NOTE: This is a continuation of my story "Fun With Fred: PART 1' so read Part 1 first if you have not before reading this Part 2. The names of the characters involved have been altered for privacy.
IF YOU DO NOT LIKE STORIES ABOUT TWO BOYS HAVING SEX THEN DO NOT READ ON AND KEEP YOUR NEGATIVE COMMENTS TO YOURSELF DAMNIT!
By now the two of us were exhausted so we both collapsed onto the bed. Fred curled up next to me, put his arm lovingly around my chest and whispered into my ear: “Time for me to do you now.”
Those words were enough to cause my flaccid penis to stand up at full attention again. Fred laid me flat on my back and placed himself on top of me with each of his legs on either side of mine. With his shaft on top of mine and my scrotum pressed against his, we rubbed our genitals together; his hands on my shoulders and mine half on his thighs and half on his buttocks. Fred shifted his whole body further up mine, dragging his cock and balls from my groin to my chest as he did so. His legs were now on either side of my torso. He moved his penis towards my mouth. I felt his warm swollen head rest against my lips in request for me to suck him. I gladly obliged. I took most of his cock into my mouth and got my tongue to work on it like it was a lollipop. Fred gasped pleasurably when he entered my mouth and continued to moan softly and caress my hair gently as I sucked him hard. The texture of his warm flesh felt smooth on my tongue. I enjoyed particularly feeling his penis slit which seemed to give him more pleasure than anywhere else I used my tongue on. While I was orally pleasuring Fred’s dick I gently massaged his buttocks with my hands and occasionally slipped a finger inside of his anus which intensified the pleasure for him. After a while of tongue and anal teasing I decided to give it all to him now. I slipped two fingers of my one hand into his ass and finger-fucked him, caressed his balls with my other hand while I used my tongue to relentlessly lick his cock. The movements from my anal finger-fucking also caused Fred to move his penis back and forth in my mouth. Fred seemed to be in his element; his head was cocked back, his eyes were closed and he was moaning: “Ah! Ah!” each time he moved he penis into my throat or when I rammed my fingers against his prostate. Fred had stopped caressing my hair now and was rubbing his chest with both his hands causing his nipples to stand up erect. His moans now became more frequent and louder.
“I’m…ah…close,” was all he could manage.
I could feel Fred’s balls scrunch up close to his body in my one hand, feel his anal sphincter contracting around my fingers and it seemed that his penis even grew a little bit harder and longer.
“I’m…ah…AH!” Fred’s warning failed, but I knew what was coming. I quickly rammed my fingers as deep into his ass as I could which pushed him over the edge. His cock began to spasm uncontrollably in my mouth; it was a wonder that it stayed in. His ass tightened around my fingers so; I thought they were going to be crushed. His balls drew very close to his body; even to this day I have never felt anyone’s balls draw so near to their body than Fred’s were doing now. I tasted a new taste in my mouth. It was salty yet sweet. I recognized it as Fred’s cum. He shot just two small loads down my throat and he was spent. His body had only recently begun to produce sperm and Fred was in the habit of masturbating frequently. Finally, I felt his ass muscles relax around my fingers, his balls drop down very low and his penis soften and shrink. Fred removed his dick from my mouth, climbed off me and flopped down onto his back tired. I was also tired because I had to breathe through my nose the whole time Fred’s cock was in my mouth which I’m (obviously) not used to.
Fred looked over at me and smiled.
“That was way better than my hand will ever be dude!” Fred came close to me, gently kissed me on the cheek and assumed his position on his back on the futon. Fred’s penis was still flaccid and had shrunken to such a minute size that his cock looked like a button pasted above his low hanging balls. I wanted to change that. I wanted to feel how it felt to have him up my ass. I was curious.
I rolled over closer to Fred and placed my hand on his groin and fiddled with his tiny dick. In its flaccid state it was even smaller than my pinky finger and wrinkled, but I found it fun to play with all the same.
