My Gay Ex-Roommate Pt. 03

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His relationship with his ex-roomie is changing in new ways.
5.8k words
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Part 3 of the 4 part series

Updated 06/09/2023
Created 06/09/2018
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Over the next week, my brain kept exploding a little when I remembered what I had done at Alan's place. It was a huge distraction as the feelings, smells, and tastes flooded back in and pushed everything else out of my mind. I was surprised that while there was a sort of awkwardness about it, I didn't feel conflicted or ashamed or hung up that I'd had sexual experiences with anonymous men. In fact, having gone through it once, I was incredibly eager for more.

Although I tried not to sound too eager as I texted Alan during the week, on Sunday I would find that Alan had apparently been eager as well. As soon as I came in and stepped into the living room, he made a gesture at me. "Get undressed," he said. Well, fine. I complied without complaint, pulling off my clothes and making a pile in the corner of the room.

"Spoiler alert," he said as I was finishing. "You're getting fucked today."

I felt a weird kick in my solar plexus, but this was exactly what I'd been fantasizing about all week. He tossed something at me and out of instinct I caught it. It was a plastic bulb with a narrow nozzle at one end.

"Go in the bathroom and clean yourself out," he instructed. "Warm water works best. There's some lube on the counter."

My fantasies has not extended to this detail, but I understood the sense of it. I headed to the bathroom and it took me a few minutes to work the process out - pulling out the nozzle, filling the bulb with warm water from the sink.

"It'll probably work best if you squat down at first," Alan called out as I heard the football game in the background. I squeezed out some lube onto my fingers, squatted down on the floor and rubbed it over my asshole. Then I grabbed the bulb with my other hand. The nozzle slid in easily enough. I squeezed it, and was surprised when an air bubble expanded into my rectum, like a fart in reverse. But then I could feel the water spraying inside me.

I squeezed as much of the water as I could, and pulled out the nozzle, suddenly feeling a familiar sensation in my guts. I quickly sat on the toilet and pushed the water out. I reached behind me and flushed the toilet.

"Do that two or three more times," Alan called out. "You're ready when you just spray out clear water."

I stood up from the toilet a little shakily and went through it all again, feeling some weird sensations as the normal order of things for my guts was upset. To be sure, I sprayed the nozzle into my butt three more times before I dared look into the toilet bowl before flushing. The water was clear.

Just as I felt satisfied with that, Alan walked into the bathroom. "Put this on," he said, handing me one of the leather bracelets I'd worn last weekend. I wrapped it around my left wrist and tightened the buckle before Alan handed me another and it went on my right wrist. And then a third, and I sat on the edge of the tub and put it on my left ankle, and then the last one on my right ankle.

I stood up as Alan was looking me up and down. "You look ready to go." He turned and exited the room and I followed him down the hall.

And now I saw how busy Alan had been getting ready for this. In my old bedroom, the bed had been taken up, and the box spring and mattress were leaning against the far wall. That opened the room up and in the centre of the floor on top of a drop sheet there was something that looked like a padded sawhorse... or one of those things in gym class that you'd do vaults over.

"Get on," Alan said, and following his instructions I bent over it, my belly against the padding. He had me scooch back a bit so my butt was dangling over the rear end of it. The balls of my feet rested naturally on the floor - I don't think it was an accident that this device seemed the exact right height. There were clicks behind me as Alan attached something to the rings on my ankle bracelets. My arms stretched down along the front legs and in a moment, Alan secured those as well. I tried to shift around a little, but there was no way I was going anywhere unless I toppled the whole thing over... and even then there would be no way I was getting myself loose. I was tied down... with my ass exposed and ready to be fucked.

Alan looked me over with a satisfied expression on his face. He walked an entire circle around me, stopping in front of me. He had several objects in his hand, and he held one up. It took me a moment to realize that it was a buttplug. "This will help keep you ready for action," he said. "This is the training-wheels beginner size. They get bigger." he held up a couple more of increasing size before showing me one that looked as thick as a trailer hitch. I shuddered involuntarily as he walked around behind me.

As I craned my neck to try and follow him I suddenly felt a flash of pain as he slapped my ass hard with his open palm. It stung as I winced involuntarily.

