More than Just a Shoulder to Cry On

I remained taciturn for a few seconds. It felt as if we were both waiting for the other person to be the first one to move or speak.

"Then she unzipped my jeans and pulled out my cock, like she already knew that I was hard. She reached down and wrapped her hand firmly around the base."

I picked up my beer and took a drink. Suddenly, I was feeling more tentative. I wasn't even sure that he wanted me to touch him in that way, and this was definitely not how I had envisioned my first time giving a handjob.

"She really had no way to be completely certain that I was okay with her grabbing my cock... but I was. I knew that even if she didn't give the best handjob in the world, it would still feel nice. So, I was happy when I felt her hand wrap around my dick."

I no longer felt concerned about whether Chase wanted me to envelope him with my hand. It didn't stop me from worrying that I wouldn't be good at whatever he wanted me to do after that, though. I pushed that fear to the side of my mind; I wasn't going to let it dictate my actions.

I moved my right hand towards his dick. I noticed that his huge cock made my hand look small in comparison. I had never had that issue with my own six inches. I carefully started to wrap my palm around his member; he startled for a second since he hadn't been able to see that I was about to make contact.

"Her hand felt nice and warm. I always like it when someone isn't able to completely wrap their fingers around my dick."

I noticed that he was correct; I was not able to touch the tips of my fingers together. There was about two inches of space between the tips of my thumb and index finger.

"She started off slowly. She only really moved her hand up and down about two inches, while still keeping a firm grasp. The pressure near the base helped make me even harder. She used her free hand to continue to play with my nipple."

I had to contort myself a little, as I sat beside him, to be able to touch his left nipple with my hand while I held his cock in the other one. I started playing with his nipple first since I felt confident in that domain. After Chase moaned again, I began to slowly pump his cock in the way he had described.

I was impressed my how firm it was; I felt a large vein pressing into my palm. I was uncircumcised, so that moment was also my first time having any contact with a cut dick. Chase didn't say anything as I continued to stimulate him with both hands for the next two minutes. I could tell that his dick wasn't getting any less firm, which I took to be a good sign.

"I told her that what she was doing felt nice. She loosened her grip just a touch and began to glide her hand from right where the head meets the shaft down to the top of my balls. I really liked feeling the sensation of her hand pressing into these two places at each end of its journey."

I loosened my hand and started trying to mimic what he had described. I realized it wasn't at all dissimilar to what I enjoyed, even if it was a little different in that I like more of a twisting motion as my hand went up and down.

"She made sure that her grip wasn't too loose though."

I tightened my fist just a bit as per his request. I wasn't entirely sure if it was exactly what he was asking for; however, it seemed like the large vein was protruding more. I took that as a positive endorsement.

"She took her hand off of my nipple and started to play with my balls. She did it really softly, tickling them with her fingertips."

I moved my hand down to Chase's nutsack. It was covered with the same fiery red hair as his pubic mound, though it was sparser on his balls. His nuts tightened a little bit as soon as I touched them. I continued to stroke his cock at the new, faster pace at the same time.

"I asked myself what this girl would be willing to do in an alleyway. I was amazed that she was gutsy enough to do this kind of thing in public. I didn't know her well enough to make any assumptions. I decided that I should just ask and see how she would respond."

Chase pulled his head up from its reclined position; he opened his eyes so that he was looking directly at my hand as it jacked him off. He cracked a small smile. He gazed over at me, making direct eye contact. I felt butterflies flutter in my stomach.

"I looked her right in the eyes. She was really attractive, even if she seemed like she was the type to be hard on herself. I told her, 'You have really nice, full lips. I would love to see what they feel like around my cock.'"

Chase reached up with his left hand and placed his thumb against my lower lip. He softly dragged it across the soft, pink tissue. He carefully inserted the tip of his thumb into my mouth and rested it on my tongue.

As my tastebuds began to register the subtle salinity of his skin, I realized that I, too, was rock hard. I hadn't been paying attention to my own physical sensations; almost all of my attention had been focused on Chase. But there was something about his last action that pulled me back into my body.

