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Easing into Mens Anal Sex

When I first became aware that I was attracted to other guys, it didn’t immediately hit me that mens anal sex would be something that I would have to deal with.  Honestly, I have to say that it never really crossed my mind in the beginning. Sure, I started noticing hot guys and dreamed about what it would be like to hold them and kiss them, definitely doing some hardcore groping with them, but it just never seemed to go beyond that; at least in MY mind. I WAS pretty young, though, when I first realized that females just didn’t do it for me, so maybe that had something to do with it all.

The first time that I started to realize that mens anal sex is something that I would need to learn more about was on my first real date as a gay male. We were talking about some pretty personal things when the subject of sex came up. He asked me what the biggest cock I had ever had was. I wasn’t totally sure how to answer that since the most I had ever done with a guy was some heavy duty kissing and groping. It was a little embarrassing to admit, but at that point in time I had not even sucked a guy’s cock. So maybe you can see why I really didn’t understand what he was talking about.

I was embarrassed, but I also knew that I wasn’t going to be able to fake my way through this conversation so I was just honest. I admitted that I had never really gone that far with any guy. That’s when my date began to explain all about mens anal sex to me. He went into great detail about everything that happens when you get fucked up the ass. I had no idea that someday a guy was going to want to put his cock into my asshole. Of course, I would most likely get to reciprocate and that part didn’t bother me so much. But I was little frightened at the prospect of having some guy shove his hard cock all the way into my ass. I mean, there just didn’t seem to be like there was THAT much room back there.

Then my friend started to explain to me about the prostate gland and how that plays a big part in gay male sex. You simply had to have mens anal sex in order to understand why it could be so very pleasurable is basically what he was telling me. From the things he was saying, I wasn’t completely sure that I would agree with the part of it being pleasurable. However, I was more than willing to listen because it was beginning to be clear to me that this type of sex was certainly something that was going to be expected sooner or later in any gay male relationship.

I was so scared that I actually asked him if it was possible to be in a full gay male relationship without mens anal sex.  After he had finished laughing at me, he went about explaining how that could be compared to a straight couple that never had intercourse. Imagine how surprised I was to find out that I was still a virgin! It also was somewhat surprising that I was such an innocent that I never knew about this type of sex. Now, though, it was clear that I needed to learn everything there was to know about it because I certainly hoped that I would find a true partner for myself one day. If that was going to happen, apparently he would be expecting me to have  mens anal sex with him.

So I started asking questions of my friend, who was only too happy to share his information and knowledge with me. It all made sense to me but I still had a fear lurking in the back of my mind that made me wonder if I was ever going to be ready to have something long, thick and hard shoved into my ass over and over again. That became my next question. How was I supposed to prepare for the main event without enduring lots of pain before I could get to the pleasure part?

Some of my gay friends had been telling me about this website called koalaswim.com. They claimed it sold all kinds of hot designer swim suits, thongs and fetish wear. I decided that I would go have a look to see if there was anything there that may help me get myself ready to enjoy a good session of mens anal sex.

I did notice as I was browsing koalaswim.com that there were some swimsuits that I was definitely going to come back to at some point. They really were quite hot and the models that were wearing them totally got my attention. However, I had to make sure that I didn’t get distracted from my ultimate goal, which was to see if I could find some fetish wear that might slowly and painlessly get me ready for my first experience with anal sex. As it turns out, I didn’t have to look very long before I landed on an item that I found very interesting.

With the provocative  name of Ass Invasion Semi Thong, I thought it was definitely worth a closer look for practicing mens anal sex. For one thing, it was a pretty kicky yellow color but since I didn’t plan on wearing it outside of my clothes, I figured that would be just for me. At any rate, this was a very special thong. Ass Invasion gives the lucky wearer a smoking hot front pouch that covers everything it needs to but only minimally. What a tease! The important part for me, though, is that it’s a combination cock ring and butt plug. Now, I had not ever used a butt plug before – ass virgin, remember --- but I did know about them from my other gay friends. They highly recommended various size butt plugs in order to get myself ready for mens anal sex. Anyway, Ass Invasion is made so that it fits around my balls perfectly while allowing the discreet insertion of the butt plug into my tight little ass. Yes, I knew I had to try this one out.

