Pregnant Sissy free porn video

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I'm a sissy. I used to be a femboi, then I was a crossdresser, and now I'm a sissy. The main difference between the crossdresser and sissy phases was the attitude; before I was a guy doing this for fun and to be admired, sexually – to confuse straight and gay boys alike. But now, as a sissy, I was devoted firstly to my master and love, Noah, and secondly to my own lustful femininity. I was, it seemed, always striving to be more feminine and more sexual – which is difficult when the bar started so high. My master loved driving me further into this kind of horny girliness, this girly horniness, but did it all in contrast to my former self. He never gave me fake breasts, for example, and loved to remind me that I was a silly little boy who gave up every future an 18 year old has open, in order to become a fuck toy. Two years on from the start of my service, he still called me 'bitch' or 'sissy boy/fag/slut' or 'cumslut' but never 'girl'. He let me know that I was a feminine fuck toy, and not quite a girl, which tricked me into always trying harder to be more girly – I wanted to impress my master after all!

Aside from my master's eternal wisdom about keeping me in place, there came a point where I thought I couldn't possibly get any more girly than what my day-to-day sissy life was. I was completely clean shaven all over, and had a lithe, flexible body. Without doing anything unalterable or unnatural I had achieved a sexy girl's body – my hair too, grew out naturally and was of an amber blonde, luxuriously thick (for this I had a very good shower routine to thank), and often tied up in a ponytail (for light tugging). I wore girl's clothes, only girl's clothes, no matter where I went and no matter what I wore as an outer layer, my skin was in close contact with perfectly matched sexy lingerie. Master wanted me permanently ready for sex, and I enjoyed permanently being ready for sex; it was, after all, the only surefire way for me to get an orgasm as I had been locked up in chastity. Funny that, the chastity cage made me much, much less chaste than I was before. But it did make me obedient to just the one man, my master, Noah.

I say his name here for detail, but he prefers me to only call him 'master', 'sir', or 'daddy' and I'm more than happy to call him these things – he is, after all, very kind to me and truly loves me, so I love him back. He cooks well, and helps me with day to day stuff, as well as going to work; but underneath that there is a constant underlying primal lust and ferocity – he is a man who knows what he wants. I am his object to use, because I am a sissy slut, but because he loves me I am his sissy slut, his alone. It helped that he was very attractive, tall, toned, with thick black hair and well-trimmed beard. He had a look of the rockstar about him, the rockstar that had become the average man. Not to say he was average of course, he was far above average in many regards! To put it bluntly, his 9 inch cock put my caged dicklette to shame. Regularly. But beyond just that, he had tastes beyond average, and a great imagination too. In our first year alone he fucked me a different way for every day. He was pretty rich, only 23 but from a rich family, and this afforded him free time and a great many toys; bondage is regularly worked into our playtime and he loved to bring out these toys when I was in the most helpless positions. It was while I was tied up with my feet on the back of my head, while he was teasing my smooth balls with his magic wand, that he decided upon the last shove: I was wrapped up like a present, and he was ready to own me completely.

"Hey sissy boy" he whispered into my ear, leaning into me "let me hear you purr". I let out a low, rolling groan of pleasure and he laughed out a "good slut" as he turned off the wand. I gasped with a little disappointment before he grabbed me up and settled me on his lap, his cock nestled between my feminine ass cheeks. "Does this little sissy fag wanna be a real sissy girl?" He asked me. I nodded eagerly, tongue nearly hanging out. "Tell me." He said.

"Daddy, my lovely daddy, this sissy boy wants to be your little girl, please make it happen, whatever it takes. I deserve to be yours" I finished, a mite petulantly, causing him to grin.

"Good slut" he whispered before kissing me hard and lowering me onto his cock. He'd shoved it into my mouth earlier, so it was still pretty wet from that, but it wasn't the most well lubed I've had from him and it was only his tongue dominating my mouth that stopped me gasping in pain. "We're going to do this properly, fuck you like the eager little slut you obviously are, but by the end of it you'll also be my little girl too"

"Yes master, yes daddy" I replied, clenching down on his cock, the only action I could really do tied up as I was.

"You see, cumslut" he began to lift and lower me, in time with the thrusts of his hips "today, daddy is going to breed you."

