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(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 d***k, 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 sl**p, 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. ŕ 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 bl**dy 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 f***efully 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 f***efully 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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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...

1 year 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...

3 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...

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...

2 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."...

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...

1 year 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...

3 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...

2 years ago
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Sissy Hypnosis Fun

Sissy Hypnosis Bet I have always been something of a night owl, which means that I take a while to get up and going in the morning. My alarm generally goes off at 7am, I hit snooze two or three times, then I finally get up and hop in the shower while my coffee pot starts to percolate. I grab my coffee and try to head out the door by 7:45, which is just barely enough time to get me into the office by my 8am start time. Needless to say, I frequently arrive with my hair still wet and...

2 years ago
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Sissy gets a black master

Sissy Gets A Black MasterI got up wearily from my long and exhausting night being fucked andpunished by my new Black Master. As I awoke, I could scarcely believe thatall those depraved things had happened to me. One minute I had been merelyexchanging emails with a man, who could have been anywhere and the nextminute, that very man was at my door, in my home, and then inside mybody. Black Master, a man whose name I didn't even know, a man who lookedto be about ten years my junior, had taken me...

3 years ago
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Sissy Training at Last

Sissy Training at Last The email came at 3pm on the Saturday before my birthday. All things considered, I have to admit that His timing was perfect. I'd just returned home, and as I had the rest of the weekend free, I'd decided to have a little fun. For me, "a little fun" meant that I'd indulge in some sissy fantasy play. You see, I've been a closet sissy for years, and even though it's my main sexual kink, I hadn't really found anybody who wanted to make my weekend fantasy into my...

3 years ago
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Sissy Farm 20

20 Sissy farm 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 Doctor Shirley Williams. 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 Jamie Peregrine's...

1 year ago
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Sissy Farm Chapter Fourteen

Sissy Farm - Chapter Fourteen 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...

4 years ago
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Sissy Velina

I walk into the living room of my master. I am completely sissified and wear a very frilly sissy maid outfit. My 6" white leather peep too high heels have thick leather straps around my ankles and are closed with medium sized padlocks. I wish I knew where my master holds the keys. On my lightly sun tanned and smoothly shaved legs I wear white sheer seamed stockings and with a nice lace band at the top. At the back the pink seams end with large pink girly satin bows. Just above my...

2 years ago
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Sissy Rules Reads like a proper job description

(Found this on the internet... #65 seems especially made for me) Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows...

1 year ago
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Sissy Rules

Rule#1: A sissy does not have a cock. A sissy has a clittyRule#2: A sissy wears a bra and pantiesRule#3: A sissy loves cockRule#4: A sissy loves cumRule#5: A sissy takes it in the assRule#6: A sissy loves pinkRule#7: A sissy loves her toysRule#8: A sissy dresses like a slutRule#9: A sissy sharesRule#10: Sissies love facialsRule#11: A sissy must have a tight assRule#12: A sissy must have perfect bimbo makeupRule#13: A sissy grows big fake titsRule#14: A sissy is a pro cock suckerRule#15: One is...

2 years ago
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Sissy Julian Chapter I Beginnings

Here we go again. Some boys simply are sissies. This is the story of one of them. It is not a story of discovery, although there is much of that, but rather a tale of a lovely boy's trip to self-realization, albeit a tad 'forced.' If lots of frilly sissy boy and girl outfits, super swishy behavior and a little sex, not to mention dominant women, are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fictional fantasy work. No references...

1 year ago
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Sissy Crissi Chapter 3 Leroys Turn

Chapter 3 - Leroy's Turn But Leroy had been left out for too long. Eager for his turn, I had no sooner finished pleasuring my Mistress when I felt his hands reach up under my skirt and start pawing my panty covered ass. Standing behind me, Leroy bent down and lightly held the back of my thighs in the palms of his large hands. He slowly slid his caress upward, off my stockings, across my garter straps, up to where he cupped my round bottom in his palms. He then placed his fingers...

3 years ago
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Sissy discovers Part 5

Part 5 of the story about Sissy and her sexual awakening ****************Brad did not hesitate when invited to go over to Lisa’s. Sissy was not surprised. What young male would not want to hangout with a girl who flaunted her nude body in front of him only hours before. They decided to take the pontoon boat over as it is ten minutes by boat and almost 40 minutes by car. Evening cruses was a family specialty and Brad was good at handling the boat. As they pulled up to Lisa’s family dock Sissy...

