Roomies Pt. 05 - Final

Ray was good to his word. Two months after the October afternoon where we'd had Italian and talked about the future, he'd bought two tickets to Adelaide, had reserved a vehicle rental and looked into purchasing camping gear. "Sixteen and a half hours to get to Uluru?" He'd started to use the indigenous name for the place after the first 'suggestion'.

Our situation had continued to progress. We were still ganging up on Kate regularly. We'd hooked up with Naomi twice during her trip back home for Winter break.

We'd had several encounters with Cora...the giggler...that were somewhat interesting. She was reticent the first time, until she saw Ray and I begin to service each other. Naked, Cora was something else. I mean, hourglass is almost an understatement. Clothed, she looked somewhat frumpy. Yes, big tits; Yes, big ass, but when she took her clothes off it was staggering. Her breasts weren't just big, they were enormous, each one bigger than her head. Her ass was wide and perfectly balanced her chest, with a waist that was almost tiny. Our first time had been a calm, reserved thing. The next one was a raucous, laughing, hysterical encounter full of hilarity.

We'd met up with Paul, Val, Dom, Dave, Cory and Gregory at the first two's condo three times Paul and Val had decided to make themselves a 'thing'. I'd gotten to fuck Paul for the first time, I sucked off Val for the first..so far only..time. Dom was never interested in me, he liked Gregory and Cory, the young guys. I'd also been able to fuck Cory and sucked him off twice. Dave was...weird. Nice guy, but a bit standoffish when it came to me.

Every night we were in the house together, we spent the night together. Ray spent the first two weeks easing the smallest plug in and out of my ass. He worked the next one over the next couple weeks. It went like this until this week, just before Christmas when I was now plugged up with the largest one.

It was the deepest one yet, 7" from the flared base to the tip, as big across as a Red Bull can. It had only taken him about 20 minutes of rimming and prepping to get the thing fully inside. "You did it! You actually did it!" He yelled from between my legs, "A-Fucking-Plus!"

Ten minutes later with the thing still inside me, I was standing at the foot of the bed unloading my balls into Ray's ass. His own semen covered his chest and stomach as I bent over to kiss him, smearing it between us.

A few minutes later I removed the monstrous...to me...thing from my ass. I twitched, hard as it happened. Ray was particularly happy with my innate ability to stay hard with a plug inside. "Going to be soon, what do you think?"

I'd been kind of anxious for Ray to fuck me for a few weeks now. The night he got the second largest in I'd been just hoping things would work out and that would be the night. It wasn't. That was two weeks ago. He'd said that he wasn't going to do it until I was ready. "I won't until I know it's going to be pleasure for both of us."

Christmas week came and went with little fanfare. We spent it together, a small, intimate affair. We had a fire on the TV, wore special comfy PJ's, traded gifts. I gave Ray three pairs of specialty riding gloves, the kind he usually wore, but with his initials and the logos of the bikes branded onto them. Ray gave me a gift certificate for riding classes, something I'd commented about a few weeks after we'd cemented our relationship status that I'd like to learn how to ride, maybe get my own someday.

We had a good time after that, right on the living room floor. Sixty-nined, screwed, cuddled. We ended up in bed sometime around midnight.

The next morning we were chilling out on top of the covers. Ray had kept the room warm most of the time, so we were both comfortable naked. My arm was behind Ray's head and, at one point, I asked him when did he think we were gonna go all the way, "Soon, I promise. I just want yours to be way, way better than mine."

We'd casually talked about our sexual histories but I'd never hit him up about 'first times'. I asked him.

"Ha!" He threw his head against my arm, "First time with a girl? High school. It was absolutely miserable."

"How about with a guy?" I asked.

He sighed, loudly, "That's...that's another story." He rolled onto his side, "I was a freshman in college. I'd gotten into the frat, right?" I nodded, turning to look at him, "So my roommate was a pretty laid back kind of guy, Junior. Super nice guy named Teddy."

