ROOMING WITH MY BEST FRIEND - JACOB ENCOUNTER
This is a fantasy chapter written as a collaboration between Wasputz and Big D. While some of this chapter actually occurred in Sophomore Chapter 9, the rest is total fantasy and did not really happen. It has been written purely for your pleasure and as an example of how the fantasy section for “Rooming With My Best Friend” will work, offering alternative views of events that take place or featuring sexual acts that would otherwise not happen in the context of the main story. Any submissions from other readers are welcome as are suggestions for future fantasy stories written by either of the authors responsible for this chapter. We hope that you enjoy this addition which we are sure will be the one of many fantasy chapters.
“I better run, Jacob. You take care and remember to tell Gail I said hi,” I said.
“Hold on. Let me get a picture of you to send to her,” he said. He snapped my picture with his phone. I watched him send it to her before we said goodbye.
Watching him walk away in his hot ass skinny jeans brought back such great memories of all the times I tapped that ass. “Hey Jacob, stop for a sec.”
He turned his head with a flick of his dyed black hair and swept it from his face, “Yeah, what?”
“Ummm.. if you’re not real busy, I guess I could hang with you for a bit.”
“Sweet, I’d love that. You do know I live off campus, right?”
“No, I didn’t.”
“So, do you wanna follow me or ride with me?”
“I could ride with you, I guess,” I said. We walked to the crowded lot to find his car. I laughed seeing it was Gail’s old car. He jumped in and turned down the music but I turned it up since it was some kickin Smashing Pumpkins. We sang along to the songs with great memories of him and I.
Jacob pulled into the parking lot of his apartment block. At first glance, they weren’t anything special but I knew it was all Jacob could afford. He showed me the way and opened the door. Quickly I could see a big bong sitting on the coffee table.
“Sorry you saw that,” he said.
“I’d be even sorrier if you didn’t light that motherfucker up,” I said with a half smile.
“Seriously, you smoke trees?”
I laughed, “You saw earlier I’ve changed.”
“Wait til Ian gets here and we’ll for sure fire that fucker up,” Jacob said and took a seat. I sat near him and loved his scent. Not sure what he was wearing at the time but it smelled great. I was overwhelmed with urges. I leaned over and kissed him on the lips. It felt different kissing a guy with a pierced lip but not too bad. Jacob pulled me close with his hands running up the back of my shirt.
“Should we stop?” I asked.
“Fuck no. You’re a great kisser. I don’t care if Ian sees me macking with your hot ass. Matter of fact, he’ll wanna join us,” Jacob said and pulled me back for more. His hand moved from my back and grabbed my crotch. I didn’t know what came over me but I wanted this so bad. Corey had fucked around on me one time so I kind of felt like I was owed the opportunity just the once.
The door opened with a skinny spiky haired punk guy walking in the door. He sat down his things and walked over to join us. This dude was sporting a hot tongue ring and rammed it in my mouth, kissing me deep.
“So who the fuck did I just kiss?” Ian said laughing.
“Matt, my old boyfriend. You remember me telling you about him. The one with the fucking big ass cock,” Jacob replied.
“Hmmm… I see, but oh well,” Ian said. “He is fucking hot!”
“Tell me about it,” Jacob said. “The best part is he has a fucking hot boyfriend as well.”
“Awesome, dude! Does he love your big dick?” Ian asked.
I smiled with Ian pulling out a joint, “I fuck his hot ass as much as I can.”
“Boy, I remember how good your dick felt. All eight inches pushed way inside of me,” Jacob said.
“I really doubt he’s packing eight,” Ian said lighting the joint.
“If there was an eight inch dick, Matt is sportin one,” Jacob said before taking the joint.
I stood and dropped my shorts and boxers. I put my hands on my hips before Jacob put the burning joint between my lips.
“Fuck, even soft, it’s huge!” Ian said. He reached and grabbed it while I inhaled the joint. His hand felt so good and so soft. Then another hand, Jacob’s, began stroking my cock. Ian stood and stripped out of his clothes. His skinny body was littered with tatts. Looking down, I saw his cock had a nice PA piercing.
“Fucking hot, Ian,” I said.
Jacob was stroking my cock and moved to grab Ian’s pierced cock. “Matt, you don’t know how good this fucker feels in me.”
