Justin's Journey

The birth of a bitch bottom

It was the spring semester of my freshman year and I found my class work to be easier than my first semester. Which was good because I found my mind wandering during lectures. Rather than looking at the board, I’d find the hottest guy in the room and fantasize about him. Wishing I could service him under a desk while he does his homework. Or that he would fuck my brains out in a library bathroom or something.

I knew I needed to focus on time with friends to distract myself. Which worked for the most part, and I was able to finish out the year. Things really got easier when I went home. Surprisingly, I wasn’t thinking about guys at all during summer break. I spent it going out with friends and catching up with everyone since I didn’t see any of them during the school year. Before I knew it, summer was over and I was driving back to school.

About halfway through the fall semester, I was introduced to a friend of a friend. His name was Jack and he was also gay. Our mutual friends were trying to set us up, which was actually very helpful because at this point I was convinced I was the only gay guy on campus. Jack was adorable. Pretty short, which was unfortunate, but he had great style and a very fit body. Curly brown hair, glasses, and an attractive voice. Jack and I got to know each other over the course of the next couple months and eventually started dating by second semester.

In retrospect, Jack was not a great match for me. But I learned a lot from the year long relationship. Shortly after we started dating, things naturally progressed to get more physical. Jack was very obviously a submissive person and a bottom. Me, being a virgin, didn’t know for sure what I’d like, but ultimately just wanted to do anything with a guy at this point. When the time came, Jack stayed over at my place and I was prepared. I had bought the condoms and lube and I had a towel ready nearby. We finally got down to having no clothes on. I was laying down and Jack sat on top of me, sliding forward and back, letting my hard cock slide between his cheeks. Jack had a beautiful ass. His friends often made comments about his “dumpy”. I knew he wanted me to be more dominant and while I wasn’t super comfortable with it, I gave it my best shot.

I grabbed him by his waist and moved him to the side so he could lay down on the bed. I told him to turn around. He shifted around so we were spooning. I kept rubbing my cock along his hole, dying to enter it at this point. I reached over to grab the condom, slid it on as sooth as I could, prepped his hole with lube, and slowly inserted my tip. I felt him tense up so I laid still, just kissing the back of his neck. He eventually reached back to grab my ass and to slowly push my hips forward, guiding me into his hole. Once I was fully in, I took a second to be still and enjoy the sensation. Then I slowly began to fuck him. Softly at first, but growing in aggression. Eventually pivoted to have him lay on his stomach and me on top of him. I was then able to give nice, long, hard strokes. He was whimpering and clutching the pillow, which I took as satisfaction since he hadn’t said any real words. It wasn’t much longer before I felt myself about to blow. I slide the condom off as quickly as I could and laid my cock between his cheeks. I pushed them together, letting my dick glide between them until I shot my load across his back. He relaxed and looked back at me with a huge grin on his face.

After wiping my mess off his back, he turned around let me service him to completion, which unfortunately didn’t take long. It was the part I enjoyed most. He stayed the night and in the morning, I texted my friends our code word. Koala. One thing my friends and I had in common is that we were all virgins when we met, so we made a deal that we would inform each other when the status changed.

Over the next few months, Jack and I didn’t spend too much time together. Jack was busy with his work on his design team at school. I hung out with friends a lot, both his and mine. Jack and I saw each other a few times a week, and we usually spent our time fooling around instead of talking. Our relationship became almost solely about sex, which was good and bad. I wanted more of an emotional connection, but I was still happy to get my sexual satisfaction.

As we fooled around more and more, we’d try new things. I’d tie him up, spank him, choke him, or degrade him. It was all very hot but if I’m being honest, I just wanted to try being on the other side of it. It didn’t feel very natural being the dominant one. There were a couple times Jack was willing to top, but it was few and far between. And not quite as fun as I wanted it to be. Turns out he didn’t find the dominance thing to be very natural either. Eventually, Jack would take a co-op (an internship that lasts a summer and a semester), which would end up killing the relationship. It was hard for me at first but I eventually worked through it. I think my sexual frustration at this point was spilling out through my emotions a bit. I knew I needed to reel it in because my friends were starting to make comments about how they were worried about me.

Jack and I broke up in the fall semester of Junior year. I decided that during winter break, I was going to search for the release I needed. My mom had moved in with her boyfriend so I was staying at his house for the month. He didn’t seem to pay me much mind and he kept her distracted, so I knew I had a chance of getting out without having to comment on where I’m going. One night, I was perusing Grindr and got a message from a profile that was named “Couple looking”. I had fantasized about a threesome before but I just assumed it was a few steps away from where I was in my journey. The guy said his boyfriend was a strict top and he didn’t want to bottom all the time so he asked if I wanted to come bottom for the both of them. I was beside myself. I immediately went upstairs to shower and prep.

