First Time Condom Break

[cgreg2033]

I had been in college for a couple years, staying pretty much to myself. I jerked off a lot and was pretty down low and not out. But I had been chatting with this high school senior in the same town for months, we would just talk dirty to each other mainly, sexting and sending naked pics back and forth, never showing our faces and never exchanging names. He admitted that he jerked off a lot with things in his ass because he came harder with something stimulating his insides. Obviously I repeatedly offered my cock but he didn't want to meet up or have sex with another guy. I found it extremely hot that he was hesitant and also a virgin to a real dick. 

On the night of my college's homecoming, I did the typical things college guys did for Homecoming. I went over to a buddy, Ray's house with friends before the game and got a little drunk. We went to the game and that sobered me up, so we decided to leave early to start the party back up at the house. After homecoming, the party started to get really fun. There were tons of people there. I guess word got out in town because in a matter of an hour, the house was packed and the huge backyard was completely full of drunk people. I had been drinking beer most of the night and it was time to break the seal so I headed to the bathroom, once inside, I sat down to take a leak so that I could check my phone and of course had some messages from the high school guy I'd been sexting for most of the year. 

There were the usual messages, he had sent me a pic of a smaller red bull can in his hole. It was so hot seeing his hole stretched out around the can. It looked tight as hell too. It was a good thing I was done pissing because I got an immediate erection. So of course I took the time in the bathroom to snap a pic of my hard cock to send to him. I mentioned that I was at a party and couldn't wait to get home to jerk off to his pics. I calmed my cock down a bit, washed my hands and headed back out to the party.

I met a lot of new people including my buddy Ray's lil brother, Mark. I should say that I "re-met" his lil' brother, I didn't recognize him, it'd been two years since I first met him and he grew the fuck up. He was hot as hell. He was shorter than my 6'2" frame, I'd say he was about 5'7", but he had a wide muscular chest, a little waist and from what I could tell a pretty good bulge in his shorts. Not to mention his ass was crazy bubblicious. Being slightly buzzed I couldn't help but kind of flirt with him for a bit. But I couldn't be too obvious about it of course. We kept running into each other throughout the night, and I could tell he was getting a little tipsy. Not much, but enough that he was becoming friendlier and bolder. He always had this goofy big smile when I ran into him. I went to the garage to get another bag of ice out of the freezer for the keg. When I opened the freezer I heard Mark come in the garage too. I just said,"had to get another bag of ice for the keg man, can you get one too so I don't have to make two trips?"

"You probably need to put some ice down your shorts," he said in a smug tone.

Not to be outdone by his bravado I said,"a whole bag wouldn't be able to keep this thing down," as I grabbed my crotch and shook it. 

He looked at my bulge as I grabbed it, and kept looking at it, a little too long. I was beginning to wonder about him when he remarked,"nice shorts, they looked lighter blue in the pic," with the biggest cheesy grin on his face.

Holy shit. The realization hit me like a ton of bricks. HE is the high school guy I've been sexting!!! I guess I couldn't keep the shock off my face cause he was like,"it's our secret man, as long as you let me see it. I don't wanna do anything, I just want to see it hard in person." 

I had beer courage so I thought to myself,"fuck it, if he wants to see it, then I'll show it right now." It took me about five seconds to get rock hard and pull it out. He just stared at it for a minute with an amazed expression on his face. He popped back out the door, looked around, then came back in the garage and shut the door. He quickly walked over to me, his eyes never leaving my stiff boner. He was a couple feet away from me looking down at my throbbing cock. He finally looked up at me, and his face was so fucking hot I wanted to start making out with him right then, but figured that wouldn't go over well considering how he'd made it clear over the year during out sexting that he didn't actually want to do anything with a guy. He stared into my eyes, let out a big breath and said,"it's thicker than a red bull can." 

His breath smelled so good, like beer and mints. 

