Daddy's Sissy Bitch

Hiya!! Here are the conversations with a guy I met online. I responded to an ad where a Daddy wanted a sissy slut to dominate and order around. This was the first time I ever did anything like this. This was the first time I dressed up as a sissy and took pictures and sent to another person to look at. All of the pictures he ordered me to take I posted in my gallery for you all to see. Enjoy!

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Hello,

I am a 19 year old male that is inexperienced in cross-dressing but would like to give it a try. If you send me instructions I will obey and send photo proof. Then we can try Skype if you want.

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Hey, sounds like fun and exactly the type of thing I'm looking for. I'm 28 btw, I realize I didn't have that in the ad. You probably noticed I didn't specify any type of look in the ad and that's because I don't care, I just want someone with a smooth body and obedient in bed. Sexually I'm turned on by a sub/dom kind of dynamic like I said, with me dominating you and being a little verbal, but if anything I want is too far out of your comfort zone or if you just want to talk like friends at any point we can do that too. Otherwise here are some instructions to get you started:

1) You can call me "Daddy."
2) I want you to take some sexy pictures with a sign that reads "I'm Daddy's bitch." I want you to hold it over your ass while you bend over, over your stomach while you pinch you nipples and over your chest while you lick your sultry lips thicking of my hard cock.
3) I want you to get blue lipstick, red is too classy, I want something exotic for my little cock slut.
4) I want you to get some cheap underwear. Could be borrowed from someone in the house or just something cheap from a store like Gabriel bros. or Roses, but you need some. Daddy wants you in a thong and bra, but since your just starting anything you find will do.
5)Practice sucking and licking your finger and rubbing the outside of your asshole. Also I want you to practice getting on all fours and arching your back like they do in the arched back challenge (look it up if you need to) and moaning in a feminine voice saying things iike "I want your yummy cock daddy!" and "fuck me daddy!" You'll need it for skype down the line :)

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Daddy,

Thank you for the instructions. As for the blue lipstick, I can't get it right now, but I will get it as soon as I can. For female clothing I have my mother's and sister's clothing for the rest of the summer until I head back to college. I hope you like the pictures, and I will eagerly be waiting for more instructions.

Daddy's Bitch

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Very good start slut. When your sister or mom isn't around i want you to get your hands on the sluttiest thong and bra you can find. My little cock whore is gonna wear panties all day today because that's what sissies like, the bra you can save for your photo shoot. Todays photos need to focus on my cumslut's ass too. Get lipstick, any shade until you can get blue for daddy, and at least 2 different panties (one better be a thong if my little slut wants to please her daddy) along with the the bra and take the following:
1) pics of you on all fours, ass in air, waiting for my hard cock in each pair of panties and nude, so at least 3
2) pics of you in your bra in slutty poses, at least 3
3) a pic of you in your regular clothes with your pants down a bit to prove you're wearing panties
4) a pic of you in the underwear holding a sign that says "I love being daddy's cockwhore"
Now have you been practicing arching your back in doggystyle and moaning like a bitch? I hope so, you need to be ready to make daddy shoot a big load when he decides its time for you to please him on skype.

-Daddy

These pictures are under the gallery "My first sissy pictures 1"

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Daddy,

Submitting to you turns me on so much. I was not able to get a thong because my sister and mom don't own any, but I was able to find red lipstick. I was naughty, I did not want to wait until I was home alone so I sneaked into my sister's room while she was sleeping and took her panties and bra. I also shaved my chest, stomach, and ass for you.

Daddy's Bitch

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Mmm I like to hear about what a dirty little slut you are, it makes my thick cock throb to hear about you getting into your sister's room for those panties. My sissy whore did a very a good job with the last assignment so now we're going to elevate things a little bit. I understand that you may not be able to get access to the shades of lipstick that turn me on the most, but seeing you whored out in red will do for now, pose just like the pics I sent in the last email and here are what you'll do before the day is done:

1) Recreate the shots you took yesterday now that you're nice and smooth, but this time you are to pull your panties up between the cheeks of your little bubble ass so it looks like a thong.

2) I want to see pics of you spread eagle and bent over with a your finger massaging your asshole.

