Craigslist Experience #4

My first anal experience. 

Here's the Craigslist post that caught my eye.

>want my ass taken - 37 (salt lake)
> Reply to: pers-ftx9u-1XXXXX14@craigslist.org
>
>
> Been a long time since I had my ass played with. Got a gf but she's not into it and a real cock feels so much better anyways.
>
> Don't want any drawn out foreplay. We go to the bedroom, take each others clothes off, fondle, touch, maybe you turn me around
> so you can bend me over a little to have better access to my ass, get on the bed, some oral to get us hot, then you have your way with me.
> Doggy, face to face, on our sides, standing, anyway you want. Not into obese but a little hard belly to rub against me is okay as long as
> the rest of you is masc and in shape.
>
> Me: slim/athletic build, d/d free, play safe, short hair, professional looking. Need a pic eventually. Won't meet without one. <<< >

So, I respond:


> From: jack@yahoo.com
> Subject: want my ass taken - 37
>
> Did you get any takers?
>
> I'm a newbie to all of this, but lately exploring a lot. I've had 3 pretty great Craigslist BJs. Never done anything anal. I know I could never bottom, but I've been curious about topping.
>
> I've given a couple of BJs. I could use more experience.
>
> I don't have a big dick. If that's a problem, I understand.
>
> So if you'll be patient with me, and tell me what to do, I'll try stickin it to ya.
>
> 46 147lbs 5'6" Average nice guy.
>
> Jack.

So, we e-mail back and forth a couple times, and exchange pictures and all. I'm surprised he's interested because he's 9 years my junior.

He finally gives me his cell phone number, and I give him my address, and we set a time. I just have enough time to run over to the grocery store and buy some condoms and KY Jelly. Since I had never done this before, I asked him in one of our e-mails if that would be okay for Lube. It was. I purchased them at the pharmacy, and I was surprisingly calm. I thought maybe I'd have trouble with it, but I was as cool as a cucumber, as if I bought condoms and lube all of the time.....that's right, I'm a stud now.

I run home and get everything ready. Porn on the laptop, condoms and lube on the dresser. A towel standing by, just in case. I've read a couple gay sex forums, and they said it would be a good idea to have a towel standing by.  (It came in handy.)

I'm pretty nervous when he pulls up in the driveway in a nice silver car. Maybe a newer Caddy, or Acura or something. He's dressed like an draftsmen or architect or something, and looks better in his clothes than in the nude picture of himself. Actually, he looks pretty good.

So, he rings the bell, I answer, "Elton?" I ask. "Yup." he says. I'm not sure what to do next, so I say, "Well, let's go upstairs". He follows. I secretly hope he's checking out my ass on the way up.

When I get to the bedroom, he grabs for my junk, through my pants. I reciprocate. He pulls me in an kisses me right on the mouth. I'm totally surprised., but I try to get into the moment, and our tongues meet. I pulled away and said "I've never kissed a dude before." He apparently doesn't care cause, he pulls me in for another, as we feel each other up. It was kind of like making out with a chick, but I didn't have to buy dinner or anything.

So, I'm kind of getting into it, and start nuzzling his neck. I really want to suck on it, or maybe bite it. He pulls me off, "No marks...." he instructs. Okay, I'll take I'll take it down a notch.

We pull off our clothes. He's really smooth, and his dick seems to be about the same girth as mine, but certainly longer. Nice looking too. So, I start sucking it. A minute later we move to the bed. I'm not sure who's idea it is, but we 69 for a bit. It's nice.

After a while, I ask if it's time to try that other thing.

Sure.

I grab the condoms and the KY. I hand HIM the condom package. He takes out the condom and unrolls it on my dick. I wish my dick was longer, like his.

I squirt some KY on my dick, and rub it around. Elton grabs behind his knees and offers up his ass. I put more KY on my hand and rub it around his nearly hairless butt hole. It looks small. It looks really small, and my dick looks huge when I press it against his hole. I start to push but nothing happens. Reminds me of when my first girlfriend and I lost our virginity together. (difficult)

So, I did what any guy would do, I tried gently rocking it in, and sliding it up and down, but it wasn't working. I tried again to force it in his butt, and finally I said "there's no way dude!" Instead of agreeing with me, he said, "keep trying, it will go in."

Well, now the race was on. My penis hadn't had any stimulation in a few minutes, and I was starting to lose my erection. This breaking down the fortress wall stuff wasn't really turning me on. Finally something happened, and my dick entered his ass. God, it was tight, and he winced.

 "Wait......" he said.

 But waiting wasn't helping my hard on. I needed to do a little in-out, in-out, and quick, if I wanted to save my boner. I started to move back and forth slowly. It started working for a minute, but I got greedy, and pulled out too far, and my dick came out. When I went to put it back in, I noticed that things weren't pristine clean. I guess I knew sex could be messy, but I guess you don't get the whole picture until you play the game for real. And there was a little bit of smell.

Well, so I'm trying to stuff my sausage back in, and there are a couple of turn-offs happening. I think maybe this will go better with the rear entry method. I suggest it and he stands on the floor, and leans over the bed. He's just barely learning over, bracing himself with his arms. I don't know why, but I think maybe it will be easier, if he bends all the way over. Instead of suggesting this, I just push him down, like I'm some kind of porn star or something.

He gets the idea, and I go about unsuccessfully trying to gain access to the back door again. Finally, Elton says "are you hard enough?"

How embarrassing.

"Apparently not," I responded.

I wanted him to suck me some more to get me hard. That wasn't going to happen with that dirty condom on. I got it off and put it in the trash.

I can't exactly remember now if he sucked me off again or not, but we did try it again with a fresh condom. I found the same impenetrable fortress gates again, and soon my dick started to deflate.

I said "wait a minute, let me get something from the drawer." I was going to get the mail order dildo, that was way too big for me, and I was going to try to loosen up Elton's asshole. "Naw, I've got to get going. Let's just get off" he said as he stopped me.

I pulled off the second condom, and Elton took over. He was making out with me and docking our cocks. I think that's the right term. Anyway he was jacking us both off in one hand. And he was making out with me a little. It wasn't doing much for me, but it wasn't bad. Pretty soon, he says he going to cum. I hear his breathing increase, and then he makes the classic "O" face. He squirts on the towel, and a little on me. It was pretty hot I guess. It would have been hotter if I was anywhere near climaxing as well.

Oh well. He asks for the bathroom and takes the towel with him. "Is it okay to get this wet?" He yells. Of course it is. I guess he's cleaning up. He returns to the bedroom. I've already got my boxers on and he puts his shorts on as well. He can't find his pants for some reason. Finally we find them under the bed. And then he left. "Sorry we couldn't get you off" he offered as he was leaving.

Oh well, it was a first.

 It was fun.

 I'll have a better idea of what to do next time.