So This is What It's All About

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I never knew what awaited me.
1.9k words
4.5
36.4k
25

Part 1 of the 2 part series

Updated 06/07/2023
Created 06/30/2015
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This is a story about my first time with another guy.

The summer before my nineteenth birthday I went to visit my dad who had moved to another town after my parents divorced. He was living with his girlfriend and her kids, a son who was 20 and her daughter who was 18.

I hit it off pretty well with dad's girlfriend and her kids. Her son Mike and I really seemed to get along well, having the same interests and we were soon roaming everywhere on the farm. He was about 5' 11, stocky, blonde, and already had a neatly trimmed beard. I was 6', slender, athletic, with dark hair. That first night after dinner, we watched some tv and visited till about midnight and then everyone started getting ready for bed. Being that it was only a 3 bedroom house I soon realized that I would be rooming with Mike.

We headed back to his room and when we entered, I noticed there was only one bed and thinking I was going to sleep on the floor, I asked him for some blankets and a pillow. He then told me that since he had a king size bed that he had no problem with sharing. We then proceeded to get ready and laid down and started talking about what we had done that day and what we could do the next. Like all young men, of course the talk got around to girls and sex. We talked about who we would like to get with, how many times we had done it, and what we liked.

It made me wonder a little when he asked me how big my cock was, but I thought what the hell, we are friends and I told him that I was only about 6 or so inches long and he said that he was a little larger than that. He asked me if I ever masturbated, to which I replied, don't we all and laughed. He laughed as well and talk centered around cars and sports until we feel asleep.

I was awakened later by the sensation of something softly rubbing against my ass cheek. At first, I laid there wondering what it could be and then I heard and felt a slight hiss of excited breath against my neck.

My immediate reaction was to jump up and ask him what the hell he thought he was doing, but the hardening member in my own briefs made me hesitate. I thought to myself that if it excites me this much, why don't I just see where this is heading before I overreact. Its not as if I can't stop it at anytime you know. So I just just laid back and let him continue to rub what I now knew was the head of his cock against my ass while he slowly masturbated.

I had to admit that the sensation was very stimulating and after a bit my cock was so stiff that it started to do the thinking for me. I reached back and took hold of his cock, amazed at the hardness and softness combined and started to help him masturbate. Of course he froze for a moment and then he released his cock, allowing me full access and reached around and started rubbing mine through my underwear. I never thought that it would feel that good, stroking another cock while someone else handled mine but I was more than ready to experience more.

We stroked each other for awhile and I found myself really loving the feel of his cock. It was quite a bit larger that mine, probably 7 1/2 inches and quite a bit thicker and was uncut. Being circumcised, I had never really noticed another uncut cock before but I had heard of them of course. I did get a thrill though everytime I worked his foreskin up over this cock head, making him jerk with pleasure. He rocked his hips slightly as I worked his cock in all the ways that I like to do my own. Gripping it loosely and sliding my hand up and down the shaft, stimulating all the sensitive spots and pushing down around the base, making it jut out as far as it could, making the head swell up nicely.

He impatiently told me that these have to come off and slid my underwear down and continued to stroke my cock with one hand while I kicked them away. He slowly rubbed my ass with his other, occasionally running his hand down and cupping my balls. I was hard as a rock and wondering why I had never thought to do any of this before. I realized his cock had started to leak some and was lubricating my actions, making him moan a little in my ear as he nibbled on my neck. I was a little anxious when he slid his hand back and slowly started to massage my anus with a finger, slowly making circles around it. Surprisingly it felt really good and I found myself arcing my back to allow him more access to that special spot. The combination of both his hands was making my mind reel and opening up whole new worlds to my imagination.

I was disappointed when he stopped what he was doing and leaned over me to open a drawer in his nightstand to remove a couple of things. He then laid back down and fumbled a bit in the dark behind me with something and then started to caress my ass again.

I soon felt a coolness on my asshole and then a finger started to circle it again, slow at first, but a bit faster after a bit. I felt it relaxing, opening up to the probing and it only took a minute till he had inserted his finger in my ass and was slowly starting to work it in and out. My cock was literally jumping around at this point and I almost exploded when he reached around and started to stroke it again with a lubricated hand. He realised what was about to happen though and gripped it thoroughly around the base to stop the volcano and whispered in my ear, not yet, it only gets better.