I massaged his thumb with the tip of my tongue, as if I were emulating the circular pattern my finger had been making while caressing his nipple. He pulled it in and out a few centimeters, just enough to tease my senses. Saliva began to pool in my mouth. I was quite literally drooling.

Chase removed his thumb and rested his hand on my thigh. I felt the edge of his pinky finger rub against the bulge in my jeans. My dick twitched in anticipation.

"So...?" he asked.

I felt myself blush. I had watched enough gay porn to understand what I was supposed to do. I still worried that I wouldn't be any good at it. Yet again, I decided to throw caution to the wind.

"What did she do next?" I asked.

"This isn't about her anymore," he said. "It's about you. How about you just try whatever you think feels good to you, and I'll tell you how I like it?"

Suddenly, the fear came rushing back. I'd been so much more comfortable receiving instruction, and I'd felt safer with the story serving as a barrier between us. I wasn't even entirely sure how I'd want to start. I looked down at his nearly nine-inch cock; I was terrified... but I realized that I was also excited. I felt myself sliding towards the edge of the loveseat before I realized what I was doing. I dropped to my knees and positioned myself between Chase's open legs.

Chase smirked as he registered the emotion in my eyes. I must have looked like a novice mountaineer standing at the base of Everest. His dick was only a few inches in front of my face.

"It's really big," I mumbled. "I don't think I'm going to be able to take it all."

"I don't expect you to do that," he said. "Like I said, just do whatever you think would feel good."

I reached up with my right hand and wrapped it firmly around his cock. I started to stroke it again in the same manner I had been a few minutes earlier. I remembered the way his balls had reacted when I'd touched them.

I moved my face closer to his large, hairy nuts. He preemptively shimmied forward to the edge of the loveseat so that they were no longer resting on the cushion. His pendulous sack gently swayed in front of my mouth.

I stuck out my tongue and started to use it to lick his balls. I didn't attempt to find a rhythm. Instead, I let my soft tongue do what felt natural. I experimented with gently nibbling on his sack, as well as taking most of his right ball into my warm, moist mouth. Chase's nuts would sporadically twitch as I simultaneous played with them and his cock.

After a few minutes, I realized that I was staying at base camp for fear of the climb ahead. I halted my tongue bath and pulled back a bit. I stopped pumping his dick with my other hand. I could see that Chase seemed curious about what I was going to do next. I let go of his dick; it wobbled, but continued to point straight at the ceiling.

I leaned forward and extended my tongue again. I started to drag it along the underside of his dick from the top of his balls to the opening of his urethra. His warm flesh felt pleasant as it pressed against my tongue. I went to repeat the action, but realized that it was awkward; his dick didn't want to stay completely still.

I reached up with my right hand and cradled his cock from the topside. The added support allowed me to really bathe his dick with my saliva. I thought I could feel Chase respond more when I dragged my tongue across the underside of his cock head. I gave that area extra attention by stopping to tickle it with the tip of my tongue every so often.

"That feels nice," he said. "My cock head is really sensitive."

I interpreted that as appreciation combined with some guidance. I wrapped my right hand around his dick again; it was now slick with my saliva. It made it easier to jerk him off in a more fluid motion. I continued to only move my fist to the place where the shaft connected with the head.

I leaned forward and used the tip of my tongue to tease his cock as I continued to stroke him. I made small, circular motions. Chase moaned with pleasure; his dick was throbbing with greater intensity. I took my left hand and reached up to his chest. I used my thumb to stimulate his nipple in a way that mirrored what I was doing to his cock.

I was suddenly feeling emboldened. I had always questioned if I would be able to do this well, and it wasn't nearly as difficult as I had imagined. Hearing Chase moan had made realize how much I liked knowing that I was pleasing him.

"Do you like that?" I asked.

"Fuck, yes," he said.

"Do you want me to take your huge cock in my soft mouth?"

He took a moment to react, as if he was trying to process the change in my demeanor. I thought he could tell that I was less anxious and starting to enjoy myself a bit more.

Chase leaned forward so that his face was less than a foot from mine. He placed his hand on the nape of my neck without breaking eye contact. I wasn't sure what he was going to do for a second; he began to slowly pull my face towards his. It wasn't until our lips were touching that I fully accepted that he was kissing me.

