled up at him and went deeper down over his 9-inch throbbing member. Never losing sight of Theo's eyes. After a few minutes of this, Theo got his courage back and started to smile again, stroking my hair. Making me bob my mouth a lot faster over his black cock. Eventually, I took all of it down my throat one time. And held my nose pressed tight to his abs.

"Oh god... Yeah, man... That's how it's done!... Cock-sucker!... Take that big black bully's dick!" groaned Theo in delight. I slowly got up for air. Making sure I let my tongue stroke the underside of Theo's shaft as if I was eating his slong.
Once I had released his tool, I looked squintingly up at him. Got up from the bed and put Theo on his knees in front of me. "Clean my boots, boi!..." I bruskly commanded. Theo bent down and instantly licked both the cowboy boots without question. Sucking on each of the pointy toes in turn. It gave me an odd but powerful feeling, watching Theo worship the cowboy ankle boots as if he was licking my dick. He looked just as I must have done for Jeff Skyler at the gym last Wednesday. "...Fuck... it's only been 4 days since I was introduced to gay leather sex by him..." I suddenly realized.

I placed one of the boots meanly onto Theo's back while he licked the other. Unzipping that boot. Doing the same with the other one a few moments later.
"Take my boots off, boi..." I commanded, "... and don't you dare throw them around!"
Theo obliged. Looking longingly at these pointy cowboy boots now that he held them up close.
"Take off my socks too, bitch!..." I instructed Theo, "... Put them inside the boots!... And place them neatly under your bed, boi... That's a good kid... I'll teach you to keep your place clean and help your mom around the house, yet!" I said, laughing meanly. He must have taken the hint. Because he also put his sneakers away next to my boots.

"Put that cool leather jacket of your's on T... and then come stand in front of me," I suggested calmly. "I'd like to see you in all your leathers, Theo!" Theo put the gypsy biker jacket over his shoulders and stood promptly across from me. "One last thing for you to do... Theo... Remove my jeans!... I got an extra surprise for you."
Excited, Theo tried to kiss me. But I rebuffed his advances. So he unbuckled my butch belt and unzipped the faded stonewashed jeans. They dropped to the floor together with Theo's mouth. I was wearing my chaps underneath the jeans. My dick sprung free with Jeff Skyler's metal-studded cockstrap neatly fastened around my 7.5-inch cock and balls.

"Well, don't just stand there, Theo... It won't bite!... Suck me off and play with my ass!... These leathers aren't putting you off, is it, boi?... It can't be!... Look, your dick is starting to leak again!" I commented. Theo did not have to think twice. He seemed sort of glad I took control. Not that he had much choice. Because I had pressed him way too hard to his knees again. Theo kissed my cockhead. With his big round eyes fixed firmly onto my gaze. My dirty grin was meeting his halfway. I nodded as Theo started to stroke my chaps, and he sucked my cock hard and deep. The tongue of this ebony leather god was doing things to me that made standing upright hard to do. So I held on to the only support available. Theo's bobbing face. After a few minutes, I skull fucked the dude. Rudely forcing myself into his mouth and down his throat. Apparently, Theo had some experience with that. The stallion had no gag reflex to speak off. He just took it down and enjoyed himself.

The only time he stopped sucking was to wet a few of his fingers. Driving them ever deeper past my sphincter into my ass. Playing with my prostate as he did so. After minutes I stepped away and laid down on my back on Theo's bed. My leather-clad legs spread apart so my lover could take my nearly virgin hole. Theo took off his leather jeans and sat between my legs. Now only wearing his leather coat.

"Do you want me to use a rubber?" he asked with a hint of disgust on his face. Hoping I would let him screw me raw.
"Dude, T?... I do leather... I don't do rubber!" I joked with a serious undertone. "Take it nice and slow though, big guy... use some lube, if you got it."
Theo took a big bottle of lube out the bedside table and shot some over his index- and middle finger. He gently smeared some over my rose butt. Finger fucking my slicked up asshole a while. Sucking and kissing every part of my lower body that his lips could reach. Before drizzling a stream of lube over his big black cock. He sat on his knees between my raised up legs. Stroking his slicked-up dick. Preparing it to push past my sphincter into my asshole.

"Okay... Here goes nothing..." gasped Theo nervously to himself.
I just laughed nervously and said, "Ha... You call that black walnut tree trunk nothing?... Just be careful... will you!... If you hurt me, I will hurt you worse!... If you please me, I will please you better!" I smiled at Theo as he penetrated my boy-cunt carefully. Big-T took his sweet time. Making slow but deliberate movements with his 9-inch ebony dick. I cringed a bit at some point. Causing Theo to stop. I grasped Theo's buttocks and pushed myself over my lover's hot cock.

