My Best Friends Loves Anal?

[HandyChef]

My first story. Be Gentle. lol. True Story.

One of my best friends, Jake, was as straight as they come...or so I though. We have been friends since freshman year of High School. We are both now 22. I'm openly bi to most of my friends. I always assumed Jake was straight. He never gave me any gardar vibes. He was never "Over the top Straight" Like "Bitches, Pussy, Tits, Ass All Day!" Because those types of people are who usually end up being closeted gays. So I always just assumed he was straight so I never made any hints and anything toward him. All thought, I was always physically attracted to him, I never made any moves because I respected his straight-ness and him as a friends and I wouldn't want to screw that up. So I kept my distance in the affection department...until liquid courage came along one night...

A couple friends and I went out one night. Our favorite local musician was playing at a bar downtown. Well, you know, the shots start flying, and before you know it, we are hammered. I hadn't seen Jake in a while. He had been away for 6 months for work. Jake and I go into the bathroom to take a piss. We're standing next to each other pissing, I'm done and zip up, he is taking an extra long time to "Shake it" and kinda pointing it toward me. He is really wanting me to notice his cock. I said "Looks like you need some help with that". He was like "Maybe", then smiled at me.

So we get back up to our table. Our other friend that came with us was off dancing with some random girl. I forget how but Jake and I got on the topic of sex. After a while he said "I have somewhat of a confession. I love Anal." I just automatically assume he was talking about giving anal, to chicks. Then I was like "Ok, cool, You like fucking girls in the ass. That's cool." He violently shook his head "No". I said "You like giving anal to guys?" He shook his head no again. I'm dumbfounded because I cannot not imagine him liking to receive anal. I found it hard to bring myself to say it..."You like getting fucked in the ass?" He leaned over real close and said "You would not believe the things I have shoved up my ass". Of course I ask if he had ever been with another guy and he hadn't. He had just used things around the house. Even admitted to using a full size MagLite Flashlight.

I Was Shocked! I could not believe, my best friend, who I have always been attracted to just dropped this kind of bomb on me. Right after our conversation, he said, "I'm really going to regret telling you that tomorrow." I said "Well, then I'll give myself something to be embarrassed about too, so you're not the only one. Jake, I have always liked you. Like, Like you, like you." There is was. I had said it. It was out there. I didn't know how he was going to process this information. If he was upset by what I said, I could only hope that he would forget it by tomorrow due to our state of inebriation. I has almost cringing wondering what he was going to say next. "I like you too" were the next words out of his mouth. I was relieved. "I've always though we had a lot in common" he said. He told me that he had never had a dick in him and he wanted to try it. I said "Hey, lets get out of here and go have some fun" with a wink.

As we passed the bar, we had two more shots. We stood outside the bar for a few minutes to catch some air. Now, when Jake gets drunk, its not a gradual thing. It's like someone flips a switch and he's done for. Well, as we were standing outside, that switch was flipped. A lot of puking ensued and my night came to a screeching halt. My only hope was that he remembered our conversation when he was sober, and we might get to fool around some other time.

The next day, I text him and ask him how he was feeling. We chatted for a bit, I said "Oh BTW ur secret is safe with me. I hope mine is safe with u as well." He text back "It really is safe because I don't remember what it was." .........


Next chapter: A Steamy Night At The Hotel.

Hope you enjoyed!
HandyChef

[traderjoe]

Hot story. Looking forward to the next chapter.

[Autolycus]

Welcome to the story board and thanks for a teaser of a first episode - next chapter eagerly awaited!

[HandyChef]

Thanks for the feedback guys!
Reminder: This is my first story and it is true.

Steamy Night At The Hotel

One Saturday night, Jake, Nick and I took a trip to Louisville, KY to go to a local haunted attraction. Our tour got over about midnight. We decided to hit up 4th Street Live. For those of you who have not been to Louisville, KY, 4th Street Live is a whole block of bars and night clubs. The whole block has a roof over it, there are beer gardens, live entertainment, etc... Its a cool place. We were going to bar hop and have one drink at every bar. We stopped at the second bar, lol. Ended up staying there until 3:00AM!

We took a cab back to our hotel. Stumbled up to the room. We sat and chilled for a while. Watched Tv. Boring. Nick had the idea to play strip poker. Not sure where that idea came from, but I was all for it! We ended up raiding the mini bar, playing several rounds of poker. By the time it was over, we were all naked and even more drunk than before.

Nick went to the bathroom. Jake finally ask the question I had been waiting for..."Hey. I have to ask. What was the secret? That I told you the other night?" My heart was racing. "You don't remember at all?" I ask. "No, I promise" he slurred. "You love anal." For some reason, I had a hard time saying that sentence. He just looked at me and said, "That is true." Of course Nick came out of the bathroom and our conversation ended.

