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Interracial Sissy Story


(Some prior notes about me, this story and my writings: If MALE bisexuality, crossdressing or interracial sex bother you, don't even bother reading this further, much less commenting. Many have had secret fantasies about what it would be like to be the opposite sex, during sex. Some of my influences for writing this story were things like those fantasies, straight interracial gangbang porn flicks, a strong fetish for female cigarette smoking, strip clubs, hard rap/rock music, an overactive imagination and a weird, corny sense of humor. If you're easily offended by "low-class grammar", simply read some other shit. I often say "cunt" or "snatch" instead of vagina. I say "cock" or "dick" instead of erection or whatever. I may often use casual cursing. My shit's a bit different than the same ol thing, and not for everybody. If you're an average erotica reader, or uppity "grammar Nazi", you may not like it. If you're into strippers, hardcore pornography, or raunchy unashamed aggressive sexuality in general, and like "over the top" stories, then feel free to read and let me know what you think.)

11:39 PM. Friday night. I gathered my breath really nervously as I tried to gather my courage and...oh, yeah. Where's my manners? Let me fill you in on some of the small details and background leading up to the situation that was going on. So , uh, where to start? First, my name is Brad. I'm 5'4", 125 pounds, long brown hair, deep brown eyes, and whenever I intently "forget" to shave, as was the case at the time, a nice bushy beard. I'm 28 years old, but most people only guess me for 19 or 20, when shaven. Good genes, I guess. Skinny build with an average endowment, cute full lips that look like they were made for sucking and a cute round bubblebutt. I had just moved into an apartment with a few c***dhood friends about 2 years ago and everything had been going well. We got along fine. Most of my friends were straight. We were pretty much all "metalheads." I was even the outcast there, also. Half of the time, I would be the only one who wouldn't want to go with them when they went out somewhere. We had also had fights about them telling me to turn my music down. Not exactly that they minded loud music. I just had different musical tastes: I was the only one in the group who listened to Marilyn Manson, 2Pac, and Johnny Cash. I was also the only one who'd ever read anything other than a magazine. But despite our differences, I did have many really good times with them. And, as different as I may have seemed, noone would ever have guessed that I had a gay or bisexual side. However, it seemed that most of them were moving on to other things and seemed to have a bit of direction or a plan.

I, on the other hand, had always been the slacker of the group. They had recently hurt me when they with some VERY harsh words to say the least. So, there I had been, with everyone else out at some club, and me sitting around depressed and drinking, trying to forget myself. But, to my dismay, it wasn't working. I was bumping a Deadlee CD and watching the boob tube, half drunk, when I came across a scene from Shawshank Redemption. One of the gay **** scenes. That, had reminded me of a joke that my friends had told me earlier. When I had joked about my lackluster sex life lately, one of them joked that they would drop me off at Molson Street at midnight and I'd see lots of action. Molson street was a heavy crime area. It was alright during the daytime. But at late night, it was a different story. One of the biggest rumors going around about this area of town said that whenever white people went through there after midnight, they would often end up getting robbed or killed, UNLESS they were taken as prostitutes. Which local legend says included not only girls, but some guys too, who were made to dress like women and get fucked like women. Smaller guys mainly .

Apparently, if one of the "Molson street locals" liked the white guy or gal, they'd **** him or her and then offer them a choice. Be our slut or die. Apparently, rumor has it that the d**g dealers didn't actually mess with any of their own "stuff" or with anything stronger than a little weed or alcohol. They got their kicks from their "hoes" and working out. These guys were built like brick shithouses. People didn't wanna believe these rumors. After all, the law would not let things like this continue, right? However, the area had a very bad rep and people were still very afraid. Well, being inebriated as I was, all I thought was that I was horny. I was still depressed and thinking that maybe my first taste of dick would cheer me up. I mean these rumors HAD to be exaggerated. How much difference could sundown make in a place? Besides, as long as I stayed in line and did as told, I'd have free room and board and d**gs. Not that I did many d**gs. I quit smoking a year ago, and only occasionally drink, now. But, it might be nice to take some more risks in my life for once. Not to mention the free dick and pussy I might get, too. And I definitely was drooling at the thought of my first big dicks, chocolate dicks. And if things got too rough, I could be a scrapper. Not to mention my past training in submission fighting. So I shaved my facial hair and got ready to take a little walk to the "wrong side of town", just ta see what would happen. Alcohol kinda turned me stupid at times. And this is where I will start the story.

So, I gathered my courage drinking the last of the beer I had with me, and stuttering forward. Almost there. A mere ten minute walk away. Slowly walking, I enter the notorious street. Nervous as hell, I start to walk through the city, acting oblivious to cat calls, and threats of v******e. Maybe this was a bad idea. I tend to do crazy things when I've been drinking. But, as I walk fast through the neighborhood, surprisingly, I'm almost at the end and thinking that maybe I'm lucky nothing happened. I'll just find somewhere to hide til morning and find my way back. Just as I thought that, I heard a young female voice scream out "Hey, honey! What the hell are you doing in this part of town? You know how dangerous this is?" I turn around and see this young blonde girl who, as far as I know is only 16. I know because I had used to know this girl from school. But, she had just kinda "disappeared", and noone had heard from her. I didn't know her that well myself, to be honest. She looked "different" from what I had remembered, to say the least. Full lipstick, gorgeous "curly hair, lots of "colorful" makeup and a fur coat. She had a really trashy slutty look, to be so young. Something about her also seemed to be way too mature for her age. She took a drag off her cigarette, and exhaled, looking at me for an answer. I am speechless for a sec and when I start to answer she starts to come up to me and says "How old are you, baby doll?", obviously not remembering me. She kinda smiles at me and invites me to come inside where I'll be safe. I remind her where I know her from as she opens the door to let me into the small building, but as I turn around, she shuts the lights off and closes the door. Just then, I feel some strong, heavy arms grab both of my biceps tight. I turn lightning quick, as if to scream, but a huge hand covers my mouth.

Just then I feel another hand strip my pants off as the guy holding my arms pushes me onto the floor. I can't believe that this is actually happening, and scared senseless, but still aroused at the same time. He's on top of my back breathing heavily and I then feel something unexpected. I feel a cockhead that is MUCH larger than I expected and much wetter, as if it's been oiled up prior to my entering the room, poised at my backdoor. I struggle to reach my feet as I mock like I want to escape. This does not feel as I expected, at first, but much more painful, as it doesn't fit smoothly. He pushes and pushes until deep inside me, and I can feel him almost automatically cum inside my quivering ass. As he pulls out, I feel the other hand pull some chemical coated cloth up to my face. The next thing I know, I'm out cold.

