First Time

Connor and I were chilling in the sauna and we got to talking. Lately he'd become my best friend, we were just hanging out all the time. I guess cause we were really the only people from our old high school crowd to come home from college that summer. Neither of us had a girlfriend so we started going out on the weekends in the city to try and get laid. Sometimes we got lucky but usually we just wound up hanging out with each other and it was totally fun.

It was late summer and it had gotten kinda cool that week; you could feel that fall was coming. But it didn't keep us from our normal routine of me coming over to his house in the late morning and chilling by the pool all day. We'd only fired up the sauna a couple of times over the summer - who needed heat in the heat? - but on that cool day it was perfect.  

Connor and I had developed this really honest and easy way of talking to each other. I've never had it with anybody else, not even with Katie, my ex-girlfriend. I could tell him basically anything and he wouldn't judge me, and I felt the same toward him. We went to different colleges and we were going to be heading back to them in like a week so I guess I was already starting to miss him. But for now we were making the most of things.

Connor got naked, I was in my little Speedo. That was another fun thing with Connor - we were super comfortable being kind of naked around each other. When his parents weren't around we'd skinny dip in the pool. At first it felt kinda weird but it was amazing how easily you got used to it. What was the big deal, anyway? We talked about how it was better to get an all-over tan and the more comfortable with it we got the more comfortable we were kind of looking at each other. Like, we both trimmed the hair on our bodies and our crotches. Connor had this stuff you could just smear on your balls and it dissolved all the hair so he showed me how to use it.

We got really into our bodies that summer, working out a bunch in his gym and swimming and tanning. We'd go shopping too and buy stuff that showed off our bodies. I guess I'd felt a little weird about that before but with Connor it was like, what's the big deal? We've got these hot bodies we might as well show them off. So we'd buy these little Speedos and tight shorts and stuff and sometimes wear those around the pool.

I guess I felt about as comfortable with Connor as I'd ever felt with anybody and I was aware of how much I was gonna miss him when we both went off to college soon. I was also kind of excited thinking about the freedom of it, because it sucked being back in the suburbs. I was gonna be back where there were tons of girls and tons of parties so we were talking about that.  

We talked about how much of a bummer it was that we barely got laid that summer. Looking as good as we did.  

"I want to fuck a virgin this year," Connor said. I laughed. "Seriously, dude. That's my one goal."

"I hear ya man," I said.

"Have you ever?" he said.

"No," I admitted. "I mean, not that I know of."

"Me neither," he said. He leaned back against the wood of the sauna. "I guess it's kind of cliche or whatever to want to fuck a virgin."

"I get it, dude, believe me," I said. "It's not even about it being tighter, or whatever, it's like...the idea of breaking some chick in..."

"Yeah!" he said, and looked right in my eyes. "It's, like, a psychological thing. Like you'll always be her first, you'll always be special or set apart."

We were smiling so big. We got like this sometimes when we agreed on something and we often agreed on a lot.  

"You pop her cherry and that's that, nobody can ever do that again," I said. "And it's not even like she has to be your girlfriend forever or you have to marry her or something. It's just that knowledge that you sort of, like, marked her."

"Dude," he said, and looked down at his dick. He was half hard. I laughed. We'd gotten hard around each other before, it wasn't a big deal. It happened. The funny thing was I was half-hard too and I grabbed it in my Speedo so he could see.  

"You know what would be amazing is if we could fuck a virgin together," he said, leaning back again and sort of letting his eyes wander. I saw his hand go to his cock. He wasn't stroking it, exactly, but he was kind of feeling on it and it was getting harder. This was interesting but not entirely weird.  

"Fuck yeah. But one of us would have to be the actual one to slide his dick in her first," I said. I stuck my hand under my swimsuit. Fuck it, I thought. I was so turned on from the sun and the heat of the sauna and this talk about virgins. I hadn't got laid in like two weeks. "Unless we stuck our dicks in her at the same time."

"Oh man," he said, shaking his head at the ceiling. Now he was definitely stroking himself. We both were. "That's an actual fantasy I've had."

