The first week in the dorm had flown past, I was falling into a routine. My nightly rendezvous with Matt was earning me some freedoms that I enjoyed. Jacob was so far unaware I think but growing suspicious of why I was getting up to use the bathroom every night at 2 AM. Jacob hadn't mentioned the hand job I gave him on our first night together and I hadn't brought it up. I imagined he was struggling with the idea that he had allowed a boy to handle his cock. I let it alone, figuring he would talk about it if he wanted, or maybe if he wanted another hand job. He was however not any stealthier about jerking it which was happening with what seemed like increased regularity.
Classes were pretty easy and large, most of them being freshmen level intro into this and that. The one exception being calculus 1, which I was able to sign up for because I took college level algebra while in high school. Most of the kids in the class were upperclassman save myself and one 16 year old Indian kid named Niro. He was some sort of prodigy and loved to tout it. After our first quiz he was extremely put out that I made a 98 and he only made a 96. What can I say math makes sense to me.
I had started looking for work also. I applied at the coffee shop in the campus bookstore and a couple of restaurants around the school within walking distance. The burger shop called Sparkie's a couple of blocks from the dorm called first and I accepted the job as a cashier. Seemed easy enough, and it was close. It paid minimum wage but you got a share of the tip jar, and a free meal.
My first night went fine, I made a few dollars in tips scarfed down a double cheeseburger and some onion rings, and headed back to the dorm. When I got there it was about 10 o'clock and Jacob was already in the shower. I took my uniform off (just a polo style shirt) and dropped it in my dirty clothes hamper, I took off my pants and stood briefly in front of the full length mirror admiring my pink pantie clad derriere. The door opened suddenly and Jacob strolled in, immediately jumping into conversation as per usual.
“Hey there Sam, how was work? I just ate there the other day it was awesome I love their onion,” he paused eyeing me up and down. Seems he just noticed what I was wearing, very feminine pink cotton panties with white lace trim and a little flower embroidered on the waistband and a short form fitting white tank top undershirt, exposing my cute flat belly, “onion rings,” he continued.
“Dude...”he said.
“I... uh”
“Don't mind me I don't judge...” He stared at me for a moment. “ I mean if you are gay or something it's ok with me, or trans? Or whatever? I mean we did that thing … so obviously I am somewhere on the rainbow spectrum too I guess.”
“I wasn't going to bring it up if you didn't want to talk about it I totally understand.” I said.
“No no no it's cool I just you know didn't want you to think I was homophobic or whatever” He said looking down at his feet. He was just out of the shower wearing some slides and his plush blue shower robe, his sandy blonde locks damp and clinging to his face and neck.
“I'm not sure if gay is right... and I'm not a transgender person I mean I don't want to be a woman, but I have like this femme side that comes out sometimes... I like feminine things, and … looking in the mirror at myself … wearing...” I paused, “I'm just trying to figure it out I guess.”
“Yeah that's cool man I'm totally cool with it. Whatever, I mean, you just gotta find out who you are, we all do.” he reached down to adjust his obvious growing erection and started for the top bunk. I heard his laptop open and knew what was coming next.
“I'm gonna grab a shower, I smell like onion rings,” I took off Samantha's things and grabbed my robe out of my wardrobe and my shower kit and headed for the bathroom. I showered quickly, gave myself a quick enema to prepare for my late night with Matt, shaved myself clean, dried myself off and sat in the warm shower stall for a minute before throwing my robe back on and gathering my things. A couple of other kids were in the bathroom when I was leaving the shower and I heard one of them mutter, “Faggot,” under his breath while I was walking by.
“Don't you wish,” I said, turning my head to see him blush quickly and bow out his chest in some desperate show of machismo.
Suddenly he rushed over to me and before I could react, punched me in my face. The force of the blow knocked me down. I sprawled out on the bathroom tiles my eye stinging tears welling up from the sharp pain, “Wha... fuck,” I said.
