First Anal Experience

The comments were so encouraging on my first entry of my first time as a cocksucker, I really enjoyed the comments and messages so thought I would share my next gay experience.

As mentioned in my first story, I didn't necessarily intend on sucking a cock that night but ended up thoroughly enjoying it. I kept on recalling the events sucking that black curvy dick, jacking off wanting to suck again.

I really thought about how to make this happen. I've been going to ABS and erotic cinemas, having cocks pop through gloryhole but I really was afraid to suck a strangers cock as it didn't really seem safe. Super exciting but not safe and again, did not want to have to explain any surprises, so this was out...for the time being anyway.

I did think of one guy - a guy at the health club that I've been flirting with for a couple months...showing hard in the showers, openly looking at each others dicks in the sauna and finally had gotten to the point of jacking off together in the sauna.

He was quite average but man, the way he would look at my dick, it was such a turn on. A couple of times when jacking off together, he would try to touch my dick but it was a bit too far for me at the time. Clearly, that had changed since my other experience I wrote about so I thought sucking him off would be a perfect fit for my desires.

The next time we happened to be at the health club together, the routine started out the same, showering with the curtain open, stroking our cocks and then moving in to the sauna.

As we moved to the sauna I gathered up the nerve to let him know that I was ready to be with another man...I'd like to suck his cock. A huge smile flashed over his face as he knew that I was new to the experience and he seemed to really enjoy that. He said that he was totally up for it but would want to go somewhere with a bit more privacy. I suggested in his car at the back of the parking lot, and then he suggested the nature path through the woods.

I knew exactly where he was talking about and had actually walked that path many times. He said he knew of a nice private place where we could be absolutely alone and not be bothered. I agreed and continued to stroke my cock which he told me to stop as he wanted every drop of cum from me. We agreed to meet at 6 in the morning and go for a walk on the nature path through the woods.

Now I had never been sucked off by another guy and it was clear that this was his intention so was both looking forward to it but a bit nervous as well. I thought how important it would be to suck him off first to make sure I went through with servicing him so this was my plan.

We met the next morning at the time and place we agreed to meet. He was fully in his workout clothes as well as a pink fanny pack, which was a bit odd for me as I was just in a T-shirt and shorts, not necessarily dressed for working out...but I was soon to find out it didn't matter one bit. As we met, we both said good morning he asked if I was ready to be with another man. I didn't tell him about the first cock I sucked but replied that yes, I was excited and couldn't think of anything else when masturbating.

He knew exactly the direction he wanted to go...we walked for about 10 minutes and honestly, we didn't say a word. In fact, I didn't even know his name, we never really talked that much, just looked at each others cocks and jacked off together...it seemed better that way.

Then he stopped and turned off the path, through some high weeds. Honestly, I did not even see a path so it was clear he had been at this spot a few times before. We walked through high weeds for a couple of minutes and then there was a bit of a path worn into the weeds that walked right up to some shorter trees in the forest. These trees provided cover from where we were walking from...you couldn't even see through it. He proceed to walk around the trees and I followed him around where I found a clearing right behind those short trees. There was soft long grass which seemed to have been matted down and seems that all the sticks had been moved to the side. I'm not sure how long he had been planning this or was I clearly not the first guy he's taken to this private location.

Then he turned around, abruptly and came up to me and started kissing me, really quite aggressively before he took a couple steps back. I think he was just testing me, making sure I was up for this and then he completely took off his clothes...everything, socks and shoes too. So I began taking my clothes off too - completely naked and it was so damn exciting...being out there in the woods, in the public, completely naked getting ready to suck off another guy.

He then came back to me and started kissing me - honestly, it was a bit aggressive for me and I remember thinking that this is what it felt like for the first girl I kissed. Mouth super wide open, teeth clanking, his tongue nearly down my throat - he was totally into this and I remember thinking that I can't believe I'm doing this.

I thought this was the right time to take his cock in my mouth and I stepped back and went to go down on him.