Mark looked back down at my cock and surprised me when he wrapped his hand around it,"damn that's so thick dude," he mentioned as he squeezed my rod. His hand couldn't wrap all the way around my dick and he kept squeezing it,"it's hard as a rock too," he gulped. 

I figured we had extended our luck as far as we could being at such a big party so I mentioned we better get the ice to the kegs or someone would come looking for us. He reluctantly let go of my cock and agreed to help me with the ice. As I got into the freezer and we loaded our shoulders with bags of ice my hardon eased down enough that it wasn't too obvious in my shorts. 

We got the ice around the kegs, and got back to partying. Eventually the party thinned out, and there were maybe 30 people left. A small group in the house, some people on the front porch and myself, Ray, Mark and a few others had built a little bonfire in the backyard and were sipping on some beers and just talking and laughing. Mark was getting a little drunk and thus bolder. He'd wink at me when no one was looking or look straight at my crotch, at one point he had a beer can in his hand and when no one was looking he put it in his mouth real quick. I was surprised he could get something that wide in his mouth, but it turned me on instantly. I got hard, but since I was sitting down, I could manage hiding it from everyone. Everyone except Mark, who would stare at it and laugh. He knew what he did, the little trouble maker, and found it really funny he put me in that situation, trying to hide my boner from everyone. 

Later that night everyone had gone home pretty much except the people who lived at the house, Mark and myself. I was cleaning things up, everyone had gone to bed, Mark was on the sectional in the living room watching a movie, so I finally joined him. I didn't sit directly next to him, just in case someone came into the living room. The only light in the room came from the tv. Mark got up and started taking his shoes off, he said he was gonna go get a pillow and a blanket. It seemed to take awhile, so I took my shoes off and positioned myself snugly in the long end of the sectional. 

When he came back I noticed he had changed into some mesh basketball shorts and a tank top that showed off his muscular body and I could see his nipples. Which...of course, made me hard again. He immediately noticed and joked,"man, you're hornier than a dog with two peters." He put his pillow right on my lap, jumped onto the sectional with his blanket and laid his head onto the pillow quipping,"maybe my head will keep that big thing down."

He was on his side with his head in my lap on the pillow watching the movie when he put his arm under the pillow to get more comfy and bumped my erection with his arm. He laughed and said,"really? still hard?" 

I chuckled,"well if you hadn't come in here half dressed showing off that body and putting your mouth so close to my nether regions then maybe I'd be limp by now."

He reached under the pillow and grabbed my cock through my shorts, looked up at me and smiled,"does this help?"

"It might help me cum if you're not careful," I replied.

"Would that be a bad thing," Mark responded. 

I whispered,"no."

He started stroking me through my shorts which felt amazing, I didn't do anything for fear of crossing a line with him that he might not want to cross. He said,"whip it out man, so I can feel it skin on skin."

I quickly unbuttoned my shorts and let my rod loose. Now he was turned on his side but this time toward my cock, not the tv. I could feel his breath on my shaft as he stroked it. I was so horny at this point that I decided to be a little bold and mentioned how impressed I was that he got a beer can in his mouth earlier and suggested he try getting my cock in there. He hesitated, and I held my breath hoping I hadn't ruined the moment, then he went down on me. I sucked in more air as I felt his mouth slowly go down on my entire shaft. It was warm, wet and felt fucking good as hell. This whole night of taboo flirtations and partying had me over excited and when he got my whole cock in his mouth and throat without even gagging I almost exploded right then. I grabbed the back of his head and warned him not to move or I'd cum. He stayed motionless as I calmed down and told him to keep going. He was taking my cock all the way down and into his tight throat and back out again. He began to speed up his bobbing, going quicker now. Again I had to grab the back of his head telling him I was about to shoot. This time he pushed my hand off his head and went double-time on my cock, I lasted about ten seconds longer when I started to pant and whispering,"oh shit, oh shit, oh shiiiiiitttttt," while I blew my load down his throat. I could see his neck muscles working on swallowing every drop of my load. He kept sucking me for a few minutes and finally pulled my dick out of his mouth. 