"mmm, yes master, I love the feeling of your cum up my tight little ass" I moaned, excited because in the past few weeks he had mysteriously started using condoms (though, admittedly, the cum from those still ended up in my cumdump belly anyway) and I honestly did love the feeling.

"I know you do you silly little cumslut, you practically live for it now. But this time it's different. I can tell from you moans you're in heat – and I haven't cum at all these past few days – I've been saving it for this moment to breed you properly. We're going to have some fun, slut."

With that he picked me up and started rapidly pumping his dick into my ass. He carried me over to the table and span me round, fucking me hard onto the wood, my locked up dick rubbing into the groove it had made on the table. He slowly undid the bonds around my legs before picking me up again. He made me face him before thrusting me against the wall. My legs were up by his sides as he ploughed into me, stretching me hard. I could feel the fury of those days he had gone without cumming welling up inside me, I could feel the throbbing deep in my ass. I think then was when I started to feel my caged dicklette leaking all over me as my mind went into paroxysms of joy.

"I head this was a good position" he grunted, drawing my focus back to him.

"For what" I moaned.

"For knocking a bitch up" he replied, before kissing me deeply again. His tongue folded mine back in half, his cock slammed again against my prostate, he hugged my body tight as I was shoved against the wall and jets and jets of cum were let loose into me. I was kissing him back furiously, overjoyed. There was so much cum, I thought it would flow out, but he held his position; his cock was completely buried, the base in contact with my asshole – his cum was shooting straight into me. Eventually he stopped, and put me down. He untied my hands and slapped my ass. A tiny dribble of cum came out.

"Right" he said, staring at me intensely "you may just be a proper girl now, bitch."

He guided me to the bathroom, where we nearly always did a clean up after sex. He helped me into the bath with a kiss on the cheek, before I assumed my position on all fours (naturally) and he attached a pipe to the faucet. It was an enema pipe, and was used to keep me constantly clean inside, and also to wash out any cum if my darling Noah doesn't want it to stay there. The pipe was thrust easily into my hole, only just starting to close up. I gripped down on the pipe as Noah put the water on. I felt it enter me, a slow warm stream that just swishes around my inside. The pipe was pulled out, cum came out. We did this a couple times – it doesn't take long to clean me but to be fair, there was a lot of cum this time. After a couple times I knew I was clean, but tom my surprise, Noah put the pipe in one last time. The water was off and I was preparing for another sweep, trusting my master on this, when he came round and gave me a kiss on the nose.

"Deep breaths now" he smiled "pregnancy can be a tricky process". I nodded, to tell him I will still, and would always, do what he thinks god for us even if I had no fucking clue what it was. Unless it got me killed; but he cared about me too much to let me get killed. The tap turned on and water began to flow into my ass. The water remained constant and still continued to flow on in; it was warm, and powerful, but you could feel the liquid quality. Still, as it started to press on my prostate, and to force dick to try and rise, I felt the full force – it was like getting fucked by Poseidon, I felt gloriously powerless. In the light of that sensation of helplessness, I simply took a deep breath and relaxed. I had been pushed to this point before, and now I was breaking beyond my barriers.

The water continued to fill me up, at first like a colossal cock, and then like something else. I felt my body swell and stretch. I looked at the mirror we hang opposite the tub. I could see me, looking slutty on all fours, but the tub itself restricted the view of what was happening. I got bigger, and fuller, and all the while my daddy was telling me how I'm a good sissy, a good slut, a good little fag. I continued to swell and almost as unexpectedly as it began, it stopped. I was full of water, and the hose was still in my ass. Noah told me to clench, which I did, before he began to ease out the pipe. It came out with on last tug and with it a little water: I hurriedly clenched harder, and Noah stuck his middle finger in me, so he was clenching my ass.

"Careful now" he laughed "don't want to get rid of this too soon." He helped me up, weird with this heavy sensation in my stomach, guiding me with both his hand holding mine, and his hand pushing against my butt. My dick was aching again, already, for a release of cum. I got a good glance in the mirror, it was surreal: I had this swollen belly, like someone decently far into their pregnancy (maybe not near the end, I fear that look would be impossible) but I definitely looked like I had my daddy's baby in me. I never was too fussed about actually having a c***d, but the process of pregnancy realised in my body gave me a burst of feminine joy. I clasped my hands to my mouth and laughed, and my master kissed me on the cheek. "look, you really are my sissy girl now, you have to be since I've gone and gotten you pregnant" he said drily. The extra weight and temporary discomfort was worth it to hear 'sissy girl'.

