I guess I was asking for it

by BillyBoy

2 Sep 2021 3136 readers Score 7.8 (13 votes) PDF Mobi ePub Txt


You've got to be handsome enough for someone to want to fuck you. And I wasn't. Surfing around the personals I kept finding guys who liked feminine-looking boys in girl's underwear. I thought if I put on some silk panties maybe a guy would want to take me out for a date. I'd never even touched another guy but I'd never really had a girl touch me either. This seemed pretty easy.

So I posted some pictures of me dressed up in my sister’s bra and panties and got a bunch of hits the first night. Everyone wanted to have me over for a party. It was so cool. A nice guy was just across town, so I put on some jeans and a t-shirt over my pretty pink bra and panties and drove over.

He answered the door but would not let me in until I dropped my pants and took off my shirt, standing there in her pink lace and cotton training bra and tight little panties, feeling humiliated and embarrassed. He made me leave my boy's clothes on the front porch. He looked me over then invited me in.

I reminded him this was my first time but before I could get the words out he took my arm and roughly pulled me right in. We didn't stop until we were in his bedroom. He held me down on the bed tying my hands behind my back with soft nylon rope he had there waiting for me. I tried to cry out so he shoved a washcloth in my mouth, gagging me.

He roped my legs together and sat me on the bed. He looked me over again while taking off all his clothes. He was hard and the tip of his cock was purple and throbbing.  Suddenly he was sitting next to me. Very close. I squirmed and squealed as he fondled me, pulling at the cute girly underwear. He was kissing my face, licking my cheek, and tickling my ear with his tongue. I kept noticing our reflection in the bedroom mirror. I was in the pretty pink bra and panties. It looked like a boy and girl were making out.

I also couldn't take my eyes off his hard and ready cock. My hands were tied behind my back. He turned me around and told me to jerk him off. He groped my ass and pinched my little tits. He placed his cock in my hands and wrapped my fingers around it, ordering me to stroke it.

It was hard, warm, and slippery wet. He held my hands tightly around it as he moved in and out. I mumbled a muffled 'Mmummph' each time I felt the head of his cock slide through my hands poking me in between my tender ass cheeks.

Soon I was stroking him willingly. He seemed to like me. He enjoyed our time alone together. He talked to me the whole time. Whispering how cute I was, and how much he wanted to make me his little sissy love doll, and how much he wanted to fuck me. He pulled the washcloth from my mouth and stuck his long wet tongue in.

He ordered me to continue to stroke his cock as he kissed me, open mouth, deep tongue, his wandering hands pulling at my nipples. I tried to concentrate on what I was doing but I was getting warm and dizzy. This was crazy.

I was pulled to the floor, kneeling with my face in his lap. My mouth was pushed open and filled with his big hard wet cock. It tasted like cherries from the lube he was using. He was pumping in and out of my mouth, ordering me to suck, holding my head with both hands. He pulled the rope loose from my wrists behind me and placed my hands in front of me. My fingers wrapped around his slippery cock again.

I was trying to keep my balance, my legs still roped together. I stroked the base of his big cock with my hands as I sucked the top half as hard as I could. He liked it. Soon his hands were holding my ass cheeks. The soft cotton panties were smooth and sexy. He liked them, rubbing and pulling at them. Suddenly he gripped the back of my neck. He groaned and laughed as he filled my mouth with his wet sticky load.

He pulled back as he finished by squirting a long stream right into my surprised face. He walked for the bathroom throwing me a towel. I was left there to swallow, then wipe up the rest of the dripping mess on my face and all over the front of my pretty bra. He returned, scolding me for pulling at the rope wrapped around my ankles and knees.

He looped the rope around my wrists and tied them behind my back again. This time he used a nasty rubber ball gag to quiet my complaining mouth. I’d never seen one before. It filled my mouth completely and immediately made my jaw sore.

I tried to squeeze it, move it around, adjusting it in my mouth to be more comfortable, but it was no use. I couldn't make a sound, but another muffled 'Mummph!' He took some pictures of me while he jerked off, squirting in my face again.

He hugged me and kissed me as he fondled my ass and my little dick wrapped up tight in the silky panties. He was sucking on my face and my ears. He pulled my dick out and stroked me until I came in his hands. I almost passed out! I'd never had anyone touch my dick like that before.

He told me that was the best thing I could do for him. It let him know I liked the girly clothes, the tight bondage, the nasty ball gag, and his filthy hands on me. I shyly nodded my head. After he untied me I showered and shaved all my body hair for him.

He had more silky clothes for me to wear, so I put them on. I sucked his cock and let him jerk me off all night long. He gave me a key as I left the next morning. I was to make him dinner and be waiting for him tonight when he gets home from work. I tried on several cute maid’s outfits until I found one that fit me just right. I buckled on the leather collar, ankle, and wrist cuffs he set out for me. I hope he gets home soon; I can't wait to have him teach me some more.

by BillyBoy

Email: [email protected]

Copyright 2024