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Preston - The Lit TA
🕑 Added 2024-01-12 05:01:01 +0000 UTCWhen you’re confident and good-looking, you can pretty much get away with anything. I’m both of those things. I grew up with adults telling me how good-looking I am, and how handsome I’ll be when I “get older.” I had a few run-ins with adults who found me a little too attractive, nothing traumatizing, but certainly inappropriate.
As a teen in a Colorado high school, I knew I was gay, but in 1998 with what happened to Matthew Shephard, there was no way I was coming out or even going to risk people finding out I was gay. So I did what I believe most of us did, I hid in plain sight, dated one girl after another, and got a reputation for being a player, to the point where most girls didn’t want to date me anymore. Oh no…what a shame. Don’t worry, I’m not a dick I just didn’t want to find myself in a situation where I had to explain why my dick didn’t get hard for any of the cheerleaders who by all standards were more than reasonably attractive, I just wasn’t attracted to them.
After graduation in the spring of 1999, I moved to California and went to UCLA that fall. No particular major in mind, but my parents insisted I go to college. I guess it’s important to understand that I grew up with money, my mother’s family has a lot of money from oil and my father has his own fortune from a few generations of investing in the markets. We live in Colorado because my mother loves to ski as often as possible and it’s not a hardship for either of them to travel to Denver for work when they do work. Needless to say, I recognize I come from a place of privilege.
Most kids get the speech about safe sex as a teen for the sake of not getting a girl pregnant and “ruining your life,” but my dad gave me the safe sex speech so that “a woman doesn’t get pregnant on purpose as a meal ticket.” While the idea of having sex with a woman makes me cringe, my takeaway was you can’t trust people when it comes to sex.
I lost my virginity in the second week of college. It was actually kind of sweet, it was with a boy in an acting class I was taking for fun and to piss off my parents. I think most of the guys in that class were gay, some more obvious than others, but Clinton and I were in his dorm rehearsing some lines, one thing led to another and I popped his cherry. While I wasn’t prepared for that to happen, he had condoms and lube on the ready so that was lucky.
After that, my gaydar kicked in. Maybe it was always there, but I started noticing guys noticing me in a way I hadn’t before. Like I said before, I’m a good-looking guy, 6’1”, with shorter sandy blonde hair with frosted tips, 165 pounds nicely toned, I’m not an athlete per se, but I get my exercise doing activities like snowboarding on the weekends, horseback riding, hiking, swimming, outdoor activities that most people only do once a year I would do as often as possible. I ate well, and my mom would never allow junk food in the house because she had no impulse control so my dad and I suffered the consequences…and reaped the rewards because dad was pretty fit too for a man of 50 years old.
With great power comes great responsibility though. As I noticed I was turning heads, my hormones kicked into overdrive and I had to be prepared. I kept condoms and to-go lube on me and started hooking up with guys as often as possible. I had two rules; always top, and always safe. I had no interest in bottoming, I just didn’t see the appeal, and since PrEP was not a thing in the 90’s, you better believe I had no interest in unsafe sex.
I think by the time Halloween rolled around I already had a body count that was giving me a reputation. In LA there were a few areas a gay guy could go to guarantee sex. Not that I needed to go, after I popped Clinton’s cherry it got around pretty quickly that I was a top packing a 7” thick cut dick and guys were all for it. But every now and then if I found myself in the neighborhood there were a few venues I could pop into and to get my dick sucked pretty quickly and get out. When you look like a model and drive a BMW at my age people just let you into clubs. I always tip accordingly though.
This was all fun until one night I accidentally met one of my TA’s in a backroom at a gay bar in WeHo. I was already in the back, my pants undone, underwear under my balls, dick being sucked by a hot guy in a suit in his mid thirties I would guess. I had a hand on the back of his head, pumping my cock into his throat, not giving a shit if he could breath, just trying to dump some cum into his throat and get back to my apartment to study for an exam. Deeper into the darkness of the room I heard a guy groan and he said he was about to cum, the voice was familiar but I was too far into my on pleasure to really think much of it.
I was on the precipice of unloading my balls, when I heard the other guy deeper in the room groan and unload, which turned me on a bit more and I started really fucking this older guys face. My balls slapping on his chin, my orgasm was right there rippling under the surface. Out of the darkness I saw a cute pale guy around my age stumbling toward me, pulling up his pants over his white briefs, his dark hair framed his face as it fell haphazardly down on his soft skin. As he stumbled by he made eye contact with me and it hit me, he’s the TA for my creative writing class, Daniel…something, he grinned at me and looked down at my dick slowly going in and out of some strangers mouth and it pushed me over the edge.
