During lunch break, I met Mike behind the bleachers, something we did rarely. When we did, we shared a cigarette he had filched from Mr. Mitty’s desk. Our illustrious, but demon-plagued history teacher managed to smoke his way through two packs of Chesterfields per day, and the odor followed him like a cloud. Mike drew a puff, inhaling briefly, then blew it out above his head. He passed it to me.

“You on for Friday?” He was referring to our sleepover.

“Yeah, man,” I replied, taking a short drag, flicking the ash, and giving it back to him. Then I addressed what had been haunting my brain since the previous evening. “Mike, you fool around with your mom? That’s hot!”

He blew another cloud of smoke, looking all nonchalant.

“Did it fuck with your mind?”

"It shocked the hell out of me, but I'm okay." I was very near him but refrained from touching his body. God forbid anyone sees us. "Watching you fuck her was awesome!"

He passed the cigarette back to me.

“Yeah.” He looked at the football field beyond the stands, scanning back and forth, then glancing over his shoulder in case we were being observed. “We’ve been doing it for a few months after she caught me spying on her and her last boyfriend.”

“Oh, shit. Did she freak out on you?” I took one more drag, then dropped the cigarette to the dirt, grinding it underneath the rubber tip of my sneaker.

“Fuck, yeah.” He turned to look at me. “I thought I was done for, but she slept on it and had a whole different attitude the next day.”

“Damn.” My eyes were wide. “That’s how you know about stuff.” I prodded him on the shoulder. “You’ve been holding out on me.”

“Sorry.” Mike looked down at his feet, then back up at me. “I wasn’t sure how you’d handle it, but you and I have been so hot and heavy the past week, I just had to.”

“I’m glad you did.” I so wanted to caress his skin, but refrained. “Won’t my coming over for the weekend interrupt things?”

Mike paused for a moment as if searching for the right answer.

“No, I think we can work it out.” His hand casually slipped under my shirt, touching the small of my back, making me jump. Gazing into his eyes and feeling his caress made a lump in my throat.

“You up for some fun?”

"Of course," I replied. He kept staring at me. Something in his eyes told me I didn't understand. Then it dawned on me.

“What the fuck are you talking about?” My mouth was open. Could I be hearing him right?

“Well, if you can keep your shit together and keep a secret…”

I couldn’t believe what I was hearing. “Your mom would fool around with me?”

“Man, if you’re not into that, I’m cool with it.” Mike’s hands were trembling, but he still tried to appear calm. “No harm, no foul.” 

I had to think about it for a moment. Holy shit, this was really happening!

“I just can’t let my mom, or anyone, find out!” I said. As I spoke, Mike started rubbing the small of my back, arousing me even more.

“We’ve been able to keep this under wraps for a long time,” Mike replied. “You just need to act like nothing’s happening.”

“Okay.”

“However.” Mike’s hand flattened against my back and he pulled me toward him. “Don’t come in expecting it and let me take the lead.” I could feel his breath on my face, he was so close. “You know how women can be.”

Getting it on with Mom, I was starting to get the idea. I nodded.

The bell sounded in the distance, signaling the end of our lunch period. Mike pulled his hand away. “Damn, I want to suck your cock right now,” he whispered in my ear, forcing a shiver throughout my body. He brushed a few stray cigarette ashes from his shirt. “Can you drop by after school?”

“Yep.”

“Good. I’ll see you then, lover.”

“Okay, boyfriend.” I smiled, arching my eyebrow, looking at him askance. He smiled back.

“Jesus, give me a break,” he whispered before trotting away.

My cock was so hard, I fought to keep from unzipping my jeans and relieving myself all over the grass. It took an hour of sitting and staring at Mr. Mitty’s wrinkled, nicotine-worn face for my boner to subside.

During my free period that afternoon, I went to the school library and searched for any information on breastfeeding and lactation. Sadly, there was none. The only thing I found was a tattered handbook for young women, warning them about the dangers of dating, which of course led to heavy petting, or worse. The final few pages dealt with the tragedy of teen motherhood. I’d have to go to a grown-up library to continue my search.

