A Sissy Boys Hard lesson

Reader discretion is adviced, this story contain graphic content depicting violence and rape which may not be suitable to all readers. This is a fictional story and do not portray real events or real persons.

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The next week when I finished college I was shocked to see the evil looking bald black man in his car outside. I knew he'd only be there if he was waiting for me. He called me over and I was shaking with nerves.

"Get in boy, we need to talk." he insisted. I didn't argue with him and got in his car. "Where do you live boy?" he asked. I nervously told him and he said he would drive me home. On the way he told me he wanted to see me on his own, no other men, just him. He wanted me to go to the trailer and dress for him, he wanted me to bring my girly clothes but he had a dress he wanted to see me wear. I nervously agreed to meet him later that evening at the mall. I was kind of relieved when we arrived near my house and I hurriedly jumped out hoping no one had seen me.

I had three hours to ready myself for a night with this man, I could hardly think straight as my head was dizzy with excitement. I bathed and sorted my clothes, packed my stockings, shoes, ankle socks and my pigtail wig in a bag then opened my drawer to select the perfect panties for him. I had lots to choose from, I had some very cute ones with things printed on them and they all had a little bow at the front on the waist elastic. I had pink ones with little daisies, cute white ones with little love hearts, plain black, light blue with teddy bears, yellow with little strawberries. I didn't want to disappoint him by wearing the wrong color of panties so I grabbed a pair of each. By the time I was ready and left the house I was feeling very nervous. I hurried to the mall as I didn't want to risk being late for my meeting.
I made it in time and felt more relaxed as I waited for him, after all it was possibly going to be a fun evening and maybe not scary at all.

He appeared on time and my nerves returned as I got into his car. He barely spoke as we drove off toward the trailer. I sat quietly as we drove but wanted to break the silence. "So what is it you want me to wear for you Sir?" I asked nervously. "A nice little sundress, I want you to wear it for me with your pigtails and panties and we are going to have some fun." he replied. I asked if he had enjoyed the other night at the trailer with all the other men there. "Yes but I want you to myself for a little while. Did you like it when we all fucked you?" he asked. "Yes I did, it was fun." I replied, losing my voice with nerves as I did so.

My legs started shaking again as we arrived at the trailer, I didn't feel in any danger but he just frightened me, he was so big and powerful and had a nasty streak in him. or so it seemed.
We went inside, he put on the heating and closed the drapes. The room was pretty much as it was when I was there the other night, there were four cameras on stands as they had been last time.

He smiled at me and said "Don't be nervous, I wont hurt you boy but I might spank that pretty little ass of yours. Here put this on for me with all your other girly stuff." He passed me a bag, inside was a pink cotton summer dress. I pulled it out and seeing it was so small I wondered if it would fit me. I had never worn a dress before, I had always been dressed as a schoolgirl. I reached into my bag of clothes and took out several pairs of my little cotton panties. "Which panties shall I wear for you Sir?" I asked nervously as I held them up to let him see. "Well lets have a look." he said as he came over to me. He picked up my white panties with the tiny pink lovehearts and the little pink bow at the front and said, "Wear these ones for me" The little white ones were my favourite panties of all, it was almost as if he knew.

He took my pink panties with the little daisies on them and sat down in a chair and waited for me as I went into the other room and dressed.
I felt very nervous as I removed my boy clothes and readied myself for him. I put on my black holdup stockings, white frilly ankle socks and schoolgirl style shoes and my favourite white cotton panties. I stepped into the pink cotton dress and pulled it into place. I fastened the buttons on the straps on the shoulders and straightened it. It was a perfect fit although it was a bit short to be decent but I wasn't going out in it. Lastly I put on my pigtail wig and made up my face as quickly as I could in a small mirror on the wall.

I tottered on my little black high heels back into the room to see him sitting there grinning with his cock in his hand and gently working my pink panties up and down it.
I felt a little embarrassed standing in front of him and nervous too. He got up on his feet and turned on all the cameras then sat back down and looked over at me.

"Get over here girl." he snarled so I obediently tottered over to him. "You look real sweet in that little dress girl." he said as he gestured me to stand closer. He lifted the hem of the dress and looked at my panties. "Oh my little darling, what lovely little panties you are wearing." he said as his hand wandered all over the front of them.
"They're my favourite panties Sir I hope you like them." I mumbled shyly. "Oh yes I like them, so do you wear them to tease men?" he asked. "Sometimes I tease men in my panties Sir but I don't mean to." I replied.
"Take your panties off girl". he demanded. I hesitated and he shouted "Now slut." I was shocked at his anger and obediently reached under my dress and wriggled them down and off.
He snatched my panties out my hand, he threw my pink panties on the floor and draped my white panties over the head of his cock.