Ian took a hit and extinguished the joint. “I know three guys that are about to fuck!”
“Ian don’t bet your life on it. Matt is not that type…”
“Fuck that, Jacob. I’m here. Now I’m fucking hard as a rock with two very hot guys. Fuck Corey! I can have some fun every now and then and let others guys experience my big fucking dick! I for damn sure want Ian to fuck me so I can feel that PA up my ass!”
Jacob smiled and undressed. It had been a while since I had caught sight of his naked body. He was inked up like Ian with his nipples pierced and his flat hairy stomach with a piercing.
“He can join the crowd. We got this one hot fucking dude that loves to fuck around with us. Got the hottest swimmer’s body ever and a nice big uncut dick,” Ian said. “You talk about smoke some fucking weed!”
I smiled, “Does he have blond hair?”
“He does. His name is Stacy,” Ian replied.
“No, his real name is Scott. He’s a very good friend of mine. I know for a fact he’s one great fuck,” I said and remembered I had a picture of him. I reached in my shorts on the floor and found the picture. “Is this Stacy?”
Ian laughed, “Hell yeah it is.”
“Hey why don’t we just call him up?” Jacob asked. “He text me saying he wanted to fuck with us again.”
“Let’s not. I want you two hot fucks to myself,” I said.
“Alright then,” Ian said.
“Let’s go to my bedroom, there’s a bit more space in there,” Jacob said.
He wrapped his hand around my hard cock and pulled me along behind him until the three of us were standing in his bedroom. It wasn’t the biggest of rooms, not even as big as the room Kris and I shared at the dorm but the big difference was the double bed that took up more than half the space. I smiled as Jacob pushed me until I was sitting on the edge of the bed.
Jacob and Ian both licked their lips as I spread my legs to give them access to my throbbing cock. It was so exhilarating to just meet someone, shed our clothes and fuck. What added to the excitement was that it had been so long since I had any form of sex with Jacob I wanted to see if it was as good as I remembered and even better was the thought of getting my mouth and ass fucked by a dick with a PA, something I’d always wanted to try but never thought I’d get the chance to experience.
I thought of Corey for a brief moment and how it wasn’t really right that I was doing this but those thoughts soon disappeared as I felt two sets of lips kissing along the shaft of my big cock.
Jacob was on his knees on one side, with Ian in the same position on the other. They kissed my dick and started using their tongues to caress it, effectively kissing each other with my cock between their lips. Their tongues met as they continued to work my cock and I let out a shriek when I felt Ian’s tongue piercing swirl around the head of my cock for the first time. It was such a strange feeling but it sent a jolt of electricity through my body and almost made me cum on the spot.
My breathing was quite erratic as they continued to work my cock, it was like they were worshipping it like it was some divine being. Jacob moved to take the head of my dick in his mouth, working the magic that I used to love. Slowly he started taking more and more of me into his mouth until his face was buried in my pubes, the entire shaft in his mouth and lodged down his throat.
At the same time Ian moved a little lower. He was lapping at my balls, gently sucking them, the tongue piercing feeling like a special massager attached to his tongue. Just as Jacob took all of my cock in his mouth Ian sucked both of my balls into his and worked them with his tongue. It was so amazing. Not one bit of my cock or balls were exposed to the air, encased entirely in two hot mouths. I groaned and leaned back on the bed, gripping the sheets and willing myself not to explode.
Jacob rose up with a gasp, needing the air, but he had the biggest smile on his face.
“Damn, I forgot how good that cock feels deep in my throat. Fucking awesome!” he beamed.
He moved his lips to kiss up my body, taking the time to tongue my developing abs and my growing pecs. He nuzzled in against my neck, kissing and licking the soft skin. Then he pulled back, looked me straight in the eyes and leaned in for a passionate, tongue filled kiss.
“Fuck Matt! I didn’t think it was possible but you’re even hotter than when we were going out. Your body is incredible.” Jacob said before diving back in for another kiss.
With Jacob on top of me Ian took my cock back in his mouth, sucking me deep. Feeling the piercing in his tongue running around the head of my dick, traveling up and down the length of my shaft and even pushing in to my slit drove me wild.