"Two dicks, one pussy?" I said.

"Yeah," he said, chuckling. "Or one of us in her pussy and one of us in her ass."

"I would totally be down for that," I said.

"Seriously?" he said, and looked at me.  

"Yeah," I said. We looked at each other, jacking off, and we laughed.  

"Take that fucking swimsuit off," he said. I laughed and stood up to shuck them off. My cock was so hard. Goddamn we both looked so good with our all-over tans and muscles from a summer of nothing but swimming and working out. Plus our trimmed bushes. Connor's cock was a little different from mine now that I was seeing it hard. I guess it was a little bigger, thicker or something. I found myself wanting to touch it but I pushed the thought away and sat back next to him. As soon as I did though his leg went against mine. That was cool, it felt good. So we sat there jacking off and letting our thighs rub against each other.

"This is insane, but it's kind of fun," I said.

"Totally," he said. "We should find some chick to fuck together."

"Trade off between her pussy and her ass," I said. "Have you fucked a chick in the ass?"

"Yeah," he said. "Tracy, remember?"

"Oh yeah," I said, remembering.

"I guess she was a virgin to anal sex," he said. "That was pretty hot."

"Fuck yeah," I said. We were really getting into it now. The sweat was pouring off our smooth, muscled bodies and providing lots of lube for our cocks. "Dude look how fucking hard I am," I said and held out my cock for him to see. He looked over at it. His hand paused around his cock. His other hand reached over, slow but confident. He wrapped his hand around my cock. I didn't breathe. He stroked it once, from the bottom to the top.

"Is that cool?" he said. I looked over at him.  

"Fuck yeah it is," I said. I immediately reached for his cock. It felt so intense to have his cock in my hand and my cock in his. We shifted to get closer to each other and then we really started going for it. Jacking each other off. "You ever do anything like this?" I said.

"Just when I was like, ten," he said. I never had done anything like it but I'd always fantasized.  

"It's got me so close," I admitted. He slowed his hand.  

"Me too but I wanna make it last," he said. We were both getting extremely hot so decided to get out of the sauna and go up to his room. Nobody was home so we didn't even wait for our hard-ons to go down. We just got out and dove in the pool with our hard cocks jutting out. It wasn't a minute before we reached for each other's cocks underwater. We were jacking each other like that, braced against the side of the pool and our bodies kept getting closer.  

"Fuck this is insanely hot," I said.

"I know," he said.  

"We shoulda done this months ago," I said.

"We got all day," he said. He reached down to grab my balls. I grabbed his, rolling his smooth balls in my hand. They kind of floated in the water. His fingers kind of went underneath my balls and I wondered. I did the same for him. I had one hand stroking his cock and the other fondling his balls and taint and he was doing the same for me. In the water our bodies just kind of came together and our faces were right there. I looked into his eyes and kind of chuckled and he did the same and then we just went for it. Kissing each other. Just, like, a peck at first and then full-on making out. Tongues and everything.  

I had to knock his hand away from my dick. "I almost came," I said.

"This is beyond hot," he said.  

"I never thought I would do anything like this," I said.

"Me neither," he said. Our cocks were so hard in the water but we weren't stroking them. We had our hands on each other's arms and shoulders and we just started making out again and rubbing our cocks together. That was the hottest, maybe, when we started pulling our bodies real close so that I could feel his muscles against mine, our cocks pressed so tight. My hand went to his smooth ass and his went to mine and it was so intense I almost came from that. I had to keep breaking off from him. A bird rustled in the bush and flew into the sky with a squawk and it kind of startled both of us.

"Let's go upstairs," he said.  

I followed him up his carpeted staircase. He lives in this huge amazing house cause his dad is this famous lawyer. We went into his bedroom and shut the door. At first he closed the curtains but it was too dark so we kept them cracked a little so we could see each other. He lit a couple candles. It was all air-conditioned which felt amazing after the head of the sauna.  

We got on his bed and just started making out again. He was kind of on top of me and we were jacking each other off and kissing and sometimes just pressing our bodies close and humping against each other. He was feeling my balls and his fingers went underneath them and then he just went ahead and touched my asshole.

