My Best Friend Dennis And I: Do You Wanna Go Inside Me?

This story begins like all others: at a strip club.

But first, some context. I was living abroad half-way through my twenties and Dennis had settled down with a girlfriend. I got up to so many naughty things overseas that I could write an entire erotic novel about my experimental sex life…and it’s all true. Just like today’s story is true. Now for the record, I’d taken a dick up the ass before this story takes place, but not Dennis’ dick. A ladyboy. My first experience, and not my last either. It happened quite abruptly. We met up via an a social meeting app. She was beautiful, to be honest. We chatted a bit, and then soon we were making out and both of us had our clothes off. Her dick was beautiful. About 5 inches, uncircumcised. I immediately started sucking her off and then using her foreskin to jerk her off. She was moaning so loudly. Then suddenly she said, “Okay. I fuck you now!” and before I knew what was happening, she had a condom on, rubbed a little lube on my anus and shoved her cock inside me. I screamed, or rather, I moaned initially, because it was sore…until it wasn’t.

She didn’t take that long to cum…twenty thrusts, give or take, in and out. And she went all the way in each time until she cried from pleasure shooting her load inside of me (well in the condom).  And after the first two or three thrusts, I started feeling not just good, but amazing. She was hitting my G-spot every time, so naturally, I started jerking it. My dick was rock solid when she came.

She took the condom off and showed it to me. It was so full of white spunk that the sight of it immediately turned me on even more. So I took the condom and poured the cum all over my dick and told her to jerk me off. She did just that, dropping the wonderfully slimy semen all over my rock hard penis and stroking up and down with both hands. I noticed that she was hard again, so I reached for her cock and started jerking her off. Soon it was a hot, steamy session where we jerked each other off.

Eventually she told me to slow down, that she wanted to cum at the same time as me. I immediately put our dicks together and started jerking them together slowly, my first frot (or frottage session) with a ladyboy from Thailand. “Fast! Go Fast!” she instructed me, and I picked up the pace. I could feel my balls swelling up to an epic conclusion and I just let it out…I came all over her dick and mine, 7 ropes of cum at least, and less than five seconds later, she shot her second load, although you’d have thought it was her first, because she shot a massive load that hit me right in the eye. Afterwards I cleaned up and left, another memory for the wank bank.

That same year, I visited home, and of course, Dennis was the first person I hit up. It’d been a while since one of our “sessions” when we finally hung out again. We met for dinner, talked about our lives. One drink led to another. I had some weed, although he didn’t want any initially. However, we were both buzzed and, I’m sure, thinking the same thing. But the night was still young, and right opposite the restaurant we went to was a strip club. We looked at the sign, looked at each other, and it was a given that we were going in.

At that particular moment, I’d forgotten how boring strip clubs can be. Sure, there are beautiful naked women dancing and showing their goods and, depending on how far you wanted to go, you could book a room and have sex. But that was way too pricey, and I couldn’t justify the expense. Plus we were both good looking and with enough luck, we could have probably hit up a few nightclubs and gone home with equally horny chicks. Unlike the ladyboy in Thailand, which was an experience, this would be straightforward, emotionless, condom-on sex. The first thing I’d think about when shooting my load is my bank balance dropping. Like I said, it was expensive. So Dennis and I decided we’d stay for a lap dance, or two, or three, until we were so horny we had to leave or else waste even more money.

Now Dennis was house sitting at his brother’s place for the week. His brother was an architect and went to Europe a lot of the time. So the place was basically ours, and of course, I was going to spend the night there. Once we arrived it was around 11:30pm…so still way too early to go to sleep. Plus our hearts were still beating from all the beautiful pussies we’d seen. We cracked open two beers in the fridge, went to the lounge, put the tv on, not caring what was playing…although I think it was Anaconda. We started discussing everything from sex to…sex…to sex. We were horny, and I think both of us were just waiting for the other to bring up “the thing”.

Eventually I confessed that I’d been fucked in the ass by a ladyboy in Thailand. I told it to him just as I told it to you, and at around the part in the story where I talked about frotting (since we’d done it a while back) he started rubbing the tent he was pitching under his jeans. He had so many questions afterward, but mostly he wanted to know how it felt to have a dick inside me, fucking me, and cumming inside me. I reminded him that the chick was wearing a condom—“But still!” he said, “Fuck, I’d love to experience that.” Then he told me that he still watched gay porn from time to time, and his favorite videos were when a slim, feminine-looking guy gets fucked in the ass by a more manly-looking dude.

Now, between the two of us, Dennis could definitely pass as a twink, if he wanted to. And I was definitely the more manly-looking one, albeit both of us were slim and in good shape. I told him he should definitely try it out. He said he probably wouldn’t because he’d only do it with someone he trusted…we went quiet for a few seconds. I took a sip of beer. Then I suggested that we smoke the joint of weed I had on me. He was all up for it suddenly, and we stood outside for a bit, smoking it halfway, before I said, “So basically, you want me to fuck you?” to which he responded, “I dunno, do you wanna go inside me?” I considered the question and the answer was FUCK YES. Although I answered with, “Do you have lube?”—“I’m sure my brother does.”

We ventured into his brother’s room, rummaging through drawers. We didn’t find any lube, but we did find a jar of coconut oil, and I knew that that would be just perfect. “How should we do this?” he asked me. I told him not to move. I kneeled down on the ground and softly guided him to the bed so that he was sitting on the edge. A little bit of foreplay, I thought, would go a long way to making this an unforgettable experience. I unbuckled his jeans. He dropped them to the ground. I removed his boxer and, once again, after quite some time, I was staring at his beautiful, circumcised, pink six-inch penis. “God I missed your dick,” I told him. “Yeah?” he said, his heart racing, knowing what was about to happen. I opened my mouth and swallowed his cock, deep throating it immediately—“Oh my God. Fuck that’s amazing dude.” I kept going for a while, using my hand and my mouth, slobbering all over his cock, so much so that my spit was sliding down over his balls onto his anus.