It seemed to be the best thing to start out with because it didn’t look so complicated and I had a feeling that I was going to love how it felt in spite of my misgivings. After all, I had to start SOMEWHERE, didn’t I? Of course, I did and that’s exactly what I was going to do. Quickly, I placed my order before I could change my mind. Now, all I had to do was wait a couple of days for it to arrive.

 Happily, it didn’t take that long for the Ass Invasion Semi Thong to arrive because I had selected a faster shipping option. When it was delivered, I was ready to see how this was going to help me prepare for mens anal sex. Eagerly, I opened the package and removed the contents. The first thing I noticed is that it looked exactly as it had appeared on the koalaswim.com website. Holding it in my hands, I examined it closely and became a bit apprehensive. Was I really ready to start on this path? I had no choice because, apparently, according to my friends, I was really missing out on some of the most pleasurable sex imaginable.

Since I had already taken a shower before the mail arrived, I felt ready to try on my new thong. Following the cleaning instructions for everything, I finally went into my bedroom and stripped. It did cross my mind to call one of my friends to come over and assist me in this process but I just couldn’t bring myself to do it. If I was going to fully embrace who I am, I needed to know how to do things on my own. So that’s just what I did.

I was determined to find out what mens anal sex was all about and this still seemed to be the best way to do that. Slowly, I pulled on the Ass Invasion thong, taking care to get the cock ring and butt plug in the correct positions. Since I was a bit familiar with cock rings, I tackled that one first. Fitting it around the base of my cock, I found that it was quite comfortable and more than a little stimulating. Of course, that could probably have been due to my own excitement.

Now, I just had to figure out what this butt plug was all about. I have to admit that it was a bit intimidating but I was determined to make it work. I made sure to use plenty of lubrication because I really didn’t know what to expect and I certainly didn’t want it to hurt. Slowly, I started to insert the butt plug into my, at the moment, tightly clenched little asshole. Everyone said that if I was going to learn to engage in mens anal sex that I definitely had to relax. Well, let me tell you that when you’re first learning to insert things into your asshole, relaxing is a lot easier said than done. However, I took a deep breath and slowly started the penetration.

Ahh, I thought. That’s not so bad. In fact, it kind of feels good in an odd sort of way. Allowing the muscles of my ass walls to adjust to this new sort of invasion, I focused on  the rather stimulating twinges I was getting, which I must admit were beginning to feel quite pleasurable. Once I was comfortable, I slid the plug in just bit further. As it didn’t start feeling unpleasant or uncomfortable, I pushed it in even more. Suddenly, I felt a sensation that made me gasp. Had the butt plug found my prostate? I could only guess that was what had happened. It was also at that point that I decided that mens anal sex might just be something I wanted to do after all.

Settling myself into a more manageable position, I let the butt plug rest deep inside me right where it was while my hand reached down to encircle my surprisingly hard cock. I gripped it rather tightly and then started to stroke the shaft from the base all the way up and over the head. Suddenly, I realized that I was producing quite a bit of pre-cum and that it was happening very quickly. I had never known myself to start getting wet so fast, yet here I was with so much pre-cum that my hand was already sliding easily up and down the now very slippery shaft. As I clenched my ass muscles, I felt the butt plug do its work as it kept exerting pressure against my special love spot.

Oh yes, I thought. Mens anal sex may be somewhat wonderful after all! I simply couldn’t help myself. Suddenly, I was gripping my cock even harder as my hand slid up and down faster and faster. Before, I knew what was happening, the butt plug was massaging my prostate steadily from the way I was moving and hot white cum shot straight out from the head of my cock. I was astounded. I hadn’t cum like that since I first discovered the joys of masturbation years ago. Realizing that I literally could not control that orgasm left me not only breathless but speechless as well.  I managed to get cleaned up and then returned to my bed. This was definitely something that I needed to investigate more. It was in this way that I spent the remainder of the afternoon,  cumming over and over again as I practiced with my mens anal sex toy.

The next day, I decided I needed to have another one of these devices to help me prepare for anal sex. So I sat down with my computer and browsed the koalaswim.com website again. It wasn’t long before I landed on The Plugged Up thong. Billed as a swimsuit with anal stimulation, it looked like something I probably wouldn’t have the nerve to wear on a public beach, at least not at first, but maybe I might as I got a bit braver and more confident. The really cool thing about this thong is that it is held in place with a special butt plug. As I read on, I saw that it actually came with two sizes of butt plugs; a 3 inch and a 6 inch. This seemed like the ideal item to practice mens anal sex before actually HAVING it.  So, of course, I ordered it.

