My Best Friend

Story Info
A typical day between two friends turns into something more.
2.7k words
4.41
166.3k
73
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
matt_1972
matt_1972
31 Followers

Ian and I had been classmates since we were in kindergarten. Ian had always been a great friend of mine and now that we were both 18 and about to enter different colleges, we were spending as much time as we could together. It was summer time and Ian lived about a 40 minute drive from my house, so on some occasions, I would end up sleeping over.

That summer we did the usual: going to the beach; hiking; bike riding; whatever would get us outside and active. Ian had always been an amazing athlete; he was our school's starting quarterback and he loved to mountain bike ride. I was also very much into sports and loved the competitive nature that we brought out in each other.

Ian and I had always been into girls with each of us dating different (or sometimes the same) girls during junior high. Our times spent together were always as platonic friends that simply shared similar interests. However, there was one evening our last summer together where everything changed, and for the better.

Ian and I had just spent the day on an extremely long bike ride and we were back at his house cooling down. His parents were out with friends for the night and we decided to take a quick swim in the pool. The water felt amazing and was really doing the trick. After awhile we decided to end our swim with a quick Jacuzzi. As the jets caressed our bodies and we relaxed even more, Ian broke the silence by telling me that when he was alone, he sometimes enjoyed taking his shorts off and letting the Jacuzzi jet blast against his cock. A little taken back by what I was hearing, Ian went on to tell me that it felt amazing and that the rush from the Jacuzzi jet would make his cock hard as a rock and he would easily orgasm without having to even touch himself. Not even really knowing how to respond, he then asked if I was ok with him taking off his shorts and letting the Jacuzzi jet do its trick and that if I wanted to I could do the same.

Not wanting to make things anymore uncomfortable I replied that I had no problem with that and that I would think about doing the same. Having said this, Ian then reached down under the water and I watched as his hands resurfaced holding his wet shorts. I could see through the bubbles and water a blurry, distorted view of his cock and dark pubic hair. What surprised me most wasn't that my friend was now sitting naked across from me in the Jacuzzi; it was the sudden excitement that I felt at the sight of him being nude and us being alone together.

Now I had seen Ian nude many times. We had played sports together for the last 6 years through middle school and high school. Ian always had in my mind a really nice body and a well endowed cock. I had noticed Ian's transformation over the years, from puberty into young adulthood, and I must admit that I couldn't overlook the fact that Ian had developed a pretty big and thick dick with a subtle amount of dark pubic hair (which by the way did not match his sandy blond hair). This image of his cock was now in my mind and knowing that he was nude and only a few feet from me in the hot tub was all of a sudden causing my own cock to stir to life. Pretty soon I decided what the hell and removed my own shorts and set them along side the edge of the Jacuzzi. Ian gave me a quick smile and a nod and then closed his eyes and lay back with a look of satisfaction on his face. I in turn laid back and guided my now slightly engorged cock over to the Jacuzzi jet right next to me.

Well I have to say that Ian was right, the feeling of the jet blasting against my stiffening shaft felt amazing. I would slowly lift myself up and down to allow the jet to blast against my thick cock. Slowly my cock grew harder and harder and I lay back with my eyes closed just feeling the pleasure mounting between my legs. Pretty soon I could sense myself getting close to climax and I looked over and Ian was watching me with a bit of a devilish smile on his face. As I came I sensed that Ian was doing the same and the thought of us climaxing together was exhilarating.

Pretty soon Ian jumped out of the Jacuzzi and went over to the wall and grabbed a towel. As he walked, I blatantly stared at his now flaccid (but still enlarged) cock dangling between his glistening wet legs. I was amazed at how big Ian was. I realized that when ever I saw him nude in the lockers at school, it was when he was completely un-aroused, but now, having just had a raging hard on, his cock was at least 8 inches in length and thick as a brick.

Ian grabbed an extra towel and turned back to the Jacuzzi. Realizing that he may have noticed me staring at his cock I looked away and acted like everything was normal. Ian slowly came over and sat down along the edge of the Jacuzzi facing me. He brazenly left his towel at his side

"Pretty nice, huh?" Ian asked.

"What do you mean? Oh, yeah, that felt really good" I stammered in reply.

"What did you think I was referring to?" Ian asked coyly.

"Oh nothing; I...I don't know, for some reason I thought you were talking about how you looked. Sorry."