“Oh fuck,” I lost my rhythm, and my orgasm boiled over, cum squirting into this guys mouth without even asking if he wanted to swallow, I couldn’t help it, like a faucet that broke I emptied my balls and to this guys credit he managed to swallow most of my cum without choking but I think I pushed a little too far into his throat and he gagged at the end. Daniel just smiled and walked out, still fixing his pants.
I nervously tucked my dick back into my boxers and was rushing out of the back room before I even finished zipping up. I scanned the room and didn’t see him at the bar. He wasn’t on the dance floor either. I rushed outside to see if maybe I could catch him leaving. He wasn’t anywhere.
I’m not out so I’m picky about who knows I like guys. I really don’t want it to get around the faculty because the professors are great resources for work references after you graduate. I know money is not a problem, but because of that my parents are well-connected and something like a rumor about me being seen in the back room of a gay club is the kind of thing that will spread like wildfire. I love my parents, but they are not very open-minded when it comes to “the gays.” A rumor like that would raise a lot of questions and I was just not ready to answer them.
Next time I was in class with Daniel as the TA, I was incredibly distracted. I looked at him differently. Almost like a Clark Kent vs Superman, in class he was dressed in clothes that were slightly outdated and didn’t fit him well, his hair was comed neatly and he had a shyness about him. At the club, in the dark room he was disheveled, his hair was dropping down into his face, his shirt was unbuttoned and his undershirt clung to his skinny body showing off his thing frame. Here in the classroom I couldn’t see the brief lines in his khakis and from the way his bulge moved I would guess he was wearing boxers. He’s all buttoned up in his matching shirt and sweater vest, both slightly too big for the thin body that I know is hidden underneath. He’s taller in the back room too, I don’t know how, but down at the bottom of the lecture hall sitting at the desk he looks like he’s barely 5 foot, but in the back room he was eye level and I was standing on my tippy toes as I was about to unload in that guys mouth.
I felt myself getting hard and had to remind myself that Daniel is the TA in my class and not a conquest. I realized he noticed me staring at him and I did my best to refocus on the professor. I needed to get a one on one conversation with him to make sure he keeps what he saw the other night to himself. Thankfully, the syllabus they handed out at the beginning of the year had a phone number for both the professor and TA’s should we need extra help or something, this was definitely an “or something.”
When class was over I saw him head towards the offices, so I rushed home to find the syllabus and give him a call.
“This is Daniel,” he answered.
“Uh, hey, Daniel, this is Preston from the Tuesday Thursday 12pm Lit class” I tried to keep my voice calm. I hadn’t rehearsed what I wanted to say and while I’m usually very confident, this was a first time for me to have such an awkward conversation with someone who could ruin my life.
“Yes, how can I help you?” He asked, very dry and monotone.
“Oh, ummm,” shit…I should’ve given this more thought.
“Hello?”
“Sorry, yes, umm, I was actually kind of hoping we could talk about friday night?” I just went for it.
There was a pause, I could hear him cover the phone and some movement, “I’m listening.”
“Well, I just wanted to make sure that, well, that my being there, in that particular state of…wel,l I don’t want rumors to be spread about me,” I struggled and exhaled deeply.
Another pause, “you’re afraid I’m going to tell the staff that I was drunk and high in the back room at a gay club, and when I was finished hooking up with a guy I saw you in the back room…at a gay club, getting your dick sucked by another guy?”
Fuck. The tone in his voice made me feel so stupid and pathetic. “Uh, kind of.”
“Preston, your secret is safe with me. Don’t Ask, Don’t Tell, Is not just a policy in the miltary,” Daniel joked.
This set me at ease. “Well, thanks, man, I really appreciate that.”
“Is there anything else I can do for you?” He asked, putting his professional voice back on like a hat.
I had a quick flash of his sexy lips, he had dick-sucking lips and the idea of him sucking my dick made my dick twitch in my pants. I shook my head, “Oh, no, I think that was it, thank you.”
“It’s no trouble, I’ll see you in class Thursday,” he ended the call.
He handled that in an incredibly mature way, I thought to myself. Granted, he was probably 3 years older than me, but this wasn’t an age thing as much as he was generally more mature than most college guys I had met.
Thursday came, I went to class and I almost exclusively paid attention to Daniel. Mentally picking him apart piece by piece. I noticed how fake this version of him was, almost like he was wearing a costume. He’s not this uptight bookworm, he’s the kind of guy who gets fucked up and gets off with other guys in a dark backroom. I started picturing what he would look like completely naked, sucking my dick with those soft pink lips, wondering if he likes to get fucked or if he’s the type that wants a gentle love-making session, either way I’ll bet his ass is tight. I shift my hips in my chair so I could cross my legs and hide my erection.