Next morning: "Wake up, hon!" I hear a familiar female voice as I'm splashed in the face with water and completely naked, lying on a bed. I wake quick, looking at the girl who had lured me to this "trap." I start to protest when I notice a gun turn on me being held by a rather large muscular black "thug" at the doorway of the strange bedroom I'm lying in. With a cigarette dangling from her sexy lips, she told me "YOU got a choice, boy. How much do value your life?"

"A lot" I gulp as she takes the cig from her mouth and exhales.

"You don't look stupid. I don't think that you came here by accident. Noone local or in their right minds really does. It's alright. So, I guess I already know your choice." she says.

"What choice is that?"

She smiles and scratches across my chest with her nails. "Be the little slut that you know you are."

"Or?" I continue.

"Or don't." she tells me casually.

"What happens if I don't?"

"I think you already know the answer to that one, don't you?"

"Will I be safe?" I ask.

"You have nothing to fear from anyone here, as long as you remain loyal." she says.

"Loyal to who?" she asks.

"I know that you've heard the rumors. Well, you will meet your bosses tonight. And believe me, as long as you continue to put out, you will not undercome any physical harm. The last guy that hurt one of us paid the price, heavily."

"Well, what do I have to do?"

She then smiles big and tells me "Just stick with me. You have a big day ahead of you. By the way, my name is Jewel. As head whore, I will be training you. During the daytime, you can dress as you normally would, if you so choose. But, come nighttime, you must be prepared for some 'hard work'. Your name?"

"B-Brad" I reply, nervously.

"Well, Brad, first rule you must learn is that with your male masters, your only name is 'slut'. For your first week, this is how I will refer to you. This is your initiation night. You won't work til you pass. Girls?" She turned to some other sexy girls, and boys dressed like girls who had been standing far behind her.

"Yes, m'aam?" one of the girls said.

Jewel kissed her hard and deep on the mouth. "You taste like pussy. Been playin with Michelle again, haven't you, hon?" The girl just smiled shyly and nodded, as if embarrased. Jewel continued "Well, you know what to do, girls. I'll be back in a few hours".

"Yes, m'aam." As Jewel leaves, the other girls tell me to follow them. I could not believe how mature and experienced acting Jewel was to be her age. But, that confident sexuality and sluttiness from such a young little thing was already becoming a huge turn on for me. I knew that I would have to have her. As I follow the girls, I am led into a bathroom with a tub full of water and shaving razors and shaving cream surrounding the tub. The girls have me step into the tub, as they proceeded to bathe me, shampoo and condition my hair and shave my entire body bare. I talked a bit with them, and even started making out a bit with one of the other girlie-drag boys. I am told that I will have to learn responsibility to keep shaven by myself on a daily basis from here on after. I am then led back to the bedroom and told to eat, as I am given some bread and some Ramen noodles.

After waiting a bit, Jewel returns. "It's time to study, slut."

"Yes, m'aam" I reply, with a playful pouting look.

She then went into a closet in the room and came out with a pair of high heels. "Ya know, walking on THESE is not as easy as you may think. You're gonna need practice. Put these on and follow me..." I hesitate a moment. "Now, slut!." She hands them to me. "Second rule. No hesitation" I follow behind quickly almost tripping and stumbling in the "new shoes", as I now end up stopping in a small room with a chair in the middle. "Have a seat, slut. You are getting your piercings. You gotta have both ears, your tongue, nipples, belly, and cock done. Just be a man. I know you can handle it. You'll grow accustomed to it, in no time." I winced and grimaced, but when it was over, I was told that my day was just starting. I am given studs for all of my new holes, except for my ears. For those, I am given these really gaudy, big effeminate looking earrings to wear. Then, I am told that I must spend the next hour practicing walking in my high heels. I spend a whole hour with Jewel being taught how to walk properly in high heels. Then, once I start to get the hang of it a bit, I am led into the bathroom again. This time in front of the mirror. "I have been giving special instructions for you since you have such a different hairstyle than any of the usual boys we get here. We usually would give you a wig, but obviously, that's not needed with you. Jewel reaches into a drawer and pulls out two neon pink hair scrunchies, and demonstrates to me, on herself, how to put them on to make little schoolgirl pigtails. She then pulls them out of her hair and hands them to me. At first, I get it all tangled. It takes me about ten minutes to actually get the hang of doing this on my own. She tells me to relax and hands me a cig for a sec and tells me to take a drag.

"No, thanx, I don't smoke" I say.

"Rule number three. You smoke. Your head honcho pimp daddy likes all of his little sluts to smoke around him. It's a thing he has." I do and cough immediately, as it had been a while.

She laughs. "First time, huh? Here's the lipstick. Push very lightly, because it's delicate."

I finish putting on a heavy coat, right as a big black guy walks in about 6'2, dark as can be. He looks me up and down and tells Jewel, "You're doing a good job. I can't wait ta break this little whore in. Mmm-mm--MMM!" He slaps my ass and squeezes it. "Continue" he says and leaves.

Jewel turns to me and kisses me hard with a wild look in her eyes, as she shoves her tongue deep into my mouth. Then says "You're gonna have fun, slut. Trust me." She goes on to teach me how to apply makeup, presson nails, eyeshadow, eyeliner. She teaches me how to talk like a woman, helps me practice sucking cock on dildos, helps me loosen my bottom in preparation for the night, teaches me how to smoke and hold a cigarette like a girl, and helps me do or practice various other things. Apparently, rule number four was that I was not to even ask the real names of my pimps/masters. When asked if she was worried about pregnancy, she told me that she was unable to have k**s due to some complications. Seemed a touchy subject, so I dropped it.

Nightfall's about here. I'm given a short time to eat and rest, but not sleep, before the "initiation" begins. Then, I hear a loud deep masculine voice shouting "Yo, get that ho ready and bring her bitchass in here!"

Jewel comes in and tells me to slip on some nylon stockings, a cheerleader's shortskirt, a thong and a bra top. All of which, is in addition to the earrings, piercings, eyeliner, eyeshadow, makeup, lipstick, nails, and high heels. I am also told to try and keep a cigarette lit constantly and drag on it occasionally. "You ready?" she asks me, eyeing me up.

I lick my lips, with my cock as hard as a rock, and reply "I've been ready".

I walk into the room nervous as fuck as about 3 huge black guys are whistling and carrying on, and I ash my cigarette holding it in a very effeminate limpwristed manner. All of them naked with fairly huge cocks standing at full attention. These guys bodies were unbelievable: sixpack abs, huge pecs, biceps that could choke the crap out of someone. And their dicks!!! They must have been 9-11 inches each and thick! The air smells of weedsmoke, and sounds of loud rap music. I recognize it as "Ho" by Ludacris. "School's about ta start, slut. Down on your knees and join your little slut friend. Pay attention. You're gonna be doing what she's doing next."

