Saying Stay Ch. 05

"Simon..."

"What is it?"

I instinctively choked back what I had been about to say.

He stopped rubbing me and just held my cock steady. "What do you want me to do Mike?"

"I want you to..." Again, my voice was failing me, the last dregs of my shame and uncertainty clogging my airway.

He tilted his head to the side, looking like a confused puppy. "Mike, I can't help you out if you don't tell me what you want." This game again.

"I want you to suck my cock," I blurted out.

"Oh!" Simon acted surprised. "Well, of course." And before I knew it he was splayed out across the bottom of the big bed, burying my dick in his mouth. The second I entered his moist mouth I wondered what had taken me so long. Simon was an insistent and energetic cock-sucker, bobbing up and down on my shaft with so much speed and enthusiasm I was slightly afraid he might rip the thing off. But the inside of his mouth, and the feel of his tongue sliding around the head of my cock, was so nice I wasn't really concerned.

I let out a moan, longer and higher-pitched than I was used to. Simon was playing with my balls as he swallowed his cock as if it was food to a starving man. He briefly came up for air, gasped, and then went right back to gulping down my meat. At about the same time I felt his other hand press into my ass.

It was a bit uncomfortable – I was used to my ass being strictly exit-only – but, in the spirit of trying new things, I eased up and let Simon slide a finger inside me. It felt strange, being penetrated, or more precisely having a part of somebody else's body inside you, wiggling around beyond your control. But it kind of felt nice too. And then I felt Simon's finger curve and begin rubbing a sensitive spot of my inner walls and it went way beyond nice.

And of course, he was slurping and sucking on my dick this whole time. I felt the familiar sensation of orgasm approaching and tried to fight it off. It would be too much, and too soon. "No," I muttered.

Simon looked up at me quizzically. "I don't want to come just yet," I said. "And besides, I... I want to do you."

He smiled and sat up. It was only then that I noticed that he had somehow lost his clothes while I had been soaking up his oral pleasure. I looked over Simon's body once again. It was a better body than mine, if we're being honest – and it was strange to even make that comparison. He was lean, but muscular, with a quiet strength radiating from his pale skin. Other than a couple tufts above his cock, his body was hairless. And that cock? It was still at half-mast, but it seemed looked smooth and attractive... almost cute.

So there the two of us were, sitting facing each other, nude mirror images. We kissed a bit more, to bridge the gap in between us, and then Simon leaned back. His cock suddenly seemed much more imposing. This was it. Time to put up or shut up.

I leaned over, bending myself almost in half. The cock loomed before me, and I felt the same wave of uncertainty that had stopped me before. But this time I fought through it. I felt I had to. I gently kissed the head. I didn't burst into flames. In fact, it kind of excited me. So I nervously parted my lips and took Simon's soft cock into my mouth.

My first response was to try and bite down on it, but thankfully I restrained myself from eating my friend's penis. Instead I just held his cock in the warmth of my mouth for a moment. It was a strange texture on my tongue, to say nothing of its warmth and the gentle throb of life.

Okay, Mike, I said to myself. Focus. What do you like in a blowjob?

I slid my tongue along the head of Simon's cock and began bobbing up and down on the shaft. It was an awkward moment, and the first time I shifted forward I accidentally took the whole thing in my mouth. It hit the back of my throat and I almost puked.

Simon petted me on the head. "Shhh. Take it slow. And watch your teeth a bit."

I did my best. I pulled my lips around my teeth and began slowly shifting up and down. My drool ran down to Simon's balls, and I was amazed that there was so much saliva in my mouth. Gradually I felt the half-erect dick in my mouth begin to stiffen and lengthen. Simon let out a shuddering moan. He was getting hard for me. I was making Simon feel good.

This sent an unexpected spark of pleasure to my brain, and I began eagerly bobbing up and down, trying to elicit more groans from Simon. There wasn't very much technique in my work – just the best suction I could manage. The sensation of cock in my mouth was no longer quiet so alien, and was even becoming enjoyable. I suddenly wanted to get more cock in my mouth. I was even starting to appreciate the taste.

"Ah shit," said Simon as he buried his hands in my hair. To my surprise, he pulled my head off of his cock. I looked up at him, surprised at my feeling of disappointment.

"If you keep doing that," said Simon in between pants. "I won't be able to give you a proper fucking."

I pursed my lips. "And here I thought I was going to be fucking you."

There was a cruel twinkle in Simon's eye. "I think in order to know how to top you have to bottom first. You know, just to be aware how it feels, and how far you can go."

"So you're saying this is for my own education?"

"Something like that."

"And you wouldn't just be saying all of this to get in my ass?"

"Scout's honour. Now lie back and let me get you warmed up."

I lay down on the bed, getting nice and comfortable, as Simon rummaged around in his nightstand. His erect cock hang tantalizingly close to my head. I couldn't help but reach out and give it a good stroke. "Be patient," Simon said as he pulled out a bottle of lube.

