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Date Night with Daddy

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Daddy takes his Femboy GF on a date.
2.8k words
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As always after work, I entered mine and Daddy's empty house, quite exhausted from my day. Daddy always worked an hour later than I did, which on a normal day would give me time to redo my makeup, change into one of my skimpy maid outfits, and have dinner ready for when he returned. However when I entered our bedroom, I saw a tight black dress, a garter belt and stockings on the bed with a note.

It read 'Don't worry about dinner tonight sweetie, get dressed in this and be ready for when I get home, Love Daddy x'

My heart raced in excitement as I stripped off my work outfit, a white blouse with a black pencil skirt, my most intact pair of tights, matching white bra and panties and my 5 inch black work heels. I was now naked, only wearing my black leather collar I always wore and the tiny metal chastity cage encasing my tiny penis. My 'clitty' Daddy called it, reminding me of his superiority each time he referred to it. He had a real cock, a solid 9 inches and very girthy. I was lucky he made me wear a black silicone plug in my boipussy at all times so I could take it. I looked myself over in the mirror, my long brown hair was tied in a bun whenever I was at work. My perky B cup breasts stood firm, a gift from Daddy, I felt them up, running my hands upwards to lift them, then let them go and they dropped straight back where they were. Since I got them I barely even felt my trapped balls anymore, which were a light shade of pink contrasting with my pale skin.

After admiring myself for a few minutes I lifted the dress off the bed and saw there was an app controlled vibrating buttplug underneath. I knew what Daddy wanted and removed the plug inside me and pushed the new plug in. It was shorter, but wider than my day to day plug, the new stretch would mean I would definately feel when it was turned on. Once I was done there I put on the garter belt and lifted the sheer black stockings up my smooth legs. I loved the feeling of stockings on me and took a moment to enjoy the sensation before I completed the outfit with the tight dress. I decided to forego any lingerie for two reasons, one being Daddy had not left any on the bed and the other being it felt a fun kind of naughty to have nothing on under my dress.

I looked at myself again in the mirror, I definately needed new makeup on me but I looked stunning. The dress clung tight to the beginnings of an hourglass figure. It also showed a lot of cleavage, Daddy loved making me feel like a slut in public, the most modest I got was when I was at work. I looked down and saw a slight outline of my caged clitty poking out, Daddy was sure to tease that I just knew it.

I sat at my makeup table and wiped off the cute, but hardly slutty makeup I wore to work. I fondled my finger around the various makeup products I owned before stopping at a deep red lip gloss I knew Daddy loved. I applied it slowly and sensually, watching as every part of my lips were coated in the wet gloss. Once that was done I did my eyeliner with cute little wings on either side, added a deep red eyeshadow above it and then did my mascara. When I was done I looked in the mirror and a complete slut looked back at me. I then had an idea for the perfect earrings to go with the outfit and after a couple of minutes of looking and putting them in, I was now wearing my deep red earrings that dangled from my ears to just above the collar on my neck. Finally I undid the bun and let my hair fall to my shoulders, it fell perfectly but I still gave it a brush.

I stood up and found my 6 inch slutty heels and stepped into them. My look was now complete. I trotted to the mirror in my heels and I looked like a whore. Exactly how Daddy would want me.

I was interrupted by the front door opening and closing. It was Daddy! I walked down the stairs as quickly as I could in my higher than usual heels. I saw he was already dressed in a smart shirt and trousers that clung tightly to his muscular legs. It was possible, if you focused your gaze there, to see the outline of his flaccid but still huge cock through them. He was generally muscular, and kept himself shaven from the nose down just to accentuate his form.

"Hey Daddy." I called to him softly as I approached him. Without heels in I was 8 inches shorter than him, but now I was almost his height.

He looked up and his dark eyes went wide for a split second before smirking at me. "Well hello beautiful, I see you're ready for our date night." He pulled me in for a kiss and was gentle on my lip gloss, I was sure he didn't plan to ruin my makeup until later.

"Ooh, date night?" I was surprised and excited. "Where are we going Daddy?"

"That nice restaurant on the other end of town baby." He looked me up and down, fixing his gaze on my tits before looking down to the outline of my cage. "You looking like a whore drive me crazy!" He growled, trying with every fibre of his being not to take me there and then.

"Thank you Daddy." I hummed. I saw his hand move slightly in his pocket and the vibrating plug in my boipussy buzzed to life, causing me to let out a pathetic squeak.

"Good to see you put that plug in, slut." He smirked. "I'm going to have so much fun teasing you tonight."

