This is my first story of this nature, so please don't be to harsh...
Let me give you a little overview of the situation. My name is Jamie. I am an 18 year old male. I am 6'0 150. I am fit and have a slim muscular build. I have brown hair and brown eyes. I started having thoughts about other guys when I was 15. I think it started when I watched a shemale porno for the first time. I found myself to be surprisingly turned on by this type of film. Ever since then I couldn't help but wonder what something up my ass would feel like...
This takes us to the beginning of my story. The first time I ever masturbated was while I was in the shower. Since that time it has sort of become a routine for me. I mentioned watching some shemale flicks, and it was a day or two after watching one of these movies that I was in the shower and I finally decided I wanted to try it. I wanted to see what it felt like to have something up my ass. I spread my cheeks under the hot water and started rubbing my asshole. I could already tell that this was going to be something that I would enjoy. After a couple minutes of rubbing on the outside of my anus, I applied pressure until the tip of my finger slipped in. Ooh, what a nice feeling that was. I tried to push my finger in deeper but was confronted my resistance and pain. I took my finger out and spit in my hand and rubbed my asshole once again. After getting my asshole nice and wet, I proceeded to make sure my finger was lubricated by sucking on it. Confident that my finger was wet enough to go in without any problem, I applied pressure to my asshole once again. Slowly but surely I slipped my finger all the way in. I kept my finger all the way in as I felt my ass tightening around it. Slowly I drew my finger almost all the way out, then back in again. I noticed my finger starting to dry up again and sucked on my middle finger this time. My dick was getting harder and harder the more I would suck on my finger. I inserted my middle finger into my ass with a little bit less resistance than the last time. In and out, in and out. Before I knew it, I was fingering my ass, and loving it! I could tell that I didn't have much hot water left, so I decided to pay attention to my cock. I lubed my dick up with body wash and started stroking away. Within a matter of minutes I started spraying more cum than I ever had previous to that night. Oh god, it felt so good to cum after fingering my ass, I knew this was going to be a permanent practice...
I turned 16 and entered my junior year of high school. Fingering my ass had lost its effect on me. It just wasn't doing it for me anymore. I always wanted to be with another guy, but I was always afraid. Mostly afraid of rejection I think. My junior year is when things started to change...
Since I noticed my interest in guys, I found myself thinking about my friend Jake when I would masturbate. I've known Jake for years and well, before now I never really paid attention to how attractive he is. Jake is a year older then me but we are in the same grade. He has a similar build to me except he is a few inches taller than me and he has blonde hair and blue eyes. Never the less he is built like me and has nice toned abs. We go up to the gym a lot to work out, play basketball, but more importantly, to go swimming.
After a nice long workout, we decided to cool off in the pool. 9 o clock struck and the pool was closing. The gym closes at 930 so we had a half hour to shower and exit the building. The locker room was empty as it usually is on a weekday. We hit the showers as usual, both of us in our own stall. I just getting done washing my hair when I hear the shower curtain pull back. I see Jake standing ass naked in front of me.
“Hey, the soaps out in my shower can I have some of yours?”
I heard him say something but I couldn't process anything at the moment. My mind and eyes were too fixated on his large cock. It had to be at least 5”'s flaccid.
“Hey Jamie, I asked can I borrow some soap?”
“Oh yeah sure sorry I was just uh uh..”
“Staring at my cock?”
“Yeah well I mean I didn't expect you to just walk in like that”
“Yeah I guess you weren't the only one”
It took me a minute to realize what he was talking about. Following his eyes might have helped a tad bit. My cock was at its' full 6” inch length. Embarrassed as all hell I could feel my face start to flush.
“Jamie, it's okay don't be embarrassed. Your body is only doing what it feels is natural”
I am feeling a little bit better when I hear him say, “I always kind of had a hunch that you were gay, don't worry, I won't tell anybody if you suck me off”
I knew how good it felt to receive a blow job, but I had never been on the giving end of the equation. My heart started pounding. I had no idea what to do. I was nervous and caught off guard, however I didn't want anyone to know I like guys and I was really attracted to Jake. Without any further thought, I dropped to me knees, reached out with my hand, and took his cock into my mouth.
I went most of the way down and then back up and I could feel his cock hardening in my mouth. One more time back down then up and his cock was fully erect. Never did I imagine my first blow job would be to an 8 and a half inch monster. I took his head back in my mouth and tongued and his peehole as I stroked his shaft. He started to shove his cock further into my mouth. I was struggling to adjust to the massive invader in my mouth. I was four inches down when I heard, “Faster, Faster!”
I withdrew my mouth from his cock and then went back down, picking up speed with each repetition. Before I knew it, I could feel his cock hardening in my mouth, well the 4 and a half inches I had in at this time.
“Ooooh” he said, “Swallow my cum you dirty little slut”
I could feel his hot load hitting the back of my throat. I withdrew my mouth a little and gathered some of his cum on my tongue. It had a sweet taste to it. Needless to say I enjoyed it very much. Looking up into his eyes, I sucked his head till I was sure he was dry of every last drop.