As I recovered from that, I heard Alan fiddling with something, and then a slurping, squeezing noise. A second later, something wet touched my exposed asshole, then something pushed against it. There was a feeling of stretching and discomfort that increased - it felt like he was shoving that giant plug inside me, though I knew he was only giving me the smallest one. I breathed in and tried to relax as he held it in place for a few seconds. Then he pushed again and the thickest part of the plug squeezed through with a slurp as it suddenly felt like it was being sucked in.. and then held in place by the flared base.

He walked back around in front of me. "Well, have fun. Remember, just like last week, the safe word is 'red'. You can stop it if it gets to be too much. But if you stop for no reason, it's all over in here."

He walked out of the room, leaving me alone. Once again, there was the mind game of waiting for someone to come for me, and the intensity of my desire was even sharper this time. I noticed the clock on the dresser had been moved so that I couldn't see it anymore, so I had no idea how long I waited. It felt like a long time... fifteen minutes? Half an hour? Once again, time was abstract, and once again I veered between intense excitement and boredom. I explored the interesting variety of sensations that emanated from somewhere behind my belly button as I squeezed the buttplug with my sphincter muscles.

Then a guy came in. He looked like he was in his early forties, well built, bald and wearing a blue t-shirt.

He walked in front of me, undid his belt and dropped his jeans to his knees. Without a word, he pulled his cock out of his jockeys and shoved it in my mouth.

"Mmmmm," I mumbled as I began sucking on it as best I could. I tried to curl my lips around my front teeth, and I ran my tongue along the bottom of his soft shaft. He stagger-stepped toward me, forcing the invader deeper into my mouth. And then I could feel it growing, changing... getting hard. Oh, fuck yes! Trapped under my belly, my own cock twitched.

Strapped in place with my leather wrist cuffs hooked to the horse's legs, there was only so much I could do. I could bob my head up and down a bit on his cock, I could work my tongue (although that became harder to move as his cock increasingly filled my mouth) and I could apply suction. I tried to do all of that as much as I could while also breathing through my nose and fighting the urge to retch or gag. Then I felt his hands gripping my head behind the ears and he began moving my head up and down on his cock. I'm just your fucktoy now, I thought to myself as again I struggled to just keep breathing, which became impossible when his cock was pushed deep in my mouth. I had no control over the situation at all any more... and it felt amazing. All I could do - all I wanted to do - was to serve this man's cock.

And then he pulled it out of my mouth. When it was withdrawn, I couldn't believe how much bigger it was than when I had started on it. It was a very pretty hard-on - bigger than mine, but not so thick as Alan's tool. I only got to look at it for a few seconds before the guy clutched at his pants and made his way around behind me.

I watched as he fumbled with a condom package and opened it, stretching the sheath over his erection. He squeezed some lube on his cock. Then he gripped the base of the buttplug and pulled it out - slowly, but not as slowly as I would have liked. It felt like the plug was lodged in place until it gave and suddenly I felt an unusual emptiness. That didn't last long as the head of the guy's cock was immediately against my asshole. He pushed, and the head of his cock was inside me, entering me much more easily than the buttplug.

He paused, and then pushed further. Unlike the tapered plug, he offered me the steady length of his thickness. It was a little uncomfortable; it was quite delicious. My head was spinning. He paused, withdrew a bit and pushed his cock home. He had entered me.

He was taking my virginity. I wonder if he knew? I wondered if I should tell him... would that turn him on? I was going to say something, but all it ended up being was a muttered much of words, "yerrverr. Mmm."

He was done pausing now - he was fucking me, pushing in and pulling back with steady thrusts. Involuntarily, I tried to flex my arms and legs but they were held in place. All I could do was lie there and take it. And get fucked.

It felt so good. Why didn't anyone just tell me this, how good it feels to get fucked? There was a bit of discomfort as his cock stretched out my asshole, but there was also a lot of pleasure... regular sexual feelings that I was used to, and other strange pleasurable sensations radiating out from somewhere his cock was prodding at. He was fucking me harder now, and I wasn't sure if I was going to pass out or start laughing in joy. Then a familiar sensation took hold, and my balls tugged and my cock surged and I was coming. He had given me an orgasm just from fucking me!

