This will be a series of short stories based on real situations that have come up in my life where I wished I had sucked a dick but didn't.
These stories are my fantasy of how things would have gone differently had I actually had the courage to suck the dick.
I'll start each story with a paragraph or two explaining how the situation actually went down and then get into the fantasy of how I wish it had gone down.
Everyone involved is over 18.
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A little background to set the stage:
Going into college I was very confused about my sexuality (maybe I still am).
At that point in my life I was 18 going on 19. I had only had sexual encounters with two people. One male and one female.
The male was a friend and I ended up sucking his dick. I gave him a lot of blowjobs and really enjoyed doing it. That lasted until I moved away to college and I never did it again. I still fantasize about dick to this day, but I've never had the courage to make those fantasies a reality.
That's probably because after that I had a girlfriend for a short period of time and I enjoyed getting handsy and making out with her when we were alone. Once I ate her pussy, I was hooked on that, I couldn't get enough of it. We eventually broke up though and sadly never had penis-in-vagina sex.
I was a young man confused, away from home and left to my own devices.
What actually happened that day:
We always kept our dorm rooms unlocked, my neighbor and I were the night owls of the group. One night when I couldn't sleep, I knew he'd be awake, so I just walked into his room like I had done many times before.
His roommate was sleeping but he was sitting as his computer, his pants were open and there was a hand towel on his lap. He had clearly been masturbating and I had interrupted him. We had a short conversation, ignoring the fact that his cock was covered by hand towel, then I left.
How I fantasize about this moment:
It was late, around midnight or so, and I couldn't sleep. I was playing a game on my computer and started to get bored. Normally, when I was bored I'd pull up some porn, pull out my dick, crank one out and go to sleep. I wasn't really feeling it, so I got up and went next door.
I knew he would be awake, we were both night owls that stayed up way too late playing videos games.
I didn't knock and just walked right in, like I had done many times before. The way they had their room set up I had to take a couple of steps in before I saw him sitting at his desk.
"Hey, man, I can't sleep, you want to play a game or something?" I whispered, oblivious to what he had actually been doing before I walked in.
"Uhhh I'm kind of busy..." he said.
I glanced down and noticed that his pants were unzipped, pulled open, and he had a hand towel on his crotch. It was propped up on his cock.
"Ohhhhhh. Uhhhh. My bad." I stammered. "Um, do you maybe want a hand with that?" I asked him.