"Fuck," I said. He pressed his fingers harder against it. I was looking right in his eyes. I reached under him and pressed my finger to his asshole, too.

"Goddamn," he said. We kissed and felt each other's assholes. We weren't fingering each other, just kind of pressing in, feeling how it would feel. "That is so intense," he said.

"Yeah," I said. We would stroke each other then reach back and press against each other's assholes. We were getting so turned on. I was ridiculously hard. He was the one to finally say it.

"I kinda want you to fuck me," he said.  

"Yeah?"

"I mean, we don't have to. That's kind of intense," he said.

"Yeah," I said.  

"Get your finger wet," he said. I did. I pressed it to his smooth hole. He pushed back against it and it went inside. Goddamn he was tight. A virgin, I thought. "Holy shit," he said. He got his finger wet. Slid it into me. At first it was intense and weird. Then it felt amazing.  

"I'll fuck you but only if you fuck me too," I said.

"Oh hell yeah," he said and we kissed so intensely and we were fingering each other and jacking each other and all the sudden he started cumming all over me and it set me off. I felt his asshole clenching around my finger and I just let go and started cumming all over myself. We were making out and moaning with our cocks spurting all over each other and our fingers in each other's assholes. Then he collapsed onto me and our bodies were just smattered with sperm.

"Guess we didn't last," I said.

"Like I said, we got all day," he said. So we took a shower together. It wasn't ten minutes after we'd cum and we were both hard again. We made out in the shower. I soaped up his asshole and he soaped up mine. We fingered each other some more in the shower and I almost came again but I was determined to make it last this time.  

He turned on some music, chill beats, real low and soft. We started talking again.  

"Did you ever fantasize about doing this?" he said.

"I mean, I've thought about it. Wondered what it would be like. But I never imagined doing it with you."

"I know. But it feels exactly right," he said.

"I guess we're gonna take each other's virginity," I said. A light went on his eyes.  

"Holy fuck you're right," he said. We talked about what it might be like and agreed that if it was too weird we could just stop, neither of us had to go entirely through with it if we didn't want to.  

"Should we use condoms?" I said. He said he didn't actually have any but he did have lube. And I trusted him, it wasn't a big deal. But it sort of was cause I'd never even fucked a girl raw, I'd always used rubbers.  

He went first. He had me lay on my back and he lubed up my cock and his ass. Then he straddled me and pointed my cock to his asshole and sank down on it. It took a bit; I could tell it was hurting him. But he just kept breathing and he'd lift off of it and breathe and then try taking it again. A couple times he had to lift off it completely. But man, that feeling of his asshole gripping my bare cock was so unbelievable. And when he finally took it all the way; goddamn. He was sat down fully on my lap with my cock buried in him and he looked me right in the eyes.

"Fuck that feels amazing," he said.

"So good," I said. I felt his asshole pulse around my cock. I pulsed back, making my cock swell in him. He moaned. I couldn't believe I was inside him, that he was going to be inside me. It felt so perfect, like we'd been building up to this all summer. I didn't know how I was going to hold off from cumming inside him but we kept it real chill at first. Just sitting like that, feeling each other. He lifted off my cock a little bit and I felt his asshole grip the base and travel upward. Damn that made me moan. Then he started getting more into it, raising up until my cock was almost all the way out of him and sliding back down.

"Oh my god," I said.

"Fuck me," he said.

"Fuck," I said and held on to his hips and started pumping it into him. We were looking right into each other's eyes.  

"Fuck me," he kept saying.

"Yeah dude, I'm fucking you. Goddamn your ass feels good."

"Fuck my ass," he said.  

"Virgin ass," I said.

"Oh fuck yeah. Pop my cherry, dude," he said. About two minutes of that and I had to chill. It was just too good.

I wanted to try it so we switched. He got on his back and I lubed us up and straddled him. I'd honestly never had anything up my ass before other than a finger or two so I had no idea if I could do this. Especially since his cock was so thick. But I wanted to; I was determined. I kind of kissed the tip of it with my hole and when I finally slid down and took it - man, it really hurt. Worse than I thought it would. And I started to lose my resolve.

