My Brother and I Try Anal

I woke up on the couch to a pleasant surprise. I was staying with my older brother at his place for the weekend and we had some fun sucking each other's cocks the night bfore. My brother decided that he would wake me up with a good morning blowjob and I woke to him with my cock hardening in his mouth. This was definitely something new for me and I let him know it was a nice surprise and something new. Taking my cock out of his mouth, he asked if I was interested in trying something else new?

"That depends on what you want to do," I let him know.

"Would you be interested in trying anal sex?" he asked.

He told me how his girlfriend had a friend who had been with them on their trip to Mexico and that she and her boyfriend had convinced them to have a bit of group fun that nobody ever needed to know about. At first, the girls had been making out and he and the other guy were watching. Then the girls said they would do more if the guys did more. They convinced him and the other guy to give each other handjobs and while they did that, the girls stripped down and were fingering each other while making out and sucking on each other's tits. The guys took the next step and the other guy started sucking my brothers cock and in turn his girlfriend started licking the other girls pussy. He told me how the girls transitioned into a 69, eating each other's pussy at the same time.

He and the other guy laid on their side and did the same, sucking each other at the same time and the other guy had slid a finger into my brother's asshole while sucking him off and he had enjoyed it. They were both so into it and everyone was so turned on, that he didn't think twice when the other guy laid him on his back and lifted his legs into the air and he felt the head of his cock pressing against his asshole. He tried to relax and said it felt great to have something going into his ass and began to enjoy it more as he slid his cock in further and started to slide it in and out. His girlfriend came over and straddled his face so he could eat her pussy and the other girl positioned herself so she could lick her boyfriends nuts as he fucked my brother. The guy came not much later, filling my brother's ass with cum and then he came himself once the other guy wrapped his lips around his cock. He said they thanked them for helping fulfill some fantasies and hopefully they could do some more that trip.

Wow. I was in shock. I never thought of what we did as gay - yes, it was wrong but we were just two guys messing around and some having fun. This seemed like taking it to the next step and I asked him what he had in mind. He explained that he wanted something bigger than his little dildo in his ass and wanted to feel me inside him. I had some hesitations but agreed, so we headed up to his bed.

He sat on the edge of the bed and sucked on my cock to get me hard and a bit lubed up. The anticipation of doing something taboo in so many ways had me so excited. I was harder than I had ever been. He took my cock out of his mouth and laid back on his back and lifted his legs up by his knees with his asshole front and center for me. I moved forward and pressed the head of my cock against his tight hole and pushed slowly and firmly against his asshole. After a moment, my cockhead pushed through the initial tightness of his ass and slid slowly into him an inch or so, just past the head. I now know why the guys in the videos had such looks of pleasure on their faces - it was so tight and felt so amazing. My brother had a slight grimace on his face and asked me to keep going. Slowly I pushed my cock further into his ass, taking a break when he looked pained, so I would slide back a bit and then start pushing in again until eventually I was entirely inside him. I took a moment before I started to slide in and out - alternating between short quicker strokes and long strokes that brought the head of my cock to the edge of his asshole, but never pulling it out completely. As I fucked his ass, I reached down between us and started to stroke his cock.

He asked me to stop so we could reposition and change positions and he told me to lay back against the pillows and he then came over and squatted over my cock and I was able to watch as it slowly disappeared inside his ass and he proceeded to ride up and down on my cock with his big cock flopping in between us. Then with my cock still inside his ass, he put his knees down to the side and leaned forward and I could feel his cock rubbing against my stomach, creating a snail trail from the pre-cum. He leaned forward and started to kiss me, sliding his tongue into my mouth and I kissed him back with our tongues dancing in our mouths. As he leaned forward lie that, with his tongue in my mouth, I started to increase my pace and fucked his ass harder and faster - this was tuning me on so much - my cock in my brother's ass with his tongue in my mouth. I came so hard with no warning and shot my load into his ass. He pulled off my cock and rolled over saying how awesome that was and that he needed a minute before we did anything more.

