Round Two 4

The second round always makes or breaks the relationship. After 5 years of sexual tension, a few hours out on the town, and some illegal substance we had finally scratched the itch that had plagued us for so long. Another 5 months later, we started feeling that itch again.

Through flirty text messages where I told him my bed was cold and needed it to be warmed up, to him seductively nibbling on my neck at the bar over a game of pool, we finally whittled down a time for us to rendezvous at my place. It was a quarter till midnight and freezing cold. I walked down to meet him in the parking lot since he had forgotten which door was mine since he was last here.

"Nice pants," I said, looking at the beer mugs brimming with yellow and white froth that were printed all over in a gaudy pattern. "You look like you're dressed for a sleepover."

"Yeah, these are my beer goggle pants," he said with an enthusiastic grin. Spattered across over and over is some phrase about going home with someone due to intoxication, but I couldn't be bothered to store it in memory. I'm almost certain that he's had these pants from his early fraternity days. He'll be 27 in May.

We went up the stairs. I felt his eyes heavily on my ass as I walked in front of him. Strategically I put a little extra into every step I took, a little extra swing of my hips as I lifted my feet to every step and keeping his face right where I wanted it. I could feel his hands aching to stroke my curves. Once inside, we quietly stepped into my bathroom, what separated the foyer from my room. I held my finger to my lips, signaling that my roommate was asleep in the other bedroom.

I closed the bathroom door after him, and we moved into my space. Music from my stereo was in place to hopefully mask the noises that would soon follow. Tonight's playlist was Silverstein. "You look like you're getting ready to study," he said, motioning towards what I was wearing. I was tempted to answer the door in nothing but my college sweatshirt and maybe some boyshorts, but since I had to meet him downstairs that plan was thwarted. Instead I stood before him, college hoodie, rolled up boxers exposing the bottom curve of my rear, and my chunky black Dolce and Gabbana glasses. My long shaggy blond hair messily pushed over one shoulder. We both knew what he was there for. This wasn't a fashion show.

"Not like at the bar the other night at all. But," he said as he slipped his hand down my thigh, "I'd know that ass anywhere." His hand came back up, under my boxers, and gave my right cheek a firm squeeze.

I took the zipper of his own jacket in my hand and slowly but sternly yanked down on it. I kept my eyes on his while I parted the now separated black fleece to run my hands across his chest. At this point I started feeling less anxious and more relaxed. I didn't have to work for this; I already had it. I moved in to kiss him as I stroked his lightly defined athletic torso, feeling the light scattering of chest hair against my fingertips. He wasn't like the boys I had been with before. He had a rugged masculinity about him, from his demeanor to his facial hair that he had sported the entirety that we had known each other. I took comfort in his manly charm. This was no prepubescent boy I was about to fuck.

As I moved my hands up his pectorals, to his neck, and through his hair I took notice of the scents and sounds. My mind was trying to take it all in- anything needed to get me fully aroused. Unfortunately, the only scent I took in was the aftermath of his shower. Someone apparently uses Irish Spring, or some other version of cheap male-demographic bar soap, I thought to myself. It was no Abercrombie Fierce, but I forced myself to go with it. I listened to his breath quicken and the soft moans escaping from deep in his throat as we began kissing harder. I tugged his jacket off and slipped my hand between the elastic of his beer goggle pants and boxers. As the pants fell to the floor, his growing erection sprang upwards, free from the layer of clothing that kept it downward. I brushed the thin layer of cloth that sheathed him with my palm. He took his hands from around my waist and to the bottom of my hoodie and lifted upward. My hands went to my back and I undid the clasp to my bra, slid it down, and tossed it to the floor. I pushed my boxers to my feet.

My forwardness turned him on, and the soft light coming in from my window illuminated his glistening tongue as he took one of my stiffened nipples into his mouth. His hands ran from the natural curve of my breasts down to my thighs, much like tracing out an hourglass shape in the air. He sucked and lightly nibbled on them, paying attention to caress each of them evenly. His head came back up to meet my mouth, and we took a step or two back towards my bed to get into a more horizontal position. He started to breath heavier and heavier, turning into a drawn out male parody of a porn star. It bothered me the last time we hooked up but I was willing to overlook it. Besides, I never had been with a guy as vocal as him and it was a turn on the way he would say my name and cuss in between panting.