"Thank you daddy, I don't know what to say!"

"What about yes?" I stared at him with wide eyes and he just grinned. He steered me into his room of toys, and brought me to a desk which had on it a small box. He opened this and in it was a cute little petite butt plug, with a shining sapphire in its base. "Mary, will you be my little girl forever?" I gasped at the pretty toy before turning to him and hitting him lightly on the shoulder.

"Silly daddy!" I exclaimed "you know I was already yours forever."

"Yeah, I know, but I wanted to find a special way to make our relationship official. Heck, I'd even like to take you out in a wedding dress – you can even wear virgin white, we're already such good liars."

"Then absolutely yes," I smiled, and kissed him on the cheek.

"Back to business then!"

He took the butt plug out and got me to suck on it to lube it up; with one last wiggle of his finger he removed his hand and replaced it with the toy. It fit perfectly, and managed to perfectly secure the water. I dressed up in some of my older lingerie (in case my newfound figure broke it!) and found it fit a little tightly, but that I still managed to look reasonably sexy. I began to walk around the room, slowly at first, before gaining confidence and I started to dance sexually for my daddy. I rubbed the baby bump and moan lewd things, saying how whether male or female, the baby would take after its mother; I told him we should feed me loads of cum for the nutrients; I warned him with a wet whisper in his ear that pregnant woman get really horny, and really kinky.

"That's what I was planning on" he said, adding with his old commanding tone "now get on your knees, slut." I started to kiss down his body, licking his nipples, worshipping him fully, before I came to my ultimate idol. His cock was hard. Very hard. Even after all that we'd just done, he must have still had plenty of cum backed up from his very short abstinence. I wet my lips and took no time in sliding the 9 inch member into my mouth, I went all the way to the base, hungry for all he could give me. I stuck my tongue out over my bottom lip, and drew back, licking from behind the balls all the way to the head. He let out a groan which sounded a lot like "ugh, fucking magical, girl". Encouraged, I started to bob just on the ridge of his head, and then slowly increased my depth, working the shaft, all the while licking both top and bottom, and moaning like a whore. The vibrations got to him, he loved that, and drove him to encourage me further.

"Good girl" he groaned "you sissy little girls do it best don't you, you little slut. Stupid pregnant bitch, still out for more cum, are you a hungry little girl?"

Every 'girl' he said made me moan, and caused me to increase my speed. He was right, I was actually hungry for more of his cum now and was rushing towards his orgasm. I slid my wet, warm mouth once more down his glorious shaft and he took my ponytail and pulled me onto him, keeping me in place as his cum shot straight down my throat in still pretty powerful streams.

He released me for air and I smiled up at him.

"Good girl" he said, and took me to bed, helping me all the way and telling me how much he loved me, his little girl, his own babe.

The next day, he woke me up with another surprise. I had kept the water in all night (that is to say, the two hours of sleep after the late night fucking) and it seemed he wanted to reward me with a key. He held up this tiny key in front of me and seemed to be overwhelmed with joy.

"Remember this?" he said. Truth be told, I didn't, but when he bent over to my crotch I realised what it was.

"Wait wait!" I cried, halting him. He looked up at me confused. "Isn't that my chastity key? Am I not your little girl anymore?"

"Well of course you are" he replied "but you don't have to be constantly proving that to me anymore, hence, your freedom from the cage. It won't get hard that often anyway."

"Even so... I'd quite like to keep it in its place." Having said this somewhat timidly, I was surprised to see his face beaming at me.

"You're a clever one, little girl, I knew I had more than just your sexy body to love you for. Okay, you're right, but first there's something I want to do."