My cock was again hard by the time I got to Mike’s late that afternoon. Parking my red Schwinn behind the house, I entered through the unlocked back door, stepping into the kitchen to meet a naked Mike. His cock looked as hard as mine felt, straining in my jeans.

Immediately, we started kissing, our arms encircling one another as our mouths lapped together.  He pressed me against the kitchen counter as I gripped his tensing buttocks.

“I want your cock in my mouth,” he finally whispered against my neck.

“Let’s get to it,” I replied. 

Mike took my hand and led me to his bedroom.

I shed my clothes and we started our new routine, slipping up on the bed, luxuriating in our naked flesh touching and rubbing. Of course, nipples were fair game. We kissed and humped against each other, sucking each other’s nipples while our hard, bobbing cocks bumped and rubbed together. Mike finally released my nipple and started trailing kisses down my torso, toward my cock.

“Oh, damn, yeah,” I looked down at my best friend. “Take it in your mouth.”

Gazing up at me, he grasped my erection, giving it a squeeze, making the purple helmet swell and glisten. Mike opened wide, slowly lowering his mouth over my jutting penis. He managed to avoid contact until the tip of my cock pressed against the base of his tongue. Feeling his hot breath surrounding my sensitive tool, I squirmed, wanting more contact. He fulfilled my wish.

He didn’t choke as my cock slid down his throat. The moment he closed his mouth on it, he created a strong suction, bowing his cheeks as wet, slippery flesh surrounded me. Mike reached up to tweak my nipple as his other hand held my cock steady. With agonizing slowness, he drew his mouth up my shaft, leaving it covered with saliva. Gripping the sides of the bed, I fought to keep from bucking against his mouth.

Within moments, he was working up and down my shaft, maintaining perfect suction as he tugged on my tender nipple. Occasionally, he would stop and stare at me until I wriggled impatiently. With a snort, he’d resume blowing my cock.

As I stared at the popcorn ceiling, I thought about Mom’s blow job and compared it to Mike’s.  There were a lot of similarities, although at the time I wasn’t aware of how many ways a man’s rod could be manipulated. Still, it almost matched my mother’s handiwork. Almost.

Perhaps the idea of my own mother sucking me to completion held more erotic value than Mike swallowing my seed. Those thoughts dissipated as I felt that familiar pressure swelling up in my loins. Mike started bobbing more quickly and I concentrated solely on the pleasure he was administering.

Between Mike and my mother, I was getting used to a daily blow job, although it was nowhere near becoming mundane. I never lost my appreciation for this simple, effective act, staring down at the top of someone’s head while they pumped away. The escalating sensations made me grip the sides of the bed harder, arching my back slightly to intensify the pleasure.

“Yeah…yeah,” I hissed. “That’s it…don’t stop.”

Mike groaned, knowing he achieving the desired effect, and was about to receive my load. A slight rake of his teeth made me jump, but that was the extra friction I needed to push me over the edge. Again, I came for my best friend. Hard.

“Aaaaggghhhh…” I bucked, arching my back even more as the orgasm hit. For a delicious moment, my body hung, suspended in space, as my mind went blank. 

Backing off a bit, Mike slowed his undulations but still kept a strong suction on my cock, dutifully swallowing all of my ejaculate. As I returned to consciousness, I found my words again.  “GodDAMN, that feels so fuckin’ goood!” I praised Mike’s work as his lips smacked against my glistening, spent shaft, savoring the taste of my come, licking me clean. When done, he slid up beside me, our naked flesh again rubbing together.

We kissed some more. I tasted my come, too, as our tongues lashed together. He sucked my tongue like a little cock while pressing his erection against me. I thought about Mom’s manipulation of my anus and how I had started to crave it. Grateful for such an incredible blow job, I also wanted Mike to get his share.

