My First Encounter with a Straight Dude (part 2)

[Guest NSideYouNow]

I am not going to start this part by back tracking to the first part. If you really want to keep up you can go read the first part then come back.

I couldn't wait for the damn meeting to get over and I kept finding myself catching a glimpse of his crotch from time to time. I kept remembering how good it tasted and responded to my mouth movements. But I had to try and stop thinking about it as my cock kept trying to come alive. When my cock becomes erect it is literally impossible to not notice it from across the room. So I kept my mind on the meeting for the remainder of the day.

After the meeting I gave him my cell number and rushed back to the hotel. We decided to meet in a couple of hours at a restaurant he had been to before so I decided to jump in the shower and get freshened up. My mind couldn't help drifting back and forth from his delicious cock to his smooth hard round ass. I couldn't help but think about how I just may be tapping that virgin ass tonight and gave my own cock a quick jerk or two in the shower. Before I know it I have already planned out the entire evening and how I planed to position him on his back at first so I can see the expressions in his eyes as I move my cock in between his velvet cheeks and push past that twitch I felt the night before. While I am doing this I lose track that I am still stroking my cock and I suddenly realize that I am about to cum. At this point I think OK that is alright and it just means I can go much longer and won't shoot before he has had time to get into it. Just as I feel my legs start to ache and balls start to tighten up I hear my cell phone start to ring. But it was too late as my cock had a mind of its own and started shooting cum and my knees tried to buckle from under me but I grabbed onto the safety rail and let out a very loud moan of pleasure and relief.

I quickly rinsed off and grabbed a towel so I could see who had called. Man was I really disappointed when the call ended up being from Steve (oh yeah his name was Steve) and he said that something had come up at work and that he wouldn't be able to make it. I said a few choice words but eventually got over it and decided to just go get some dinner and perhaps I would go on line later. I went a head and went to the restaurant he had suggested as I was hungry and the place sounded like a good choice. I had to wait about twenty minutes as they were very busy but I eventually got seated at a small table and started looking over the menu. I couldn't help notice how good looking all the waiters were but I thought gee I must be horny now that I have missed my adventure. I motioned for the waiter to take my order and as he started over to my table someone came up from behind me and said "Damn I was hoping you would be here". I turned around and it was Steve and my cock pushed its way out of my shorts and down my pant leg. Well, like I said earlier, Steve took one look and said "And I can see that you are very happy as well". We both laughed and I quickly pushed myself more under the table.

I asked what happened and he said that something at work had gone bad and they thought he would have to fly home immediately. But after he left a message for me he called them back and they were able to correct the problems over the phone. He said he went by my hotel but I was gone so he thought he would try the restaurant. I couldn't help but ask him if he thought all the waiters were really good looking or not and he replied that is why he likes this restaurant. We ended up chatting while eating for about an hour and then decided to go back to my hotel.

It is much earlier than it was last night so I was geared up for a longer session with this dude. When we get to my room he says he will be right back and goes into the bathroom. I turned on the TV and within a few minutes he comes back out totally nude. All I could say was 'NICE' and he smiled and sat down next to me and started kissing me. He was a lot braver this time and had no problems reaching down, with his tongue still in my throat, and starts undoing my pants. I reached down to help and he pushes my hand away and continues by unzipping my fly and reaching in and rubbing my already hard cock. It didn't matter that it was already hard but when he touched it my gawd it felt like it grew even bigger and he lets out a nice moan as he is still probing my mouth with his tongue. After a few tugs on my cock he lets go and moves up to my shirt and continues until all the buttons are undone and he has his hand caressing the hair on my chest. I try to move and he holds me firm in place with his hand on my chest. He finally lets go of the lip lock and starts kissing my face and then continues down my neck until he reaches my chest area. As he starts to softly bite down on my nipples he moves his body around so that his legs are more up toward my face. So I reach over and start caressing his body and can see he is clearly excited by the way his cock kept jumping. I reached over and firmly grabbed it and he let out a muffled moan. I kept one hand on his cock and started caressing his smooth legs and he quickly spread them so I could continue caressing all the say to his balls. I grabbed his ball sack and started playing with it in my hand and he at that point moved further down until he was now slowly kissing and licking my cock.

Well we both let out a moan and with that I grabbed his legs and pulled him over the top of my head so that he is now upside down with my cock in his mouth. I quickly spread his legs apart and grab his cock and start licking the head and he jerks a bit. We are currently on the sofa so I push myself to one side until I am laying on my back and he is still on top of me with my cock in his mouth. I have to admit this boy knows how to suck. I just happened to have a bottle of lube on the table so I reach over and put some lube on my finger tips. I take his cock in my mouth and start sucking slowly while at the same time I reach up and start massaging his ass cheeks with the lube. He tenses up for a moment and then realizes we aren't there yet and goes back to work on my cock. He is even trying to deep throat me and gags several times but keeps on sucking.

As my fingers probe his cheeks I slowly start to move further in and I get a sigh of pleasure from him so I continue in until I feel that tight pucker I had felt the night before. I gently start rubbing my fingers as slow as I can to try and get him comfortable. I continue this for at least twenty minutes and then I started to press a bit harder and my finger slipped inside his hard tight hole. I thought to myself that he is going to scream but I don't get any reaction from him so I keep my finger in and slowly start moving it in and out and around. I was glad we had all night because I didn't want his first experience to be a bad one and damn it I was having a great time. I could now feel his body breathing a bit harder now so I decide to try another finger. So I slowly pull the one out and then start massaging again and then let two fingers find the mound. I started to push both fingers in and within seconds they were both fully inserted and I was met with only a bit louder moan from his cock filled mouth.