His buddy laughing, the triumphant bully stood over me gloating “ Watch your mouth punk, next time I'll fuck you up good.” He stepped over me and walked out, his buddy spit at me when he walked by, luckily I was able to move enough out of the way that he missed.
I gathered myself and walked down the hall to my dorm room. When I entered the room was lit only by one lamp, and the sounds of Jacob pleasuring himself from the top bunk paused dramatically before resuming once I closed the door behind me. Not knowing what had come over me I dropped my shower supplies and nimbly scaled the ladder to Jacobs bunk and hopped into it with him. He was still in his robe which was flung open, reclined on a pile of pillows (I noted one of them was one of mine) with one leg upright and his and on his large cock. He looked startled but said nothing as I slid forward between his legs. I pushed his knee out of my way making him lean back and let go of his dick which I grabbed with both hands. I began stroking him with both hands twisting with the top hand as I reached the end of my stroke. He took in a breath sharply offering no resistance but still appearing shocked as I continued my methodical work. I breathed in the sweet smell of his cock reveling in its girth, its hardness. He leaned back on his elbows allowing me more room and I leaned down over him resting his cock head on my cheek. I slowly tilted my head as I stroked him until my slightly open lips touched the side of his erection, my tongue slightly touching its skin as I continued stroking now faster. I dropped my right hand to his balls wrapping my fingers around the top of his scrotum and pulling them tight. My left hand continued its motions stroking, twisting. I was now sucking gently on the side of his cock biting it ever so tenderly. Jacob was moaning loudly now and his hips were involuntarily rising in time with my strokes his pelvis meeting the base of my palm with a quiet thump. I was drunk with the smell of him, the taste of him and suddenly took his cocks large head into my mouth, it didn't fit well and I opened my mouth as wide as I could, feeling my jaw muscles stretch and my tongue pushed to the back of my mouth I felt his cock swell and pulsate and before I could react he was shooting his large load into my mouth I jerked back surprised and another jet of semen splashed across my face and in my hair. I turned my head only to be hit again and then again and yet more came out dripping down knuckles of my left hand as I continued to squeeze and stroke him. His laptop was still open and I noticed he was browsing through some femboy porn on Xgerble, a video was open of some twink wearing pink panties and thigh high rainbow striped stockings with a tiny tank top barely covering his boyish nipples, he was sticking his chest out and pinching his nipples, moaning in a most effeminate manner.
“You want to meet someone like that?” I said gathering the corner of his robe to wipe off my face still dripping with his cum.
“Like who,” he started then hastily shutting his laptop. “I mean, hehe you know how porn goes you're browsing around and all the sudden your roommate jumps up and then...”
“I told you I have a feminine side right? Her name is Sam too... Samantha... you want me to show you? Would you like to meet... her” I asked. Samantha was already driving at this point my face was taking on her sultry mannerisms I bit my lower lip. Still tasting his semen.
I arched my back sticking my ass in the air and pushing myself back like a cat backing up. Jacob said nothing, he gulped loudly as I hopped down from the top bunk and began rummaging around in my alternative clothes. I found a long pair of socks, thigh high and yellow with little flowers around the hem, I took out a matching yellow tank top short and low cut with spaghetti straps and a black thong, which was about 2 sizes too small. My cock was hard but it tucked nicely inside the waistband, bulging outline plain to see under the stretchy soft material of the trim black panties. Framing the 5 inch hard cock were my two small balls, pushed tightly against my body. I hastily threw on some eyeliner and lipstick, a dark shade of brownish red, smacking my lips together and looked up to see Jacob looking at me in wonderment.
I spun around in the most feminine way I could stopping with my back towards Jacob, poking my ass out and crossing my legs. I stood on my toes and leaned over on the desk looking over my shoulder at Jacob seductively again biting my lip and throwing as much sex appeal at him as I could muster. My hair was still damp from the shower and I shook my head throwing it around, strands were stuck to my face and neck. I threw my head forward and to the side and my auburn locks flipped over to one side of my head exposing the side of my neck (one of my better features I'd always thought). Standing up straight I parted my legs slightly and reached behind me grabbing my ass with both hands and pulling my ass cheeks apart the black thong had disappeared between them but now scarcely covered my puckered pink asshole.