After a moment, he said he was ready to continue. At which point in time he asked me if I would get him off. Without any hesitation, I leaned over in the bed and started stroking his cock to full hardness, marveling at how it felt as it grew and hardened in my hand - warm and hard, yet soft at the same time. His big mushroom head called for attention, so I spent some time thumbing the pre-cum around his cockhead before leaning over and swirling my tongue on his cockhead, tasting his pre-cum. Hearing him moan, I popped that cock into my mouth, going up and down his beautiful cock shaft. I turned slightly on the bed so that I was facing down to his cock while on my hands and knees so I could feel the curve of his shaft go more naturally into my louth and was able to take him deeper than normal. Up and down, I bobbed my head on his cock, feeling it slide in and out between my lips. Then I felt something - a hand between my legs fondling my hardening cock as my brother was playing with my cock that would have been in perfect view with my rear pointed towards the headboard and him.

The other thing pointed toward him and giving him an excellent view of, was my asshole. Using his other hand, he reached up and starting playing with my asshole - at first just brushing my hole with his thumb, which i didn't mind. Slowly he progressed to sliding a finger just inside my asshole and I wasn't sure what to think, but it actually felt pretty good. I didn't protest but actually started to push back against his finger and was enjoying it. I heard him ask if I wanted to try more than a finger and I nodded that I did. He had me lie on my back and lifted my knees up on my chest and positioned his head behind my ass and proceeded to tongue my asshole as he fingered it. I told him that wasn't what I had expected and he let me know he was just getting me ready for his cock. I asked him to be gentle as he was bigger than me and if it hurt too much he had to stop. After licking my ass and loosening things up with first a finger and then two, he said he thought I was ready and told me just to relax. I took a couple deep breaths and relaxed the best I could. As he positioned himself, I tensed up a bit and he said to relax so it doesnt hurt as much and that the initial pain was worth the pleasure after.

I felt the softness of his cockhead press against my sphincter and tried to relax as best as I could. He continued pushing but could not get his head past my asshole, so he started rubbing the head of his cock against my asshole and was able to get the head in with all the precum he had smeared on my hole. The pain was intense as the first part of his cock pierced me - I thought about calling it off but asked him to continue, hoping it would be worth it. As his cock slowly slid inside me, I experienced a mix of pain as I spread to accomodate his cock and pleasure as the head of his cock pushed inside me. He slowly worked his cock back and would pause to check in with me as he pushed deeper. I was in heaven as he slid inside me, with some pain to remind me what were doing. As he got further in, he started to slide back and forth a bit, gently moving his cock inwards and then sliding it back a bit and with one final steady push and a grunt from him, he was all the way inside me.

The pleasure of his cock inside me and the grunt he made as he thrust the final length of his cock into me triggered an orgasm and I came all over my stomach with nobody touching my cock. As I came, I clenched and tensed and tightened up around his cock while also shooting waves of sensual pain through my body. As I settled down, he leaned forward and kissed me - slipping his tongue between my lips and kissing me deeply while he slid his cock in and out a bit, always going as deep as he could inside me. Then he pulled back from my face and watched his cock as he slid it almost all the way out, until I could feel his cockhead at my asshole and slid it all the way back in with a bit of force, sending waves of pleasure as I felt the head slide all the way back, the sides of his mushroom head brushing my insides. He repeated this a few times before following it up with a lot of rapid short thrusts, his balls slapping against my ass cheeks and my cock slapping aginst my stomach. I could see from his face that he was getting close, and he leaned forwarded and again, slipped his tongue in my mouth, kissing me forcefully as he raidly fucked my ass, and my now hard again cock rubbing against both of our stomachs. Then he arched his back, pulling his face from mine as he rammed his cock all the way in one last time as he unloaded jet after jet of hot cum inside me which triggered another orgasm from me as I once again came on my stomach. He pulled his softening cock from my ass and leaned down and proceeded to lick up the cum from my stomach and with it still in his mouth, proceeded to kiss me deeply again, sharing my own cum with me, before rolling over beside me with a big sigh.

"What a great start to the day," he said.

I cant wait to see what the rest of the day has in store for us.