We got in the taxi Daddy had ordered and once it got moving he turned up the vibrator again, causing me to cross my bare, smooth legs and squirm. He leaned in close and kissed my ear before whispering into my ear. "Don't you dare cum from this while we're out sweetie, I don't want to have to punish you." His low, dominant tone told me he was being serious.

He turned the vibrator down again and I said "Yes Daddy, I'll be a good girl." Barely audible, but he could hear me.

He groped one of my tits and whispered to me again. "Good girl."

The restaurant we went to was nice, not posh, but nice. Me and Daddy got a table with a candle between us. When I sat down the plug hummed to life again. I had to conceal a moan and looked up to Daddy, pleading. He looked up from his menu and smirked, turning it up for a few seconds before it died down.

We got our food, Daddy had a large steak and I ate a small margarita pizza dish. Besides his food he had a beer and I had a glass of red wine. When I went to take a sip the vibrator went on again, nearly making me drop my glass.

"Oh sorry." Daddy half laughed, letting me put my glass to my lips. When I was going to put it down after a nice sip of wine, the plug went on again, very intense this time. This caused my hand holding the glass to shake and I spilt a small amount of wine on my tits. I looked down and saw how the red liquid ran down from my breasts into my cleavage, I could feel Daddy's glaze on me and I knew he was getting hard. I decided not to wipe it off, if he was going to tease me then I could have my fun.

I leaned forward, showing him my wine covered cleavage and then went to eat. Daddy must have found a setting he liked because the vibrator hummed in my boipussy the whole time I was eating.

By the time we had finished our desert and drinks, the constant vibration was sending me to the edge. My caged clitty was so close to cumming from the stimulation. My face went red, I wanted to be a good girl but this vibrator felt so so good. Finally after the bill was paid, and me intensely concentrating on holding off an orgasm, the vibrator stopped.

I breathed a sigh of relief as Daddy stood up and offered me his hand to help me up. I took it and my legs were shaking so I held onto him. He waved it off to the waiters and other people we passed on the way out, claiming I was a lightweight with the wine.

Back in the taxi on the way home, Daddy pulled me to him and kissed me deeply, turning on the vibrator again on the highest setting. I moaned into his mouth while he grabbed and squeezed my tits hard. His hand ran down to the bump in my dress caused by my cage and growled. "Good girl, when we're home you can cum from me fucking your little boipussy."

"Thank you Daddy." I moaned quietly. His kissed me again, groping me all the way home.

Once we got in he lead me to the bedroom by the ring of my collar. I could see through his trousers that he had a raging hard on. We got to the bedroom and I dropped to my knees, desperately working at his zipper. He helped by undoing and stripping out of his trousers, I sucked on his cock hungrily and took it down my throat while he stripped naked. He groaned, satisfied with how I was pleasing him with my mouth.

After a few minutes he pulled me off his cock by the back of my collar and looked down at me, getting full view of my cleavage. I went a step further for him and ran the straps of my dress off my shoulders and then I pulled it down to expose my fake tits fully. They stood there firm, I swayed from side to side, which caused his cock to throb.

Daddy then picked me up so I was standing, and then quickly pushed me on the bed. He lifted my legs while I lifted the tight skirt up, exposing my plugged boipussy and caged clitty to his massive member. He hovered his cock over my tiny trapped clitty, he liked doing this, it showed that this was how it always should be. I felt slight nervousness at the idea of being fucked by it, even though it happened at least once daily in the 2 years we had lived together. I felt the vibrating buttplug slowly pull out of my boipussy and Daddy showed it to me before putting it down on the dresser.

He turned his attention back to me, lifting my hips and gently rubbing the tip of his cock around my slightly gaped hole. "You want my cock baby?" He smiled down on me.

I was craving it at this point. "Please Daddy, fuck my boipussy deep and hard! I need your cock Daddy!" I begged while he teased my entrance, essentially ignoring my pleads for him to enter.

He looked up to my wide, makeup covered eyes and smirked. "Of course I'll fuck you sweetie, all you had to do was ask." As soon as he said that he pushed his cock slowly into me until he was balls deep. I felt my hole stretch around him and moaned as he filled me with his meat.

Daddy wasted no time thrusting into me as if I was a sex toy. Which in this situation, I was. He bought my hormones and even gave me breast implants so he would have yet another part of me to grab and play with. I cried out while my ass was subject to his rough treatment, but that didn't matter, I also craved this, and most other things that pleased Daddy.

