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Me, Myself, and Two Guys

"Me and two guys, but it isn't what you think..."

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2.8k words 2.8k words

Author's Notes

"Although the following events are true, names have been changed to protect the naughty."

Sam and Ryan were both music majors at my university. We were all seniors and I had seen them at parties and they were friends with my roommates. I have a thing for musicians and we clicked right away. Sam and Ryan weren’t that close of friends with each other, mostly just classmates. I got to know each of them separately and they became my good friends. Sam was first to ask me to hang out. I was thrilled that he wanted to see me outside of the usual party scene and we made plans to spend time alone together in his dorm room.

I was attracted to Sam because he was creative and intelligent. I liked Ryan because of his charm and free spirit. I told my roommate about my plan of trying to hook up with Sam and we giggled together imagining what may happen. She told me that the word around our friend group was that Sam had a huge cock. It wouldn’t be the first penis I’d ever seen, but I was intrigued by his rumored size.

I hadn’t hooked up with anyone all semester and was getting antsy. My horny mindset may have clouded some judgement as I ended up with two guys that night. Little did I know then that these two experiences would be polar opposites.

On the night of my “date”, my roommate helped me pick out the perfect sexy outfit. I wore my best black and nude lacy push-up bra, not that I needed any extra padding, my breasts were already a 32DD. I wore matching black sheer panties, a low-cut purple sweater and tight navy jeans that hugged my ass and showcased my curves. I felt confident, but gulped a glass of wine just for insurance, in case my nerves served as a cock block. Some liquid courage helped me feel prepared.

We both lived on campus and it was a quick walk to his dorm. Once I got there, Sam opened the door and was excited to show me his room. It was small, just a bed, a flat-screen tv, and some musical instruments. I knew he was a good musician, I hoped he would be good with his tongue in other ways too.

“So…what do you wanna do?” Sam asked nonchalantly, after giving me a thirty-second tour of his tiny place.

“Hmm, whatever you want,” I tried to play it cool.

“We could watch a movie?” he offered.

“Sounds good to me!”

We moved to the bed and didn’t waste any time. He basically had my shirt off before the opening credits. Looking back, I wonder if I should’ve waited, it was only a first date, but you only live once, right?

Besides, Sam was pretty cute. Cleanly shaven with perfectly gelled hair and dressed in a button-down shirt and neatly pressed khakis. He looked like a proper gentleman. Although I would find out he was everything but. He had a decent body, but it was his hands that really turned me on. Large hands reached out to grab my ass and pull me into him. His green eyes seemed to soak in my body, staring so intently as if to burn my nakedness into his memory. Sounds intense; I found it erotic. At least at first.

Then Sam took my bra off, freeing my tits, and began massaging my nipples. I unbuttoned his pants, where his nine-inch hard dick slithered out. I was relieved the rumors did not disappoint.

I wasn’t all that sexually experienced yet, but I mustered some faux confidence and took his cock in my hand to stroke him. We were facing each other and he leaned down to take my breast in his mouth. He sucked on my nipple, rolling it around with his tongue. When he let go, I rolled over and wiggled out of my jeans and slipped off my panties.

“Your tits are out of this world,” he begged. And yes he really said that. I kind of laughed.

I loved watching his eyes explore my exposed body. I got on top of him, rubbing my virgin pussy lips on his shaft. My throbbing clit slowly ground up and down his hard cock, leaving a trail of wetness behind. I wondered if he was going to penetrate me. It would have been my first time and I didn’t know if I wanted him to be my first.

His precum and my juices mixed, allowing my pussy to slip and slide easily. He reached up and grabbed a handful of my tits and bit my now hard nipple, tracing my areola with his tongue. His other hand reached around my waist and pulled me closer.

My head went back and my eyes closed as I moaned. He wasn’t inside me, but inched closer to my little hole with each push between my lips. It felt so good to have his hands on me.

“Kiss me,” Sam ordered, sitting up with his back against the headboard.

As I leaned forward, he also moved closer and we inadvertently bopped heads. It didn’t hurt but it was slightly embarrassing. We laughed awkwardly and I rolled off his lap and plopped next to him. We kissed for some time and although it was pleasant, I found myself becoming bored. I think he sensed this and he tried to change it up by dragging his fingers down my body towards my wet hungry pussy. I felt his fingers right outside my pussy. We locked eyes as he entered me, first one finger, then another. It felt a little awkward and my mind started to drift.

