Taking Ian Out

First of all, I'd like to begin explaining this experience as I remember it by telling you exactly how it came to be. See, I am and always have been a rather masculine man. You know, into sports, fast cars and that sort of thing. To say that I'm overly-caring about my fashion sense and appearence, or at all flamboyant would be quite far from the truth. So with that, my bi-sexuality was unknown to most everyone besides the men I'd fooled around with, and even if people had an idea that I was bi, they certainly had no clue as to the intensity level of which my lust for men had grown.

The problem was, I just didn't have interest in the sex available to me anymore. It had become boring and less passionate. I wanted to explore more sexual options with men, and I wanted my sexual relationship or sexual relationships to be fresh and open to new things, plus intimate and hot.

So at one point, I found a Gay Personals website that I posted my own personal ad on. I included a photo of myself, a brief description of what I liked to do and the kinds of people I was interested in, my location and first name.

Anyway, a couple days after posting up my personal ad, I recieved a private message from a local guy who was also on the site. He basically mentioned that he was interested in what I had to offer and that he found me very attractive, so he left his phone number and said to ask for Ian if I called.

I looked at his profile after reading the message and it wasn't very helpful in terms of letting me know what he was sexually into. But from what it did explain, he seemed to fit the description of what attracted me. He was 18, which was 3 years younger than I was and I liked that from the start. From the photo he provided, he looked very hot with a skater-type style. He had dark brown eyes and a lightly tanned complexion, though he was evidentally caucasian. His hair was dark and longer than mine, but still reasonably short. He had both of his ears pierced with relatively thick plastic rings, along with a pierced tongue and lower lip. Finally, his skin was very smooth looking on his face, no facial hair except his well maintained sideburns and his eyebrows were perfectly shaped.

Although I had no idea how he would turn out if I ever got the chance to fuck around with him, the boy was just plain sexy so I figured I'd call and I did that afternoon around 3PM.

I dialed the number cautiously, expecting nothing and it rang twice before a deep, yet still boyish-like voice answered.

"Hello?" said the unnamed voice. "Hi, is Ian around?" I asked in responce. "Yeah, this is Ian." He answered, "Who's this?" I wasn't sure if he'd even remembered my name from the profile, so I hesitated for a second. "Hey, Ian." I finally began, "It's Joe. You sent me your phone number in a message on the web." He was quiet for a few seconds and I was getting nervous as the silence continued. I thought I'd fill it with something so I said in embarrassment, "I don't know if you remember who I am (I force laughter). Do you?" He started to say something, but I could barely understand it before he stopped and then he began again, this time more clearly. "Sorry, Joe." He started, "I'm trying to help my sister with something." That must've been who he'd been talking to when I couldn't understand him. I laughed a bit and OK'd his delayed responce. He laughed a little too before going on again. "Ofcourse I remember you, though. How could I forget a sexy guy like you?" He giggled at his remark, but not too much as to have me thinking he was joking. He was definitely serious when he made the comment. I laughed it off though, and returned the compliment to him.

We talked for a little while. Just small chatter really, but it was very flirtacious. He wasn't obscene at all, though he was still able to get his point across about how hot he thought I was and he used little sexual inuendos to hint what kind of mood he was in. I saw that as my cue to take some action and schedule a meeting for us.

"So, are you busy tonight?" I asked in a suggestive tone. He giggled a bit as he responded. "I'll be busy waiting for you if you don't make it happen." He answered. The way he said it sent shivers down my spine and my dick began to throb. He gave me his address with some brief directions and I was to pick him up at 7:30 that night.

Six o'clock rolled around, and I started to get ready. I showered thoroughly, brushed my teeth, rinsed my mouth and trimmed my goatee. My hair was so short that nothing could really be done with it, so that was one less worry. What to wear, though? I knew I should've asked him what he planned to wear, I thought to myself. Finally I decided to wing it and I put on some black briefs, a casual but nice pair of blue jeans, a white sleeveless undershirt that was more so a tight muscle tank top and my long-sleeved white collar shirt with blue stripes, which I buttoned up a little more than half way. After applying the final touches, a clean pair of white ankle socks and some black dress boots for men, I sprayed on some nice cologne and headed out. I pocketted a pack of condoms that were in my top drawer, just in case.

On the way there, I began to fret. Anything that you can think of going wrong on a first-date, I thought of- What if I'm under-dressed? What if I'm over-dressed? What do I say when he walks out? Do I hug him? Kiss him? What if I say something wrong? Maybe I should button up my shirt more, or maybe I should unbutton it more? Where do I take him? Should I stop and get him something on the way?... and etc. I decided to let my mind go blank and try to expect nothing. Whatever happens, happens.

