Notes

Losing my anal virginity
I’d known he's gay for a long time and I'm totally cool with it. I wouldn't really consider myself straight exactly anyway, I think bi-curious is the right term for me. I say that because I've only every dated girls, but I do fantasize regularly about men and dicks and cum, and I've even acted on it once before. But I digress, the point is Rick has never made me feel uncomfortable in any way about it. He was just a really good friend, who I knew I could talk to and enjoyed hanging out with.

This particular night though turned into somewhat of a gay fest. Perhaps Rick couldn’t control himself for whatever reason, but he ended up making comments about the players throughout the game. We were drinking our Gin & tonics as was customary when we hung out, so maybe he was a little too tipsy to control himself. Or maybe he was just horny that night, who knows. But he talked about their butts non-stop and loved how he could see their biceps and how strong they looked. “I’d let him just destroy me” he’d say. For the most part I’d just laugh it off and continue with whatever conversation I was trying to have with him, but then he said something that caught my attention.

“Man, I bet that guy tastes good!” he pondered. I looked over at him, puzzled, and though I just couldn’t let that one go without saying something.

“How would you know that?” I asked.

“Huh? Well… I don’t know, I’m just assuming.” He replied.

“But how would you assume that?” I asked again. “I mean, doesn’t the taste come mainly from a man’s diet?”

“I guess so, yea” He answered. “But I don’t know, some people just look yummy. You can just tell.” He explained.

So we ended up talking about sex for a little while. Something that Rick and I almost never did. There had been a few times that we talked about it, but not often. He knew that I had tasted another man’s cum in the past. I had an experience in a gym locker room one time. I had told him all about it when it happened because I wasn’t sure what it meant and he was gay, but also because he was my best friend and at the time it was almost like a crisis in my life. But he helped me through that, and we never really brought it up again. But as we started to talk about cocks and cum and tight butts, he asked me about my experience again. I was surprised how open I was talking about it with him, but it really was just a casual conversation.

Anyway, the game went on and we had moved on to other topics and by the time 11 pm rolled around we were both pretty drunk. It wasn’t like the old days where we could just go all night. I was tired and he clearly looked it too. But he had had way too much to drive home so I told him he had to stay. I pulled some blankets out of the linen closet and we prepared the couch for him to sleep on. I told him I’d be sleeping in for sure in the morning so he wouldn’t expect me to get up and see him out if he was awake before me. I said goodnight and went to the washroom to wash up.

While I stood in the washroom, taking a leak I glanced in the mirror to my right. I watched the stream coming out of my penis and began to think on the conversation we’d had earlier in the night. I had always had a fascination with penis and when the urine stopped flowing I couldn’t help but stand and stare at mine. I threw my pants down to my ankles and slowly started kneading my cock. Still thinking about the conversation, in my drunken state, I couldn’t resist the urge to masturbate… gay style. I opened the drawer under the sink and reached to the back where I had a small buttplug hidden. I took out the small bottle of lube beside it and applied some to the tip. I sat down on the side of the tub, as I always do when I jerk off this way, and spread my legs wide putting one foot on the sink counter and the other foot on the inside tub wall. My cock was already hard and I lifted my balls out of the way to gain access to my asshole. I leaned back a bit and touched the tip of the plug to my ass. The cold lube shocked me at first and then warmed quickly. I slowly but firmly pushed upwards and the plug started to slide in. As it reached its thickest point near the bottom I let out a little groan of pain. Then it popped in and I felt it hit my prostate. Ohh what an amazing feeling. I let it linger there for a moment while I started jerking my dick. As the pleasure got more intense I sat forward on the tub and put my feet down, which put pressure on the plug. I started writhing my hips forward and backwards as if I was riding a bull. The plug was moving inside me and rubbing my prostate again and again. I was getting close to orgasm, so I leaned back again and threw my legs open, with my feet where they were before. I pushed the plug out of my ass and started lightly pumping it in and out with my left hand. Every time it popped in I could feel it hit my prostate, and I’d yank it out to do it again stretching my asshole each time.

Suddenly, the bathroom door opened.

I reacted instantly by closing my legs and turning my body away from the door, as I looked up in terror. “Oh my god!!” Rick yelled as he quickly shut the door. A brief pause. “I’m so sorry man.” I heard him say quietly through the door.