At some point Daniel got up and started handing out copies of a short story the professor wanted us to read and then do a writeup about before next class. When he passed me one I accidentally, or at least I think accidentally, grazed his hand with mine and I jerked my hand back like I touched a hot stove, then looked up where my eyes met his and he smiled with a knowing look in his eyes, then pushed the stapled papers towards me to grab. I felt my face get flush, and I wanted to die. I’ve never in my life had someone put me on edge like he does and it’s a disturbing feeling.
I packed my bag and was out the door as quickly as possible.
My parents purchased a condo for me not far from campus but on what they called “the better side” of the area. There were not many students who could afford to live off campus by themselves, definitely not any that I knew of that lived near me. Around the corner from my building was a new Starbucks that I liked to go to to study. It was great to read my lines for my acting class or in this case read the Metamorphoses assignment for my Lit class.
I was just on the last paragraph when I heard a familiar voice, “it’s almost like no one cared.”
I looked up from my reading, my eyes meeting with Daniel’s, “what?”
“You’re reading Metamorphoses right? The reading assignment?” He asked.
“Oh, yeah,” I shook my head, “It’s better than I expected, I can see why he assigned it.”
There was an awkward pause. I looked him up and down, he was no longer in his khakis and all buttoned up, he must have gone home and changed out of Clark Kent and into Superman. He was wearing a long-sleeve thermal shirt under a Green Day t-shirt, his hair no longer gelled slick but falling down to the sides haphazardly, he wasn’t even wearing his glasses. Honestly, he looked sexy as hell, and I was right, he is taller in real life, at least 6 foot.
“Do you want to sit?” I asked before I remembered he’s the TA and not some guy I just met at the coffee shop like a Meg Ryan movie.
“Oh, I,” he looked at his watch with a squint, “I can probably sit for a minute but I am supposed to be somewhere soon.”
I pushed the chair out from under the table with my foot and he sat down.
Another awkward pause, I felt his eyes roaming over me and it made me hot, knowing he was checking me out as a sexual object and not some kind of acedemic competition or something.
“You, live around here?” I asked, closing the packet of paper and giving him my full attention, somewhat undressing him with my eyes. Which is not my fault, his thermal shirt hugged his body and I could see the outlines of his skinny-guy muscles.
He let out a huff of air, “Yeah right, I think only celebrities and CEO’s can live over hear,” he took a sip of his coffee, his head bobbing up and down in the air.
I let the statement hang in the air for a second and nodded my head with him. Then I watched him lick the coffee off his bottom lip before he spoke again.
“You live around here, don’t you,” he smiled and shook his head.
“I live upstairs,” I grinned at him.
“Ugh, so lucky, I’m on the other side of campus, well off campus, I share an apartment with three other guys and rent is more disgusting than the bathroom,” he laughed at his own joke, and instinctively went to push up his glasses that he wasn’t wearing like a phantom tick.
Wow, he was cute.
“You look different, out of class and,” I took a pregnant pause, “and in the light.” I felt the need to add, to remind him that I saw him in the dark room, as if either of us had forgotten, but as some kind of mental fuckery that I did with other guys when I was trying to rattle them and get them into my bed. I couldn’t turn it off.
He raked his fingers through his hair, brushing it back out of his face and it pretty much dropped right back down, naturally parting in down the middle. “Oh, well, it’s required that we dress business casual while in the classroom,” he offered.
“And you’re not wearing your glasses?” I asked.
“Yeah,” he huffed, “when I go out I try to wear contacts, I’ve had my glasses broken too many times when out at night and I need them when in the classroom grading papers and stuff.” He blushed and took another sip of his coffee.
“Going out on a school night?” I asked.
His body language changed, he sat up straight, “I don’t have classes on Fridays, so I’m allowed.”
I flashed my perfectly straight teeth in a wide grin, “yeah, I set my schedule so I only have one afternoon class on Fridays.”
He looked me up and down one last time, then looked at his watch, “well, I have to get going, I’ll see you around,” he winked and stood up.
“See ya,” I smiled and watched as he walked out with a little pep in his step.
I watched as he left the coffee shop and walked south down the street. That wasn’t the direction back towards campus, but about ten blocks that way and another two east and there was a gay bar that I had never bothered to go in because it was too close to home. He wasn’t likely going there though, it was expensive.
I tried to focus on my studies, finished the last page of the required reading and decided to go back upstairs.