He unlocked me and brought out my tiny little dick. We both actually had to stifle a laugh, it seemed so ridiculous; but then Noah got to work. He rubbed my head between his forefinger and thumb, and began to massage it into life: to my complete shock I became hard almost instantly! I didn't know what to feel about that. It wasn't long, maybe 3-4 inches? But it was definitely hard and definitely a cock. While I was deciding my opinions on this thing appearing on my sexy girly body (the penis felt stranger on me than the baby bump), I was cut short in my thought track by daddy's tongue on my cock. He was taking my tiny dick in his mouth, sucking on it with hardly a sound but with deft movement of his tongue. I could do nothing to affect him, not with this tiny dick, but with his tongue he was controlling me.

I began to writher and moan, shouting aloud daddy, master, Noah, daddy! He gave me a slap on the ass for saying Noah but continued anyway. I barely even had time to utter 'sorry sir' before he had me on the edge. I was going wild with desire and was so ready to cum when he pulled his mouth away. I was crestfallen. He stared at me, and I stared at him, with puppy dog eyes. He began to laugh, and I sighed, about to resign myself to his joke; suddenly he gave on final lick and I was shooting everywhere. The edge was smashed down and I was shooting cum into my own eye and mouth, my dick overcompensating for years of little sissy dribbles. It was glorious but it was soon over, and my dick was limp.

"Was that fun?" he asked. I nodded. "Still wanna stay locked up?" he continued. I paused, but then nodded. "Clever girl" he said, reinstating the cage and chucking the key somewhere behind the bed. We went back downstairs, and out into the garden. He told me that he wanted to film me as the pregnancy ends, and that nature was a great start for a k**'s life: he had actually planted flower seeds recently so it could very well be that our little game leads to some strong, healthy lives anyway. He fetched the camera, and set it up in the garden. He filmed me as I walked through the garden, practically naked apart from my lingerie, stockings and all. I'd gone for something more pretty and pink, rosy, in celebration of the event. I gave a little skip, and showed off my ass (with shining plug) and a little of my caged dick, before I sat down on a little stool he'd set out; I spread my legs wide and bit my lip coyly. My hand slowly rubbed down the front of my body, rubbing over my panties and cage, before resting on the jewelled plug. I gave the camera one last shine of the jewel between my fingers, before grabbing the plug and easing it out. A little water fell, but most of it stayed inside – I'd grown accustomed.

My master laughed out 'push!' from behind the camera, and with a wink and a smile I followed his orders. A beautiful clear stream of water, as if from the tap, came flowing out my ass as I giggled and bit my finger. It splashed across the ground and still more flowed out. On my part, I loved acting as the silly girl, but moreover I loved the sensation of relief. I felt light all over, light headed included, and it seemed the water was pushing against my prostate once again as it rushed out; it was an insanely good feeling. I giggled again, laughing that sissy girls even get to have better births than normal girls! Eventually it was all gone, and Noah shut off the camera, the video ready for some purpose or another: maybe we'd sell it to a porn site, or put it on the internet for free; or perhaps we would watch it back later and get so aroused we'd end up doing the whole thing again

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A Happy Sissy Kathleen didn't iron. Janelle wouldn't work past noon. Hannah wanted too much money. Damn, good help was hard to find. Monica, my wife, sat on the bed with the newspaper ads spread around her. She was looking for a maid. The way she tells it, Sharon had been a domestic with her family for a thousand years. As Monica grew up, Sharon was always there to advise her, to steer her toward decency, to make sure she knew that hard work was the key to good results....

2 years ago
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The Blushing Sissy

The Blushing Sissy by StateRowdy [email protected] ? She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties down...

2 years ago
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Degraded Sissy

fondamaid asked: Hi. Sorry it's been a while. I haven't dressed and I felt a little odd sending you a note while in men's clothing. Today I'm dresses, corseted, and locked up. I'm just not sure how long I'll keep myself locked up. I did finally get baby oil to use though and the cage is more comfortable because of it. I thought lube would work fine, but I was wrong. Now I'm all sissied up and wondering what I should do. Part of me thinks I should practice pleasing real men.I hope that, when you...

2 years ago
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How to Build a Better Sissy

How to Build a Better Sissy Or My Evolution by: Missy Satinpanties I was a small, skinny child, with a rather normal family. My father worked for the electric company as an auditor, and my mother ran a yoga studio in the converted garage of our home. When I was young, this was where I played, watching women contort themselves into the various yoga poses. I was about 6 when I asked my mother...

