I started crossdressing at quite an early age, 'borrowing' items of my mum's underwear and furtively dressing in them when she was at work. As I was an only c***d, and mum and dad had separated, I had quite a lot of time to indulge my little hobby! I used to love wearing her tights, the sexy feel of them encasing my legs and cock, and the way they made me feel so girly when I admired my reflection in the long mirror in our hallway. I would also wear her big full-cut knickers and doreen bra, and complete this with a lace slip and a pair of strappy heels or mule slippers that I could fit into th... Continue»
It was 10 o'clock on a Friday in late June of 1997. My parents were away visiting relatives for a few weeks. My s****r Kate had gone out partying with her friends for the night and wouldn’t be back till Saturday morning. Which left me all alone in the house.
For as long as I could remember I always loved dressing up in my s****r's clothes. When I was lucky enough to have a whole night with them out of the house, I usually went all out in my s****r's room. ??
I had been shaving what little body hair I had for years. I used to lie and tell anyone who noticed that a lot of swimmers and athletes shaved their body hair, which would have made more sense if I was an athlete or even went swimming but I had a complete lack of interest in both.
I snuck into my s****r’s bedroom and picked out a pair of black stockings, slowly I slid them up each leg. Next I pulled out a pair of her boots and slipped my feet into them. I put on a black basque and matching thong and looked myself over in her mirror.
As I was checking myself out, I glanced over at the window; to my surprise and shock I thought I could see somebody in my neighbours house staring back. I froze, unsure of what to do, what after all could I do. Apprehensively I disrobed and put everything back where I found it, before slinking off to my own room.
I tried to put the thought that I may have been caught out of my head, even at that short distance surely there was no way anybody could have seen that it was me, maybe they were just perving, thinking it was my s****r.
The following Monday, I left school just after the bell and made my way through the woods to my home. It wasn’t much more than a muddy track but it shaved a good 20 minutes off my journey. I was about halfway home when all of sudden I felt someone push me from behind with enough f***e to send me flying to the ground. As I looked up and saw my neighbour Joe, my heart sank.
Joe was a couple of years older than me, he had dated my s****r for a time and they’d been in the same classes at school, even when they were together, I always got the feeling that he had nothing but contempt for me. My s****r had dumped him a few months ago so I doubted that his feelings towards me had improved.
“Hey bitch” he said “Did you really think I wouldn’t have recognized you?”
I tried to sit up but he put his foot on my chest and pushed me back down. So I sat there on the ground, my ass sinking into the damp mud, hoping that the world would open up and swallow me, but I knew that I just wasn’t that lucky. How could I have been so stupid to get caught, why on earth didn’t I just close the curtains?
He stood there looking at me; I felt the tears welling up in my eyes, he told me not to be such a girl. I tried again to get up, but he just pushed me down again. He told me that I had a choice. I could either be the pussy he knew I was, or I could keep trying to get up and he would kick the living shit out of me.
I just sat there in the mud thinking I'd rather be thought a pussy than get my head kicked in. Let him have his moment I thought. He’ll get bored quickly enough, In a couple of weeks school would be over and if I could last out the summer without running into him then he’d be off to university and all this would be forgotten about. He smiled and told me
“It’s pretty simple from now on you need to do everything and anything I tell you too, otherwise not only will I beat the shit out of you but I’ll make sure everybody finds out exactly what a little pervert you are. Now, spread you legs, hold them open and close your eyes. If you move I'll beat you so hard"
So, I sat with my legs spread apart as he towered over me.
"Remember, don't move," he warned.
He unzipped his fly, pulled out his cock and before I realized it he was peeing right between my legs, soaking my jeans and underwear, I could feel the warmth spreading over my crotch as he said.
"You want to be a bitch, that’s fine. From now on you can be my bitch"?
As I started to move away from his pee he leaned over and slapped my face.