Once I was dressed and ready, I left the house quickly without saying anything and drove to the pinned location he sent me. It was a ratty little apartment, kind of messy, with two small dogs that yapped a lot. I stepped inside and the guy said “I’m Sam by the way. Derrick is my boyfriend, he’s in the shower he’ll be out in a minute”. I realized just then that I didn’t even know their names. I was so caught up in my own fantasy that I just walked into a sketchy apartment with two complete strangers and without telling anyone where I was. I thought to myself “I’ll die doing what I love, hopefully”. Proud of myself for not having a panic attack, I smiled and introduced myself to Sam.

“Nice to meet you, I’m Justin”

I was so awkward and had no idea what to do at that point. But Sam seemed very relaxed. He had definitely done this before.

Sam was tall and lean guy with short black hair and gorgeous caramel skin. He smiled at me and said “Let’s go get comfortable”. He lead me to the bedroom and patted the side of the bed, indicating that was my seat. I sat next to him and he turned towards me, placing his hand on my leg and beginning to rub it.

“So are you from around here? I haven’t seen your profile before”

“I am, but I go to school about four hours away, so I’m not back in town too often”

Suddenly the bathroom door opens up. I’m barely able to see the steam blowing out of the bathroom and into the dark, very dimly lit bedroom. Derrick stood there in his towel. Derrick was bigger than Sam and I. Not super tall, but he had nice arms, tattoos, and a buzz cut. He looked like a military guy to me. Derrick looked at me and smiled.

“Hi I’m Derrick. I don’t believe we’ve learned your name yet, have we?”

“This is Justin babe, he’s on break from school”

“Ahhh, a nerd. Cute”

Derrick releases his towel and it falls to the floor. My eyes follow it and then I look back up to see that he’s very much a shower and not a grower. Derrick’s huge 9” cock was dangling there like a weapon. My heart started to race and I wondered if I was out of my league. Jack was smaller than I was, so this way by far the biggest dick I’d ever seen in the flesh.

“Derrick is hung like a horse but don’t worry, I’ll get you started”

Sam begins to take off his shirt so I follow his lead. When he dropped his shorts, I saw that he was already hard, but it seemed more manageable than the beast on the other side of the room. Derrick walked towards Sam and I and they locked mouths, wrestling their tongues and swapping spit for a few seconds. Then Derrick reached for me and pulled me in. He shoved his tongue in my mouth while Sam began to run his hands slowly up and down my torso and back. Derrick’s hand was on the back of my head and he began to move it down on to my shoulder. I felt the pressure he applied and I knew where he wanted me to go. I tilted my head to start kissing his neck and then slowly moved down, kissing his chest, abs, and then his beautiful V lined pelvis. All the while moving my hands down with me, caressing his arms and admiring his toned muscles. Sam and Derrick began to makeout as I stared at what I imagined to be my ultimate demise. This thing was the same length as my head. Too intimidated to start on it, I pivot over to Sam’s dick. This seemed like an easier warm up task for me. I go to work on Sam and reach over to get a feel for Derrick’s tree trunk. I was able to get my thumb to touch my middle finger when wrapped around it, but just barely. And I just knew I’d never get the thing down my throat all the way. But I was so turned on I knew I’d give it my best shot.

After 5 minutes or so, I felt Derrick pull away. He went to sit on the bed. Back up against the headboard with his legs stretched out.

“Come here”

He put his hands on his thighs and looked down at his cock and then back up at me. I crawled up on the bed on my hands and knees, stopping for a moment to kiss him. His soft lips kissed so sensually it made me feel faint. Then I moved my head down. This was the moment. I lifted it up with one hand as the thing was too god damn heavy to stand up on its own. I felt like a snake unhinging my jaw as I attempted to engulf it. I felt him hit the back of my throat and I open my eyes to see that I’m still a couple inches away from his pubes. I remember thinking I have to try to go further, I wanted to impress him. But it would be a slow process. As I slide my mouth back and forth on his shaft, I felt a hand at my hole.