“You’re so tight,” he whispered, I felt his warm breath touch my face.

He started trying to talk dirty, but it sounded more filthy than sexy. His words sounded scripted and so were his moves. I felt like I was in a cliché porno with sub-par fingering. I didn’t want to hurt his feelings but I began to feel less aroused, so I focused my attention on getting him off instead.

I sat up, planning to jerk his big cock and let him cum on my big bouncing tits, since he couldn’t take his eyes off of them. I wrapped my hand around his member and began to twist and then fondled his balls. I love watching a guy cum so I thought maybe that would get me closer to my desired orgasm.

“Hold on, hold on,” Sam opened his eyes and interrupted my vigorous hand job.

He reached over in his desk drawer and grabbed a condom.

“I want to finish in this,” he handed me the wrapper.

“You don’t want to finish on me?” I began putting the condom on him.

“I always finish in a condom, easier to clean up,” he leaned back, waiting for me to start again.

I shrugged at this convenient request and unrolled the rubber onto his dick and continued touching his body. I felt his muscles clench and his hips move as he was close to climax.

“Keep going, just like that, don’t stop, fuck,” Sam tightened up, mouth open.

“Mmm, you like that? Come for me…” I purred, trying my best to sound seductive and stay present in the moment. My pussy hungry for my turn.

He reached up to play with my tits as they jiggled. Then all of a sudden, his legs jerked, he let out a moan, and the condom filled with his warm wet cum.

“Oh yeah, that felt awesome,” Sam removed my hands and peeled off the condom himself.

Smells of rubber and sweat filled the air and I was suddenly aware that he had no intention of getting me off too.

“Alright, that was fun,” he seemed to nod towards the door.

“Oh, um, okay,” I tried not to look disappointed, wondering if he simply forgot I hadn’t finished. Or worse, he thought I had somehow.

“You really exhausted me. That was great. It’s not too dark outside right? You’re all good?” He looked out the window.

My brows furrowed. I knew that was code for: You can see yourself out.

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“Yeah whatever, it’s fine. I’ll see you around,” I embarrassingly grabbed my cell phone and purse and headed for my dorm dissatisfied in more ways than one.

I knew then that his intense gaze at the beginning was in fact to memorize my body, because he probably wouldn’t be seeing me again for a second round.

Luckily, all was not lost as I got a text from Ryan on my way back to my dorm.

At a party, room 333, come NOW.

I needed a release. My elusive orgasm and aching pussy convinced me that maybe more was in store for this night. I went in search of a missing orgasm from another willing participant.

While Ryan was also a musician like Sam, he was of a different breed. He was more of a rockstar while Sam was a classical composer. And you could tell each had their own vibe. Ryan had messy dark hair that fell just below his eyebrows, and he needed to flick it to the side to get his bangs out of his hazel eyes.

He was about 5’8”, only a couple inches taller than me. He had a scruffy beard, wore jeans and a black band t-shirt. Ryan carried his guitar around everywhere; I imagine to serenade some girls before trying to fuck them.

I had known Ryan for a while and there was always some sexual energy between us. I had never acted on it before because I didn’t want to ruin our friendship. This time my restless cunt didn’t let me think too much about it.

When I arrived at the party, the music was blasting, everyone looked wasted, and the air was smokey. Ryan saw me immediately and came over.

“Hey you, glad you made it, you look great!” Ryan grabbed my hand and led me back outside where we could be alone.

“Glad you texted me, looks like a fun party. Want to go back inside?” I began to open the door.

“Nah, the party is shit, no one cool is here. Wanna get out of here?” His eyes looked like they held mischievous secrets.

“Why not?”

He was still holding my hand and looked down smiling. I took his cue and followed him into the dark for a walk.

We wandered around campus for a bit and ended up at my dorm. I lived in a three-bedroom apartment with five suitemates. One of them was out and the others were already asleep as it was two in the morning at this point. I offered Ryan a drink and we sat on the couch. His hand started off on my thigh, rubbing my leg through my jeans.

