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Party. My apartment. Noon. Basketball.
Those were the only words Jimmy had left on my voicemail. It was a Sunday in March and the March Madness basketball tournament was underway. I hadn't talked to Jimmy since I switched jobs. I hadn't talked to Kat either. Despite their general toxicity, as well as the ticking time bomb of my short term sexual affair with Jimmy, they were my first two friends when I moved down here. I missed them and thought it would be good to see them again. Surely, if Kat had any idea about the missteps Jimmy and I had made, Jimmy would not be inviting me to a party at their apartment.
In other news, my roommate and her fiancé had moved out of the apartment and into a place of their own in early March and I had the apartment to myself until June 15th when my lease expired. I still had not found a place to live and time was running short. I packed that anxiety away for another day and hopped in the shower. It was already 1030am and I wanted to at least watch the early games with Jimmy and Kat before meeting Courtney for early evening drinks.
I arrived at Jimmy and Kat's apartment at 1230pm. I had done two shots of tequila before heading over as a remedy for my frayed nerves. I was dressed in a blue gators tank top, as my orange version had been ruined during my last visit here. I quickly noticed I was the only party attendee so far.
Jimmy was decked out in blue gator gear, sitting on the sofa by himself.
"Where's Kat?" I inquired.
"We're done. She moved back home two weeks ago," Jimmy replied.
Had she found out about me and Jimmy? Had she just had enough of him? Or did Jimmy break up with her? Questions were flying through my mind while anxiety was shooting through my chest.
I should've figured by the state of the apartment she was gone. It was a mess. There were beer bottles all over the table and what looked like a left over styrofoam container of wings on the floor near the television. There was an air mattress in the corner with a baseball cap and what looked like a pack of cigarettes inside it.
"Beer is in the fridge," Jimmy informed me without even glancing at me. The fridge was filled with beer bottles and only beer bottles. I grabbed one and returned to the living room.
"There's blow in the bedroom as well," he said nonchalantly.
I walked in to his bedroom and observed a mess similar to that in the living room. Clothes were strewn along the floor. Jimmy had taken Kat's full length mirror and laid it flat on the dresser, just below an upright mirror. The flat full length mirror had dozens of line of cocaine already cut and awaiting willing party patrons.
"Why not," I mumbled to myself as I grabbed the already used, rolled up bill and snorted a line.
I returned to the living room and sat next to Jimmy.
"Nice tank," he quipped; a comment I ignored.
The apartment door opened with what I expected would be more party attendees; however, only Kevin, Jimmy's roommate, walked through the door.
He did a double take when he saw me sitting next to Jimmy and shot me a mischievous smile - which I also ignored. I nervously finished my beer and went to the kitchen. I noticed a half-full bottle of tequila and took a healthy swig of it. The blow had made me feel good but I still had a bit of anxiety due to the circumstances.
I returned to the living room with a fresh beer which I quickly finished without even tasting it. I needed more blow to clear my mind.
I walked into Jimmy's room and found the thickest line and snorted it. Half of it anyway, as the line was too thick to do the whole thing. The rush to my head was perfect. I bent over and finished the line as Jimmy walked in to snort some himself. He pulled out his keys and scooped up a small bump on the edge of one of them, quickly snorting it.
He walked behind me and in the mirror I could see him use his hands to brush my platinum blond hair from the front of my body toward him so that it was hanging down my back. The tingle of his fingertips inadvertently touching my neck felt so sooo good.
As sure as clockwork Jimmy reached around and pulled my tank top down. My 36C tits had built themselves quite a reputation in my short time down here. I watched our reflections in the mirror as he fondled my tits with a firm, yet pleasurable touch. I leaned my head back against Jimmy's body briefly before returning my gaze to the mirror. His roaming hands exposed and then hid the tan lines on my breasts. He pinched my nipples sternly before resuming my chest massage.
The blow had me feeling high. All inhibition was gone. I knelt down in front of a standing Jimmy. I unbuttoned his jeans and they fell to the floor. Jimmy stepped out of them and presented himself to me, already a fully hard 8 inches that I had met a few times before. I was so horny. I was going to suck and fuck the shit out of him.
I had laser focus on Jimmy's dick. There was no teasing. I was sucking his cock sloppily, trying to swallow it all. His groans were loud. They should have been, I was giving one hell of a blow job. All I could see was his dick and stomach as I knelt before him. Nothing else mattered.
Then I felt a tap on my shoulder. With Jimmy's dick still in my mouth I looked to my left to find Kevin - his pants off and his uncircumcised cock standing at attention. I took Jimmy's dick out of my mouth, still holding it in my right hand. I leaned over and grabbed Kevin's with my left and slid it into my warm, wet mouth. I sucked on his foreskin and then took his hard shaft in my mouth.