3 years ago
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Checkerboard Sissy

Checkerboard Sissy By Cassandra Morgan A guy never wants to meet his girlfriend's parents for the first time. There are always years to negotiate, and beliefs, and backgrounds. As nice as the parents may be, there are always judgments to make, and old boyfriends and girlfriends to reference, and finances to be probed. It is natural to be suspicious of someone who loves your child. For Keisha and I, this was more challenging than for most couples. As an interracial couple, Keisha...

3 years ago
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Trucker Daddy Gets A Sissy

It could easily be the lowest point in Denny life, sitting in an old Ford Escort that wouldn't start, the temperature outside well below freezing and him not having the cash for a hotel or to have the car fixed. He had no idea what to do next. Completely out of ideas, he had been sitting in for hours watching the normal people with money coming in and out of the Flying J Truckstop. He almost jumped out of his skin when someone knocked on the window. Denny cautiously rolled the...

2 years ago
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Saturday Night Sissy

SATURDAY NIGHT SISSY by Throne I spend all week, every week, dreading Saturday. My wife Alana met Dutch several months ago. I knew my bride had a past as a party girl, and that she still flirted with men. Male eyes always went to her, a tall girl with a stunning figure -- big bust, tapering waist, flaring hips, full thighs and, most of all, a plus-size bottom that sticks way out and moves like it's on springs. Dutch was the kind of guy she used to date -- big, rough, uncouth. The...

3 years ago
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The Blushing Sissy

Story writing contest 10 [email protected] She'd been teasing me all week, much, much more than usual. And, now I could hear her talking to me from her bathroom tub, which by the way, used to be our bathroom. Me, I was busy ironing her long and elegant pinstriped wool gabardine black skirt with the flounced hem and her very sheer ruffled black silk halter. Ironing is perhaps one of the hardest chores I have to do. Everything had to be just so, or it was over her knee, panties...

3 years ago
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Home Alone Sissy

What is it they say, "It all began like any normal day." Well since I was wearing a sissy maids uniform it was not going to be a normal day! I had on black patent leather Mary Jane shoes, with four inch heels. I love higher because it forces me to walk more daintily but I had a full list of chores and would be on my feet all day, so practical is better. My legs are encased in shear black stockings, of course they have to be stockings, tights just do not do it for me. They have a...

3 years ago
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Be a Sissy

forced to be a Sissy IThe young man stood facing a very large woman sitting in an upholsteredarmchair. There was no other way to describe her. She was fat, perhaps,pushing 300 pounds he thought. The way she was staring at his punyframe suggested that maybe he was going to be her next meal. She wasn'tsaying anything as she visually appraised him for the first time...Jacob had been brought to this woman by his step-grandmother earlierthat morning. He had been given over to his step-grandmother by...

3 years ago
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Sissy On Sissy

SISSY ON SISSY by Throne Bob stood there feeling beyond foolish. His body had been denuded of hair and his skin, after weeks of using an imported emollient, was satiny. All he had on was a pair of bikini-cut panties and a training bra. He was wearing the latter because his wife, Tessa, had taken him to a specialist two weeks before and gotten him a lovely set of breasts. They were small implants and his nipples rode high on their feminine curvature. It didn't provide any modesty...

1 year ago
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Mrs Grant and her new Sissy

New Little Sissy"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was...

3 years ago
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New Little Sissy

"I'm done planting the flowers Mrs. Grant," I said."Justin honey, I swear I have no idea why you keep coming over to dochores around here.""I am rich you know just like your Mother, I do have a gardener.""There's no need for you to do these things.""Not that I mind paying you, but you certainly can't need the moneyeither.""I just like coming over here Mrs. Grant."She appraised him slowly now, was this a little slip, or was she justimagining things? Was he actually saying he was attracted to...

2 years ago
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Its Hard For This Sissy

IT'S HARD FOR THIS SISSY by Throne Pete had just gotten home from work and he immediately noticed a look of mischief in his wife Andi's pale blue eyes. He seen that all too often in the past. She must have spotted the concern on his face because she wanted to know, "Is something the matter, Petey?" She was calling him by the diminutive of his name. The switch from Pete to Petey was another bad sign. "It's just..." he extemporized, "that you seem... distracted." "Well,...

