First time gay sex story: From curious to first time – Part 2

Years passed by and the same questions would come across my mind at times….What if Me and John did go all the way that night? How would it of felt? would I of liked it? Would I really be able to go through with it if the chance came up?

I also began to question my sexuality….Am I Bi?? Being married and living a very straight life….I started wondering a little. Dont get me wrong, I love females, pleasing females, fucking females….especially the way my Big piece of equipment makes them react….but I always remembered the feelings I had gotten when me and John had our little playfights.

I was working in a business office. Everyone was always dressing nice, business attire! Ladies would look HOT. I was getting alot of attention from the ladies…but being married I would just say thanks and kept it at that. There were a few gay guys there as well. Some of them would hit on me as well, but me being straight and married…they knew they had no chance but I guess they would just test me to see if I would react in a way they would like but i Never did.

One day, after work, one of the gay guys came up to me and we started talking. Nothing awkward or anything, just talking. Pretty much just hanging out after work conversating, then we walked to the parking lot and started getting into our vehicles… As I was getting ready to leave he drove up next to me, in the opposite direction, his driver window was next to my driver window, and he asked me “Have you ever been with a male before?” .

I just laughed and said “NO” . He apologized and said he wasnt trying to disrespect or anything but just had to ask. Then he told me that if I ever wanted to try, that he would love to be my first. He complimented me on my looks and body. I laughed again and told him thanks but that wasnt my thing. He said Ok, but the offer was still there! As I drove off I was kind of shocked, but got a little turned on.

I again thought about John and what we had done! Nothing changed at work, Me and the Gay co worker were cool and nothing was brought up. We kept it cool, but the times we would run into each other alone he would tell me. REMEMBER MY OFFER!! I always just laughed. I began to think about it more and more though.

One weekend, wife was gonna be out of town, and I was home alone so I decided to just jump into a male/male chatroom. Just to check things out, didnt expect anything. Chat was full of hardcore gay guys…So i figured this is not what Im looking for. I then got a ping from a IM. I opened it up and it was a normal. Hello, how are you this evening message!!

I replied to the message. Was a normal message, not like what I was seeing in the chat. Ended up being an older white gentleman, in his early 40s he said. We had a nice long respectful chat. His name was Gary. We chatted all night. He ended the chat asking if we could chat again, and I said yes. The next night we chatted again.

I told him about my situation and what had happened as a teen. He was very nice and explained alot about the site and situations. He seemed very real, honest and respectful. We chatted all night again. He ended up living in a city about 20 minutes away. What a coincidence I thought. We continued to chat. I would log on every chance I had, and we would chat alot more….after a few months of chatting we started chatting more about possibilities!

He would ask me , if we ever met, what would I want to do or expect? this went on for several more weeks. We got to point where we were both very comfortable with each other. We started sending each other XXX pics of ourselves. He would send statements like WHAT I WOULD DO WITH THAT, NO WONDER YOUR ALWAYS GETTING HIT ON! His pics were hot as well.

He was an older gentleman, but he was very fit. Nice swimmers body as well. He loved the pics of my cock…8.5 inches and thick…. he would message me saying he wanted to taste me. I let him know I didnt think I could ever suck another mans cock or kiss another man. He would always tell me not to worry about that. If we were ever to meet, it would be at my pace.

He wouldnt push anything. He made me feel very comfortable. I couldnt believe I was talking to another man about sucking cocks. It would get me hot and hard!! As we got more comfortable we decided to exchange face pics…..He loved my pics…..His were nice as well. Older white male, but handsome, blue eyes, very fit, respectful and a gentleman! I started to think, will I be able to go threw with this??? Will he be the one??

A year had passed, and our chats became phone calls. we kept in touch from time to time. Seemed like by this time we were both HOT for reach other. Seemed exactly the same as the way me and John were, only we had never met. I had let GARY know that I wanted to meet him, but that I wasnt sure I would be able to go through with anything.

He was ok with that. He assured me all the time that I didnt have to worry about any expectations. He would just mention that if he had a chance to have me, He would make sure I got what I wanted and take his time to make sure I would want it again. He would tease me in our phone calls. Telling me little things he would want to try as he looked at the pics I had sent him.

He would get me super hot. I ended up sending him another picture. One of the hottest pics I had sent him. It was a shower pic… I was bent over lightly….Soap suds going in between my ass cheeks…with my legs spread open…… and you could see my big hard cock just hanging down in between my legs!!
That pic got me hard when I would look at it, and once i sent it to him….He said he had to meet me now!! Even if nothing ever happened, he just had to meet me!!

2 months passed and my wife began to plan a trip, I wasnt gonna be able to make it so I was gonna have to stay home alone that weekend and I started getting a little excited! Me and Gary talked a few times but I never mentioned that I may be home alone that weekend. The weekend came, and my wife left early friday morning.