I couldn’t get Daniel out of my head so I took a cold shower, and when that didn’t help I decided I would jerk off and call it a night.
I was laying there on my bed going to town on my dick, rubbing my nipple with the other hand, imagining what Daniel could do with his mouth and those perfect lips, fuck what would I give to just taste him right now. That’s when it hit me, I could go to the bar and “bump into him” if he’s there. It seems almost stalker-level, but in this state of horniness, it sounded like a good idea.
I quickly dressed in my best clubbing outfit, and grabbed some cash from the “fun drawer.” I grabbed some condoms and to-go lube and shoved them in my pockets too.
Ten minutes later I was walking up to the club, the entrance was subtle, not speakeasy subtle, but you do kind of need to know it’s there otherwise it would come across as a service entrance.
I had my fake ID with me, but when you have a pretty face and look like you have money you don’t get carded. I slipped the guy a $20 bill anyway.
Walking in the place was pretty packed, dimly lit, with colored lights moving and twinkling from every corner, the music was kicking and people were dancing half-dressed on the dance floor. I went to the bar and ordered a Jack and Coke.
I sipped my drink as I watched the room, looking to see if I recognized anyone and trying not to look like I was looking for Daniel. Unsure of what I would say if I did see him.
“You look new,” a voice came from behind me.
I turned to see a guy that could be in his early thirties, probably 5’8”, salt and pepper hair cut short, decent build showing through his mesh t-shirt.
“I am new here, but not new,” I winked.
He looked me up and down, then took a sip from his drink. “Do you dance?”
I chugged my drink and set it back down on the bar, “why else would I be here?”
I followed him out to the dance floor where we immediately started grinding against each other to Deejay Alice’s “Better Off Alone” with some sick beats from the DJ. This guy had some moves and managed to grind his ass on my dick enough to make me regret having started jerking at home, I was glad I put on a pair of black CK briefs that would hide my erection better than boxers, but he definitely felt it even at half-mast.
When the song was over he pulled me through the crowd to the far side of the room, pushed me against the wall, and started to make out with me. I could taste alcohol and weed on his breath, but he was being aggressive and I liked it. His hands were roaming all over my body and I could tell he liked it, especially when he grinds his dick into mine I felt him smile through our kiss.
“Let’s go in the back,” he pulled me with him and led me down a dark narrow hallway into a musty dark room where you could hear moans and sex noises. A red light in the far corner barely kissed the edges of sweat-covered skin, but you could see fairly well if you let your eyes adjust.
He pushed me against the wall and immediately dropped to his knees, unbuttoning my jeans and pulling my dick out of my briefs, before he even had my balls out he had the head in his mouth and was sucking it like I had a gun to his head. I put my hands on the back of his head and gently thrust forward, his throat opened without hesitation and I was able to push in until my trimmed pubes were brushing against his nose.
“That’s it, suck my fucking dick,” I heard myself grumble.
The drink I chugged was going to my head as I slowly used my dick to cut off this guy's air supply, fuck this all felt good. I closed my eyes and imagined Daniel on his knees sucking my dick and starting to rock small thrusts into his mouth.
“That’s it, don’t stop,” it felt really good. He swallowed around my dick and managed to get enough air to not pass out every time I pulled out and thrust balls deep again, his throat muscles were like a wet fist jerking me off, I wasn’t going to last long.
“Fuck, you’re gonna make me cum,” I warned in an almost whisper.
I felt his hands slide up the legholes of my briefs to cup my ass and pull me deeper into his throat. That did it, my balls tightened and the orgasm I started back in my apartment shot out of my nuts and into his throat as I growled and held his head tight to my body. Twitching and jerking as rope after rope of my hot cum went into his throat, I slowly pulled out to let him breathe and make sure he got a shot of my load on his tongue and would taste me for the rest of the night.
He swallowed and cleaned my dick off with his tongue. I tucked myself away and pulled him up, I kissed him again, tasting myself in his mouth, “You want me to suck you?” I asked like a gentleman.
He kissed me back with a little heat and then broke the kiss, “No baby, I just wanted to taste you,” he smiled and pulled me back out of the dark room.
He bought us a round of shots and then he went back to the dancefloor. Now that I had cum I was feeling weird being here with no one to talk to. The bartender brought me over another shot, then pointed to the other end of the bar, of course, it was Daniel. He waved and smiled. I lifted the shot as if to say, “Cheers,” and tossed it down my throat.
He fought his way through the growing crowd and tucked in close to me at the bar.
“I’m starting to think you’re following me,” he yelled over the music, getting close enough to my ear that I felt some spittle from his words.
I laughed, “Maybe I am,” I winked.