We sat around for a bit, still naked, talking about our night. It was about 5:00AM. I stood up and said well, I'm going to go shower before bed. I stepped in the bathroom and turned the shower on. I knew this was my change. My stomach was churning trying to bring myself to say one sentence. I stepped around the corner of the bathroom door and said "Anyone care to join me?" Jake looked like he was thinking. "What happens in the hotel, stays in the hotel, right?" as he was standing up and walking to the bathroom. I was ecstatic!

We step into the bathroom. I shut and lock the door. We get into the steamy shower. This was a very nice hotel with a very large shower. It was the perfect setting. We are both standing there soaping ourselves up. Now, to set the scene, this was a very awkward moment. If you can imagine two drunk guys, standing together in a shower, soaping ourselves up, in silence. Like I said, awkward. lol. Neither of us wanted to make the first move. He had never done a single thing with a guy. I wasn't sure if he was still sure about trying things out and I didn't want to be pushy. Finally he says, "I meant what I said about loving anal. That's one of the reasons I wanted to join you in the shower" I said "That's cool and I meant what I said when I said I really like you." He winked at me. Something hit me. "Shit Jake, We don't have lube." He said "I saw some lotion on the counter!" So, we used a little hotel bottle of lotion. I know, I know, Not a good idea, but it was all we had. What was funny, is that it smelled like Fruit Loops.

So I reach out and grab the bottle of lotion. Squirt some into my hand and start lubing up my cock. Working it to get it hard. It didn't take me long. I put some more lotion on my hand and get ready to lube up Jake's asshole. All of the sudden, Nick starts pounding on the door. "I HAVE TO PISS!" Ugh! So I reach out and unlock door. He rushes in "Sorry. Sorry. Sorry." So Jake and I are just standing there, quiet. Me with a raging hard on. lol. Nick finished up and gets out. I lock the door again. The moment I had been fantasizing about since I became friends with Jake in High School, was about to happen...

The coast was clear. Jake bent over and spread his ass for me. Perfect ass of course. His asshole was puckering in anticipation. I think he was excited as I was. I was rubbing the lotion all over his asshole. I found it hard to bring myself to penetrate him with my fingers. I guess because I still thought of Jake as straight and found it hard to believe someone I thought was so straight would enjoy anal pleasure. It felt wrong. But deep down, I knew he was ready. I cautiously slid one finger in. He didn't flinch or pull away. He arched his back and grabbed his decently sized dick and started beating away. I fingered him a little bit. Moved up to two fingers, then eventually three with out any problem or resistance. Jake was enjoying it very much. Thrusting his hips every time I slid my fingers in and out. I started rubbing his prostate. That's when he started moaning. This really got me horny.

I knew it was time. I was finally going to fuck Jake. Now, I am considerably taller than Jake. This posed a problem. We couldn't quite get positioned right in the shower. So, I stepped out of the shower and sat on the toilet lid. (I know, classy right? lol) I motioned to my cock. Jake stepped out, dried off a bit and walked over to me. I turned him around a fingered his ass a couple times to make sure it was good and lubed. I grabbed his hips pulled him closer, and slowly lowered him onto my lap. As I entered him, he let out a small moan. I was all the in. At that point, Jake took over. He knew what to do. Slowly riding my cock at first. In and out. He finally got going. Riding my cock like it owed him money. It was unbelievable. I never knew he had such a wild side. Finally I couldn't take it anymore. I whispered, "I'm going to cum." He leaned back, kissed me and said "Go for it". I couldn't believe it. Not only did I fuck Jake, but he kissed me and is going to let me blow my massive load into his hot ass for the first time.

The kiss did it. He stopped. I pulled him close to me. Got as deep in him as I could and let it go. He moaned as I shot my hot load deep into his ass. After I came, I just kept him there. I reached around and started jacking him off. It didn't take long he shot a massive load onto the bathroom floor.

He stood up. We kissed again. He said "That was fun. We need to do it again sometime." We got back in the shower, which had been running this whole time, lol, and actually showered this time.

Nick was already asleep. We went to bed and that was that.

_____


Next story - Steamy night in another hotel with a dildo this time.
Things always seem to happen when we are in hotels. lol I don't know why.
Let me know what you think!
HC

[rickbell19]

Great story! Wish you had videos to go with it!! Can't wait for the next chapter!

[72-Jay]

A Totally Hot Story
Thanks for posting

[mbamike]

Great story! Tell us more!

[Rickrock]

Wow, I enjoyed that.