First time with my best friend [MM]

A few days ago, I left the following comment on a post asking about having sexual experiences with straight men:
“He was my best friend in my 20s. He was playing poker on my computer and stumbled across my porn..big dicks, humiliation, cuckolding, etc. He had no idea. We talked about it, it was embarrassing for me but he was really cool about it (and I kind of enjoyed the embarrassment of course!). Over time we started to explore roles, at first non-sexual (he would tease me in front of other friends, have me clean his apartment) but eventually it did become sexual. He was still straight but really enjoyed the control aspects of it… and the blowjobs! He knew how much I enjoyed it. Went on for a couple of years until he moved for work.”

I then got asked to talk about our first sexual experience together. So, here goes.

Homeless shelter, part 2 [MM]

The second part of this story, which takes place the day after part 1, was also posted by me to literotica years ago. I had intended to write additional parts, but never got past this. But, if there is enough interest, maybe I’ll just have to do so now!

This story is completely true and accurate, at least as best as I can remember it almost 25 years later.

The next morning I woke up feeling very strangely. Even though I was homeless and broke and completely out of my element, the depression and fear from the previous day was gone. I felt excited. Last night I had done things that would have seemed completely absurd and taboo to me before now, but at this moment it seemed like I was embarking on a new exciting adventure, and my situation gave me freedom to explore without feeling any moral obligations. Being homeless, on the fringe of society, meant that I could be someone else without worrying about consequences or judgments. I could allow myself to do and feel things without worrying or caring about what people would think.

Homeless shelter [MM]

I originally posted this (and a follow-up) to literotica years ago, thought I’d post it here. I also wrote a second part about the next day if there’s any interest.

This story is completely true and accurate, or at least as best as I can remember it almost 25 years later…

I’d always been a small kid, more brains than brawn. From junior high through early high school I was very insecure, awkward, out of place. But midway through high school I was introduced to drugs — pot, acid, coke — and suddenly I didn’t feel so uncomfortable all of the time. I felt hip and cool and less like an outsider. But it turns out I have an addictive personality, and pretty soon I was high all the time. I was smart enough and had enough structure at home to coast through high school. But when I moved away to college, living in the dorms, with no restrictions on my behavior, I really lost it…getting high pretty much 24/7, going weeks without showing up to class. It is not surprising at all that the year ended with me back at my parents’ house, having flunked out of school.