Sissy Sundays

It was the summer of nineteen-ninety, I had just graduated high school and was partying like a rock star. Occasionally when my friends would drop me home late at night, I would walk the block or so to a nearby two lane highway that led out of Boston and stick my thumb out, not ready to end the night just yet. I had a massive libido but knew the chances of a woman picking me up were slim to none. I wouldn't say I was cruising for a man either, just wanting the party to keep going.

So when I got in the man's car that stopped for me I didn't really have an answer when he asked where I was headed, but I was drunk enough not to feel awkward about it either. He was good looking in a rugged way, scruffy, maybe thirty-five. He had his shirt unbuttoned, and was playing cool music. I remember the conversation turning to sex almost immediately.

"Well, you're a handsome eighteen year old boy, it's Saturday night at two a.m., and you're drunk. It seems like you may be after more than just a ride somewhere."

"Yea, I suppose I am, I'm more open minded than most kids my age."

"You like sex, huh? I love sex. Girls, boys, it doesn't matter to me."

"Who doesn't?"

"You ever fucked around with a guy?"

"No. But I wouldn't mind trying it." I could feel my pulse raise after I said it.

"You got a nice cock? Let me see."

I said ok as I reached down and unbuckled then unzipped my jeans, pulled my penis out and started to play with it, getting it hard pretty quick. Before I knew it my new friend had pulled into a dark area and had also pulled his dick out, and it was pretty impressive, a lot bigger than me. Thick, long, cut, with a big head. "Com'ere", I remember him saying, and forcefully grabbing me by the back of the head and pulling me down on him. Within seconds I had gone from bi-curious to hungry cocksucker.

"Suck that cock."

He basically put my head on his cock and started to fuck my mouth, while I did what I knew I liked girls doing to me while I got blown. I didn't have to work too hard at it, it felt natural, it seemed liked I belonged sucking his thick cock. His hands holding my head and bobbing it up and down on his stiff rod didn't bother me at all, to my surprise it felt sexy and comforting getting my head and mouth fucked.

"Good little girl, you like daddies dick in your pretty mouth?"

That made me even harder as I hummed 'mmhmm', while hungrily sucking on his thick head, smacking my lips when he pulled me off it then stuffed it back into my throat.

"Oh yea, we're gonna make a hot little bitch outta you tonight."

He told me to keep sucking as he drove us to his place. When we got inside the modest but neat apartment, he told me to get naked and threw a pair of silky panties at me and told me to put them on. I really enjoyed the way he was taking control, and feminizing me. It was making me incredibly lusty and hard.

He told me how much he liked my body and how he wanted me to feel like a real woman. He had me lay down on my back on his bed, and told me to close my eyes and imagine I was a girl, with big tits and a pretty face and that my cock was just a big clit. I felt him get between my legs and start rubbing his big cock against mine thru the panties, while he played with my breasts and nipples. He sucked on one of my tits for a moment, then the other. I really was starting to feel like a girl.

When he kissed me, it took me by surprise, as I hadn't ever even fantasized about kissing a man. But he was strong and forceful about it and it served to further put me into a more submissive state. He sat up and started fondling my rock hard cock thru the silk panties and squeezed it hard, eliciting a moan from me and causing me to start rocking my hips. He stuck a thumb in my mouth and I automatically started sucking it.

"Good girl. Is your pussy getting wet honey?"

I hummed 'mmhmm' again while sucking his thumb and rolling my hips while he now had slipped my throbbing cock out from the side of the panties and was stroking it, covered in saliva he had drooled onto it. He grabbed me by both hips and lifted me, taking my cock into his mouth briefly.

"Oh yea, tasty little boy pussy" he said, jacking on my dick roughly. I was sucking my own thumb at this point, lost in ecstasy anticipating getting fucked. He told me to roll over and spread my legs wide, which I did while arching my back to stick my girlish ass out. He gripped my ass cheeks hard, spreading them, and I heard and felt him pull the panties out of the way and spit on my hole loudly and then spank me, hard. I couldn't help but keep rolling my hips, rubbing my brutally stiff cock against his bed. He slid a hand under and gripped it, squeezing it hard. Then, he started doing what I would later learn was called rimming me, and alternated that with fingering my boy hole.

When I got up on all fours he forcefully pushed my shoulders back down on the bed, but told me to keep my bitch ass up in the air. He told me how much I was gonna enjoy getting fucked like a slut, and I believed him. He fucked my ass with two fingers and told me to relax my pussy, as he gripped the base of my cock and balls and squeezed them. He told me to remain still while he slipped a cock ring onto them, isolating my genitals from my body and somehow making me feel even more girly.

"I'm so hard for you sweety, I think I'm gonna come right in your pussy"

After he said it he spit on me again crudely, then finally pushed his big, hard cock into my boy cunt. It didn't hurt one bit like I expected it to, it felt amazing. He had a firm grip on both my hips and immediately started pounding my ass, and I was lost in getting fucked in the best possible way. I answered 'yes' when he asked if my ass belonged to him, 'yes' when he asked if I loved cock, and 'whenever you want' when he asked how often I wanted to get fucked like the little slut he knew I was.

He pounded away on my female shaped ass for a good half hour at least, spanking me and spitting on me, grabbing me by the wrists and fucking me almost senseless. At one point he flipped me over like a pancake and spread my legs by the back of my knees hard and wide. He continued jack hammering away on my hole until finally with a loud "fuuuuuuuuuuck" he pulled out, mounted my head, and stuck his cock deep down my throat. He came right in my mouth, his big cock pumping and spurting a load of cum straight into my stomach. I came at the same time, spurting hot ropes of cum onto my belly as I held his ass in my hands, in awe of getting so owned like this.