“Can I buy you a drink?” He asked.
“Jack and Cocke,” I said.
He scoffed, “of course.”
He waved the bartender over, “Let me get a gin and tonic and a Jack and Coke for my friend,” he shouted.
“And another round of shots, on me,” I added.
“I didn’t expect to see you here,” his smile became a bit devilish.
“I live down the street,” I laughed.
“Still, I would’ve thought after your phone call I wouldn’t see you in public again, definitely not at a place like this,” he guestured broadly to the room.
The bar tender brought over our drinks.
“What can I say,” I gently licked my lips, “at this time of night I’m a different person.”
He picked up his shot and handed me mine, “I hope so,” he smiled, clinked his glass to mine and drank it like it was water.
“You look good, in this light, like a pretty butterfly fresh from his cocoon,” he commented on my club clothing then sipped his drink.
“Yeah, during the day I’m Preston,” I straightened my posture and mimed tightening my necktie that I wasn’t wearing. “At night,” I pulled slowly pulled off my shirt and tossed it to him, “I’m Preston,” I slowly let my hand glide down my chest to my adonis belt, then leaned on the bar in the sexiest way I could.
The look on his face as his eyes traveld down my naked torso to the waistband of my underwear and hopefully he was imagining what my dick looked like. I took a sip of my drink.
He thrust my shirt back at me, I could tell he was a little tipsy, his face flushed and he didn’t bring his eyes back up to meet mine, “this is probably inappropriate.” His body language changed and he turned back to the bar to take a long swig of his drink.
I’ve never had a guy turn me down like that before, it turned me on. I could tell he wanted me, but his restraint was sexy as hell. I quickly chugged my drink and slammed it back on the bar.
“Yeah, it’s a good thing these walls have a strict D.A.D.T. policy,” I pushed my shirt into his hands and walked to the dance floor.
I started dancing by myself as the DJ started a club mix of Madonna’s “Ray of Light” and the lazers and fog kicked in. I was really feeling it too, the heat of the room, the bass pounding through my body, I closed my eyes and just enjoyed the moment. Even more as I felt the alcohol doing it’s thing and I felt myself loosen up, swinging my hips a bit as my pants swung low and the waistband of my underwear caught in the flashes of light. I suddenly felt arms up over my shoulders and felt the waffle material of a longsleeve thermal shirt on my skin, the sweet sound of Daniels voice singing along with Madonna in my ear as his crotch inched closer and started grinding against my ass as we danced in this green lazer ray of light.
His hot breath on my ear as he continued to sing along, my sweaty body rubbing against his t-shirt, the growing bulge in his jeans pressing tighter on my ass. I raised my arms higher as I swayed to the music, his hands slowly dropped down my body, feeling their way to my hips and around my waist, pulling me tighter into him.
I rocked my hips with his, “And I feel!” we both sang along, “And I feeeeeel!” our hips started gyrating, I could feel his bulge prominently betwen my ass cheeks even with all the cloth between us as he led the way, his one hand on my hip and the other feeling it’s way up my chest, I swear he was taller than me now, his chin leaning down onto my shoulder, his hand came up and he ran his fingers through my hair before he gripped it in a tight fist pulling my head back, he whispered in my ear, “for the call of thunder threatens everyone.” Our hips gyrated as we dropped a little lower, not an inch between our bodies, “And I feel!” We both shouted and then he licked my ear, then licked my neck and gently bit my neck like he was going to suck my blood, I just moaned and leaned into him.
I spun myself around and kissed him, not skipping a beat as our crotches ground together, I could feel his dick through his jeans and he mine. His one hand held the back of my head as the other traced it’s way down my spine and dipped into my underwear and his middle finger saught out my sweaty hole like a heat seaking missile and gently rubbed. I felt a sensation run through my body I had never felt before, it went from my pucker through the deepest parts of my body up to my chest and tingled. I moaned into his mouth and he just pressed harder. My virginal pucker didn’t give way though.
He broke our kiss, “want to get out of here?”
I nodded my head yes. He pulled my shirt from the back of his jeans and handed it to me.
We walked over to the bar, he whispered something to the bartender who smiled and nodded, they shook hands and there was a quick hug and Daniel dropped cash on the bar. He put his hand around my waist and leaned into my ear.
“Let’s go,” he said, pulling me with him to the exit.
It was chilly out, the cool air hit my sweaty skin and it felt good, “I’m about fourteen blocks from here,” I offered.
“That’s too far, over here,” he said, pulling a key from under a mailbox on the wall, it unlocked a door that lead upstairs above the club. “The bartender is my friend, he lives here and won’t be done until the bar closes,” he pulled me up the stairs with him.