I was moaning, and my sphincter muscle squeezed his cock as my balls pumped out their load. Feeling my asshole tighten around his shaft made my orgasm different than usual and more intense, and I could tell it did something to him, too, as he grunted. He took a breath and paused to regroup for a few seconds, but when he began thrusting into me again it didn't take too long before I could feel his cock throbbing inside me and I knew he was having his orgasm, too. His final thrusts gave me one more burst of pleasure before he stopped fucking me and caught his breath.

He pulled out, and I again felt a vague sadness at the emptiness in the place that had just given me such immense pleasure. I craned around to see him pull the condom off and toss it in a garbage can by the nightstand. He grabbed a hand towel from a small stack that Alan had left there and wiped the sweat off his shiny bald dome. Then he wiped his cock off and tossed the towel aside. He pulled up his pants and did his belt up.

I wasn't expecting it, so I was a little surprised when he returned the buttplug to my asshole. I was also surprised at how much easier it went in this time. Then the guy walked out of the room.

"Thank you!" I called as I realized he wasn't going to say anything to me. I wondered to myself: is it going to feel that good every time?

There was another of one those boring/exciting waits... and this time I could reflect on what it felt like to have been fucked. There was soreness, like you'd feel in any muscle that got a workout after lengthy idleness. And there was residual pleasure, occasional joy buzzings shooting toward my belly button. And nothing to do but wait... and wait.

I recognized the next guy who came in. It was Bert, the chubby guy who had treated me quite tenderly last week, the first man I ever made out with.

"Ohhh, you look you hot like that, honey," he said, sounding slightly agitated as he walked around me. Then behind me, in my blind spot, I could hear him undressing.

His hands touched my buttocks, squeezing and exploring them. And then... and then he kept doing the same thing. It seemed like he was in no rush. In fact, for a long stretch of no-time, his hands explored my body, somewhere in between a sensual massage and a prolonged grope. A lot of it didn't even seem overtly sexual, such as a fair amount of time he spent massaging my shoulders.

It was as if he merely wanted to spend some time touching a man. Well, I guess I can understand that.

But when he went back to my thighs and buttocks, it was indeed sexual, and I could feel myself starting to react to his touches with a renewed erection. My cock was trapped under my stomach, but he seemed to get as much out of playing with my balls as he had last time with my prick. It was certainly doing something interesting for me.

Eventually I could feel him slowly tugging at the buttplug until with a sudden rush it pulled out from my sphincter. I heard him moan and when I turned back to look at him, I could see that he had stuck the whole length of the buttplug into his mouth, his lips wrapped around the thin section around the base.

Then he pulled it out, set it aside, and leaned in to start licking my asshole.

After getting fucked, my hole seemed extraordinarily sensitive, and as he worked his tongue around it - and then into it - it felt totally incredible. And it got even more intense as he kept going, ramming his tongue in my sphincter and then switching back to licking the sensitive rosebud.

Fuck! This is amazing! And obviously Bert liked it, too, as he kept going and going. After a while I could hear him grunt as he made out with my butthole and I could sense, more than see, that he was jerking himself off as he rimmed me.

Eventually, I could feel his body tremble. I opened my eyes and looked back to see him holding his hand to his face, licking his own spunk off his hand. He carefully returned the buttplug to my hole and got dressed. He came around to my head, and leaned in to kiss me, his lips still sticky with his own semen.

"Thanks, honey," he said as he headed out.

This time, there was hardly a wait at all before two guys came in together. They were looked like a couple, a younger steed and a middle-aged daddy, gossiping with each other as they got undressed, almost as if I weren't in the room. They both stood in front of my face, taking turns shoving their cocks in my mouth as I bobbed my head on their shafts, trying to get them hard for the poundings I was now hungry for. The older of the pair, with salt-and-pepper hair, then went behind me, pulled out the plug and put on a condom and was soon sliding his cock inside me. My butthole was a little sore from its previous exercise, but I still shivered with anticipation as he started fucking me.