“You need to fuck me,” I whispered, my lips brushing across his face. “Come for me.” Of course, I was thinking of what was becoming our usual routine, his cock pumping between my thighs.

“Oh, if I must,” he replied in a mocking tone. 

I slapped his bare skin as he rose to his knees, his cock jutting toward me aggressively. As much as I had seen and touched Mike’s lean, nude body in the past week, it still had an effect on me. I found myself salivating, my cock swelling with the thought of what he was going to do. Again, I jumped when he finally spoke.

“Get that ass up in the air,” he commanded.

“Yes, sir!”

By the time I got on my knees, gripping the headboard for leverage, my cock had returned to full mast, bobbing between my thighs, aching with need. As I felt his hands gripping my waist, I instinctively turned my ass up toward him. I was coming to the realization that I wanted his cock inside my ass, not just pumping between my legs, but deep inside. Of course, I’d take whatever I could get! I closed my eyes, waiting for the feel of his hard shaft. What happened next surprised me.

“Time for some real fucking,” Mike said. His voice had a different tone – low and authoritative.  I didn’t know what he meant until I felt it.

I couldn’t help but gasp when I felt Mike grip my buttocks, his thumbs spreading them to expose my anus. Next thing I knew, his cock was rubbing up and down my bunghole as I quelled a whimper. In seconds, I felt the tip pressing against me.

“What are you doing?” I asked, knowing the answer.

“Do you want this?” Again, his voice sounded more adult, and he was totally serious. “I’ll stop if you don’t.”

The time for kidding about anal sex was over. Yes, I did want it. I wanted his cock in my ass, and now.

“G-go ahead,” I stammered. If he wanted to do it, then I’d accommodate.

“Okay, then.”

His cock pushed against me, not aggressively, but slowly. I was grateful for his mindful touch since this was far from a natural act for me. While Mike wasn’t hung like a horse, his cock was much more than Mom’s slender finger. I relaxed as much as I could, taking deep breaths, but after several minutes of pushing and gentle undulations, he still couldn’t get inside.

“Wait a sec,” he said. Slipping off the bed, he stepped over to his nightstand, then, reaching into the top drawer, pulled out a jar. He returned to his kneeling position behind me and I heard him remove the metal lid from the glass jar. Next thing I knew, his fingers slipped inside my ass. I gasped with pleasure as he rubbed Vaseline up and down my tight hole. The next moment, I looked over my shoulder to see him coating his erection with the viscous stuff.

“Now let’s try, lover.” 

Again, gentle pushing and pressure against my anus. I closed my eyes, then it happened. I felt his cock start to enter me as he groaned with pleasure. My mind raced as he pushed into my ass, inch by inch. My brain flooded with thoughts, trying to handle the still-unnatural fullness welling up inside my body. Still, there was a tinge of pleasure, and it grew with each passing moment.

“Damn, that’s tight,” Mike said. I could feel his hot breath on my back as the bedsprings gently creaked. “A lot tighter than Mom’s.”

I wasn’t sure if he meant her pussy or her ass, but I wasn’t going to complicate matters. By then, the sensation of his cock in my ass was indescribable. It just felt damn good. He kept pushing, his fingers digging into my hips for leverage. Another minute passed and I felt his body pressing against mine, and I knew he was far inside my ass as he could go. 

“How’s that?” He asked, his voice hoarse with lust.

“Goddammit,” I panted against the bedclothes. I felt impaled by his cock, and dominated as well.  It was a delicious surrender and so very kinky and taboo. “Don’t stop.”

“Your wish is my command, master.” 

Always the smart aleck. With precision, Mike started sliding his cock in and out of my ass.

My hands, white-knuckled from gripping the headboard, braced me as our bodies started slapping together.  Mike grunted and huffed, ramping up his pounding.

“Is this okay?” He asked.

“Yeah…yeah…keep fucking,” was all I could respond with. He obeyed.   