"Now you get down on your knees little boy and be nice to Daddy's cock." he ordered in a very threatening way. I obediently knelt down and tentatively took hold of his cock, my little white panties were over the huge bulbous head and his pre cum was already leaking through them.
I adjusted my panties so the front of them was over the tip of his cock and tentatively leaned forward and took his panty covered cock into my mouth.

He grabbed my head and forced my mouth further down his cock, I tried to draw my head back but he held it tight. I almost gagged as he was so rough and his cock was so thick. "Oh yeah little girl, suck Daddies cock like a good little slut." he said as I did my best to do it like he wanted.

My panties were soon wet with my saliva and all his slippery pre cum, I moved them to the side exposing his naked cock head to my warm mouth. "Ahh your mouth feels good, you're gonna be my little fuck toy now, you hear me boy?" I nodded as I sucked him, unable to take my mouth away to answer him. His cock was very hard now and filled my mouth completely, he was leaking loads of pre cum and I could taste it. I wasn't very experienced at this but began enjoying doing it almost as much as he was receiving it.

I did the best I could to please him and did it like the little slut he wanted me to be. I was ready for him to cum in my mouth but just as I thought he was near to cumming he suddenly lifted my head from his cock and grabbed my arm and pulled me to my feet. He lifted my wet panties from his cock and handed them to me. "Put them back on." he ordered.

I carefully hooked them over my high heel school shoes and pulled them up into place, the front of them was soaking wet with his pre cum and my saliva and my cock could be seen through the thin wet cotton. He instantly grabbed my arm and pulled me over his lap. "You little fucking whore, you like to tease men everywhere you go, you deserve to get fucked real hard you little slut." he shouted as he lifted the dress up over my bottom and smacked my bottom.

He went wild, he spanked me so hard and fast it took my breath from me. It was so painful that I tried to wriggle off his knee but he grabbed me back and spanked me again. "Fucking little slut, hold still." he shouted as he whacked me. I struggled to the point I was able to roll onto the floor but he launched himself at me and stopped my escape. I was on my knees and he was holding me round my waist, I pleaded. "Oh please Sir stop." but he ignored me and set about spanking me hard.

He let me go for a moment but it was only for the thrill of the chase I'm sure. I got to my feet he followed and grabbed me as I tried to escape him. He slammed me against the wall and held my throat. "Trying to escape from me huh. you little fucking slut?" he hissed as he ran his hand down under my dress. "No Sir" I replied with tears running down my face. He kissed me then licked the tears from my cheeks as his hand roamed all over my thighs and eventually came in contact with my cock through my thin white panties. I had my legs tightly together almost like it would give me some protection from his touch, almost trying to draw away from him as if I could.

He kissed me hard as he groped and squeezed my little cock through my panties. I was struggling for breath and was relieved when he let go my throat and stopped kissing me. He dragged me over to the chair and pushed me face first over the arm. He held me down as he flipped my dress up over my back. He spanked me hard several times, I pleaded with him to stop and tried to struggle away. "Hold still girl." he shouted as his big hand whacked me over my panties. I continued to struggle and almost escaped his grip but he snatched me back. "You little bitch, stay still" he growled as he whacked me as hard as he could. "Oh please no, please stop Sir." I pleaded but he ignored me.

After a few more hard whacks he did stop, I stopped struggling too. I lay over his lap breathless and was so relieved he had stopped spanking me. I felt him sliding his hand under the leg of my panties and running his fingers over my hot little bum cheeks. His hand was soon between my legs and his fingers slid over my little hole. "I got myself a cute little fuck toy here" her said as his finger slid inside my bottom. "Oh no Sir please don't do that to me" I pleaded as I felt his finger go deeper into my tight little hole. I pulled away to evade his fingers but he got angry with me again.

"Stay still slut" he shouted as he held me tightly over his knee and whacked me hard several times. I gave up my struggle and he stopped whacking me. "Little sluts like you deserve their ass paddled hard" he growled as he ran his hands all over my bum and thighs. I felt him grabbing at the back of my panties, he took hold of the left leg elastic where it crossed my bottom with both hands. "Now lets see this cute little ass of yours" he said as he bent his elbows in preparation to rip them apart. "Oh no Sir, please don't, they're my favourite panties" I pleaded but my words were drowned out by the sound of snapping elastic and tearing cotton. "Shut the fuck up slut" he shouted as he ripped the back of them wide apart. My pleading and struggling was in vain, he was going to do as he pleased and I could not stop him.