He put his hand on his shoulder and said he needed my cock in his mouth...that he'd been dreaming of sucking my cock. So, I stood back up and he dropped to his knees. He began licking my shaft...from my sack to the head of my dick...like a lollipop or ice cream cone. And then, without any hesitation, he took my entire hard dick in his mouth. I'm not huge but a good 6 inches and I swear I could feel the back of his throat. Not one gag, not one...he buried his nose in my pubes and breathed in deeply through his nose. Its what he wanted - it seemed like he had been dreaming of that moment and he was soaking it all in.

I remember placing my hands on the back of his head, not that I needed to guide his head at all, but I wanted to connected with him in that moment. He had a short hair but, practically a buzz and was partly balding on the top of his head. I didn't expect to be so turned on by holding another guys head while he sucked my dick but it just felt so out there...so naughty and raw.

He was a pro...definitely deep throat expertise but he really wasn't trying to get me off quickly as I found out he had another plan. He took my cock out of his mouth and said that he needed to have my cock in his ass. He begged me to fuck him, I hesitated as this was not what I thought was going to happen but he kept on, licking my dick upon each plea. He told me he was clean and that he has condoms...he doesn't care, he just needed me inside of him.

I thought it would be safe with condoms so I agreed. He reached for his fanny pack (now I knew why he brought the fanny pack) and gave me a condom and took out a bottle of lube.

As he spun on his knees away from me, he proceeded to pull a butt plug right out of his ass. I didn't even realize that he had it in there when we were walking or even after we took off our clothes. He lubed up his ass real good while I put on the condom and he said "fuck me...fuck me like the little bitch that I am". I was a bit surprised to actually hear those words but found out further that he was a bit vocal.

As I slipped my cock in his ass, it became clear he was prepared for this - there was no adjustment period that I would feel when using dildos in my ass when jacking off, he was all stretched and ready for me.

He took a deep breath when I pushed in and even whispered "oh yeah baby...I like that cock" and I began fucking his ass. He was on all fours and I was on my knees behind him, hanging on to his hips, pulling him back while I thrust in him. I really seemed to be getting in to it, he kept on saying "oh yeah...fuck me harder" and I thought I'd reach around and jack him a bit while fucking him.

Now first, I realized it is not that easy to reach around to jack someone while fucking them but when I did get his dick in my hand, I found it completely wet and oozing cum. I'm not sure if he was orgasming while I was fucking him but believe it was because I was banging on his prostate during sex. Either way, it was unexpected and really exciting.

He began getting a bit louder...alternating between "fuck me faster" and "fuck me harder" when he began quivering a bit...shaking out of pleasure. It was a real surreal moment - I remember just thinking and soaking it in. Here I am, in the public woods, completely naked, fucking another guys ass, seeing my red handprints from grabbing his hips and smacking his ass with him quivering there it was enough to put me over the edge.

I came so hard, it felt like the orgasm kept going and when I was finally done and slowed, he asked me to stay inside him for a little longer. I felt his sphincter clenching on my cock - I'm not sure if we was doing that intentionally or if it was unintentional but if felt like his ass was milking every last drop...like he had said the day before in the sauna.

Finally I pulled out and he asked if he could have the condom which I obliged and he tipped it in his mouth and ate my cum out of the condom. He just laid there, breathing heavily on his side saying how great it felt.

Honestly, the moment felt like it had passed...we were both a bit exhausted and catching our breaths so I asked him if he would like me to jerk him off. He declined and said he was just going to lay there for a while but thanked me anyway.

I thanked him, got dressed and told him to have a good day...turned and walked back to my car. I drove to the health club to use the shower and went to work like any other day.

After that, I thought it best to not return to the health club as it was in the community I lived in and never saw him again. I went back to the clearing occasionally, hoping to find him there with someone else...or at least find him jacking off but he was never there. I would always jack off and leave a load in the same place that I fucked his ass but never ran in to him in the woods.

I never even knew his name but honestly, it's better that way. One thing was for sure though - I now needed to feel what it was like to be fucked in the ass. I needed to find out how to set this up in the right situation...which I ended up doing and will share that next first for me if the comments are again so encouraging.