I froze up a little bit, but Chase had enough passion for the both of us. His tongue explored my mouth and teased my own inactive tongue, which had been doing a much better job on his dick a few moments earlier. My heart was racing; I let myself ease into the kiss and followed his lead. It only lasted for about thirty seconds before he pulled away. I was still trying to process what had happened. Oddly, it had felt more intimate than sucking his dick.

"I really, really want you to take my cock into your hot mouth," he said with a nonchalant smile.

As if on autopilot, I leaned forward again. I had never stopped pumping away at his dick or teasing his nipple, even as we had been kissing. I parted my lips and took his cock head in my mouth. It was only a few inches, so I wasn't at all worried about choking -- not yet.

Again, I let my wet tongue take the lead at first. I didn't beat myself up for being a cautious explorer; I was already away from camp for the very first time and braving the mountain. I even smiled at the stray thought that, despite my slow and steady pace, I was actually trying to cause an avalanche.

I focused on stimulating his urethra and glans since these seemed to give him the most pleasure. My mouth was producing so much saliva; it was starting to drip down his shaft as well.

I began to slowly move my head up and down just a bit. I tried to do it to align with the stroking motions I was making with my hand. I was certain that I wasn't doing it nearly as well as what I had seen in porn, but I was trying my best. I hoped that my excess saliva was heightening the experience.

I started to go a little further down, but I quickly became aware of his girth. I had to strain my jaw in order to accommodate him. It wasn't painful, just mildly uncomfortable. Every time I bobbed my head up and down, my lips pushed past the sensitive place where his cock head met the shaft. I tried to use my tongue to caress the underside of that area at the same time.

"Fuck, that's good," he moaned as he placed his right hand on my head.

His words sent a thrill through me. Knowing that I was pleasing him turned me on in a way that felt so unlike regular sexual arousal. It was warmth in my chest and a tickle in my brain. Eager and encouraged, I kept doing the same thing. His hand started to tussle my hair and his fingertips massaged my scalp. It was another thing that shouldn't have been a big deal, but it sent a surge of energy through my body, pairing gloriously with the good feelings from his moans of pleasure. I immediately felt my dick begin to throb.

I wasn't struggling much with the four inches I was taking into my mouth. I wondered if he wanted me to go deeper. It seemed to be a common thing in porn that a guy would put his hand on the cocksucker's head and use it to encourage the guy to take more of his dick. I halted my bobbing for a second and let his head sit on my tongue.

I didn't think it could be that hard. I tried to force myself to relax all the muscles in my throat, and I unintentionally held my breath. I lowered myself onto his cock. I started to feel a discomfort as his head made contact with my tonsils, but I pushed onward.

"Oh, God," he moaned.

His dick crossed the threshold from my mouth to my throat as I took another inch. I could tell that I had gotten two-thirds of his massive member into my mouth. I suddenly felt tears rushing to my eyes. Chase's hand was now cradling my head rather than massaging it.

"That's so fucking good," he said. "Your throat feels fucking amazing."

I went to pull my head back, but I felt his hand holding it in place. I knew that he was loving my throat, and I was sure that he didn't know that I was struggling. Without moving, it started to feel less uncomfortable. I decided to try to take just a little more since he liked it so much.

I felt it throbbing against my throat as it pushed deeper. After a few seconds, my throat started to spasm. Tears started flooded to my eyes; I felt like I was literally choking.

"That feels so fucking good," he moaned. "Whatever you're doing is driving me crazy!"

I quickly tried to yank my head away from his crotch as my throat muscles convulsed. He continued to hold my head in place as he loudly moaned. I could tell he was loving it; his cock head was getting massaged in my slick throat as I gagged.

I stopped stoking his nipple with my thumb. I swiftly and forcefully pinched it.

"Ouch!" he said. "Oh, shit..."

He removed his hand from my head as he registered that I was struggling. I pulled back, feeling a sense in immense relief as his dick exited my mouth. I started coughing; I could feel myself turning a little red. The tears were still welling in my eyes even though I knew I wasn't going to cry. I wasn't upset. I was just learning a lesson about overexerting myself.