He continued to pound into my boipussy. The head of his cock impacted with my prostate with every push into me and I could feel it in my trapped little balls. He grabbed one of my tits and squeezed and twisted at my nipple with his finger and thumb. The pinching pain only added to the caged orgasm that was building inside me.

"Daddy! Daddy I'm gonna cum!!" I practically screamed. The constant teasing with the vibrator throughout the night, the hard fucking currently going on, me cumming in my chastity cage was inevitable. My whole body trembled with multiple waves of pleasure in one, being pushed up my body each time Daddy's hips hit my ass, as an orgasm swept over me. My hole clenched on Daddy's cock and my cum dribbled down my balls, dropping down on his cock and being thrust back into me as he didn't relent.

"Oooh what a good girl." Daddy growled. He fucked me harder using my cum as extra lube, whiched helped with how tight I now was. After a minute or so of taking advantage of my orgasm, he groaned loudly, squeezing both my tits as hard as he could with both hands. I moaned as I felt the warm feeling inside me, his cum coated and filled my boipussy to the brim. Some cum leaked out from me when he pulled out.

Daddy took a moment, then scooped up the little bit of cum from our bed sheet and put his finger in my mouth. I closed my mouth around his cum covered finger and sucked on it, savouring the sweet taste of Daddy's special juice. He then took his finger out and hooked it in the ring of my collar and slowly pulled me towards him. I stood up from the bed and then squatted in my high heels before gently licking and sucking his cock clean.

I stood up again and he kissed me deeply, his tongue overpowering mine since all my strength had just been fucked out of me. I wrapped my arms around the back of his neck and pulled in close. Once he pulled away from the kiss, I asked softly and out of breath. "Was I a good girl Daddy?"

He responded by hugging me tight and telling me. "Sweetie, you're always the best girl ever." I loved when he got all sweet like this, this kind of reward made everything I'd do to please him worth it. "We should get you in the shower, you're a bit of a mess." He chuckled. I turned to the mirror and saw I looked even more like a whore than before our date.

In my reflection I saw that my hair was frazzled, my eyeliner had run down my face, my lipstick was ruined. My dress might as well been a corset. My tits were exposed and had red marks where Daddy had grabbed them, my nipples were bright red and sore and a little bit of cum hung from my caged clitty, still holding onto it. I turned back to Daddy and nodded before stripping naked.

He kissed me again as he picked me up and out of my high heels and took me to the shower. He put me down on my now bare feet and took my collar off from behind me before I stepped into the large cubicle in our bathroom. We showered together, Daddy would plant light kisses all over my body while he lathered me in soap. I shampooed and conditioned my own hair while I turned and watched Daddy clean himself in the running water. He was just so sexy, and still kind of hard.

I licked my lips and dropped down to my knees. I took his cock back in my mouth and he moaned, it was still sensitive from just moment ago. That didn't stop him from enjoying it and soon he shot another load of cum down my throat. I stood back up and kissed him before I finished washing myself and got out of the shower to grab my towel.

I was nearly fully dry when Daddy joined me out of the shower. "I'll only be a minute sweetie, you get nice and comfy in bed." He said, kissing my cheek from behind.

"Yes Daddy." I smiled and finished drying myself. While I did own a lot of sexy nighties, I decided tonight I would sleep naked. Besides my chastity cage of course. Daddy didn't take long to join me and I snuggled up to him. He pulled up the covers which were cool against by bare skin, and then warmed me up by wrapping his arms around me.

I inhaled deeply, taking in his freshly showered aroma. I could feel my eyes struggling to stay open.

"Goodnight sweetie." Daddy yawned. I responded by snuggling up even closer to him, making him hum happily. We would then fall asleep like that. I love date night with Daddy.

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AnonymousAnonymousabout 1 year ago

What a beautiful story it has me hard and my boipussy tinging around my plug. Oh daddy where are you. I need you so bad. Please take me and fuck me hard. To be plugged in chastity and collard with pretty girly sissy clothes on what a dream. Then to have daddy spank and cane me while my clitty is squealed tight ooh daddy I am all yours to use.

AnonymousAnonymousover 3 years ago
Wow

I dream of this......

AnonymousAnonymousover 3 years ago
Wow

Now that is the definition of a real man. Rough when required and kind and gentle afterwards. I'd date him lol.

AnonymousAnonymousalmost 4 years ago
OMG!

I wish this story was longer but you outstripped so many others with yours, you had prep, flirting, teasing, great sex, FUCKING AFTERCARE!!!, and such lovely characters. Five stars from me on this

garter2000garter2000almost 4 years ago
Omg your sissy... delicious

I’m licking my sissy cream

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