"Go on, T... you're inside me now... Fuck me, dude... I am loving it... Take me... I am yours, boi!... Nail me to the wall, dude!" I smirked hotly, egging my lover on. Still sitting on his knees between my leather chapped legs, Theo started to ride my ass with long steady strokes. Timed with the music on his stereo. After a few minutes, the song changed to a much faster one. Theo laughed and plowed my hole with short mean thrusts. Slow going out, but super rough and deep-going in. I grabbed Theo by his leather jacket and pulled him onto my chest. Lifting my ass in the air as we repositioned. He was taking me like a rampant rabbit. Oh God, did he fuck me nice now! But by far, not as hard as I had hoped or expected of him. This bully was clearly holding back on me.

"Theo... what the fuck is going on, dude?... You screw me as if you fear that my balls would crack like eggshells..." I questioned him angrily, "... Where is that bully that takes without asking permission?... Dude, you got my permission... Now... Take me already... So far, you score no more than 4 or 5 out of 10, boi... You can do better than that!... I know you can!"

Theo stopped all movements. With his manhood still deep inside me, I felt, rather than heard, Theo cry on my shoulder. I put a hand on the back of his head. We lay there for a few minutes before Theo said sobbingly, "Benson... I can't... I don't want to hurt the one guy that I truly love... Benson... Do you want to be my boyfriend?"

I smiled and twisted my head to kiss Theo's cheek. "Two things, buddy... I'll let you know if you actually hurt me... And if you take this up a few notches, then we can talk again afterward... Agreed, bud?... I am definitely not ruling anything out at this point... Fuck, you don't want to know how frequently I've dreamed about us, Theo... More often than not, you kicked my ass hard, and we ended up together anyway in those leather dreams... And so far, most of my dreams have come true... I want you to beat up my ass with that big stick of yours and fuckin' breed me!"

"Really?... You want me to come inside you?..." sighed Theo gasped, finally regaining some of his composure.
"If you can take me to level 8 or 9, I would even consider making you my man!... After that, we can get a little rougher... Not every week, though... But tonight, you may go for it... Just remember I give as good as I get!... How about it?... Want to bully my ass into submission one last time, Big-T?" Well, after that, Theo got back into his rhythm. He slammed his nuts against my ass like wracking balls. Theo got his big bully gang-banging attitude back and then some. Taking my tormented asshole all the way up to level 9.

"Oh God, Benny... I am about to cum!... Oh... Fuck your so tight... I love you, Benson... Take my nut, man... Ah... Oh... Arghhh... Take that Shit... Here it comes... Oh... Fuck... Oh Shit!... mmm... Arghhhhhh... Oh, damn, man!... Take it, boy... Take that load..." screamed Theo, blasting his nut strongly up my gut. I felt the hot jizz fill me up. Theo just kept on pumping it deep inside, hammering the man-milk into a thick cream. I was unable to speak anymore. All I could do was to breathe in time with his rough ass pounding. My eyes rolled into my head. My hands were hanging onto either side of the mattress. And I was loving the way he bullied my ass.

Someone coughed from Theo's bedroom door. "Benson?... Is he hurting you?" asked a familiar voice. I looked around Theo's brought shoulder and saw Theo's stepdad standing there with a concerned look on his face.
"Oh... Hi... Mr.T... how was work?... No, Theo is the perfect lover, sir... you can be very proud of him," I replied proudly with a dirty wink and an ass full of ebony dick.
"I take it you like his cock then?" laughed Tylor watching his boy screwing my ass.
"No, sir... I am LOVING it!... Not as much as I am going to enjoy his black hole later, though!... I am going to make him see stars before I am done with him!" I said grinningly.
"Ha... You do that, boy... Enjoy guys... You look made for each other!" laughed Theo's stepdad as he closed the bedroom door behind him.

Much later, I said, "Shit, Theo... You got a nice ass, man." I sighed as I laid my head on his chest after a solid hour of screwing his brains out.
"Jeez, man, Benson?... I did not know you could come that often in one evening," panted Theo amazed at my stamina.
"Ha... Well, don't expect me to do the same tomorrow... Give me a few days, dude," I joked. "Theodorus Mauritius Cummingham, if you want to be my boyfriend... Then you better put a ring on it, dude," I said as I lovingly looked up at him.

