First Time Surprise

My first time turned into more than I had bargained for.

  • Score 9.4 (72 votes)
  • 4298 Readers
  • 3774 Words
  • 16 Min Read

I’m a straight guy, basically normal. I’d been curious forever and often had fantasies and watched porn, but never came close to acting on it. My girlfriend left town for a week, and I made a Grindr account, just to see what was out there. As soon as I started exploring, my in-box exploded with messages and pictures. It was so overwhelming that I deleted the app. But the next day I tried again. I had the same volume of messages, but as I read through them, one seemed normal. I responded, and we started chatting. I told him my situation, and he told me about how he’d been in the same situation a few years prior. His name was Ryan. We wrote back and forth and sent some pics for a couple of days, and I finally agreed to go to his place. To give myself an out, I had him meet me in my car in the parking lot outside his apartment building. It was a cool April night. He found my car and got in the passenger seat.

We exchanged greetings. It was so weird. He was definitely interested, and all I could think was that this was a silly mistake. As a fantasy it seemed hot, but suddenly this was another man in my car, and I could smell his manliness, and I knew I wasn’t ready. He tried to make small talk, and I didn’t respond much. I felt bad for wasting his time. He finally asked, “What do you want to do?” I wanted to leave. I wanted to tell him to get out of my car. I eeked out a weak, “I think I should go.” But even before I finished saying the words, he reached over and grabbed my face and started turning it toward him and said, “Let me do this first.” And he started kissing me. I froze and didn’t react. My mouth stayed closed and didn’t move, but he was persistent. My mind raced. I waited for him to stop kissing me so that I could say I wasn’t into it and then leave. Then he reached his hand over and started touching my crotch. I wasn’t hard, but as he massaged my pants, I couldn’t help that it felt good. He caressed my bulge, gripped it, and rubbed it. Everything felt so strange, and I was still frozen. I kissed him back a little with a tightly closed mouth, hoping to break the mouth-to-mouth contact long enough to say I wanted to leave, but he stayed on me and didn’t give me any space. It was like I couldn’t breathe.

I realized that in spite of how odd everything felt, there was a warmth in my pants. His fingers were focused on the tip of my erection. I had gotten hard! He knew I was hard and knew exactly where to rub me! That seemed totally embarrassing. My hands were resting like stones on my legs. I was too freaked out to react when he broke the kiss for a second and said, “Do me too.” And grabbed my right hand and pressed it onto his jeans where I could feel what was obviously a rock hard penis. I turned to look out my window, and he said, “There’s nobody around, and nobody is looking over here.” I had wanted to feel a penis in my hands for as long as I could remember, and started rubbing it with my hand and massaging the bulge in his pants. I ran my hand up and down what I could feel was his shaft. He thrust his hips to push it into my fingers and made a little sound like he was enjoying it. I started kissing him back a little with my lips, but didn’t open my mouth. Pressing his advantage, he started undoing my pants with one of his hands, and his own with the other.

As he pulled my dick out of my boxers he said, “You have a huge dick.” I felt like he was lying. As he started stroking me, my stomach muscles began to twitch uncontrollably. The warmth of his bare hands on my penis felt amazing, and I noticed that there was a lot of lubrication from an embarrassing about of precum. I was losing control, and I started opening my mouth a little to let his tongue touch mine as we kissed. He got his pants open and pulled out his penis, grabbed my hovering hand, and used his hand to form my fingers around his dick and started moving it slowly up and down. He was slippery with more precum than I was. His was a bit smaller than mine. I stopped kissing him and looked down. I just watched my hand holding and moving around on his beautiful little penis. The precum was shining in the light of the street lamps. He looked down too, and stopped jerking me.