The place was surprisingly clean and tighty, a studio laid out like a hotel room, smelled a bit like a locker room though.
Daniel closed and locked the door behind us, then pulled me into a kiss, stripping off his shirt as quickly as possible, then his jeans. Standing in his white Jockey briefs, his dick sticking out the the Y front fly, it was a thick 7” and uncut. He pulled my shirt back off and pushed me towards the bed in the middle of the room. This aggressive side of him was hot as hell and I couldn’t help but meet his energy with every move.
I yanked my pants off, my briefs tugging down with thim, my dick sprung up with excitement as Daniel pushed me onto the bed. I didn’t need another blow job, but I was going to let Daniel do what he wanted. He got down on his knees at the foot of the bed and instead of putting my dick in his mouth he lift my legs up over his head, climbed on the bed with me and pinned my legs up by my head. Grinding the part of his dick that was already free up and down my sweaty crack.
The feeling of his cock sliding up and down my crack was another new sensation, I moaned, “what are you doing?” I asked.
“Teasing your hole,” he groaned and thrust his dick across my hole.
Then he impressively manhandled my legs to flip me over onto my stomach and before I could ask again what he was doing he ran a finger across my hole and my body betrayed me and moaned again. Then his tongue licked up my crack, gliding over my hole and the sensation damn near made me cum.
“Holy…fuck,” I groaned.
“Never had your ass eaten?” He asked and then really started to slobber and lick my hole.
“Mmm, no, fuck that feels good,” I spread my legs like a slut so he could get better access.
He licked and used his hands to pull apart my toned ass, then pushed his tongue into my tight sphincter.
“Oh fuck,” I groaned and felt a drop of precum spurt out the tip of my dick.
“Dang you’re hole is tight,” he murmured and pushed his tongue harder, licking my inner walls and giving me a pleasure I had no idea existed. I was like putty in his hands.
He nibbled and licked, and sucked on my hole, digging his tongue into me and pulling my ass apart like he was defusing a bomb with his mouth.
“Holy shit, that feels good,” I groaned, wriggling on the mattress, my hard dick leaking precum onto the sheets.
He reached over into the drawer and pulled out some lube, squirting it on my hole and gently fingered me.
“Mmm, what are you doing?” I asked like an idiot.
“You are way to tight to go in dry,” he chuckled.
The words bounced around in my dizzy head for a second as he slipped a second finger into my hole, “ahh,” I winced.
“Fuck you’re so tight,” he pushed in deeper with a air of gentleness.
“Nobody’s ever played with my hole before,” I moaned, the sting subsiding, being replaced with pleasure.
“Wait, are you a top?” he asked, pushing a third finger into my hole.
“Ungh…” I popped up on my elbows from that sting, “Yeah, why?” I looked back at him over my shoulder.
He had pulled his underwear off and was stroking his dick with the hand not inside me, it was glistening with lube and hard as a rock, he was smiling, “well,” his grin became mischievous as he pulled his fingers from my hole, “I’m not a bottom,” he straddle my ass quickly, rubbing his dick across my well lubed hole.
“I…” the sensation of his cock sliding over my hole, catching on the outer ring tingled through my body, “I can’t, I don’t,” I struggled to form words as my body rejected them in favor of pleasure as his head found the center of my sphincter and gently pushed. “Ungh, fuck, wait, wait,” I groaned as the head popped in and my arms gave out from under me.
“Just take a deep breath and push out,” he whispered, adding more pressure.
“Ok wait, I have a condom in my pocket,” I told him.
“Ok, let me just loosen you up a bit and then I’ll get it,” he gripped my hips, using his thumbs to put pressure on my lower back muscles which felt like a massage and my ass let him sink in an inch. “That’s it, baby, just let my dick inside you,” he kept adding gentle pressure as his hot iron dick went where no one had ever been.
“Uhg,” I gasped, “Fuuuuuck,” I groaned, the pain was too much, I was about to buck him off of me when he slid his hands up my back.
“I’ll wait for you, just open up for me,” he said gently, massaging my lower back and ass cheeks.
Somehow the extra skin from his uncut cock made it so he could gently move in and out of my hole just millimeters to keep him aroused and, “oh yeah that’s it, I can feel my precum lubing you up already,” he rocked his hips waiting for me to let him push all the way in.
I could feel it, my ass squeezing tightly around his cock as he popped my anal cherry and oozed precum into my hole, I let out a soft moan and he gave a gentle thrust, another inch going into me.
“Ah, fuck,” I groaned.
“It’s almost in, you’re doing great Preston, just a little more,” he gave another gentle thrust.