"don't move" he said
So, there I was sitting splayed and letting him empty his bladder all over my groin. I was so humiliated. When he finished he shook his cock and I flinched as droplets of his pee flicked my nose and mouth. He laughed and took a step towards me, I looked down as he put the tip of his cock against my lips.
“Put it in your mouth”
“Please” I protested, “Don’t do this”
He grabbed my cheeks in his hand and squeezed, forcing my mouth open.
“One way or another my dick is going in your mouth”
Reluctantly I parted my lips and let him slide his dick into my mouth, through the tears I didn’t even notice what he was holding in his other hand.
He snapped a photo with his phone
"Call it an insurance policy. My folks are going out of town for a few weeks, when I call for you, you’d better come over, if you don’t, well you know what’s going to happen. Do you understand?"
It was late on Sunday night when I got a phone call from Joe, he asked me if my s****r was home and when I told him she was out he asked if she still had her old school uniform, I considered lying to him but thought better of it. He told me to put it on and get my ass over to his house.
I slipped into my s****rs room and retrieved what he had asked, I slipped on a pair of white panties and a matching bra and padded out my breasts with toilet paper, I pulled a pair of knee socks on and pulled the plaid skirt up around my waist. The white blouse was tight around my newly padded breasts and really made my figure pop, I finished with the school tie and blazer and a pair of black patent mary jane shoes.
I checked myself out in the mirror, brushed my hair into a pony tail and added a little make-up, I looked pretty convincing, I was hoping that nobody would notice me once I stepped outside, it was only a short walk to Joe’s but the last thing I wanted was somebody else spotting me.
I made my way outside, luckily nobody was around, my heels clacked on the pavement as I made my way over to Joe’s wondering what exactly would be required of me. As I approached the door it flung open and there was Joe.
A flash blinded me as he again took my picture. He took several circling around me, I protested and put up my hands to cover my face.
“Put you hands down, I want to see that pretty face” he said, “Now come on in, I want to get a proper look at you.”??
“Are we really going to do this?” I said smiling nervously, “haven’t you already humiliated me enough?”
“if you talk like a bitch then I’ll slap you like a bitch” he said
I followed him into the lounge and stood before him as he poured himself a drink and stood inspecting me, I watched as his eyes moved slowly down my body. He sat down on the sofa
“Excellent, now come and watch the movie” he said.
I moved to the other end of the sofa to him and sat down.
“No,” he said, “Next to me.” ??
All I could think of was my parents and how they would react if they ever saw the pictures that Joe had taken, thinking better of it, I slid down towards him. He put his arm around me and pulled me close to him.
“There, isn’t that better?” he said.
I was hoping beyond hope that this would be the end of it. My heart was pounding in my chest, He flicked the channel to some cheesy porno and we sat watching in silence. It took my a while to realize his cock was sticking straight up out of his pants and his hand was slowly sliding up and down it.
“Now, slut” he said “Here’s how it’s going to be. I give the orders and you take them. If not I’ll be sending those photos to every single person you and I know”??
I nodded slowly; starting to imagine what might be in store for me. His hand moved to the back of my head and pulled my face down into his lap. ??
“Wait, no… I’ve never… hang on” I stammered.
“Shut up and suck, bitch,” he growled as the head of his cock pushed past my lips.
I felt so humiliated as he pushed my mouth down onto his cock. I could taste him on my tongue as he held my head firmly and started to pump his cock in and out of my mouth. I started drooling, as he hit the back of my throat, causing me to gag.
“Just relax, bitch, you’ll get used to it”.
He reached down with one hand and pinched my ass, my body jerked forward, seating him even more deeply in my throat. He pulled out and I gasped and coughed as he swiftly shoved it all the way back in. I tried to put my hands on his thighs to give me enough purchase to push him away but he was just too strong for me.
Finally he pulled out of my mouth. I slumped over to the side exhausted as he grabbed me by the arms and flipped me around so my head was hanging over the edge of the sofa, and my legs were sticking straight up the back of it. He quickly knelt in front of my head and f***ed his meat back into my throat.