“Do you want to suck it?” He asked. “Kind of.” I replied, but even before I got the words out my head was already moving toward his lap by some invisible force I couldn’t control. I had imagined this moment thousands of times, how I would go slow, kiss it, tentatively lick it more and more to savor every moment, but now that I was here, I couldn’t get it in my face fast enough. I leaned down farther, my dick still out and leaking and getting cold in night air, until my mouth surrounded him. I could taste the precum as he moaned, “Yeah.” I started to move my mouth up and down on him, as he arched his hips up to meet me. It felt so strange and different, and yet it was like I knew exactly what to do. He was so warm in my mouth as I pressed my lips around him and felt the head of his penis popping in and out. His hand started gently caressing the back of my head, and then firmly squeezed the back of my neck. The angle made it really difficult, and I came up so that I could look at his penis up close. It glimmered in the light. “What do you want to do?” he asked in a teasing tone. I found myself hungrily replying, “I want to go upstairs right now.” “Let’s go.” And he pulled himself together and zipped himself back up. I did the same, and we got out of the car.

As we walked across the parking lot toward his apartment building, I could barely breathe. He was four inches taller than me. I tucked my hard leaking penis under my boxer strap to hide my erection. The air was cold and heavy, but the exhileration of it all made it difficult to walk. I was proudly strutting, and yet terrified. Neither one of us spoke. He opened the door to a stairwell, and I followed him up several flights of stairs. We finally came out into a hallway, walked to the end, and he opened the door to his apartment. We took off our shoes at the door, and he led me past a couch and flickering television through a doorway to a dark bedroom.

He led me to the foot of the bed, and pulled off his shirt as he turned around. That was more than I imagined would happen that quickly, and I was frozen again as he reached down and grabbed the bottom of my shirt and lifted it over my head. I struggled to get my head out of the opening, and heard his pants hit the carpeted floor with the clunk of a belt-buckle. I was still pulling my arms out of the sleeves when he went for the front of my pants and unbuttoned and unzipped them. It was all happening so fast. As I tossed my shirt to the floor, in one movement he kissed me, pressed his body against mine, and put both of his hands down the back of my pants inside my boxers and grabbed my butt firmly. For a second he squeezed and pulled my butt open, but before I could register that, his hands were sliding down and taking my pants and boxers down with them. Five seconds ago I was nervous about how far this might go, and already I was stepping out of the last my clothes and being pushed backward onto a bed by a tall, slim, naked man whose assertiveness left me no room to do anything but go with it. And I was going with it.

I flopped down backwards on the bed and then scooted up on my back until my feet had room to lay out flat. My breath was shallow and rapid as he eagerly climbed onto me, and his naked body came down on mine. It felt so weird. I wasn’t ready for this. But then I felt his penis brushing against my stomach and he started kissing my neck. I lifted one hand and gently touched his side, but I was too overwhelmed to know what to do. His lips pressing against and slightly nibbling my neck caused a chill to go down my spine. He reached over and grabbed my free hand, interlaced his fingers with mine and then slammed on the bed above my head, pinning it down. I felt our erect penises bouncing around each other. He kissed my neck, my collar bone, my neck again, and then nibbled my ear. Just as I was about to jump up and run away, he released my hand, and reached out into the darkness, out of which appeared a bottle of lube, which he squirted into his hand. He caressed his dick with it, and then caressed mine. It felt so good that I uttered, “Holy shit.” He grabbed both of our penises in one hand, and jerked them together. It felt so good, and I was just staring at my shining manhood being squeezed against his by his big hand. My mouth was hanging open and my eyes must have been huge. I realized he was staring right at me and I looked up into his deep brown eyes. He said, “Have you seen this happen in porn videos that you watch?” I nodded, my mouth still wide open. “You’ve jerked off watching guys do this in porn, and now it’s happening to YOU. Your dick is so fucking hot.” I nodded and said weakly, “This is really hot.” He came back down on top of me and kissed me as he held our dicks together. He was kissing me and I was still kind of resisting when suddenly something changed inside of me. It was like I broke free. I admitted that this was the hottest sexual encounter I had ever had, and let it stop feeling weird. I was liking it. I was loving it. Maybe I was gay, or maybe that didn’t even matter. It felt amazing. I surrendered.