Then it seemed as though he wanted to take advantage of having my eight inches in front of him because he slowly started to take more and more of me into his mouth, pushing lower. He gagged a few times and had to pull off to recover himself, but then he just went back down for more until my entire cock was buried in his mouth, his throat muscles dancing madly around the top two inches of my dick.
“Fuck, that big dick is amazing!” Ian screamed, finally pulling back. “I so need that inside me.”
“Not before me you don’t!” Jacob said in protest. “It’s been too long, Matt, I need you to fuck me like you always used to.”
I smiled and was about to move but Jacob put his hands on my chest and pushed me down to the bed. He leaned down and licked my ear before he whispered to me.
“No, stay there. I want to ride you first, then you can fuck the shit out of me.”
Jacob jumped off the bed, giving Ian a quick tongue filled kiss. He went into his bedside drawers and pulled out a box of condoms, throwing half a dozen on the bed. Ian chuckled, throwing Jacob some lube that had been over on the desk that was crammed into one corner of the room. I could tell they had done this before, maybe even with Scott, and that excited me even more. I was in for a treat.
Ian leaned forward, placing one hand on the bed as the other wrapped around my cock, slowly stroking me to keep me hard, not that it was needed. Jacob was smiling watching me lying on the bed just waiting for what was to come as he lubed up his fingers and moved them around to his ass, getting it ready for my dick.
Ian bent down further to swallow my dick, bobbing up and down on it, getting it nice and wet. He reached over and grabbed a condom, ripping open the wrapper and quickly rolling it down my shaft.
Jacob got on the bed and straddled me, placing his dick at my lips. It had been a long time since I had sucked his dick but I loved it as I sucked it in and started working it with my tongue, lapping up the sweet precum that I used to love drinking down.
As I continued to suck Jacob’s hot cock, which wasn’t as big as mine or as thick as Corey’s but was still a great size and shape, Ian slathered lube on his hands and my dick and started to make my covered shaft as slick as could be.
Jacob pulled his cock from my mouth and leaned down for a kiss as he backed his ass up and started rubbing it against my throbbing cock. I wanted to just drive my dick up inside him but I had no control with Jacob pinning me down and Ian holding my cock, guiding it up and down across Jacob’s pink hole.
I moaned in pleasure as Jacob moved again, pushing his ass down on my cock so it sank deep inside him. My cock passed the sphincter with ease and I knew he was getting fucked regularly, no doubt by Ian, his boyfriend and even Scott, or should I say Stacy, but as my cock pushed in deeper his ass began to tighten as my big dick reached depths most dicks couldn’t reach.
“Oh fuck!” Jacob screamed, sitting down on my whole cock, which was throbbing inside him. “You are so fucking big, Matt. Even bigger than I remember. Oh shit! You’re fucking me where no other guy has fucked me.”
Ian’s hands were all over Jacob’s ass, as well as rubbing my thighs and cupping my balls. Damn, it was hot, but it wasn’t what I wanted.
“Oh yeah, Jacob, ride my big dick with your tight ass. Fuck yourself like you’ve been wanting to for the last few years. Feel what you’ve been missing.” I groaned as Jacob started to move, pulling my cock out of his ass before sitting back down on it.
“Fuck!” Ian breathed. “Look at that big dick plugging that hole!”
“Get your beautiful pierced cock up here, Ian,” I smiled as I started to thrust up into Jacob and he continued to ride my cock. “I want to feel that PA against my tongue.”
Ian moved almost too fast for it to register, so eager to have my mouth around his cock. He hopped up onto the bed beside me, pressing his cock against my lips. I turned my head, opened my mouth and slipped the tip inside, feeling the cold metal against my tongue. It was the most exciting thing I’d ever felt.
“Fuck that’s hot,” Jacob said, watching as Ian pushed more of his cock into my mouth.
I was so hungry for Ian’s cock, running my tongue all over it as he fucked my face. I loved feeling the piercing against my tongue. Sucking a dick was great fun under any circumstances but having the piercing to play around with just sent it off the charts, rolling it around on my tongue, flicking it with the tip.
It wasn’t until Ian’s dick was in my mouth that I realised how big his cock was. I had become used to deep throating Corey’s thick cock, but as Ian pushed his dick further in my mouth and the piercing pushed against the sides of my throat, his dick wanting entry, I realised that he had almost an inch on Corey, his dick was at least seven inches and was really doing a number on my throat.
