PART 2 Slightly Older Male Friend - 1st Sexual Encouter For A Straight
*For actual first encounter, search this title minus "PART 2"*
This is the next encounter, which is MUCH juicier.
I'm straight male but my first (and 2nd, 3rd, 4th... 20th-ish) sexual encounters were all with another male (same person each time). This is the continuation of that story.
Now I was 12, and fully enraptured by the pubescent exploration of sex. I masturbated often. During the rare occasion that I was home alone, I'd watch entry level porn on the family computer (only internet we had), but more often I'd slide my dick between two pillows in my bed while imagining how warm, wet, and inviting the pussy of my beatiful crush down the road must be. (Call crush "C")
I still often hung out with my friend from post 1, but a long time went by with nothing sexual between us aside from talking about girls, and neither of us had even actually kissed a girl yet. But one night, during a sleepover, he asked if I wanted to play truth or dare. The last time was a year prior, and the game had ended with him cumming all over my stomach after rubbing his dick on me in a straddle position. The conditions now were just as they had been - us in his room at night, each laying in our own sleeping bag, with a nightlight and the moonlight through the window allowing us to see fairly well. The only difference - a crucial one - was that I wasn't interested in sex back then, having just begun puberty. But NOW I was, though with girls, not boys.
His question hung in silence for a little bit. Since we had never discussed what happened, I was unsure if he would steer the game in a similar direction as the previous year. I was also unsure whether or not I wanted him to. But I agreed to play.
Like before, he began with Truths. We knew each others C's, and he asked what position I'd fuck mine in if I get the chance. I admitted I'd start in missionary so I could play with her tits while we fucked. That thought immediately got my hormonal body aroused. 90 seconds ago I was ready to go to sleep, but now I was fully erect, horny, and energized. In the first T or D session, I had only felt a detached curiosity, but this time I was EXCITED.
As our Truths escalated, I saw his hand move in his sleeping bag where his dick was. It didn't seem like he was masturbating, but just lightly touching. I hadn't felt comfortable touching myself yet, but now that he was, I started to. I slid my hand into my pjs and ran my fingers along my firm shaft. Soon I saw him pull down his pants (still inside his sleeping bag), and start to move his hand more vigorously. At this point I thought this was his whole plan, we'd jerk under the covers while dirty talking about our Cs. I figured he was uncomfortable about what happened before, and didn't want to repeat it. Truthfully, I was equally disappointed and relieved. So while he was describing how he'd pound his C doggystyle, I had pulled my shorts off and was touching myself more passionately. As his description was ending, I prepared to take the reins with a detailing of 69, this being a position I held very high hopes for. Simultaneous oral sex between me and my C was a thought I had cum to MANY times. And as I would orgasm I'd imagine how eagerly she would gulp my cream, smiling beautifully as she swallowed every drop. But before I could speak, my friend suggested we try some Dares.
My heart raced. Both excitement and anxiety rushed through me. This could end up being the first time I orgasmed with another person, and while that's what every boy my age craved, I had obviously envisioned my first time to be with my C, or at minimum a girl. I had serious doubts about doing dares. I could decline and we'd finish as I had thought, describing fantasies while self stimulating, separately.
Instead, I agreed. He skipped the warm-ups and went right to touching each other for 30 seconds. We were too far to reach, so we got out of our bags, naked by now, and laid down closer. By now we both knew how to handle a cock (our own), so we knew what felt good on each other. We were enjoying it, but I knew I wouldn't be able to finish - I can't finish with dry stimulation. I decided this was good, I'd just finish him again, then we'd go to sleep and I'd have saved my first time. But after 30 seconds he stopped moving his hand, letting it rest on my throbbing erection, and he said "I dare you to let me suck you." This was a dream come true, minus one detail. I couldn't say no.
He took me in his mouth and it was bliss. My eyes were shut, and it was my C. I felt her love as he licked and slurped. He took me deep in his throat, gagging slightly as he slid his hands up my inner thighs. His thumbs tucked under my balls and fingers pressed at my base. He expertly moved his fingers as he sucked, licked and wiggled his head until I EXPLODED into my Cs eager throat. He kept his lips wrapped tight until I fully relaxed, then he pulled out the last drops of cum, and swallowed it all, just like I knew she would.