"Aww you got such a cute little ass gurl" he said as he ran his big hands over the exposed flesh of my bottom, he ripped the cotton of my panties further apart to completely bare my bottom.  "Mmm that's a real cute little ass on you gurl" he hissed as he rubbed his in between my cheeks and over my little hole. He spanked me again quite hard. "Oh please don't spank me again Sir" I pleaded but he held me tightly and continued. My panties were in tatters and my bottom was now bare to his punishing whacks. Every time I struggled he would hit me harder and shout at me to stay still. I couldn't escape him so I had to endure the hardest spanking I had ever had. My bottom was on fire, my panties were hanging in tatters at the back and tears were in my eyes. I was more than relieved by the time he decided I'd had enough.

He pushed me onto my back and hooked his hand into the top of the sundress and pulled. The thin dress gave easily and he just ripped it apart. "Ahh please Sir no, don't be so rough" I wailed but he ignored me and set about reducing the pretty pink dress to shreds. He ripped it completely off me as I struggled uselessly against him. He threw the remains of the dress over the room and grinned at me as I cowered from him. I was now naked except for my half ripped panties and stockings and shoes, I got up to my feet again but he was right on me. He slammed me against the wall again, he looked down at my near nakedness, although the back of my panties hung in tatters they were still on and covered me normally at the front.

My little cock bulged the white cotton, it was tiny and soft as I was so frightened. His hand went to the front of my panties, he groped my small cock through them and kissed me hard. I was relieved that he was kissing me now and not spanking me or throwing me against the wall. "So did you like being spanked and fucked by all these men the last time you were here little girl?" he hissed. I wasn't sure what to say, I didn't want to make him angry. "I did Sir but the men were very cruel to me" I replied hoping it would be the best thing to say. He kissed me again and then grabbed my throat. "Did you like when I ripped your little panties apart and fucked you like the little whore you are?" he asked. "Yes Sir I did" I answered, this time I was honest. "I'm going to fuck you again you little slut, do you hear me little boy?" he said in a real nasty way with his face pressed against mine. "Yes Sir I hear you." I answered quietly.

I felt my legs trembling, this big evil man frightened me as much as excited me.
He pushed me up against the wall again and held me, he took his cock in his other hand and pressed the bulbous head against the front of my panties. He rubbed his leaking cock all over the front of them, leaving wet patches on the cotton.

"These are cute little panties you have on darling." he said as he reached down with his other hand and hooked his big fingers into the waist and yanked them outward at the front. He held them tightly out stretched and rubbed his cock inside then and all over my naked little cock. He looked at me with an evil grin and said. "Well would you like me to rip them off you just like I did last time and fuck your sweet little ass real bad?" he asked as he continued to wet my panties with his cock.

I knew he would do as he wished anyway but I wanted to seem unwilling. "Oh no, please don't." He kissed me again, his tongue was in my mouth and I felt very dirty. He was jacking himself against my panties and I felt my little cock begin to harden even though I was still shaking with nerves.

He stood back from me for a moment and seemed to admire me as I stood shaking on my high heels wearing only my stockings and partly torn panties. "Yeah I gotta fuck you hard girl" he snarled at me as he reached forward and grabbed my arm. He forced me to the floor on my back and straddled my legs, I instinctively struggled and pleaded. Oh please Sir let me go." I wailed but he ignored me and kept at me. "Don't fight me little slut it's no use." he said. "No Sir, please don't" I cried as I struggled to try and free myself. His powerful hands held me down as he put his weight on my legs. He leaned forward over me and kissed me, I tried to turn my face away but he held my jaw in his hand.

"You love to be raped, I know you do so stop pretending you don't want me to do this to you gurl" he growled as he let go my face and reached for my panties. I struggled as his huge fingers stroked over my skin and curled round the waist elastic at the front. "Hold still while I get these off you." he said as he took hold of my panties with both hands either side of the little pink bow in the centre. "Oh please don't rip my panties Sir." I pleaded as I struggled and tried to push his hands away but he just yelled at me, "Shut the fuck up you little slut" and yanked his fists apart. I heard my panties tearing as they came apart like tissue in his strong hands, I struggled to try and stop him but he ripped them completely apart straight down the front in line with my little cock.

