Probably a little too perfect for a first time but what the hell. It's fantasy, right?
I'd fantasized about being with a guy for most of my life. I don't really know why. I'd watch porn and wonder what it would be like to be the girl. Okay, not really wonder. I flat out wished I was her. Wrapping my hands around his hard cock. Stroking it. Maybe even sucking on it. Feeling his shaft sliding across my lips. Tasting his precum. Wondering what it would be like when he finally came and if I would like it as much as I thought I would. Or if I would just be grossed out.
Eventually, my fantasied lead me to Craigslist where I would browse the Men Seeking Men listings just to see what was out there. I actually considered messaging a few of the guys but could never work up the courage. The main reason, or maybe it was just an excuse, was because I live in a pretty small town and didn't want to run the risk of either hooking up with someone I knew or getting recognized by him later.
Eventually I got bored with the whole Craigslist fantasy and pretty much went back to porn and the occasional foray into camming on Manroulette when my wife was at work.
As a lawyer I often have to go out of town to meet with clients or take depositions. Rarely was it ever very far but on this occasion I was sent out of state to take a deposition for one of my firm's clients. That night I was sitting alone in my hotel room and decided to kill some time in the time-honored way of all men: jerking off.
As I lay there amusing myself for some reason my mind wandered back to my old Craigslist fantasy days. I was kind of shocked. I was seriously considering posting an add. I think I figured nothing would really come of it. I mean, it would only be for one night. What would be the odds that someone would really see it? And be close enough to hook up? And to actually be someone I'd be interested in hooking up with anyway? What the hell, I thought. Even if someone responds it's not like I have to answer them. So I logged in and posted my ad:
HJ, maybe more - m4m
Never been with a guy but always wanted to try it. Just lay back and let me jerk you off. Maybe more if it feels right. No reciprocation required. I can host. Tonight only.
I sat back and waited to see if I would get any takers
About a half an hour later I had two. The first guy was in his 20's and as soon as he found out I was in my 40's didn't want anything to do with me. But the second one seemed pretty cool. Professional, like me, in his late 30's. Married but his wife as out of town chaperoning a high school band trip. And about 10 minutes away from my hotel.
We e-mailed back and forth for a while, discussing our expectations. He knew everything was up to me. He was in charge but I was the one in control. Meaning that I was there to please him but wouldn't be doing anything I didn't want to. Since hooking up like this was a first for both of us either of us could call it off at any time. He was about 6'2", about 200 lbs. The part I was most interested in was about 8 in. and circumcised. He said he couldn't send any pictures but that, if I decided to go through with it, I wouldn't be disappointed.
I thought it over for a few minutes, typed in the name of my motel and the room number, took a deep breath, and hit "Send".
About 15 minutes later there was a knock at my door.
"You must be Steve," he said.
"And you must be Will. Come on in."
"Uh....How do we do this? This is my first time."
"Mine too," I answered. "Why don't you just lay on the bed and let me take it from there?"
He took off his shoes then reached for his belt.
"No. Let me do that for you. In the mean time, I thought you might like something to drink."
In his e-mails he said he was a rum and Coke man so while I was waiting for him I made a quick trip to the motel bar and got him one.
"Thanks," he said, taking the glass and laying back on the bed.
"Would you like me to get naked?" I asked.
"That might be nice."
I took off my clothes and walked over to the bed. Kneeling next to him I reached out to his pants.
"Let's see what we have."
I pulled down his zipper and reached inside. He wasn't wearing any underwear so my hand immediately felt his cock. I could feel its warmth in my hand. I grasped it and pulled it out.
He wasn't hard yet but he was well on is way. His cock and a good 6 inches and thick. And heavy. I've always been more of a grower than a shower but it looked like he was a little of both. But I could tell he was having a little trouble getting hard. So could he.
"I guess it's a little shy," he said, embarrassed.
"Don't worry about it. We're not in any hurry."
I brought up the motel's porn menu on the TV then tossed him the remote.
"Why don't you find something good. And let's get you out of these."
I stood and pulled off his pants then laid back on the bed next to him. Before long I could feel him getting harder and soon Anna Bell Peaks and I both had a hard cock in our hands.
Like he said, his cock was close to 8 inches and fairly thick. I lay there next to him entranced by it. He had a couple big veins running down the side and I's delicately trace them with my finger, starting at the base, moving up to the tip, then running down the other side.
I propped my head up on my elbow as I laid next to him, stroking him and alternating between watching the porn and admiring his cock. The way it filled my hand. Its warmth. The smooth skin of his shaft sliding over the hardness beneath. It all felt so natural.
We lay there like that for about fifteen or twenty minutes. Watching porn and chatting about whatever as I stroked his cock. On the TV Anna Bell was blowing some lucky guy. I turned and looked up at Will. He was concentrating on the show so it took him a few seconds to notice me looking at him.
"What?" he asked.
"Nothing," I said. I looked at the TV then back at him. The look in my eyes told him exactly what I was thinking.
"Tell me what you'd like." I wanted to hear him say it.
He looked at me. "Suck my cock, Steve."