"I'm so sorry, dude. I didn't have any idea. I'm so stupid. I should have known better and told you to slow down. I have been with girls where it takes them weeks of sucking me off to get comfortable going that deep."

Chase was leaning forward. He placed his hand on my shoulder. I had stopped coughing and was focusing on regulating my breathing. I was staring down at his feet. I started to feel stupid. I knew I had completely ruined the mood.

"Are you okay?" he asked once I seemed to be back to normal.

"I'm fine," I said. "Just mortified."

"Dude, you are too hard on yourself. Everything was feeling really fucking amazing. You didn't even need to try to deepthroat me. It was pretty great when you were stoking me and focusing on sucking the tip. I was probably only a few minutes from busting when you stopped doing that."

I felt mixed emotions. I was relieved to know that Chase had enjoyed what I had been doing, and I felt dumb for trying to do too much my first time giving a blowjob.

"I'm sorry I ruined it," I murmured.

"Ruined what?" he asked.

He placed his hand under my chin and tilted my head so that I was looking into his eyes. They sparkled with kindness. He nodded down at his dick; it was glistening from all the saliva I had covered it with. I realized that it was still completely hard.

"We can stop this, or we can keep going. As you can tell, my cock is hoping that we keep going."

I chortled and rolled my eyes. I appreciated his attempt to shift the mood. I reached forward and grasped his cock again with my right hand.

"Just don't go deep this time," he said, "and remember to be mindful of your teeth. It can become more of an issue when someone is trying to take it deeper."

I nodded. It seemed like good feedback without being too critical. I would just go back to doing what had felt comfortable for me and made Chase feel good at the same time. My new goal was just to be able to know that I had made him cum.

I started to stroke his cock again as I played with his nipple. His dick felt slippery wrapped in my hand; all my drool had acted as an ersatz lubricant. Chase was moaning every so often. I learned quickly that every time my fingers crossed the threshold from his shaft to his head, he just couldn't help himself.

A few drops of pre-cum dripped from his tip and dribbled down to where I was pumping away. He let out another moan; it made me feel good to watch him leaking. It felt like some concrete proof that he wasn't pretending to enjoy what I was doing.

"I'm getting close," he said.

I knew that I had to make a choice, and that I didn't have much time to decide.

I leaned forward and took his cock head in my mouth again. The remaining pre-cum clinging to his dick tasted salty and warm. It wasn't thick at all though, which was surprising.

"God, yes," he said.

I didn't slowly explore that time. Instead, I went right to work. I started bobbing up and down while letting my tongue caress his cock head. I kept jerking him with my other hand to match the same pace of the blowjob. I realized that I had sped up without thinking about it. It had just seemed like the natural thing to do when someone was getting close to cumming.

I moved my other hand away from his nipple and used it to cradle his balls. I was hoping it would bring Chase pleasure, but to be honest, part of the reason for the change was that I wanted to feel his nuts when he came. There was something about the idea of cradling his balls as he exploded that excited me. I noticed that my own dick was starting to drip a little pre-cum just thinking about it.

I kept going at it. I became more aware of the fact that his dick was throbbing harder than it had been this entire time. I thought about what it would feel like to have it throb like that inside of my asshole.

"I'm going to cum, I'm going to cum!"

I realized we hadn't negotiated what to do in this situation. I had already embarrassed myself earlier and I didn't want that to happen again. I thought about what I wanted. The answer was obvious; I wanted to swallow him.

I didn't let up on my oral action since I thought that might derail his orgasm. His balls started to contract; I could feel them pulling closer to his body. A hot load of cum spurted from his cock head into the back of my mouth. I continued to bob up and down while frantically swallowing.

"Don't stop," he moaned.

I kept going as more jets of jizz erupted from his throbbing dick in rapid succession. Despite my desperate attempts to gulp down the salty, viscous fluid, I just couldn't swallow it all. Some of his cum began to overflow from my mouth and drip down his shaft. The mixture of spunk and saliva made it easier to jerk him in a more fluid motion.

Chase shot two final ropes of cum. As the last bit erupted from him, I could feel him shaking. I watched as his ab muscles rapidly contracted and expanded.