I get onto my knees behind Jewel, who exhales from a cigarette. "Watch me and do as I do" she winks at me, right before being slapped, playfully but rough, and told to turn her head back around. "Aw yeah, I LOVE IT!" she screams. She then grabs two cocks on her side with her hands and starts licking up and down the shaft of one in front of her slowly. I lunge forward. Jewel lustfully tells me as she licks "Remember, you gotta relax. Don't swallow. Let the spit flow freely. Try not to wipe off all of your lipstick." With that, she starts to slowly go down on the first cock, picking up pace, until drool is flying hard and fast as it gets as wet as hell. At one point the guy held her head still and pumped like a piston, ALMOST seemingly making her hurl. She does the other two for a second, before stopping, turning to me smiling, wiping her mouth, and catching her breath saying "Now---PANT-You try", with her hand still on a wet dick. I start to do as she did, with 2 in my hands, and licking the 3rd. I try my best and am slow at first, but then I start getting into it. I pick up the pace, being every bit as wet as Jewel my first time. Still not used to wearing the nails, but am careful not to break them, as nasty as I get. I was loving these delicious monstrous chocolate treats, as I alternated from one to the next. Tasting them, feeling them, squeezing them, wrapping my tongue with my new studs around them, as I tasted their yummy precum. I started to come off of the head with suction noises and go crazy, with my little pigtails bobbing and swinging in a nonstop motion.

"Daaammn! He loves that dick. Good little sissy." one guy went.

"Fuck! You a natural, ho!" the guy in my mouth, whom was the guy I recognized from the bathroom earlier, screamed before grabbing both of my little schoolgirl pigtails and forcing his veiny pulsating erection down my throat as he came in my mouth, and I greedily gulped every last drop.

I took a drag on my cigarette. "Good to the last drop" I said, exhaling and licking my lips. This guy backed up a bit, to take a breather.

Then it was Jewel's turn to "teach" me again, as i would watch everything she did. This time, she laid her head back down on the couch as one of the guys dangled his massive member above her face like bait for a fish. As he lowered into her mouth, she took another drag from her cigarette, exhaled around his fully engorged dick, and started moaning. I seen the way that she used her lip muscles to pull the cock further down her throat, as she winked at me. After another minute of moaning and sucking from her, it was my go again. I assumed the position, took a drag, exhaled, stuck my newly pierced tongue out and opened wide (And I do mean WIDE-Mmmmm!). He slapped me hard, spat a long line of spit onto my face, and said "That's it. Open that dirty little mouth, slut, so I can fuck that face." His slap was so hard that the side of my face almost felt numb for a sec, but I didn't mind. In fact, I loved it.

"Oh yeah! Treat me like the little white trash slut that I am. Feed me that big, black dick!" Everyone else laughed and whistled encouragement at this. I quickly stuck my tongue out again and he started lowering into my wet mouth and as soon as the head was in, I started sucking it and moaning loud and reached both hands up grabbing and stroking the rest of the length. The radio song changed to 2Pac's "How Do U Want It?", as I started moving my head to the beat. Then I imitated Jewel's move and used my lip muscles to pull his cock down further into my hungry mouth and throat. I went insane as I gagged myself on his dick, and for the second time, I outshined the teacher. As I sucked, I could feel his massive erection pulsating and I instinctively knew what was about to come, or cum. This guy, like the other, also came in my mouth, hard. He pulled out as my lips slowly slid off of his dick. I savored every drop.

Jewel said smiling "Competition, I like, I like." Last guy was up. I was wondering if I was gonna get fucked soon. Then she dragged on her cig again, and he leaned in to kiss her hard, before pushing down on her head forcing her to her knees, where she opened her mouth and he spat in it. I was remembering what she had taught me earlier. Arch your back and maneuver right and you will be able to go further on the deepthroat. I seen her hock and spit on his dick, then start to deepthroat using this method. After going down DEEP a few times, I thought that there was no way that I could do that. The guy came hard right at that moment, blasting her face. "1 for me" she smiled. Right then, though I went back to the second guy who was hard again, as he downed some Hennessy straight from the bottle. I sc****d my nails lightly across his ripped perfect chest, and started kissing down his chest, towards his rock hard abs, devouring his dark chocolate body along the way. I tried unsuccessfully to duplicate her act, but was unable.

"You'll get it, slut. Practice makes perfect." the guy said as he pulled me off, and shoved me back to the ground. "Yo, nigga. I'm ready to fuck. Y'all ready?"

"Let's get this party started" came the answer from the first guy. He then walked to the stereo and pushed a few buttons. The song "Shake Ya Ass" by Mystikal came on. "First, let's get a little tease. Dance bitches." Jewel and me immediately started dancing like I had seen strippers do many times, shaking my ass to the beat. They slapped my ass, sending waves through it. As me and Jewel did this, about halfway through the song, they were rubbing baby oil all over our bottoms, and lubing our anal cavities.

I was told to watch once again, as Jewel got onto all fours, with the cig just dangling from her lips and the first guy spat on and lubed his dick heavily and put it up to her puckered back door. "You gotta lean back into that shit. He pushes forward, you gotta push back. Ignore the initial pain. You'll start ta enjoy that shit. Believe me, babe. Squeeze your ass muscles on the out motions."

"Yeah, and this shit's gonna be bareback, ho! I want ya ta feel my cum in ya ass, bitch!" I watched as her ass shook violently like jelly from the hard and fast pounding and she screamed bloody murder. She was bucking back into him as hard as he could push forward. Which seemed insane. A few more minutes, they both slowed the pace as he thrusted a few final thrusts into her, while she gyrated her hips in a circular rotation into him, flexing her tight ass muscles with a very hardcore look on her face as her rather large natural tits swung wildly, and this guy came hard into her ass with a loud "AAAAAaaaahhh! Fuck yeah!"

"Watch out, babe. I'm making a comeback."

"Yeah, I just came IN your back slut. Yo, slut numba two, you're up."

I nervously bent over and before I could even brace myself, I felt some other guy grab my thong and pull it aside, and slide his cock into me out of nowhere. He must have snuck into the room behind me. This guy was bigger than the others, which shocked me. It must have been 12 inches, at least, and as big around as a soda can. "Oh, damn, ho, I didn't see ya there", he joked for a second, as I screamed in initial horror and pain. He then started necking me heavily, as he pinched my nipples, and I struggled. Then, he let go and shoved me to the floor, brutally, so I was on all fours. He got right over me and started to shove his cockhead into me.

