It was my senior year of high school. I was 19 year old (so I failed a few times...) I had finally stopped growing at 6' and about 215 pounds. I played football and wrestled. I had a girlfriend, but was still a virgin in just about every way. I was getting sick of hearing all the stories in the locker room about everyone's sexual encounters.
I was home alone one Saturday afternoon. All I could think of was the story the quarterback was telling us the other night. He said that before the game the head cheerleader and one of her friends had given him a "good luck" blow job. It was infuriating. I need good luck just as much as him.
With my current girlfriend out of town I had absolutely nothing to do. I sat down at the computer and hit the AOL chat rooms. I had talked to some girls on there before so I thought I might be able to have "cyber-sex" or something to get my mind off the QB's tale. I jumped from one room to another finding nothing of interest. After a couple hours I was still bored. Then I saw something that caught my eye.
"Tampa M4M"
I joined the room just to see what was going on, maybe get a laugh.
There wasn't much conversation and I was about to be on my way again when I got an instant message from "HardOneTB". All it said was "Hi," but for some reason it grabbed my attention so I replied.
We talked for a while, not about anything sexual, just sports, TV, movies and other everyday things. Getting to know each other. I was actually enjoying the conversation.
As we were talking about the NFL playoffs he said, "So when are you gonna ask me to suck your dick?"
I was shocked. I didn't reply at first and just stared at the screen. A few minutes went by before anything happened.
"Still there?" he asked.
My reply was a quick one word answer. "Yes."
He quickly began to apologize and explain why he asked. His words on the screen didn't even register in my mind. I kept thinking about what it would mean if I actually went through with it. Would people find out? How would it feel? I was so nervous and excited about the chance to finally get a damn blow job, I couldn't really think. It was few minutes before I replied, "Where would we do it?"
He was quick to reply that we could meet somewhere and figure it out.
I explained that I was extremely nervous. I told him I wasn't gay and had never thought of doing anything like this. I also explained that I had never even had a blow job before. He told me that he'd take care of me. It didn't take a genius to know what he meant.
We discussed a place to meet not far from me and agreed to meet in 45 minutes.
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The sun had just gone down, the street lights casting a yellow tint on everything. I parked around the corner and sat there looking at him standing by his car, an older model Firebird. He was quite a bit older than me, probably late 30s. Slim but solid with short, dark, curly hair. He wore a basketball jersey and gym shorts. He was a good looking guy, not that I had ever thought about a guy's looks before. My heart was racing. I couldn't believe how excited I was, but I was extremely nervous too and the two feeling seemed to be at war. The nervousness almost took over as it was telling me to just leave. The excited part of me made me get out of my truck and approach him.
As he realized who I was he just smiled and looked me up and down. The look in his eyes made me even more nervous, maybe even a little scared. Without saying anything, I opened the passenger side door and got in. My heart pounding in my chest. He climbed in and smiled as he pulled out of the parking lot and onto the street.
As soon as we were on the road his hand went to my leg. I jumped at the touch, really not expecting it. He started rubbing my thigh getting higher and higher. I was so excited and nervous that when his hand brushed against my balls through the tight jeans I let out a low moan. I saw his smirk out of the corner of my eye.
He was being rough with his hand as he massaged my hardening cock through my jeans. I couldn't believe how good it felt to be handled that way. I guess he could tell how much I was enjoying myself because he suggested I recline the seat and get comfortable. I did just as he said. I leaned back and closed my eyes as he squeezed and rubbed my now rock hard cock through my jeans. I could feel the wet spot forming on my jeans from all the precum he was milking from me. After a couple minutes of this he told me to pull my pants down. I quickly complied, ripping my pants and boxers down to my ankles, finally freeing my throbbing cock. I also pulled my shirt up around my neck, leaving me naked from my chest to my ankles. He chuckled at my eagerness. With my head back and eyes closed he worked my stiff rod. Within minutes he had me ready to explode, expertly holding me on the brink. I was moaning and grinding in my seat. The feeling building up inside of me was incredible.
Before I knew it we were pulled off on the side of some back country road. When I noticed we were not moving I opened my eyes and looked down. The image of his black hand wrapped around my pale cock almost made me cum right there. I'll never forget that image. His hand left my shaft and squeezed around my balls. The warmth felt incredible. I closed my eyes and groaned in pleasure.
He asked me if I was ready and before I could answer leaned over and took my entire cock into his mouth. I had never felt anything so incredible! The hot, moist, deliciousness of a mouth on my cock was more mind blowing than I had ever imagined. I couldn't handle it. I was grinding into him, moaning. I felt his tongue massaging my shaft as he quickly bobbed his head up and down. His hand began to kneed my balls and pull on them. His mouth was riding my every thrust, I was practically fucking his face.
I must have screamed, the feeling was so intense. Just as I was about to release my load into his warm and inviting mouth he shoved one of his wet fingers into my ass.
OH MY GOD!
Cumming into a hungry mouth for the first time blew my mind, but the finger shoved into my tight virgin ass somehow made it 100 times better. Having his finger inside my ass hurt and felt wonderful at the same time.
He slowly moved his finger in and out of me as he sucked me dry. Once he had finished his job he quickly thrust his finger deep in to my ass and pulled it out. I could not believe the pleasure and pain his finger had provided. He leaned out the window and spit the mouthful he had collected onto the ground.
I didn't move for a few minutes and he sat there watching me recover from the most intense orgasm of my life. I was spent, my mind spinning from what had happened. So confused, aroused, and exhausted. He told me to pull my pants up. Slowly, I redressed myself, still trying to catch my breath.
Once I had fully dressed he leaned in close, put his arm around me and asked, "You like that?"
"That was awesome," I breathed in reply.
Smiling he said, "Good, my turn!" He forced my head down to his lap.
With his hand pulling my head down toward his crotch I got scared again. My heart was racing. I tried to pull back, but the angle he had me at and his brute strength made it impossible to get free.
"Stop fucking fighting me, boy. I did you a favor, time to thank me properly," he scolded.
The change in his voice was quite noticeable. His kind and gentle tone was quickly replaced by a demanding, dominating, and commanding voice. It caught me so off guard I simply gave in and let him pull my face down to his stiffening rod.
"Touch it, boy!"
I couldn't believe I was actually being told to play with this man's cock. Without realizing or thinking about it my hand moved to his leg and slid up inside the leg of his gym shorts.
Feeling his hairy leg gave me mixed emotions. Part of me started to get repulsed, another part of me relished in the fact that I was being told what to do. Call it Stockholm Syndrome or whatever, but I almost liked it. I didn't stop.