A whole new sensual world was opening up for me. I couldn’t believe my best friend was fucking me in the ass, and it felt incredible! My jutting cock bobbed with the steady rhythm of Mike’s thrusts. The warm feeling in my groin overtook my entire body as I thought how perfect a mouth on my cock would be at that moment, or a reach around, but Mike’s hands were busy keeping my ass steady against his onslaught. For several minutes, I luxuriated in the act of being buttfucked and, yes, it was something I could definitely get used to. Gasping for air, Mike managed to speak.

“Dammit, I’m about to come! That tight ass of yours is really doing it.”

“Don’t stop,” I managed to yelp, pleasure dominating my senses. “Don’t pull out.”

“You want me to come inside you?” The slapping noise echoed off the walls.

“Do it!”

“Geezus, the things I do to keep you satisfied!” Again with the smart remarks! “You’re turning us both into fa…ahhh…AHHHGGG!!!”

The orgasm cut him off as he bucked and growled. I could feel his cock twitching, jerking as he delivered a load deep into my rectum. I held on for dear life, lost in my own sensations, as his orgasm persevered. Mike was out of control.

“I can’t stop coming…god…DAMMIT.” 

I held on for dear life as his violent thrusts continued for another minute, then slowed. My ass burned, thoroughly battered by Mike’s cock. Still, I wouldn’t have traded it for anything. I could smell his body, still pressed against mine. Drops of his sweat hit the small of my back.

“Ahhh…” Mike panted with release. “Ohhh, yeah…fuck yeah.”

“Good for you, lover?” I teased with a ragged voice, still relishing the fullness of his cock in my ass. I shivered, realizing we were physically connected, like two pieces of a jigsaw puzzle.

“Dammit, Billy,” my best friend replied. “Holy fuck!  How about you?”

“Talk about a new experience, and you know I have to return the favor.”

"Okay," Mike caught his breath but kept his cock pressed deep inside my ass. "You got a deal, brother, but maybe this weekend. We don't have any more time right now."

Mike stayed inside for a few more luscious moments, then tumbled on the bed beside me, exhausted, his sexy body covered in sweat. I clenched my anus repeatedly, savoring the lingering sensations, but also trying to get it back to normal. As strange and pleasurable as the experience had been, it was still far from the usual routine.

Gazing upon his glistening body, I couldn’t help but touch it, rubbing my hands across his torso and stomach. Our eyes met and we started kissing hungrily in the afterglow.

“Sweaty boy,” I whispered between wet kisses.

I started kissing his face, working my way down to his neck and shoulders. Of course, I had to take his nipple in my mouth, savoring the salty sweat as I suckled on his erect bud.

“Mmmm,” Mike moaned with appreciation. “We should grab a shower before Mom gets back. I have to wash your fucking sex off my dick.”

I released his nipple, slapping him on the hip. “Asshole!” Then we both realized how funny that word was at the moment and laughed.

The warm spray of water soothed me as Mike washed my ass. It was déjà vu all over again as I remembered my shower time with Mom that morning. His hands were rougher than my mother’s, but I didn’t mind. The personalized service felt great. We lathered and rinsed each other, our cocks incapable of being limp. There was still a lot of desire remaining. I’m sure we could’ve fucked the rest of the evening and into the next day, but circumstances prevented it.

As we toweled off, I pulled up the courage to talk about his mother.

“Man, how did you get your mom to produce milk like that? Can I ask?”

“Sure,” Mike replied. “I don’t mind.”

“That was so fuckin’ sexy, you sucking her tits like that.” I tossed the towel on the bed and started to get dressed.

“She did it herself with her last boyfriend.” Mike helped me dress, with the help of a few kisses, and I let him. “He got her going and when she tossed him out, I just took over.”

“Jesus, I wouldn’t know what to do if my mom was like that.” I paused a moment, realizing what was coming out of my mouth. “Forget that. Yes, I WOULD know what to do!”

Mike’s...