As soon as he had the head in he shoved in all the way quick and brutal, and started ripping ass hardcore. I screamed like a murder victim at first. My ass was shaking so violently that you could probably hear it outside. He was pulling me back by my thong, and letting go as I pulled forward, in a back & forth frantic rhythm. He slapped my ass a few times and squeezed hard enough to destroy my delicate bottom.Though, it was painful as fuck, I was loving it. He then slowed down after a few minutes, and grabbed my shoulders with a few hard singular thrusts, seemingly trying to thrust right through my delicate little behind. The first hard thrust made me scream like a little girl, very effeminately. then, I came hard as hell all over the floor.

At this, everyone laughed and one said "Yeeeaah, love that black dick, don't ya slut?"

"Yes, sir" was all that I could say with a smile, as I continued to be pounded in my cute little tight asshole. He hadn't stopped, but then grabbed my pigtails in one hand, and yanked hard, picking up the pace once again. I screamed "Ow!" really loud the minute he pulled my hair like that. He pulled out that monster slowly, trying not to cum yet, and it kind of tickled as it came out. I giggled like a teenager. "OOooo, I like, pimpdaddy." I then turned around and blinked up at him a bunch with my colorfully painted deep brown eyes and stuck out my lower lip in a pouty flirting look.

Then, the second guy told me get on the couch and spread my legs, like the cocksucking white trash whore I am. The radio then started playing "He Wantz It" by Gangsta Fag. This guy pulled my legs behind him as I lit another cigarette, and moaned in my most feminine-like voice "Oh, yeah, fuck me hard, daddy! I need some more hot chocolate." Over to the side Jewel and the other two guys were busy watching as he grabbed up underneath my ass and slid me into his dick, hard. With my legs wrapped firmly around him, I screamed like a banshee. After a minute, with feet in the air, I relaxed my legs, as I twirled the high heels around on my feet in utter delight. Then, he grabbed my legs, and d****d them over his shoulders, as he started to choke my neck and pump rough into me in his crazy rhythm. After a few rough, psychotic minutes of slamming my bottom, he came hard with so much cum that it exploded out the sides of my ass, as I cooed in content, having came myself at that exact moment.

"I got one more thing to show ya, babe." Jewel said flicking her cig. The third guy sat down as she sat her ass down on his dick facing away. She closed her legs, rested her arms at the back of the couch and lifting her legs, as he held them and started thrusting upward into her, making her scream. I noticed her positioning and how she managed to stay balanced with a little bit of help.

"We can do that now, slut", the first guy said. He went to sit in a chair, and I then started to lower myself, slowly. "Fuck that slow shit, bitch. Get on this shit" he said as he shoved me down quick to the base, and I tried to keep my legs lifted and together. He started fucking hard as hell and I looked over and Jewel was in the same position, except that she was sucking off the second guy, too. I came immediately on my stomach, as I seen that and my own ass was being slammed up into like a prisoner. Then my view was blocked by the huge dick of the fourth guy who just forcefully shoved it in my mouth from out of the blue, surprising me.

"Fuck lookin over there at that bitch, yo. You gettin yours, too, slut. SSSUCK my big, black dick!" I guess they had built stamina after a few The first guy continued to thrust upwards into my aching ass as I greedily slurped the dark meat in my mouth while also admiring his well toned buff beauty of a body. Then, I pulled off for a minute to suck his sweaty balls, as his monstrous black dick rested against my face. By this point, I had dropped my legs to bounce up and down on the rock hard cock below me. Then, I took another drag off of my cig which I had lied down for a sec, and then exhaled again, letting the smoke curl out from the sides of my lipstick covered mouth in a sexy, erotic manner as the dick entered my mouth simultaneously.

After a bit of being DPed, they told me and Jewel to both get up and get on all fours facing each other, in front of the mirror in the back of the room. I seen guy number one enter Jewel's pussy and felt guy number two enter my soft ass once again. Funny thing is right before they started to fuck, I laughed at the song I heard playing: "We Want Some Pussy." In a weird way, it helped the mood to turn me on even more. After all, I was one of the "pussies" this time. Me and Jewel both took drags and exhaled as we kissed and both of us were getting the dicking of a lifetime. The third and fourth guys then came up to our faces, and I grabbed one in my mouth, as Jewel took the other. I looked at the mirror from the corner of my eye, and loved what I seen. I could see myself all dressed up in my newfound beauty, pigtails and all, as this guy kept slamming into my shortskirt covered ass while my lipstick covered lips were sucking off another. Me and Jewel made a good pair. After plenty of frantic thrusting, all of them came like geysers, filling me and Jewel to the brim with warm, sticky fluids.

This caused both me and Jewel to cum a storm as we locked lips hard. We both had "messy mouths" and lots of cum dripping out of us. Then, the second guy, who was just in me, grabbed me up, under the arms, roughly, and spun me around on my knees. Clean that shit off, ho!" I did not hesitate, and devoured it like an a****l in heat, using all I had learned. "You like tasting your ass, slut?"

I just moaned "MMmm-hmmm", while looking up at him.

"You in, ho. looks like you've passed our initiation with, shall we say, flyin col-uhs." They decided to get dressed at that point, and left us on our own, telling me I'll start "work" tomorrow night, peddling my ass. One of them then stared at Jewel, then at me and winked right before leaving.

As soon as they left the room, I seen Jewel was sitting on the floor, smiling at me, while holding her ass. She looked so hot to me after this, in a barely legal kind of way. It was hard to believe that such a young gal could be such an experienced SLUT. "Goooood joooob. Ya know you make a cute little whore." she said eyeballing me and laughing. I was still horny and couldn't stand it a second longer, so I grabbed her legs and forcefully slid her into missionary position, entering her wet snatch almost instantly, and surprising the hell out of her, making her scream. First time I had been the one doing the fucking all night. She ground her hips against me, as I tried to slam her through the floor, breathing heavily on her neck, in a truly perverted manner. She screamed and came fast, but I still had much further to go. I picked her up, still inside of her, and carried her to the couch, where I dropped her and continued plowing her sweet little teenage snatch, like a madman, as I suckled her big shaking tits like a hungry baby. I finally came like a geyser, as she moaned in satisfaction, and I bent down to lock tongues in a deep, passionate kiss. She tasted like a combination of beer, cock, and cigarettes. I loved this trashy whore, like I had no other. We immediately decided to clean each other off, in 69 position, as I licked my cream from her freshly fucked cunt, and she sucked her pussy juices off of my now softening tired cock.

I awoke that next morning with a "tum full of cum", a sore & aching asshole, a spent cock, and the taste of pussy and dick in my mouth mixed with the tastes of cigarettes & alcohol. This was the first time in a long time, that I actually cared for or had pride in a job. I was a fucking dirty cocksucking whore. And I was loving life. A bunch of things would go on to happen. That night would be my first day on the job. After that one night initiation, I was to be safe as hell in my attitudes about protection. My days would be spent as a normal everyday average crude male, with a little bit of personal time for reading and intellectual improvement here and there too, though. And my nights, I would spend as my alter ego, whom I named "Brandy."