He leaned forward and grasped my legs under his arms. His cock drove deeper into my mouth as I gasped for air. My jaw was aching and I felt what could only be his tongue probing my asshole, as his tongue pushed into my ass I let out an involuntary moan.
He slipped his tongue out of my ass and replaced it with a finger, he wiggled it in and out as my ass clenched. Suddenly, he pulled out of my mouth again. I whimpered as his finger plunged into my ass and then pulled out a final time. He grabbed my limp body and placed me on my hands and knees over the arm of the sofa.
“Time to see how much like your s****r you really are.” He growled.
I cried out in protest as he kicked my legs apart, my ass pointing at him, helpless. I knew what was coming and I felt like a bitch in heat as I felt him spit on my ass. I felt his cock pushing between my cheeks.
“This is going to hurt,” he said
He started to push forward. His hand curled around in front of my face holding a small brown bottle under my nose.
“Sniff it.” He said
I inhaled deeply as his cock pushed into my virgin ass, I screamed out and wiggled my hips. He grabbed the back of my neck and f***ed my head down into the cushions .I was whimpering incoherently as his cock slowly slid inch by inch into my tender hole. Finally, I felt his balls slap against my thighs softly. They felt heavy and warm. I felt like his cock was going to come out of my mouth he was so deep in me.
“you like that don’t you bitch? he said
Before I could even answer, he pushed the bottle back under my nose; I inhaled deeply as he started to pull his cock out of my ass.
“No, please” I screamed as he slammed it back into me.
I shrieked in pain as he began to truly fuck me. I wiggled my hips and slammed my body back at him. Endlessly his cock slammed into my tight ass forcing more cries and squeals from my lips. He held my hips firmly and pounded away at me. He kneaded my ass as his cock thrust deep into my bowels again and again.
“Who’s little bitch are you?’ He asked grunting as he thrust deep into my ass. ??
“Yours.” I whimpered forcing my hips backwards. He backed off.
He plunged deep into me again, pounding my hole even harder. He reached down and grabbed my throat, choking me and pulled me back harder onto his cock. I moaned as he held the bottle under my nose again. I inhaled deeply and my world exploded as every nerve ending in my tiny ass seemed to envelop his pounding cock.
Without warning he pulled out of me and twisted me around onto the floor. He positioned me upside down and pushed my legs back so my knees were on either side of my head.
“Open your ass, slut” he said
I reached up and spread my cheeks wide for him whimpering as he drove his cock back into my hungry little hole. He dropped his full weight onto me, driving his cock deeper into me. My ass swallowed his cock milking it.
“Cum for me, cunt, I want to see you cum.” he said
I reached up to stroke my cock furiously, it only took a few seconds before I cried out and began to shoot my load onto my face.
My cum spattered across my face into my open mouth as I moaned feeling his cock swell inside of me. I had never cum so much in my life as I tasted my own load and clenched my ass around his throbbing cock. With a shout he pulled out and knelt on the backs of my legs, pinning me down, he f***ed his cock back into my mouth. I could taste my ass on it as he drove it into my throat. He pulled out and grunted loudly as he started to shoot onto my face.
“Eat it bitch, get it all” he muttered
He shot jet after jet of sticky hot cum into my mouth. It ran down my cheeks, into my hair, I swallowed what I could moaning as he rested the head of his dick against my lips and squeezed out the last of his cum. ??
I lay there, exhausted as he took a few more pictures of me. My ass open and fucked raw, my face dripping with both his and my own cum. He chuckled and called me “Daddy’s little slut”.
“You’d better take a shower” he said,
I gathered myself up and made my way to the bathroom, I got myself cleaned up and got dressed. As I walked downstairs and back into the lounge I saw myself on the television having my face fucked by Joe’s cock, he’d filmed the whole thing. That’s when I realized this was going to be a very long summer.