A hand grabbed my hair. It was Jimmy and he pulled my mouth back over to his cock which had been momentarily neglected. He put his dick in my mouth, his hand still holding my hair, and began to pump steadily. It wasn't as aggressive as the first time Jimmy had face fucked me two months ago but his dick was so big that I gagged on it nonetheless. His second hand dropped down to my head as well and held it still as he emptied the content of his balls down my throat. After a deep breath, he pulled his dick out of my mouth and left the room.
Kevin was still standing there pantless. His dick still hard and begging for attention. I grabbed his dick and inspected it like I had wanted to the first time. His foreskin covered all but the tip of his erect cock. His dick was not as big as Jimmy's, but it was just as fascinating and erotic to me.
I slobbered like a hungry dog as I moved my lips up and down his dick. I stared up at him, smiling with my eyes, surprised at how easily my inhibitions had evaporated. He looked down at me with an intense look on his face.
"I'm going to cum," he declared, his eyes meeting mine.
I took his dick out of my mouth and jerked it playfully. I opened my mouth and stuck out my tongue. Bullseye! The first load of his cum dropped heavily right onto my waiting tongue. The second spurt was much harder, hitting the back of my throat. The third dribbled onto my tongue again at which point I sucked his cock for a few more seconds; sure to get every last drop.
As Kevin left the room I basked in the head rush of my sexuality. I pulled my shirt up and as I walked to the living room I glanced at the clock.
It was only 1:35pm.
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I returned to the living room and we continued to watch tv and talk as if nothing happened. Other than my nose running occasionally, there was nothing to indicate any bad behavior had occurred. We were just three friends drinking and watching basketball.
A few of Jimmy's friends came and went. By a few, I mean three or four and none of them stayed longer than an hour. It seemed as though Jimmy was less popular without Kat around. I could see why. He was a bit of an asshole. He was an acquired taste.
Although we weren't talking about it, my mind kept drifting back to tasting Jimmy... and Kevin, a few hours earlier. A few months ago I would have felt self-conscious about what had just occurred. Now I found myself empowered by it. Whether it was my maturation, the gained experience, or the cocaine, I was becoming more comfortable with my sexuality. After having only had sex with one man for the four previous years, I had now had sex with seven men in the matter of six months - not counting my ex-boyfriend. My sexuality was no longer stifled and I craved more.
To be honest, I enjoyed the attention. Sex was validation that I was desirable, popular, accepted; all things I wanted to be. I was also enjoying the sexual variety my life had been lacking before. I had listened to friends recount their various experiences; hook-ups, men, dick sizes. I had always been jealous but also comfortable with my (then) boyfriend. I could now join that conversation.
Speaking of conversation, there was plenty of it amongst Jimmy, Kevin, and myself. I found that I became quite talkative when high, not to mention unfiltered. Jimmy and Kevin didn't seem to mind. They were unfiltered themselves despite taking much fewer trips than myself to the bedroom mirror. I hadn't been back there too much, just enough to keep the high riding, but I had noticed neither of them had kept the same pace.
Kevin had gone to his room for a bit, or the bathroom, I'm not sure. I missed his company which was weird since we weren't even really friends. My mind jumped all over the place like static in my head. Was he ok? Is he sleeping? Is he masturbating his uncircumcised dick? And why did I care?
"Are you ok?"
Jimmy's question had snapped me back to reality. I assured him I was but I needed some fresh air.
I stood up and walked to the small sliding glass door which led to an equally small balcony; stepping on and over the air mattress as I did. The sun was starting to make its descent and the colors of the setting sky and fresh air calmed me a bit.
I walked back inside to find Jimmy laying on the air mattresses. I stepped over him but he grabbed my ankle, causing me to lose balance and drop to the air mattress as well. I attempted to get up but he playfully tackled me, his weight on top of me sinking us both into the air mattress.
His hands once again found my breasts. He fondled them with a smile. His hands felt good on my body and the attention was nice. I could feel him growing against my pelvis.
"I thought blow made it hard for men to get hard," I inquired.
He sat up, saying nothing, and positioned himself between but not on my legs. He unbuttoned my pants and pulled them off of me as I bent my knees up to assist. He then pulled off my panties in the same fashion.
His fingers found my vagina. Slowly sliding in two fingers.
"I thought blow made it hard for women to get wet," he quipped back, obviously a reference to how wet I had quickly become.
Jimmy took off his pants. His beautiful cock looked mostly hard but not fully. My observation was correct as he entered me with a less than a fully hard penis. This would not do.
