The Association of Sissies Ch. 01

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"You have five more strokes. Get back in position before we have to start over at one." Jim barked at me.

I picked myself back up and arched my ass out.

"Fifteeeeeennn. Thank you daddy."

Jim was quick with the final strokes.

Jim pulled me across his lap again and rubbed lotion on my sore ass. He rubbed my cheeks and my thighs.

"I'm sorry you had to do that to me Daddy. I will never break your trust again." I said in a whimper.

"You know how much I love you. I only put myself through that because I love you so much." He replied.

He pulled out a bottle of lube and pushed a finger back into me while he lovingly rubbed my ass.

"I'm going to consummate our relationship now. This is a life bond. There is no going back afterwards." Jim said.

My penis was rock hard and jammed into his thigh. Jim started to insert more fingers and stretch my hole. I could feel Jim's cock grow in his pants. It felt like it was massive.

"Please make me yours." I begged.

Jim placed me down on my feet. He slid a black pair of g-string panties on me, one leg at a time. They were lacy in the front. They felt amazing on me. He then put a matching bra with pads on me. Jim removed his clothes and walked in front of me. His cock was hard. It was huge, with a large mushroom head and veiny shaft. His hairy balls hung low. His torso was covered in grey fur. He had a slight belly.

Jim led me to his bed. He placed me on the bed and yanked off my panties. He pushed me down on to my belly. He then straddled on top of me. Jim slipped a finger inside of my ass and made sure I was very slippery. I then heard him spread lube on his cock.

My anxiety was through the roof, but I never wanted something as much as I had wanted this.

"This is going to hurt, I'm not going to lie, but I'm going to enjoy it immensely. You can at least be proud to know you made me very, very happy." Jim said as he pressed his cock head up against my tiny hole.

He pressed harder. The pressure was crazy. I could feel his cock slowly slip inside of me. It wasn't a sharp pain. It was a dull painful pressure. I whimpered and moaned in pain as he continued to slip it inside. I thought I might pass out when all of a sudden it slipped all the way into me and my backdoor relaxed. His large head was inside.

Jim slowly worked more and more of his mile long cock inside of me. Jim lowered his torso on to my back while he had me impaled with his massive dick. He kissed the back of my neck and bit my ear lobes. He grabbed my head and twisted my face further back. He held it there and kissed me.

Jim kissed me again and again. He licked my lips and I opened my mouth. His tongue was in my mouth. I kissed him back. My first kiss, which was while being sweetly sodomized by this wonderful man. Jim kissed me passionately as he worked his cock in and out of me. What was once painful started to feel good. I couldn't get enough of all the sensations. I started to push against Jim's cock as he pushed into me. I moved my hips in sync with Jim.

Jim soon pulled me back until I was on all fours. He grabbed the hair on the back of my head and drove his cock all the way in. He pulled it out completely and then slammed it back into me. Jim fucked me like he was a wild animal. Jim then pulled out and flipped me over. He got between my legs and lifted up on them. He pushed his angry cock into my sex again. My body crashed into the bed as he fucked me. He thrusted hard and deep and pounded me until the bed frame snapped. We both rolled to the floor. Jim never missed a beat. He continued to fuck me with everything he had while I was pinned down to the floor. I felt something release in me and my body was overcome with deep pleasure. It was the longest orgasm that I had ever had. My soft micro penis shot ropes of cum as my ass clenched and spasmed on Jim's cock, Jim grunted and flooded me with his sperm.

Jim pulled out and laid to my side. I turned over and kissed him. I then went down to his cock and gently sucked on the tip as it slowly became less angry.

"That's a good girl, Janice. Clean daddy's cock with your mouth. You are my property now."

"Yes sir, I am completely yours." I said between slurps.

We slept in my bed that night.

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4 Comments
Julietv666Julietv666over 1 year ago

I really love your lengthy multipart stories like this. You take the time to construct a narrative and of course lots of sex. Each part has it's own story arc but stays connect to the whole story line. I also like the psychological aspect of the sex scenes with compliment the physical parts nicely. Please write more. Pretty please.

alladinstardukealladinstardukeover 1 year agoAuthor

Thanks for sharing. My first time was pretty clumsy. I didn’t think about protection until he was balls deep. I was just caught up in everything that was happening. I asked him to pull out and he agreed. He ended up breeding me and acting like nothing happened. I was a virgin and he was clean so he ended up just breeding me from then on. I would like to say that every other top I’ve been with used protection, but most of them refused to wear a condom but would agree to pull out. They almost never actually pull out. I some how made it through those misadventures clean, and now I’m in a long term monogamous relationship. I also found it sexy in hindsight, all the feelings of what did I just do, mixed with the guy not respecting my wishes. It’s all hot. I’m going to highlight it more in my next story.

MichaelfantasiesMichaelfantasiesover 1 year ago

The words, "There is no going back," is SO TRUE! That's what scared me the first time a guy fucked me. Once I had been fucked like a girl, I could never deny it. He knew I was a virgin. I asked him if he had a condom. I wasn't ready to be someone's "Girl," so to speak. He told me he doesn't use them. I was so nervous! I wanted it, but I didn't want the obligation that comes with it. He fucked me. It hurt, of course! When he was about to cum, I said, "Please don't cum inside me." He did it anyway.

Reading a story like this is hot. Having it happen in real life is a life changing moment.

AnonymousAnonymousover 1 year ago

Wow I can't wait for chapter two x sissy Lucy

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