3 years ago
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stepson becomes moms sissy

Mark Peters let out a low moan that couldn’t be heard above the organ as it played "Here Comes the Bride." Although every other head in the church turned to glimpse the tall, dark-haired beauty imperiously making her way down the aisle, Mark kept his eyes fixed on his feet. Had anyone been paying attention, they would have seen a small tear escape Mark’s eye.It seemed like only yesterday that Mark’s mother and father had split up. Mark’s dad, Mark Senior, was a partner in one of the city’s...

1 year ago
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My Sisters Sissy

My Sister's Sissy By: Missy Satinpanties Note: This isn't one of my usual stories of sexual degradation, but what I think of as "my autobiography that should-have-been." The make- up of my family is the same as it was, my sister's names are the same, but that's about it. This is how I wish things would have gone when my little secret got "out of the bag." I guess I've always been a sissy. I remember playing dress-up with my sister when I was very young, and can vividly remember...

3 years ago
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A Nasty Daddy gets a Naughty Sissy

I came out of the bedroom dressed in my too-short pantyshowing Pink Shorty dress, pretty anklets, black MJ's, pink panties, red lipsticked lips and with my cute cuff and collar set on, awaiting Daddy's padlock, which would begin the playtime for real. This Daddy I had run across on a website was one who loved forcing sissies to literally mess their panties while they were in bondage so he could then go on to the diapering and teasing them for being such bad baby girlie sissies. Me,...

3 years ago
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Sissy Stepson 10 Stepmothers Sissy

Part 10 - Stepmother's Sissy Mrs. Monet put another knee high on the exhausted sissy and got an open toed spike heel with a very small opening in the toe of the shoe. Mrs. Monet forced the shoe on the sissy's limp dick, which started to harden within the shoe. "Come on sissy, just three more milkings, I know your balls ache and your sissy stick is red and sore, but you promised to hump my shoes!" his stepmother cooed. Finally, Caroline's sissy stick got hard enough for the just the tip...

3 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

1 year ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy. Sissies are...

2 years ago
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What does it mean to be a sissy

Sissies are a distinct breed of transvestites. A sissy is a transvestite who’s primary sexual interest lies not just in wearing feminine clothing, but in becoming an exaggerated version of femininity. Femininity as seen through the lens of traditional hetero male sexual desire. Sissies are not seeking to become women in a normal sense, but are instead seeking to become the object of their desires. Their ultimate fantasy woman if they were normal, rather than being a sissy.Sissies are...

2 years ago
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Ken Sissy

Ken sat there, staring blankly at the movie screen, showing a big black cockplowing into a white beauty. His wife was far from a beauty, as she was now inher early fifties and had put on a few too many pounds for his taste.... butevidently it didn't seem to have bothered the two black men.Ken looked over his shoulder at the entrance to the adult theater, hoping thathis wife would be walking back in, but he knew better. It had all happened sofast, that he tried to remember how he ended up...

3 years ago
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Mistress Sabines Sissy

My phone vibrated softly signaling a text. I almost didn't look at it. I was at a meeting of the board of the corporation I work for, trying to steel my nerves for a presentation I was scheduled to make. This was my first time and instead of running through my presentation in my head I was focused on what I was wearing under my suit.I glanced at the phone."Someone in the room knows exactly what you're wearing..."It was from Mistress Sabine, a woman I'd only met a few weeks ago. She was also the...

1 year ago
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Miss Lindas sissy

My finger was shaking bad as I went to push the doorbell. Miss Linda had told me how my slave training was going to change. She told me she was going to turn me into her sissy slave. Oh My God! What was I doing here? Why did I even come back here? I was afraid of what my heart said in response. The truth was, I really wanted to be a sissy. Even the thought of the intense humiliations that were to follow excited me. I rang the doorbell and felt my doom consume me. Ms. Linda answered the door...

2 years ago
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The Misadventures of the Worlds Worst Sissy

The Misadventures of the World's Worst Sissy By Cassandra Morgan This stuff isn't easy, okay? The world that looks down upon us think that it is. They think that any wimp can be a sissy, that even the frailest of us can scrape and bow and curtsy. They think that anyone can cook or clean are do the so-called mindless tasks that the rest of us are assigned. They think this is a soft life for soft people. They think we are so concerned with being pretty and smelling pretty that...

