One day while I was whacking off (it was pretty much a daily thing at that time, and I always shot a full load, much to my own surprise) and playing with the vibrator against my cock, I decided to change it up a bit.  I started sucking on the vibrator, pretending it was Brady’s dick.  Then, without even thinking twice, I bent over and stuck it in my ass.

A slight pain rang through my rear end as the pointed head of the vibrator slid into my rectum.  I closed my eyes for a minute and let the pain pass.  Meanwhile, my cock was dripping with fluid; I knew I hadn’t come yet, so it wasn’t jizz. I found out later that, when an object is inserted into a man’s ass and it hits the prostate, it will push the fluid out. This turned me on even more and I cupped my hand to my dickhead, catching the fluid in my palm and then spreading it over my swollen dick.  At the same time I was clenching my ass muscles, slowly moving the vibrator in and out just a bit.  Then, I turned it on.

The vibrations rattled deep into my bowels, the tip of the vibrator buzzing against my prostate glad.  Hot seminal fluid continued to bubble out of my prick as I rubbed it up and down, a huge orgasm making its way into my groin.  My toes curled, my anal passages clamed down on the vibrator and my hips jerked up as an overwhelming wave of pleasure hit me.  My throbbing cockhead spewed come, sending it several feet away from me as the orgasm took hold of me, bringing me to my knees, still jerking away at my stiff shaft.

After what seemed like hours, but in reality was only a few minutes, I came back into reality.  My once rock-hard cock was now rapidly shrinking in my hand, my fingers drenched in semen.  The vibrator, still running, was slipping out of my ass.  Hardly able to keep myself up, I collapsed to the floor, the plastic toy dropping to the ground next to me.  After a few minutes, I was able to get up, albeit only getting to my knees. I looked down at the vibrator buzzing on the ground.  I couldn’t believe that tiny barrel had brought me to so much pleasure so quickly.  I got up, took the vibrator to the bathroom and cleaned it up, wiping myself down with a towel.  Just as I was putting the vibrator back in the drawer where I found it, I heard a vehicle pull into the driveway. Shit, my parents were home.  I ran to the bathroom and jumped into the shower, hoping like crazy that I hadn’t missed any come spots.

All throughout the rest of the day and into the next week, I couldn’t get that masturbation session out of my head.  My penis got stiff the second the thought entered my head.  My train of thought started to twist the situation, and soon I saw myself standing in front of Brady, his hard cock in my ass, pounding me without mercy.  I almost came in my pants at that thought.  I decided I had to try it.

Brady had been out of town for a few days, hence the vibrator session.  The next day when he called, I jumped at the chance to come over.  Not five minutes later, I was at his front door.  He opened it and smiled when he saw me.  After coming in, we grabbed a few cans of soda from the fridge and ducked into his room, where his PlayStation was in full swing.  We sat at the console for about an hour or so until we knew we were alone (both of his parents worked in the next town and it wasn’t hard to get rid of his little brother) I paused the game and proceeded to tell him about the experience I had with the vibrator.  Every now and then I would glance at his crotch while I was talking and I could tell he was getting turned on by what I was telling him; his cock was swelling up in the front of his shorts.  He caught me looking and without a word pulled out his shaft and started jerking on it. 

Just as I finished describing my rendezvous with the toy, I leaned over and took him hungrily into my mouth.  I bobbed up and down about six times and felt his cock stiffen; he then proceeded to empty his seed into my awaiting throat.  I continued to suck on his rapidly deflating dick as he reached down to unbuckle my pants.  I reached down and grabbed his hand, pulling it away from my crotch.  “Not yet. I have big plans for this, and I don’t want to waste anything.” I said with a smile.  “Then what the hell? You just got me off, it’s your turn now.” he said, his eyes locked on my pants zipper.

“Brady, I want your dick in my ass.” I said, expecting him to start shouting at me that I was a fag and to get out, or to back away from me.  Instead, he asked “Are you sure? That’s a big step.  Besides, I don’t have any condoms and I’m not going in there without one, no offence.”  His response surprised me, but it was what I was hoping for.