I was mortified. I knew the lock on the door didn’t work, but I guess I just hadn’t thought about it. I was too worked up with what I was doing. I sat in shock for a while as my penis softened and my butthole puckered tight. What could I do? Should I go talk to him about it? Would that make it worse? I heard Rick’s footsteps down the hallway so I knew he’d gone. I cleaned myself up, brushed my teeth and just went to my bedroom. I didn’t want to talk about it.

But a few minutes later he knocked on my door. By this time I had just my underwear and t-shirt on. Still less embarrassing than how he’d just seen me, so I told him to come in. he sat down on my bed beside me and immediately apologized. “I’m so sorry man. I thought you’d gone to bed already, I had no idea you were in there, but I should have knocked.” He explained. I looked down at the floor, my face red with embarrassment. “But look dude, you know I would never say a word to anyone. You know that!” He continued. “We all jerk off man. How you do it is your own business. And you shouldn’t even be embarrassed really. I’m your best friend. It’ll never ever leave this house, I promise.” As he reassured me, he put his hand on my shoulder.

I looked up from the floor and smiled at him. “I know that man. Everyone does it… but it doesn’t make it any less embarrassing being walked in on.” I replied.

“Well I suppose that’s true. I am really really sorry.” He repeated.

“It’s okay. Really… it’s not your fault. I knew the lock didn’t work. I should have been more careful.” I conceded.

I put my arm on his shoulder as well and we both laughed a little. A short silence and we knew everything was cool. He stood up and took a few steps towards the door. Then he spoke up again “So…” he started as he turned around to face me again “Do you always do it that way?” he asked coyly. He had clearly seen what I was doing, with the buttplug and all.

“No! No!” I answered quickly. “Definitely not all the time. I only do that when I’m… in the mood, I guess.”

“Ohh... cuz I had no idea you were into that.” He said. “How come you never told me you liked that?”

I didn’t really know how to answer him without offending him. But I suppose I couldn’t just not tell him. “I dunno.” I started “I guess we just don’t really talk about that stuff much. And uhh… I didn’t want you to like… get any ideas or anything.” I said with a chuckle.

He laughed too and replied “Oh please! Just cuz you like toys in your butt doesn’t mean I’m gunna try to fuck you.”

“I know I know.” I said.

Just then, I got a sudden urge. Something came over me and I started to feel my balls tighten and my dick swell. My heart started to speed up as I looked at him and pondered. Maybe he could fuck me. I know my secrets are safe with him, he just told me so. Maybe I could let him fuck my ass. But does he want to? I knew I could handle it. I knew he had a big cock but with all the toys and experience I have, I knew I was ready. I had already blown a man in the past so I wasn’t new to that, I just hadn’t had cock in my ass. It almost started to seem to be the logic next step if I wanted to test my gay fantasies.

My heart really started racing and I looked at him as seriously as I could and just said it. “Maybe you could though.”


He stared back at me. I saw his eyes widen. “What?!” he exclaimed.

“I mean, if you want to, of course.” I said. “We’re best friends, so if you don’t want me that way I obviously understa…” he cut me off.

“Yes!” He blurted “I mean, yeah… if that’s what you want. I’ve dreamt about it for a long time.” He explained.

I smiled at him and reached out with my hand. He took a step closer and I grabbed his pants by the belt. I wasn’t about to waste any time. I undid his belt and unzipped his pants. I looked up to see him staring down in amazement. I slid his pants down to his ankles and held one leg of them to the floor while he stepped out, then the other. His boxer/briefs were tight and revealed his large bulge. I knew he had a big one because I’d seen him many times in change rooms and also group skinny-dipping in the lake at the cottage as well as the hot tub at his place. I had never seen it hard though so I could never be sure just how big it was.

I decided to tease him a little and raised his shirt up instead of going for the underwear. He helped it the rest of the way off and tossed it on the floor. Then I wrapped my fingers inside the top of his underwear and just rant them around the band while I looked up at him. He was still staring at me intently. I took one hand and lightly touched his bulge through his underwear. Then more firmly, I rubbed it up and down. As I felt it start to move I slid my hands around to his butt and squeezed on both cheeks. I pulled him towards me and bit down on his member through the fabric. Then I slipped the underwear down off his round ass and moved my hands around to the front. His underwear pushed on his thickening cock as I slid it down as slow as I could. As his meat was being unveiled my cock began to stir in my underwear. When his jockeys reached the tip of his dick it popped up and almost hit my chin because I was so close. I instantly took his knob in my mouth and sucked it in to the back of my tongue. My hands threw his underwear to the floor as I re-positioned myself to gain more access to his cock. I tilted my chest forward and my head back as I looked up in his eye and gulped in more of his meat. He had his mouth open with surprise and amazement at the sight of his best friend gobbling his dick.

