I turned eighteen over the summer as I finally graduated high school this year and decided that now that I'm not surrounded by all the high school gay bashing bs that goes on, I was going to experiment with what's out there. I've always had little inklings about other guys but never attempted anything because of the abuse gay guys get in hs. I dated girls and made out and stuff like that and enjoyed the flirting girls did with me, being a high school baseball "star" over the past couple of years. But I had lots of fantasies of me with one or two of the other players on my team over the years. Seeing some of those asses in those tight baseball pants was mmmmmmm.

So before I headed off to Texas for college this fall I decided to try my luck at trying to get some kind of experience with a guy before I try to conquer some more experienced college guy this fall. So I put an add in a popular site out there (lets say Craig) and in it I put that I would like to meet in a public place with someone first around my age and see where it goes from there. Almost instantly I get an email from this poster who said he was my age and his stats were similar to mine (5'11" 165lb brown/blue and cut). Since I refused to send a pic to him (I didn't want my pic out there on a site advertising men4men) he didn't send me one but said we could meet in person and see what happens. So I told him there is this coffee shop by the strip mall by my house and he said he knew where it was and he would meet me there at 9:00 that night. He said he'd be wearing a blue Badger sweatshirt and I told him that I would be wearing a plain yellow sweatshirt. We didn't exchange names or anything else.

First off, The Badgers is our hs mascot. So I figured out that this guy either is in my graduating class or one year before or after me. I started thinking about all the guys this could possibly be from my school. I know this is a bullshit move but I didn't wear the yellow sweatshirt. I figured I would see who walked in at 9 with the blue shirt on and I would know who he was. At that point I could either make a move or not.

As the night came I showered and as hard as it was, I didn't jack off in the shower like I usually do. I dressed and headed out to the coffee shop a little early. There was a little group of people from my school there. I got a coffee and grabbed a newspaper and sat down facing the door. They asked if I wanted to join them but I said no. Everytime the door to the shop opened I looked up for that blue Badger sweatshirt nervously knowing that I couldn't wave 'him' over because there were people from my school there. It was a minute or so past nine and still nothing. Then the guys from my school started heading out the door heading to movie and I nodded as they left, almost thankful that they were gone. Now I'm starting to get more and more nervous and anxious and I would jerk my head up everytime the bell on the front door to coffee shop would open. 9:05, nothing. 9:10, nothing. 9:15, nothing.

I finished my coffee and concluded that I got stood up. It was already twenty after nine. Just as I was about to leave I feel this tap on my shoulder. I turn back and there stood Jake. "Thought you said you'd be wearing a yellow sweatshirt."

I mumbled out "What?"

He said "Damn dude I never would have thought it was you."

My face got beat red with embarassment. He was sitting with the rest of those guys earlier and I never noticed that he never left when they did. Apparently he stayed sitting in the back of the shop waiting. He said later that he figured it was me he was meeting by my looking up everytime the door opened. Jake was one of those gl dudes on my team whose ass I had admired all year. Wow. What a shock. I was stunned.

He asked how many times I've done this and I told him this was my first. "Sure," he said. "No really it's my first." He said "it's cool, it's my first time too."

He suggested we go sit at the very back of the shop so we did. I asked him if he was gay and he said he wasn't really sure what that meant. He said he might be bi. He asked about me and I told him that although I'd never done anything with a guy that I think I'm bi too but I wasn't really sure. He said if he would have known about me he would have tried this earlier. I said yeah me too. "So what do you want to do now," he asks. I just shrug my shoulders. I asked if he wanted to go somewhere else and he said he got dropped off. I told him I could drive him back to my place since it was close or we could just hang out in my car and listen to some tunes or something. He said that was cool.

So we ended up driving to my house and sat in my car in the driveway listing to music. Both of us were very nervous as our voices began to shake when we talked. I leaned in to change out the CD and he started to rub the back of my head. He kept it there when I leaned back so I put my hand on his leg. I rubbed his leg and made my way up toward his cock. His cock was hard and buldging in his pants. I rubbed my hand over it and he let out a moan. He started to run his hand over my cock and we sat there feeling each other's cocks. I told him that we should head to my room. Fortunately no one was home but I locked my bedroom door anyway. He sat on the bed as I turned on some tunes. When I turned around he had already removed his shirt and was kicking off his shoes. So not knowing what to do next I took off my shirt and shoes. When he saw this he stood up and started taking off his pants. So I did the same.

We're both standing there with just our underware and socks on. Both with buldging cocks. I said, "well, here goes nothing" and I pulled off my underware and just let my cock spring out. Then I pulled off my socks and stood there naked as the day I was born. He looked at my cock and just said "wow, nice one dude." I said "your turn." He faced away from me and teasingly slowly pulled down his underware. He had the perfect white hairless ass. When his undeware got to his knees he bent over and continued to slowly lower them. I almost came right then when his ass cheeks opened slightly and exposed his pink little asshole. I moved in closer as he then took his socks off.

We moved closer in. At about the same time I grabbed his cock and he mine. We put our heads on each other's shoulder and I put my other hand on his bare hip. He reached down and cupped my balls. "That feels so good" I manage to say. He whispers "your balls are as nice as your dick." I smile.

We continued to stand there feeling each other. I too rubbed his balls and at one point or another we each managed to reach around and feel each other's asses. He smelt so good from probably showering not too long ago and his cologne was nice. As I'm feeing every inch of his cock I manage to squeeze out a little precum. With my thumb I gently rub it around the head of his cock. He puts his hands on my shoulders and starts to push downward. Without resisting I go down on my knees. I slowly open my mouth and put my lips around the head of his cock. I slowly go back and forth over just the head of his young cock. He grabs the back of my hair and starts pushing farther and farther until my lips begin to slide up and down the shaft of his cock. It starts to become easier for me so I grip his cock tighter with my lips.

