Jim and I Pt. 08

Story Info
More underwear and anal play with Jim.
3.2k words
4.5
3.5k
6

Part 8 of the 8 part series

Updated 10/03/2023
Created 10/18/2022
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"Ok, let me grab a shower and I'll head over" the text from Jim read.

Jim and I had been trying to schedule some time to get together for a few months, but life just seemed to always get in the way. I know Jim had been on a couple hunting trips and we've both been dealing with hectic work issues and family commitments. We've texted and snapchatted, but it had slowed down as other things in life took over. Needless to say, we both were looking forward to some time for just the two of us.

I heard Jim's truck pulling into the driveway and felt the bulge in my red Under Armour boxerjock begin to grow in anticipation of seeing my buddy. Jim opened the front door and I met him with a cold can of beer which he gladly took a large sip from before meeting my lips for a kiss. Wordlessly, Jim moved his head away and with some slight force led me to the couch and pushed me to a sitting position. He chugged the rest of his beer and dropped the backpack he brought over before getting to his knees and burying his face in my crotch. Jim's lips and tongue explored everything that was covered by the tight fabric with the hairs of his beard occasionally poking through for some extra stimulation while I sat back and enjoyed a beer and the sight of my buddy servicing me. It wasn't until the pouch, taint, and most of the legs of my boxerjock were completely soaked with Jim's spit that he pulled his face up for a break.

"Fuck you taste and smell so good!" Jim added as he reached for my beer to wet his parched mouth.

Jim stood up and I reached out to undo the button and fly on his shorts and quickly lowered them to his feet. I was a little surprised to see Jim wearing a pair of crisp, white, cotton, Hanes briefs but he looks good in everything. As Jim had done for me minutes earlier, I buried my face into the clean cotton and inhaled the slight but definitively masculine scent of my buddy. Jim sipped his beer while gently resting his hands on my head and voicing his enjoyment and encouragement. I spent special attention to lick Jim's heavily balls as his briefs strained from his hard 7" cock and absorbed my saliva. I ran my tongue along the sides of his pouch, gently massaging the base of his cock and balls with the tip of my tongue before making it down to his taint. I ran my hands up and down Jim's legs, grabbing his muscular ass through the briefs while occasionally adjusting my hard 6" in my damp underwear.

Jim finished his second beer and gently guided my head up and away from his crotch to his face. We made out for a little while our saliva-soaked bulges rubbed against each other, aching for relief.

"I told my wife I was going to spend the night, so I feel like I could swallow your load now and hopefully you'll have another one for me a little later." Jim said with a mischievous smile on his face while breaking away from our kiss.

"You know where to find it and you're more than welcome to swallow as much as you want!" I responded matching his gaze and smile. "But first, let me grab a beer so I can catch up to you"

I grabbed a beer from the kitchen while Jim slipped off his shoes and out of the shorts still resting at the bottom of his feet. Jim removed his t-shirt and got onto his knees in front of the sofa just in his white briefs. I walked over to Jim and ran my fingers through his hair and beard, running them along his lips, and gently probing his mouth while finishing my beer. When I was done, I set the empty can down and bent over on the sofa placing my ass, still clad in the form-hugging underwear, in front of Jim's face. In no time at all I felt Jim's large hands on my backside and felt his beard and tongue pressing on my hole through the tight red fabric. After a minute or so, I told Jim to remove my underwear and he happily complied before quickly slipping his warm togue into my hole.

Our excited grunts grew louder as my hole relaxed and Jim worked his tongue deeper into me. Jim used his strong, thick hands to gently spread my cheeks and massage my legs as he rimmed my hole and licked my taint and balls. After a few minutes, Jim turned me around and sat me down on the couch before fully swallowing my throbbing cock deep into his mouth. Jim jerked his cock through his tight white briefs, alternating his hands to jerking my cock, rubbing my chest, and gently playing with his own nipples. The sights, sounds, and actions of Jim quickly drew me to orgasm, and I shot multiple ropes of thick cum down Jim's throat while he grunted with the pleasure of tasting my 3-day load. Jim continued sucking out anything he could while I felt my body relax and sipped on my beer. A couple minutes of gentle sucking and licking left Jim satisfied he'd extracted every last drop of cum as my cock began to soften.

Jim looked up at me, smiled, and thanked me for letting him swallow my load. I smiled and returned my appreciation, but Jim was already on the move. He pulled me to the edge of the sofa and turned around between my legs. While facing away from me, Jim situated himself under my taint and balls and began licking again while jerking his cock through his briefs. I enjoyed Jim's renewed attention and watched as he slipped off the briefs and jerked his throbbing member. I leaned over to massage Jim's nipples and reach down to play with his cock and balls while he edged closer and closer to cumming. With a few solid grunts, Jim wrapped his white briefs around his cock and unloaded pump after pump cum into them. In his orgasmic state, Jim removed my balls from his mouth which I took as a sign to lean over and kiss Jim deeply as I massaged his chest and played with his nipples.