3) Now here's a chance for my little slut to earn her special gift without the blue and yellow lipstick, you want that don't you whore? Go outside in your boy clothes but with your panties underneath, it can be your back yard, a park, a street I don't care - but take some pics revealing your sissy clothes beneath. The more public the place and the more revealing the shots, the more likely you'll get your reward. Obviously more pics means more chance too.

4) Today's sign will read "Please give me your cock Daddy." Bonus points if you show it in a public shot.

5) The last thing is a writing assignment, I want you to write me a little paragraph about how you fantasize me fucking you. Be specific, place, positions, gentle or rough etc. If I like it you're more likely my little cumslut will earn her reward.

Daddy's waiting.

These pictures are under the gallery "My first sissy pictures 2"

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Daddy,

I shaved from my knees up because if i shaved my legs my parents would have asked questions. I am sorry I could not follow your directions completely you can punish me if you must. Feeling my thighs and stomach now that they are shaved feels so nice because of how smooth they are.

My sister almost caught me as I was taking her bra out of her drawer. She woke up and I had to quickly put her bra in my pants.

My biggest fantasy is me being taking advantage of by a well hung man. I fantasize about you treating me like the whore I am. You will be sitting on the couch and I will come up to you in a bra and panties and sit on your lap. You will manhandle me and throw me on to my hands and knees and take your dick out of your pants and shove it into my ass. Then you would fuck me in the ass doggystyle as hard as you can while I moan like a little bitch. I will let you fuck me for as long as you want in any position you want because I want to feel used and abused. Then I will get on my knees and beg you to let me suck your huge cock. I'll lay on the couch with my head hanging over the side, and have you throat fuck me until you shoot your load down my throat.

Daddy's Bitch

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You're a good little fuck slut. I've decided I don't want you to get the blue lipstick anymore but you will get the yellow if you want to REALLY please your daddy. For now though the red will do and you will wear it anytime you send me pics or when we cam, I want your lips feminized at all times and ready to suck my hard cock. I'm glad you got away with getting slutty things to wear for your daddy and your paragraph was good. I'm not pleased that you cannot be completely smooth for me so you'll have to be punished. Your punishment is the subtraction of one cock pic, originally you were going to get to see Daddy's cock from below, so you could see exactly how it will be to kneel infront of me before you suck my balls and slobber on my thick shaft, but now you'll just have to wait until you do something worthy of that gift.

Part 2 of your gift is getting to read exactly what I'll do to you when we meet. We'll get a hotel room for the afternoon, you'll tell your parents your off to a video game tournament or some other lengthy event, so you'll be back late or even the next day if possible and I'll say the same to my spouse. As far as the world is concerned we're just 2 straight friends off on outing, with only us knowing that when we enter the room it will be as sissy slut and master. You'll shower immediately when we arrive and pay very close attention to your ass hold, cleaning it as deeply as possible before you change into your slutty fem attire, liptick of course included. After I shower I'll come out and take all the pictures of you I want and you'll get into every slutty pose Daddy commands. Then you'll put on a sexy song and give me a lapdance on my naked lap before you lie down across that lap and take every squeeze, slap and grope I give you - and you'll say "thank you daddy" like a good slut each time. Then when I'm ready you'll get on all 4's on the bed, panties around your whore ankles before I eat your pussy and fuck you like I want to break you. I'll start off slow so you can get used to having a thick black cock in your tight little asspussy but soon I'll quicken my pace and shaft your sweet little cunt until your begging to suck me off just so you can get a break from the electrifying pounding. I'll oscillate between your whore mouth and cunt, so you better be clean as fuck back there, douche if you have to bitch, because when Daddy wants to go ass to mouth you the only response will be "yes Daddy, thank you Daddy." Until I'm ready to cum, when I shower your face with jizz and use my hard cock to spoon it all into your mouth. Then I'll hop in the shower again and you'll go lie down in the bed, dirty and fucked like the slut you are, waiting until I'm ready for you again, because from now until we leave that room your only task in life is to make me cum as many times as you can doing exactly what I say.

Now for today's tasks:

1) Find something to insert inside yourself, it can be as thin as a pen or thick as a carrot or a cucumber, whatever your little pussy can take. I doubt you have access to a dildo so you'll have to do one make shift. Vasaline it and penetrate yourself with it while you take pictures. I want to see you in doggy style from several angles with it inside you.