Eventually, "Brandy" took Jewel's place as top whore. And then, my masters eventually found out that I could fight, and I gained a large level of respect from them, even learning their true names, as they put me into pitfights with others for their entertainment. I won many and lost a few horribly. So, for a while, I was spending half my time fucking, and the other half fighting. They even offered to let me quit dragwhoring. But, I decided to still do it for them, on a personal level. I was addicted to the dick. And me and Jewel became the best of friends. Friends with benefits, anyway. I could never resist her sweet little snatch, the whole time I knew her. Anyway, all that's another story.....

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A Very Sissy Love Story

A Very Sissy Love Story by: Missy Satinpanties I guess I've always been bisexual, if not completely gay. I mean, in high school, I lusted after the right girls, and wanted to get into their panties like every other boy, but when I looked at the porno mags we had, I always gravitated towards the girls who looked kind of innocent, and were wearing soft, lacy lingerie. And yeah, I did wonder how all that soft, slippery lingerie felt. A naked girl really didn't grab my attention, at all....

2 years ago
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My Wife Made Me A Sissy But That Is Not The End Of the Story

MY WIFE MADE ME A SISSY, BUT THAT IS NOT THE END OF THE STORY. BY Betty Noone At one point in my life, my wife made me into a sissy. And I was a sissy for a long while. I resisted it at first, but then I began to love being a sissy. Eight months ago if anyone would have called me a sissy it would have been cause for me to try to punch him out. I was a heterosexual male, and was raised by my parents that men are men and women are women. But somehow, after being a sissy I...

3 years ago
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Sissy story

Date: Thu, 11 Aug 2011 16:42:22 -0700 (PDT)From: Danny Smith Subject: A Sissy Story Part 2I got very excited writing the following storyI always considered myself straight. I was married and at 55 my k**s hadflown the coop. But over the last few years I began to fantasizing aboutcocks and being submissive to a more masculine man. I was 6' tall fairlytrim at 175, but with a small 3.5inch cock. I never thought a lot about thesize of my cock until one evening while I...

2 years ago
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Young Sissys Story

Today I want to share with you my story. I’ve finally managed to gather enough courage to tell you about how I became a sissy and what has that meant to me, but before that I'd like to thank xhamster for giving me the opportunity to share my story. I’m very grateful to porn for helping me discover my sexuality and my true nature as a sissy and for helping me develop new tastes and discover new pleasures. Now let’s get into my story. So, as you’ve read in the title, I’m still a young sissy, I...

1 year ago
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INTERRACIAL RIVALRIES IN CONTEMPORARY PORN

We’ve seen in the last decades a particular phenomenon in porn industry, videos, photos and comics: the proliferation of an interracial gender, both on the straight and the gay side, in which most of the time blacks appear dominating whites. The novelty of this genre is to have introduced a virulent racial rivalry in porn, reaching extremes in which white men are ridiculed before blacks, by putting poorly endowed whites side by side with well-endowed blacks. The insane producers of this genre,...

3 years ago
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A sissy story

From the time I was very young, I've known I was "different". I was fascinated with women's and girls' clothing and shoes. Like all little sissy-boys, I loved girlish "dress-ups". But I didn't have to sneak my mother's adult-size clothing, because I had a sister who was my same size -- my fraternal twin. And she didn't even mind when I tried on her things! I'm Christopher, by the way, and my sister's name is Andrea. I usually went by "Chris"... but when she and I were alone, and I was being...

1 year ago
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Interracial Blowbang

I’ve always had an Interracial Blowbang on my bucket list but, well, I’ve just never been black enough. Maybe one day they’ll change the dynamic and let a gaggle of pasty dudes bang an ebony pornstar, but until then, I’m pretty happy with all the one-on-one action I get over at PornDudeCasting. Anyway, the magic of the internet and the world of porno is that most of your fantasies are just a couple clicks away. Until I’m able to sprout a BBC for myself, this next site is where I’ll watch pretty...

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4 years ago
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Interracial American 2021Chapter 4 Dr Omar Kings Interracial Theory

Dr. Omar King addressed the Black Panther army about the new White girls that had been captured in the battle at the last university protest. Over 50 eager White girls who all wanted a Big Black Cock. “MY brothers! WE have defeated the racists. But did you know! We have also captured 200 White bois, who we can prove are all addicted to interracial sex!” A roar of crowd from the strong Black Men in thr crowd greeted Timoth’s ears as he was shoved to his feet becoming very conscious again...

3 years ago
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Sissy Girl Chrissie A Chrissie Conway Story

Sissy Girl Chrissie A Chrissie Conway Story I had come home from college for a long weekend and with my mother being out of town I figured I'd stay at her house.Had my mother been home I no doubt would have elected to stay with Kelly's mother. That's just the kind of relationship my mother and I had regressed to by this time. Anyway, I had the entire house to myself and was looking forward to a nice relaxing weekend. It was around midnight and I was finishing off a bottle of Chablis...

2 years ago
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How I Became A Sissy For BBC True Story

I started watching a lot of interracial porn when I got my own house. I also started taking a lot of Adderall which made me really horny all the time. I somehow stumbled onto sissy porn and got really into it. Before long, I wanted to dress up myself. I went out and bought some panties, stockings, and a garter from Adult World and began wearing it around my house. When I was particularly horny, I would take pictures and post them on Craigslist. I would always get a ton of replies, but I was...

3 years ago
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Sissy Fucked In Adult Book Store True Story

100% True Story.I was 19 years old and working 3rd shift at a department store and taking classes during the daytime. I had visited an Adult Bookstore about 15 minutes away a few months back and went back into the video booths. It was the first time I had even been in an adult video arcade and wasn’t really that impressed. There was a strip club next door and I had heard stories of hookers giving guys head at the bookstore video booths. I realized that turned out not to be true. I was pretty...

2 years ago
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Long Hard Weekend a sissy story

Long Hard Weekend(A sissy story)I was tied to a chair. The chair had an open back and my ass wassticking out exposed. My ankles were tied to the legs and my waist tothe back of the chair. My hands were cuffed and the cuffs wereattached to a collar around My neck. As if this weren’t badenough I was wearing pink silk panties and stockings. I am a man(or Iused to be) 5’5" 135 long blond hair and blue eyes. I have never hadto shave and have a smooth almost hairless body. I have always beenteased,...

2 years ago
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Mom forces Me To Take Cock Sissy Pussyboy story

Mom forces Me To Take CockIf you don't already know, I'm a pathetic 31-year-old pussyboy son who is regularly dominated by his whore mother. Today she stood towering over me. I was on my knees in front of her, my nose pressed against hard against her skirt, in-line with her pussy. It is very prominent pussy with big, fleshy fat pussy lips and a large swollen clit and I love the fact that her pubic hair is now so sparse and thin that it looks like a shaved pussy. I am a slave to her magnificent...