4 years ago
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Sissy gracie Life begins anew

Sissy gracie, Life begins anew Chapter 2 As i stood to dress.. the first guy asked me.."So cunt.. you are wearing sissy clothes underneath and all lockedup. Do you have other clothes .. other sissy clothes?" 'ohh Yes Sir' i replied... "Good .. tomorrow.. bring the key.. and wear more.. i want to see you all sissified...... no pants.. just sissy clothes.. prissy dress.. stocking.. high heels.. make up... make your tits look big...... do it up...... and I will hold your key...

4 years ago
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Sissy thoughts 2 Questions From Sissies

1. I am about to have my first experience as a sissy with a Man! How can I make it more special for us both?A: How wonderful! You are at the very start of your new sissy life. It will of course be special and memorable, but to deepen the reprogramming of your still-forming sissy mind, try dressing as a sissy schoolgurl. Not only will it drive your Man wild with lust, but the symbolism of your costume, and the reality of the loss of your virginity will combine to kickstart stronger, more...

2 years ago
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Sissy Farm Chapter Twelve

Sissy Farm - Chapter Twelve 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....

4 years ago
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Sissy Sally

CAUTION: This is a forced fem story. If this is not your thing, please move on. All rights reserved. Sissy Sally Sam Smith fretted anxiously at the kitchen table while he waited for his mother to return from the district attorney's office. How could he have been so stupid? Breaking into the new neighbor's house had been a disastrous idea from the start. Ms. Johnson was an attractive, impeccably dressed older widow who had moved into the house-...

2 years ago
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Sissy discovers Part 4

the continuing original story of a young girl finding herself****************************Breakfast was filled with the usual mumbles of ‘good morning” and banging of pots, sizzling bacon and gurgle of juice being poured into tumblers. Sissy and Brad avoided looks at each other at first, and then Sissy sat down across from him at the table and patted him on the head saying, “what’s the matter grumpy?” in an exaggerated baby voice. “Nothin’ - hand me that fruit will ya?” He replied and gave...

2 years ago
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Sissy School Part 2

SISSY SCHOOL - PART 2 By Missy Crystal I followed Mistress Mary back to her office. She left me standing in the middle of the room and sat down behind her desk. After ignoring me for a few minutes, she looked up and said, "I told you that you would be severely punished for disobedience." Crap, I thought to myself. I already have six strokes of her leather paddle coming. What did I do wrong? My face dropped. She smiled, "but I can also reward, when I am pleased with your behavior. You...

1 year ago
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Sissy Cruise 3

"We are going on a Caribbean cruise, in two weeks time......." stated my wife Penny. "Oh......Okay," I queried. "With Samantha and Tim," she finished. "Oh really." Samantha is a new friend in my wife's life. They have known each other for a couple of months, but they are already quite close and always scheming together. My relationship is mixed. It seems that the only time she talks to me is to point out my faults which is somewhat annoying. However she is very domineering...

3 years ago
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Sissy New Year

Sissy New Year I remember heading out to a New Years Eve party with a group of my friends from work. I remember stopping by a bar for a few, pre-party shots--well, several pre-part shots. I even recall the super-hot transvestite hooker that winked at me as we left the bar. I don't remember anything else after that. Which explains why I was so confused when I work up a few days later, blindfolded, tied up in a strange bed, with something hard lodged firmly up my ass and a big...

1 year ago
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sissy rules

A sissy must wear panties. He does not own any male underwear.A sissy may wear a bra and pink or brightly colored tights or leggings.A sissy must sleep in lingerie. If he does not have any, he must sleep naked.When alone, a sissy must dress as a girl. Good sissies wear lipstick while alone.A sissy always keeps himself free of facial hair, and is otherwise well groomed. He must always be presentable, ready to please. Good sissies shave their legsEvery morning after he wakes up, a sissy strips...

4 years ago
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Sissy Arm Wrestler

Sissy Arm Wrestler By Margaret Jeanette Margie Ware came home from working out at the health club she belonged to. She was wearing the blue dress she had worn to work. She always felt renewed after a visit to the health club. She tried to visit it at least two times a week. It wasn't easy as she worked overtime at least two nights a week. She always tried to make it on Tuesdays and Thursdays. She looked at her husband of six years sitting in the recliner dozing while the...

3 years ago
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Sissy New Year

Author's note: My stories generally featured a lot of forced femme, bondage and kinky sex--you know, the stuff that I keep hoping will someday happen to me. That is still true for this story, but this time around, the author in me decided to spend a bit more time developing the characters before commencing the full-on sissy sex orgy. I also wanted to write a story where the characters are well intentioned instead of simply being a rogue's gallery of perverted bastards. With that in...

3 years ago
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Sissy Farm Chapter TwentyOne

Sissy Farm - Chapter Twenty One - 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; Doctor Shirley Williams: 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...

3 years ago
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Sissy Tammy

Sissy Tammy It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a child I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games. My...