I was grinding my cock against the desk when I heard Jacob slide down from the top bunk behind me. “You like it cowboy?” Samantha said now firmly at the reigns. I looked back Jacob was walking towards me.
“You're so fucking hot” he said.. “Can I..”
I didn't wait for the rest of his question instead pushing my ass against him his hard cock resting between my cheeks. I stood up my back against his bare chest and reached over my shoulder and took the back of his head with my hand guiding it down to my neck where he began to nibble and suckle causing me an ecstatic tingling sensation that rocked me from head to toe. His monstrous cock was sliding up and down my ass crack he reached down pulling my panties over it. He was leaking precum all over my ass and lower back and soon I was slick with it. His kisses on my neck were becoming more frantic as his hands became more active rubbing me all over.. my stomach, under my tank top, my breasts. His left hand moved up to my throat, under my chin he tilted my head to the side offering himself more access to the side of my neck, which he was now ravaging. His right hand had drifted down to the top of my panties, clumsily fumbling with my now painfully hard cock. I gasped as he found a hold of it rubbing it gently through soft material. He was rhythmically grinding his cock through my thong between my cheeks now and each time his cock head passed my asshole it sent a jolt of pleasure through my body. As his large cock slid between my cheeks his balls would pop against the bottom of my butt with a 'PAP'. He reached down with both hands grabbing the sides of my hips now abandoning my saliva soaked neck and was wholeheartedly humping my ass cheeks. I was pushing back to meet his thrusts and leaned forward over the desk I turned slightly and put my hand on his chest. Each thrust his huge cock head wad pushing past my anus and lubing it more and more with his juices. I began to be somewhat afraid that it was going to slide in and destroy me. My own cock was pushing against the desk and was somewhat pained but I was trapped now holding on for dear life as Jacob bashed his cock against my backside.
“Oh god Oh god Ohhhhhh gggaaah” he said and I could feel his already massive dick expand even further the head of his cock seemed like a baseball and he suddenly tensed up and his giant cock began spraying cum for the second time. It jetted up my back and between my cheeks and he didn't stop pumping his cock back and forth until the last streams of it were dripping from the end of it. He pulled his dick from under my thong and smacked it on my ass a couple of times. Still wearing his robe he used it to wipe his cum from my back as I purred still rubbing my ass against him. When he had cleaned much of it up I turned around now facing him as Samantha for the first time. I was looking up at him through my long lashes, with my face tilted down, biting my lower lip. I sat on the desk pushing myself back slightly and spreading my legs, rubbing my still hard cock through my panties. I reached down with my other hand and grabbed his softening (but still rather hard... and big) cock, I squeezed it until more of his juices came out, popping my cum laden fingers into my mouth sucking them clean. He stepped forward between my legs and bent down his lips inches from mine. I threw my free arm around his neck pulling his face to mine and kissing him boldly on the mouth. Our lips parted his tongue darting into my mouth and licking my teeth. I bit his tongue and then his lip. We kissed and caressed each other passionately. I now had my cock in my hand stroking frantically and let go of Jacob to lean back on the desktop, knocking off some books and papers. I was looking into his eyes stroking my cock and I wrapped my legs around him. He was holding my legs with his hands as I stroked my cock pulling me towards him his still half hard dick pressed against my perineum. My breathing became ragged as I approached my climax and what I thought to be impossible began to happen. Jacobs cock was getting hard again. Its hardening length was pushing its way beneath me. He reached behind me grabbing my ass and pulling me tighter to him I was moaning as I began to feel my orgasm grow. His strong hands were tight on my ass now and his cock was seemingly back to full mast, its large head under my ass with only the strip of thong material between him and my anus.
