A gay story: (Not So) Little Richy College was a true awakening for my sexual life. Prior to (and during) college I presented as straight and masculine as they come. I learned a lot about myself through quite a few female partners in that time. But one thing always lingered in my mind without ever acting on it.
As time went on, I’d found myself being more and more turned on by masculinity. I started with only seeking out porn with men that had larger cocks. Then came a transgender porn fetish. Then came full-blown gay porn.
Then the realization that I wanted to bed men, taste them, be fucked by them. I couldn’t get it out of my head, but for years I never acted. Until the New York trip in my final year of college…
I wasn’t certain about going on the trip, although most of my peers were committed to going. I finally pulled the trigger at the last moment, but this meant that most rooms were accounted for. I found out that I’d be rooming with the last student who didn’t have a roommate, Richard.
Richard was what most would describe as the ideal twink. Slim, but not scrawny, clean face, plush lips. I’d never thought of him in my sexual fantasies of men, but once I knew we were in a room together, those thoughts took over my brain. Richard was always kind but we’d never hung out outside of parties. Needless to say, I was jittery at the idea of sharing a room.
Our first day there was spent travelling and then a dinner with all the classmates. Some were still under 21 like Richard, so while the rest of us were drinking at the dinner, the younger ones funnelled out with an of-age classmate to fetch alcohol for the night. The rumblings at dinner were that the others went back to the hotel to drink and “our plan” was to go clubbing. My dirtier thoughts got the best of me. I told my friends I was going to head back to the hotel while they enjoyed a night out.
I bought a few bottles of tequila and headed back to the rooms to find the party. It turned out that the younger classmates were drinking, but slowly struggling to keep awake. By the time I got there, two girlfriends who were approaching a black-out drunken stage were in my room with Richard who seemed to hold his booze well.
Shortly thereafter, I did the responsible thing and got the ladies back to their rooms.
“Okay, bedtime for you girls.” I said as they leaned on each of my shoulders.
I expected Richard to turn in but to my surprise he was still game.
“Hey, can I open up this other bottle? We shouldn’t turn in so early on the first night right?” he said.
I smirked at him and said, “Absolutely, I’ll be back”
I dropped the girls and returned to mine and Richard’s room hearing the sounds of the shower and no sign of the bottle. I began to roll a joint as I assumed Richard had changed his mind on staying up. As I licked the rolling paper and sat by the window, Richard exited the bathroom.
“Tequila tiiiiime” he said flamboyantly.
I laughed.
“Wow, just had to do a quick mid-drinking shower? I guess I’ll hold onto this joint for later then.”
At that point I noticed Richard standing, only in his tight briefs and a towel around his neck, the generous bulge the Richy was sporting. I tried to pull my eyes away, but he must’ve known what he was flaunting.
“Noooo, let’s smoke now! Yeah?” He insisted as he bounced onto my bed.
“I’m down. Just come to the window so we don’t make this place stink.”
I was sitting cross-legged on the floor as he walked over, I glanced up at the obvious bulge but stared away before he sat. Well, actually, he slammed down in a bit of a drunken stumble.
“Okay, my turn on the bottle, I’ve got to catch up to you.” I said.
He giggled and watched me take 2 big swigs out of the bottle. I put it back down between his legs. I was trying to be discreet, but there’s probably nothing discreet about a drunk guy placing a bottle inches from a bulge he can’t keep his eyes off. I kept glancing between his eyes staring at me and that bulge of his while I lit the joint. I took a big puff and passed it. He inhaled deeply before being very forward.
“You know, you sure stare a lot for a straight boy…” He said while looking me up and down, passing the joint as our shoulders touched, leaning against the window.
I was so caught off guard, I’d never openly expressed anything like this but my inhibitions took over.
“Well, what makes you think I’m so straight?” I said.
He giggled with a hand on my leg. I could feel myself getting butterflies.
“Well, Casey’s drunk ass was just telling us about you two hooking up like alllll through last year.” He said, staring cheeky daggers.
I blush and chuckle lightly, saying, “Well, who says I’m only interested in girls?”
It was silent for a moment as he puffed away on the joint.
“And it’s hard to ignore a bulge like that swinging around…”
I reciprocated the leg touching as he smiled so cute with rose-red drunken cheeks. He looked back away.
He then said something I’ll never forget: “Well then, do something about it.”
I reached out and grabbed his chunky bulge. He looked to me biting his lip, “Good boy”, he said. He pulled the joint from his lips and but it between mine, his fingers pressed up on my lips as I felt a serious twitch in his bulge.