"Ahh please don't Sir" I cried as my hands flew to cover my naked little boy cock. He grabbed both my wrists and held my hands by my side. He stared for a moment at my nakedness, my torn panties were still round my legs. "You sure are a pretty little gurl, I'm gonna love fucking you" he hissed. His hand stroked over my little cock, I struggled but he held me down easily and then set about tearing the remains of my panties off me completely. "Stop struggling you little slut." he shouted as his big black hand dived between my legs and grabbed the remains of my panties and ripped them violently from round my thighs. Seconds later the tattered remains of my little white panties were in his hand, despite my pleading and my little struggle against him, he now had me naked except for my stockings and shoes.

He leaned over me and held my savagely torn panties above my face. "This is what little fuck sluts like you deserve, I'll teach you to go teasing men in your little panties" he hissed at me. "Oh Sir they were my favourite panties." I cried. He grinned at me held them up and looked at them and said mockingly, "Aww, did Daddy rip your favourite little panties huh?" He moved up over me till his cock was right above my face, he wrapped my torn panties round his cock and rubbed it against my face. His cock was soaking with pre cum and wet my skin. He forced his cock into my mouth and held my head.

"That's a good gurl, you suck Daddy's cock real nice" I almost choked as he leaned over further and made me take it deep in my mouth.
His cock was so thick it filled my mouth completely, he didn't care that I was struggling to cope and continued to fuck my mouth. I ran my tongue under the tip hoping to make him cum so his assault would stop but it didn't work as he had no intention of cumming in my mouth, it was my bum he wanted to fill with his cum. He withdrew his cock to my relief and threw my torn panties in my face. "Now I'm going to fuck your little ass girl." he growled as he grabbed my ankles. I began struggling again but he easily over powered me and soon had my stockinged legs up on his shoulders. He laid his weight on me and I felt his cock right at my hole. "Oh please stop Sir." I pleaded as his wet cock began to slide inside me.

"Shut the fuck up slut." he shouted as he pushed his cock harder against my little hole. "Oh Sir please don't rape me" I cried but his cock suddenly slid past my tight little opening and a second later it was inside my bum. He held me tight and my struggle only server to help it go in easier. "Ahh you feel so good little slut" he said as he worked his cock in and out until it was easily sliding deep inside me. I felt so helpless, he was raping me and there was nothing I could have done to stop him. He fucked me slow but hard, holding my throat and kissing me.

"You like being raped little sissy, I know you do you little fucking whore." he said as he fucked me. "Oh Sir please be gentle with me." I pleaded as his cock slid very deep inside my tight bum. "Shut the fuck up you little slut." he barked as he grabbed the remains of my panties from beside my head and stuffed them into my mouth as a gag. 'You had better get used to this as me and the boys are gonna rape you when ever we want, do you hear me gurl?" I nodded unable to speak with my mouth full of my panties.

He picked up his rythm, my little feet in my schoolgirl shoes were either side of his face leaning against his strong shoulders and he was able to go so deep into me. My tight little bum must have felt good as he only lasted about a minute before he started cumming. "Oh yeah little gurl, Daddy's going to cum deep inside your sweet little ass right now" he said as he forced his cock as far inside me as he could. I felt his body tense and his thick cock throbbing inside me as he began filling my tight little hole with his cum. He pulled my panties from my mouth and kissed me hard, his tongue invaded my mouth as he kissed me, his cock still throbbing deep inside me, pumping my bum full of hot cum at the same time.

He laid his weight on me almost crushing me as his orgasm faded, his cock was still buried deep inside my bum, my ankles were still on his shoulders. He kissed me again but gently this time, his kiss was almost loving, as if he cared, but he didn't care for me, he was mean and evil.
He stood up, I remained on the floor to get my breath. My rape was over and I was mostly unharmed although I had red marks on my legs where he had torn my panties from me and my bum was sore from the spanking but it was nothing I hadn't been subjected to before.

I looked around the room and saw the dress all torn to shreds, it seemed like a waste of a nice dress but he had paid for it and enjoyed ripping it off me.
He switched off the cameras and removed the memory cards as I got dressed back into my boy clothes. He took my torn panties and stuffed them in his pocket.

"Well lets hope the cameras got the action there boy, there are a lot of men who will enjoy seeing that" he said as I dressed. "I would like to see it too Sir and the video from the other night when all the men were there." I answered. He assured me that I would get a chance to see them soon.
We left the trailer and he drove me home.

To be continued    Open to ideas for the sissy boy's next encounter, please email with ideas for chapter two to come.