"You mean my body? I do look pretty good, don't I?" he laughed, "although, I have to say I am a little self conscious of some of my features."

"Which ones? Trust me; you don't have anything to be self conscious about. If anything, I have a few that I would rather change if I could."

Ian looked down at himself and said, "Well, I am a little embarrassed to talk about it, but I do wish that I had a slightly bigger penis." As he said this he reached down and picked up his flaccid cock in his hand and dropped it across his thigh with an audible slap

"Are you kidding me, you're cock is perfect! I would love to have your cock!" Realizing what I had just said I quickly backtracked stating "Sorry; you know what I meant to say. I didn't mean that I actually wanted your cock. You know; in that sort of way."

"No, I don't know what you mean." Ian replied, now looking me straight in the eye with a slightly wicked grin. "Is there something wrong with wanting my cock?"

My heart was racing, "No, there's nothing wrong with wanting your cock. I just didn't want you to get the wrong idea or get angry at me."

"Matt, I would never be angry with you about anything...and when it comes to the debate of who has a nicer penis, I think you take the cake on that easy."

"Uh, thanks man" I stumbled nervously "but I just saw you, and I definitely think your cock is bigger than mine."

"Ahh, so you were checking me out!" he laughed, "I may be a little bigger Matt, but I sure wish my cock was as thick as yours. You have a friggen coke can dangling between your legs!"

"Yours is pretty damn thick Ian." I could feel myself becoming more and more comfortable with this line of conversation and I slowly started to look more and more at Ian's beautiful cock resting against his thigh as we talked. And as I did I could feel myself starting to become aroused again.

Ian made the first move, "I have an idea...why don't we measure our cocks and put this debate to the test."

"Do you have measuring tape?" I asked as I slowly started to stand up and move over to the edge of the Jacuzzi that Ian was sitting on, not even realizing that my now hard cock was pressed against my lower stomach and poking above the water line.

"Who needs measuring tape?" Ian asked looking down at my cock smiling. He hopped down from the edge of the Jacuzzi and landed right in front of me, and before I could react, he reached down and pulled my rock hard cock away from my stomach and guided my cock over to his and with his other hand laid his still flaccid cock on top of mine. A rush of electricity swept through me. I could not believe that this was happening and how much I wanted it to. Seeing Ian's beautiful cock resting on top of mine and the amazing feeling of it was sending me into delirium. And as I stared, his cock began to twitch and grow bigger.

"Uh, wow, it looks like your preparing yourself for the measurement" I sputtered.

"I think the feeling of your thick cock under mine is making me hard, Matt." Ian responded softly, "does that bother you Matt?"

"No Ian, this feels so good. Your cock is making me so fucking horny" I whispered as I forced myself to look up from the sight of our now hard cocks resting together. Our eyes met and Ian whispered, "I know, me too" and as he did he leaned in and gave me a deep and passionate kiss. My knees buckled as our tongues met, and he pulled me close to him. I could feel his muscular body against mine, his strong arms holding me tight while our cocks pressed and rubbed against each other, the precum leaking out and creating our own self made lubrication. We continued to slowly grind our cocks against each other as we kissed, making out like I had never made out with anyone before. As we kissed, I slowly started to guide Ian back to the edge of the Jacuzzi. This being my first time with a guy I was extremely eager to taste his big thick penis. I wanted to finally know the feeling of what another man's cock felt like in my mouth and I was so happy that Ian was going to be that man. Once we were by the edge of the Jacuzzi I pressed him back against the wall and slowly started to kiss my way down his body as my left hand lightly caressed his chest and nipples and my right hand started to fondle the base of his cock and his large set of balls. As I did Ian hopped up onto the edge of the Jacuzzi putting his huge cock right in front of my face. With both hands sliding up his muscular thighs I guided my face into his thick glistening hard on. I was like a child with his first popsicle, slowly licking the underside of his cock, feeling his large urethra vein as I slowly made my way up to his thick, chiseled mushroom head, which was dripping with precum. I had now taken the base of his cock in my left hand and was caressing his balls in my right as I kept exploring his cock with my tongue, telling him how big he was and how much he deserved to be serviced like the stud he was. Ian's groans were getting louder, encouraging me that I was doing the right thing, and I slowly worked my tongue up to his cock head and started to work my way around the head, licking the precum up like it was honey. As I did Ian reached down and took my head in his hands and pulled my eager mouth onto his huge cock and as he did I relaxed my jaw and throat to allow his engorged manhood to enter me.