About to go out of my mind at this point, I desperately looked around trying to focus on anything but blowing a load and I realised he had worked a second finger into my ass, making things feel weird but pleasant as he steadily worked them in and out of me. This got me back under some semblance of control so I reached back to play with his cock some more and found that he had put a condom on his cock earlier and had lubed himself up. I think I stiffened a bit when I figured out that he actually planned to fuck me, but he relieved all my reservations when he whispered in my ear that I was going to love it.

His fingers did feel incredible in my ass and I was pushing back on them, wanting more so I whispered over my shoulder for him to fuck me. He removed his fingers and kissed me on the shoulder as he slid lower in the bed, maneuvering himself into position to grant my wish.

His cock head felt even bigger as he slid it up and down my ass crack, even slapping it against me as he enjoyed the feeling as he searched for my hole. The head of his cock felt so large as he began to gradually push into me and it hurt a bit so I placed my hand on his hip, but he whispered to me that he wasn't going to hurt me, which made me relax just enough and we both moaned as his cock head slid over that special ridge in my ass, making everything feel like it belonged.

He stayed like that for a minute, letting me get used to it, and then started to work his hips, easing a bit more into me with each stroke. It amazed me that the pain had suddenly turned to such pleasure. He stopped pushing and laid still after an intense minute or so and started to kiss me on the neck again and told me I had taken it all and he just wanted enjoy the feeling for a bit. Unbelievingly, I reached down between my legs and felt his balls pressed firmly against me, right below my balls and felt a bit amazed myself.

Then while I fondled his balls he started to slide his cock in and of me in full strokes, pulling out till just the head was in and then burying it in me to the balls again. I threw my head back and moaned, finally experiencing the full effect of a prostrate massage, and knowing that I would never be the same. I could sense the grin on his face as he whispered to me, I told you so, and I just lost myself to the sensation.

My cock was so hard at this point that it was beginning to hurt, so I reached for it, to try and remedy the situation.

My hand encountered the large wet spot on my thigh where it had been leaking a huge amount of precum while I was being fucked. I was amazed at this since it had never done that much before, only small drops appearing as I masturbated. I rubbed my cock around in it and started to stroke it again, using it as a lubricant. The smell of it was intriguing and overwhelming me though and I had to bring my hand up and taste some of it, being that this was my first time for any of this. The taste was different, but intoxicating and I found myself licking my fingers and wanting more but the stiffness of my cock drew my attention back to it and I started to stroke myself again.

Mike had picked up the pace and was starting to grunt with each thrust, rubbing my ass and pulling me onto his cock, trying to get as much of it as possible inside me. I loved it when his balls would bounce against mine and how the head of his cock felt as it slid along my intestines, massaging that special spot as he fucked my virgin ass.

I was surprised when he suddenly reached around and started to masturbate me furiously as he whispered "same time". I could actually feel his cock start to enlarge even more and I realised that he wanted us to cum at the same time. Even with a condom on, I could feel his cock start to convulse and throb in my ass and I started to ride it for all I was worth as my ass contracted and my own cock suddenly swelled in his hand exploded, shooting what felt like ropes of cum everywhere, covering my chest and neck and some even landed on my chin, which I had to wipe up with a finger and taste.

Mike made one final stroke, pushing his cock as far into me as possible and buried his head in my hair as I reached down and pulled his balls against mine and revelled in the sensation of his cock deep inside me.

We laid like that for awhile and I slowly became aware at how sticky we were with all the cum and sweat. I wiggled my ass against him and told him that I never knew that it would feel this good between two guys and he just laughed and told me to wait till next time...

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DeborahAnneDeborahAnneabout 8 years ago
That was like me and my step dad

He did me the first time I ever had a cock in my ass and was gentle just as this story was which is nice, I would love to teach a youngster the pleasure but have no one in my area that I know would like it. And would love to have someone fuck my cute little butt someday soon. Northeast Indiana da.cd@frontier.com

ShadowWalker1600ShadowWalker1600about 8 years ago
Very Hot!!!

This is one of the best short stories I've read in awhile. Very Very Hot!! Please keep writing & posting here.

AnonymousAnonymousalmost 9 years ago

Great story.....so far ;) please keep going

AnonymousAnonymousalmost 9 years ago
Fantastic!!!

Believe it or not, my first was with a BBC. He was 16 and I 12. He just told me what to do and I did it. It seemed a blur then, and it only happened once with him. I blew him, and then he fucked me face down. I happened in the dugout of a little league field. I have been hooked on BBC since. More stories!!!

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