I rolled him off of me and onto his back. I laid between his legs, taking his semi hard cock in my mouth and attempting to suck it to life. My tongue and lips worked on Jimmy's dick but not to the point of getting him fully hard.
I had been sucking Jimmy for a few minutes and took a break. My hand still held his penis as it remained right in front of my face. Jimmy may not have been my favorite person but his penis was my favorite penis. I gave it a kiss to show my appreciation.
Jimmy's hand found my head and pushed it down to resume our fun. As my head rotated down I found Jimmy rolling his legs back simultaneously. His balls and asshole were now staring me in the face.
I licked Jimmy's balls but another push of my head indicated that was not what Jimmy desired. I had never licked an asshole before and had only just recently experienced the joy of receiving a rim job.
I decided to take the plunge. I spread Jimmy's ass cheeks and licked his asshole. It was hairy. It had a scent. It was exactly what you would expect of a man's asshole. My brain was trying to register whether this was gross or erotic.
My tongue danced over and around his asshole. His hole seemed to breathe and have a life of its own. One moment it seemed to be winking at me. The next moment it seemed to be opening up, inviting my tongue inside. I had never seen an asshole up close like this before and it was a bit disturbing. I closed my eyes and licked the length of his ass crack - his hole winking at my tongue as it rode by.
I moved back and plunged my tongue into his hole, orally exploring his tunnel. His balls rubbed against my nose while he jerked himself off. I spread his ass cheeks more and pushed my face in deeper - unsure if this was even how one was supposed to toss a salad.
From my position, I looked up and could see he was fully hard now. I wanted it.
I climbed up on top of Jimmy and went to mount his hard cock but I had become dry. I tried fingering myself. Jimmy tried fingering me. The wetness had not returned.
Jimmy stood up and walked nakedly to his bedroom. He returned with a bottle of lube. "Of course he had lube," I thought to myself.
I got on all fours, my hands and knees on the floor for all intents and purposes, as the air had been slowly leaking out of the mattress.
I felt the coldness of lube as Jimmy rubbed a handful of it onto my pussy. He pushed into me, his big dick filling my vaginal cavity. There was no warm up. We had to strike while the vagina was still lubed and the dick still hard. Jimmy was pounding hard and fast. His big dick causing me to moan loudly as it stretched areas previously untouched. It was a welcome, good pain.
I then felt another sensation of coolness. This time Jimmy had squirt some of the lube directly onto my asshole. I froze, knowing what was about to happen but allowing the event unfold like a spectator, rather than the participant I was.
I had tried anal sex before with my ex boyfriend. The first time was horrible but the second time somewhat pleasurable. He was only 5" long though. Jimmy was 8" and much thicker. I was scared and went to mutter an objection but none came out.
His cock head pressed against my hole. My ass was tight, nervously tensing. He pushed forward regardless. I felt his thick head enter me first. He did not thrust in hastily as my ex had. Instead he slowly pushed his thick cock into my ass despite by hole's natural reaction to tighten up and block all entry. He had broken the barrier. His thick cock was now in my ass and he held it there.
"Ow, ow, owwww," I cried
My body was calibrating this new feeling. It hurt so bad and we still hadn't begun the actually fucking. He pulled all but an inch of his dick out slowly. I could feel my ass muscle gripping Jimmy's cock for dear life - the exact opposite of what it should have been doing. I put my face in my hands and cried and he pushed his dick back into my ass. He was way too long and thick for this I told myself, yet didn't mutter anything other than cries and gasps.
Then, as if a switch was flipped, my anus relaxed. The muscle loosened and Jimmy could feel it. He began to pump, his dick stretching my ass. My stretched ass now welcoming it. The lube was doing its job as he smoothly slid it and out of my ass. It still hurt but it was transitioning to a pain/pleasure dynamic, if there is such a thing.
He pumped harder and harder as I reached between my legs and rubbed my clit. I could feel a wave coming within the depths of my body and it crashed with what I'd call the most intense orgasm I had experienced. I was crying - half pain, half orgasmic release. My body and brain were in a blender of sexual stimulation.
Jimmy continued fucking my ass. He was lasting a long time and the pleasure had begun reverting back to pain. He was pumping hard and fast, attempting to bust through the cum damn which was built up by the cocaine and alcohol.
He then stopped and pulled out of me. I could feel my ass was still open and I now I could feel his cum dripping out of it. I rolled over onto my back - my asshole still open and hurting. I wondered anxiously whether he had damaged it.
"Holy shit," Jimmy said, "no one has ever let me fuck their ass before."
"Lucky me," I whispered to myself.
I walked gingerly to the bathroom, in pain with each step. I sat on the toilet and let more cum drip out of me.
A watch sitting on the vanity showed 5:30pm.
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