The feeling of his penis entering my mouth was amazing; he was so big and hard at this point and yet so soft and perfect. Ian was now completely inside my mouth, pushing his huge cock deeper and deeper with each gentle thrust and as he did I reached around to pull his ass closer, forcing him deeper into my mouth. Eventually, he was all the way in and his huge cock head was pressed against the back of my throat and his soft, yet still wet pubic hair tickled my nostrils as I breathed through my nose, trying with all my might not to gag on his fat meat stick. The smell of him flooded through me and sent me into oblivion. I was literally becoming inebriated with the taste and smell of Ian's huge cock; I had never wanted anything more than this I realized. As Ian continued to fuck my mouth I looked up at him and saw him staring at me with his beautiful eyes and it was then that I knew I wanted Ian to fuck me and I slowly pulled his cock out of my mouth and told him as much.

With that, Ian pulled me up and kissed me again, the tips of our cocks touching and rubbing slightly against each other. "First, let me taste that big, thick penis of yours Matt" was Ian's response. I smiled and switched places with him and as I did I took the towel that he had grabbed earlier and laid it out along the edge of the Jacuzzi. I then hopped up and sat on the towel and leaned back as Ian moved forward and lowered his beautiful face onto my fat, dripping cock. Ian was so gentle, yet confident in how he serviced my big dick that I almost came immediately and was convinced that he must have done this before. He worked my meat pole like a pro and then after spitting into his hand, he started to stroke me as he slowly licked my balls and worked his way to my tender and tight little ass. Feeling his tongue explore my eager fuck hole as he stroked my huge raging hard on was stirring me into a frenzy, and as he did I moaned that I wanted to feel him inside of me.

The next thing I knew, Ian was pulling himself out of the Jacuzzi and I watched his ripped body glisten with falling water as I slowly edged back on the towel, spreading my legs and offering myself to him as he got on his knees and began to guide his huge shaft towards my waiting hole. I quickly leaned up and slobbered some saliva on his fat cock head to lube him up even more and then laid back again, ready for the fuck of my life.

The moment he entered me was the moment I think I had waited for my entire life and had just never known it until then. Although the initial pain was a bit of a shock, his cock was so amazing, and he was so gentle and eventually the pain subsided and he pulled me close and we made love as his huge penis penetrated me deeper and deeper. Soon we were fucking hard and rhythmically and we continued to make out deep and passionately as my cock slapped back and forth against our stomachs. Pretty soon I could hear him grunting loader and he whispered in my ear that he was going to cum and with that thick white ropes of cum shot from my cock onto my chest and I could feel his cock pounding me deeper and deeper. Finally, I could feel him tense up and then time almost froze, until suddenly I felt what seemed like a gushing hose unload in my ass. Loads of cum exploded from his cock and filled my ass with his seed until cum was literally dripping out of my hole. I pulled Ian close and kissed him deeply and told him that I loved him and that I would always remember this day. He responded that he had always felt the same way and then we held each other until we finally almost fell asleep. Not wanting to have his parent's catch us we cleaned up with a quick dip in the pool and then retired to his bedroom where we held each other close until we fell asleep in each others arms.

matt_1972
matt_1972
31 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
11 Comments
Andy_gay_boyAndy_gay_boyover 1 year ago

Soo beautiful and sexy as fuck am glad you created this

AnonymousAnonymousalmost 3 years ago

hot

AnonymousAnonymousabout 8 years ago
Matt, if Ian is not your childhood friend's real name, then he is R.N. whom i met in Lugano, Switzeland

(This story: ☆☆☆☆☆)

We met in a group of English speaking people. We hit off right away and became friends.

To cut the long story short, he popped my ass cherry. His dick was impressive! His seduction method was to be himself. He first took out his almost erect cock. He was not offensive but he asked me to see my dick in a very relaxed manner as though he was asking me to show him the sport sox that i just bought!

He first kissed my dick very, very gently. He licked the edhes of its head. I was already his! I started to accept & return his French kisses... & ask for more.

Than he caressed the root of my dick between my balls & my asshole. Then he started to kiss the same area & moved to my ass: he started with my butt cheeks, but his target was my cherry hole. He was eating my ass...

Afterwards i placed my face on his chest, & was caressing his upper body. I expected to be shy, ashamed and uncomfortable. I was not. Everything was clear: it was obvious what 2 consenting adults did & that they liked it.