The other guy, meanwhile, turned around, spread his feet and leaned forward, sticking his ass in my face. It was my turn to give a rimjob now, and given my limited range of motion, I did my best. His asshole was actually quite delicious, and I could see why Bert had enjoyed working my hole over for such a long time.

Eventually, I could feel the hard, driving strokes that told me the older partner was coming, and while he caught his breath, the younger one stood up and put a condom on. So, just as one cock was pulled out of me, another, larger one replaced it.

The older partner had been slow and steady, but the younger apparently had something more vigorous in mind. He drove the length of his shaft into me, and then I could feel him almost climbing on top of me. Rather than just standing behind me and pounding my ass, I could feel his legs wrapping around mine, his ankles hooking inside mine. So, given that his weight was on me and his cock was jammed deeply inside me, instead of pushing forward to penetrate me he fucked me by pulling his cock out and then slamming it back in. So although I'd been fucked twice already, this was something else entirely, and I started to feel like I was going to pass out as I could feel him rooting his cock into me, driving deep into my guts.

It was extremely intense and I thought I was going to once again come without touching my cock, but instead of orgasming, I hit a hitherto-unexplored plateau, a steady peak of pleasure emanating from deep, deep inside me that sent continuous crackles of pleasure throughout my body as he kept rutting into me.

And then his frenzied strokes, stabbing into me with such force that I felt a little uncomfortable as he headed into his own orgasm. His hands gripped my shoulders as he pulled himself into me as deep as he could reach and I could feel the length of his shaft spasming inside me. I felt pain and fireworks all at once and then he was still, catching his breath for a moment before he untangled himself from me and climbed down.

And then, they were back to gossiping as they dressed and prepared to leave. I was ignored, a fuck-toy not even worth acknowledging. I wanted to be a fuck toy forever.

After about ten minutes, Alan came in and released me. I was sore all over, including in my butt, but again, as I went to use the shower, I was already thinking about next Sunday.

* * * * *

There was no disguising my eagerness when I returned to Alan's house the next weekend. Alan, meanwhile, seemed almost indifferent to me. "Get undressed and clean out your ass," he said as he watched the football game. "I'll meet you in the bedroom in a couple minutes."

I was just finishing with the enema bulb when Alan came down the hallway. He inspected me briefly and nodded. He was holding a buttplug in one hand - though not the same one as last week... it was definitely larger. He made a gesture and I turned away from him and bent over and seconds later I felt the buttplug pushing its way into me. Ow! It was definitely larger than the one I had last week.

Alan turned on his heel and headed to my old bedroom. I followed him down the hallway. The modified sawhorse I had been bent over last weekend was off to the side against the wall, so I guessed something different was going to happen to me this week. "Put these on," he said, handing me the leather wrist cuffs. I did, and then following his gesture, I put my hands behind my back. Something clicked as Alan hooked them together, securely locking my hands behind my back.

"On your knees," he commanded. I did so cautiously, being careful not to overbalance given I couldn't use my hands to steady myself. Alan walked behind me, and suddenly there was something over my face. After something was tugged over my ears, it took me a few seconds to work out that it was some sort of balaclava, with holes open over my eyes and mouth.

"Mouth open." When I complied, Alan jammed a ball gag into my maw, and he expertly and quickly tightened it behind my head. And then, without warning, a blindfold of some sort covered my eyes and was quickly tightened as well. The thick band went over my ears, too, muffling what I could hear. Suddenly I was rather cut off from everything. I think Alan simply walked right out of the room while I was adjusting to these new limitations, for I had no sense of him leaving. I was just... alone, in the dark and quietness. Waiting once again.

After one of those stretches of bored/horny no-time, I heard someone enter the room - or, rather, I felt footsteps approach me. They seemed to wait for several minutes - despite myself, my cock rose to full hardness in anticipation. I don't know if that was seen as an invitation, but suddenly I felt the exciting shock of a hand touching my cock - and then stroking it in a slow, steady rhythm. This wasn't quite the edge and tease session I'd had a couple weeks back, but whoever was giving it was patient and it felt amazing. Soon I was moaning through the ball gag. As I got close to the edge, the handjob eased off a couple times to stretch things out, but then the strokes started speeding up, clearly aiming to take me over the edge...

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