"One night, Teddy goes out on a bender, comes back and is chilling out with a bottle of vodka. We start drinking and he decides to bug me, asks me if I want to fool around. I told him I didn't know what he meant. He whips out his dick and asks me to blow him." He sighed again before continuing.

He looked directly into my eyes, "When I said no, he said either I could suck his dick, or he'd tell the frat brothers I sucked his dick. So...I sucked his dick. It's pretty apparent that I had no desire to do so at the time. He was filthy, he'd been out partying all night. He was stinky and gross. He smelled like piss and sweat. But I sucked him off. He had whiskey dick, so nobody came."

"I couldn't get it out of my head though. I mean, I'd hated the situation, hated he'd backed me into a corner, but the feel of him in my mouth, the sensation, everything but the smell had been more than just a thing, it'd been. Fuck, I don't know, exciting." He turned back to look at the ceiling.

"Two nights later he did it again, this time he was sober. This time he came, without warning in my mouth. I was disgusted by it, but I had a fucking hardon like nothing you can imagine." He looked back at me, "A week later he fucked me. He was...well, he was about a half inch longer than me, but your width and shape...I mean, he was like a half inch shorter than you. He was rude about it, I hadn't prepared myself, it hurt and I hated it. It took my two years and another guy for me to realize I got a hardon from getting fucked, not getting forced into it. After that, I just learned about myself. Here I am ten years later, loving men and women."

He rolled back to the look at the ceiling, "Well, loving 'A' man nowadays."

I turned towards him and kissed him.

Our work week got started the next night and finished on the 30th. He'd had all day off and when I got off at 7 pm that night, Ray met me at the door, "Let's go to the store, we're having a get together at Paul and Val's tomorrow night and we need to get some supplies."

We got snacks. We got drinks. We got the biggest bottle of lube I'd yet seen.

We arrived back at the house about two hours later. We put what we had to in the fridge and put the rest in a box near the door, including the huge bottle of lube.

About ten o'clock Ray cracked open a bottle of wine and said, relaxed, "So...you're prepped, right?" It was his typical question when we were going to have a work-in session, and I'd figured we might be into it so I had gotten myself ready.

He asked me into the room about twenty minutes later. There was a wedge-shaped pillow on the bed, covered in a towel. We'd used it on a few occasions when I'd fucked Ray and a couple times when he'd worked on me with the plugs.

"Who's getting on there?" I asked. Ray didn't answer with words, he took me in his arms, kissed me hard and pressed me towards the bed. I laid down with my ass up in the air as we continued pressing our lips against each other.

He moved himself down. He worked himself on my neck and my chest, my stomach and down to my shaved groin.

He began working on my cock. I'd gotten used to his technique but still found myself baffled that it was still this good, every fucking time.

I just enjoyed his work, how he'd only periodically take me into his throat. It was more for his satisfaction than mine, I'd told him I wasn't into the moments when I went that far, but I wasn't 'not' into it either. He kept his action back and forth on me for a few minutes, finally moving off of me to roll my balls in his mouth and then down around my ass.

This was how he worked when he was beginning to push one of the plugs into me. I was prepared for it, I'd known he was probably going to get into things tonight. He'd been giving me the eye all day.

His tongue flicked in and out of my asshole, and I repetitively flexed my sphincter at him while he did it. I'd like to say I'd gotten a bit less susceptible to this as well, but that was a lie. It was just as exciting every time he did it.

I was waiting for the momentary break where he'd grab the lube and the plug but instead of his regular circuit, he moved up to me and began kissing me deeply, running his tongue in and out of my mouth, along my teeth, down to my neck. His hardness pressed against mine as he ground himself into me.

He'd done it before and it always pulled more precum out of me than anything else. It was a blast. We were both shaved, I did it every morning before I went to work, Ray did it when he got home before he laid down. There was the tiniest amount of stubble that just helped with the intensity of it.

We went like this for a short time, my arms around Ray, his hands at my head. I'd done this from almost the first time we were together but now it wasn't me holding him because I should, I was holding him because he was mine. I hadn't written it down, hadn't told him as much, but it was how I felt.