Both of our bodies had become a bit warmer and he came off my cock long enough to ask if I could turn on some air. As much as I didn't want to move I made a slight movement and he came off my cock quickly and rolled onto the floor with a big smile. I quickly jumped up and turned on the air and as I made my way back over to him he got up and said lets go into the bedroom. I was OK with that so we went into the bedroom but I grabbed the bottle of lube on the way. He laid down on the bed on his back and as I went to drop between his legs but he raised up and pulled me down onto him and planted another wet kiss on my lips.

After he kissed me long and hard he whispered in my ear 'Will you fuck me now?'. I had a big grin on my face but told him I wasn't sure he was actually ready for my thick cock yet. He replied that he would like to try as he really wanted it bad. He looked up at me again and said 'How do you want me?' and I said you are in the perfect position because I want to see the look on his face as I took his virgin hole. I reached over and grabbed the lube and then it hit me. I said 'Oh My Gawd, I don't have any condoms do you?'. He got a look of panic for a moment and said no but then looked up at me again and said 'Are you clean?'. Well I had just been tested a month ago and I told him yes but if he wasn't comfortable with it we can stop. He said hell no and that he wasn't waiting for it another minute. He takes the bottle from me and starts to lube up my now purple headed dick and it felt so good having him caress my dick with that lube. I took the lube from him, put a good amount in my hand, reached with the other hand and started lifting his legs, and then slowly started massaging the lube over his tight puckered hole. He let out a small moan as his ass was very hot and the lube just added to the excitement. I quickly returned to having two fingers inserted and he said that it wasn't bad and actually felt good. I told him to expect it to hurt the first time but I would try to be as careful as I could.

Well now I am in the process of putting a third finger into that tight little hole and his eyes light up with excitement and he says he is ready and for us to try. So, I push his legs a bit higher into the air and position my cock at the base of his hole. I can actually see his hole twitching and that excited me even more. I asked if he was ready and he said yes so I place my cock at the entrance and slowly started to push in. All of the sudden his eyes got real bit and he said OMG is it in now? I looked down and couldn't help but chuckle and say 'Son, only half of my cock head is in'. He looked a bit panicked so I moved back out. He quickly says no keep going and I will get used to it. So I place my cock at the entrance again and start to push a bit more now and all of the sudden the head pops in and he lets out, to my surprise, a very load moan and his eyes went into the back of his head. I held my position and waited for him to return and when he did he said 'That is fucking awesome'. I asked if he was really OK and he said that it does hurt some but he was ready for it and lets continue. Well as he is talking to me I am continuing to push in. By the time he gets done with lets do it I tell him dude I am all the way in now.

At that point he lets his body relax some and a big smile comes across his face so I tell him that I am going to start pulling and pushing now and for him to tell me if it hurts too bad. He agrees and I start pulling out some and he thinks I am going to pull all the way out and lets out a yelp of don't pull out. I reach down and put my hand over his mouth to let him know to not worry about it and pull out just to the edge of my cock head and then slowly start to push back all the way down until my balls are resting on his ass cheeks. As I am now starting to turn the speed up I start to see all kinds of emotion going through his eyes but I know he is really loving it as he has now tried to grab my legs and pull me further into him. We go on like this for about twenty minutes and his breathing starts to get really fast and the next thing I know he is shooting his load up all over his stomach.

I start to pull out, as some guys can't take it any longer after they cum, but he reaches up and pulls me back into him. He looks up at me and says that he has never cum before without stroking. His eyes were blue but at that moment they got really bright black and I had never seen anything like it before. After he finishes shooting his load he starts trying to pull me further into him so I start pumping his ass a bit harder now only to draw more moans out of him. I decide it is time he learns another position and quickly pull out. But before he can say anything I quickly flip him over and onto his hands and knees. Once he realized what was happening he spread his legs and I quickly placed my quivering cock at his damp hole and pushed all the way in with one hard push. He let out a yelp and we both fell to the bed. But I pulled him back up and start pounding his ass as hard as I could and he seemed to respond with each push and pull I made.

Well now we had been going on like this for about forty five minutes and I knew I was going to lose it sometime soon. As I continue to bang his ass I informed him I was about to cum and where did he want it. He replies to not pull out so I just continued to bang his now red cheeks and I could feel my legs start to strain and could feel the heat starting to move up toward my throbbing cock. I let out a moan to let him know I was about to cum and he reached up and started stroking his cock and with a couple of minutes I can feel the cum starting to shoot out of my cock and into his ass. He apparently could feel the hot cum dumping into his ass as he let out a OMG and then started to shoot his second load onto the bed below him. I am now holding onto his hips as all this excitement was making me a bit dizzy and I was afraid I would going to pass out. But Steve had other plans and started shoving his ass back and forth on my cock trying to get every last drop of cum out of my dick. When we were finally done, and I withdrew my cock from his ass, there was not a drop of cum left to come out. We both fell on the bed with sweat falling off of us and just laid there for about fifteen minutes saying nothing.

I finally get over my dissyness and turned over and asked him how he was doing. He replied back that he was very nervous at the beginning and actually scared but said that the two of us got along so well that he quickly became comfortable with me and knew that it would all work out somehow. I asked him if bottoming is something he would want to continue doing and he replied back with Hell Yeah. We laid there a while longer catching our breathes and watched some boring TV show. When that was over I started to get up and said I was going to clean up a little and he jumped up and said that sounds like a good plan. I get the shower going and we both climb in and he immediately starts kissing me again. When he lets up off the kiss he looked at me and said 'You want to fuck in the shower?'


Look for chapter III and I am sure you won't be disappointed.....