Part 1
All parties involved are over 18 years of age, all acts described are between adults.
After turning 18, and in my freshman year at college, I got very into anal stimulation. I had first seen it in porn, a girl reached around while giving a guy a blow job and fingered his ass. The guy was big and cut, but the orgasm seemed to make him weak. Jerking after that, I tried to achieve that level, but never seemed to have an o like that, even after I lost my v card at my first frat party. I used fingers and some choice objects to play in that area, and while it started to feel good, nothing like what was described in the research I did.
I had sex a few times after that, but it seemed more like right place right time than any skill on my part to talk to girls. And even then, I couldn't even begin to imagine asking a girl to do anything like that. And the Internet certainly didn't help. No girl was interested in my area and I didn't have the money to travel to the one or two that I did find to be interested. I certainly got plenty of unwanted male attention, telling me they had the magic dick game to unlock that kind of cumming.
Girls were always on my mind, but so was class. And even then, the obsession lingered. I couldn't even jerk off without something up there anymore; close, but no cigar. Finally, I started to relent. I started looking at responses from men, just a peak. A few seemed interesting, perhaps. The ones that were local and mostly not creepy, of course. They were nice enough, but easy to weed through. Way too big, either their cock or their gut, boring enough I thought they'd cum before getting it in, etc.
I figured it was a stupid idea and was going to delete the throwaway, but one response caught my eye.
"Same school. If you want a sissygasm, message me."
Obviously local, but the term "sissygasm" is what got me more than anything. I had read it before, but it didn't really resonate with me, not really who I was. But, that was so different from all the other guys. They didn't use any of those terms, they seemed to play it off that they were very straight and other than superficial similarities, there was nothing gay about our discussions. I thought originally that that was what I was looking for, but the matter-of-fact nature intrigued me.
"Hi. I saw your reply."
"when can you come over?"
"Oh! I was umm wanting to get to know you first???"
"U can call me Buck. That good enough?"
"Hi, I'm [I said a variation of my middle name]. So, what do you study?"
"I'm probably just going to call you Sissy. I don't get to know holes like you, I just fuck them. You said you wanted a sissygasm, and I know how to give them. Done it plenty. You can come over or not, but I don't need to play 20 Questions."
"I'm not a sissy."
"Whatever u call yourself."
"Okay."
Well, it could have gone better. Two weeks or so went by, but I couldn't stop thinking about how close I was. I'd been practicing for so long, I was sure I could take it, and what was the worst that was going to happen? I wasn't gay or a sissy, I just was looking for someone to find the right spot.
"When are you available?"
