Jim and I Pt. 07

Story Info
Jim and I try anal play in our underwear.
2.4k words
4.51
4.4k
4

Part 7 of the 8 part series

Updated 10/03/2023
Created 10/18/2022
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

"Hey man, what are you up to?" the text from Jim read

"Just working at home in my underwear, like normal" I quickly replied

It had been a couple weeks since we were all sent home from work but luckily Jim and I were both able to still telework. I know I was taking full advantage of spending most of the work day in just a t-shirt and underwear but I don't think Jim was as lucky since his wife and son were home all day too. Since we hadn't been going to work, we also hadn't been to the gym in a while and I know I definitely missed seeing Jim in person. We exchanged a couple snapchats in that time of what we were wearing but it didn't make up for seeing Jim's bulge in person.

"Sounds great! Mind if I join you?" Jim replied

I eagerly agreed and Jim said he would be over in a few minutes. I cleaned up my house a little bit and brewed some more coffee for us to share. No reason to get dressed since I knew my pants wouldn't stay on long with Jim coming over, but I was hoping he'd appreciate the black camouflage pattern Under Armor boxerjock I had on. It wasn't long until I heard Jim's truck pulling into the driveway and soon he was opening my door with a big smile.

"Hey buddy, I missed you!" Jim said while opening his arms and inviting me in for a hug. I rested my face on Jim's chest and inhaled the warm, clean, manly scent that I've missed for several weeks while wrapping our arms around each other. Our hug lasted for a minute or so while we re-acquainted ourselves with the feeling of each other's bodies. Damn, I've missed this so much.

Jim broke our embrace and pulled his laptop out of the bag he brought saying he wanted to set it up quickly so he didn't appear away on Teams. I helped Jim connect to my Wi-Fi and then grabbed a couple cups of coffee from the kitchen, doing nothing to hide some of the excitement I had going on in my boxerjock. When I returned, Jim had set his laptop on the coffee table next to mine and was starting to undo his pants.

"Like I said, I was gonna join you working in your underwear" Jim winked and smiled as he pulled down his jeans to reveal his blue Under Armour boxerjock. Jim slid the jeans over his feet as I stared at his package shifting in the tight synthetic fabric. He came closer to me a reached out to grab a cup of coffee with one hand while reaching for my bulge with the other. I returned the attention to Jim's expanding bulge while we smiled at each other and took a few sips of coffee.

Jim and I sat down on the sofa next to each other and picked up our laptops to make sure there were no new emails to chats to deal with. Luckily it was a pretty quiet day which gave Jim and I a chance to catch up and enjoy being with each other for a while. Jim wrapped his arm around me and pulled me closer while placing his leg over mine so that our boxerjocks were touching while we chatted about everything that has been going on.

We spent the next few hours working from the sofa, chatting, and sipping coffee just in our boxerjocks. Every so often we'd take a few minutes to play with each other's bulges or grab each other's asses though the tight, stretchy fabric when we got up to get more coffee or go to the bathroom. Probably not the most productive time at work, but it sure was a morale booster after being separated from each other for so long. Luckily Jim's wife was happy to get him out of the house for a few hours since she could tell he was getting moody.

Around lunchtime, Jim quickly closed his laptop and stood up to stretch -- placing his bulge directly in front of my face and slyly shaking it to focus my attention. I didn't need much encouragement and quickly closed my laptop as well. I reached out and placed my hands on Jim's hips to guide his Under Armour-clad package towards my head and buried my face into the blue fabric. I massaged Jim's ass, teased his taint and hole, and played with the waistband of his boxerjock while licking and sucking his hardening cock and well-supported balls through the fabric.

Jim let out a pleasing sigh and gently stroked my head and shoulders to encourage me for a minute or so until lifting my head and pulling me into a standing position. Jim drew me close to him and we deeply, passionately kissed each other with hardened cocks pressing into each other through the tents in our boxerjocks. We made out for several minutes, embracing and kissing lips, necks, shoulders, and chests making it abundantly clear how much we missed each other. There was a slight pause in the action while we just looked at each other and smiled and Jim took that opportunity to lead me back to the bathroom.

