The first time.
When I was younger I had a small tight knit group of friends from my street and we did everything together. I was closer to one friend in particular, CB. I looked up to CB because he was two years older than me so of course he had to be so much more mature. He and I hung out way more with each other than we did with anyone else in the group. We did everything together. Rode our bikes for miles, played pranks on the other friends and generally became one another’s best friends.
CB had a rough home life. He was a single child that was the product of divorce. Granted it was awesome for him that he got two Christmas’s, but then again, it was two Christmas’s. His mother was a religious tyrant, always yelling at him and our group quoting only the most hateful things she could find in the Bible. She was quite a hefty woman that often got stuck in chairs/doorways and has on multiple occasions flipped a picnic table by simply sitting on it. His dad only came around when something needed done to the house or he needed to pick something up. A little more than a flyby father. I remember he wasn’t much taller than me at that age and he wasn’t skinny or fat. Kind of a weekend beer binger type. Mom is white and dad is black. Typical black guy regretting getting the morbidly obese white chick pregnant.
My parents recognized how hard it was for him at home so they offered for him to stay at our place several nights a week so he could get a decent meal and a few nights without religious belittling. This is were CB and I became a lot closer. We began pulling all-nighters so we could play with everything . Legos, video games, BB guns. We even snuck out during the night a few times taking our bikes out way beyond the safety of my cul de sac. The rush of being outside of my house in the wee hours of the morning was alien to me. I was officially a bad boy.
When we got home from my first midnight outing, my body tingling from excitement, I told CB how I felt about what we did. He told me that feeling fades away after a while. He seemed so cool brushing it off like it was nothing. I was getting another feeling I couldn’t understand. I hadn’t experienced it before. I felt a mixture of elatedness, embarrassment, and something else I couldn’t put my finger on. I felt like I needed to pee but nothing was coming out.
~I was still so innocent. I still believed in Santa and the Easter bunny. I fell for the half eaten cookies and milk sipped from perfectly so that there is the bead of dried white milk down the side. I didn’t really know what sex was beyond the beginner sex Ed they teach in elementary and middle school. I was still safe from the woes of the world. I didn’t know there was evil in the world let alone what evil really was.~
I get in bed after trying to use the bathroom. CB already halfway tucked into my bed. He could have slept on the couch or in one of the other rooms but what is a sleepover if you aren’t actually hanging out the whole time? As I’m tucking myself into bed the sheet and blanket brush by my hardness. I shamefully try to tuck myself away so CB wouldn’t find out. I couldn’t. It was like there was too much to hide. I quickly flip over to my side from my back. I guess this moved us enough for him to really take notice. He asked me if I was alright and I gave a quick but sharp yes. Lies. He knew it. And I knew he knew it.
He turned over to face my back. I then hear this much more mature voice, albeit 3 years. It was somehow deeper. What seemed like deeper than how my daddy talked. I heard it in my ears, but I felt it my whole body. “What’s the matter,” he says again almost forcing the words out of my mouth.
I told him about my dilemma. How I was excited but I couldn’t figure out this new feeling. He said that was part of being a bad boy. This sent chills down my spine. I freeze as I feel him inch closer to me. His every breathe hitting my neck in a way that I had never felt. What was going on? I wanted to get away. It felt like I really had to pee again.
I begin to get up to go to the bathroom and the feeling goes away. In the shuffling the blankets CB sees me. I see him see me. My privates. My shame. He giggled in a way that was both comforting and scary. He told me to get back into bed and then he asked me if I really had what it takes to be a bad boy. Not wanting to seem immature or lame to the person I looked up to, eager nervousness choked out an affirmation that barely crossed the line of consent.
With a quick snap, CB and I were now under the covers. As the air began to become a cocktail of our breath, his hands begin to explore. I was petrified. Frozen. I had only seen mommy and daddy touch like this but it never went below the waist. CB had gone past my waist but not past my thigh. I really had to pee. I thought I couldn’t handle it any longer. Just before I’m out the door, he tells me that this is normal and that I don’t actually have to use the restroom. It was just how your body works. Innocent me believed him. He was my best friend. I trusted him because he was an “adult” in my eyes.
