OMG I just lived out the archetypal fantasy of the decade. I have to share the story.
I put an ad up on Craigslist, the first time I have ever done so. I was really horny so I had to do something. Well two hours later no luck, so I had to jerk off. Well literally the second I finish I get an email. Normally I am in no mood to even thing about sex after jacking, but I decided to check.
The guy was like "Hey 28 year old here. Never done this, but I am kind of wanting to try a few things. Can't share any pics, my worst fear is that my pic will end up on a website. But my girlfriend is gone until tomorrow so I really want to get something done."
Well I didn't really believe he was straight, and I wasn't willing to meet anyone without a picture first. So I first say hey, send him a picture of me, and ask him what he wants to do. He said "Well I dunno, I want head and I guess I can try to give you some too. I'm nervous though, so I really don't know.'
At this point I am still thinking this is some troll trying to play into another gay guy's fantasy. I tell him that I would love to hook up, but have to see a picture. I assure him that I will delete it as soon as I see it (and I did, but not before saving it). Well the picture this guy sends me almost send me over the edge. It is so stereotypically straight! Blue polo shirt, miller light in one hand, and a tall, skinny blonde with big boobs in the other. Even though I think it is too good to be true I continue.
I tell him that I can host, but don't have a car. Turns out he has been drinking a bit. I call in a favor with a friend and borrow a car. At this point I still think it isn't totally legit so when I pull into the driveway I make him come out to the porch so I can see him before I get out of the car. It is real. There stands this total image of a jock. I am instantly nervous, totally wanting to play up to this guys dreams.
I walk in and we have a little small talk. He tells me that the only time he has ever been with a guy was when he was 14 and it was just experimental stuff then. This guy was totally not lying. There are a few beer cans laying around among many pictures of him and his blond girlfriend. After only a few minutes he says "Well let's get this started" and takes off his clothes. So hot! We go to the bed and I start working my oral magic

. It is somewhat funny because he can't decide what to do with his hands. As soon as he gets hard his girlfriend calls. Five minutes later I am back down below.
He then says he will try to give me head. He is amazing. No lie better than anyone I have ever had. Like I said I had just jerked off so it is very slow to get hard (and I was really nervous). He thinks it is his fault, I tell him its not. Then as soon as it gets hard he says "Do you want to fuck me?"
I almost freaked. I have never topped or bottomed, and totally wasn't expecting that. Anyway I tell him I have no experience with that, and he says "I don't care neither do I."
So I get a condom, and damn it I lost the boner. I had never put a condom on before and I got nervous. So I start giving him some more head hoping I will get it back up. He asks what happened and I said "Man, I'm nervous. I've never even done this before"
He responds "Well if you don't want to you don't have to. To be honest I'm not overly thrilled with the idea, I just wanted to make sure you got off and I felt like the head wasn't cutting it"
Straight and sweet, lol. I decided I just wasn't ready for anal yet and we get into some serious oral action. He tells me that when he comes it will be over, and he wont be able to do anything else. So we decide I'll come first. He gave me some fucking AMAZING head. I am close so I stop him. "How do you want me to cum?" I assume he would be totally against in the mouth.
"I don't care. Just let it happen" he said
So he went back to it and in no time I cum, and he doesn't pull away at first. When I finish all of a sudden he bolts out of the room. I kind of freak out thinking he is going to freak out and go crazy on me. I yell for him, and turns out he is rinsing his mouth out in the bathroom.
"I tried man, but it was just too much for me" he reasoned
I assure him it is okay, and then go back down on him. He was so fucking hung my jaws are still hurting. In no time he is cumming.
He then started laughing. A bit confused I ask him why. "Man, I dunno. I have just wanted this for so long, but always chickened out. I can't believe I actually did it."
I hang around for a bit, make sure to clean my mess and then tell him I'm about to head out. He tells me that he isn't sure, but he wants to keep my number and email in case he wants to again. I, of course, say that is fine.
Now I'm here. Sorry it was so long, I had to relive it. It was absolutely amazing. I still can't believe it happened!