Jacob continued riding my cock the entire time, in fact, the deeper Ian’s dick sank into my mouth the harder Jacob seemed to ride me, building himself up into a sexual frenzy so he was bouncing up and down on my cock, our flesh slapping against each other.
Ian pulled his cock out of my mouth and bent down to shove his pierced tongue where his pierced cock had just been. The two felt so different but so similar at the same time. When Ian pulled back Jacob leaned down, mashing his lips against mine for a deep kiss as I grabbed his ass and started to fuck up into him harder.
Jacob was groaning into my mouth and started moving his hips back and forth. On one forward stroke he pulled off too far and my dick slipped out of him. I was just about to shove it back in to fuck him good when I felt Jacob’s weight shift and he fell off me onto the bed.
It took me a moment to realise that Ian has seized his opportunity and had pushed Jacob off me. Jacob looked upset as he turned to see what Ian was doing. His eyes went wide as Ian straddled me and sank his ass down on my dick in one swift move.
“HOLY FUCK!” All three of us screamed together.
Ian’s ass was so tight. I knew he must be more of a top than a bottom, but he was still incredibly skilled as a bottom because the second my dick was fully embedded in his ass he started working my cock with the muscle of his ass and had me moaning.
He slowly pulled up and started ridding me, moving his ass up and down, driving my cock deeper inside him. Seeing Jacob watching with a sad look on his face like he was being left out I reached over and handed him a condom. When he looked at me with confusion on his face, I winked and he seemed to understand.
“Good God, Matt. This is the biggest dick I’ve ever had inside me. So fucking good!” Ian moaned.
I smiled and sat up, wrapping my arms around Ian for a kiss. Holding onto him tightly I rolled us over so I could put him on his back. He wrapped his legs around my waist as I continued to kiss him and really started to pound him hard, fucking him deep.
With Ian moaning in my mouth I felt the bed move as Jacob moved behind me. My hips were moving backwards and forwards as I continued my hard thrusts into Ian’s ass, letting him feel all of my dick as it dove into his depths, stretching him wide.
Jacob’s hands found their way to my ass and he started to massage my cheeks before softly pulling them apart, burying his face in my crack to lick at my hole. It was amazing. I had never been rimmed while I fucked someone, it was such a new, yet exciting feeling. As I pulled my dick out of Ian’s hole it pushed my ass back onto Jacob’s face and his tongue started pushing inside me.
I was really starting to get into it, Ian holding on to me as I drilled his ass, staring into my eyes as he panted for breath, his rock hard cock dripping as it rubbed against my stomach.
Jacob’s face slowly pulled back only to be replaced by his lubed fingers that teased my hole at first and then sank inside, rubbing the walls of my ass and finding my spot which made me shriek and buck that much harder into Ian’s ass.
“Oh fuck,” I said, pushing Jacob off me and pulling my dick out of Ian’s well fucked ass. I lay down on my back and pulled my legs up, hooking them under my elbows, exposing my hole. “One of you needs to fuck me right now!”
Ian was still panting on the bed, trying to recover from the pounding I just gave him, so Jacob quickly ripped open the condom I had handed him, pulled it down his dick and with no hesitation whatsoever pushed it into my ass.
He was nowhere near as thick as Corey so his dick slid in with ease but it still felt so good. I was being fucked by a guy and a dick I never thought I would ever experience again. It was strangely thrilling.
“Oh damn, your ass feels so good, Matt. I didn’t get to fuck it anywhere near often enough,” Jacob said, fucking me hard, with short, deep thrusts.
“That’s cause you loved my big dick too much, you always had to be on the end of it,” I smiled.
“Hell yeah, I did.” Jacob smiled, replacing my hands behind my knees and pushing my legs back, lifting my ass off the bed so he could fuck me even harder, almost bending me in half.
I groaned in pure ecstasy as Jacob’s cock fucked me good. His dick felt so different to Corey’s but it was a good different. Jacob was the first guy other than Corey to fuck my ass since Scott almost a year ago. It was exhilarating and I couldn’t wait to feel Ian’s big pierced cock drilling me either.