“You just can’t get enough can you!” said Fred, but I silenced him with a kiss.
Fred’s little soldier began to stir and soon I had my hand wrapped around his semi-erect shaft pumping it up and down. Now that he was fully erect I broke the kiss and got down into a doggy style position.
“Put your dick in me!” I ordered.
Fred just smiled and said: “Of course! Just remember its sore at first.”
“Quit talking, man! Just put your dick into my fricking ass!” I demanded. I didn’t want to think about Fred crying at the pain he felt when I put my cock in him.
Fred came up behind me and put his cock head in between my ass cheeks and moved it down until he felt where my butt hole was. I squeezed my butt hole like Fred had done to help me get in him. Fred’s cock pressed against my hole until I felt a little bit of him in me. I took it with a gasp and a wince of pain. “You cool?” asked Fred.
“Yeah, give it all to me!” I replied.
Looking back that was the stupidest thing I’ve ever said and I truly wish that we had known about using lubrication on our anal sphincter and penis before engaging in anal intercourse. Fred took the invitation, placed both his hands on my waist for support and shoved as much of him in me as he could. The pain was excruciating. It was the worst pain I’ve ever felt before. I could feel tears prick in my eyes, but I was determined not to cry. I tried not to cry out in pain with all my might, but the shout escaped my lips regardless. I instinctively tightly wrapped my hand around my cock and pumped it at a record breaking pace hoping it would ease the pain somehow.
“Ah crap!” I heard Fred exclaim and started kissing and rubbing my back as if he hoped to have the same effect as me pumping my cock.
After what felt like an eternity of pain, I finally felt the pain subside. It was a strange yet wonderful feeling to have Fred’s penis in my ass; a place of my body where I had never explored myself.
“Okay, Fred. The pain is gone. Start pumping,” I said. “Just do it gently at first.”
I could feel Fred’s rock hard penis slowly moving back and forth, back and forth in my anus against my prostate. It was a bizarre sensation. It didn’t feel sore, but it didn’t feel pleasurable either; it was a somewhat neutral sensation – but that’s when Fred began to pick up the pace. Faster and faster, harder and harder, gradually, gradually he went.
The neutral sensation began to shape into something different, something good. It was pleasurable for me with a little bit of pain in the mix just to add that bit of excitement, danger, thrill. But it was a different sort of pleasure, not the type that I got from exercising my penis. No, this was more of an indirect stimulation. I could too tell that it was pleasurable for Fred by his erratic breathing pattern and occasional moaning. My body was tense and I was sweating. By now I had removed my hand from my erect and throbbing penis and used both my hands for support. I could feel Fred’s body generating a lot of heat behind me so I guessed that he was sweating too. It was very late and my eyes were heavy with sleep. The only thing that kept me awake was Fred’s penis pounding in and out of me. I was so tired, so lost in the pleasure of having anal intercourse I didn’t realize how hard Fred was banging into me or how loudly he was moaning or even how loudly I was moaning for that matter. I could tell that he was trying to find words to communicate to me that he was cumming, but words seemed to fail him – all that he could utter were moans: moans of pleasure. I knew what was coming. I was prepared. I could feel Fred’s penis spasm as he achieved orgasm as well as a trickle of warm liquid running down my anal canal. It was as if his orgasm had somehow transferred into me too as I felt my pubococcygeus muscles contract resulting in a trickle of semen running from my penis head, down my shaft and scrotum and drip onto the floor. Fred then pulled his penis from my ass (which was a great feeling in itself for me as I felt my anal sphincter shrink back to size after being stretched around his girth) and curled up on the futon under the duvet. I joined him and soon fell into a deep sleep after exchanging a few tired words of how great our sexual experience was.
The next day we awoke, still naked. We dressed in silence. Fred seemed awkward to be naked around me and avoided eye contact which struck me as odd considering the events that took place a few hours before. I knew that what happened between Fred and I would remain secret and would never happen again. My fun with Fred was over.