His hands found their way to the waistband of my panties, black boyshorts to be exact. His mouth and beard grazed the side of my neck, sending me into goosebumps and shivers as he slid my panties down to my knees and over my ankles. He began moving his mouth southward, taking long strokes with his tongue followed by soft kisses. Down my chest, over my belly, and down to my thighs he went before taking his tongue to part my lips between my thighs. He greeted my dampening pussy with a calm familiarity. Nothing new here- he knew the delicate metal barbell that I have piercing my clitoral hood. He played with it for a bit with his tongue before taking the tip into long wide strokes around my clit and to my opening. He fucked me with his tongue, sucked on two of his fingers, and drove them inside of me. He took his mouth and moved it back to the piercing. I gave out a gasp of pleasure, letting him know that he was hitting the right spots with his tongue, and that his fingers were the icing on the cake. My back moved up into an arch and he bent his fingers inside me to rub against my g-spot.

He continued this licking and rubbing for a few minutes. It felt great, keeping me on the cusp of coming. I was a little disappointed each time he would near pushing me over the edge because it was like he was distracted by another great idea he could do with his mouth. I started trying to guide him with my voice. "Oh my God, right there," I would softly moan, and I'd contract my muscles around his fingers, begging for him to continue what he would be doing. Then, as if seeing a shiny object off in the distance, he would switch gears and start doing something else. Eventually even the shiny objects didn't hold out, because after another five minutes he removed his hand from my cleft and crawled back up my body.

He sprawled out on his back with his erection in the air, obvious as to what would happen next. I sat up, pulled my hair over one shoulder, and positioned myself in between his legs. I spit into my hand and worked it over his shaft. He scooted his legs a little wider and wiggled his toes in anticipation of my mouth that would soon be joining my hand on his member. I had been slightly reluctant to sleep with him again, since the first time we had sex I felt deflated over his size. Now I found myself thinking, OK, this isn't as bad as I thought.

I gathered up some extra saliva in my mouth and bent down to meet his shaft. I sucked on the head a few times and traced circles with my tongue before moving my hand in unison with my mouth up and down its entirety. He started to whimper immediately. Silverstein was having a hard time covering anything up. At least when he was eating my pussy, his mouth was full and I could be the vocal one. The tables were turned, and I couldn't do anything but listen to his oh's and ah's until he signaled for me to sit up about two minutes later. Usually I give the guy I'm blowing a break to regain his composure and then dive right back in, but tonight I was on a bit of a time crunch as well as hoping to get off.

He reached for a condom and rolled it down his glistening erection. I like to start fucking on my back in good old missionary, but since he was not a member of the Seven Plus Club I figured I could start on top without risking the initial tightness I feel as my vagina slowly loosens up to take in large dick. His girth made up for his shortcomings- I could feel my lips giving slightly to the width of his cock as we slid on each other. I pushed my hair back and began massaging my tits with my hands- a striking visual for him as he lay underneath me. I rocked my hips back and forth as his hands wrapped around them. I would speed up my movement, then slow it down to keep him in check. His moans let me know exactly when to do this.

He sat up as I straddled him, and took my left nipple in his mouth. He was more aggressive this time around, nibbling harder to the point where I had to give a soft, "Easy," as I bounced up and down on his shaft. If he was too forceful, he would gently lick the sensitivity away before teething on it again. Eventually we rolled on to my back, and he bent my right leg up to my ear. He pounded himself hard into me over and over until the condom began to dry out. He removed himself and I spit into my hand to use as additional lubrication. Once well moisturized, he plunged back into me. I breathed deeply and in sync with the thrusts of his ass into my new wetness.

He pulled himself out of me after a bit. I rolled on to my side and cooed, "Are we taking a breather?"

"Do you need one?"

"Not really."

He rolled me from my side on to my stomach. His hands drifted from my back to the curve of my spine. I looked over my shoulder to see him scooting down towards my ass, a sloping mound of muscular flesh that he was eying with anticipation. I arched my back, pushing my belly into the mattress and my bottom more into the air. I felt his fingers travel along the smooth arc of my cheeks. His tongue soon followed.

I grabbed the pillow that was in front of me and clenched it to my bosom. I felt his tongue make its way into the crevice of my ass and start to stroke my hole. The idea of rimming is still one that I'm getting used to. I've found that only guys that are above the age of 25 are in to this act, so I relaxed and went with it. I enjoy being with a guy that pushes my boundaries a bit. It feels sexy to me to be the one dominated, the one being taught a thing or two. My muscles loosened up and I allowed my voluptuous ass become putty in his hands and mouth. He sucked on a finger and he slid it into my pussy, all while he continued to lick my asshole with his tongue. I anticipated that he might make me come in this fashion. I waited with bated breath as he slipped his muscle and his fingers into me, but all of this is to no avail.