With his eyes full of amazement, he gasped and said, "Oh Gawd... Yes!... I would love that, Benson Long!... Oh, you don't know how happy this makes me, Boo!" He rummaged through his small jewelry box on his bedside table. Theo pulled out a black and silver signet ring with his TMC monogram. Sliding it proudly onto my finger.
"Awe, thanks... That's beautiful, buddy... it even fits with my earring," I said elatedly. I looked beamingly up at my new boyfriend.

"I got something for you too, stud," I said proudly. Taking 2 leather braided friendship bracelets out of the inside pocket of my leather jacket. I handed them to Theo. One had a black metal strip reading Brains, the other read Brawns in silver lettering. Theo looked at them and grinned. He handed me the Brawns bracelet back and held out his right arm for me to put it on him. I took the Brains bracelet and made Theo fasten it on my left arm. Then, we happily fell back onto Theo's bed. We lay on our sides, facing each other with grins from ear to ear. Even after this first time, we felt deeply in love. We both had gained a much deeper understanding of the needs and wants of the other.

"Happy?..." asked Theo after a while.
"Very... and you?... Was it something worth repeating?" I asked in reply.
"Oh honey... I'll do you anytime, anywhere, in any way you want it!" sighed Theo as he kissed me longingly. Asking me, "... As long as you tell me where you got those boots from!... I need me some of those, dude."
"Ah... You may need an additional paper route... Boots like these are really expensive... But if we get the chance, I'd like to take you shopping for some kinky Sendra cowboy boots... You know what... Put your leather jeans back on and try them on for looks, stud!... I want a cool picture of you for my phone anyway," I said happily.

Theo eagerly obliged. Posing in his leather jeans, his halter top, and my pointy cowboy boots. A few pictures, actually. Every photo saucier than the last. On the last one, Theo had his leather jeans seductively open, with his 9-inch cock in hand and a mean - don't fuck with me look - on his face. I downloaded the results to Theo's laptop. As he stood behind me, I grasped the lovely black tree trunk. Guiding it to my leather-clad ass. In no time, Theo had grabbed onto the back of my chaps and was hammering me raw from behind again. I handed him my phone and told him to video us. Instructing my lover to talk real dirty to me, as if he was manhandling some kid from next door. The way he used my ass took me all the way to level 10 in a few minutes. Theo came hard too. Splattering his jizz all over my ass and back. Railing my tormented ass, shooting some more up my hole.

Theo and I panted hard after this session. He held me tight, sighing, "Benny... I love you!... I even see now what you meant about the leathers making you horny as shit, dude... They do give a certain edge."
"Right... But you won't ever catch me wearing this much in public, though... I'll just combine some with some regular stuff... That's enough kink for me, stud," I breathed heavily to Theo Cummingham. "Anyway... Thanks for a lovely evening, Big-T... I need to go home and see what that dickhead of a brother of mine is up to." I kissed my man and got dressed. Theo went for a quick shower, and I quietly tried to sneak out the Cumminghams' back door.

However, I bumped into Theo's Stepdad as I walked into their kitchen. "Wow, you two have been busy..." joked Tylor looking at the clock as I walked into the kitchen with my boots in hand. It was well past midnight now. "Did you enjoy yourself, Benson?"
"Yes, sir... That I did... Theo even put a ring on it... Look..." I said as I happily showed his stepdad Theo's signet ring.
"Cool!... You'll make a fine man out of my boy, yet!... Congratulations, Ummm... son, I guess." The bi-sexual Tylor Cummingham grinned, got up, walked over to me, and kissed me full on the lips. I could not resist. I copped a feel of his 13-inch Jamaican slong. It immediately reacted to my touch.

"Gosh, sir... I do hope I get a chance to play with that monster anaconda too sometime!" I sighed longingly.
"Well, take it out and suck on it if you want, son... I don't mind," grunted Tylor darkly, "... Why should Theo have all the fun, aye?"
"Ha... maybe some other time, sir... Why don't you put a bin liner on that thing and give aunty Jesmin a run for her money,"I said jokingly. Whishing Theo's stepdad a goodnight after putting on my boots and walking out the door. Floating out would probably be a better word. I was still high on adrenalin and lust.

However, the scene that awaited me as I walked into our kitchen was somewhat unexpected, to say the least. Mark and Philly played strip poker with Jimmy and Charles, whom I had met at the gym yesterday. Anyone who walked down the back street could have seen the half-naked army hunks fooling around together. Clearly, Jimmy was on a losing streak. And Charles wasn't doing much better either. He only had his army shirt and cap left on. Jimmy had been ordered to his knees and gave the gorgeous army captain head. It did not really look like he was enjoying this very much. One, because Charles was too big to be allowed. And Two, because the position Jimmy was in seemed pretty painful on the knees. The fact that Mark had his army boots pressed against Jimmy's ass wasn't helping very much either. Mark was pumping the redheaded soldier over Charles's black monster rod from behind.

