Sissy Tiffany Meets New Daddy

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A sissy meets a Daddy for the first time.
1.7k words
4.5
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I sit here broken hearted as Master Gene informed me he was moving across the country for a better work opportunity and now gone from my life. Master asked me to go with him but as much as I love and care for him my roots are here and stayed. A very hard and difficult decision for me. Master Gene has released me from servitude to him and now I am not sure what to do. Did I make the right decision not going with him as tears form in my eyes wondering if I will ever find happiness and love with another as I did with Master.

I found one man online since Master and met him on a Saturday afternoon as I was longing for a man and his cock to serve. Even though serving him for sex was great and I did quite a few things with him I knew he was not my type for a long term relationship. But this is not about him, maybe another time, and about my new Daddy.

Sitting at home alone not knowing what to do dressed in my pink lingerie I finally decide to get back on my tablet and go to the website I found Master on. Scrolling across the profiles I finally come across one that perks my interest and clitty. Not a Master, but a Daddy looking for a sissy to be his girl and only about 15 miles away in the adjourning town. Something new to me a Daddy, not a Master, and wondering should I contact him as not sure about this type of relantionship but no other profiles close to me even sound interesting. And I do need to get out of this funk I am in. In essence I need a man in my life.

Seeing he is online now I decide to message him and see what happens. I message "Hi Sir, I am a very submissive sissy, Tiffany, who dresses femme and see you are looking for a sissy to be your girl. Please check out my profile and pictures and let me know if you would be interested in me." Now the dreaded waiting starts to see if he will answer back.

What seems like an eternity I finally see a message from him pop up. "After reading your profile Tiffany and seeing your pictures I am defiantly interested in meeting and auditioning you as being my new girl. I need you at my place this Saturday morning at 11:00 am if you are serious. And you must obey my instructions for entering my house. Daddy."

"Yes Daddy I can be there and will obey what you want" I message back.

He, Daddy, sends his address and instructions for what he wants this Saturday. I will arrive in my male clothes and bring a bag with my pink thong panties, matching bra, black thigh hi fishnet stockings, black heels, and the blond shoulder length wig I had on in one of my profile pictures. When entering I will not look at him but straight ahead and there will be a desk I should strip naked at and bend over placing my palms down on the desk and do not move.

Saturday arrives and having packed my lingerie the night before I shower completely shaving my body and dress to go, having butterflies in my stomach as I do. A short 20 to 25 minute drive but must admit a little nervous, but excited at the same time. Arriving I walk to the door and seeing a video doorbell I ring, my excitement rising. "Come on in Tiffany, the door in unlocked" I hear him say in a very masculine voice.

Opening the door I enter knowing not to look anywhere but straight ahead. I move to the desk with my head bowed down and as directed in his message strip and standing naked bend over placing my palms on the desk and wait. And then I realize as I wait there the blinds are open on the window and now wondering if others can see. Did Daddy do this on purpose testing me? I hear movement and then feel strong manly hands on my shoulders while hearing "Do not worry Tiffany as Daddy will never hurt you." His hands move down my back to my hips and then spreading my ass/pussy cheeks open. "Looks like a nice tight pussy for Daddy, Tiffany. I like what I see of your body." His hands move back to my shoulders and I now feel his cock grinding across and against my pussy. And it feels so good. After a few minutes Daddy stops and I hear him moving and sitting down I think.

"Turn around Tiffany and come over here to Daddy. I want you to drop to your knees and show me how good you can suck Daddy's cock." Turning around I see him for the first time as he had no pictures on his profile page. Sitting naked in a recliner chair waiting for me. Luckily for me Daddy is very handsome and has a fairly large cock and I find myself instantly attracted to him.

I walk to Daddy, dropping to me knees and say "yes Daddy," as I reach slowly stroking his cock and move my tongue licking his piss slit.