As he is assuring me that everything that’s going on is normal and happens every day after a certain age. I get back into bed. Immediately CB had his hands all over me again. This time was more aggressive. He pulled me onto my side so that I’m facing him. I feel his fingers sliding down from my back to just under my bottom with a hard squeeze. I hadn’t experienced anything like this before. It hurt me but for some reason I stayed. As I let out a little whine from unexpected ass grabbing, I feel a sharp pain ripple down me.
He spanked me. He said everything was okay earlier. Why did he spank me? I wasn’t in trouble. Or was I? The only person that spanks me is mommy. I start to tear up. CB tells me that’s just how adults say they like each other. He continues to slap my bottom like I’ve been a bad boy. I still didn’t like it. Each slap sent a jolt of pain through my body. I only liked that he liked it. I wanted to impress him.
Soon he puts my hand on his privates. And he begins to grope mine. It was….so….big. I was nothing compared to what he was. He guides my hand. Up and down the length of his shaft. He tells me to keep up with this motion as he is physically is growing in my hand. It was already so big before. I didn’t think it could get any bigger. CB reaches around to my butt again. I think he’s going to spank me. Instead he takes what feels like all of his fingers and pushes them deep into my tight virgin hole.
I squirm away from him saying that I was okay with the spanking but not whatever that was. He tells me since I’m only used to things coming out of that hole there might me a weird feeling the first couple times. I gave a shy understanding and he comforts me for a moment. He guides my hand back down as he again explores my hole. It’s uncomfortable but I get used to it. Every time he goes past my hole, he pushes his finger in deeper and deeper, slowly dragging it out as his hand slides over my hairless ass. As if instinct kicked it, I wrap my hands around his third leg. It was like it, itself, was alive. It throbbed in my hands. Seeming to grow some and shrink over and over but still fully hard.
I stroke his snake with long, slow motions. I could tell he liked this by his smiles and happy noises. I continued this for a while until he asks me if I’m okay. I look up and give a meek yes. As soon as he had confirmation from me, his hand begins to push my head down to his waist. My eyes meet his and he tells me to act like his pee-pee is a lollipop. He tells me to first stick my tongue out. CB grabs the back of my hair with force and gently guides the tip of my tongue to him. Up and around his head. Light shined from the trail of spit my tongue left behind. . Still locked into each other’s gaze, he instructs me to open my mouth. Slowly, past my lips to the back of my tongue. It filled my mouth. My lips were pretty stretched out.
CB lets go of my hair and says to grab his member. I do so with both hands. There was so much. I could have grabbed it with another hand and there would have still been a lot left. He wants me to bob my head up and down. With my tongue sticking out, I slowly take him into my mouth. He rocks his hips making it go back just a little bit more. I immediately gag. Tears swell up in my eyes. As I was Looking up to CB I was expecting him to say stop since I almost threw up, but I guess the combination of me gagging and crying only turned him on more. He grabbed the back of my head again and guided my lips back to the head of his cock. I was panicked. I knew if it happened again that I would certainly throw up.
As I get into the rhythm of bobbing my head up and down, every 4-5 bobs hit the back of my throat making me gag. After a few long minutes of trying not to puke in his lap he makes me get up on all fours. He is so long the head of his dick is still in my mouth. He then gets on his knees and grabs my ears with a handful of hair. Just as I am swallowing all the spit that has already been produced, he then forces his hips forward shoving his long meat past my throat deeper into my body.
I begin to panic. Tears began to form, my eyes bulged out, unable to control my body from convulsing. CB held it in for only a few seconds but it felt like an eternity. He pulled it out and made me look at him. I could feel the thick, slimy spit that trailed from the back of my throat to the tip of his cock. As I gasped for air he told me I was being a good, bad boy. He grabs the base of his dick, aims it at my lips and thrusted his hips forward again. Before I was able to catch my breathe, his long cock was past my throat deep into my body. This time was different. He didn’t just leave it there like he did the last time. No. He began pumping my mouth and throat. His head felt like it would come out of my mouth only to disappear back down my body. His body got closer and closer until every pump buried my face into his abs and his balls slapped the underside of my chin. I was definitely crying. But this was a different kind of crying. I wasn’t sad or upset. More scared than anything, which I found exhilarating at that age.