2 years ago
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Sissy Julian Chapter VI Growing Pains

Sissy Julian - Chapter VI, Growing Pains by: sissystevie Yes, 'tis I, back again. If I can remember how to post this thing on FM. I came across a partially completed additional chapter to this saga, which I abandoned for personal reasons eight years ago, and thought why not? Thus, spurred on by some of your wonderful comments, I completed the chapter and may well complete the saga. There are just too many wonderful kinky - and romantic - moment to come. If you want me to...

3 years ago
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Sissy 101 Intro to Sissy Sluts

Sissy 101: Intro to Sissy Sluts One week before my freshman year at college, I received a letter saying that my class schedule changes had been approved. That struck me as odd because I hadn't requested any changes. Without explanation, I had been un-enrolled from two of my general studies classes. I was now signed up for SISGEN101 and SISHYP161--whatever that meant. I went online to the university's website. These classes weren't even listed in the general course description...

2 years ago
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Sissy Farm Chapter Nineteen

Sissy Farm - Chapter 19 - 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...

1 year ago
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Sissy in the making

Chapter 1 Jim arrived at the North Carolina motel Saturday afternoon as he wanted to make sure everything was in order for Mistress Cleo's arrival on Sunday, as per her instructions. He had gotten the suite to insure there was enough room and comfortable for his new found Mistress. A Mistress he had never met, but already under her control. He began to lay out the items he was instructed to bring, maids outfit, bras, panties, stockings, and every female garment he thought might...

3 years ago
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Sissy Caught at Work

Who ever goes to work thinking "today my life is going to completely change forever". I certainly didn't think that when I got up this morning. I thought I was heading for another typical day at work, full of boring meetings and sipping coffee. Little did I know... My day started like any other, 5 mile run at 6AM, shower, get dressed and headed to work. The only twist is what I'm wearing under my clothes. I love to wear girl's panties. I wear them all the time to work, and today is no...

2 years ago
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Sissy whorehouse veronica

Chapter 1 - The CaptureBefore I became a girl I was a lonely boy with no friends. I couldn't seemto make friends with anyone. I hated myself and I hated my life. One day Idecided to take a walk and try to get away form my troubles. It was earlyin the morning, the sky was a pretty pink, and no one else was out. Butthen, out of the corner of my eye I spotted a black van with heavily tintedwindows coming down the street. It slowed down beside me and as it did Igot a little scared. I was alone on a...

3 years ago
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SISSY DANI

I was not aware that my girlfriend had begun studying hypnosis,nor that she harbored ambitions of petticoating me. But I soondiscovered that the combination of the two was dangerous to mymasculinity. One afternoon I was sitting in my living room,listening to the stereo through a pair of headphones. It was awarm, sultry day, and after a while I drifted off to sleep. (Muchof what follows my girlfriend--now my mistress-- explained to melater.Seeing that I had dozed off, Jennifer saw her chance....

3 years ago
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Sissy discovers Part 3

part 3 of an original story********************After the drive to the lake it is a family tradition to pick up a pizza from the local joint at the village. The pizza is delicious after a day of driving. The whole family, mom dad and the k**s have just about demolished the large pepperoni and roasted red pepper pie. They sit around the counter and woof down the last slices. As they talk about the tomorrow and plans Vicky gets up to clean the counter, and Tom snuggles up behind. The k**s...

2 years ago
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Sissy Tammy

It all started back in the 60's, 1967 to be exact, when I was 13 years old. As a c***d I was a bit small and frail, taking longer to develop than most boys my age, and as a result I ended up playing more with the little girls on my block than the boys. This was also a problem of geography, not having any boy friends living near us, and that was probably just as well because all they did was tease me and beat me up, never letting me play any of their games.My only real play friend was a pretty...

2 years ago
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Sissy Julian Chapter II Introductions

Julian's story continues with his first day at Lake Orenda, and quite an interesting day it proves to be! If lots of frilly sissy outfits, super swishy behavior and a little sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking anyway. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, places or events whether past or present. This chapter is rated R as it contains sissy sex....

1 year ago
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Sissy Crissi Chapter 2 Facing Erika

Chapter 2 - Facing Erika But my bliss would be short lived. I was abruptly wakened from my dreamlike state by a jarring shove into my shoulders that snapped my neck back and sent me reeling forward to the floor. I tried to reach out my arms and break my fall, but one hand was pinned between my pantied crotch and thighs. I reached out with the other and managed to get it in front of me, but it only tended to cause me to roll to the side, throwing my shoulder into the floor and toppling...

