Jerk Bros to Sissy Sisters Ch. 01

My name is Stan, I am 25 and currently rent a small appartment with Greg, a friend of mine.

We met by hanging around the same people, not really with each other, until we found our workspaces were pretty close, and the option of renting solo was not viable. A few weeks in, and so far he seems like a cool guy.

I was coming back home, carrying the groceries which would last us the rest of the week. My roommate and I weren't really the types to gobble down much, both of us are pretty thin, not quite the athletic types.

I turned the keys to our apartment and opened the door, instantly greeted by the sounds of sex from a far room.

Damn man, I thought, it's the third time you do this without warning. The moans and slapping of flesh kept going undeterred, looks like I haven't been noticed. I left the groceries on the floor and turned around. I would return soon, after things were quieter. Greg usually tells me to not be around for 2 hours, when he brings Pamela for some "alone time".

There I was, outside the door with a pressing hard-on, not the first time I got one from these two. There was one night they came home late, whispered sweetly and then started making out, which led to steamy action. All of it kept me awake in my bed, silently stroking my cock. I don't have a girlfriend, as I am in a bit of a weird phase, kind of questioning my sexuality. The nights where Greg and Pam screwed, didn't really help my predicament. I needed to do some experimenting, and get some steam off.

I returned after a while, thinking he'd finally be done, greeted again by horny sloppy sounds, mixed with ethereal voices, this time from his laptop. I walked in the room and found him on his chair, masturbating slowly, eyes glued on screen, face relaxed, mouth opened to an "O" shape. The sounds of sex and sucking were ambiemce to the voices of confident women.

"You want to get down on your knees"

"You enjoy having your hair pulled"

"Don't try to fight it"

"You wanna suck cock"

"You like what is happening to you"

"You are powerless"

We were both in a trance, he stared at the blinking screen while I was hearing the file and staring at his erect cock. As soon as he saw me he slammed the laptop and leaned towards his desk, no other way to cover himself, as he was completely naked. I turned away immediately, the image of his cock still in my closed eyes.

"Stan! Hey man, I was...doing what you think I was doing," he stammered a bit, unusually flustered.

It took me a bit to answer, "Wasn't your girl enough to deal with this...um, itch?" I asked.

"Yeah, I mean...it's a different kind of itch"

"...and that didn't sound much like regular porn..." I observed.

"Yeah... as I said...different kind of itch."

He lowered his eyes and caught a glimpse of the tent in my pants, I turned around and went to my room, a bit embarrased and oddly horny.

The next day we were both a bit embarrased at the table and I decided to release some tension.

"Soo...you into sissy porn?"

Smooth.

He looked at me in frustration, and then at the floor.

"It's just a fetish, nothing too serious, just to break up the monotony of mainstream porn."

Hmmm.

I had seen once or twice that kind of videos and posts, but didn't really leave an impression, couldn't really identify with them. This was different, I don't know what, but something about this whole scene yesterday hit me to my core.

"Nah, I'm not judging, I've seen some too. It's good to explore kinks, especially with someone else." Realizing the corner I'd backed myself into I asked "Have you spoken with Pamela?" Dodged a bullet there, probably...

He immediately unleashed his frustration.

"Pam? Yeah, I sure did, after weeks of working up the courage to open up, she told she wasn't into it. Yesterday I talked to her about it, we had a fight and she left me with an unholy hard-on." He looked down, a bit shamefully. "I loaded a vid and then you arrived. Things haven't been goin' great with Pam lately, that was mostly an excuse to leave."

"I've been having some...unusual ideas recently, I get how having certain...urges, can feel isolated, " I prodded.

"Soo..." treading carefully, "How about we vent some of that, between us?"

Greg looked at me puzzled.

"So you want to...experiment or something? Get those fantasies out in a safe space?" He pondered a bit. "I guess that would help."

I sighed in relief, he was responding rather well.

We later agreed on starting with small things. We searched and showed each other a mixture of funny-horny memes, with a few touching on the topics of sissification. He joked over my inexperience of me, trying to learn more of this "sissy stuff". We were having fun though, and felt closer, as this was something none of us would share.

As the days went by, things shifted from funny to titilating, to straight up thirsty.

He listened to a porn music video in his phone, full audio, while I got hypno video on mine, I had recently started watching these hypnos before bed. Soon he proposed we watched a porn video together on his laptop. I could feel things moving a bit fast, but I kinda liked the momentum we had built. Plus, we weren't doing something extreme. I quickly agreed to the idea, trying to keep the image of his cock out of my head.

We sat down and he started a pretty standard video, a blonde undressing and showing her impressive curves. We made one or two jokes on the quality of the vid, just to ease the tension, but the usual lust was already building up. This time though, another feeling was emerging, something subtle, evoked from her ample assets, a different kind of wanting. I quickly dismissed it.

The woman was soon accompanied by a handsome black male, them rubbing their bodies made me rub my dick, which was slowly poking out from my pants. Out of the corner of my eye I could see Greg checking it out. He whipped it out as well and soon we were both stroking our shafts.

Masturbation is a pretty intimate process, you know exactly what you like and the pace you want. Doing this with someone else, is different. You both pleasure your own bodies, going for the same goal, same release, you know you'll both cum.

That thought made me flare up, stroking faster, matching the pace of the muscular guy on the screen.

Soon we were breathing faster, wet fleshy sounds filling the room, a deep musk of cock surrounded us. We were getting close. The video closed in on her pussy pounded relentlessly by that big black cock. That black shaft and Greg's dick were all my eyes could make out when my whole body jerked, humping the air, as I blew my load. It went so hard, a string reached the laptop screen. Greg worriedly reached his hand to protect it, and stopped. Then he slowly moved his finger and wiped the stain I'd left. At the same pace, he brought it to my mouth, and feeling a bit dizzy I simply allowed it to go inside. He came instantly. Realizing he'd fed me my cum, I yanked my head, as we were both bit by post-nut-clarity.

He began stammering an apology as I got up and out of his room to the bathroom to wash it off. Standing above the sink, I discerned there was nothing left to wash off. Only thing remaining, a buzzing on my tongue, a sour aftertaste and a realization.

It wasn't half bad.