This one was too much and it stung, bad, like someone stabbed me in my asshole, “ow, fuck,” I shouted and bucked him off quickly.
“Sorry, are you ok, was that too much?” He asked.
I was up by the headboard of the bed, “fuck man, I don’t think I can do this,” I clenched my hole, sitting up with my back to the headboard, my flaccid cock hanging over my balls.
He hopped up off the bed, yanked his briefs all the way to the floor and kicked them across the room, “sure you can,” he grinned at me, turning off the overhead light and turning on a lamp. He reached into the drawer again and pulled out a small brown bottle, “you just need to relax.”
He climbed back into the bed, and kissed me gently, which I accepted, then his tongue parted my lips and started to explore my mouth. He tasted so good, I was feeling euphoric, still felt that sting all the way up my spine, but he was a really good kisser and I was here for it.
He shifts our bodies around, not breaking the kiss but managing to get me flat on my back, him laying on top of me, gentle moans between the two of us, breathing heavily as I felt my dick grow back to full hardness rubbing against his thicker dick. I reached down and tugged at his cock, a decent amount of precum had pooled inside the tip and now leaked out onto my hand, I stroked him a little harder and he broke our kiss, spreading my legs and lifting my ass up he tucked a pillow under my ass.
He took the lube and applied more to his dick and then very gently to my hole. He took the little brown bottle, shook it and opened it, inhaling deep from the opening, “mmm,” he exhaled and then did it again and passed me the bottle. The look on my face asking the question in my head. “It’ll help you relax,” he said, “just take a hit, I promise you’ll like it,” he said. I did as I was told.
A rush came over my body, I felt instantly drunk and high at the same time, that sting was completely gone inside me and my lust for Daniel grew tenfold. He spread my legs and positioned his dick at my hole, his precum slicked my hole as he rubbed it up and down.
“You need a condom,” I reminded him.
“I will, just need to get you loosened up first,” he said, matter of factly. “Take another hit, real deep breath and hold it until you can’t hold it anymore,” he instructed.
I did as I was told, and as soon as I put the cap back on I felt his dick pushing gently into me again. This time my hole allowed the first inch to go in no problem, the second gently slid in but the third I couldn’t hold my breath in anymore and let it out. The rush was incredible, I felt that heat run through my body and the heat from his dick inside my hole was amazing. He gently pushed a little more, and then a little more until I felt his trimmed pubes brushing against my ass.
He let out a low growl, “oh fuck Preston you’re so fucking tight, you’re hole has such a tight grip on my dick,” he rocked his hips, “you have my entire dick inside you baby, you feel it?”
I felt everything with an overwhelming amount of pain and pleasure, mixed with a need for more of both, I moaned, “fuck, Daniel, just wait a second,” I groaned, still trying to adjust to this intrusion on my hole.
“It’s ok baby, I’ll wait for you to get used to having a dick in your ass, it feels so good for both of us,” he told me, leaning in to kiss me and his hips rocked another centimeter of his thick cock into me when he did.
“Mmm,” we both moaned as we kissed.
He held his torso in a hover oboe my body with one elbow planking in the mattress, his other hand gently gripped three back of my neck pulling out kiss tighter. He rocked his hips again, testing my hole to make sure I was ready to feel him use it for his pleasure.
I let out a soft moan feeling the tip of his dick hit a little deeper inside me, fuck I can't believe how good this feels. I can't believe I'm breaking my no bottoming rule for Daniel. He rocked his hips again, even deeper, I moaned.
His free hand traced is easy down my body to my dick. He gripped it lightly and slowly jerked it between the two of us as he sucked my tongue and pushed his dick deeper into me. I let out a moan of pleasure, breaking our kiss, “oh fuck…that…feels so good,” I shook my head in disbelief.
“You feel so good. Your hole is miking the precum out of my dick,” he grinned down at me.
My eyes shot wide, I'm breaking both of my rules with Daniel. “We need to get a condom,” I told him as he closed his eyes and kissed me again, and again.
Rocking his hips with a purposefully careful motion, his free hand scooped under my right leg, pulling it into his shoulder. Then he leaned in and scored the other leg onto his shoulder. I didn't know I could stretch like this, my quads were stretching under his sweaty, skinny torso. My hole stretching around the root of his cock.
“In a minute, just want to get you lessened up a bit so your virgin home doesn't slam shut on us when I pull out,” he kissed me again.
His words ran through my head as he slowly pulled out and gently pushed back in. It made sense, my dick was already clamping down tight on his dick. He thrust deeper, “ung,”I groaned. He kissed me again. Holding me tighter with every thrust.