I arrived at his house no more than 2 minutes early. It was already dark, being that it was the middle of Fall. But the night was warm, with a nice breeze. I parked my black 1987 Chevy Monte Carlo on the side of the street, right in front of his little house and I honked twice for him. It didn't take more than some 15 seconds for his front door to open and him to emerge from the house. He walked out towards my car in a pretty quick pace, keeping his eyes locked on mine as he smiled at me.

He was dressed casually, but impressively aswell. His jeans were very faded and looked almost white, but you could tell they were made to look like that. They were tight around his slim thighs and outlined the bulge of his dick in his crotch as he walked. He wore a black leather belt with silver metal studs on it and a grey t-shirt with a skateboard brand on it that he had tucked in. The shirt complimented his build cause it was so small and tightly pressed against his torso. He stood about 5'9" tall and carried maybe 145 LBs, but he was very fit and lean for his size, with more of a swimmer's type build. I started to feel a lot more comfortable dressed the way I was, now that I knew he was wearing casual clothes too. But damn did he look sexy as hell.

I got out of the car and walked around the front of it to greet him. We hugged and exchanged hello's for a minute. I told him he looked very nice and he stood up as tall as he could to reach my cheek, which he kissed before moving his mouth close to my ear. He nibbled on it a little, with his arms entwined together behind my neck and he whispered softly in my ear, "You look even nicer, Baby." Then he tickled my ear with his tongue as he moved away.

I gave him a sexy glance and we started to the car. Before he could put his hand on the car door, I reached to it first and opened it for him. He smiled at me thankfully and began to get into my black Chevy. I watched him as he slowly started to get in and his jeans tightened up around his plump, round ass when he bent down into the car to move some papers I had on the seat. My cock started to do the thinking for me and I couldn't look away from that sweet bubble butt. I grabbed it gently and squeezed on it hard as I rubbed my crotch into his backside. He giggled and pushed himself back against me, massaging my dick through my jeans with his clothed ass and then got into the car.

I walked around the front again and got in too. He looked at me with hungry eyes and I kissed him. His tongue ring bounced in my mouth as he slithered his tongue in perfect chemistry with mine. I knew we couldn't continue with it right there, so I fought my eager desires and began to drive.

"How's a movie sound?" I asked, referring to what to do for our night out. He nodded in approval and suggested one to go see. The movie theatre was about 30 minutes away and I was getting nervous about what to talk about during the ride. I thought maybe I'd come on too strong with grabbing him when he was getting in the car and I began to feel a little embarrassed about it, so I kept quiet for a little while.

"What's the matter, Cutie?" He asked, noticing that I was being so silent. I didn't want to tell him the truth, that I was kind of regretting that I'd grabbed his ass, but nothing worthy of an excuse came to mind quick enough. "Nothing, really," I started, "I'm just wondering whether or not I should've come on to you so strong like I did at first." Ian smiled comfortingly and started to rub my thigh with his hand. He leaned over to me, still rubbing my leg and sucked on the side of my neck that faced him. He slowly rolled his tongue up to my ear, and again he nibbled on it and licked it. "You're so sexy," he began, "You see what you want and you take it. I love a man who's not afraid to put himself in control." As he spoke, his hand started to move in between my thighs, rubbing up and down, slowly getting deeper between me until he was rubbing my crotch and gently squeezing the bulge from my jeans.

My dick was now pulsating and I was beginning to devote less concentration to driving, but I didn't want him to stop. I needed the release from all this teasing.

Ian put his hand up my shirt and started to carress my upper body. He rubbed on my pecs and gently pinched my nipples after his hand had explored my lean abdomen. "Someone as fine and manly as you deserves a natural born cocksucker like me to satisfy them." His hand slowly dove down into my jeans and he grabbed on my erect cock. He teased it with his hand and tickled underneath my balls with his fingertips. "I think your dick agrees." He said softly, still licking my earlobe.

His head slowly made its way down near my crotch and he unbuttoned my pants. He kissed my hard visable shaft still hidden under the briefs before pulling it out and exposing the 8inched tool that stood proud and ready. When my dick entered his mouth at last, I could no longer continue driving. I pulled into a large nearby parking lot filled with cars as he kept sucking me off, motioning back and forth with his head, up and down on my cock. I was entirely in his mouth everytime he came back down, slipping my hungry dick deep into his relaxed throat.

The night was pitched black and I could see nothing except the shadow of him moving his head. It was the hottest thing I'd ever done, meeting a stranger for the first time and fucking their face in the dark as if he were a complete mystery boy that I didn't know at all, just looking to suck my cock.