Losing My Anal Cherry

Mike and I had a very special relationship. In our senior year in highschool he and his then-girlfriend had invited me to a threesome which had developed into a more or less regular fucking session.

After that relationship had been over Mike and I, ever horny, but without any female partners to blow off some steam, had taken to whacking off together to the sweet memories of our threesome sex and porn.

We had then progressed to mutual handjobs and finally to blowing each other and swallowing each other's loads. It was a great way to release sexual tension and I guess we were both more than just a little bi-curious. On top of that, we had known each other since first grade and shared a deep friendship which made our sexual escapades a very safe thing to do, since we knew we could trust each other not to tell anyone about it.

While I went to college, Mike started working for a bank and had to move to another town. We didn't get to see each other too often, but whenever we were both home to visit our friends and parents we would try to meet up to chat, exchange stories about girls we had met and, of course, to have sex.

The one thing we hadn't done was to have anal sex. We had never really talked about it and we had always been happy with sucking each other off or rubbing our cocks together or giving each other handjobs. When I surfed the internet in the privacy of my room, however, I was busy checking out all kinds of porn on the web and I kept checking out gay sites to watch guys getting fucked up the butt. I was immensely turned on by the sight of a fat cock being shoved into a willing hole and what made me most horny were bareback scenes in which the top pumped his seed right into the other guy's asshole.

So, naturally, I started to think about how it would feel to have my ass fucked, too. I ordered a nice-sized dildo and some lube online and started practicing. At first it was painful and I couldn't even get the thing into me completely. After a while I managed that, but I still couldn't figure out what the big idea was. I mean, I was really turned on by the whole situation and I usually came when I worked the dildo into my ass, but I wasn't actually feeling anything special.

That all changed when on one occasion I shoved the dildo into my ass as far as it would go and I discovered my sweet spot inside my ass. I had found my prostate! Suddenly I realized why the guys in the amateur porn I liked to watch were having such a good time while getting fucked.

I immediately ordered a larger, longer dildo and a vibrator of a similar size and I started fucking myself with those two almost daily. I was single at the time, so I figured I might as well have some fun on my own.

After a while I added a buttplug to my collection which I even wore underneath my clothes a couple of times.

I was a few weeks after I had started ordered my new love toys that Mike announced his visit for the next weekend. He had a few days of vacation and asked if he could crash at my place since he had had an argument with his parents.

In the week before Mike's arrival I kept my hands off my dick, like we always did, since we both wanted to work up nice loads. I fucked myself with my toys every night, though, because I wanted to be nice and loose for Mike. I had decided to introduce him to anal fucking and since he had quite a large tool I thought that I should be prepared for it. I knew that he would be into it, since he, as I, was perpetually horny and even though our oral sexcapades were very satisfying to both of us, I expected him to like the idea of fucking a tight hole even more.

When my door-bell finally rang I all but ran to the door and opened it. Mike was standing outside with a big grin on his face: "Frankyboy! How's my favorite cocksucker?"

I waved him in, making sure that none of the neighbours had heard his remark. I closed the door and when I turned around he already had his pant around his ankles and his massive erection was in his hand. His glans was purple and glistening and I quickly went down on my knees and engulfed it with my lips.

I have to explain that normally I was the more dominant of us two, but when it came to sex I developed a submissive streak and I loved getting down on my knees for him.

"Oooaahh, yes!" he exclaimed, "God, yes, that's just what I needed! Man, my nuts are so full of jizz I'll fucking drown you in it today!"

While I was busy gobbling down his schlong, my mind kept racing: Did I want his cum in my mouth? Did I want his first, huge load in my ass? Would he really react like I had imagined?

I let his cock slip from my mouth and said: "Let's go to the bedroom!"

On the way we undressed, so that my hallway was strewn with discarded clothes. "Frank, I can't tell you how horny I am today. I could hardly concentrate on driving, I was constantly fondling my dick, thinking how I would stuff that thing down your throat in some time. Man, I almost totalled the car twice."

I looked at Mike's discarded unterpants and sure enough, there was a sizable wet stain in the fron that told me he hadn't exaggerated.