Then - watching me enter the kitchen in my full leather gear - he half-shouted at me, "Fuck'n hell, kid!..." The cigar-smoking captain exclaimed with a dirty grin on his face, "... What are you supposed to look like?... You do know that Halloween isn't for a few months yet, don't you, boy?..."
It was clearly a poor attempt at a joke at my leather getup. One that I took very unkindly to. Mark looked over his shoulder. He saw me walking in the back door, saying to me, "Oh... Hi Benny... How was the first date with Big-T?"

Still mad as shit about Charles's sneers, I ignored Mark and walked over to the sink for a glass of water. I dropped my sweaty leather jacket and the black polo shirt on one of the barstools and looked at the army foursome.
Calling over to Charles, "Screw you too... Bastard!..." I squinted dangerously at Charles, "... Do you really have to stink up the place with that cigar?... I have enough to worry about... Without having to air out the place before my parents come home... I expect them any moment now!" I said angrily, "... I want this kitchen spotless and aired out... And you lot need to clear out before dawn!... And... Give Jim some kneepads if you want to keep him down between your legs like that!... Otherways, you're no better than that Jeffy-poo!... Bloody army grunts!..." Still fuming at Charles's remark, I said, "... I have enough on my plate... I need to find a way to tell my parents that I am gay... have a cross bike... a boyfriend... and no longer take judo classes!... I don't want to have to explain why their home stinks of cigar smoke too!"

Mark's ears perked up at my boyfriend remark. He shot out of his chair like a tracer bullet. He flung his big brotherly arms around me and squeezed me tight. "Oh, Congratulations, Benson!... Buddy, you really don't like wasting time, do you?... Last week you complained that Theo was a bully... And now you're boyfriends with him?... Well done, you!... I am so fucking proud of you, Benny... And don't you mind Capt. Charles 'Doc' Brown... He's a joker... But thanks for looking out for Private Jim 'Bulldog' Galway, buddy... Don't worry... We'll clean up after ourselves... Sorry, Benson."

I left the 4 army dudes and went upstairs to take a long hot shower. Cleaning my asshole in the process. Man, I feel so pleased with myself, but oh so fucking filthy. My sphincter still felt stretched open. Having muscle pains in places, I did not know I even had muscles. Theo had taken my nearly virgin ass and used it properly. It had taken him a while to get going. But once he was on a roll, I just took all the punches as they came. Loving every second to the fullest extent. And even after we flipped, I enjoyed dominating the stallion's black hole as well. I did make him see stars. He told me so, over and over and over again. Instructing me on how to nail his ebony hide to the wall. I gave Theo as good as I had taken it from him.

After I was out of earshot, Mark had explained to Charles and Jimmy that the sooner they learn to treat me as equals, the easier it will be for them to understand me. Philip told them that I hated to be called a kid or boy. Not because I was their age, but because I was much more mature than my baby-face would have them believe. Mark had to explain to his gay army friends my thing for tough guys and leather. And that made Charles see the error of his quip.

The next morning - after a restless night's sleep - I ran into Doc in the bathroom. With rings around my eyes and a little bow-legged, I stumbled sleep drunk into the shower. Charles was butt-naked, and his pierced cock was happily bobbing up and down while he shaved. The heavy Prince Albert was clinking against the sink. Man, this gorgeous black - all American - army hunk was really well built and hung like a horse. At least 10-inches, reasonably thick, with a beautiful massive cockhead. The pierced cockhead made him look fervent.

"Hi, Benson... Sorry about last night, dude... We have gotten off to a rough start, haven't we?"
I sort of ignored him. Stepping out of my sweat shorts to take a piss. He happily watched my stark naked ass in the mirror as I took a leak. While the army captain kept on shaving his face and pecs. When I turned back to him, I saw that he had a little issue shaving around his big nipples.
"Here... Let me help you with that..." I said as I took the razor from him. I proceeded to give his chest a clean shave. His semi-hard cock hit mine a few times. Arousing my little man too. After wiping the last shaving cream away with a wet towel, I looked down at the captain's Prince Albert. I laid the impressive 10-pounder in my hand and stroked him softly. Fastly feeling it grow harder under my soft touch. I watched it grow as I started to stroke the big black cock. Looking interestedly at the man's pierced nob.