He smiled up at me saying,"I wasn't expecting to ever do anything like that with a guy, let alone like it. But that was hot when you came in my mouth, it felt so good having that thick hard meat exploding in me."

I was still hard as a missile, and told him how much I loved his mouth and the fact that he swallowed my cum. I said,"lay your back across my lap and I'll jerk you off." He happily obliged. He pulled off his tank top, scooted up on me and yanked his shorts down under the blanket. I started rubbing his sexy nipples then ran my hand down his abs, then v-line, and found my prize. He was about 6 inches, average thickness, but he had foreskin, which I find extremely hot. I began stroking him faster and he would occasionally moan and leak some precum out of his big mushroom head. He was breathing harder as I worked his cock in my hand, I wrapped my other arm under his back and around him and began pinching and rubbing his nipple. I could tell he was getting close, so I leaned down and sucked in his nipple. That set him off, My mouth was working his hard nipple while I furiously stroked his cock and his whole body started spasming as he blasted his cum all over himself and the blanket. Once he cooled off he asked if I would get him some paper towels to clean up. I slid out from under him and off the couch but I didn't go to the kitchen for the towels, instead I got on my knees in front of him, pulled the blanket off and started licking all of his cum off his stomach, groin, and cock. He was still hard, as was I, so I began sucking him vigorously. It only took a couple minutes before he had to put his arm across his mouth to muffle his moans as he shot another load, this time deep in my mouth to which I instantly swallowed. We were both exhausted by this time. He pulled his shorts up and covered back up while I went back to my earlier position on the sectional and laid down. We fell asleep pretty quickly. The next morning his brother Ray woke us up and asked if we wanted any coffee or breakfast. We quickly agreed to both as we sat up and came out of our sleepy haze. Mark and I were yelling at Ray in the kitchen as we all laughed and replayed some of the funnier moments of the party last night. Ray brought us a couple plates of food and coffee saying,"watch out, the coffee's still hot." 

Mark said,"good, my throat is pretty sore from last night," as he looked at me dead in the eyes. Thank god his brother wasn't paying any attention to him, he chuckled. Mark sure enjoyed messing with me. Which was perfectly fine, because I enjoyed "messing" with him. We had a lot more good times after that party. We no longer sexted each other, we actually became really good friends...who occasionally fucked around. He's married now, but we made many good memories while I was in college. 

[cgreg2033]

Part 2

After that night of the homecoming, Mark and I had become really good buds. I'd see him often at his brother Ray's house, which I regularly visited. Mark and I would sneak off here and there and have some fun giving each other bro-jobs. He started dating this really cute girl, who was a few inches shorter than he was and had a massive rack on her. Her tits were firm and perky, and he'd tell me how they fucked all the time and all the details. It turned me on every time he'd talk about it, and he knew it. He loved getting me hard without touching me, particularly when other people were around. He'd laugh to himself every time he knew he got me to bone up. 

One night, Mark, Ray, Ray's girlfriend, and I were all at Ray's house drinking and having a good time on that same sectional where Mark and I first experienced each other's mouths. Mark's girlfriend was out of town so we were getting a little drunk, and Ray pulled out a joint. I can't smoke the stuff, but I don't mind if other people enjoy it. I kept drinking, while everyone else got high. They didn't over-do it or anything, they all shared half a joint, and had a light buzz going on. Mark and I could tell Ray's girlfriend was enjoying the high as she began to get more frisky with Ray in front of us. She would playfully rub her tits against Ray and say she wanted him to cum on them. She grabbed Ray's cock through his shorts and he was blatantly erect. Mark and I just looked at each other and laughed. Finally Ray couldn't handle it any more and yelled at his girlfriend,"Alright! If you're so horny, we're going upstairs and I'm gonna fuck the shit out of you." She simply got up, took her shirt off and threw it at Ray and walked up the steps. 

Ray looked at Mark and I with big eyes and said,"well, I guess I'll see you boys in the morning then." We all laughed as he followed her up to the bedroom. 