And while this happened, my member was mentally preparing itself for what was to come. I stopped, stood up, and told him: “Turn around”. He didn’t need much explaining. He knew what I wanted him to do. He turned around so that his ass was facing me. I spread his buttcheeks. What I loved about Dennis is that he had hardly any hair. If he shaved completely, dressed up and put on makeup, he could pass for a very attractive woman.

“You sure you want this?” I asked him. “Fuck yes. I want you to fuck me.” I reached into the jar of coconut oil, dipped my hand inside, scooped out a decent amount and rubbed it all over his anus. Then I stuck one finger inside, just to loosen him up. “How’s that?”—“Good. Put another one in.” I put two fingers in and moved them in and out for a about a minute. "Mmmm. Yeah…that’s nice.” I stopped, then I readied my dick over his anus. “Okay, I’m gonna go slow.”—“Just do it like she did it!” he told me, and he pulled my hips towards him. Fuck it, I thought, and I shoved my cock inside him. “Arrgh!” he moaned. It wasn’t even all the way in. Maybe just two of my six inches. “Is it painful?”—“Keep going!” he said. So I thrusted into him again. 3 inches. Out and in again. 4 inches. Until I had five of my six inches inside him. I began moving slowly. “Yeah. Oh yeah, fuck that’s fucking amazing,” he said, asking me, “Do you like it?”…did I like it?

I fucking LOVED IT!

I’d never fucked anyone in the ass before. And this is how it felt…like my dick was surrounded by a warm, mushy molten substance that brought absolute pleasure. It was incredible! Every time I thrust into his asshole with my dick, he moaned a little, and that just sent my head spinning into a maelstrom of pleasure. And I knew he was feeling pleasure too, just as I had felt it when the ladyboy had her cock up my ass.

After fucking him in his ass for at least 2 minutes, I decided it was time to go all the way in, so I pushed the final inch inside – “ARGH! Yeah! Fuck! Yeah go deep into me!” – and it was so nice to be able to shout, since no one else was in the house. I went full throttle into his ass. It was getting quite creamy down there too, and you could hear the sound of my balls slapping hard against his ass.

Then I stopped—and I turned him around, onto his back, so that he was facing me. I lifted his legs up and I positioned my cock against his asshole, rubbing it against his gaping anus. I put it back in, and it went all the way. Now that I could see him and his dick, I was even more horny, and the sex got more intense. His cock was rock hard. I saw him squeeze his precum out—there was so much—and then use it to lubricate his cock.

He started jerking off while I fucked him raw. His eyes were closed. He was in heaven. And so was I. This was the best feeling in the world. The way his asshole sucked my dick. The way he jerked his hard penis – “Let me!” I told him, and I started jerking him off – “Oh fuck, I’m gonna cum soon!” he said – “Wait!” I told him, and I slowed down my jerking of his dick. I wanted to time it so that we came together, or close enough together. I picked up my pace. I let go of his dick and he started masturbating again. I could feel my balls swelling up with cum – “I’m almost there!” I told him – “Cum inside me,” he said. I asked him if he was sure – “Fuck yeah. Cum in my ass dude. I want it.” Just hearing that sent me over the edge. I was now fucking his asshole like a rabbit.

It felt amazing…I didn’t want it to end…but I wanted to cum at the same time. “I’m gonna cum!” I said – “Me too!” – “Yeah? You want me to cum in you?” – “Oh yeah, please cum in me. Cum in me dude. Cum in me.” He kept saying it…”Cum in me! Cum in me! Cum---AAAAAARRRRGGHHHHHHH!!!! FFFUUUUUCCKKKK!” He shot a HUGE LOAD of cum that hit me in the face, followed by six more ropes that hid my chest and landed on his stomach. The sight of his cum was all I needed – “Fuck I’m cumming! OOOOOHHHHHHH FUUUUCKKKKK YEEEEEAAAAHHHH!” and I pumped what was probably the biggest load I’ve ever shot deep into his ass. I came for at least 7 seconds, which is actually quite a long time. Normally orgasms last about 3-4 seconds, but this one was different. It felt like forever and a millisecond at the same time…just…wow.

I pulled my cock out of his ass and, just like in a porn video, I watched him push the cum out of his creampied asshole. It was so fucking hot, you have no idea. Or maybe you do, if you’re lucky like me to have had a best friend like Dennis. I laid down next to him and for a few moments we were speechless, like we were trying to figure out how to feel about it. But the moment we looked at each other, we burst out laughing…because that was so much fun!

And as if that wasn’t enough, after lying down and chatting for a few minutes about how awesome the experience was, both of us got hard again, so we sat up and decided it was a nice time for a good old frottage session. So we climbed on the bed, interlocked our legs around each other and put our dicks together. His 6-inch pink cock against my 6-inch brownish dick with a pink top. Frotting is great when the dicks are the same size. He went first because my arms were a bit tired from the sex. He jerked us so well using just his right hand. After a few minutes, I took over, spitting on my hand twice and massaging our dicks with my saliva. I squeezed out my precum and then his, and mixed it all up into a spit-cum cocktail and started jerking us off…we started talking about how hot it was, the sex we’d just had.

I then stopped for a moment, and he naturally took over. I saw my phone lying on the bed. I tapped the screen.. It was only 00:30 and it was a weekend. Neither of us had to be up early.

So then I asked him: Do you wanna go inside me?