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Printed from https://www.writing.com/main/view_item/item_id/1584365-Craigslist
by Eureka
Rated: GC · Short Story · Erotica · #1584365
A young boy meets an older man and has a night he'll never forget :) Autobiographical.
*An Applebee's in Pennsylvania*

I'm sure there are better ways to meet people. Heck, I'm sure there are safer ways to meet people. But I was burning up, and I didn't know what to do. I stood outside the entrance of Applebee's, dressed up in shorts and a navy T-shirt. I had trimmed my goatee/beard and tried to look as handsome as possible. This was so new, so incredibly scary to me, but at the same time, incredibly exciting. How did I get here?

Church was my life. Church had always been my life. It was a family thing, a really strict go-to-church-every-Sunday-Wednesday-Friday sort of thing. It was a non-PG movie kind of thing. A girls-wear-skirts and guys-don't-go-to-the-beach kind of thing. And it was NOT a kind of thing where you casually walk up to your parents and say "I'm gay." Definitely not. So I didn't. I would just think about it, all day every day. I'd find myself staring at men's packages. I found my niche'. It was definitely the older men, with their experience and smile-lines around their eyes and their tight jeans and khaki's.

I would meet men like this, look them over, never say a word, and think about them all night, holding my cock and wondering why I felt like this. I dreamed the pastor of our church would bend me over his desk during one meeting and fuck me long and hard, his cock plunging in and out of my young, inexperienced butt to my own moans and groans and throbbing cock. It would rub against the desk, we would climax, and he would calmly tell me when the next counseling session would be. I would walk out tucking my shirt in and the secretary would look up knowingly and schedule me again.

Then it was the principal of the school, then it was our basketball coach. I fucked all of these men in my sleep, or they fucked me. Either way would end with me spouting like a fountain in my bedroom or the bathroom, trying desperately to be quiet, moaning in my pillow.

Time passed. Life happened. Bible college happened. Everyone said I could preach, so I got my degree in pastoral theology. Maybe I'd be that pastor one day, I thought grimly to myself. I hated being double-minded. Two-faced. Just...well, being off. Went and led music at a church for two years. Started raising support to be a missionary. Got engaged to a girl and broke up with her when she told me she didn't love me. And this whole time, still incredibly gay, still turned on at every older man that greeted me, still fantasizing about every handshake and one-on-one meeting. Yet completely hiding it. Keeping it to hotel rooms and dreams.

After the missionary venture I came back to PA. That's when I decided to start searching. I responded to a post someone else had made on Craig's, but when we met I didn't feel like there was a connection. In fact, I was so torn between what I'd been taught all my life and what I wanted that I rejected the idea of meeting anyone else for two weeks. But after two weeks, I couldn't stand it! I put a post on Craigslist looking for an older man, saying I was completely inexperienced, saying to go easy, saying that I was ready to start trying. Several replies came in, but one man really stood out to me.

He was older but incredibly in shape. His picture was by a pool..muscular, fit, a beautiful full gray head of hair. The other was of his cock, at least seven inches and HUGE! And yet another one of him fucking another younger guy. He had a smile to him, a beautiful half-smile that made me hard just looking at him. But more than that...it seemed like a smile I could trust.

And so we e-mailed and decided to meet at Applebee's. He said he liked to meet somewhere neutral before heading back to his place. I was so unsure, so worried, about a Craigslist ad...could it be trusted? Could he be trusted? But frankly, I was just too horny to care. I needed to experience another man.

Let's go back to me standing at the Applebees entrance. A jeep drove up and parked, and out he came.

He walked up to meet me with a huge smile on his face. A huge, sexy smile. "Hi, I'm Rick." We went and sat down and got to know each other. He was a psychologist, a professional suit-and-tie kind of guy, and I was VERY attracted to him. I felt at ease talking to him about my life, and he was very compassionate and well-spoken. God, he had the most beautiful green eyes...I glanced at his package before we sat down, since he was wearing those tight denim shorts that older guys wear. He was huge. But anyways...sorry, that's later in the story. Back to Applebee's. He asked me if I'd like to go back to see his place. I agreed, even though I was still a little scared.

I followed him in my car 5 minutes to his house and he gave me a tour of the place, casually showing me the pool (where that picture was taken--God, that was a turn-on) and his huge house. It was well-decorated and clean, and all the lights were dimmed...we walked all through it, the kitchen, the living room, and he showed me his room. He showed me the bedroom right next to it. And then he turned around and grinned, saying "This is the guest room...I like to do other things in here" and he bent forward and pulled me in for a kiss.

I'd kissed girls before (because straight was the only way to go in my religion and several girls sort of expected me to) but this was entirely different. I could feel the stubble on his cheek and the strength of his desire. He pushed in further, wrapping his arms around my bottom and pulling me up against him. His kisses were slow, and they pulled you into himself in a hypnotic way...he was already getting hard, and I could feel his cock pushing up against mine. I was getting hard and I gasped for air which I'm pretty sure made him even harder...we groaned together, grinding into each other, and I was in love. He smiled and said "Very nice" as he stroked my bottom.

He led me to the bed by hand then, laid me out on it lovingly, but aggressively. He was so strong! We lay there and stroked each other, groaning and moaning our approval. "You're getting wet already" He chided me softly as he rubbed my dripping head, spreading the cum over the surface of my shaft. I laughed softly and continued to gasp as his expert fingers stroked, flicked, and rubbed me up and down. I'd never been so hard before in my life. His eyes were a hypnotic sea of green, and I was lost in them.

And right then, I was completely his. He could do whatever he wanted with me.

All of a sudden he grunted "Oh, fuck," rolled up on top of me, and spread my legs apart! He started grinding me as hard as he could, groaning and saying my name. I gasped as his stomach rubbed against my cock, getting it harder and closer to climax with every thrust. I started to gasp and he smiled and started to go even faster, knowing I was going to cum. I put my feet around him and started breathing harder and faster. He looked into my eyes, serious and passionate. That's when I knew this was magic. This was more than sex. We were giving pieces of ourselves to each other, me and this mystery psychologist. I started to jerk my hips up uncontrollably, and he said calmly "let it out." I did then, I climaxed, the biggest I ever had in my life, and he just kept grinding me, making me shoot more and more onto his and my belly. We clutched each other afterwards and kissed. His kiss had a way of just pulling you in and keeping you there...I could kiss him forever. He looked at me and I knew, right then, what I desperately needed to do. I had to suck him off.

I started kissing my way down and he groaned and nudged me further, gasping in ecstasy. His dick was SO huge! I worked my way slowly around his throbbing head then started bobbing up and down. He started fucking my mouth then, and I stood as still as possible as he groaned and grinded into me. We were there for what seemed like hours, and I loved every second of it. He was stroking my hair and calling my name as all this happened...then he came, and I gasped and took it all. I couldn't believe it could be this wonderful.

That night we spent quite a while in each other's arms. never in my life had I felt so safe. Never in my life had I been so loved. I knew that I'd been missing this all this time.

I'll never forget our first night :) Thanks for reading.
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