I sucked back on his dick and slowly released it from my mouth. It was getting much harder now. I put one hand in his balls and began to roll and tug them. I put my other hand on his shaft and started slow pumping it while I put the tip back in my mouth. “Mmmm” I hummed as went down on it. I slid it back out and stood it up to admire it. His manhood was about 7 inches, and nice and thick. Larger than mine, but not too big that I would be scared of it, since I knew where it was going on this night. “Yum” I said softly as I looked at it, then bent it back down towards me and pulled his balls to my chin going as deep as I could. He was rock solid now, and so was I.

I slurped and sucked and twisted and rubbed for a while, moaning and grinning the whole time. Still silent, he reached down and pulled up lightly on my chin. I looked up and he moved back with his pelvis pulling his dick out of my mouth. He put his hands on the sides of my shoulders and encouraged me up off the bed. He lifted my shirt over my head and grabbed my underwear band. My cock was bulging inside so he pulled out on the band while pulling down, careful not to bend my cock. Without even touching myself there was pre-cum sitting on the tip of my dick. He leaned down and quickly licked it off. Then he pushed me down on bed and I instinctively laid down on my back. He got down on his knees and pulled my cock straight up in the air. He completely devoured my 6 inches in one swift motion. I was blown away. He stroked my balls with his hand as he held my cock up and continued to bob on it. Rick was certainly a master cocksucker, and it didn’t take long for me to start feeling my orgasm. I forced him to stop before it got too far and I calmly said “Not yet.”

He leaned back on his feet and I stood in front of him, turning around to face the bed. I crawled onto the bed and turned my head to look at him. On my hands and knees, I nodded for him to come closer. He reached out and grabbed my ass with his hands. “I’ve always loved your ass” he said.

I couldn’t help but reply. “Well you’re really gonna love it in a sec.” I chuckled

He giggled and continued to rub my buttcheeks. I reached over to the nightstand and took out a metal box and placed it on the bed beside me. He opened it and discovered another butt plug, 4 condoms and some lube. Without any words, he immediately opened a condom and unrolled it down his shaft. Then he squeezed a bit of lube onto my ass, which surprised me. For some reason I thought he would put it on his dicktip, but he put it on my hole instead. He put everything away, as I was looking back at him with approval. He positioned himself and started to rub his cock against my asshole. Sliding it up the entire length. I guess that’s why he lubed the hole instead of his cock. It felt nice, and I started to rub my own cock with one hand.

I heard him lightly murmur “Ya ready?” and I nodded yes.

I put my head down on the bed and closed my eyes. He placed the tip of his dick on my entrance and started to push ever so slightly. He was thick, but I had a thicker toy, so I was ready. I felt the head pop in, it felt good. He kept pushing and it inched in. slowly but surely he entered my ass with no problems. Some slight pains every few seconds, but that added to the pleasure. It felt amazing. I didn’t even realize when he was all the way in, but I heard a loud moan from him and turned to look. I couldn’t twist enough to see my ass, but I could see his smiling face. “It’s in” he said simply.

“What? All the way?” I asked.

“The whole thing” he confirmed with a whimper of delight.

I put my head back down on the bed again and pulled my balls up to look. https://pornforvip.top/ I could see his balls hanging behind mine and that’s it, I couldn’t see anything else. He lingered for a few seconds and then slowly withdrew. I could see his glorious cock starting to appear as he pulled out. I watched as he began to slowly push it back in again. As it grazed past my prostate I closed my eyes and put both my shoulders down on the bed. Just my ass sticking up in the air, I whispered “Ohh fuck yes.”

He was sliding in and out of me easily now, his throbbing cock pleasing my insides. He braced me with his hands on my hips as his pace started to quicken. “Ohh yes” I blurted. He glided his hard dick in and out of loosening ass. “Harder!” I yelled. His pace picked up more and I could feel the fiery friction in my asshole. “Fuck me Rick!! Fuck me hard!” I screamed. He repositioned his hands, one on my shoulder and the other on the small of my back. He pounded me furiously and it started to burn. He pushed down on my back and yanked on my shoulder as he thrust his big cock over and over in my ass. It really hurt now, but the pain felt amazing. “Yes! Just like that. Destroy my ass!” I cried as I buried my face in the bed and clenched the sheets with my hands. Plunge after plunge his thick cock penetrated me and my dick rubbed on the bed with every thrust. I loved every second of it. Then suddenly he stopped.