2 years ago
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First time Sissy

I was born a "boy" but it was mother nature mistake as I am very petite, 5'2" 110LBS. with a sexy round ass and dick sucking lips. For this site purpose I will start at 18 my journey as a sissy cum loving size queen SLUT. In my senior year with a couple of months to go before graduation I turned "legal age" but was no virgin by any stretch of the imagination but cannot talk about it because of "rules". I had become a "male cheerleader" but was finer than some of the bitches there and had the...

Transsexual
2 years ago
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Im Not A Sissy

I'M NOT A SISSY by Throne My name is Joe and not Jodie. I'm an adult and not a kid. And I'm a man and not a simpering sissy. I keep telling myself that. But my wife Arianna thinks differently. I mean, ever since we got married two years ago she had been running my life more and more. Talking down to me. Turning me into her sex slave in the bedroom, demanding oral attentions and giving almost nothing in return. She mocked my small penis and made me masturbate while she watched....

1 year ago
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Richard the Sissy

Richard the Sissy by Joney Cunningham Hi, my name is Richard, or should I say Regina now. I am a sissy. It all started when I was 15 and my parents had taken my 13-year-old sister out of town for the weekend. I had a part-time job, so I couldn't go. My parents told me that the paid Gina, the high school senior across the street to decorate my mom's sewing room. Gina was into interior decorating and had gained a reputation of doing great work. They told me she would have a...

2 years ago
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The Lingerie Salesman Sissy

I had a career change a few years ago. Admittedly a door to door salesman did not sound good but the money was OK as long as I made plenty of commission but the fringe benefits were amazing. For me it was not household cleaners or insurance but sexy lingerie. Not only did the ladies on my round like to try on the lingerie but as soon as they felt super sexy I would get my “extra” commission. Yes I had all shapes, sizes and ages, even a mother and her daughter were regular customers and I had...

4 years ago
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son turned into moms sissy

My name is Barbie. Everyone calls me Barbie because I am small and I have long blond hair. I am the smallest in my class. My real name is Ashley. Before you ask, I do not like Barbie's. I never played with them. I suppose when you have hair down to your shoulders, then people think you look like a girl and call you Barbie. I am eleven years old.I got this diary today. So I might as well write in it. It is a purple one with a bear and heart on the cover. It has a lock on it. I might as well use...

3 years ago
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Cum Craved Sissy

Taking a quick look at the clock, I noticed that the delivery had run late, and I was immediately stressed at the fact that Mistress would be home shortly. I knew I didn't have time to shower, and there was certainly no time for much cleanup either. I just pealed the skin-tight jeans down, crumpled them up and buried them at the bottom of the hamper.I carefully pulled the bright yellow panties down my legs, trying not to make any more mess. I washed the creamy jism away in the sink, squeezed...

2 years ago
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Born a Sissy

Born a Sissy This is the story told by me "grandmother" and my grandson Timmy. Most of it is true and only some parts have been modified. It all started back in 1979 when Timmy was only 9 years old. He was a beautiful child that I loved dearly. Timmy's mother, my daughter, had him at the young age of 17. Being so young she was not quite ready to be a full time mother. She was just like any other teenage girl who had social obligations to meet. She was a good mother but I understood...

2 years ago
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sissy

Thanks Megan for the courage to comment. I like constructive criticism, and in addition, would love to be your toy! This chapter is dedicated to you!After returning to my house, I realized that our shopping trip did not accomplish what we set out to do, which was to get more panties for me to wear. So as not to disappoint Elaine, I dressed, the panties in place of course, and returned to the store. Not sure what to expect I walked slowly through the door.The salesladies smiled and said, "Look...

2 years ago
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From manager to sub sissy

Cindy was a co-worker; well actually I was Her manager. Even though I was Her manger, W/we were very close friends. As a matter of fact I still consider Her my best friend. Everyone in the office was sure that we were having an affair, but we were just friends. I must admit that I would have loved to have an ongoing affair with Her. I know that I am not near man enough for Her and I have always know that from the first time I saw Her. Eventually after being friends for many years, I...

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