Jim leaned into the shower to turn the water on while I admired his muscular ass in his tight blue underwear, reaching out to gently massage his glutes. Once the water was warm, Jim stepped into the shower still in his boxerjock which immediately stuck to his skin and showed every detail of his anatomy. Jim reached out and pulled me into the shower with him, embracing me as I watched the water run down his beard and slightly hairy chest. I split my attention between kissing him and gently licking and sucking his nipples which I could tell really got Jim excited all while jerking his cock through his skin-tight Under Armour.

Jim dropped to his knees and placed my wet, boxerjock-clad cock in his mouth for a few seconds before pulling my underwear off entirely. Jim swallowed all six inches of my rock-hard cock and deep throated me while we reveled in what we haven't been able to do in some time. While taking a breath, Jim grabbed some soap and began gently washing my ass and hole, teasing it with his finger at every opportunity, while resuming his oral service of my cock. Jim turned me around and bent me over the shower bench so that my hole was directly in his view. After rinsing the soap away, Jim buried his face in my ass and began rimming me with fervor and I loved feeling his beard on my hole and taint.

Jim spent a few minutes providing oral attention to my hole while slowly jerking my soapy cock, grunting and groaning with the pleasure we were both feeling. Jim stood up and pulled me along with him, leaning in for a long deep kiss between us.

"Fuck, dude, I missed this so much. I've missed you so much. I'm so fucking hard in this underwear and I love it!" Jim exclaimed once releasing me from our kiss. "Hold on one second."

Jim turned off the water and stepped out of the shower. He pulled off his tight, wet boxerjock to release the throbbing seven inches that had been constrained. Jim picked up my wet underwear from the shower and threw both our pairs into the sink while walking into my bedroom. After a minute, Jim returned wearing my white Under Armour jockstrap -- hardly containing his fully erect cock -- and carrying a black Nike jockstrap which he handed to me. I put on the jockstrap while Jim stepped back in the shower, gently massaging my shoulders and arms. We took a few minutes to admire each other in our new jockstraps, playing with our cocks and snapping the leg-straps to tease each other.

"I checked the clock and we've still got at least 30 minutes left in lunch. I want to make the most of it." Jim said while turning the water in the shower back on and handing me the soap. "I would love for you to wash my ass and finger my hole" he added while bending over slightly against the shower wall. I took no time to begin soaping Jim's ass, letting the soapy water run down his taint and into the pouch of his jock. I teased his hole with my soapy fingers while alternating attention on his now soapy bulge tenting out of his jock.

Jim gently moaned with pleasure each time I passed his hole and let out a low grunt the first time part of my finger went inside him. I went slowly to ensure Jim was comfortable but it was clear after a few seconds how much he wanted to be fingered; Jim reached one hand behind him to pull his ass apart, driving his hips to encourage me to go deeper. I gladly obliged and continued to finger fuck my buddy with one hand while feeling his ass, balls, and cock with the other. Jim grunted and groaned with the pleasure he was feeling, alternating his hands to spread his ass and play with his nipples. After a few minutes, I slowly removed my finger for the last time and placed my hands on the waistband of Jim's jock to encourage him to stay bent over.

I soaped up the pouch of my jock -- still strained from my erection -- and rubbed it on Jim's hole. We both thrust our hips so the technical fabric wrapped head of my cock could tease Jim's hole as much as we both wanted. I played with Jim's nipples and cock, snapping his jock, and slapping his ass while I nearly fucked him for a few minutes. Jim's hole was getting sore from all the attention so he reluctantly stood up and turned around to me with a big smile on his face. "I hope you're ready to see me cum because I can't wait to see you bust your load." Jim remarked while turning off the water.