When I got home from work, I jumped online and seen that Gary was online as well. We chatted a little and I began to look at all of his pics and started thinking to myself……Can he be the one? I like his pics, I like his looks, I think he is attactive and he has a nice body. So as we chatted I asked him if I could call him an a few and he said ok and I logged off.

I contemplated the situation and I told myself that even if nothing would happen, I had to atleast use this opportunity to meet him. So I called him and we talked for a few minutes!! I heard the gasp in his breath when I mentioned to him that I was home alone. He got a little quiet. Like if he was thinking the same thing I was thinking…..

After a few minutes he asked if I would like to go over?? He made sure to mention that it was ok if I didnt, and that if I did end up going that I had nothing to worry about, Nothing was going to happen if I didnt want it to.

I told him I felt comfortable enough and that I would like to visit him, to atleast finally meet him in person! The sound of happiness came over his voice and he said cool and asked what time he could expect me! I told him I was gonna shower first and be there in about 2 hours. He said perfect and he hung up!!

I got nervous and jumped into the shower. While I showered I began to think about the possibilities and noticed my cock began to stiffen up! I couldnt believe that me thinking about another man was actually turning me on! I shaved my body completely and trimmed my legs. I put on some body spray to make sure i smelled good, just in case. 🙂 As i began to pick out what I was gonna wear…

I seen my wife had left her clean laundry in the basket in the room. It was all her sexy undies and bras!! I had sent him a pic of me in one of my wifes thong underwear and he loved it, so I decided to wear the same pair for the night! Then I put on some shorts and a nice shirt. I sprayed cologne got some gum and headed his way………………………………………..

I drove by his house once, and got super nervous! I went around the block and thought to myself again, Was I sure I wanted to do this! Nothing had to happen and I again I told myself lets atleast meet him for once in person, so I drove back to his house and parked. Grabbed a piece of gum and walked up to his door, I rang the door bell! When he answered the door, we both immediately made eye contact and Im sure I had the same expression as he did!

The expression of wow this guy is hot. He looked very clean cut, alot better in person than his pics and I feel he did the same from his reaction. We introduced each other and he welcomed me into his home and the settings were perfect! I had always mentioned to him that I pictured my first time with a male to be romantic, dim lights, soft music playing etc……. and he had did just that!! He had a nice house, everything was dim except for the kitchen light being on!

He had on some slow music playing very low. I got nervous as I walked in. He motioned me over to sit on his couch and he sat across from me on another couch and we began to talk, in person! I could tell he was checking me out, and I did the same. After a few minutes it seemed like we were old friends. Talking about alot of what we had chatted about.

After awhile, he stood up and asked if I wanted something to drink and he walked into the kitchen. As he stood there, I began to look at him long and hard. I thought to myself is he gonna be the one again? The chance is right here in front of you. what should I do? nerves came over me again. When he walked back, he brought me my drink and sat on the same couch this time.

Very close to me. We chatted some more, but this time i noticed he was getting a little flirty. I got super nervous and Im sure he noticed, but I was liking it.

He brought up the pic I had sent him of me in the shower. I laughed as he described it in person and how it got him so hot then He placed his hand next to my thigh! I noticed he was maybe testing to see if he could maybe try to make a move on me, but I wasnt giving him a yes or no response. As he got closer, I paused then asked him if I could use the restroom! He paused and said….Yes sure, and pointed in the direction of the door.

I walked into the restroom and locked the door behind me….I didnt have to use the restoom, but that was my getaway at the moment. I stood in the restoom starring at myself. I thought about the feelings I have always had from the experience with John. I thought about Gary, How I liked that he was such a gentleman, He was older, mature male, Hot looking at the same time with a hot bod! The thought of an older male fucking a younger hot male seemed to be a HOT idea as well. I thought a little longer and then I decided….!!

After a few minutes I came out. As I walked out, he was sitting on the same couch facing away from me! I took a deep breath and walked out. I said I GOT A SURPRISE FOR YOU GARY!………………….

I came out of the restroom only wearing the black thong and a black muscle shirt….. I walked right in front of him and turned away from him and slightly arched my back and spread my legs……..making my ass stick out a little. I felt myself shaking a little from the nerves. I heard him just gasp and whisper WOW!

The room was dim, but it wasnt to dark. He could see exactly what I was wearing and had a good view of all of me……….. JUST LIKE THE PICTURES he whispered. I got more nervous when he placed his hands on my hips and slowly began to move them up and down…….then working them toward my but cheeks!! He caressed and squeezed them and gently gave me a little slap !