Simon applied a generous layer of lube to the entrance of my ass, then coated his right index finger in the stuff. The liquid felt strange and cool as he rubbed it into my asshole, a not unpleasant sensation. Then Simon slid the one finger inside of me and things really got going. His finger rubbing my inner walls was like the ultimate scratching of the ultimate itch. I began to melt into the bed.

"I'm going to put another finger in now, Mike," said Simon.

I felt his middle finger joining the other one, but it quickly began to feel like one thick digit probing my insides. I groaned and unconsciously spread my legs, allowing Simon deeper access. My cock had gone down a bit from lack of attention, but the anal stimulation was making me grow hard with a new urgency.

"I'm going to put a third finger in now."

I was suddenly aware of the smallness of my anus. Even with all the lube, it felt like a tiny passageway, and certainly not big enough to take something the size of Simon's cock. The three fingers thrusting within me were nice, but they were also kind of brutal, and my groans were not entirely pleasant. My ass was getting stretched out, and I didn't know how much more it could take.

"I'm going to enter you now."

It wasn't a question, really – more of a confident statement I couldn't bear to protest. I felt Simon's cockhead at my entrance. If there had been any barriers left, taking a dick up the ass was certainly one of them. But if I was a little worried about the pain, all thoughts of sexuality and masculinity were now gone from my mind. I breathed in deep and braced myself for penetration.

Simon frowned. "You're too tense. You have to relax."

"I am relaxed."

"Well, relax harder."

That got me smiling, and distracted me a bit from what was going on. The next thing I knew I felt the thick head of Simon's cock passing through my anal rosebud. I felt a flash of pain. This wasn't going to work. This was going to tear me apart.

After the head it all slipped through pretty easily, and Simon's cock was suddenly buried to the hilt inside me. I was splayed out across his lap, asscheeks touching his thighs as he looked down at me. I bit my lip to stop from crying out from the pain. There was a large, hard, foreign object inside of me, and I didn't like it. I wondered if this was how women felt during sex with men, and if so why they ever put up with it.

"Are you okay?" he said.

I decided to fight through the pain. I didn't want to ruin this, after how far we had come. "Keep going."

Simon was shifting inside me. The thought of someone being inside me, of his cock being in my ass, sort of blew my mind. At first the feeling of his cock's skin rubbing up against my insides was painful, but gradually that started to fade away. Simon was moving back and forth inside me very slowly, penetrating me with short, soft thrusts. It was actually beginning to feel pretty good.

Once Simon saw that I was no longer in pain he began to fuck me a little harder. He pulled halfway out of my ass and slid forcefully inside. That jarred my entire body, and it jarred me again when he repeated the motion. I found myself shaking along with my thrusts. I was no longer in control of my body – it had been invaded.

And that was the revelation of penetration – Simon wasn't just fucking my ass, he was fucking all of me. And all of me was rocking back and forth on his dick in response to his thrusts. And the bolts of pleasure that hit me coursed through my entire body.

"Oh god," I moaned. Simon just grinned.

Simon pulled me further onto his cock, laying my lower back across his knees and putting me at an angle where he could penetrate me even more deeply. I found myself beginning to move with the rhythm and push back onto his hard shaft. Simon just held on and fucked me harder. I could feel his nails digging into my back. I ran a hand over his chest and could feel his chest shivering. Maybe this meant as much for him as it did for me.

But in a few minutes meaning was forgotten. Simon was vigorously thrusting in and out of me. Sweat dripped off his skin and fell down onto my stomach. I was overcome with sensation. It felt as though he was some raw driving force tearing me apart, but in a beautiful way. I felt like he was fucking not my ass but the very core of my being.

"Oh god... Simon..." I panted.

He leaned down and gave me a sloppy kiss as we fucked. My hard cock pressed in between our bodies. Simon grinned as though he had just became aware of that organ, and then grabbed it and began stroking it quickly. It was too much sensation. I clawed the sheets and thought I might go mad.

A blinding white light overcame me. That was it. I was melting. Dimly I saw my cum shooting out of my cock, and felt the hot spurts land on my stomach, but I was in another world.

My skin was still tingling when, a few minutes later, Simon thrust into me with one final grunt. I could feel him spasming in me and imagined his cum shooting deep into my bowels. How was he so deep inside of me? How had I been opened up to this incredible degree?

Our bodies were both sticky and frankly a little gross, but I had no qualms about quietly cuddling with him afterwards. His body still felt a little hard and bony, but no more so than Julia's. We gave each other little kisses and waited for our hearts to slow down a bit. It was the same tranquility as I always felt after sex.

"Wow," I said.

"I agree," said Simon.

I ran my hand along his shoulderblades. "I... I think I'm gonna do that again. I don't care what that makes me."

"Not right now."

"Why not? You not up for the task?"

"No, because you're already going to have trouble sitting down tomorrow."

It was true – my ass was starting to feel less blissed out and more sore. But I could tolerate it. Even the pain felt like a badge of pride.

The next day didn't go so bad either. When I went to the store in the morning, I smiled at a private joke. Alexis gave me a weird look, but that day she didn't question my right to be there. I didn't either.