3 years ago
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Interracial fantasies 2

“Is something the matter with your relationship?” “I’m sorry Jerome. It’s something I can’t talk about right now.” “Well, if it’s a guy sort of thing than maybe I could help but I’ll let that be up to you.” Jerome didn’t question Danielle about their problem as they finished lifting weights and walked the tread mill together. Jerome was surprised when out of the blue, Danielle asked Jerome a serous question about men....

4 years ago
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Be carfull what you wish for part 1 a sissy story

I was about 22 and i was crossdressing for a few years now. Always hidden and only in my room. I often took pics and postet them on porn sites. It gave me a real kick to get strong man turned on. The rest of my life i was just a normal student boy still living at his parents and nobody new about my hobbies or would even suggest that im not straight but that changed soon.... Maby it were the sissy hypnos but soon my desire for cock became overwhelming so i started looking around on dating sites...

4 years ago
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Interracial Porn gets her to try the Reel Deal

I have watched porn before. Not once and certainly not twice. I can't say that I've enjoyed it — how many women out there would ever profess that they do? But since Brad and I hooked up, that's all he's been getting me to watch Porn.Not just any type of porn. I won't be writing this if it was the garden variety type of porn. You know, like the ones that comes with a story (a Pizza-delivery guy knocks at a door. A buxom blonde bimbo opens and invites him inside. He opens the Pizza box and she...

4 years ago
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Sissy Hotwife Spa Story

I have booked us a room at a nudist spa just off outside London for a couple of nights.Before we go there we do some shopping, you choose some stockings, knickers and a little mini skirt but they are not for you, they are for me. We also bought a dildo, lube and condoms.We go into the spa and are showed to our room and drop our gear. We strip off and make our way down to the spa. We go out into the wet area and start with a swim and splash around naked for a while. Then we go to the steam room...

4 years ago
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2088 Its a Sissy World

2088: It's a Sissy World Charles Pauline - Data Processor Cindy Pauline - Charles' wife Ms. Miriam Jensdotter - Charles' Boss James Marie - Charles' work friend Ms. Marysdau - James' boss Creampuff - A Sissy Store Worker Babykins - A Sissy Store Worker Suzi - The Sissy Store Owner Butterscotch - Creampuff's Roommate Supervisor Gabriellez - Creampuff's Apartment Supervisor Janice and Roger - Passengers on the Looper Ms. Hardcastle - Milking Salon Director Nurse Hamilton - Milking...

3 years ago
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Meinen Mann zur Sissy erzogen

Achtung diese Geschichte ist noch voller Rechtschreib- und Gramatikfehler. Jeder der m?chte kann diese Geschichte als Vorlage nehmen und sie verbessern. Jetzt reicht es mir. Ich hatte die Internet Seiten meines Freundes gefunden. Er surft also st?ndig auf Adult Baby Sissy Seiten. Ich hatte mich schon l?nger gefragt warum er im Bett nichts zu Stande bringt. Das kann er haben, ich werde ihn einfach in ein kleines Babym?dchen behandeln bzw im Grunde verwandeln. Er war eine Woche zu einem al...

1 year ago
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Chrissie The Saga of a Lovestruck Sissy Maid

Chrissie by c.w. cobblestone BOOK ONE "Mrs. Martin" Part I My right leg had a mind of its own. Rebecca frowned. "Why you keep bouncing like that? What's wrong with you?" "Um, I ... I ... nothing." "Bullshit, nothing. Something's up; you been acting weird ever since we got back from Paris. What the hell's going on, Chris?" I balled my fists. Clenched my jaw. Closed my eyes. Drew a breath. Took the plunge. "Okay. Okay. It's just ... well, now that we're...

2 years ago
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Sissy spit roast sleep over

Pt 1: Long black limoSissy Saraya was very excited because her new mistress had told her they were going to continue with her corset training tonight, she had been wearing her waist trainer and inflatable plug all day along with her favourite pink maids outfit and cute sissy 6" white heels and stockings with pretty pink bows, She had been watching BBC porn all day and was dreaming of cock while she finished her chores, Mistress text to say her driver would be arriving at 6pm sharp, Mistress...

2 years ago
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The SissyMaster

THE SISSY-MASTER CHAPTER 1 I have read many tales and stories on this site over the years; some of them 'autobiographical' and some of them complete fantasy. It strikes me that most of the stories have been written by the, either real or wannabe sissy girl and therefore is 'her' fantasy from a sissy's perspective. So I have written my stories of my experiences, beliefs and methods from the perspective of the male. This is for the REAL MEN that read this site, a guide to the...

3 years ago
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The Sissy App

The Sissy App 1. Setup "This is the longest user agreement I've ever read!" thought Rick as he scrolled and scrolled through the hundreds of pages of legalese on his recently-downloaded smartphone app. The "Sissy App" User License Agreement was indeed voluminous, containing numerous sections detailing the GRA Software Corporation's exemption from penalties, payments or legal requirements, granted by authorities or statutes, for any harm that may come to a user when using the Sissy...

4 years ago
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A Sissy called Jezebel Part VIII

A Sissy called Jezebel Part VIII - Jezebel has returned to hir classes at Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We are all getting an education on the Matriarchy in hir sissy life skills class. (Authors note: We are definitely at that world building point, where I really let my imagination fly off the hook. I am throwing out a lot of ideas, but hopefully in...

2 years ago
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Adult Sissy Little Girl World

Journey Into A Special World My name is Hannah Stone. I've been a reporter for a newspaper for years. A couple of days ago I ran into an old sorority sister and good friend Linda Hart. It's been a few years since we last saw each other and we decided to do lunch together. At the beginning of lunch we had the usual light chat. Then we sort of got on the serious side of chat, when I asked Linda how her marriage to Bob was going. "Oh, Hannah I divorced that bastard years ago. He was...

4 years ago
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Forever Her Sissy Chapter 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. I Absolutely love reading the reviews that you wonderful readers have been leaving, please, please, please continue to write and post...

2 years ago
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Training Sissy Michelle

I first became aware of "Sissy Michelle" back in the old Craigslist days. She would pop up in the T4M section, advertising herself as an older but very horny sissy looking to serve a group of kinky guys. She said she was interested in all sorts of kinky stuff, everything from group sex to watersports to hypnosis and lots and lots of bondage. She practically begged to be photographed and blackmailed into doing all of this. Here's an example of one of her ads that piqued my...