Sam had begun rubbing his hand between my ass cheeks. I pulled the anaconda from my mouth to glance back and see that Sam was jacking off with his other hand while he felt around my hole. I went back to my task. I felt like it was a game to see if I could get further each time I went down. I almost wished I could draw tally marks to indicate my progress. The more I worked at it, I felt like I was getting a little closer. I wanted to get my lips to the base of his cock so bad. I started to get distracted as I felt Sam slapping his dick on my ass. Like knocking before entering a house, it felt like he was warning me. Derrick lifted my head by the chin until I made eye contact with him. He had a huge smile on his face.

“Have you ever done poppers before?”

I shook my head.

“It’ll help, I promise. But you don’t have to if you don’t want to. What do you think?”

I nodded my head. He moved a little bottle to my nose, holding it between his thumb and middle finger. He used his pointer finger to pinch one of my nostrils shut.

“Breathe in”

I take a deep breath and within about 5 seconds I start to feel a rush. It felt like all of my blood was going to my head. Then I felt my body relax just a bit and then this wave of lust washed over me. I wanted to be fucked so bad. Sam started rubbing his cock along my ass again but this time it was lubed up. I felt it glide along my crack.

“You ready?”

I arched my back a little more as my response. I felt his tip at my hole and then I felt the pressure. I relaxed and then he slid in slowly. I could tell the poppers were helping. I didn’t feel quite as tense as I normally did. Sam began to move a little faster, trying not to thrust too hard as I had moved back down to Derrick’s third leg by that point. It felt like pure ecstasy. Forcing a giant cock down my throat while another fills my hole. At this point it dawned on me. I never heard Sam open a condom wrapper. I had never fucked without a condom before but we hadn’t talked about using one. I tried to determine if the sensation in my hole felt more like latex or skin, but the more I thought about it, the less sure I was. I didn’t know anything about these guys but at the same time, I thought it was hot. By this point the riskiness of it all made me even hornier. I decided it didn’t matter if he was barebacking me or not, I was getting what I needed. And same for him.

Time went on and I could hear them both grunting and groaning. A couple times I felt Sam bend over me to kiss Derrick. Each time he inadvertently pushed me a little further onto Derrick’s cock. It was probably the push I needed because after about 10 minutes, I could really feel my throat relaxing. I felt like my breathing was under control and I was getting closer to my goal. But my progress was interrupted.

“Wanna trade?”

“Fuck yeah”

I felt Sam pull out of me slowly and get off the bed. I sat up and rested on my legs for a second as Derrick shimmied off the bed. I turned to look at Sam’s cock. It was glistening with lube, but no condom. It made my stomach flutter knowing he just barebacked me. And I was about to get a second one. I said nothing has he wiped it off with a towel. He took Derricks place on the bed and leaned forward to kiss me. I heard the lube bottle again and got another stirring feeling. I couldn’t believe I was about to get that giant thing shoved in my other end. Sam sat back as Derrick got up on the bed behind me. He grabbed his cock with one hand and he put his other hand on my shoulder, like he was bracing me for it. Suddenly the poppers appeared in front of my nose again. I looked Sam in the eyes as if to say thank you and I took a giant deep breath in.

I now felt Derrick at the rim of my hole. He started to push but thankfully, it was ever so gently. I imagine he was used to having to ease into it. I couldn’t see anyone surviving an encounter where he just pile drives it in. My hole stretches and my jaw drops as a physical response to the sensation. I feel him rub his hands up and down my back to soothe me. I reach one of my hands back to touch his waist and he paused. It’s like I was driving now, I controlled the speed. I was guiding him. A trick I’d learned from Jack. I held still for a few seconds and then I’d pull him in just a little more. It was a slow process, but eventually I got most of him in. He starts to back out just a bit and I held completely still. He stops again and moved forward. Then back. Then forward. He slowly developed a rhythm and the strokes got longer. I was doing it! I was taking a monster cock and I wasn’t dead yet!

Derrick gripped my waist and it felt like his hands almost reached entirely around me. He continued his work to stretch me out. I was started to feel at ease again when I finally looked forward at Sam. He had one hand stroking his cock and he wrapped the other around the back of my head. He pulled me forward to make out with him and then nudged my head downward. I was fearless at this point and went for it. After Derrick had warmed up my throat, I was able to take this one with ease. My lips slide straight down his shaft until they reach the base. My nose pressed to his clean shaven body.

“Fuck yes, take it”

I moved faster, forcing his cock to the back of my throat over and over again. It seemed Derrick had decided to turn things up a bit too. For the first time since he entered me, he pushed himself balls deep. His body clapped against my ass and he held himself there.

