College Sissy Pt. 01


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 Maltepe Escort 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.”


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?”


“What about 2 hours from now?”


I didn’t cum for a week so I’d be desperate enough to reach out. Anadolu Yakası Escort Two hours of almost having a panic attack later I texted and got the address. Turns out he was in my dorm, just a couple floors above. I nervously went up stairs and knocked on his door. Long enough to know he wasn’t waiting by the door he answered. He was in good shape, taller than me, and just in his boxers. He looked unimpressed, but athletic. He opened the door and walked back into his room, not inviting me in, but expecting me to join him. I followed. Inside was a room identical to mine except the decor.

On the ground was a large cushion of some kind with a blanket over it. He sat down and was looking on his computer.

“So uhhh…roommate isn’t a problem???”

“He basically lives at his girl’s place. Almost never here.”

“Oh… okay. So…”

“Just get on the floor, I’ll be there in a sec.”

I got down and just sat there, awkwardly.

“Strip. And get in position.” He said, without looking up.

I slowly did, still feeling awkward but not minding he wasn’t looking. Eventually I did get fully naked and got on all fours. He got up finally and got behind me. It took me everything I had not to shake. He slowly but firmly pushed my head down. I heard him lube up and he started to push into me. I had trained, but even then he was pretty big. I whined until he was in all the way, he stopped for a moment.

“Shhh…. it’s okay sissy.”

I ignored him, but started to moan when he began humping. It hurt at first but it changed to pleasure much faster than I had read about, or maybe it’s just because I wanted it to.

“That’s a good sissy! Daddy is going İstanbul Escort to fuck you real good.”

Again I ignored him. He picked up speed and it was at this point I became aware of his hands, they had been on my hips the whole time since he had pushed in, but he was gripping tighter now. Not in a bad way, I just noticed. Something about them felt really nice, I was not expecting that.

As soon as that thought left my mind, I started grunting a bit…a sensation I had only felt a little of before started growing in me.

“No, sissy. Keep moaning. I know you feel it, but moan like a girl.”

I tried to ignore that too, but he slowed down when I kept grunting, so I made sure to moan.

“Atta girl.”

Soon enough I finally felt it. I shook and almost choked on my own breath, and I came all over the blanket… I felt… amazing but thoughts didn’t make sense at that point. When I fully regained consciousness he had pulled out and was cleaning himself off.

“That…wow that better than I had expected…oh my god…”

“I know. I have a magic touch I’m told.”

I was still reeling, but I noticed a new sensation at my ass.

“Did you…finish?”

“Uhm, yeah. That’s kinda the fuckin point?”

“Oh, you didn’t wear…right…”

I was so preoccupied with what I was getting out of it I didn’t fully consider what I signed up for.

“Well, that wasn’t bad. When you want it again, let me know. Just need you to clean the blanket.”

“Huh? What?”

I was still foggy.

“I said, let me know when you want this dick again, but you need to wash the blanket.”

“Wait, you’re serious?”

“Do I look like I’m joking? That’s the price to keep getting this dick. You clean up.”

I am getting dressed by now.

“I provided…didn’t agree…I mean you set it out…”

“As I said, let me know when you are coming back.”

“Okay, jerk. Not gonna happen. Whatever.”

I leave. What an asshole I think to myself.

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