4 years ago
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Tweak Chapter Four Whats A Sissy To Do

What makes a sissy happy? What makes a sissy's Mistresses happy? It's complicated. Author's note: Although I'm posting this in serial form, I assure you, dear reader, this humble offering consisting of eight chapters, is complete. "Tweak" By: Simonne Danielle © 2008 - 2010 All Rights Reserved Chapter Four - What's A Sissy To Do "You have made your Mistress very happy, sissy Simonne. Let's see if we can't make you just as happy." She led him to the bedroom...

3 years ago
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Cocky Weewee Peepee Sissy Slut Training The Bladder Test

This is one of the sets of stories I am currently writing. The set is called Cocky, Weewee and Peepee Sissy Slut Training. These sissies are in the hands of Mistress Katrina, Mistress Heather and Mistress Satin. Sometimes Master John and Master Rick are involved in their training. Many situations await them. MANY! If these stories succeed I will add some prequels and sequels. Hope you enjoy it! English is not my native language! I will do my best! Sissy Joan Cocky Weewee and...

3 years ago
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Good Sissy Girl

Good Sissy Girl. I kept pressing myself backwards. Not much further to go now, I could feel the flare really stretching my lips now and that meant I was almost there. As the plug's biggest width popped past my sphincter and went all the way in I shuddered all over. It felt so full. It felt so good. "That's a good girl. Allll the way in..." my Mistress purred at me. I loved seeing her this excited. I loved turning her on. I loved that transforming myself for her turned her...

4 years ago
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Sissy School Part 3

SISSY SCHOOL - PART 3 By Missy Crystal After Sissy Heather had swished and drooled a couple of more times, she began to give me gentle nibbles and licks to clean the cummy residue on my lips and chin. After the kitty bath, she stood up. Since her crotch was now at my eye level and since her short skirt exposed her frilly panties, it was obvious that I wasn't the only one that got turned on by her sucking my dick. She must have been aware of it too, because she pulled her panties down...

2 years ago
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Sissy tasks

Your First Sissy AssignmentThis is your first step on your journey into femininity. A journey that will change your life. You will be humiliated and embarrassed. Most of all, you will be feminised. If you don’t intend to follow all of these assignments to the letter, then turn away now.Your first assignment is to buy yourself a pair of panties. Be sure to measure your hips before you set off. You will go to a smart department store or, better still, a specialist lingerie shop. How exciting – a...

4 years ago
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She Found a Sissy

She Found a Sissy ? by: Donna Sash She had been working at Bardwell's for the last 10 years. Five years ago she Had moved to the scarf counter and had been there ever since. Sales had gone up because she really likes it here. From the time she was a little girl she always loved wearing a scarf with her outfits. Now every day she wore a different one on the job and it helped sales. Women reacted well to someone who believed in their product. Some women just wore a scarf...

4 years ago
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100 Sissy Points

Author's note. This is a work of erotic fiction, so if this offends you, please stop reading. Also, most of what's described in this story wouldn't be ethical or legal, but again, I remind you that it's fiction! I hope it's good-and-kinky fiction, and while I wish something like this had happened to me, once again, it's only fiction. Some readers think that my stories are autobiographical. I wish! Also, a fan of my work suggested this story concept. Feel free to message me if you have...

4 years ago
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Welcome Your Now a Sissy

Are you ready?Are you ready, princess?It's finally time. It's finally time, princess. It's time to begin. Are you ready? I think you are, princess. I think you're ready. I think you've been ready for so long.You've been ready for your whole life princess.It's time to drop the mask and be who you are. Who you really are. What you really are. No more lies, princess. No more games. It's finally time to reveal everything.It's time to reveal the sissy.That's right, princess. You are a sissy. Say it...

4 years ago
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Femocracy A Sissy Maids Tale

The year is 2050 and women rule the world. I should really follow this statement with a sinister laugh but there was nothing sinister in the current situation. There was no bloody coup by women to overthrow man, there was no war waged by man to wipe himself out, no it was mother nature who took a hand in helping women find there rightful place. Things started changing from the year 2012. Gradually women began to realise that they could read minds. They could easily read the mind of a man...

2 years ago
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A sissy called Jezebel Part II

Part II - Jezebel goes to school, the Templeton Academy: where young womyn become dominatrixes and sissies are crushed into submission. We meet some of hir friends, hir Instructresses, and hir bullies. I exit the gate and head to the main road. We live in a giant gated community, with families that are only 'in the know.' Families that have sissies or otherwise dominate men. A sissy waiting for the school bus, is just something you see. No biggie. One of my neighbors, Dorcas,...

4 years ago
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407am Sissy

My phone buzzed at 4:07am. I roused myself from sleep to look at the text message because somebody only sends you a message that early in the morning when it's important. I was right. That text message would be the start of a life-changing series of events. It simply read "Good morning, sissy slut." It was followed up by a picture of me, on my knees, wearing a bra, panties and stockings while sucking on a very hard cock. A second picture followed showing my open mouth, filled...

1 year ago
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Milking Sissy

The bondage wasn't necessary. The straps are there really as more of a ritual and now something I took comfort in due to its familiarity. My make up wasn't necessary either. Well, not really. But I no longer face the day without having at least some lipstick on. Thanks to what my Master had tattooed, I usually don't need much more than that. When it's time for my milking however, I like to make sure I'm as pretty as I can be. Especially if my Master decides to make use of me while...

3 years ago
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Unexpected Sissy Transformation

An Unexpected Sissy Transformation My unexpected transformation actually began at the company Christmas party, when Jennifer, our HR Manager of all people, sauntered over to me with an odd smile on her face. "Merry Christmas, Sean," she said, never taking her eyes off my face. "Do you mind if I ask you something personal?" Here we go again. I am an out gay male living in Texas. I can't tell you how many women have quizzed me about my "fabulous" gay lifestyle. The truth of the...

1 year ago
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Sissy and Paul

The double ended dildo had appealed to her sense of humour and made her wet thinking about using it on me. Sissy and Paul Years ago life was very different to nowadays, for a start pubs shut at 10.30 unless they had and extension for special occasions, they had different bars such as the main or public bar, the lounge and sadly no longer, a room called the snug. This room was usually used by the 'older generation' or people who wanted a bit of quiet/privacy. We had married several months...

Mature
3 years ago
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Sissy School Part 6

SISSY SCHOOL - PART 6 By Missy Crystal The sissies flounced out of the kitchen in a train of swirling petticoats and went into the living room, which was also the classroom. I was the caboose, following Sissy Heather. As soon as we were all in the room, Mistress Mary appeared. Either she had ESP or she really was constantly monitoring us. Either way, I was glad I decided not to try anything for the time being. "Today we will have a deportment class," she announced. "Yeth, Mithtwith...