He slipped a bit lower than normal, his head pressing against my balls. The slimy fluid he was pushing out made me gooey in a way I thoroughly enjoyed.

This went on for a few amazing, phenomenal moments before he sat back up on his knees. I looked up at him looking at me, that face he gave me that spelled out the same feeling I had when I wrapped my arms around him was all over his face, but this time there was a slight difference.

"I wanted you to want this. I needed you to want this. I need you to tell me this is what you want." His eyes were moist, "You know I want this, I've wanted it for ages. I need to hear you say absolutely that you want it."

I understood what that meant. He hadn't had the opportunity to say it. He needed me to say the words. "I want this, Ray. I've been wanting it almost as long as you, I think."

A moment later, after months of waiting, of preparation, I felt the fat knob of him press against my ring. Like he had always told me, I bore down. The lubricated end of him pushed in just the smallest amount and I gasped, partially out of surprise at how easy it had been, partially about how I could feel, actually 'feel' the texture of his erection with my anus. Up until now, I'd only had his fingers and the plugs inside me. I was so familiar with his cock, having held it in my mouth so many times, I realized I could feel the textures I knew with my mouth.

He pulled back the slightest bit and pressed inside again just a touch. It still felt amazing. He pressed in another half inch or so and it sent a shudder through me. "Are you ok Joe? I didn't hurt you, did I?"

I took a chance and squirmed down a hair, getting another quarter inch or so into me, "No, babe, no. It was fine. Please keep going." I'd taken it a step further now, beyond dude, bud, bro. This one MEANT something.

He pressed further, almost losing his cool for a second. I loved it. "You...you feel so good. I knew you would, but...oh...oh my god. You feel so unreal." He pulled a touch back, then pushed, "It's so much more...I...what do..."

I could feel his biggest vein, the one I'd spent so much time tracing with my tongue, as he pushed himself further into me, going past the fourth inch. It was as I was concentrating on that vein that he hit my prostate for the first time.

It sent an electric shock through my body, starting at the knot inside my ass, flowing down my legs, up my spine to my head, rocketing back down and to the end of my cock which pulsed in the air, as erect as I'd ever been. I looked down at me and saw a huge blob of clear fluid flop out of my slit and roll down my head.

He slid along my prostate now, entering me to maybe five inches. "Are you still...still OK?" He asked, hesitantly, with a quivering that denoted something like his patience was fighting his need.

I decided it was time. My hands went to his asscheeks, meaning I had to lean forward just slightly. He watched me as I pulled him, just yanked him inside me, all the way to the hilt. "I'm so, so OK."

He smiled, "Ok, I'm there. Are you still good? Are you still with me?"

I placed my hands on his arms and said, "There's nowhere on earth I'd rather be."

His hips began a slow back-and-forth motion, the first inch of him coming back and forth in easy succession. It was a completely unbelievable experience, the feeling of him sliding against my sphincter, the easy thrumming. I'd never felt anything like it.

On every inward thrust he hit my prostate, driving that insane feeling through me. I thought I might get used to it, but there was no chance. It was the same level of amazing every time. It didn't ebb, it drove me nuts and almost every time, a shot ran through my prick and a drop or two of precum would come falling from me.

He began a different sort of pace after just a few moments, shuddering as he came out, shuddering as he went back in. I looked at him, dead in the eye and said, "Lover, you can do it. I want you to do it. I want you to go as fast as you need to. As hard as you need to. I'm here, be here with me."

That second he leaned forward onto me, planting his mouth on mine and beginning an earnest motion, pulling some four or five inches out every time, burying himself until I felt his balls at the back of my asscrack. Their bald slickness left a wetness that would cool for a split second before it was back on me.

He moved his mouth to my ear, "I just...oh god...I just needed...fuck god fuck...I think I...I might."

"I love you too." I said to him, moving my mouth to his.