"Get on the bed," I told him, "I've got a special treat for you today. But keep your eyes closed, it's a surpise!"

He looked at me with a questioning look, but when I gave his hard cock a squeeze he sat down on the bed, leaning on the headboard, all the while stroking his cock. When he had sat down I reached under my bed and picked up my biggest dildo, which, just like my asshole, I had lubed up before. His eyes widened. "What the fuck ...," he started to say, but then I turned around and with a smooth motion shoved the plastic cock into my asshole. I heard a gasp and when I turned around he was sitting there with his mouth open. He was so perplexed, he had even stopped stroking his dick, but after the first shock he started fisting his cock again, faster than before.

"Do you have any idea how hot that looks?" he asked, "when did you learn that trick?"

I told him about my journey into anal sex, all the while pushing my dildo in and out of my hole. I got on the bed and lay on my back, my legs sticking into the air, to give him a great view of me fucking myself. He got on his knees and watched me, whacking off. After a while he asked:

"Can I, erm, can I have a go? I mean, can I stick the dildo into you?"

I eagerly agreed and while Mike tentatively fucked me I stroked my own erection, which had produced a nice amount of precum at that time. Mike leaned forward and pushed my hand away with his free hand. Then he took my cock into his mouth and I almost came into his mouth right then. It took almost superhuman control not to blow, but I wanted this to last a while longer.

I pushed his head back a little so he would stop blowing and asked him in my most sultry voice: "Do you want to replace this with your cock?"

Mike hesitated, but I was prepared. "Don't worry, I'm squeaky clean. I even had an enema before you came here. Here, let me show you."

With these words I took the dildo from his hands and slowly pulled it out of me. It was longer but not as thick as Mike's cock and it glistened wetly when I lay it in the bed next to me. "See? Clean as a whistle. So, are you up for it?"

Wordlessly Mike scooched closer and lined his cock up with my pucker. I gave him the lube and he spread a generous dollop on his dick. When he was done he pushed his cock slowly past my sphincter. Since I was already pretty stretched out from before his thick cock only gave me a pleasurable tingling when it slid into me, but when he bottomed out I felt the tip of his penis touch my prostate in the most pleasant way and I moaned.

Immediately Mike stopped and asked "Am I hurting you?"

I told him not to worry and that I hadn't felt that good in a long time. I also told him to fuck me like the male whore that I was (we both enjoyed dirty talk) and that I wanted his cum inside me and that was really all he needed. After some initial tentative strokes he soon found a nice rhythm and fucked me nicely. I could feel my sphincter being pulled out and pushed in and his dickhead tapdance nicely on my sweet spot so that I was slowly, but surely nearing an orgasm that I knew would be fantastic.

I could sense that Mike was also getting close because his breathing was growing more ragged and he pushed into me harder and faster.

My legs were lying on his shoulders and my dick was pointing at my face when Mike gave one final push and started coming into me. I swear to God that I felt his big dick hosing my insides with his seed, it felt nice and warm and gooey and, above all, incredibly horny and this feeling pushed me over the edge and without touching my dick once I came. I squirted copious amounts of sperm on my face and into my mouth and I swallowed as much as I could.

We lay like this for some time until my legs started falling asleep, so we disentangled and Mike pulled his cock out of my asshole.

"Holy shit" he exclaimed when he saw his seed trickling from me. "Man, it looks like I shot a gallon of my cum into you!"

I quickly reached down and caught some of he cum in my hand and then took my hand in my mouth, licking off the cum. "Yumm! Your next cumshot has to go into my mouth, Mike!"

He stared at me and then he dove for my cock to suck it clean. Then he scooped up what cum he could find on my face and my chest and ate that, too. And then we got into a 69 and sucked each other until we both came down each other's throats. After that we simply fell asleep like that.

In that night we fucked twice more and once again the next morning under the shower. Since then we have fucked many times and we have even started using a double-headed dildo from time to time. But that's a different story.

I hope you enjoyed this story. Please let me know what you think about it. You can also leave me suggestions and wishes for other stories.

pescaderoblue