"Won't that make a mess when you piss, sir?" I asked Charles.
"Not as much as when I shoot a load!..." he joked.
"Why do the guys call you Doc?..." I asked, looking at the captain in his beautiful dark eyes. He explained to me that he was an army surgeon. Charles even had a general practice for civies as well in the hospital near the base. He actually wanted to have a little chat with me about that later. While he talked, I had dropped to my knees and sucked Doc off like a pro.
"Oh... God... Ah... Benny... Nice... Don't knock your teeth out, dude... Oh fuck, man... Yeah, suck that slong... Fuck, you're a great cock-sucker, Benson!"

I stroked and twisted the monster using two hands while bobbing my mouth fast up and down over it. Taking Charles as deep as the big PA-piercing would allow me to go. Moaning and grunting in absolute pleasure of this morning snack. The sounds I made turned the stunned captain on, "... Oh fuck... Stop, Benson... You're about to make me cum, boy!... Ah... Oh..."
I hotly looked up at the black stud, asking, "... Is there anyone else waiting for this load then, sir?..." I grinned up at him before continuing my morning workout on his dick.

"Ah... Shit, boy... No, there isn't... But... But... Oh, fuck it... Here it comes!... Stick out your tongue... I'll give you what you deserve!... Arghhh... Oh... Fuck... Arghhh... fuck... Fuck... FUCK!... Oh, Benny... Ah... So nice... Oh Gawd... Fuck, man." grunted the buff black army hunk. Stroking his nut out in heavy streams over my tongue and into my open mouth. My eyes locked on his. I swallowed it and slowly stood up. Charles hugged me as we kissed. I grinned hornily at him and said, "I guess now we have to take a shower together too... We've made a mess, dude... I think I better not drop the soap, though... That black pierced monster won't fit, I fear."

Charles took the cum-splattered piercing out. He pushed me under the shower. Doc placed my hands up against the wall and soaped up my back. But he did not stop there. He got my hole slick as well and slowly and very gently made the black rod disappear inside. The Doc screwed me while he soaped my entire body. Nailing me raw to the shower wall as we flushed the soap away.

"Shit, Doc... Do you treat all your patience this way?... If so, then I might consider changing doctors." I said grinningly, with a trembling voice. Feeling well used once again. A sensation that I was quickly getting addicted to.
"No, sir... Only the really hot ones that can handle a big black cock like a pro... And I can tell you, there are not many that can do what you just did, Benny... I'd be happy to take you on as one of my patients, sir..." said Charles Brown in awe to me.

While he road my ass, he explained that Mark told him I was looking to bulk-up my body. Telling me that he would happily give me some proper medical advice. Helping me set up a diet plan and even some physio or meds if I would change doctors. I thought about it and decided in a split second, "Sounds cool with me... But I think I would also need to get checked up for some ... Well... You know... Ummm... gay-related stuff... I am a little pig farmer that likes to play dirty if you catch my drift."

"Sure... I can certainly give you the once over, Benny... We can check if you're healthy and good to go," said Charles delighted.
"Well... You have already checked my temperature with that beautiful instrument... So, did I pass my physical, Doc?"
"With flying colors, Benny!..." he replied with a dirty grin as he spanked my butt.

"Shit..." I suddenly called out.
"What?..." said the Doc looking worried, pulling his cock a little too fast out of my asshole.
"That is one more thing I have to tell my parents about... I better start making a list... Let's put the ambulance on stand-by... Mom is going to have kittens if I tell her I changed doctors too!" I said half-jokingly.

After the unexpected bathroom adventure with Doc Brown, I dressed in some of my old clothes. Thinking I had a lot of housework to catch up on before my parents would come home. However, when I got downstairs, I noticed that the 4 army guys had already cleaned the kitchen and the entire ground floor. Everything was spick-and-span as my mom had come to expect of me. She worked long hours as a nurse. So most of the cleaning, cooking, and laundry were left up to me. "That gives you something to do since you don't have any friends," had my mom once told me. I did not mind the housework. But that hurtful comment I could certainly have done without. It had totally undermined my self-confidence.

Theo was loitering around his backyard. He watched me smirkingly as I stepped outside, intending to mow the lawns instead. Theo looked disappointedly at my old getup. Saying, "... Morning Boo!... What?... No leathers today, Benny?" he asked, surprised.
"Nope... Mom and dad are coming home tomorrow, I think... So I thought I'd better do some work around the house... This old shit will do for that... At least I don't have to worry about getting these dirty anymore," I laughed as I stood next to Big T, leaning over the fence.