“My precum is lubing your hole now, feel it sliding in easier?” He kissed my neck.
He was right, fuck it was starting to feel good, really good. I wrapped my arms around his back, holding onto him as his little thrusts rocked my body and my world.
“Mmm, fuck Daniel,” I moaned softly into his ear.
“Yeah, feels good doesn’t it? I’m not even fucking you yet and it feels so good,” he pulled a third of the way out and thrust back in all the way. “Mmm, fuck you’re so tight, Preston. You might make me cum before I can really fuck you,” he chuckled in my ear and then thrust again, this time sliding out about half way and in to the root.
I groaned, there was so much pleasure in every thrust. He pushed himself up onto his knees, holding my knees on his shoulders and started to gently make full thrusts, nice and easy but building a rhythm with every push. “That’s it, I can feel you opening up for my dick, you want it so bad don’t you?” he grunted, his voice dropping an octave as he started to become a little more aggressive with his thrust.
I just moaned, unsure what to do, my head was spinning, and I was bottoming, bareback for the TA that I have to see two times a week, “mmm, fuck Daniel,” he hit a spot inside me that sent shivers of pleasure up my spine and into my brain, I saw stars for a second, “Oh shit,” my ankles wrapped around his long neck.
“Yeah, that’s it, baby, now you’re bottoming, now you’re enjoying my dick,” he grunted out, his hips slamming into my ass now. Every thrust felt so good that I couldn’t help but moan. Every single thrust was pegging my prostate with the head of his cock and then running the length of it, I felt every ridge of his cock sliding in and out of my hole.
“Oh fuck, that feels so good,” I moaned, flexing my ass around his cock, rocking my hips to meet his thrusts.
“That’s it baby, fuck Preston, you’re so hot,” he was grunting and groaning in pleasure.
I started to jerk myself off, every thrust that pegged my prostate released some precum from my cut dick. It only took a few breathless strokes of my dick before I was ready to blow my second load of the night. I rocked my hips on Daniel’s cock, “fuck don’t stop,” I told him.
“You gonna cum for me?” He asked, pegging my prostate even faster, a little harder now.
“I’m close,” I told him, rocking my hips, flexing my ass hole around his cock.
“Me too,” he warned.
“Fuck I’m gonna cum, I’m gonna cum,” I shouted and clamped my ass down hard on his dick, my abs tightened and his cock pistoned in and out of my hole and, “Oh my god, I’m cumming,” I shouted. I felt my balls tighten and I erupted molten hot cum all over my chest.
“Me too,” he shouted.
“Pull out,” I tried to say.
“Too late,” he thrust in hard and I felt his big cock twitch as he spewed his load 7 inches deep inside me, he twitched and thrust again, hitting my prostate again, and I clamped harder on his cock as his cum coated my insides, and my orgasm kept running through my body, stealing pleasure from his orgasm and the new sensation of having hot cum inside my hole.
“Ungh,” we both grunted as our orgasms let out the last ropes of our cum. Mine pooled in the valleys of my abs as his flooded my insides.
“Oh fuck,” I gasped for breath.
He leaned on my legs, stretching my ass even more, and kissed me from between my knees.
“Holy shit that felt so good,” he kissed me again.
His dick slid out of my ass with an audible plop, I felt some of his cum smear a trail the entire way out as it lubed every ridge of my hole and he rolled off of me.
“Fuck man,” I said, catching my breath. “Did we just do that?”
He chuckled, “Preston, you were so hot, you are a natural bottom,” his voice trailed off.
“Daniel…you came inside me,” I wrapped my mind around what just happened.
He sat up on his elbow and looked me in the eye, “It’s ok, I promise, and fuck it was so hot giving it to you.” He kissed me gently, I kissed him back.
My mind raced for the next few minutes, getting dressed was a blur. I just kept thinking, the TA just blew his load in me, I have cum inside me, I had unsafe sex, over and over in my head until we were outside and he hugged me.
“You ok?” he asked, “Do you want me to walk you home?”
I shook my head, “Yeah, I’m good, just drained,” I put on a smile and hugged him.
“Ok, I’ll see you Tuesday,” he said and walked to a Taxi cue by the club entrance.
Oh fuck, I am going to see him twice a week for the rest of the year. I don’t know how I’m going to be able to pay attention in class knowing what he looks like naked, knowing the face he makes when he cums, knowing that when he looks at me in class he’s thinking about how he barebacked me, and was the first guy to plant his seed in me.
My mind raced the entire way home, where I showered, jerked off, and eventually fell asleep. Missing my Friday class because I slept until 1 pm.