4 years ago
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Sissy Factory 3 School

Note: The following journal entries are sanctioned by the overseers of the Sissy Training Academy. STA staff believes that this history might prove useful for the future training of young sissies. With that goal in mind, Sissy 16452 has been authorozed to recount her experiences as part of the graduation and release process. As always, STA welcomes any and all comments regarding this sissy's account. Your thoughts are helpful in deciding future training courses for our young...

3 years ago
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Sissys SheCock Training

Sissy was in the corner on his knee's patiently waiting for Mistress's command. mind racing at the thought of days adventure, a nervous tremor passed through him wondering what it may be. Mistress had said she had a little surprise in store. Mistress standing there in black leather corset, her ample breasts on display fully fashioned stockings, 5" studded 5" heels crop in hand.Smiled and turned to the dresser grabbing, shiri, and sissy's collar, turning back to sissy in the corner, said over...

1 year ago
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Sissy Husband

Sissy Husband By Margaret Jeanette Betty Burns was headed for her mother's place. Her mother lived eighty miles away. She was talking to her on her cell phone, actually arguing some more with her. Just like that her mother hung up on her. She dialed her back and when her mother answered she said she didn't want to talk to her and hung up again. Betty turned her car around and headed back home. So much for a week-end with mother. She knew her mother had a temper and it...

4 years ago
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Sissy Farm Chapter Eight

Sissy Farm - 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 Jamie, ...

1 year ago
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Sissy Teaches Me Part Two

“Are you watching?” Sissy asked me as she lied there, legs spread nice and wide. The inner part of her pussy starting to gape a little, trying to open up larger than it was already.“Yes,” I answered.I was watching with everything I had.Sissy ran her hand down between her smooth legs and I watched her take her finger and trace her tender sexual entrance slowly. As she did, I saw her puffy lips come to life. Her inner ones swelled and slightly parted even more to reveal the hot pinkness hidden...

Incest
1 year ago
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Sissy School Part 5

SISSY SCHOOL - PART 5 By Missy Crystal I woke up thinking that I was in my bed at home and had a bad dream. I was on my back looking up, but the ceiling of my bedroom wasn't pink. Then the weight of my bedmate's arm and leg draped over me, the warmth of her body against mine and her soft breath on my neck as she slept quickly reminded me of what had happened the day before. My mother sent me to a school for sissies and here I was in bed with one. Well, that really wasn't the bad part....

3 years ago
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Sissy Julian Chapter V A Day at the Village

Julian spends a most interesting and eventful first day in Lake Orenda Village. So, if lots of frilly sissy outfits, super swishy behavior and a little kinky sex - not to mention dominant women - are your thing, please read on. If not, thanks for looking. It is also a purely fanciful, fantasy fictional work. No references are intended to portray any actual persons, situations, places or events whether past or present. This chapter is rated X just because of the sheer kink of it....

3 years ago
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sissy Britney serving Mistress Jeri James

About a month ago sissy was honored to meet and serve her Mistress.Mistress has been training me for a couple months to be her Britney sissy slave.Training included watching lots of sissy hypno vids along with BBC hypno vids.Learning to dress as Mistress likes, sucking dildoes to become a better cocksucker.Locked in Chasity, my chastity is a nub because my clitty is so small.Wearing butt plugs and once I got use to a size, I had to go purchase a bigger one to getMy pussy ready for large BBC.I...

2 years ago
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  • 12
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Sissy Fantasy

I waited for what seemed like hours and was probably minutes when I heard Masters voice. "Silly me I forgot to open it, better hurry sissy I don't think Jenny would be too pleased if the neighbors saw you dressed that way," he smirked. The car lights flashed and the boot unlocked. I grabbed the cases and hurried inside. As I was passing Master he handed me a package. "A present from Jenny....put it on when you change... and put my case somewhere safe but don't open it," he...

2 years ago
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Sissy Farm Chapter Nine

Sissy Farm - Chapter Nine 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...

1 year ago
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Sissy Gets A Black Master

Sissy Gets A Black Master I got up wearily from my long and exhausting night being fucked and punished by my new Black Master. As I awoke, I could scarcely believe that all those depraved things had happened to me. One minute I had been merely exchanging emails with a man, who could have been anywhere and the next minute, that very man was at my door, in my home, and then inside my body. Black Master, a man whose name I didn't even know, a man who looked to be about ten years my junior, had...

1 year ago
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Sissy Outed Brandon to Brandy

This is a story about seduction and transformation that’s written about a real-life sissy named Brandon Hippel, Brandon’s a cute little limp-wristed sissy-faggot from Abington Pennsylvania that loves to be humiliated and exposed online. She loves feminization, crossdressing, being exposed online, humiliation, anal play, degradation, being captioned, taking pictures, and talking to new people, so feel free to contact her through these various social media; Her kik is; HumiliationSlut2Her email...

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