When The Plugged Up thong arrived within a few days, I was not disappointed with the results it produced. In fact, after playing with it for a few days, I worked my way up from the 3 inch plug to the 6 inch plug. I was pretty cautious about it at first but soon found out that I could handle more than I thought I could.

Finally, the day came when I felt confident enough to actively try out anal sex with a real live man. I just didn’t know how I was going to find the right man to do it with. Since I wanted it to be a special event in my life, I decided to just keep practicing with my mens anal sex toys until I met the right guy. Some of my friends thought I was being silly and they didn’t hesitate to make fun of me but it wasn’t that long afterwards that I was very grateful that I had waited.

I happened to be out one night at my favorite club when a drink was delivered to me from one of the most beautiful sexy men I had ever laid eyes on. I accepted the drink and motioned for him to join me. He told me that his name was Blake and that he had been watching me all evening, waiting to see if I was with anyone. I had to laugh a bit at that but I wasn’t ready to let him know that I couldn’t be more available. We talked, laughed, danced and generally had an amazing time together. As it got later and later, I wasn’t ready to say good night and neither was he. So I did the only thing I COULD do; I took him home with me.

Now, before you start thinking I’m some sort of slut, nothing of real importance happened that night. Of course, we kissed and made out quite a bit but after that we just made plans to see each other again. The BIG NIGHT didn’t come until after we had been seeing each other for two months. In fact, it was on our anniversary that I finally got to find out what mens anal sex is really all about.

It was a very special night. I had made an amazing dinner and set up my dining room with flowers, candles, and sexy music. The wine was chilling and everything was ready for our very own unique celebration. Blake arrived looking good enough to eat and we kissed eagerly. I let him know just how delicious I thought he looked but pulled away and led him to the dining room. He was properly impressed and I handed him a glass of wine. Dinner was perfect as we engaged in a bit of verbal foreplay between bites. By the time dessert was presented, we were more than ready for our very own version of something sweet.

Restraint was all a part of our anticipation so we played it to the hilt. When that first kiss took place, it took us straight back to my bedroom where there were even more candles. I had even taken time to spread fresh rose petals over my black satin sheets. Blake did pause long enough to appreciate all of my efforts and gave me that sexy little grin of his.

Of course, by now, we had discussed the fact that I was somewhat of a virgin when it came to mens anal sex, and I have to say that Blake had been more than patient with me.  I mean we had done our share of making out and 69s, but I always had the feeling that he was missing something by not connecting with me in that special way. Tonight, I was going to make sure that I remedied that. After all, I had spent plenty of time practicing with my items from koalaswim.com and I felt that I was ready.

When we were both naked and hard for each other, I reached into my nightstand drawer and placed a bottle of lubricant on the top of it. Blake glanced up and seemed a bit surprised to see it there and he looked back at me rather questioning. I looked up at him and smiled a rather wicked smile. He asked me if I was serious and I nodded. My only stipulation is that he start out somewhat easy because I knew that his very beautiful cock was quite a lot larger than my butt plugs.

From that moment on Blake did everything he could to make sure that I had a thoroughly great time. I did stop him, though, when I felt myself ready to cum in his mouth. I wanted that heightened excitement to be present when he entered me. He took care of all the lubrication details, his fingers lingering playfully around my tight little asshole, stopping to dip a fingertip in and out a couple of times.

Then he gave me one last chance to change my mind but I really wanted this; to feel his cock pushing into me. And that’s exactly what happened. Blake was very careful as he entered me. Something happened to me then. I suddenly couldn’t wait to feel him all the way inside of me, pushing against my prostate, just as my butt plugs had done. I moved my hips back against him, causing him to fuck me deep and sudden. It was definitely what I had been missing. I was so close to cumming that it only took minutes of Blake fucking me for me to cry out and let go. As he emptied his cock into me, I spurted onto my beautiful sheets.

Laying together afterwards, I knew that mens anal sex was something that I had never needed to fear.  Thanks to koalaswim.com and Blake, I could now lead a normal sex life of a very happy and fulfilled gay man.