Most guys fantasize about being with a girl when they jack off. I did too, but I also fantasize about being with a guy a lot. Thank god for the internet; knowing other guys were thinking the same thing made it seem all right. Having just turned 18 I wanted to do more than just fantasize. I did not know exactly what I wanted to do or how far I wanted to go. I was worried that I was fantasizing more about playing the girl's role then the man's. I knew I wanted a man to teach me, to show me, to be the aggressor, to seduce me and treat me like his whore.
I was 5' 8" 140 pounds. Swedish parents on both sides so I was very blonde and very fair skin with no body hair. I was very slim and had a very sexy ass. I had dated a few girls in high school but never got too far with any of them. I looked a lot younger then 18 and got carded even going into r rated movies, so taking a date to the movies was out.
I read a lot of erotic fiction and spent hours at night in chat rooms, never using my real name or location. I looked at bi and gay porn and masturbated a lot fantasizing it was me doing what they were doing in the porn pictures or movies. I started to look at gay and bi personals ads on websites and the Craiglist. I got extremely turned on by some of the postings. Especially ads of older guys looking for younger partners.
After awhile I decided to post my own ad on one of the sites. It read. "Chicago area, 18 yr old looking for experienced older guy to learn from, needs to be clean, disease free, discreet, and patient".
In the morning I checked my email and was surprised to find lots of emails answering mine. Half just said my ad was hot and gave no more info then that. Many were from guys around my age looking to meet for sex. That wasn't what I wanted. I found one that I really liked. It was from a 46 year old married man named James who lived in Chicago and wanted to introduce me to the bi scene. He wrote that he understood the importance of having a good teacher for my first time and would love to be my mentor. He left his email address and I hoped he would be hearing from me soon.
I replied to his email immediately and asked him to meet me in a chat room that night. He met me there and we went private. He was married and his wife Terry was cool with his bi actives as long as he was discreet. About 10 minutes after we started chatting on line he asked if I wanted to call him on the phone. His typing was not great so I called him like he asked me to.
He had a great voice, very deep, and very sexy! We talked about everything, sports, politics, life in general, then finally getting into sex. He wanted to know what our next step was. I told him I was not sure how far I wanted to go or how much I wanted to try. He said that was ok with him, he was not pushy and that it had to be right for both of us. He suggested we meet somewhere in public first, talk some more, and see how things progressed. I was fine with that and very excited.
We decided to meet at a Mc Donald's near my house the next day. He sent me a picture of him, just his face so I could I recognize him. I went to the Mc Donald's early and nervously sat nursing a coke wondering if I was doing the right thing. I loved the tingling feeling in my cock and balls from just thinking about him touching me there.
I saw James walk in and order a coffee. He sat down at a table near me and started looking around. He was even better looking in person then he was in his picture. He was very manly looking, masculine, handsome and looked self-assured. He was tall, a good head taller then me, 6'2" or 3", which was a turn on for me.
I walked over to his table and sat down across from him. I was nervous as hell. When I sat down and he looked up, smiled and said, "You must be Bob." I nodded yes. We talked for a while and he made me feel more comfortable with every word. He suggested we go for a walk, it was a beautiful day and there was a park nearby.
We walked around the park talking about everything: my mother, his wife, my college, his job. Finally, the conversation got around to sex. He suggested we go some place private to talk. He offered that we could go; to his car, his house, or any place I liked. I said I would like to look and maybe just touch each other to start with. He nodded and suggested we go over to an area in the park that had dense bush and trees where we wouldn't be seen. We walked over to where we were deep in the trees and got off the path to make sure no one could see us.
After an awkward silence, he smiled and asked whether it was ok for him to show his cock. I nodded and he pulled his pants down revealing his beautiful long, thick and extremely hard cock. I never saw a cock that big in person before. He was 8 inches maybe 9 and very thick with a mushroom shaped head.
I decided to drop my pants too exposing my 6 inch cock. He reached over and took my entire shaft in his large hand and started stroking me. I began to tremble from the wave after wave of tingling sensation that moved over my body like a blanket. It was as if James had read my mind about the role I wanted to play. The way he moved his hand on my small cock was like he was playing with a clit instead of a cock.
I looked up in his face and then closed my eyes. He read what I wanted and kissed me on the lips hard, he kept slowly stroked my cock while I was locked in his kiss. His tongue darted in and out of my mouth and it felt great. The chills from his kiss and him stroking my cock went up and down my body like an electric charge. He had me almost convulsing with pleasure. I reached for his cock and started to run my hand up and down his long shaft. After a few minutes of kissing and jerking each other, I broke his kiss and did something I wanted to do ever since I first fantasized about male sex. I surrendered to him completely and let my feminine side out, completely out.
I slowly sank to my knees and came face to face with the massive head of his throbbing cock. I wrapped my hand around it and stroked it a few times then stuck my tongue out and licked the tip. His precum was hot and wet with a musky taste and the smell was beautiful. I opened my mouth and took his head in, I slowly massaged it with my tongue, and to my joy, I heard him breathe deeply, I look up and made eye contact with him, he smiled and gently rested his hand on the back of my head. I started to take more of his cock into my mouth I got about half way down to shaft until I felt I couldn't take anymore then I slowly withdrew until the tip was between my lips. I stroked my hand up and down his thick hard shaft in unison with my mouth. I never sucked a cock before and hoped James was enjoying my first attempt as much as I loved sucking him.