I crawled off the couch and pivoted my body over Jim, sitting down on his legs and continuing our make out session. Jim wrapped his arms around me and drew me into his tall, muscular, and slightly hairy chest -- our still semi hard cocks nearly intertwined. I moved my head down to lick Jim's nipples as he ran his hands on my neck, back, and ass as he gently massaged me to relieve any last bit of tension in my body. I rested my head on Jim's chest, slowly inhaling his scent as he rested his head on mine and continued to hold me. It felt so perfect to be together again that we quickly, but briefly, fell asleep letting our exhausted cocks finally relax.

Jim woke up first and gently rocked me awake. I opened my eyes and met Jim's gaze, leading to a few more soft kisses. We slowly stood up and stretched out, collecting our clothing from around the room, and walked to the kitchen for another beer. Jim and I admired each other between sips, discussing how much we've missed our time together, before finishing our drinks and grabbing a quick shower together. We both threw on some tight black boxer briefs and t-shirts before returning to the living room for some TV, beer, and ordering a pizza.

"I've never seen you in old school tighty whities, but you look perfect in anything. When did you get those?" I asked Jim as we waited for the pizza.

"I was hoping you'd ask!" Jim responded with a smile. "I... guess you could say... borrowed them from my buddy on our last hunting trip. I saw them sticking out of his bag while I was in the truck for something and couldn't resist grabbing them. Hope he doesn't notice."

"Wow that's so hot" I replied while sipping my beer "It makes it even hotter that I got to lick your balls in his briefs and that you shot your load in them. Guess I've been a bad influence on your life of crime."

Jim laughed and put his arm around me while we continued drinking and talking on the sofa before the pizza arrived. The doorbell rang and Jim slipped on his shorts to grab the pizza, letting them drop and kicking them off as soon as the door was closed. We enjoyed pizza, beer, and each other's company for the evening, laying together on the couch in our boxer briefs. Once the pizza was gone and we were sufficiently drunk it couldn't resist anymore and laid my head on Jim's chest while reaching down to play with his soft yet meaty package through his underwear. Jim nodded his head back to enjoy the attention while rubbing my torso to encourage me for a couple minutes before gently lifting me up and standing off the sofa.

"I was waiting for round two to bust this out but wanted to show you something." Jim said as he walked over to his backpack and started reaching inside. Jim pulled out his trusty black jockstrap and then pulled out a small conical object. "Check it out, I got this little toy that I was hoping we could try out. It vibrates!"

Jim handed me the toy and I briefly examined it, accidentally activating the vibrate function. Jim and I laughed but he removed it from my hands and placed it on the pouch of his boxer briefs to see how it felt, passing it back to me after a few seconds. I did the same to the pouch of my own boxer briefs to see how powerful it was, enjoying the feeling on my balls and taint. While I was enjoying that, Jim stripped out of his t-shirt and boxer briefs and pulled his jockstrap up and over his muscular glutes, arranging his ample and hairy package into the pouch. Jim laid on the couch facing me, placing his legs over my own and gently massaging my bulge with the heels of his feet.

"I've been waiting to try this with you." Jim said as he gently played with his semi-hard cock in the pouch of his jock. "If you go into my bag, there's some lube that you can grab. I'd love if you'd help me get it into my hole."

I eagerly agreed and jumped up to grab the lube while Jim re-situated himself on the couch. I crawled on top of Jim and in-between his legs to meet him for a kiss as he opened, lifted, and spread his legs for easier access. I used a small amount of lube to gently massage Jim's hole and taint so conveniently accessible while he was wearing a jock. As Jim relaxed, I worked my finger into his hole bit by bit to get him acquainted with the feeling. Jim closed his eyes and gently moaned, switching between rubbing his rapidly hardening cock and playing with his nipples.

By the time I was able to get most of my middle finger into Jim we both agreed that he was ready. I slowly removed my finger and applied a small amount of lube to the toy, gently inserting it into Jim's hole and making sure not to turn it to vibrate mode just yet. He moaned with pleasure as he received the toy, and I gently and slowly pushed it into him. Jim reached down to pull his ass apart making sure I had as much access as I needed and encouraging me to keep going. Within less than a minute, the end of the toy met the edge of Jim's hole, and I watched him squirm with pleasure as he adjusted to all the new sensations. Once his breathing and moaning calmed down a little bit, I activated the vibrate.

Jim's body immediately reacted to the new sensations as his prostate was stimulated. He grabbed it by hand and moved it to his package before moving his own hands to play with his nipples. I was so turned on seeing my buddy in such bliss and I was happy to help him explore these new pleasures. I jerked Jim's hard 7" through his jock for a couple minutes before sliding his cock out of the pouch. I gladly accepted most of Jim's cock into my mouth, tasting the precum that had already been leaking from his stimulated prostate. Jim grunted, placed one of hands on my head, and thrust his hips into my face. I reached down to play with Jim's balls and tease the vibrator in his ass, each time he moaned and thrusted even more. It was only a couple minutes until Jim signaled he was getting ready to cum. I released his cock from my mouth and Jim grabbed his cock with two hands while reaching full climax. A few seconds later cum erupted from Jim's cock shooting up and onto his face, the sofa, and my face as well. Jim groaned and opened his mouth to taste his own seed as shockwaves of orgasmic pleasure washed over his body. I massaged Jim's legs and torso as his body relaxed and I made my way up for a kiss, mixing the cum on my beard with the cum on his. I reached down to help Jim slowly remove the vibrator from his hole and turn it off as his heart rate and breathing returned to normal.

