Playing dress up had always been a thing I did. Wearing makeup and soft clothing, perfume and lacy underthings. It was about the satisfaction of dressing the part, but nothing more. I never acted on it beyond that.
My roommate is a jerk. He’s a bit of a bully and a big jock. He’s in college on a scholarship and he likes to make my life a living hell in every way possible.
Everytime I bring a girl home he ruins it for me. Everytime I think I’m close the big musclehead stops things. And I haven’t been able to indulge my private fantasies for fear of what would happen if he caught me dressed up like this. What he would do if he saw me in those clothes.
But the urges got to me. The need building and building until I couldn’t ignore it anymore. Until it consumed and overwhelmed me. I had to give in just once. What was the worst that could happen?
He’s standing in the door to my room looking at me. He’s seeing me dressed like this, halfway through transforming into my feminine self. He’s walking in now, towering over me strong and big. And he’s looking at me with hunger in his eyes.
My roommate caught me dressing like a girl, and he likes what he sees.
Excerpt
Moaning I took his finger in me, feeling it stretch me out and fill me with a pleasure that made my whole body warm. My legs trembled, shaking and threatening to give out from under me as he fucked that finger in and out of me a few times before pulling back and pulling out of me completely.
“You’re really fucking tight,” he said in astonishment, and I blushed as I looked over my shoulder and saw him squirt another dollop of lube into his hand. This time he didn’t move forward onto my asshole, this time he squeezed and spread it all over the head of his cock.
My eyes went wide and he stepped forward to me, pressing his cock between my cheeks as I turned away to bury my head in the sheets and feel him press forward.
There was a pressure, an intense pressure behind me, and I made a focused effort to fully relax. I felt him pressing me open and with a gasp I felt him pop inside of me, and then I was doing it.
I was taking his cock.
It was overwhelming, there was pain but the pleasure took center stage. It took full control and left me gasping, left me vibrating and throbbing and wanting so much more from him.
He squirted another dollop of lube directly between my cheeks and withdrew his cock until his head was threatening to pop out before pressing forward again. He did this time and again, slowly withdrawing and then pushing into me, each stroke burying more and more of his length inside of me until the pain fully subsided and only the pleasure in my body remained.
Jack grabbed my waist then, holding my hips and beginning to fuck me properly. I moaned as he made me his, as he fucked my tight little asshole with his thick fucking cock.
“Goddamn you’re fucking sexy,” he said with a grunt, “With your tight fucking little hole and your tiny fucking waist. You’re so fucking gorgeous I can’t believe I’m doing this. I don’t think you know how lucky I am.”
I moaned and buried my head deeper into the bed, feeling him thrusting into me and feeling his cock throbbing as his pace increased and increased.
“Do you like it baby?” he asked, “Do you like how I fuck your ass?”
“Oh, Jack it feels amazing!” I cried out, my words muffled by the bed but still loud enough for him to hear, “Jack I’ve never felt anything like this.”
“Baby can you ask me to fuck you harder?” he begged me, “Can you ask me to fuck your tight boi pussy?”
I moaned and a wave of pleasure ran through me at his words, and I pushed myself up enough for my voice to be perfectly clear for him as I begged in a heady voice.
“Fuck me, baby. Fuck my tight little hole. Fuck my boi pussy and make it yours. Fuck me, Jack. Give me every inch of your fucking cock I need it!”