Some Fun With My Sister’s Sissy Best Friend

Last week my sister sent me (26M) a text letting me know she’d be coming over to hang out on Saturday. We haven’t seen each other in a few months, and since I’m usually working and we live on opposite ends of the city, it’s rare we get the chance to catch up. I told her sure, that’d be fine.

Saturday comes around, and she shows up with three of her friends, Darcee, Nathan, and Jason (19M). Darcee and Nathan mostly kept to themselves, chatting with my sister, but Jason stood out right away. He was petite asian twink about 5’1 with a bleach blonde caesar haircut, shaved eyebrows and a clean shaven face. I set out some snacks and ordered pizza for all of us, and we all started talking while the food was on the way. My sister and her two friends were joking around and telling stories, but I found myself paying more attention to Jason. He was quieter than the rest, not really saying much, just nodding along listening to us share stories and catch up. Eventually the Pizza comes and we get to eating, while watching some shows on Netlfix. My eyes were still on Jason, his cute tight butt, small delicate hands, and adorable smile.

We’re all on the couch and suddenly Jason asks me where the washroom is and so I lead him to it. Before he goes into the washroom I quietly pull down my basketball shorts, and flash him my hard cock. Jason’s eyes light up and he asks me if he can touch it, I nod yes and his petite hands caress the shaft and head of my cock softly. Then I hear a noise from my living room that jolts us both, and Jason heads to the washroom and closes the door and I head back to couch to watch the show. When Jason got out of the washroom we both acted as though nothing happened, and we continued our Netflix binge, the sun started to set and my sister and her friends decided it was time to go home as they had a long commute back to my old neighbourhood. I said goodbye to them, but made sure to give Jason a quick wink before they all left.

Later that night, I get an unexpected buzz on my phone from my apartment lobby. I answer my phone and ask who it is and it was Jason. I immediately buzz him in, and go to grab my lube and condoms, because I knew exactly what he came back for. I opened my door, and in he comes dolled up with a blonde wig, and red lipstick. We immediately start kissing and Jason’s red lipstick started getting all over my face and neck. We both take our pants off and I start to stroke his little cock, and he reciprocates by stroking mine. We both end up on the living room couch, I fall into the couch, while Jason climbs on to ride me. Both our cock are touching and Jason’s petite hands start to stroke our cocks together, while we continue to make out. Eventually we take our tops off, and Jason looks at me. I ask him if he’d be okay if I ate his ass before I fucked him and he smiled and nodded yes.

I flip him over on his back, and tease him by thrusting my cock on his stomach, while I took his socks off to expose his feet. I start to lick his soles, and make my way down his leg. While I do this I reach over to the coffee table to grab my lube, and set it beside him. I make it down to his cock and lick his balls and then sucked his cock. He moaned while I did this, and pinched his nipples while I continued to suck him off. Then he lifted his legs up and that was the sign that he wanted me to eat his ass. I made sure to put some lube on my hand and rubbed it some on his asshole, I was still sucking and licking his balls and cocks. Then I made my way down to his little pussy, and I proceeded to lick around it and then tried to penetrate his tight little hole with my tongue. I kept this up for a bit, while stroking myself, and eventually fingering him. I thought to myself that, I could probably make him cum hands free just by fingering his little hole, but I wanted to fuck him. I wanted to breed him.

Jason spend a lot of his time getting ready in full sissy mode, and getting dolled up for me so I wanted to reward him with my cock. I took some more lube and got his ass as slippery as I could. I grabbed him by the ankles and pulled him closer to the edge of the couch, I admired his soft soles. Jason took his petite hands and used them to guide my cock to his tight pussy. I stopped when I felt I was about to penetrate, and he put his right hand just below my stomach. He was tight, incredibly so. I slowly eased my way in and gradually increased the speed of my thrusts. Jason’s wig began to fall off the harder I went to I take it off and tossed it to the side. I went down to kiss him again, while playing with his nipples as I fucked him.

I alternated between going to kiss him, and licking his soles. Eventually I decided I wanted him to ride me. I took him my his hands and pulled him up towards me, while I turned and sat down on the couch. I told him I wanted him to stay standing, while he rode my cock as deep as he could, and to my surprise and utter pleasure he took my cock balls deep. He kept riding me for sometime, and then I started to hear his moans turn into unsteady breathes, and that when I started to realize he was tiring. I told him to slow down and he got off my cock, and got into doggy for me. I spread his cheeks to gaze upon his beautiful wet pussy. I stuck my finger in it before continuing to fuck him again, the sloshing sounds that came from his loosening hole got me excited and I told him I was going to cum in his ass.

Jason looks back at me and says “Breed me Daddy” and a few strokes later I bust my load in his little pussy. I pulled out and spread his cheeks, as I watched his pussy gape, and my cum drip out onto his balls and his petite lil cock. I tried to get his cock hard, because I wanted to taste his cum, but it couldn’t. We both cleaned up a bit and went back to couch naked and started cuddling, we put on the show we were watching on Netflix earlier that day. Jason and I would kiss, and stroke each other cock occasionally, while we watched the show. We eventually felt tired and he came with me to my bed to sleep. He stayed for the rest of the weekend, and we’d fuck until he left on Monday. We set plans to see each other again next weekend, and I honestly can’t wait to breed his pussy again.