But Connor was totally cool, so I kept trying. The next time I tried it it wasn't as bad. The deeper I would take it the more it would hurt. Connor told me to breathe cause that would help me to relax, so I focused on that and before I knew he was in me all the way.

"Fuck yeah," he said, smiling and rubbing his hand up my chest. I held his hand against me, pulsing my ass around his cock. He pulsed back. That was the most intense feeling, of him alive inside me. I thought, I could get used to this.  

For a while I just sat there getting used to it. My cock was so hard. I stroked it a little but I was so close so I kind of ignored it and even that was hot, sitting there with my best friend's cock in my ass and my own cock rock-hard and sticking out from my body. Finally I started to slide it in and out of me and then it was like my body took over. I knew what Connor had felt - I wanted to get fucked.

"Fuck me, dude," I started saying over and over. Connor held on to my hips like I'd held on to his. I kept steady and he fucked his cock up into me. It was so amazing, I felt so out of control or something. It was building in my cock and he kept fucking me and I was like "Fuck me! Fuck me!", getting louder and louder and then my cock was pulsing and cum just started dribbling out of it.  

I was like "Holy shit!" I was gasping for air. Connor was like "Fuck dude!" It was the most intense thing. But it wasn't like I came, it was like a pre-orgasm or something.  

"Did you cum?" he said.

"No. Well, sort of." I was still so hard. Connor reached into the puddle of jizz I'd just shot onto his stomach. He tasted it. "What's it like?" I said.  

"Hot," he said. He pulled my head toward his and kissed me. Took some more of my cum and then made out with me with my cum in his mouth. That was fucking hot. We kept doing it until all the cum was gone and all the while his cock was still in my ass.

We switched off again. He got back on top of me and took it more easily this time. I honestly couldn't tell you which I liked more - him in me or me in him. It was a total toss-up. Plus just the fact that we were trying to draw it out and make it last as long as we could, like we didn't want it to end.  

We got into some other positions. I tried fucking him on his back. That was hot. I had his legs up in the air and I was just slowly pumping in and out of him. I liked looking down and seeing my bare cock plunging in and out of his pink asshole. It was like perfect sex.

He fucked me doggystyle. That really made him want to cum. I know I've got a pretty nice ass. I could just imagine it bent over and spread out for him. Then we switched. He's got this kind of skinny but muscular butt and it was so hot to see his asshole all gaping and ready for my cock and just sliding right in him. I reached a hand under his torso and pressed his back against my chest as I fucked him and we made out like that. I reached down and felt his cock and he was so ready to pop from getting fucked he had to knock my hand away.

We must have fucked for over an hour. We heard his mom come home. She was like, "Connor are you up there?!"

He was like, "Yeah, Mom, I'm just hanging out with Tyler!" Meanwhile I was totally riding his cock like a bucking bronco.  

We talked about how we wanted to cum. I said I wanted him to cum in me; he said he wanted the same thing - to have me cum in him. We were laying side by side jacking each other off and making out. Our asses were all loose and kind of sore and just well-fucked. We'd taken each other's virginity for sure, used each other well.  

"I could cum like this though," he said. "So fucking close to you dude." We were holding each other with each other's cocks in our hands and our arms around each other.

"Broke each other in," I said.

"We'll always have that, dude. You in me and me in you."  

"Fuck I'm gonna cum," I said. Our hands were just going at each other and it was right.  

"Me too. Fuck!" he said, and started shooting. I did a moment later. We looked down in amazement - our cocks just emptying gallons of cum all over our tight, smooth bodies. The first shot of his load went up over his head; my first shot landed on his face. I leaned over and licked it off and made out with him as the rest of it coated us.

Afterward we broke apart, laughed. We took another shower. I knew I was gonna spend the night. We had like a week together I wanted to make it last as much as we could. And we got better at it each time, for sure, but there was something special about that first time. I guess that's why they say you never forget it.