New Roommate with an Open Policy

In a different story, I mentioned that I'd had a string of bad roommates my first year in college. I finally found a roommate with whom I roomed for the rest of my first year in college. He was (well, still is) a very attractive, gay man and that led to several amazing experiences, but most of those are a different type of story. However, we started our experiences together with some hot conversations that led to open, often mutual, masturbation.

He'd heard about my rooming situations and, since he was currently rooming by himself, he asked me if I'd like to move in with him. I had such a bad string of experiences and was so frustrated that I was very happy for the offer and took him up on it. He was one of the nicest and most considerate roommates I've ever had. From the very first day, it was nice to get good sleep and be able to concentrate (mostly) on my studies. We're still good friends.

I was looking for a pen one day and couldn't find any on or in my own desk. I looked over at his. I felt really bad about going through his desk, because it felt like a huge violation of his privacy and I didn't want that, but I was desperate.

I started opening and closing his desk drawers when I found it. It was a huge, fat, and realistic black dildo. Even though I was prolific thus far in my masturbation life and had my fair share of anal play up to this point, I'd never actually seen a sex toy in real life. Growing up I certainly went through a phase where I used anything and everything I could find in the house and tried inserting it back there while I was masturbating.

I picked it up and looked at it in awe. It was sculpted to look very life-like with big, fat veins and had a big head. And I remember thinking there was no way I could accomodate it. Ouch, I thought, as I put it back right where I found it and didn't say anything about it until one night we were drinking.

We were sitting there, going through some cheap liquor, just talking one night. I was sitting on the couch and he was sitting on his bed. I was again sleeping at night in the top bunk, which always made sense with all my roommates because I am very tall and it was easy for me to hop up and down from the top bunk.

"I have a confession to make," I said, sheepishly. Liquid courage. "I was looking for a pen the other day, and I'm so, so, sorry about I, uhm, found your..."

I couldn't even say it, so I gestured with my eyes to the bottom desk drawer.

Realization dawned on his face. "Oh. You can use it if you want." He said it so matter of factly.

To this day, I wish I'd said something different like, "Why don't you show me how" or something like that, but what happened that night was just fine.

"So. You had fun last night," he said, after an awkward pause. I had. I was always trying my best to keep quiet at night when I was cranking one out. To not shake the bed or to not make too loud of "fapping" sounds. By then I'd mostly become a master at doing it quickly and quietly. Anywhere, any time (many more stories). But sometimes I got carried away, I know it. He'd never said anything or I'd never heard him wake up, so I'd assumed that he was a heavy sleeper and that I wasn't disturbing him.

I know I blushed hard. I was embarassed, in this particular situation. "It's really okay," he offered. "I usually do it, too, especially when I hear you." He smiled mischieviously.

Wow. "I had no idea."

"Well, I'm a little more discreet than you are." he laughed. Then, brightly, he said, "Tell you what. You do it. I do it. How about from now on, it's no big deal and we just agree that either of us can do it whenever."

Liquid courage. And so the "open masturbation" policy in our room started. It was crazy, looking back on it now.

"So... like, now?" I asked. He nodded.

To this day, I really don't know what came over me, but I couldn't unzip my pants and pull myself out quickly enough. If you've never sat there and looked someone straight in the eyes while wanking in front of them, it's hard to understand the experience. But that's what I did. That first time, he just sat there and watched me, taking a sip of his drink every now and then. I cranked away and stared straight into his peircing blue eyes. I don't think either one of us blinked.

Until I came with an urgent "Umpph". He dropped his eyes to watch the "money shot".

It was amazing. From then on, that's exactly what we did. It was incredibly liberating. I remember coming back to the room one time between classes to switch out text books, basically. I unlocked the door and opened it, and he was sitting there on the couch, reclined, with one leg up, pantless. He was very well-endowed and was engorged. He didn't even flinch. I walked in, set my books down, and made some silly conversation as an excuse to watch. He was using lots of lube and was making this slow, twisting motion with his hand as he slid it up and down his shaft. I looked at his eyes, watching me watch him, then looked down at his beautiful member, then back at his eyes. Then, to honor our "don't make a big deal out of it" pact, I told him to enjoy himself and that I wouldn't be back for a few hours, winked, and left.