I didn’t think he had ejaculated. Surely there would have been some sign of that, moaning, grunting, panting. He was in me to the hilt and just remained there for a minute. I raised my head and looked back at him. He pulled his cock out of my ass and I squeezed it tight. He pushed on me sideways encouraging me to roll, so I did. I looked down at his throbbing cock and saw how red and swollen it was, but no cum in the condom. I realized he had just wanted me to flip over so I got comfortable on my back and he spread my legs nice and wide. My cock and balls were presented to him and he positioned himself on his knees below me. He bent his hard dick downwards and put the tip against my ass again. He put both his hands on my knees and moved them up towards my hips.

Then he pushed in again. I felt his cock slide in and hit my prostate. My body reacted by spreading my legs further. Then he pushed my legs up further so that butt came off the bed slightly. He shoved in again and I felt pressure on my prostate again. “AHH!” I exclaimed. My eyes were shut. He pulled his cock out to the tip and lunged again. It was unbelievable, the feeling inside my body. He continued with long strokes. In and out, every time hitting my prostate and sending shivers through my body. My eyes shot open and I stared at him as he started pounding my ass yet again. Faster and faster, with shorter strokes, he stabbed my prostate. I couldn’t help but grab my cock and start beating it. He let go of my left knee and moved my hand away from my dick. He wrapped his hand around it and stroked it for me. I put my hands under my legs and pulled towards me, holding the position so nothing would change. This moment was heaven, getting the ass pounding of a lifetime and my cock jerked at the same time. I couldn’t hold on much longer. Rick stared at my cock as he was beating it and hammering away on my hole with his monster. He knew I was seconds away from exploding and pushed as hard as he could. With his thick hard cock pulsating against my prostate, he held it there and jerked my dick furiously. I looked down at my cock and my whole body tensed. My abs started hurting as my hips bucked forwards. Rick tried his best to move with me and keep his solid cock against my prostate. I felt my ass pucker and squeeze as my cock began to throb uncontrollably. And finally, I felt the release. The first shot hit my chest and then the second shot up to my chin, a tiny bit of my semen touching my lip. My mouth was wide open as my body convulsed and spurt after spurt emptied onto my stomach. Rick was still pulsing into my ass as much as he could until he couldn’t take anymore. My ass contractions must have sent him over the edge, because he quickly pulled out and ripped off the condom. He started beating his meat, but I grabbed it from him instead. As I stroked him he leaned forward a bit, his cock directly over mine. As I continued pumping his cock, his balls rubbed against mine. Then suddenly his dick stiffened harder than it already was and I felt it throb in my hand. I quickly grabbed his balls with my other hand and pulled on them, pumping faster. He erupted with a big grunt, and his spurt of cum landed on my face and the bed above my head, surprising me. I moved my head slightly to avoid another shot hitting me in the eye. Another blast got as far as my nose, and I tasted my first drops of Ricks delicious juice. And as his orgasm continued, the rest he unloaded on my chest and stomach, squirt after squirt. I aimed his penis down towards my own as the last of his cum oozed out onto my softening cock and my balls.

Panting in relief, he gazed at me in amazement as I licked his cum from my mouth and started mixing and rubbing our cum together all over my body. Then he leaned down to my penis and licked his cum off it. Not missing a drop, he cleaned my cock entirely and sucked each of my balls in his mouth, working the cum off with his tongue. Then he started working on the rest of it. I was surprised how much of an appetite he had for it, but it kept me turned on. He slurped and licked all our mixed semen off my chest, sucking at my nipples. He licked up my neck and chin, and then hovered his face above mine. He leaned in and met my lips with his. But I didn’t even realize that he hadn’t swallowed all the cum. He was holding it his mouth and as he kissed me our mouths opened and I felt the cum flow into my mouth. My eyes opened with surprise, but I eased into it the kiss and gladly took it. As we separated, I happily drank down our cum and he smiled watching me swallow.

My chest was a bit sticky, but he had done a great job cleaning me up. We both looked above my head at the line of cum on the bed and laughed. “You know… my ass kinda hurts.” I said, realizing just how raw it felt at that moment. His face went a bit red and he chirped back “Hey, you told me to fuck you!”

“I know” I said. “Don’t worry, I’m not blaming you. I just hope it feels a little better in the morning so I can do this again.” I explained with a grin on my face.

“Ohhh, I see.” He said. “Well, if it doesn’t, just let me know and we can trade places.” He said with a wink.

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