The thoughts of, is this really happening raced through my head but I continued! the sound of his deep breaths began to turn me on, knowing this man had the hots for me really had me going and he noticed my cock begin to get hard! He then reached in between my legs and pulled my cock out of the side of the undies I was wearing and slowly began to stroke me!!

Im sure the scene would of looked like if he was milking a cow, but it was Me he was milking!! My cock got fully hard in his hands and this gave him the sign that I was liking what was happening and that he could continue. At this time he did something I had never had done to me…..He pulled my cock to the back, in between my legs to where he was at……and placed it inside his mouth…..

I gave a slight moan once I felt his mouth on my cock!! The thoughts still were running across my mind but the feeling was so good that it was slipping away. He sucked my dick for awhile longer until he knew he had me nice and hot. He knew exactly what he was doing. Then he released my cock with his mouth and again began to slowly stroke me with one hand.

I felt the other hand pull at the rear of the thong, moving it to one side, then again I felt something I had never felt before! Something warm and wet was in between my ass cheeks…..I turned around to see and his face was digging into my ass…It was the first time I had ever been rimmed!! The feeling of his tongue licking my asshole was undescribable, his strokes began to get harder and a little faster as he licked my ass harder as well.

My breathing became deeper and faster as well. Little moans would come out of me. Gary then released my Cock and placed both hands on my ass cheeks, one on each cheek. He used them to pull my cheeks apart and began to lick only the center of my asshole! Little by little pushing it into me more and more! Within a few minutes he had his tongue inside my ass as deep as he could and started moving his head back and forth. For the first time ever, I was being penetrated by something from behind!

The thoughts again came across my mind about what was happening, but by this time I thought to myself…ITS GONE THIS FAR, IM GONNA LET WHAT HAPPENS HAPPEN NOW and I relaxed and began to enjoy the moment! I believe he noticed this as well, especially once I started to push back against his tongue……..letting him know I wanted it in me!!! After a few minutes of him penetrating me with his tongue, he pulled back and whispered. YOU ARE SO HOT and he stood up!!……………………………..

He grabbed me by the hand and walked me to his bedroom……by now, the nerves had settled down and my cock was rock hard! Gary knew exactly what he was doing and he had me exactly where he wanted me!! He walked me into his dark bedroom…the only light we were getting was from the kitchen, but it wasnt much. We could barely see anything.

Gary then gently positioned me, bend me over his bed. My elbows were leaning on his bed while I stood on the floor. Ass up in the air. Again he pulled my cock from behind and started to suck me from behind….Not sure if it was the darkness, but I felt more comfortable to moan and I did just that. I began to lightly moan like a female.

He used his saliva to lube my asshole and then I felt him gently begin to use a finger to play with my ass. After a few minutes of this, I felt him push his finger into me…….the nerves kicked in again for a second, then they were gone from the good feeling I was getting of having my cock in his mouth and his finger in my ass!!

He used his finger to penetrate me…in and out….and in a circle motion. Then he pulled his finger out and lubed my asshole up with saliva again, and this time he placed 2 fingers by my whole and slowly worked them into me.

The nerves came back again, as I realized what he was doing. He was getting me ready I assumed! The nerves were not that bad though, as he continued to suck my cock from behind the whole time. Once both his fingers were inside me and he noticed I was a little comfortable with them, he again began to pull them in and out… faster at times and in a circular motion.

I then felt my Cock pop out of his mouth and he slowly removed his fingers from being inside of me! He then whispered to me to get on his bed. The nerves filled me again. He placed me in the middle of his bed, on my hands and knees. I was very nervous now, I knew what was probably gonna happen, but I wasnt sure what to expect.

As I was on his bed, I felt him tug on my cock again from behind and he slowly stroked it…..his mouth and tongue again focused on my asshole….with that the nerves calmed down again…..This time he started tugging on my cock a little harder……..At times it hurted a little but the pleasure outweighed the pain part!!

Then for what seemed like forever, he stopped and was doing something…..I heard an opening of a package…….and then again I felt a pull on my cock…..The bed began to move…as if he was climbing on and thats exactly what he was doing. Warmness again surrounded my ass area from his saliva……then I felt something against my ass…..

Nerves rushed through me….I questioned myself is that his cock?? ………………….when he pushed it in, I realized it was his finger again. Only one. He pulled it in and out a few times and again worked it in a circular motion. Getting me ready one last time I assumed.

Once he removed his finger, I felt the bed move again….and i knew he was behind me in between my legs…….. I heard a bottle pop open and the sound of him squeezing it…..Then I felt his fingers in between my ass cheeks, my asshole and cheeks felt very wet from the lube he had put on . again, I was filled with nerves.

