Losing my anal virginity by CumCrazedCanuck
My parents were away for the weekend, so I decided to have my best friend Rick over to watch a game. I knew he didn’t really like football much, but he did like to watch the players run around the field in their tight pants. See, Rick is gay. , 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.