I exhaled, “I didn’t expect such a cute little guy like you to be so… endowed.”
We both laughed.
“Endowed? What are you 50?” He laughed.
“Sorry, vocabulary ages with the alcohol.” I said, rubbing his growing penis a bit more sternly.
“No, it’s cute… and I’m full of surprises.” He said, putting a hand on the back of my head, kissing me.
In all my fantasies of men, I’d never imagined a kiss. Maybe that’s what made this so sexy to me. I was throbbing hard, and Richard was still growing and in full control. We continued to make out passionately. Feeling him grow bigger, to the point where I thought his underwear’s seems would split, made me kiss him back harder. Swapping tongues and spit.
Then after what felt like an eternity, he pulled me away.
A strand of saliva breaking between us, he said, “Well, isn’t this a nice cherry on top of this trip.”
He began puffing on the joint, reigniting it and passing it back to me. He looked down to my hand still attempting to cup his engorged bulge and giggled.
“Sorry,” I said with a smirk, “hard to keep my hands off of it.”
“Yeah, it has that affect on people and I really don’t mind.” He said with a smirk.
He kissed me again. Slowly and romantically he pulled away.
“So, have you ever done this kind of thing?” He asked.
“Well, this kind of thing?” I said signalling toward his beautiful package, “Not quite. And actually… no kind of thing with a guy ever.” I said with a bit of a nervous laugh.
“Aww, that’s cute… Well, I might be a bit much for you.” He said, with a disappointed tone.
“But I’ve used toys!” I shouted, a little too eagerly.
He laughed, “Oh wow, so, you’ve been wanting this, huh? Bad boy… we’ll have to see what we can do then.”
He popped up, “Should we watch a movie?”
“You can watch a movie,” I said, readily horny for every bit of him, “I’m going to be focussed on other things.”
He laid down in my bed on his back, “Show me what you mean.”
I walked to the bed, crawling between his legs. I instantly smothered myself in his bulge. Teething at it over the underwear. He let out a light grunt before I heard voices in the hall.
“Don’t worry, I don’t have to tell anyone.” He said, certainly to my eyes, looking up to him.
I was fully in. Knee deep in something I couldn’t have even imagined. I ripped his underwear off instantly and smothered myself in his bulge. Licking, kissing, drooling and finally, I put his enormous tip in my mouth. Richard groaned and gave a few reaffirming comments like, “Fuck you’re a good boy”, all while he chose a movie.
“You just keep sucking until I say you’re done. If I cum, you better not take that as a finished job, got it?” He said in a tone I didn’t know he had.
I dry humped and grinded on his long leg as I fully fell in love with the taste, feel and hardness of his enormous cock. This thing was fucking fully porno-sized and he was so proud of it. It was undeniably sexy. My jaw began to hurt and he saw it.
“Just keep stroking and licking those balls, I know you’re tired, but you’ll get there, babe” He breathily whispered.
As much as I loved his big beautiful cock, I needed him to cum. I’d go for as long as he needed but I craved that load to shoot. I felt him getting closer, his hands tighter on my head, his balls tensing, and his grunts deeper. I opened my throat, my drool soaking his balls and lap.
“Ughh fuck, fuck swallow this fucking cock until you have my load in you baby, yes! Fuck, you’re such a good little straight bitch. Fuck suck, Oh yes, FUCK!”
His already-hard and fully engorged cock became harder, twitching with a strength that felt like it could lift my up from inside my throat. I stroked with my hand to keep it stable as his warm, creamy load filled my mouth. I slurped with my head around the tip, swallowing every drop I could.
His grunts became pants, and his eyes closed and he gave me the greatest affirmations of an orgasm well-achieved.
“You taste so fucking good.”
I kept licking and lightly sucking his softening cock as he seemed to drift closer to sleep.
As I slowed down, he said lightly but affirmatively, “Go into my front pocket, grab the silver butt plug and come back to bed. And take off those clothes, cutie.”
I did it eagerly. I laid next to him and handed him the plug as he kissed me. He shoved the plug in my mouth.
“Get it nice and wet for you baby.” He said as he flipped me over into a spooning position.
I felt his soaking wet cock flop onto my ass. He cupped my juicy cheeks, giving a light spank before slipping in a finger.
“Now, keep this in here for me all night, baby, can you do that for daddy?”
Before I could answer I let out a moan and a squeal as he slipped it in.
“Yes, sir.” I said, satisfied as he drifted to sleep on my back.