We slipped off our wet jockstraps, placing them in the sink with the rest of our wet undergear, and toweled off before heading onto my bed. Jim laid me down and crawled on top of me, his towering, muscular frame a sight to behold, and we kissed for a few minutes while Jim jerked our cocks. Jim removed his lips from my mouth and worked his way down my body kissing everything he could until reaching my cock. Slowly took it into his warm, wet mouth and gently sucked me knowing how close I was until blowing my load. After a couple minutes of slow and deliberate sucking I let Jim know I was ready to cum.

Jim removed my cock from his mouth and continued to jerk me off encouraging and nearly pleading with me to cum on his face and beard. It didn't take long until I was shooting multiple thick shots of cum all over his lips, cheeks, beard, and some in his hair. Jim closed his eyes and enjoyed the warm load being delivered to him but quickly returned my cock to his mouth to suck out the last drops and continue to pleasure me through the end of my orgasm. He gently sucked my cock for a few minutes as my erection subsided and I could feel my own cum dripping off of his face and onto my body. Once Jim was satisfied he extracted all of the cum he could, he laid down on the bed next to me and leaned in for some more kisses while jerking his still hard cock.

I reached down to find Jim's seven hard inches and took over for him. Jim put his hands behind his head to enjoy the manual stimulation while I reached into my bedside table to grab some lube. I lubed up Jim's cock and continued to jerk him while slowly allowing my fingers to drift down to his hole. Without hesitation, Jim lifted his hips to allow easy access while I lubed and teased his hole with my fingers. Jim's breathing intensified and told me he was close to coming; which only encouraged me to jerk and finger faster. I felt Jim's ass clench on my finger and soon saw load after load of cum shoot out of Jim's cock, landing on his chest, and causing him to moan in pleasure. I continued finger Jim's ass while slowly my jerking to lead him through the end of his orgasm, with a few smaller squirts of cum leaking out when I may have hit his prostate.

I slowly removed my finger from Jim and leaned up to kiss him. We headed into shower once again to cleanup, enjoying each other's company and bodies while we washed. After drying off I let Jim pick out some underwear for us: low-rise red Jockey sport briefs for me and low-rise black Jockey sports briefs for him. We headed back to the living room to sign back into work after our lunch break -- surprising how much you can get done in an hour. I made some sandwiches for us while Jim caught up on his email.

"That was so much fun, I really missed you." Jim said between bites of his sandwich. "I hope I didn't surprise you too much with the butt stuff, I've been playing with myself in the shower at home a little bit and wanted to experience it with you."

"No problem it was fun and I'm glad you liked it." I replied. "I've really missed you too and still can't believe such a hot guy like you is into all this stuff."

Jim smiled and leaned in for a kiss. We finished lunch and I cleaned up as well as threw our soaked underwear in the dryer. Jim and I cuddled on the couch for a while, working in our briefs and enjoying each other's company -- of course rubbing the other's bulge in between typing on the keyboard. Jim broke our contact after about an hour saying he should probably head home. I watched him get dressed, sliding his jeans over the smooth black fabric hugging his toned and tired ass and stood up to give him one more hug before heading out the door.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
4 Comments
AnonymousAnonymous7 months ago

Really hot story!

spankedpussyboyspankedpussyboy7 months ago

what an amazing and sexy story.

FitGuy47FitGuy47about 1 year ago

A very hot series. Looking forward to the next session. I can see someone loosing their anal cherry soon. Hehe. Thanks for sharing

dnsontndnsontnover 1 year ago

This is both excruciating and satisfying! Happy to catch up and see there will be more!

Share this Story

READ MORE OF THIS SERIES

Jim and I Pt. 06 Previous Part
Jim and Series Info

Similar Stories

Bathing Suit Dilemma Two straight guys get surprisingly horny in the Jacuzzi.in Gay Male
Slutty Sleepover Two, straight best friends make some discoveries.in Gay Male
It's Not Gay, It's Just Sex My brother-in-law and I learn to satisfy each other.in Gay Male
Straight Turnout Strait guy is turned out by an experienced man.in Gay Male
Two Friends Share A Halloween Costume Straight buddies enjoy gay sex inside a costume.in Gay Male
More Stories