I opened my mouth and we kissed deeply. I wrapped one arm over his shoulders, and ran it down to his back while the other hand pressed against the side of his face. Our mouths opened wide and our tongues danced. I ran my fingers through his short hair, feeling his maleness. I reached down and grabbed his butt. I breathed and moved freely and eagerly. I started swaying and arching my hips up toward him so that our dicks slid up and down on each other. It felt so good and I kept doing it more and more. He breathed and moaned and I knew he liked it too, and that was such a turn on. I felt like I would cum in only a few more seconds, when I suddenly became aware of someone standing next to the bed inches away. I turned my head to see another naked man, his much larger penis right in front of my lips, held in his hands like he was pointing it down at me, getting ready to feed it to me. Ryan’s voice softly said, “This is my buddy, Jay. He’s cool.” Three minutes ago this would have terrified me, but I was so turned on that I just said, “Hey.” As I grabbed his massive penis and craned my neck to take the head of it into my mouth.

His dick was huge, definitely bigger than mine, and as I stretched my jaw to take it in, I worried that it would be too big. It seemed to fill my whole mouth. Jay moaned and said, “Oh, fuck yeah.” as he put himself into my face. I moaned back. The head of his dick popped in and out of my lips, and I started curling my tongue to run it along the underside while it was inside of my mouth. He moaned deeply, and I noticed that his precum tasted different than Ryan’s. I was totally caught off guard by a second man being there, and only now did it occur to me that I should freak out about this. But just as I started to get unbearably nervous, Ryan moved down the bed between my legs and put his warm mouth around me. It felt so amazing, like I was warm and wet all over my body. Ryan’s hands roamed around between my legs, until I wasn’t even sure what was happening down there. I felt like I was being enveloped by the tentacles of some alien creature, and it felt better than anything I had ever felt before. I kept sucking Jay, who occasionally moaned. So did I.

As Ryan continued to work on me, my stomach started to feel warm. I was losing the ability to focus on the dick in my mouth, and Jay started slowly thrusting his hips to do the work for me. It was then that he put himself as deep as he could go, and to my surprise I didn’t gag. In fact, there was something extremely pleasurable about the feeling of his massive penis gently pressing against the back of my throat, and I started moaning louder. I knew I was going to cum soon, but so did Ryan. He stopped sucking me and was moving around. I heard the lube bottle squirting and the sound of lube rubbing. Then he aggressively lifted my knees high and climbed on top of me. As he sucked my nipple, I could feel the tip of his penis bouncing softly on my butthole. He positioned himself upright, and grabbed both of my hands and pressed them into the bed above my head. I knew what was about to happen, but everything felt so good that I wasn’t even scared anymore. Jay kept sliding himself in and out of my mouth and saying, “Oh, yeah. Oh fuck. Uhh.”

Ryan pressed his lubed penis gently against my hole, and met a good deal of resistance. The exciting sensation of touching soon gave way to pressure. Then more pressure. My ass started to open slowly. It seemed to open wider and wider and wider until I thought that something would break, then all the sudden the tip of his head passed my hole, and he slid in what felt like miles. I let out a guttural groan on Jay’s cock. “You good?” Ryan asked? I responded with a hungry, “Mm-hm.” And then surprised even myself when my shaking thighs lifted my butt and extended it onto him and he went in so much farther that I moaned long and low as it hit a point of intense pleasure. He let go of my hands and gripped my bony hips as he started working with his dick in and out. It felt amazing. He was inside of me, stretching me in every direction. “You are so fucking tight. This is definitely your first time.” I loved that Ryan was fucking me. I loved that his hard and hot penis was inside of me. I thought, “This is gay sex. He’s having sex with me. ” I loved the friction as he went in and out, the way the tip of his penis popped a little on the edge of my hole, before sliding back in to hit that point of unbearable pleasure. I loved the feeling of his hip bones pressing into the back of my thighs, and the pressure with which he bent me until my knees were over my chest. Ryan moved inside of me fluidly, arching his back as his butt bent down and tensed to thrust himself into me. Every thrust was a wave of pleasure, almost seeming to press every part of my penis from the inside. I noticed in all of this that my precum was dripping onto my stomach and getting cold there. All the while Jay kept gently sliding himself into my mouth over and over, my lips swelling around him.