He wrapped me in his arms, holding me close as he kept a slow but intense pace. I lost track of time there, wrapped up in him in a way I really hadn't been...ever...in my life.

At some point, somewhere just before he pulled his mouth off of mine, I came. I spasmed erratically, both at the pace of my body and at the pace of his thrusts shooting gouts of semen between us, on my belly and his.

"I'm going to finish. I'm going to cum...cum inside." And as soon as he said it, he pressed forward a final time. He swelled and pulsed inside me, thrumming against my still stressed ring.

I had the strangest sensation. It was like I was cumming again as he vibrated against my prostate and asshole. It wasn't like a typical orgasm. It was unlike anything I'd ever felt, pushing my brain into weird almost passing out point, seeing stars. "Oh...oh fuck fuck oh god." I just breathed it.

"Please, baby, just ride it. Just ride it out." He bit into my shoulder, still buried into me.

A moment or two later he sat up. The fine belly hairs we both had pulling away stickily. He groaned, "Oh Jesus. I've...Oh my god..." He leaned down to kiss me quickly and sat back up, "That's one of the most amazing things that's ever happened to me."

I stretched below him with him still balls deep, "Me too. I can't imagine there's a way it could have been better."

He leaned back as far as he could, his muscular chest flexing as he stretched his arms above his head, running his hands over his hair on the way, "You feel so good. I mean, it's the way I hoped you would, the way I'd just..." He looked back down at me, bringing a hand along my chest, my abs and where my cum had coated me, drawing a finger through it and bringing it to his lips, "...I just...I don't know. I mean, man...I"

He sighed loudly and said, "I've never said it before...I Love you. I really, honestly, completely fucking love you and I've said it before but I never meant it and I mean it now and I'm inside you and I don't ever want to leave! You make me feel happier and more alive and you inspire me and oh fucking jesus. You know?"

I wrapped my legs around his waist, pulling him into me more, loving the fullness of him, "I know. I'm riding that wave with you, babe."

He snorted in a chuckle, "Babe...fucking 'babe'. How goddam hot is that? How unbelievably amazing and hot and tremendous is that."

"Pretty" I said.

A moment later he hadn't lost his erection and began moving himself in and out of me again. It was more playful this time, more relaxed. It was still amazing, but it wasn't as intense as before. It still FELT as intense, but the mood was less severe. It was still fantastic.

Sometime later, he came again. Shortly thereafter he pulled out of me and I felt, for the first time, what the 'soreness' people talked about was like. It was a warm, used feeling. I enjoyed the feeling and missed him being in me. Something followed him and rolled out and was warm as it oozed down to the towel under me.

I woke up the next morning in the opposite positions that we'd been so many mornings. His cock traced a cool, wet line on my right asscheek, coming from my crack down. His arms wrapped around me as soon as I stirred, "Happy New Years Eve." He said into my ear in a growly, just-woke-up baritone.

I cuddled backwards into him, "Love you too."

That night we went to Paul's house. The regular crew was around and I had the second cock of my life up my ass, Dave's much more average sized dick. We rang in the new year with Ray sitting on the couch and me sitting on Ray. As the countdown roared we planted our lips together and he flexed inside my rectum.

He'd cum a bit later into my ass. It would be the first time of the year. The first time of dozens and dozens. Some nights we'd finish inside of each other in random order. We ended up on the same shift and we'd do it right before we left for work. Sometimes at lunch. I was buried inside him the morning we arrived at Uluru, and the morning we looked at the Tasman Sea for the first time. He was inside me the first morning we woke up in Rome and in our hotel in Florence.

Our relationship continued with Naomi and Kate, with Cora and a few new girls, sometimes one night stands and sometimes a couple times. We also had a few random hookups with guys, invited a new couple into the group, said goodbye to Val and Gregory, who went off to new horizons.

Four years later we had matching rings. I'd never look back again, not after the wedding or the cross country motorcycle trip or the day when Naomi gave birth to our daughter.

We still call ourselves 'Roomies' from time to time. Just for laughs.