“None taken. And I wouldn’t have it any other way. Even though we both don’t have any STDs, I’ve been researching this and there is a lot of stuff that could happen if you weren’t covered up.” I replied, grabbing his shorts and throwing them in his face.  “Besides, I hope you would think more of me than that. I wouldn’t ask for it if I wasn’t ready.  Let me take care of everything.”  And with that, I walked out of his room to take a piss.

 We hung out for the rest of the day, not mentioning anything about we had discussed, just shooting the bull, until I had to get back home for dinner. Throughout the meal, I kept expecting my parents or sister to ask what was wrong. I felt as though I had my plans written on my forehead in black permanent marker.  Why couldn’t they see the facts were as plan as the nose on my face? I then realized that, unless they were mind readers, they had no idea what was going on. I decided to keep it that way.

I helped clear the table then told my parents that Brady had asked me to come over to watch a movie and asked if that was OK with them.  They said it was and I almost ran to my bedroom, telling them I was grabbing a jacket.  I snuck over to the far side of my bed and from underneath, pulled out a small cardboard box that had a music box in it.  I pulled the music box out to reveal a false bottom that I had made; underneath that was a tube of KY jelly and a box of condoms.  I was curious at that time of my life and wanted to know how they felt on me.  I had put them on with some difficulty (they were tight, even for a teenager) whacked off in them until I had come (which didn’t take long).

I grabbed the tube of lube and two condoms and stuck them in my jacket pocket, put the box back together and back under my bed, then headed out the door.  In no time at all I was back at Brady’s where they were indeed watching a movie. Brady put on his jacket and we headed out the door to the park down the street.  Once at the park, we messed around for awhile, throwing a football back and forth until the other people in the park had left.  We then headed to the bathrooms, went in and blocked the door shut.

It was dark and smelled like old piss.  It wasn’t exactly the perfect place but hey, you can’t choose everything.  I took the condoms and lube out of my pocket and told Brady to take his pants off.  He obliged, dropping them to his knees as I did the same.  We reached for each other’s cocks as we came together and, for the first time, we tongue kissed.

I broke away and ripped one of the condom wrappers open, pulling it out and holding it to my nose.  “I love the smell of these things.” I told Brady, walking over to him and dropping to my knees. I blew him for a minute until he was good and hard then installed the beige condom over his manhood.  I stood up, turned around and bent over, opening the tube of KY and squeezing a good sized amount onto my fingers which I then slathered over and into my asshole, then put a bit on the tip of Brady’s cock for good measure.

“Fuck me.” I said, guiding his prick towards my trembling virgin ass.  Very quickly I found the head of his dick against the entryway of my bowels; at that point I decided that there was no turning back now.  I told him to be careful, that when he first goes in it hurts like hell. 

Brady put his hands on my ass, pulling the cheeks apart and slowly leaned in, the tip of his manly sword piercing the previously virgin swirl of tissue and muscle that was my sphincter.  He slid the head of his cock into me slowly, then stopped.

“You OK?” He asked. I could hear the concern in his voice. I realized at that point that I had tensed the muscles in my ass, squeezing down on him and that I was holding my breath at the same time.  I had thought that I would feel the same pain that I had endured with the vibrator, but to my surprise and pleasure, I felt nothing other than the heat from the hot poker that was making its way into my body.

“I’m OK. Let me do the rest.” I breathed, and slowly leaned back, taking more of his rigid shaft into my ass until I felt the tickle of his pubic hair against my ass crack and the soft skin of his balls against my own.  “OK, now just give me a minute.” I said to him, willing my body to accept this foreign entity without resistance.  Slowly, the muscles of my anus relaxed and he slipped in just a fraction of an inch more. When that happened, I felt the now familiar jolt of my prostate being probed. He had hit the male G-spot and I was loving it.

“Holy shit, this feels amazing. This is tighter than pussy.” Brady said as he slowly began to withdraw from me, pulling out until half of the head of his dick was still inside me.  I waited for the smell of shit to hit my nose but nothing came.  Brady then slid his hard-on back in, again hitting the sweet spot.  I leaned forward a bit more and grabbed my ankle with one hand, my own throbbing dick with the other.  This was better than anything I had ever experienced.  I had wondered for some time how either a woman or man could stand to have a dick in the ass; now I knew.  But this was way better than I could have thought.  I started moaning as Brady continued to molest me, quickening the pace of his slick and throbbing cock in and out of my hole.