3 years ago
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Sissy Farm Chapter Sixteen

Sissy Farm - Chapter 16 By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

4 years ago
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Interracial Sex Bonanza for a White Boy

I've always appreciated the aesthetics of interracial sex. The contrast of skin tones, and all the taboos as well, which increase the excitement factor. Doesn't matter which way, I love black guy on white girl and white guy on black girl porn alike. I'm a thirty-one-year-old white male, so looking for black girls was the easiest way for me to dabble in the scene. On dating apps, I tried to match with the ebony goddesses in particular and eventually started talking with a nineteen-year-old. She...

Interracial
2 years ago
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Interracial fantasies 1

Danielle stood in front of the full length mirror in her neighbor’s bedroom frantically trying to zip up the new dress she brought. “Macy. This dress is extremely tight. Help me zip it up!” Macy crossed the room and finished zipping up Danielle’s dress, bringing relief to her blonde neighbor. “Danielle. What size is that dress anyway?” “It’s a size three but I guess my boobs must have grown a bit since this morning.” “Danielle....

4 years ago
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Interracial American 2021Chapter 2 Brutus Bull

Brutus Bull pressed his big Black Hands around her shapely ivory thighs, her beautiful derriere coming full into view. Her thrust his huge ebony god cock in her sweet pink pussy and asked her softly, “What’s inside your cunt?” Brutus continued to thrust passionately smiling at the beautiful white wife on her hands and knees on the bed, “What’s inside your cunt!” he commanded. Bella Everett replied, “A Black Cock.” She stammered as he thrust, her shoved down in the pillow. It was a wonder if...

3 years ago
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Sissy School Part 4

SISSY SCHOOL - PART 4 By Missy Crystal Mistress Mary came over and stood next to us. To my surprise, her voice was calm. "The purpose of discipline is correction, not cruelty. There is nothing to be gained by punishing a sissy for behavior that cannot be improved and no profit in breaking her spirit by making her fearful of mistakes over which she has no control. I do not require perfection. Only that each sissy tries her best to be perfect. You have always done so, Sissy Heather."...

2 years ago
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My Daily Sissy Schedule Part 1

My Daily Sissy Schedule I met Daddy online a little more than a year ago. He lives about five hours away from me, but promised that despite the distance, he could help me become the perfect sissy slut if only I would agree to follow his schedule for me. I readily agreed, and started down the path to becoming his perfect sissy whore. Here's a peak at my sissy schedule, just in case there are any other sissies out there looking to add a regimen to their life. I wake up every morning...

4 years ago
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Forever Her Sissy Chapter 5

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 5 The ride home was wonderfully uneventful. So many things had happened today, It had been confusing and...

2 years ago
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My Sissy Calling

My Sissy Calling Like many recent college graduates, I found it hard to get a job after I received my super-impressive English degree. Sure, the job market was tough and my degree wasn't going to open any doors, but part of the problem was that I still didn't have any idea about what I wanted to do with the rest of my life. I was looking for a calling--something to give my life meaning. I thought that I would find it in college, but it never came. Well, that's not exactly true. I...

1 year ago
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Sissy Farm Chapter Eleven

Sissy Farm - Chapter Eleven By: Beverly Taff List Of Characters. Me: Michelle - A Natural transvestite sissy. Janice: My Younger sister Aunty Bev: Janice and My mother's Sister. Mistress Janet: Headmistress of the young lady's academy Dr Shirley: My endocrinologist. Miranda: A very effeminate Sissy sales assistant. Miss Stern: Miranda's mistress who owns the shop. Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's brother.) James: AKA. Auntie...

2 years ago
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Sissy Emma is turned

Sissy Emma is turnedI had been a crossdresser all my life but completely in the closet and hidden from all my friends and family. To ease my tensions, I often chatted with people on line, at first with females and other crossdressers but as I got braver with men as well. I loved to chat with them and their strong demeanour made me feel even more feminine.I had been chatting with John for a couple of weeks, about my fantasies. And let me get this straight, that's all they were fantasies. I mean...

2 years ago
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99 Sissy Stories

99 SISSY STORIES by Throne I've read about things like this happening but never thought I would experience it. My wife Grace discovered my stash of TV magazines and all the pictures I'd clipped out of her discarded catalogs that showed fashions I liked. She had me trapped with no way that I could deny my guilt or convince her that I wasn't attracted to wearing those things. She sat me down on a footstool in our den and stood in front of me. She has a sweet girlish face and an...

3 years ago
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My Sissy Schedule

Author's Note: Another reader request, this one from a fellow sissy who enjoys when I write about a daily routine that helps keep me in a sissy headspace all day long. She requested that it be detailed enough to seem plausible, should somebody want to start following the schedule. And of course, it should spiral out of control so that her sissy stick throbs in her panties. I'm always happy to oblige. I'm left wondering if I could actually follow such a sissy schedule. It would sure be...

2 years ago
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Forever Her Sissy Chapter 4 of 6

This is a work of fiction for your enjoyment and all the characters are fictional. Please practice safe sex, respect others limits and know that bondage and discipline can be dangerous if done to extremes. None of the scenes in this literature are meant to be reproduced in real life. Be respectful to all women and to local ordinances and laws. Forever Her Sissy - Chapter 4 More shopping? I thought to myself. How much more of this could I take. "Mrs. Karen?" I spoke...

2 years ago
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The Sissy Contest

Author's Note: This is a quick one off story written from a reader request. I was especially motivated to write this as a genuine sissy training fantasy, with the hopes that somebody would read it and use it as a blueprint IRL. That certainly got my clittly interested! Enjoy! And as always, please feel free to comment here or contact me directly at [email protected] xoxox Emshoninque The Sissy Contest My phone rang just after 3am-caller unknown. I normally don't answer...

2 years ago
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Crowd Sourced Sissy 3

PREVIOUSLY ON CROWD SOURCED SISSY: In part 1, a man met a sissy exhibitionist while on a trip to New York. She has a website (something like OnlyFans) where her admirers request that she perform kinky acts and tip her for posting videos of her completing these tasks. In part 2, the man decides to become a sissy as well. He travels to New York with visions of sissy in his head, but the anonymous Master who is controlling his fate has other plans for our poor sissy. Crowd Sourced...

4 years ago
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Sissy Farm Chapter Eighteen

Sissy Farm - Chapter 18 - By: Beverly Taff List of Characters. Me: Michelle - A Natural transvestite sissy; Janice: My Younger sister; Aunty Bev: Janice and My mother's Sister; Mistress Janet: Headmistress of the young lady's academy; Dr Shirley: My endocrinologist; Miranda: A very effeminate Sissy sales assistant; Miss Stern: Miranda's mistress who owns the shop; Peregrine: AKA. Uncle Penny. My transvestite uncle, (Aunty Bev's...

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