Jim slowly slipped out of his jockstrap and used it to wipe the cum off himself and the furniture. He took the toy from me and wrapped it into the pouch of the jock, gently fingering his own ass where it had just been. Jim sat up and rested his hands on my thighs, playing with the fabric of my boxer briefs and teasing my hard cock with his fingers.

"Needless to say, that was amazing! Thanks again!" Jim exclaimed as he smiled at me and moved in for some more kisses. Jim moved his hands up to my torso and gently laid me back on the sofa, moving his kisses down my neck, chest, and to the waistband of my boxer briefs. Jim paused to inhale the smell of my bulge before beginning to lick and suck me through the tight black fabric.

"No worries, man, it was so hot. But hey, let's get you cleaned up before we focus the attention on me." I said lifting Jim's head from my lap.

He looked a little puzzled but was happy to go along with the suggestion. I led Jim back to the bathroom, watching his now mostly soft cock and empty balls bounce between his muscular legs. I turned on the shower and after letting it warm up stepped inside and invited Jim to join me. I soaped Jim's chest and cleaned downwards as I massaged his body, paying gentle attention to Jim's overworked cock, balls, and hole. Jim softly moaned and reached to return the attention to me while I was still clad in my now soaking wet boxer briefs, massaging my bulge before pulling the tight, wet garment off my body.

Jim and I spent 20 minutes under the shower helping each other clean up in between kissing, hugging, and massaging each other. We stepped out of the shower and dried off before heading to my bed where Jim tenderly laid me down on my back and took and opposing position with his head at my cock. Jim planted his knees on either side of my body planting his face into my crotch and placing his muscular, hairy ass and balls in my face. While Jim licked my balls and quickly hardening cock, I lifted my head to lightly rim his hole and lick his taint and balls. Moments later I was fully hard, and all six inches of my cock were immediately engulfed in Jim's throat. I laid back and let Jim work his oral magic while I massaged his glutes, jerked his cock, and played with his low-hanging balls

Jim worked on me for several minutes knowing exactly how to please me, bringing me to the edge of orgasm multiple times but never letting me release. I could feel the pressure building in my cock and balls and the uncontrollable thrusting of my hips into Jim's face, which he gladly and aptly handled. I told Jim that I was ready to feed him my load and he grunted an affirmative before tightening his lips and matching the rhythm of my thrusts to serve as the perfect face fuck. I felt my load within seconds and reached out to hold Jim down on my erupting cock, but he had no problem taking shot after shot of hot cum down his throat. I could feel and hear him swallowing my load as he grunted with delight for his reward.

As my orgasm came down from its climax and Jim sucked the last few shots of cum out of my cock, I moved my hands back to massage his ass and balls, closing my eyes and relaxing while enjoying the physical company of my best friend. Jim continued gently sucking my cock for several minutes as I completely relaxed and nearly fell asleep. Before I could, however, Jim shifted his position so his face hovered over mine, meeting my gaze and inviting me to kiss him. I tasted my cum on Jim's breath as we made out for a while before he moved his face down my body kissing my neck and nipples before gently relaxing his head on my chest. I massaged Jim's head and neck as he moved his hands across my upper body, returning the attention and enjoying our intimate physical touch.

"I still can't believe this is so much fun!" Jim said as he moved off my body and stood up next to the bed. He walked into the bathroom to grab us some towels to clean everything up from our latest session, teasing me with his flaccid and tired cock and balls as ran the towel over his body. Without asking, Jim walked to my underwear drawer and pulled out a couple pairs of Under Armour boxerjocks for us -- green for me and blue for him -- which we put on while admiring each other's bulges.

After brushing our teeth, Jim and I crawled into my bed with Jim wrapping his muscular arms around me as the big spoon. I nestled into his 6'8" frame and felt his bulge contained brush against the tight synthetic fabric around my ass. Jim gently kissed my head and the back of my neck while holding me tightly against his body. Before we both drifted off, Jim whispered "I've got an idea about those white briefs I want to run by you tomorrow. Have a good night."

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5 Comments
Exluke1Exluke16 months ago

Man, this has a tag of straight guys but it seems like they may just be falling for each other.

AnonymousAnonymous6 months ago

I have a huge underwear fetish and this is the best series I have ever found.

This is amazing, and you're great at it.

You have to write more

AnonymousAnonymous7 months ago

Next chapter can’t come soon enough!

spankedpussyboyspankedpussyboy7 months ago

Just discovered you....this is my new favorite series!

MarcLuciFerMarcLuciFer7 months ago

Great to see you back again and as hot as ever.

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READ MORE OF THIS SERIES

Jim and I Pt. 07 Previous Part
Jim and Series Info

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