2)Today I also want to see you in girls clothing. Get a tank top from your sister and either a short skirt, a pair of leggings or even shorts if you can fit them, anything that will be tight and slutty on you and show off your sexy little tummy. If you can't manage any of those a tight dress will also be acceptable. Knee high socks are especially sexy to your Daddy. Take several pictures in the clothes and several pictures in states of undress with the clothes in poses that will make my dick hard.

3)Recreate both of the pictures of women I've sent you, each with panties on and off. It's time for daddy to see his little slut's face and you'll get the same as a reward.

4)Come up with your own message today and it better be slutty and mention Daddy in it.

5) Continue to practice arching your back and moaning slutty things to daddy. I suspect you'll have to whisper those things on cams so as not to wake anyone up in your house late at night- that's fine.

6) Add me on skype. _____________ is my name there. You will not know which night you're going to put on a show for Daddy, but it's coming and my little slut needs to be fully ready.

Be a good girl and do exactly as Daddy says slut.

-Daddy

These pictures are under the gallery "My first sissy pictures 3"

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Daddy,

Thank you for exposing what a little sissy whore I am. At first I thought putting on girl cloths was fun every now and again, but you have taught me how much I crave to be a sissy. Waking up every morning and having new instructions from my Daddy to follow turns me on so much. Daddy, I can't keep my mind off of you. I spend the entire day pondering what my Daddy has planned for me next and how to please him. The anticipation of reading your instructions kills me. I wonder whether the instructions will be something I would not hesitate to do, or something I don't want to do but will do anyway to please my Daddy. I wonder about what pictures you want me to take, how you are going to humiliate me, and how you will punish me if I do not follow your instructions. Deep down inside I know that there is very little I will not do to please Daddy.

Daddy's Bitch

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Very good slut, but I've decided you won't get the gift of seeing my face until we cam - a punishment for not having any yellow lipstick for your whore's mouth. Daddy is pleased to hear how much his little whore likes to be broken in, and I liked your choice of the brush for your cunt. Now for today:

1) My little cockslut needs to do something with her hair. Get a head band, hair clip - I don't care, but it needs to be big enough for me to see it in pictures slut, and you'll wear it or something like it anytime you take pictures now.

2) You'll use the brush again and this time you'll touch your boy clitty while you do it until you cum. And then you'll smear that cum on your face and use the brush that was in your ass to spoon it into you mouth, and suck it off the end like you would my cock.

3) Your slutty bare stomach and bubble ass and arched back are your best features, cunt. At least one will be in every shot you send me from now on. I liked the half shirt with the bra beneath it, wear something similar today and start with the "thong" only but end the shoot bottomless.

4)From now until you have thongs you'll always pull your panties between your cheeks like a thong when you send photos

5)You didn't have a sign. Today you write "you own me daddy." and put it in some of the pictures, but don't ever let it block your ass.

You'll be punished again today for not carefully obeying my instructions, not having an original sign. Last time you didn't get a pic from me but 2 days in a row? Hmmm maybe you won't get instructions at all tomorrow? If you can't be an obedient slut then are you even worthy of the time I take to write them? You better really impress me today slut, maybe surprise me by taking some of your whore photos somewhere better lit and more public than you did last time, I don't know. But if you don't find a way to make it up to your Daddy today and beg for him to forgive his nubile young slut then who knows when you'll hear from me again...

-Daddy

These pictures are under the gallery "My first sissy pictures 4"

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Daddy,

Please forgive your little slut. I tried to make it up to you this time. I was home alone for a few hours so I took pics in my sisters room and living room. I really felt slutty being on my sisters bed in her clothes. Please humiliate me more Daddy.

Daddy's Bitch

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Then that was the end. I'm not sure if anyone will actually read and enjoy this, but I was deleting all of my old emails and instead of deleting this forever I decided that I should post this here so I won't forget about this. Has any other sissy out there experienced something like this?? If you have please tell me about it I'd love to hear! If you haven't, you should post in the comments that you want to and maybe you will get lucky. :)
発行者 SissySandyy20
6年前
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