Ryan kept telling me I was doing great, and that I felt so good on his dick. Jay kept breathing and moaning. After a little bit, they must have looked at each other and signaled it, because they both started going into me and out of me in unison. I was full of dicks, and then they’d withdraw, and then I was full again. I moaned in deep pleasure. Then they started going back and forth. Jay would go into my mouth while Ryan pulled out, then Ryan would go into my ass while Jay pulled out. I moaned again, deeper than before. Ryan laughed a little and said, “I think he likes it.” Jay chuckled and said, “Oh, yeah.” They said like they owned me. I was amazed at how hot this was. I was getting fucked by two men at the same time and I was loving it. My ass stretched and my lips rubbed until I felt worn in and used. That feeling was the hottest thing. I felt like they were using me, and like I had no control over what was happening. And I was letting it happen. I was letting them take me without a fight. The smacking of Ryan’s hips against my thighs was starting to feel wet, and a bead of sweat ran down my chest. Ryan’s hands slid around my smooth sweaty hips, across onto my stomach, and then underneath my bouncing, leaking penis. His fingers closed around it and he started to jerk me. I went weak and started shaking, and whimpered a jittery moan.

Jay was thrusting into my mouth faster, and his dick seemed to swell wider in my mouth. Then his rhythm started breaking. He grunted, “oh, fuck.” And grabbed the back of my neck to hold my head in place while he put himself deep into my mouth. His penis jumped, and he thrusted a little as his stomach muscles tensed. There was a loud, “Ugh!” His penis jumped again, pressing against every part of the inside of my mouth as it pulsated. Another “Ugh!” and with the next jump, a huge amount of cum slammed into the back of my throat. Before I could swallow it there was another, and another. I wanted to cough, or back off, but I groaned and put my mouth around him and swallowed hungrily. His pulsating penis bouncing against the roof of my mouth as I swallowed his semen over and over. The pulsating slowed down, and I was able to move up and down him. He started to soften in my mouth, and then he pulled himself out, my lips struggling to keep him. At this point I realized that a large river of his cum had leaked out of my mouth, and it had run down my face and was making its way down my neck.

I was so turned on. Ryan’s rhythmic thrusts and jerking continued. I registered that Jay was saying something about the best blowjob he’d ever had, but I had lost all feeling in my face. Every nerve in my body seemed to be in my ass and my penis, when Ryan said with a breaking voice, “I’m cumming!” He thrust himself into me as deep as he could go, and stayed there, rigid and quivering. I felt his penis bounce inside me, tickling a spot I never knew existed. It bounced once more, and without even meaning to, I let out a moan that was breathy and almost effeminate as my penis jumped, spraying cum all over my chest. Each time Ryan’s dick pulsated inside of me, my dick jumped again, spraying another load of cum while my asshole tensed around him. It was like we were cumming back and forth, him deep in my ass, and me all over my chest, my arms, the bed. I felt like I was cumming on him, as my ass grabbed him with each pulse. We were moaning in unison, each one deeper and breathier than the last. His throbbing subsided and so did mine. My penis relaxed and draped itself across my stomach. I realized that I had a huge smile on my face. I was panting. Ryan pulled out of me, and I felt his cum dripping out and tickling its way up my butt crack. He threw a towel onto my chest. I cleaned myself up as quickly as I could and put my clothes back on while they watched. Neither one spoke. I eeked out a weak, “I think I should go. ” Ryan said, “Yeah, man. Did we show you a good time?” As I slipped my second shoe on, I said, “Yes.” And then opened the apartment door as they started kissing each other. I shut the door behind me and went down the stairs alone.

The cold April night hit the sweat as I walked across the parking lot. My mouth and my ass still felt warm from the use. I noticed my walk was different. As I sat down into the car, my butt swished first into the seat in a way that was different from before. I shut the door and sighed. I could still smell Ryan in my car. I noticed that cum was still leaking out into the seat of my pants, and noticed a cold spot on my shoulder. My shirt was wet with a big drop of my own cum that had landed there. I had missed it while cleaning myself up. I laughed to myself out loud, and said breathlessly, “Well….I’m gay.” I drove home, and couldn’t sleep all night.

Report
What did you think of this story?
Share Story

In This Story