“FUCK ME” Samantha's sultry voice came from nowhere. I Wrapped my legs tighter around him and he lifted me up from the desk enough that he could squarely line up his cock on my asshole his wandering fingers pulled my thong out of the way. I relaxed my anus and pushed down on him. The world seemed to stop and my anus slowly expanded until I thought it would rip apart. “UNGHHH” I cried in pain. My eyes were watering with it my head was light and my vision blurred, and suddenly with a pop he was inside of me.
“OH MY GAWD” he moaned as his cock entered me, slowly he began to fuck me. The pain I had felt before was now completely replaced by the most intense pleasure I had ever known. I had forgotten my aching cock but now leaned back across the desk and started stroking it again while Jacob pushed slowly into me. As his rhythm picked up I began to stroke faster, pushing myself to the brink of orgasm and letting go. He was now pounding my ass, his large balls thudding against me his teeth were gritted in concentration. Jacob reached between us grabbing my cock suddenly alternately stroking it and pulling it like a handle he was using to pull me onto his cock. and just a few short seconds of this pushed me over the edge I began to cum and he held onto my cock spurts of cum pouring out over his clenched fist. As I came my anus tightened around his hard cock causing me more pleasure, more pain and pushing him to his third orgasm of the night. My heels locked behind his knees pulling him into me as his cock burst inside of me spilling his depleted load into me. I was clinging to him spent, exhausted. He was still slowly pushing his cock inside of me as it continued its last feeble spasms. He looked down at me and said, “woah, I think that's the best fuck I've ever had.”
“I've never felt anything like that...” I said trailing off as I caught my breath.
He pulled out of me, sending me again into shivers as his big member passed my prostate and popped past my twitching anus. Jacob literally fell backwards into my desk chair rolling it back towards the bunk beds head lolling behind him.
“I can't believe you manage to cum so much, it's unnatural,” I was leaning back on the desk letting the cum drip from my ass. I heard some of it hit the floor, splat. “It's those big balls.”
“I can't believe how sexy you are when you dress up like that, your legs are so sexy and smooth and your ass … way better than any of those femboys online. Samantha is sex appeal personified...You should have a live stream you'd make mint.”
I laughed “that'd be something...” I said, at first dismissively, but Samantha's wheels were already turning. I took a towel and cleaned up the cum and sweat smeared across my desk, and took a look in the mirror, touching up my lipstick a bit, and wiping my face
“O M G” Jacob abbreviated, “my world is rocked, I am going to sleep like the dead,” he said climbing into his bunk and plopping down on his pillow with a ploof.
“I've gotta get cleaned up” I said, but I knew I had other obligations.
I threw a robe on over my ruffled tank top, pulled up my stockings and straightened my thong. My robe had a hood which was why I bought it. I threw the hood over my head to hide my smeared lipstick and headed out into the dormitory hallway. I wasn't going to the bathroom however, I strode down the hall, limping slightly from the aching asshole my roommate had left me with, to room 1001... Matt's room. I knocked lightly and soon heard him unlocking the door.
“Was wondering if you were going to make it tonight” he said standing there in only his boxers. He looked down the hall briefly, and let me in.
I turned to face him slowly dropping the hood of my robe and letting it slide off my shoulders to the floor.
“Hey there cowboy, “ Samantha purred. “I hope you're happy to see me.” I turned my back to him and he came up behind me, sliding his hand around my front, pushing it under my lemon tank top and grabbing my breast roughly.
“WOW!, You dressed all the way up for me tonight” he said and I could feel his cock pressing against my ass. I decided then that I didn't need my sore ass to be fucked again so I turned around and dropped to my knees in front of him. I unbuttoned the front of his boxers and his cock sprung out at me like a jack-in-the-box. I stared up at him as I began stroking it. “Yeah, you little minx... sexy.” he said, as I brought his dick to life.
