First Time Gay Sex
By Get2itt

My first time was in highschool. I was a typical horny 15 year old, actually I'd have probably banged anything, boy or girl, but no opportunies arose, until one night partying late with some buddies, everyone left but me and "Richard".

I was pretty passed out when I felt him giving me a massage and talking to me, while I was on my stomach. He massaged me for a while, then got bolder and reached under and started tweaking my nipples. I still acted like I was out of it, but rolled over. He started rubbing my tummy and lower, and I sucked my stomach in to give him access to my cock.

He went down into my jeans (I didn't wear underwear) and felt my hard on and knew I was awake and game. He frantically unfastened my button and fly and I completely gave up my charade and lifted my ass to let him get my jeans off. He went straight for my cock, deepthroating me in one quick lunge, then started sucking me aggressively and hard, while taking off his own pants.

He swivelled around and put his cock in my face, and I tried to avoid reciprocated for a bit, but he was insistant and held his cock in one hand, and the back of my head in the other, and pretty much made me suck. I gave up resisting and just started to enjoy it.

He began playing with my asshole and I was loving it, he wet his finger, then 2, and was finger banging me DEEP while he gave me head, but didn't keep up enough pressure for me to get off. I know now he was prepping me for a fuck and he didn't want me to cum and lose interest.

After a bit of reaming me out, he moved behind me and lifted my ass up and pushed my head into the pillow and started rimming me deep and hard, spreading my cheeks to get deep in my asshole.

He pulled my cock through the back and sucked my semi-hard dick while using 3 fingers on me, and after a little while it didn't even hurt and I was pushing my ass back on his fingers, wanting more.

He took the hint, got some lube he had ready from the bedside table and greased up his cock and put the tube right up to my asshole and squirted a big glob of cold gel into me.

He told me to hold my ass open, and wanting it to go in as easy as possible I reached back and spread them, while pushing out as I'd read. He put his head up to my boypussy and pushed slightly, and my virgin ass just sucked half his head in. I braced for the push, and he kept up a steady, unrelenting pressure as it moved slowly in. When my ass ring popped around his head, the pain subsided (besides the fact I was still pretty buzzed and anesthetized from alcohol and etc.) he just held still and let me push back.

I felt an intense desire to have his cock hit a spot deep in my ass, and even though my assring was sore, his cock didn't hurt at all depth-wise, so I forced myself back on his 7 inches as far as I could go. He rolled me over without removing his cock, straddled one of my legs and lifted the other and finally hit a spot deep enough to make me groan with pain, but I took it like a girl. He leaned forward and cruelly bit my nipples while he fucked me with slow, steady strokes, hitting my prostate at the end of every stroke and giving me exquisite pain. I almost shot without touching my cock.

Then he did something that even though I was taking it up the ass, I didn't know if I was ready for. He started nibbling my lips, then lip locked me and kissed me deep and forcefully. After a few seconds I put my arms around him, he changed position and lifted my legs over his arms and started fucking me hard, pistoning in and out like a jackhammer.

By now my asshole was really getting sore and I wished he would cum. I grabbed his ass cheeks and pulled him deeper, even through the pain, and finally felt him pull all the way out except his head, and felt his cock pulse. I couldn't exactly feel the squirts of hot cum, but his cock immediately began to slide much easier in and out of my ass. He kept it up for several minutes after cumming, and let me jack myself off with his cock deep in my hitting my prostate, for the most intense orgasm of my young life, better by far than the many jack off sessions I'd had before.

This began a sexual relationship that secretly lasted for the next 3 years of highschool, going to all night drive in movies and sleeping over at his house (his single mother knew he was gay and even joked about him fucking me the next mornings, but kept my secret) and blowjobs during the day skipping class. I even learned to ride his cock in the driver's seat for a quickie before and after school, but that's another story.

So that was my first time.