Once again, he removed himself and sat up. I felt him kneeling behind me, cock in hand, and inching himself towards my asshole with its tip. "Hold on a second," I said as I reached for a small bottle of lubricant that I keep in the nightstand. I handed it to him, and after a few seconds he is ready to go. He unsuccessfully tried to find my anal opening, and rather than try to coach him verbally I took his dick in my hand and guided it myself. He inched slowly inside me, and I instantly felt that he has not had much experience in this department. Not that I have either, but I know enough of what I do like so I gave him a few guidelines. "Slowly... Slowly... Let me warm up to this. Careful not to pull out too far." I heard him let an OK slip out from his mouth, and he kneaded my ass with his hands and cautiously started to pump his cock into me. I sensed his apprehension, like he almost couldn't believe that I'm alright with him doing this, like I'm some otherworldly chick sent from above that actually lets a guy fuck her in the ass- even guides his dick in with expertise. His moans grew more and more obnoxious. He was really getting off on this.

I took a few deep breaths, and my muscles started to relax so he could come into me with ease. I began to be very turned on at this point. I felt a wash of warmth and dampness flood into my cleft as he slid his member into my rear over and over. I brought my fingers to my mouth and moistened them with my tongue. I moved them down to my slit and began to rub my pulsing clitoris. It was so slippery it was difficult to get a good grasp on the spot that I knew would ultimately bring me to climax. He brought one of his hands around and thrust two fingers into my pussy.

Oh yes, I thought. This is the shit that is gonna make me come.

I found myself back at my old friend the cliff, the verge of bucking with my back and screaming into a pillow for more and more. I plunged him inside me deeper and deeper by throwing my weight backwards and on to his erection. I massaged my engorged clit and piercing. He was getting close to blowing his load, I could tell. His hand removed itself from between my thighs and rested on my back. He tugged on my hair a little bit and he said, "Yeah, you like that? You like how I'm fucking you?"

I looked over my shoulder so I could get him into my peripheral vision. "Yeah, fuck me harder," I managed to get out, his pumping allowing the words to escape from my mouth.

"You like it when I fuck you in the ass?"

I wanted so badly not to sound generic, but in this case there really is nothing else you can say. "Yeah, baby, fuck me in my ass."

"Ohhhhh God, where do you want me to fuck you? Say my name."

I kept calling for him to fuck me in the ass. Over and over. I started hoping that my roommate really was sound asleep. His thrusting became more and more intense. I felt his hands gripping harder and harder on my hips. I wasn't going to reach climax by the time he did. So I let my hand fall from my warm wetness and grip the pillow as I braced myself to take him in.

After a few more shoves with his hips, he bent over and a drove himself to climax. Jaded, I felt his weight on my body and he cried out for me in muffled tones. His orgasm lasted briefly and after he finally came he laid on top of me, breathing heavily. It was quiet in the room except for the sound of one song ending and another one beginning. I said, "Oh, cool. You finished just in time for my favorite song by Silverstein." He removed himself from my asshole after another few awkward seconds and I started looking around for my phone. He stretched out next to me and draped his arm across my bare back. Aww, he wants to cuddle, I thought. "At least you have good taste in music. Its better than that Fiona Apple shit I usually have to listen to when I'm boning some chick."

***

He stayed the night. I've become accustomed to the guys leaving, generally at my own accord, after the condom hits the trashcan. I got into the shower alone, the way I wanted it. I lit some candles to keep the lighting low as I washed the lubricant from my pussy and my ass. I used my winter floral body wash to remove the cheap masculine soap scent of his from my skin. Later, as I pulled on my hoodie from earlier, I realized there was no escaping that odor and that I would be sleeping with it embedded into my clothes. I allowed him to spoon me. He fell asleep instantly, and I struggled into a slumber with the stereo still going softly in the background.

We woke to the sound of our cell phone alarms going off, alerting us that it was still only Friday and we both had work to get to. I offered to make breakfast, but he said he had to go. That didn't bother me. He threw on his jacket from the few hours previously, kissed me goodbye, and left. I couldn't wait to get into the shower and to throw my hoodie and sheets into the washing machine. Round Two sex changes everything.