Playing Pregnant

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Sissy uses and enema to feel pregnant and girly.
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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 child, 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 kid'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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AnonymousAnonymousalmost 2 years ago

I'm a sissy, who fantasized about getting pregnant

What I told my boyfriend that I wanted him to knock me up, he was totally turned on.

Now when he is fucking me in my gurl pussy he tells me that he's breeding me.

My poor little clit gets so hard that I cum all over myself without touching it

I've invested in a prosthetic baby bump and I wear it when we go out. I get a lot of attention and questions about when I am due

I just smile and rub my tummy and say

Pretty soon

My boyfriend loves the way that I look with a baby bump.

Sometimes I have to suck his cock in a public bathroom before he fucks me as he is telling me that I'm his cunt

I love being called his cunt. It's all that I've ever wanted to be

DeanVentureDeanVentureover 2 years ago

This is absolutely the best sissy pregnancy story I have ever read. A+ ⭐️⭐️⭐️⭐️⭐️

selinastrattonselinastrattonover 6 years ago
Better second tme

Oh my gosh I have justmre read that and love it even more, thankyou x

AnonymousAnonymousover 7 years ago
I so want to be a pregnant sissy!

I have fantasized this same story for myself many times. I have a daddy with a BBC that loves to breed me every chance he gets. I mentioned to him that I would love to be knocked up by him. That night he came extremely hard deep inside me. He said that the idea of it just put him over the edge. I have been practicing taking large enemas to see how long I can hold them. Wasn't sure how long I should hold them, but since you held yours for several hours, I will train harder to do the same. Daddy said I would look sexy with a baby bump and I want to please him. Thank you so much for your story.

AnonymousAnonymousover 7 years ago
me too

my dream to be pregnant with my black daddies baby . wearing my slutty maternity dresses.

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