so I recently stumbled onto tumblr and found many pages dedicated to the feminization/sissification of men. I instantly loved it. I followed as many pages as I could that had anything to do with being a sissy such as sissy captions, cheating captions and so forth. I have been looking at so many caption and gifs of shemales/sissy boys who love being fuck, sissified, used and abused. It always got me super horny. I haven't heard from Steve in a while so I decided to put myself out there again and see what comes of it.
So on day I decided to post on Craigslist "young college student looking to be dominated and sissified". While providing all my stats. After about 30 mins there were several responses. But one stood out for me the most. It was a 36year old male who lived in the same town as me. This kind of scared me because no one knew what I was into or that I was curious about men. So we messaged back and forth for a little bit and he seemed like a nice guy. So I asked if he wanted to meet soon.
He said "How about tonight?" I was so scared but I agreed. For the rest of the day I was trying to figure out if I should back out or just not reply to him because I was so scared.
But I kept going on tumblr and looking at some caption which got me horny. Finally the time came, it was do or die. I agreed to met him at a park around the corner from my place. So I got dressed in black silk panties and a black bra and walked to the park.
He showed up 5 minutes after I did and at first I could see his face until he got close. Then I recognized him, HE IS MY NEIGHBOUR! we never actually met before I just know of him.
My heart was racing and I didn't know what to do. So he walked up to me and said "hi, I thought it was you posting online but I had to be sure". I didn't know what else to stay so I said "yeah".
He said "good, I was hoping you were into that kind of stuff. I've had my eye on you ever since you moved in." I just smiled awkwardly not knowing how to handle this situation. He then came real close and asked me what I want to do. I stayed quiet.
He whispered in my ear "do you want to me by little bitch?" I grin and nod. He says "good follow me, I have a job for you". I follow as he walks to some picnic benches at the park. It's dark at this point so there's very little visibility.
He hops up onto the table top and tells me to unzip his pants. I comply, revealing his 7.5 inch cut cock. It flops out as I slide his pants down. It looked magnificent. He demands I put it in my mouth. I slowly put the head of his cock in my mouth, I wasn't moving fast enough for him apparently. So he grabs my head with both hands and jams his cock in my throat. I could feel him about half way down my throat and I couldn't breath.
He kept my head there for a few seconds before letting go. I gasp for air. a few seconds later he does it again, this time I was more prepared and welcomed his cock in my mouth. this time when he let go he said "continue bitch, don't let me down." I grab his cock with one hand and wrap my lips around his cock and start to bob my head up and down.
After a few minutes he says "good Bitch, your my personal slut now." I say nothing and keep bobbing. He grabs my throat and stands up. he says "answer me when I'm talking to you!" I say "yes sir, I'll do anything for you". He grins and throw me toward the table.
Confused of what was to happen next. He pushes my toast to the table in one forceful motion and starts to kneed my ass.
all I could think of were those tumblr posts and imagining I was the on in them getting dominated. he then grabs a handful of my hair and yanks on it, pulling my head closer to his face.
"I'm going to fuck you and fill you with me seed you slut." He says. then throws my head back to the table. He pulls down my pants and panties in a swift motion and starts smacking my ass. I don't like the pain but I love the way he's treating me. He then pulls out a bottle of Lube and covers his cock. I feel 2 of his fingers rubbing my hole with some lube. All I could think was this is going to be painful but how nice of him to lube up so I don't get destroyed.
He grabs my hip bones and I can start to feel his cock search for my sweet spot. He eventually found it and then paused. He told me to relax and it will feel good.
I tried to relax but that was not hope. He then started to thrust his cock against my hole until the head of his cock popped in. I let out a small moan/cry. He pulls out and reinserted himself slowly, letting more of himself inside me.
every time I whimper a little. He did this until I could feel he was all the way inside me. the pain was something I've never felt before. he just sat there motionless until he thought I was ready to continue (I don't think I would have ever been ready). He starts to thrust long and hard, all the way out and all the way back in. When he pulls out I felt empty, when he was all the way in, I felt so stuffed like my insides were getting pushed together.
He started to quicken his pace after a few minutes. his thrusts were still very long and deep, he was just going faster and faster for what seemed like forever. My ass was getting so numb from his consistent assault and I did start to enjoy it. Throughout he kept saying "your my little bitch" "fucking slut" "my slave" "you dirty cumdump" All of which I could not deny, in fact in enjoyed what he was calling me. he was fucked me for a good 20-25 minutes before he said "are you ready to be filled with my cum you slut".
I said "yes daddy, fill me with that hot cum". He grabbed my hip bones continued his assault on my asshole for a few more minutes. Then he started to moan and his pace slowed.
I could feel his cock swell inside me and he started to unload his cum inside me. Every on of his last few thrusts were followed by a jet of his cum shooting further and further inside me. I felt so full, ashamed, horny and happy at the same time.
he pulled out, and I could feel his cum start to ooze out of my ass running down my legs. He smacks my ass and said "you know where I live, I'll be expecting you to come over to my place twice a week to be filled with my cum again and again. Or I'll have to tell everyone that I saw you having gay sex in the park." I lay there on the table breathing heavily and say "of course daddy". He says "by the way, my name is Jeff, but I like the sound of daddy." He smacks my ass one more time, pulls his pants up and leaves before I even move.
I walked home think about what just happened.
And I was kinda happy he said he would tell people about me, so I can say I don't want him to have his way with me, but secretly ill love every second of it.