“Wow, dude, this is the longest you’ve lasted.  You getting enough?” I asked.  In response, he reached around and grabbed my hard member, jerking it in rhythm to the pounding my ass was receiving.  “It’s the condom.” he said.  I bore down for a second, opening my anal passage then quickly tensed everything back up, squeezing his dick with all my might.

“Oh, god, you do that again and I’m going to lose it.” Brady huffed, the in-and-out movement of his dick now reaching a fever pitch.  The sound of his balls and thighs smacking my balls and ass was bouncing off the walls back to us, heightening the experience even more.  “That feels good. C’mon Brady, shoot your load. Come in my ass.” I hissed through clenched teeth as I tightened my ass down on his dick again and again, every time his forward thrust propelling his cock head into the folds of my rectum and massaging my prostate.  A continuous stream of white liquid was pouring from my cock as Brady stroked my shaft, bringing me closer and closer to orgasm.

“Oh, god. I’m going to come. I’m gonna come, I-I-I-IIIIII'MMMMMMMMM COMMMMMMMMIIINNNGGGGGGG!!!!!!” Brady shrieked as my asshole clamped down on his hot cock and stayed that way as my own orgasm rocked me back onto him.  I felt the condom balloon in my ass as Brady’s sex tool spewed his semen up from his balls and out of his body.  Deep in the throes of his own pleasure, he squeezed my cock with all his might like you would squeeze an orange to juice it.  He arched his back, his pelvis driving into my back and bending my upper body backward onto his, my own jizz shooting out of the end of my dick like a fire hose.  I was standing a good 5 feet from the wall of the bathroom and as I closed my eyes, lost in the pleasure, I saw my hot spunk hit the wall with such force that it looked like a huge spitball.

Brady was right there behind me, still locked in his orgasm, the heat from his body radiating all around him as the furious pace of his hips started to slow.  I could feel in my ass that the condom was moving back farther and farther onto his dick, which meant that it had been filled with his come.  I continued to shoot my load against the wall, each stream of white fluid not quite reaching the place where the last one had landed.   I was too wrapped up in the moment to care who heard us or what might happen next. The feeling of euphoria was amazing

After what seemed like ages, Brady slowed his pumping to nothing but small movements back and forth. I dropped to my knees, feeling the disappointing sensation of his dick popping out of my ass.  I was still squirting come but was no longer having an orgasm, and I think Brady was going through the same thing, as I could hear him panting behind me.

“Oh man, I just—couldn’t stop.” Brady said between gasps for air.  I could tell he was completely spent

I looked into his eyes and said “Now that’s how you fuck someone.  That was way better than anything I could have ever imagined. I enjoyed the hell out of that."

Brady, still breathing hard, looked back at me and said “Wow man, where did you learn to do that?”  I replied with a smile “From watching porn but mostly from just listening to you and reading how you were fucking me. Brady, you fucked my ass. You took my anal virginity.  And it was great!! How was it for you?”  “You were a very tight fuck, you little whore. It was the best I’ve ever had.”  he replied, grinning from ear to ear.  I got up, barely, grabbed a roll of toilet paper from the spool and started cleaning myself up. “I’m too spent but you are next, bitch.” I said slyly, wiping the rest of the white fluid from my now empty balls and dick.

Unfortunately, that would never happen.  Brady didn’t like the thought of the lube on him and I had to be content with sticking my finger up his ass only once. I let him fuck me in the ass one more time later in the year, but it was winter and we were again outside; he was barely able to get half of his dick head into me.  It was so cold I just couldn't get my muscles to relax at all.  He moved back East with his family not too long after that last encounter, and that's the last I have heard from him.  But the events of that summer will stay with me for the rest of my life.

Although I am now 11 years older and married to a great woman who lets me do anything sexually (except for anal, damn it!) I think about that day a lot.  I’ve experimented anally with numerous objects, including several dildos and vibrators and even a bed post, but nothing even comes close to the feelings I had that day when Brady popped my anal cherry.  I have tried to locate him but have not been able to find any hint of him anywhere.  I guess I still have the memories.  Oh, and as far as my sexuality, I think I might be bi, but I still lean more towards gals then guys; I can’t stand the thought of kissing another guy but I don’t mind a dick in the butt. Figure that out!!!!