Mark and I were watching tv and having some beers when we heard Ray's girlfriend moaning. Mark laughed and said,"you know who moans like that?"

Of course I knew he was talking about his girlfriend, I had heard enough stories by now and I knew what he was he trying to do to me. He was trying to get me hard, so I said,"yeah I know who moans like that, you do, when I stick this fat cock up your ass." 

His smile faded and I thought to myself I'd crossed a line, but he took a big swig of his beer and said in a very shaky voice,"we can find out."

Now MY smile was erased, and yup, you guessed it, I got hard as steel in seconds. He looked down at my crotch and laughed,"I knew that would do it." 

I quickly quipped,"Don't tease me, unless you're gonna please me."

He got up from the couch, walked over to where I was seated, leaned down and whispered in my ear,"I know where Ray's roomie keeps his condoms and lube, you're gonna fuck me tonight."

I didn't know if he was just high and trying to one-up me or what, so I played right along, and pulled my face back from his ear, grabbed his face with my hands and pushed my tongue into his mouth. If he was trying to shock me, I wasn't going to be outdone. He didn't resist, in fact, he sat down on my legs and started kissing me back. His mouth tasted like beer and weed, but gosh damn, I loved it. He was wearing basketball shorts and I could easily see he was hard as we made out for the first time. I began to run my hands up the back of his shirt against his skin, pulling him closer to me. I slide one hand down and grabbed his bubble butt, it was so muscular and firm, that I moaned into his mouth, he reached back, grabbed my hand and put it down the back of his shorts. While we kissed and tongued each other I slide my hand down his smooth crack and found his hole. I began to massage it firmly with two fingers. He was smooth, but also slightly...wet? 

I broke our kiss off and said,"you're wet, you've had something in your ass today when you jerked off just like you used to."

Mark replied,"remember the pic I sent you homecoming night of the little red bull can in my hole?"

Hell yes I remembered that picture. I jerked off to it all the time.

"Well tonight, I used the bigger can, so I could be ready for you," Mark said while he looked directly in my eyes. 

Okay. So Mark wasn't playing any games with me. He legit wanted me to fuck him tonight. And I was 1000% into it!

"Go get those condoms and lube now," I told him. 

He got up and went to the bedroom. He came out of the bedroom and was looking around like he'd lost something, then went to the kitchen and came back with olive oil and a condom, I looked at the olive oil and he just shrugged and said,"can't find the lube, we gotta make this work. Get naked and lay back, I'm gonna sit on it so you don't tear me a new one."

I shucked my clothes and laid back just like he asked as he pulled off his clothes, took the condom out and started rolling it onto my erection. I have a pretty thick cock, so the condom wasn't going down very well. Mark put some oil on my dick and the condom started to slide down it now. It was so tight it almost hurt, but I didn't care, I desperately wanted inside Mark's ass. I guess I always have wanted to be in his ass to be honest. He got on top of me, I started rubbing his legs on both sides of me as he oiled up my condom covered cock and began to sit on it. 

I knew he already had a big can up his ass earlier today, but fuck was he tight! He would sit down on it just a little bit then come off of it, then back down again, until a few inches were going in and out of his hole. Everything was going pretty well, he came off my cock again, and added more olive oil. This time when he sat down on my cock he  put about half of me inside his hole then we seemed to have hit a barrier. My dick was stuck halfway up his tight hole. I could tell he knew we had a problem too. I didn't want this to ruin the moment so I pulled his face toward mine and started to kiss him again. I told him how tight and good he felt, and how I've been wanting this for a long time. He began to relax and get into making out, he adjusted his position so he could kiss my neck, and that's when it happened, his hole gave in, and in one moment I was balls deep inside him. He grunted hard and gave a deep moan against my neck and said,"Fuuuuuuuuucckkkk dude."