I used the skills I’d learned from all the sex with Jacob and Corey to squeeze my ass, tightening it around Jacob’s cock, making him moan as he panted and continued to fuck my ass. I was trying to milk the cum out of him.
I turned my head and was going to tell Ian to shove his hot cock back in my mouth only to see him with a total look of lust in his eyes as he rolled a condom over his cock and started to lube it up.
Suddenly Jacob tensed up and screamed out as he came, pushing his dick as deep inside me as it would go, firing his shots into the condom as he leaned down and shoved his tongue in my mouth.
Slowly coming down from his orgasm, Jacob pulled back and lowered my ass down to the bed as he pulled his spent cock out of me. My back was aching slightly from the position I’d just been fucked in but there was nothing in the world that was going to stop me from feeling Ian’s hot cock inside me.
Once again he pushed Jacob out of the way and was smiling down at me as he leaned in for a kiss. He pushed my legs up slightly to wrap them around his waist and he rubbed the head of his dick against my hole. I moaned feeling it pressing at my entrance. I could feel the piercing through the condom, it felt so different but with every stroke the cock made over my hole I shivered and my dick jumped, leaking precum all over my stomach.
Softly and gently Ian started to push his way inside me. The piercing ran over my sphincter before being granted entry and I screamed out, my entire body shuddering. Fuck it felt so good!
Further and further inside me Ian pushed his cock, taking it slowly so that I could feel the piercing, along with the rest of his nice dick rub against the walls of my ass. I threw my head back, arched my back and screamed. My dick was throbbing so much I thought I might explode at any second without touching myself.
When Ian bottomed out he didn’t move, he leaned in for a kiss, pushing his tongue inside my mouth. I could feel both piercings in me at once, one pushing at my insides, the other running over my tongue.
After a minute or two, during which I’d started to run my hands all over his back and ass, Ian slowly started to move, pulling back almost all the way and then pushing back in. It was almost painfully slow as I felt the PA sliding against the walls of my ass, which involuntarily squeezed his cock, heightening the sensations more.
“Fuck me, Ian! Please, fuck me!” I panted, grabbing his ass to pull him deeper.
Ian smiled, moving his hips faster to really start fucking my ass. It felt so good. I almost didn’t want this to be the only time I felt his cock inside me. Maybe I would have to sneak back here with Scott some time so I could get fucked by it again. We continued to make out as he started to thrust harder into me, really making me feel his length.
My entire body started to shake and I felt so much pleasure surge through me. My chest was heaving and I found it hard to breath. His dick was rubbing over my prostate with the piercing catching it just right. I had never felt anything like it.
With my arms still clutching onto Ian I screamed into his mouth and my cock exploded harder than it ever had before, spraying the biggest load of my life between our bodies as he still thrust deep inside me, each forward movement causing more cum to spew from my dick.
When I couldn’t take any more, I pushed Ian off me, his cock leaving my body with a pop. With what little strength I had left I turned around on the bed, ripped the condom from Ian’s dick and swallowed his cock down.
Within thirty seconds of me working his hot dick with my tongue, the piercing teasing my throat again, he came hard, gripping the back of my head in his hand and flooding my mouth with his seed. I swallowed it down, loving the sweet yet salty taste. This guy was so good in so many ways.
Ian pulled his dick out of my mouth and collapsed on the bed next to Jacob who had barely recovered from his own orgasm.
It took me a moment to catch my own breath but when I did I rolled off the bed, using Jacob’s t-shirt to wipe the cum off my body. Finding my own clothes I got dressed. I walked to the bed, kissing first Ian and then Jacob, our tongues battling, before pulling back.
“I really have to go guys,” I said, “but this was amazing.”
“Maybe we can do this again?” Ian asked with hope in his voice.
“Maybe. It probably won’t be for a while, but never say never.” I smiled as I walked out of the bedroom, grabbed what I had left in the living area and left the apartment building.
Outside I realised Jacob had driven me to his place and I had no idea where I was, but just as I was about to go back inside I saw a bus approaching I had used a couple of times the year before that dropped me off right near campus, so I hopped on it, my ass feeling well and truly fucked when I sat down.
When I got off the bus I quickly made my way back onto campus and headed for my room. Nearing the dorm, Parker came running up to me…
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