After this he went down and licked my whole belly, eating up my seed. Then he gave me the most intense blowjob I've ever gotten, making me come a second time while never even losing my erection after the first orgasm. I felt like such a dirty little boy and I loved the feeling. He told me I needed to put the panties back on and dance like a girl for him before he would take me home.

When he dropped me off near my house he told me he expected to find me at the same spot at the same time next week, and that tonight had been nothing. That next week I was gonna have my world rocked. He said not to touch my pussy between now and then, it belonged to him now. This started to get me hard again, as I walked home while feeling the silk against my "pussy".

This week would be a challenge, as I usually jerked off twice a day. I already knew I would be getting fucked again next week, but I could never have imagined the complete degradation that was going to take place, and how wonderfully dirty it was going to be.

I remember the following week going by painfully slow, as time does when you're young, But I also remember wearing my panties twice that week and getting choked up and instantly hard everytime I thought about Saturday night. I managed to not touch myself for more than a few seconds in the shower all week long, which in and of itself had me as horny as I had ever been, with a "pussy" chock full of cum.

When Saturday had come, I couldn't help myself and went out shopping, like all girls like to do. I bought a garter belt and hose to match the panties I was wearing, an expensive wig, and some high heels. I also stopped at a pharmacy and grabbed some lipstick and mascara. When I got home I got in the tub and shaved my whole body smooth, even my armpits.

I didn't have the balls to wear any of this in public aside from the lingerie but I threw the rest in a backpack and went to the spot I had been picked up last week, and sure enough, the man was there right on time.

"How's my girl?"

"I'm well, how are you sir?"

"Doing good. You ready to party tonight?"

"I think I am, I been thinking about you all week."

"Good girl."

I was excited about my surprise but he was smiling as if he had the same feeling, which I soon learned he did. When he opened the door to his place I almost shit myself when there were two other men there already, drinking and leering at me from the moment they saw me. I excused myself to use the bathroom, with my heart beating in my throat.

I trembled as I took off my clothes, put on my heels, then took my time applying the lipstick, mascara, and black cropped wig. I was actually very fucking pretty, far more beautiful then I had ever really noticed before, WAY beyond passable. I realized that if I were to go out like this I would certainly get attention from men, and that thought had blood flowing into my cock already.

I took a deep breath and made my entrance. There was definitely a holy shit moment written all over the men's faces. Not knowing what else to do with myself I just walked straight up to the most handsome one sitting on the coach, got on my knees, and started unbuckling his belt and pants. I could see the other two start to undress in the periphery. It was oddly silent, which I took as a good sign. The man in front of me lifted his ass so I could pull down his slacks and boxers, and I moaned a rather female sounding moan as I took his full mast cock into my mouth. I closed my eyes and just concentrated on sucking his delicious dick as he lightly played with my hair, my face, and my tits.

After several, who knows how many minutes, I had gone from just being on my knees to sticking my girly ass in the air, once again almost involuntarily rolling my hips like I was fucking something under me. I knew this wouldn't last too long before I felt hands on my cock and on my ass. Then something unexpected but terribly exciting and exhilarating happened, someone tied a blindfold on my head. Soon after that, I felt a collar being buckled around my neck.

"Good girl, suck that dick, you're doing fine. You do what your told you'll be just fine."

That's when the spanking started. The first was hard but my automatic reaction was to just stick my bubble ass up and out more, in acceptance, and they just got harder. I felt my stiff cock roughly pulled out the side of my panties again and once again a ring placed on it and my balls, this one felt tighter. I could tell a swap had occurred and I was in another man's lap when a fresh cock was fed to me, this one felt and tasted different, maybe uncut. I just kept sucking and receiving blows to my backside, taking in occasional sneers and derogatory comments that filled me with lust.

I was suddenly jerked then pulled by a leash and told to stay on all fours. I was led to a bed where I was again manhandled by all six hands. Someone slapped my face and spit on it, causing me to gasp. I was choked and thrown on my back while a ball gag was fastened onto my head and pillows propped under my ass so my ringed cock and balls were placed in the air on full display. My wrists and ankles were being cuffed when I heard a doorbell and more voices. People were laughing and saying things that were gonna be done with me. I was helpless now, completely at their disposal.

Briefly I got scared that I could be in deep trouble. At this point I could be drugged, tattooed, castrated, and there wasn't anything I could do to stop them. I heard pictures being snapped which made me grateful I was mildly disguised.

"Lets torture her pussy, squeeze that big clitoris, hard."

I felt clothespins or something similar placed on my nipples. Someone slapped my cock then squeezed it very hard, while someone else slapped my belly and others were pinching me. Someone started sucking my cock and fnibbling, then biting it.

"Slide it up so it's head is hanging off the bed, I wanna fuck it's pretty face."

I was almost hyperventilating. Part of me felt like crying, but even that turned me on more. They had me spread eagle, propped up, and chained down now, while someone unbuckled the gag and forcefully fucked my throat. Two hands had me by the neck and were choking me enough to make me dizzy, as I felt my ass penetrated with a slippery lubed up cock. Someone else was still eating out my pussy.

The most emasculating part was when they had me on top, in a reverse cowgirl, bucking up and down while getting jizzed on on my face and chest. The guy fucking me would pull me backwards on top of him, and whisper what a nice ass I had, while he bounced it on him, fucking me as deeply as he could. They were saying things to me like "you're gonna grow your hair out" and "welcome to your new life" which all served to reassure me that in one short week I had gone from a skinny cute straight kid, to an over-sexed sissy whore.

Within four days I was working at a motel one of them owned. Within a week of then I was living there. The things that happened in that motel were a big part of shaping who I became. Perhaps I will write about some of those nights in the future, some are certainly worth reading about.