I was French kissing him every now and then & he was kissing me back.

All i said was: "I enjoyed this very much... No regrets. I am glad you made the move... I hope we will stay friends... I will not say 'No' to you..."

AnonymousAnonymousover 8 years ago
Very Thoughtful

I am amazed at your being able to capture this moment in words. Also very sexy. I'm kinda horny now, thanks.

AnonymousAnonymousalmost 10 years ago

My friend Graeme and I had lived near each other for 18 years, we both moved after high school, me to uni, he travelled. We saw each other when he came back, played squash, had a bit to eat. He always had girls around him, at squash I could see why, in the showers, he had a much bigger cock than I did and I thought I was o.k. Then 11 years went by, I married and separated, he called by chance, he was coming back to town for 2 days, I said stay over. We played squash, we were both still fit, had a meal, then a few drinks back at home. We talked, about my marriage, he said he didnt have a permanent relationship, I said yes you didn't have trouble getting girls, I wasn't so lucky, I even thought about guys. He looked at me, nothing wrong with that, I have.I laughed, sure, he said no guys are great, they just want sex and I can give them that, they give great blowjobs or more. My cock started to tingle,really, well I might have to try soon, with my luck. He looked at me, what about now, come on, we know each other,i don't know, look give it a go, no one will know and he stood and took his shorts off. Come on, get them off, I stood, he said I can see you want to, I did, my cock sprang out. Hmmm as he moved over, reaching for my cock, his hand gripping and stroking it, and without saying a word knelt down and took me in his mouth, ohh fuck he was good, better than my wife, I told him shit, im going to cumm and he touched my balls and as my cumm shot out he pulled me to him as I had the most intense orgasm, until I was weak at my knees. He pulled back, wow, you sure needed that. He stood up, his cock looked huge, I looked at him, touch it, I reached out, stroked him, so hard, I felt so horny, you can suck it if you want, I knelt and took just the head in my mouth, a slightly salty taste, he moved forward,i gagged, I couldn't take it all, sorry, don't be. Lets lie down, I lay on my back, he moved over me his cock at my mouth, I again tried but I kept gagging. He got up, came back and said I see your cock is ready again and I felt his hand apply lube to my cock and rub up and down, I was hard and I felt his fingers rim my hole, then one pushed in as he stroked me. It was too much, my cumm arced into the air, after already cumming once I was surprised. You like that, yes, well lets see if you can take me this way as I felt his finger moving in my hole. I don't think so, ever do this with your wife, a couple of times, well she could take it, as he removed his finger and lifted my legs, most women and guys I do this too end up loving it. I felt a greasy finger at my hole, then something much larger, his cock as he opened me with 2 fingers followed by the head of his cock, he removed the fingers and slowly pushed forward, aagh pain as he eased in past the first muscle and my hole closed around his cock. whoa, tight as, relax, I cant, yes you can try to push me out, I did and I felt him slide further into me,then ease back, push I did and he went in further, I felt him pulse and I was filled with warmth, aagh you made me cumm your so tight and he eased back and pushed forward, he went in easier, that's it, until I felt his hairs against my butt. My cock was standing up,i felt full,uncomfortable but, I wanted him to fuck me, I pushed towards him, cumm dribbled from my cock, oh shit, as my insides seemed to quiver, wow, what are you doing that feels great he said as my insides caressed his cock and then he began to fuck me, I think I blacked out a couple of times as he drilled me, my cock just would not go down, I touched my cock, stroking it, milking his cock with my insides as he went faster, telling me what a great fuck I was as he filled me for a second time.We lay there, I felt him shrinking and he moved away, it hurt when he came out, we lay there, I had to go to the bathroom, cumm blobbed out of my still partially open hole. I lay back down, thinking about what had just happened. It changed my life, I still fuck women when I get the chance but more of my time is spent on my knees or on my back with a hard cock fucking my willing arse.

Show More
Share this Story

Similar Stories

First Time with My Best Friend Straight married man is seduced by his best friend.in Gay Male
We're Not Gay Two guys discover their orientation isn't what they thought.in Gay Male
Boyfriend Gets It in the End She convinces boyfriend to try out his hung friend.in Gay Male
Road Trip with Mike Graduation road trip with my sexy friend takes a turn.in Gay Male
My Best Friend The Football Star Love blossoms when best friends learn a new way to score.in Gay Male
More Stories