Popping My Anal Cherry

I've written about getting fucked before, but this is the very real story of my first time getting fucked. I had been chatting with Dennis for a few months. He was a good guy, really easy to chat with and very patient too, given the amount of time spent messaging back for forth all those months. Well, after the months of chatting, the opportunity arose for us to meet. My girlfriend at the time was out of town and I was online when I saw Dennis hop in the chat, so I sent him a pm.

We went back and forth with the small talk before it started to get hot, both of us saying how horny we were and how the direction of the chat wasn't helping. I finally told him my girlfriend was out of town, he asked if I wanted to meet. As horny as I was I couldn't type yes fast enough. He gave me his address, which turned out to be much closer to me than I had expected, about 5 minutes away from me. He asked me to show up around 7pm and to come in through the garage. I said I would see him then, then he logged off.

It was only 4, so I had a few hours. I stayed online to stay horny and to keep from getting in my own head about meeting Dennis. I always get so nervous about meeting, most times ending in me finding an excuse to not go ahead with it and feeling like an asshole for ditching out. I still got nervous, but I was determined to go through with meeting Dennis. Around 6 I hopped in the shower, got cleaned up and ready to leave. Even though I knew from previous chats he really wasn't into me wearing lingerie, for my sake I slipped on a pair of my girlfriend's pantyhose.

Pent up excitement and restlessness got the best of me and I left a little earlier than I should have. As I pulled closer to his house, the gps told me it was on my right, I saw the garage door open as he said it would be. I was about 15 minutes early, so I did a couple laps around the block, unsuccessfully trying to kill some time. So I just pulled up in front of his place and went in the garage and nervously knocked on the door. The door opened and there he stood, shirtless and in a pair of khaki shorts, and welcomed me in.

We made awkward small talk for a bit, we both knew what I was there for, so I just said let's skip this part. He agreed and led me to his basement, he had a bedroom set up down there. He let his shorts fall to the floor and I quickly stripped down to my pantyhose. He chuckled when he saw me in them and asked me to take them off too. I watched his soft 5 inch cock dangle between his legs as he stepped to me.

His hands went to my waist and he pulled me to him, our cocks touching, he leans in to kiss me. I had never kissed a guy before, but I went with it. His lips touched mine, my cock sprang to life, it was so HOT!! I felt his lips part, his tongued push between mine and they met, I melted and returned the favor. I was full on making out with another dude and it was incredible, tongues dancing, lips parting... heavy breathing and all.

Our hands were all over each other, exploring, feeling, kneading. Our kiss only breaking as we fell to his bed, where we quickly went back to making out, adding a new element of dry humping each other. Everything unfolded from there. He moved form my mouth to kissing his way down my neck and to my nipples, ending at my cock. As his lips wrapped around my hard dick, he shifted his body, moving into a sixty-nine, his cock hanging right above my mouth.

His cock was amazing, growing to just over 6 inches. I greedily sucked him all the way in, bobbing up and down, loving how every inch felt going in and out. His expert mouth was working wonders on me, I started bucking... I was going to cum. I tried to warn him, but I couldn't get my mouth off his cock fast enough. I'm sure he knew what was coming, because he doubled his efforts. Too far gone, I let loose with what had to be my biggest load ever. I must have spurted six or seven gobs of cum, he swallowed every drop.

Normally I don't like to cum until I am done with whoever it is I meet with. I always feel shame and guilt after I cum. I don't know if it was the heat of the moment or not, but none of that shame surfaced. Instead, with his mouth full of my seed he pulled his cock from my mouth and replaced it with his mouth, kissing me, sharing the remnants of my seed.

Once more breaking the kiss, he looked me in the eyes and asked if I had ever been rimmed. I said no, never. This being the furthest I had ever made it when meeting with a guy. He smiled and told me to roll over. He got behind me, pulled my ass up a bit, his hands parted my cheeks, giving him perfect access to my virgin hole. I squirmed as I felt his tongue meet my ring.

As I settled, he went to town, licking in and out, around, pushing his tongue inside me. I was moaning in ecstasy as his tongue worked it's magic, that's when I felt the first finger pushing in. I moaned out loud as it breached the ring. He continued his laving and tongue fucking, sneaking in another finger. This only increased my excitement, I was begging for more. I wanted to feel him fuck me. I begged him to fuck me.

He got up and reached over to the nightstand, pulling a bottle of lube from the drawer. He applied some to his finger, kissing me as he worked it into my asshole. As got used to feeling, more lube and more fingers joined the first, until three fingers pushed into me. There was some discomfort, but nothing overly painful. I started to push back to meet his fingers pushing in. He must have felt I was ready.

He stood and lubed up his cock, he got behind me and drizzled some on my hole. He lined his cockhead up with my asshole and pushed in. I yelped as he pushed past the ring. He asked if I was okay and held there, allowing me to get used to the feeling. He took his time, letting me adjust to his girth. The next few minutes passed as he slowly worked his way inside me, stopping to add lube as needed.

I moaned as he finally bottomed out in me. He asked if I was okay, I said yes. With that he started to piston in and out of me. I couldn't describe the feeling, all I could do was moan and squirm at the sensations I was feeling. It was uncomfortable and pleasurable at the same time. As he pushed in I started to push back, sweaty skin on skin smacking sounds fill the basement. A steady stream of "Oh Fuck's" came from me as the sensations intensified.

It felt so good I started to cum again. I bucked as my orgasm shuddered through me. My bucking only served to push Dennis over the edge, he started to hammer into me harder and faster. His thrusts getting sloppy with our quivering bodies, until he hammered home one last time, blasting my insides with his load. He collapsed on me, pushing us both to the bed as he finished humping me.

We laid there panting as his cock started to soften and slip from my gaped hole. There was an awkward silence after, an attempt to kiss again only made things more awkward. He got up from the bed and I followed suit. I started to dress as we made some small talk. I told him how great that felt and thanked him for an amazing time.

We parted ways with another deep kiss, this time less awkward and more passionate, and plans to get together again when the opportunity arose. It wasn't until the next year we got to meet again and it was just as hot and intense as that first time.