For the first time I really noticed how sexy his body was, his tight abs and toned obliques framed his neatly trimmed pubic area. His beautifully veined seven inch cock now very erect, was clean and smelled incredibly enticing. His shaved balls hung heavily between his legs, drawing up slightly as I pulled on his penis, stroking it slowly. I looked up at him through my long lashes and fondled his smooth testicles. I started licking the sides of his dick and kissing it with my mouth open. Sucking on the sides while I rubbed the tip and caressed his balls. He was moaning now. I put both hands to work on his shaft now.
“Want me to suck it for you baby?” Samantha's voice oozed out of my mouth like honey. “Want me to swallow your big load baby boy?”
“God yes” he whispered now putty in my hands.
I turned my attention back to his dick, licking the tip clean of precum and began to take it into my mouth. I found it easier to handle than Jacob's monster bobbing my head down further each time until I could feel his cock beginning to hit the back of my throat. He was now starting to thrust into my mouth and he reached down and grabbed my hair on either side of my head like pig tails. I gagged a bit as he passed his cock into my throat his balls parted at my chin. I was holding on to his ass as he fucked my face in a way that wasn't exactly pleasurable. I felt somewhere between suffocation and drowning on my own saliva. Spit and drool was pouring out of me. My eyes began to water and he kept on going... I felt like I might puke so I shoved him back his cock exiting my mouth with a gag. I took a deep breath and coughed a bit. “ Alright you fucker,” Samantha cursed “Easy.”
He relaxed his grip on my hair some and I grabbed his cock by the base, diving back onto it taking it all the way to the base, my gag reflex now conquered, I began sucking his cock with renewed vigor. Slurping and sucking twisting my hand around his dick, fingering his ass and playing with his balls. It didn't take long before I felt his cock expand and he groaned loudly and began cumming down my throat. Holding my head in place with his hands as he spilled his seed into me. He held me there until he was finished and I pulled off of him with a gasp and looked up through blurry tear filled eyes. His eyes were closed and his head was tilted back mouth hanging open as he moaned and groaned. His hard cock was still twitching, another lumpy drip of semen hung briefly from the end of it and I licked it away, causing him to twitch involuntarily.
I stood slowly sliding my body against his, reaching behind him and squeezing his ass. I leaned forward a bit and gave him a peck on the lips, just a little kiss and smiled at him. He was still breathing hard and looking at me with an odd look, pensive, almost caring. He reached up and took my chin with an unusual tenderness turning my head to the side.
“Where'd you get that shiner?” he asked.
I looked behind him to the full length mirror on his wall to see Samantha's face poking around his muscular shoulder, lipstick smeared and eye liner running down her bruised cheek. There was a dark crease beneath her lower left eyelid, and a splotch of bright red in the white of that same eye. “Some asshole hit me in the shower,” I said reaching up to touch the tender bruise. Suddenly reliving the incident I felt tears welling up.
“Who was it I'll have a word with him,” he said.
“I don't know just some dickhead, it's fine,” I was sure I'd see him again and didn't want to make the situation worse. “I doubt he'll bother me again.”
For a second Matt didn't say anything, but his usual gruff and impatient temperament seemed to fade as he looked me up and down. “Hey look I know what its like being bullied and wanting to handle your own business. I've been into Tae Kwon Do since I was thirteen, I'm a black belt. Our dojo is small and classes are cheap if your interested, its on University drive and ninth avenue. If you want to come check it out we'll teach you how to protect yourself,” he touched my bruised cheek with the back of his hand gently his face scrunched into a disapproving scowl. “And if you change your mind, just give me a name and I promise you he will never come near you again.” His expression turned back to his normal cold hardness, and he smacked my ass playfully, “now get outta here, I gotta finish this essay.”
I made my way to the shower and cleaned myself up, and back to my room slipping into the darkness. I tiptoed to the bed, and sat down on my bunk for a moment. Sighing and wiping away a sudden tear, I got up and climbed onto the top bunk. Jacob was snoring lightly and I crawled up next to him and buried myself under his arm, snuggling my back against his warmth and sliding quickly into a deep exhausted sleep.