We stayed like that for a bit, he was breathing into my neck and my cock was literally throbbing inside of him. He started to rock up and down on me now, fucking himself on my cock. He leaned up and sat all the way down on my cock again, this time when he bottomed out I guess my cock head found his prostate because precum poured out of his foreskin. 

Mark moaned again and the look of pleasure (and maybe some pain) was all over his face. He started riding me faster and breathing hard when all of a sudden I felt it...the condom snapped. I wasn't surprised that it happened because I'm very thick and it was extremely tight on me and Mark used oil as lube which I knew from sex ed degrades latex. What DID surprise me was the fact that Mark felt the condom break too and we froze, locking eyes. 

"You're all the way in me...bareback now. You're like REALLY inside me." Mark stated

I didn't know what to say, I just shook my head "yes" with this dumbfounded look on my face and my mouth hanging open. 

Mark breathed out,"god it feels so fuckin good, you're huge and you're entirely inside me...raw."

He started to ride me again, so I just went with it. I was grabbing his legs and rubbing his body all over, I'd pull him down and into a kiss every half a minute. His cock was still drooling precum when he sat on me fully. We were both getting into this, a lot, when he reached back and grabbed the base of my dick and started to slowly come up off of it. When my head pulled out of his hole it even made a "pop." He pulled what remained of the condom off my cock and said,"follow me."

I didn't hesitate, I immediately got up and followed him into the kitchen where he tossed the condom pieces into the trash then bent over the kitchen table. I came up behind him and looked down at his big muscular ass, saw his tight wet hole and pushed the whole thing up his ass. He let out a big breath,"yesss, fuck my hole."

"You want this dick, Mark?" I retorted as I began pounding his ass. My thighs were slapping against his firm ass cheeks as I plowed into him faster and faster. I couldn't handle seeing my cock pistoning in and out of his hole much longer. It felt incredible and I was getting close. I struggled to get the words out,"I'm gonna fucking blow man."

Mark was jerking his cock feverishly under the table and moaned out,"fucking don't pull out, just let me finish, cum in me if you have to, but don't stop fucking me!"

That was it. That did it. I started blowing a huge load up his ass, and did just as he said, I. KEPT. FUCKING. HIM. 

As I shot my load up his ass and kept fucking him as fast as I could his whole body tensed up and he was breathing out,"oh god I can feel your cum. fuck. oh shit. oh god. ohhhhhhhhhh!" as he blew his load onto the kitchen floor. 

I was still fucking him, and to my surprise when I heard him say those words and he started blowing his own load, I began blowing ANOTHER load up his ass,"Mark, I, I, I'm cumming again, oh fuck dude, I'm cumming in you again, ahhhhhhhhhhh." 

We were both covered in sweat and coming off our orgasm high. We were trying to catch our breath as I slowly pulled out of his ass. He stood up and we just looked at each other like, well, like we just had the best fuck of our lives. Oddly enough, that's when we heard what could only be Ray's girlfriend, having a very loud orgasm upstairs. That snapped us out of our blissful fuck haze and we realized that we were naked in the kitchen, with our clothes in the living room, our bodies covered in sweat with his cum on the floor and my cum leaking down his leg. 

Mark and I gave each other "oh shit" looks of panic and started cleaning up our mess. We went into the living room and grabbed our clothes, I said,"go to the bathroom and try to push out my cum and get dressed, I'll put something on tv."

Mark had just walked out of the bathroom before we heard Ray coming down the stairs.  Mark sat down on the sectional on the other side across from me and Ray just laughed and said,"damn, I fucked her so good it smells like sex down here too."

Mark and I laughed too.

Ray grabbed us all beers and sat in between us on the sectional and started watching the football game. Mark had pulled up his legs onto the couch while he drank his beer, I looked over at him, and he winked at me, slide his hand down to his shorts and pulled them up enough for me to see his wet hole with my cum still around it. He just did it for a second, but it got me hard anyway, and he just chuckled into his beer can as I grabbed a pillow to cover up my boner. 

[studl1]

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[Guest zyx11]

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