I followed his lead and turned to face him inching closer. He dragged his hands up my thigh and traveled slowly up underneath my sweater. He touched my breast and slid inside my bra. As soon as he grazed my nipple, it hardened, I was immediately aroused. My panties were getting wet and I reached to rub his cock which was felt trapped under his pants.

Ryan kissed me and ran his hands down my back, hooking his fingers in the loops of my jeans, pulling me into his lap.

We dry hump, my clothed pussy rubbing against his crotch and feeling his dick trying to free itself through his zipper. He lifted me up and we stumble to a free bedroom. My roommate and I share a bedroom and she was already asleep and locked the door. The only free room was my other suitemate’s. Since she was out, it seemed like fair game. Ryan bit my lip as he kissed me, sending shivers down my spine as our tongues played.

We didn’t even bother to close the bedroom door. Not wanting to mess up my suitemate’s bed, he pushed me onto her nearby desk. Pencils flew everywhere, and I made a mental note to pick those up later. My suitemate was a stickler for organization and would notice if something was amiss.

Ryan tore off my shirt and I unzipped his jeans. His dick popped out and I began to stroke it.

“Take off your pants,” he breathed, his head dropping back in pleasure.

For the second time tonight, I wiggled out of my jeans and took off my bra. He immediately grabbed a fistful of my tit and took my little pink nipple into his mouth. He was a bit rough, grabbing my curves like there was a sense of urgency. Which there was, as we hid in my friend’s room and needed to finish before she came in.

“Talk dirty to me. Describe yourself in the shower,” he moaned.

I just dove right in, no qualms about it. I was so horny, yearning to find my missing orgasm.

“I’m so wet and soapy. I rub the soap all over my tits and ass, making my way down to my pussy…” I started.

“Yes, keep going,” he began to search for my clit in the darkness.

My pussy was aching for his fingers to enter. He smelled like cigarettes and cologne which was an interesting mix, but at least his fingers were as talented at playing with my pussy as they were strumming his guitar. He had great arms, probably since he was a drummer too. He lifted me back up onto the desk as I was slipping off.

“I soap up my pussy, there’s bubbles everywhere…I rub my clit and feel how I’m dripping wet, soaking, and I slide my finger inside,” I continued and simultaneously Ryan entered me.

He started slow but once my wetness lubricated his fingers, he sped up, hitting my g-spot and making me cry out in ecstasy.

“Fuck yes, right there!” I was so close to finishing.

“I want to watch you touch yourself,” Ryan interrupted as he pulled his dick away from my hands and stepped back.

I felt his fingers pull out of my pussy and were drenched in my juices. He licked his fingers and began to jerk off watching me masturbate. I spread my legs, balancing on the desk. Using my thumb and middle finger, I pull apart my pussy lips and allowed his eyes to explore all down my curves and pink folds. It was dark, but I could see his mouth hang open as he stroked his cock faster and faster staring at my almost bald, neatly trimmed bush and jiggling tits. I rubbed my clit with my index finger watching his eyes follow. Then I ran my finger up and down my swollen slit and moaned as I brought myself to my long-awaited orgasm.

“Oh my god, fuck yes,” I slurred, as he came too from watching my body shake and my legs tremble.

The wave of my orgasm rippled through my body and Ryan squirted his cum onto my legs, just outside of my pussy. Once he collected himself, he used his shirt to wipe it off.

I jumped off the desk and fixed those damn pencils and looked around for my bra and panties.

“That was fun, maybe a second round another time after class?” Ryan commented, buttoning up his pants.

“Yeah maybe. That was fun,” I wasn’t sure yet if I wanted to do it again or if this was a one-time thing.

“Alright cool, well see ya around!” He headed for the door. I watched him leave, took a second to fix my suitemate’s desk, collected my clothes and went to my own bedroom.

I changed into grey sweatpants and a white t-shirt, and got into bed, thinking about my two totally different encounters of the night. I had not expected this to happen and was laying there wondering what it would be like the next time I ran into Sam or Ryan. I also hoped my suitemate wouldn’t find out about what happened on her desk. Hopefully no extraneous cum left over!

I was happy to have had at least one orgasm that night, I would have preferred two though. So I pulled out my quietest vibrator, so as to not disturb my sleeping roommate, and had a second round of fun by myself and drifted off to sleep.

 

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Written by gracefulxgem
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