"How did you sleep, Boo?" Theo asked.
"Ha... I've had better nights... I do like you calling me Boo, though, stud..." I said with a warm smile.
"I don't mind you calling me stud either," said Theo as he lent in for a kiss. I saw the local gossip aunt, Karin McDougle, nearly toppling out her bedroom window as I kissed Theo. I grabbed the stud behind the head and drove my tongue in there. Theo had not expected that. "We're being watched by our beloved block-captain," I grunted while slobbering my man. Theo laughed and made a show of it too. Most of the people in our street could not stand that nosy McDougle woman.

Tylor had walked over to us. "Hey, boys... WOW... I've got food if you kids need a proper breakfast instead?" joked Theo's stepdad to us.
"Nah... Putting on a show for Karen McDo-nothing... 'daddy'..." I said with a grin to Tylor.
"Ah... ha ha ha... Okay then... Ummm... Son," said Tylor glaring at Karen's bedroom window. She shot back inside as soon as she saw the butch Jamaican Tylor Cummingham looking meanly in her direction.

Tylor told me that he had been texting with my father and Craig all last evening. They discussed what Craig's law firm had found out so far about the schemes of Jeff Skylar. It turned out that Jeff Skylar was a master extortionist. He owned much more property than just the gym. Using the places for him and his mates to abuse young men and women there. Videoing their brutal attacks and selling them online on the black market. Tylor's mates had found enough evidence of Jeffy-poo's wrongdoings to put him away for life. My father's property firm was planning to take most of the building lots over. Making plans to renovate them. Tylor Cummingham excitedly said, "According to your dad, we need a long talk about what you think we should do with the gym, though..."

I instantly started to dream out loud. Telling Tylor Cummingham that I saw him as the gym's owner. Saying that, all I wanted from that place was a gay-friendly gym to work out at. It would have to be brought into this century, though, as long as they kept the homely feel of the place. It should be a workout spot and club where dads can take their sons to by day and get their rocks off by night in the men's club underneath it. Complete with all the adult workout equipment that came with a saucier, gay-friendly hangout spot.

I explained convincingly, "... And if their sons want a place to do some naughty experiments, then just give them some glory holes in the gym's bathroom stalls... I just need you to promise me that you ban assholes like Jeff Skyler... Everyone should feel completely safe there!... No matter if they are gay, bi, or straight... Or how old they are or what color their skin has." I also told Tylor and Theo that we did not need more seedy biker bars in this town. But, with a naughty glint in my eye, I said that I would encourage leather men to join. Saying that, it should be a place to take a load off or rub one out. A men's club complete with bar, stage, and backroom dungeon under the gym. I told Tylor with a very dirty grin on my face, "... And if you ask me, the gym itself could do with a sauna and an indoor swimming pool, too... But I guess I am just dreaming out loud now."

"Son, I need you to stop talking for a moment!..." said Tylor suddenly, looking flustered at Theo and me. His monster anaconda slong had worked itself free. Poking its erect pre-cum dripping head out from under the kickboxing shorts Tylor liked to wear. Making one of his dark legs glisten in the sun. The three of us just stood there for a few minutes. Gazing at Tylor's throbbing bulge.
"Ha... 'daddy'... I think I have said enough... By the looks of it, the message has come across loud-and-clear," I said after a while to Tylor Cummingham.

"Benny is right... dad... I'd like to help you make that dream a reality... But, Gawd, I would love to work out in a place like that as well, sir... I can see it now!... 'Tylor's workout Club, A place where boys become men. And men become friends for life.' A gym for guys aged 12 and older. A men's club for real men 18 and above." sighed Theo dreamily.

"Cool... glad we are all on the same page then... Tylor, go take a cold shower!... I am going to use my dad's old pushmower to cut the grass and get a full-body workout at the same time!" I said laughingly to the horny men. Giving Tylor and Theo a small kiss over the fence. Theo's gang walked past us just at that moment. Looking at the surprising threesome smooching over the backyard fence.

"Wait... I got something for you, Boo," said Theo. Handing me his 6-inch tactical switchblade. "Every tough guy needs one, Benny."
"Oh gosh!... Thanks, Big-T... It may come in handy someday... But I rather not have to use it... Appreciate it if you can show me how to use it later, stud," I said in awe of the unexpected gift. If my mom knew I owned a knife like this, she would probably cut my balls off with it. Before she kicked me out of the house. All of this was witnessed by Theo's astonished gang.