"No hands, Tiffany" I hear Daddy say and I immediately remove my hand from stroking his cock and wrap my lips around his cock head, my tongue swirling around the tip. Wrapping my lips tighter around his cock I slide them down his now hard cock, gagging some from his size, but swallowing all until my face is buried tight against Daddy. Hard to breath but I so want to show him how good a cocksucker I am. I feel his hands holding the back of my head as Daddy starts fucking my mouth. I so needed this I think in my mind and it seems Daddy is enjoying me also.

After a few minutes Daddy stops, withdrawing his cock and tells me while pointing "that door is my bedroom. Go inside and put on the lingerie I told you to bring, your heels and wig, and lay down across the bed and wait on me."

I do as he has said putting on my pink panties, bra, stockings, heels, blond wig and lay across the bed waiting. After a few minutes I see Daddy walking in naked still his cock now semi-hard. "You look very nice Tiffany, better than I imagined from your pictures." Reaching into a dresser drawer he removes a bottle of lube, and after handing me the lube Daddy says "lube up that pussy for me as Daddy wants to fuck you like a real girl with your lingerie on." I take the lube from Daddy pulling my thong to the side and squirt lube in my pussy and hands massaging deep inside me, getting ready for Daddy's cock.

Looking I see Daddy stroking his cock, now so hard again, and says "yes baby girl play with your pussy making it real moist for Daddy to fuck you. You want Daddy to fuck you baby, don't you?"

"Yes Daddy I need your cock deep inside me, please" I answer back so built up with passion now finger fucking my pussy faster and breathing harder.

Daddy moves to the bed grabbing my ankles and pulls my pussy to the edge while looking straight into my eyes. Lifting my legs exposing me to him I instinctively pull my thong to the side while Daddy moves forward his hard cock at my pussy opening. He lets go of my legs and I bend them over towards my face as Daddy guides his cock inside my pussy ever so slowly, our eyes locked together. Now deep inside me Daddy stops to let us both feel his entire shaft inside my pussy and then without hesitation pulls back out and thrusts hard into me. I cannot describe how good this feels and I want every inch of his cock and without thinking hear myself shout loudly "Oh Daddy, please fuck my pussy, please Daddy, please fuck your sissy girl." Daddy starts pumping faster and harder as I move my legs placing on his broad shoulders and around his neck holding him against me. I can't contain myself moaning and shouting for Daddy to keep fucking me.

"Does Tiffany want Daddy to breed her" I hear in between Daddy's heavy breathing.

"Yes Daddy, please bred me, please make me your girl" I answer back and feel Daddy fucking me faster his breaths getting more pronounced. I wrap my legs tighter around Daddy as I feel his cock throbbing inside my pussy and then one last deep thrust holding his cock deep inside me as my pussy fills with his cum. Such a wonderful feeling to have as his cock quivers inside my cunt releasing the last few drops of his cum inside me.

Smiling looking up at Daddy as his cock still in my pussy he looks down at me and bends over placing his lips to mine, our tongues reaching out swirling around each others as we kiss passionately, our first kiss. A bonus for me as I so love a man's lips against mine kissing me as his girl. Not a word between us, just smiles, as Daddy slides his cock from my pussy and lays down on the bed and motions for me to lay beside him. Moving up the bed placing my body against his, spooning, as Daddy wraps his manly arms around holding me as his girl. Even though I have just met Daddy I feel safe in his arms and lay here thinking I have met my new man to be in my life. And hoping Daddy feels that way about me, his new girl.

After a long time spent together in bed resting in a loving embrace it is time for me to leave. I remove my lingerie and really not wanting to now put back on my male clothes and after kissing Daddy goodby walk out with my bag of femme clothes towards the car.

I hear a voice saying "hi" and looking over see a couple of neighbors next to Daddy's house sitting in lawn chairs smiling.

I say "hi" and smile back but now wondering are they being friendly or do they know as I was very loud vocally in the bedroom and the window was open in front of the desk. But the thought for some reason excites me as I enter the car for my trip back home, still smiling, thinking I will be very happy having a Daddy in my life as his girl.

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ChloecrossedChloecrossedabout 1 year ago

Gorgeous story, and what a fabulous sounding Daddy. Xxx

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