I gave in and let it happen. I was no longer myself. In my mind I became a thing. Every thrust de-humanizing me.
CB started to go faster. The thick mucous from my throat filled my mouth, beginning to spill out. All of a sudden he stops thrusting quickly. He begins to make long and powerful thrusts. Every third thrust popping out of my mouth but immediately finding its way back through my lips and throat deep in my body. After a few minutes of this he grabs the back of my head, trapping his cock in me. My face is smushed on his abdomen when I feel a warmth explode into my stomach.
CB twitched as he slides his still throbbing cock from deep inside my throat. Sticky spit and white cream spilled from his head and down my chin. The warmth he dumped into my stomach filled my body. I felt used but also fulfilled like I served I higher purpose.
We laid down next to each other in silence. The faintest sound of CB catching his breath. He rolls over and his still hard cock thumps across my thighs. He whispers in my ear that he wasn’t finished. I didn’t know what else there was. As he flips me over facing away from him, he rubs my butt and I immediately remembered when he stuck his finger in me and make the connection. I turn over and beg him not to. I got used to his finger but it still hurt a lot. I stand up and refuse. He looks at me and asks me if I still wanted to be a bad boy almost like it was life or death. Reluctantly, I follow his instructions. I get back in bed and lay down facing away from him. He pulls out a really slimy liquid and puts it on his dick and rubs it in between my ass, slowly going over my hole. It was relaxing but I was still very tense and nervous. As he rubbed he would stick a finger in and out. CB pulled me on my hands and knees but then pushed my upper body down forcing my head into the mattress. He put more of the slimy stuff on me and him, then with one quick motion, sank himself deep into my asshole. I gasped and tried to get away.
He was too strong. Anything I did only made him grab on and force himself into me harder. I soon realized nothing I could do could stop this. So I gave in. I let it happen. Once he saw that I stopped struggling he loosened his hold on my body and changed to grab my hips. Relaxing my body helped. It didn’t hurt as much. As he rocked himself back and forth, he pushed and pulled me in the opposite rhythm so every time we met it slammed into me. I could feel every meaty inch sliding in and out. This feeling was something I grew to enjoy, almost crave. CB did this for about 5 minutes before his breathing got harder. I could tell what was going on since he did the same thing before when he exploded warmth down my throat. He stops and slowly slides himself out of me. I could feel my newly stretched out hole snap back closed. With a quick motion, he pulls me on my back and throws my legs in the air. He forces himself in me again. This angle was different. This angle was tighter. It’s almost like I felt more of it.
If this wasn’t the first time I made love with someone I don’t know what is. The friendship CB and I had would have been considered love at that age. Now it’s deeper than that. We were connected in the most intimate of ways.
In all of the initial shock, I didn’t realize I was really hard myself. This was also a new experience. I hadn’t yet began to explore that part of my body until now. CB grabs a handful of me and strokes up and down to the same rhythm he is slowly pounding my ass. His breathing gets quicker as does his stroking and pounding. After a few more minutes of him slowly increasing the tempo he fucked me at, I began experiencing another feeling I’ve never experienced before. It was almost like I was being filled up with joy and excitement. By now CB is fucking me really hard and really fast. I squirm with every pump filling this feeling more and more. I feel the familiar warmth explode in me again but deeper in my body this time. As CB drains himself in me once again he is still stroking me. I grab onto anything I can trying to not release this feeling. Before I realize it I am exploding with a warm ooze. It shoots high Into the air only to land back on my chest and face. I was immobilized. This feeling was unexplainable. I had cum for the first time ever.
CB pulls his half limp dick out of my used hole, Cum oozing out. He lays down and falls asleep almost immediately, leaving me there by myself with the thoughts of what just happened.
Source: reddit.com/r/eroticliterature/comments/g33o7c/the_first_time