“There you go, Atta boy, you’re loosened up now”

He pulls himself back almost all the way out and then rams forward. My face smashed into Sam’s pelvis again. I was filled balls deep in both my ends, and it was the greatest sensation I’d ever felt. I thought to myself this is all I ever want to do. Sam ran his fingers through my hair gently as I serviced him and Derrick continued to wreck my hole. It felt like so much time had passed, maybe 20-25 minutes, before Derrick grunted and pressed himself into me, holding still as his cock pulsated inside me. I felt the pulses at the rim of my hole and I could feel his warm seed being shot inside me. He bent down to kiss my back a couple times and then began to slide himself out. When his tip finally fell out, I could tell my hole was stretched and loose. Thankfully they had put a towel down because there was no way I’d be able to keep his load inside me. Sam scooted off the bed.

“My turn”

Sam placed a hand on my shoulder and another on my side, moving me to a new position like a toy. I was laying on my back, legs up and spread, with my ass at the edge of the bed.

“I’ll take care of us both. We aren’t greedy tops”

Sam squirted some lube in his hand and then pressed his other hand on the back of my leg, keeping it up. Derrick grabbed my other leg, around the back of my knee. Then Sam reached down with his lubed hand and began to jack me off. It made sense that the lube was for me and not him, because I doubted he’d need any to fuck me at that point. And I was right. Aiming his dick with just his hips, he lined it up and slid it in me with ease. Just then, Derrick, who was already on the bed behind me, scooted closer to me. Sitting on his legs, I noticed a knee brush against each of my shoulders as he towered over me right above my head. Still using one arm to keep my leg up, he used his free hand to drop his thick, heavy, still lubed dick on my face. He lifted it a few times, letting it smack back down on my face. I noticed both of my hands were free so I reached one up to place on Sam’s chest to admire his body as he ravished my hole. The other I used to take over control of Derricks cock so I could play with it myself. As I took it from him, he began to gently run his fingers along my chest.

My hole was stretched from the pounding I already took and I could feel the lube and cum being fucked out of me by Sam. He was really going hard at this point, on both my hole and my dick. Additionally, my face now had some lube on it from being smacked with Derrick’s cock. He’d also dropped a little residual cum on my chin, which he wiped up with a finger and fed to me. The combination of all of these things made me feel like such a cheap slut. I was letting these two complete strangers breed me. And yet, I oddly felt safe at the same time. They were gentle enough with me that I weirdly trusted them. My heart was pounding and I knew I was getting close.

I started to breathe faster and I pressed my hand on Sam’s chest to let him know. Sam makes eye contact with Derrick and gives him a look. Derrick takes hold of other leg from Sam, now holding them both back. Sam continues to stoke me while he leans forward and grabs on to one of my shoulders with his newly free hand. He begins to fuck me harder and faster until I blow my load all over my chest. I instinctively take over control of my own cock in the middle of my orgasm. Sam reaches his other arm forward, now having both of my shoulders in his clutch. He had my braced for the hardest fuck he could give. He rammed himself into me over and over again. My dick was twitching and I felt like my whole body might convulse at this point. I had never felt so much pleasure in my life. My hole was loose enough that I didn’t feel pain, but I was still getting a lot of stimulation at my prostate, which was like an overload of nerves at this point after I had just cum. Luckily, about 20 second later, Sam emptied his balls deep inside me.

Breathing heavy, he slowly pulled out and grabbed a towel. He wiped off my chest first and then his dick. I laid there in amazement. Dumbfounded that I was ever content with sex before this night. Derrick got off the bed so I sat up as well. I assumed this was my time to leave since I had served my purpose. I reach down for my clothes.

“Did you want to shower real quick? We would join you but the shower isn’t very big. You’re welcome to it though”

Derrick nodded in agreement. I couldn’t believe how nice they were. I told them I’d love to rinse off real quick. So I took a quick shower, got dressed, and headed for the door. Derrick was sitting on the couch, still naked, manspreading. He smiled and waved.

“Drive safe, message us when you get home”

“Yes please do. This was fun, we’d love to have you over again sometime”

Sam kissed my cheek and opened the door.

I sat in my car for a minute before leaving. I was trying to process what just happened. That was the most fun I had ever had in my life. Why had I never done it before? I was definitely going to do lots more of it in the future. I drove home and laid in bed happy with myself. My hole was a little sore already, but that ache would help me sleep satisfied that night.

Next chapter:

I graduate, move home, and further explore my lust for men.