At one point the head of his cock touches my tongue and the taste of his precum was unexpected. I pull back. I let the salty taste sink in. Thinking to myself that it was all that bad I reach for his cock and guide it back into my mouth. We got into rythym of my mouth and his hips moving back and forth. He again grabs the back of my hair and pulls his cock out and grabs it with his other hand. Then he pulls my face in and puts his balls to my lips. It all smelled so clean. So I just opened up and swallowed his balls. Or tried to. "Easy" he says.

He backs up and I stand up. He points to my bed. I lay down and he crawls up my legs to my cock. He grabs my cock, takes a deep breath and starts to blow me. I'd never felt anything like that. Not even my best jack off was better than this. He starts tickling my balls as he's blowing me and this is blowing my mind. "I think I'm going to cum" I tell him. He keeps blowing me. As I start to pant faster and faster he pulls his mouth off of me and starts jacking me while still tickling my balls. I hold my breath and start cuming all over my chest, stomach and over his hand and down my cock. I think my eyes rolled back in my head. He squeezed every last drop out of me. It was amazing to see my cum all over Jake's hand and there was a lot of it.

"Roll over," he says. "I want to kiss that sweet ass of yours." I felt exhausted like I'd ran a marathon. I roll over and he gets between my legs and spreads them out. I'm resting my head on my pillow in la la land as he begins to lick and kiss my ass cheeks. He squeezes them over and over. "Nice fucking ass too."

It's all amazing. As he has my legs spread he says, "don't move." I'm laying there with my eyes closed feeling great. Then I feel his body on top of me. I feel the hardness of his cock hitting my legs and the bottom of my ass. "What are you doing Jake?" "Don't worry," he says, "you'll like this even more." He puts his cock in between my ass cheeks and starts moving up and down. "I'm not into ass fucking dude," I tell him. "Don't worry," he says, "I'm not going to go inside you I'm just riding on top." He starts riding me and it felt great. A few time he would stop and lean up and I would reach back and stroke his cock with my hand then back to running his cock in my cheeks. This goes on for what seemed like eternity. As this his happening, my cock starts to go hard again. "Dude I'm getting hard again," I tell him.

He kneels up and I do to still facing away from him. He reaches around and starts to stroke me, his dick poking my ass. "Okay," I say. "Okay what?" "You want to fuck my ass right?" "Really?" "Just go slow."

I lean forward with my ass in the air and I spread my cheeks. He takes his precum and rubs in around the head of his cock and puts in at the hole in my ass. I look sideways and watch in the mirror on my closet door, Jake behind me naked and hard and starting to put his dick in my ass. I wish I could've taken a picture. I take a very deep breath as I feel the head of his cock start to open my virgin hole. "You okay" he asks. I shake my head yes. Over the next four or five minutes my highschool baseball buddy is pushing his cock in my ass. Back and forth. "You have smooth hands," I say as I feel them tightly gripping my hip. He says "oh yeah how's this and he slaps my ass." "OUCH!" "Shut up and take it like a man."

I could see in the mirror he loves my ass. It hurt I'm not going to lie but not as bad as I thought or as I've heard it would. Once he got into a rythym I closed my eyes and let my friend ride me. He started going faster and pushing farther in and I starting moaning because it was starting to hurt every time he pushed his cock all the way in. We both let out a yell as he pushed all the way in (which hurt me) and he came at the same time. His rythym slowed as he moved back and forth. "Easy" I say. He then slowly pulls out as I reach back and feel my sore ass. He leans down and kisses my ass once more. "Damn that's a nice ass."

Then like nothing happened we both dress. A messy cum mess all over and the smell of boy cum on both of us. "When you leaving for Texas?" "Tuesday." "Let's keep in touch and whenever you're back in town, we'll do coffee," he says. I smile and then nod. "Definately."

I had to stay in Texas over Christmas break but I'm coming back home tonight for New Years. Jake is planning on coming over tomorrow and we're going to bring in the New Year together. I can't wait.

Comments

Anonymous

by Anonymous

That sounds hot, Bud! When I first went bi I was just swapping blowjobs with a couple of guys I hooked up with. After a few months I gave up the ass for the first time. It was painful but I enjoyed how the guy got into it. It was a year before I did it again. Again it was painful but not so much. A few weeks ago I did it again with a soldier stationed at the base here.

He said he has been getting curious guys to crossover into actually trying it for years. He knows all about fucking newbies. He tried his technique with me and it was spectacular! I'll explain it and maybe you can see if it helps you. What he does is he gets all lubed up, then he starts the insertion. Once the head is in he works it back and forth a little then pulls out, lubes some more, then inserts again. The second insertion is relatively painless. He goes in halfway and works it, pulls out, lubes, reinserts and then goes in all the way. He can really go to town now. Even when he already has it all the way in, he pulls out and reinserts several times.

(0)  (0)
Anonymous

by Anonymous

This is total fantasy.

(0)  (0)
Anonymous

by Anonymous

Any story where somebody uses the word "Dude" is clearly fantasy.

(0)  (0)
Anonymous

by Anonymous

my first time going all the way was when I was 34 and he was 40, he was gentile and pulled my panties down laid me down on my back and gave the best bj and then lubed me up and then himself, got my legs up and it felt liked an hour but really about five min.,then he said this maybe a little pain and it took my breath away. then I looked at him and we were making passionate love and then felt his cock getting thicker and then I squeezed it with my manpussy and felt his hot love juice deep inside me LOVE THAT FEELING

(0)  (0)

Comment this

Can't read the image? Click here to refresh