"What are you lot looking at?" barked Theo to his posse, staring at us from the alleyway. "... Can't I give a friend some help?"
Theo's gang heard the finality of the words in Big-T's voice. None of them dared to question Theo about it and left for their usual hangout spot near Karen McDougle's backyard at the end of the street.
"Big-T... go and join your boys... I'll be along later so you can properly introduce me to them, stud," I said, gesturing to Theo to join his gang.

I greased up the old pushmower and set out to work. It gave me a great workout. I was sweating like an otter in no time. Mowing the backyard had given me time to think about what Tylor told me. If I wanted any involvement with that gym, then I better ditch the navy school idea for a business management college. That had the added benefit that I would not have to leave town. And dad would be chuffed to bits about that as well. He had always wanted one of his sons to follow in his footsteps.

While I worked in our yard, Karen McDougle, curious as she always was, had walked three or four times past us in the back alley. Wanting to see what I was doing. Hoping to hear what Theo and I were talking about. His mates were shooting some hoops nearby.
"Jesus, McDougle," I shouted when she showed up for the fifth time, "Can't you just put up a security camera or something?... Or do I need to call the police for stalking?..." I sneered loudly at her.
"Mind your tongue, Benson Long!... Your mother will hear about this!... God does not allow you to do yard work on Sundays, boy!" said Karin McDougle haughtily.
"Grass grows on Sundays too, you know!..." I called angrily back. It made Theo's gang role on the floor in laughter, "... And since when do you think you are God?... Get some psychological help, woman... And leave us be... Jeez!"

Several neighbors, Mark, Philip, Jimmy, and Doc Brown, rushed outside to see what the commotion was all about. That made Karen McDougle cower away. She pointed her hooked nose in the air and toddled home on her Sunday best high heels. The neighbors angrily called out to her too. And Theo's gang annoyingly stalked her all the way to her backyard. Bouncing their basketball menacingly around the gossip aunt. Mark clapt a hand on my shoulder. "You showed her good, bro!... You're in so much trouble now!... Mom is definitely going to hear about this one," he laughed meanly.
"That was still worth it!..." I said, without a care in the world.

Theo and his gang came back and hung over our backyard fence. "Good one, bro!...", "Nice work, Ben!...", "Did not know you had it in you, man..." called the guys proudly to me.
"Come shoot some hoops with us, Boo?" asked Theo. His mates looked in surprise at their leader's request. "Did Big-T really call that kid his Boo?... Is there something going on between these two?" You could see the guys thinking. Since Theo and I acted as if nothing special had happened, the gang dropped it and went on as if everything was cool with them. That made me sigh in relief.

"Later perhaps... I want to weed-wack around the basketball court first, guys!" I called as I put the pushmower away. As soon as I had trimmed the grass on both sides of the back street, Karen McDougle was back again. Yelling and screaming that I was making too much noise on Sundays. And about all the grass-clippings over 'her' road. I ignored her. Leaving her standing at our backyard gate. Picking up our high-powered leaf blower from the shed. I proceeded to blow all the clippings and dust away from the homemade basketball court. Covering the McDougle woman in a hail-storm of sand when she did not want to step aside. In the end, one of the other neighbors had to step in. She pulled Karen angrily away and gave her a good telling off. The other neighbors applauded her for doing so. Karen slinked away, and the guys and I played basketball the rest of the morning as friends.

Mark got a text from Dad. "- exit hwy in 3 min -" read his shorthand text. This was a clear warning that our parents were nearly at home. Mark and I cleared up and said our goodbyes to the men. Doc Brown and Jimmy rushed out via the back alleyway. Philly gave me a bro hug and whispered, "Hang in there kid... It will be fine... And if not, then you're welcome to use my place to hide out anytime you like," said Philip warmly. He even gave the security code for his apartment to me and left too.

"What was that all about?..." asked Mark, after he had kissed Philip goodbye as well.
"He told me I could use his place anytime I need to get away from here... And I fear I may need to take him up on that," I sighed softly.
"Ha, Yeah, I think Philly really likes you, bro... Just don't abuse that right... Philip is not the forgiving kind," said Mark with a brotherly hug. Mark already had his army uniform back on. And that made me realize I may be on my own here pretty soon too. Having to deal with my opinionated mother by myself. As well as her girlfriend, Karen McDougle, from up the street.

Mom did not say much to Mark or me when they arrived, walking up the garden path to the front door. She just looked in disgust at my grass-stained pants. She was frowning at my new haircut, the sunglasses, and in shock at the little earring in my 'gay' ear. Ignoring me, she gave Mark a warm hug and told me harshly to get their suitcases out of the car. Looking up and down the street to check that no one was watching us.
"Nice to see you too, mother!" I sneered as I walked past her and Mark to the car.