I had a pretty good Idea of what was probably gonna happen next. Is this really about to happen? I asked myself over and over again. I gripped on his bed sheets not knowing what to expect as I felt the bed moving again, as if he was getting into position. I couldnt really see anything. My breathing became deep and faster as the nerves ran through me as he placed his hands on my hips.

He then moved one hand and again I felt something up against my asshole! He slowly moved it and very slowly began to push it in. The tip started to go in, and my nerves calmed down a little when I began to think It was his finger again!! He slowly pushed in and out and i knew it was his finger, but he only was using the tip until Gary placed both his hands on my hips and I still felt the tip penetrating my asshole! Gary slowly pushed and pushed and pushed and started pushing more and more into me, gripping my hips tighter with each push!

I quickly realized this was much bigger than his finger now! Gary slowly and gently kept on pushing and pushing into me until I felt his crotch area come to rest up against my ass cheeks!!! He lightly moaned out YOU FEEL SO GOOOD!!! and thats when I knew………Thats when I knew and felt what I had been wondering and maybe wanting all these years!! I had a cock inside of me and now I was gonna get fucked by my new friend Gary!!!

Gary knew how to treat a male….Especially a new one!! Once he got his cock in me, he gently and slowly thrusted his hips….working my asshole and molding it to his cock…..he would slowly pull out and slowly push back in…..I think he noticed how tense I was……I gripped his bed sheets with every push!! My thoughts were that I was finally feeling what I was thinking about all these years…………………………………

And I was liking it!! Once my hole got used to his cock, the feeling of him being inside of me was real good. I always thought about it, but never knew how it would feel…………and now I knew how it felt, and I couldnt believe how much I was liking the feeling!!! He realized this as well, as I became more relaxed…..

I was able to release his bed sheets a little as he slowly continued to go in and out of me!!! What I did next showed him and myself that I was liking being fucked!! I began to push back against his cock everytime he would thrust into me…..When I did that, He started penetrating me a little faster and gripping my hips nice and hard.

He started moaning out…YOU FEEL SO GOOD!! and I began to breath deeply and moan louder…..Like a female at times!! at this time, I remember thinking IM OFFICIALLY BEING FUCKED………when he was fucking me harder……then slowing down and working my hole slowly and stretching it then again speeding up especially when I began to ask him to FUCK ME HARDER!!!

That really turned him on…….Hearing his deep breathing and grunts would get me even hornier!! I laid my head down on his bed and left my ass up in the air for him as he continued to penetrate me…..seemed like he fucked me doggy style all night!! Then he pulled me hard back into him, pushed his cock deep in to me and began to grunt, moan and gasp ………..

I knew he was cumming!! I didnt feel anything because he had a condom on, but the thought of having a man deep inside of me, and I made him cum was super hot!!! after he gathered himself…he cleaned up real quick and I stood on the bed, Nervous , not knowing what to do and I was still super hard!! Then Gary came back and turned me around and laid me on my back…..

He grabbed my cock and whispered “YOU HAVENT CUMMED” and put my cock back into his mouth…..reached under me and slipped a finger back into me from underneath.

He sucked my dick so good………. I was ready to cum, but got nervous , wasnt sure if he wanted me to let him know….or what?? But the sounds of him gasping for air, slobbering on my cock and licking my head along with his finger in my ass….got me to the point that I couldnt hold back!!!! He moaned as I began to explode into his mouth……by his moans I knew, thats what he wanted….He sucked on my cock until there was nothing left……..and completed it all by swallowing!!!

I laid on the bed motionless….in the dark………not knowing how to react…..he allowed me to gather my thoughts which I thought was very cool……. after a bit, he turned on a light and let me clean myself up.

I got dressed and we chatted a little. Was an awkward moment, but i believe he knew I must of had many thoughts running through my mind. I told him thank you and gave him a hug and let him know I was gonna head home. He asked If I was ok, and I said yes as he walked me out. Again I told him thanks and that I would keep in touch. He said please do and that it was nice to finally meet me!!

As I drove home, many thoughts ran through my mind! Did this just happen? should I keep in touch with him. Would you do it again?…………..then I relaxed and told myself…Yes it did happen…..And I liked every bit of it…..When I got home I messaged him apologizing for leaving like that and he replied with not to worry because he knew I had alot on my mind but that he hoped it was what I wanted.

I replied with Yes it was and that he was a great gentleman and good looking and everything else he did was amazing…………I wondered if I would be able to do it again, and told myself He would be the only one I would keep in touch with from now on. No need to be in chatrooms!!……………….We kept in touch and messaged each other about that night…….Think a few weeks later we were both worked up again……….And one weekday I was gonna be working in his area……………..I let him know the night before that I would be in his area…….He asked me to stop by to say hello if I had time and….

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