My father clapped a reassuring hand on my shoulder. Asking me how my holiday had been going. I instantly knew that Mark and Tylor had been filling him in.
"Oh hi, dad... yeah... It was a bit shorter than I would have liked, though... But what's done is done!" So I told my old man, "... Tylor wants a word with you asap... I explained my vision for the gym to him... He seemed very excited about the ideas I floated around."

Dad asked me to move their suitcases upstairs. And to change back into my new cool look that Mark had told him about. According to him, there was no need to hide my latest purchases from my parents. He said reassuringly, "It sounds like you finally found your sealegs this summer... And don't you mind your mom... She'll come around, eventually." Giving me a short hug and looking very pleased at my new earring.
"Are you coming inside, Doug?" asked Eileen, my mother, from the front door. "... No sense in standing out here... What will the neighbors think, dear?"

I changed into my new pair of dark-blue jeans. Well, I say new, but it did have a few designer rips. I put a thick leather belt around it. With a blue-gray mottled long-sleeved V-neck shirt. My thick Cuban curb necklace and the leather wrist wallet completed the 'new me' look that I was going for. I put the short biker boots under all of that. The boots had been given a good polish, so they could pass inspection, I thought. Combing my styled hair, I hung my Rayban's in the V of the shirt. And slipped Theo's signet ring back onto my finger. Looking like a million dollars, I went back downstairs. Catching my new look in the hallway mirror, I thought to myself, "That's a heck of a lot better than mom's ugly colored pleated trousers and dad's old office shirts with a tie."

Well, as expected, mom yelled up a storm when I walked into the living dressed like that. So I just stood there and took it like a man. Dad and Mark did not dare to step in. Until she shouted, "... No son of mine is going around dressed like a hobo in torn clothes!... Boys need to dress in the clothes they are told to wear, Benson Robert Patrick Long!... " She used all my names. So I knew she was utterly pissed off at my new look.

My father glared dangerously to his wife and called, "Now, hear woman!... You are going way too far!... Benny is turning 18 in two weeks!... I paid for this new look... And he is dressed like kids of his age should be... You've dressed him up in stuff that went out of fashion 50 years ago... That says more about you, Eileen, than it does about Benson!... And he is not 10-years-old anymore... He is old enough to buy his own clothes from now on out... You do good to remember that, woman!..."

Mark and I had never heard our father talk to his wife like that before, ever. Eventually, mom got up and left via the kitchen door - No doubt to visit her friend's house to hear the latest gossip.
"Jeez, dad... That was pretty harsh," sighed Mark. I was too emotional to speak and about to storm away myself. Dad got up and guided me to the couch. He sat next to me. Taking a very close look at my earring and the signet ring on my finger. He also spotted the friendship bracelet as he held my trembling hand in his.

"Is there something you'd like to tell me, Benny?" asked my father calmly, "... You know you can tell me anything, don't you, son?"
"Nothing that you don't already know, dad... Or that you have already guessed at, sir... But I do have a few more things in the works," I sighed with a soft whimper in my voice, "But I do like it when you call me Benny... You've never done that before, dad."
"That's true, Benny, but times change... I like your new tough look... I guess those Judo-classes were good for something, right?"
"Nope, they were definitely not!... Doug... Ummm, dad... I stopped them!... I found that body workouts do a lot more for me than the stupid judo classes ever could."

"Okay... But I really think you should have discussed that with your mother and me first, though, Benson... But I can see you have used your holidays well this year... I am glad you finally found your sealegs, Benny... Mark told me you had a bit of trouble in the gym too... Helping you find your true self... Kid, I really don't care who your dating... As long as you're happy and, above all, safe... Is it anyone we know?" asked Doug, pointing at the signet ring.
"Theo from next door..." I calmly answered, "But don't tell mom just yet... I want to do that myself when I feel ready!"
"Oh, is he now?... I thought you did not like him?..." said my dad worriedly.
"As you said, sir... times do change!" I answered confidently.

"Good for you, Benny... I've got your back, boy... You don't know how proud this makes me... You just do the new you!... And I'll make sure mom won't get on your back too bad... You know, I have dropped anchor in poo-bay quite a few times in my navy days myself," told dad to Mark and me unperturbed.

I think that afternoon, I may have lost a parent but gained a best friend. The next few weeks until my eighteenth birthday turned into the toughest times I had experienced until then.

< Continued in Dreaming of Leather men - part 6 of 8>


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(C) StrykerJ: June 2021

by StrykerJ

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