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Description
Hank was your run of the mill 20 year old guy, but little did he know his life was about to change drastically soon.

I went to the gym like i did every thursday night but when me and my girlfriend with whom i always worked out entered the gym there where only woman working out this evening "heaven on earth" i whispered to myself as i looked at the legging clad women using the workout equipment. "Seriously?" My girlfriend said with an smirk "what? I just love women" i responded jokingly "especially Cara Delevingne" we both finished my sentence at the same time.
"Well why dont you go and sleep with her then?" She said becoming more jaelous as this conversation went on "as if that is so easy to do" i said jokingly but it became apparent to me i said something stupid again, but it took a while before my girlfriend started talking "there is an way you know?" She then finally said with the smirk she had in the beginning, i knew this wasn't going to end good for me but before i could do anything she grabbed my hand and dragged me out of the gym.

When we came back to our appartment she threw me on the couch "i like where this is going" i said as i laid there on the couch and as she ran into our bedroom i heard her opening the closet ang grabbing something "me too baby" she said as she walked out of the bedroom with an white t shit a sequin tiger print skirt and some fishnet tights "that will look good on you" i said as i got up and grabbed my girlfriend's hips "and it will look even beter on you... Cara" she whispered seductively in my ear " wait what?" I asked "Cara? What do you mean?" "I mean that we are going to do a little dress up" she said with an evil grin "well why would i humiliate myself like that?" I asked her "you know what if you can dress like Cara Delevingne for a whole month 24/7 i will let you fuck me whenever you want for the rest of the year" she said pretty convinced, and it did sound pretty tenpting so i almost said yes right then and there but then i realised this was no challenge but a bet "and what if i lose?" I asked her "then i can fuck you with a strap on while you are dressed as Cara Delevingne" she said immediatly, i was never one to let down a challenge eapecially if it meant unlimited sex for the rest of the year! And it's only april! "DEAL!!" I yelled determined.

Shortly after i accepted the bet she sat me down on the bathroom toilet and shaved all of my body hair, next she grabbed her makeup kit that she normally used for work and started to slather me with makeup after makeup after what felt like an eternity she grabbed hair extensions and applied them "thankfully you are a proffesional makeup artist" i said in the hope of looking like a good woman.
Then after a few minutes she stepped back and threw the clothes on my lap "put these on Cara" she said teasing me,
And as i got up i felt the hair feeling unnatural to me so i slicked it back over my ears.

Then i started to get dressed, i started with a matching blue bra and panties when i slid the panties over my slick legs i felt humiliated especially after seeing tge bulge my penis made in the panties "how am i supposed to look like a hot chick like this?" I said to my girlfriend who slid her hands into my panties and grabbed my penis, at first i felt aroused but then she pulled it back seperating my testicles "this doesn't feel well" i said almost with an higher pitched voice "you'ill get used to it" my girlfriend said "now get dressed Cara"

After that she left the bathroom as i dressed myself into the shirt skirt and fishnets, once i was done i grabbed the heels she left behind for me and strapped them on my feet. I then walked towards the door wobbling on my ankles, once i entered the living room my presence was announced by the clicking sound of the heels "oh my god" she gasped as i turned the corner whilst holding up her phone, but before i could do or say anything she snapped a picture of me and when she showed the oicture to me i couldn't believe how good i looked "that looks like Cara Delevingne" i said in disbelieve "you get to enjoy yourself like this for 30 days now baby" my girlfriend said

Description
Hank was your run of the mill 20 year old guy, but little did he know his life was about to change drastically soon.

I went to the gym like i did every thursday night but when me and my girlfriend with whom i always worked out entered the gym there where only woman working out this evening "heaven on earth" i whispered to myself as i looked at the legging clad women using the workout equipment. "Seriously?" My girlfriend said with an smirk "what? I just love women" i responded jokingly "especially Cara Delevingne" we both finished my sentence at the same time.
"Well why dont you go and sleep with her then?" She said becoming more jaelous as this conversation went on "as if that is so easy to do" i said jokingly but it became apparent to me i said something stupid again, but it took a while before my girlfriend started talking "there is an way you know?" She then finally said with the smirk she had in the beginning, i knew this wasn't going to end good for me but before i could do anything she grabbed my hand and dragged me out of the gym.

When we came back to our appartment she threw me on the couch "i like where this is going" i said as i laid there on the couch and as she ran into our bedroom i heard her opening the closet ang grabbing something "me too baby" she said as she walked out of the bedroom with an white t shit a sequin tiger print skirt and some fishnet tights "that will look good on you" i said as i got up and grabbed my girlfriend's hips "and it will look even beter on you... Cara" she whispered seductively in my ear " wait what?" I asked "Cara? What do you mean?" "I mean that we are going to do a little dress up" she said with an evil grin "well why would i humiliate myself like that?" I asked her "you know what if you can dress like Cara Delevingne for a whole month 24/7 i will let you fuck me whenever you want for the rest of the year" she said pretty convinced, and it did sound pretty tenpting so i almost said yes right then and there but then i realised this was no challenge but a bet "and what if i lose?" I asked her "then i can fuck you with a strap on while you are dressed as Cara Delevingne" she said immediatly, i was never one to let down a challenge eapecially if it meant unlimited sex for the rest of the year! And it's only april! "DEAL!!" I yelled determined.

Shortly after i accepted the bet she sat me down on the bathroom toilet and shaved all of my body hair, next she grabbed her makeup kit that she normally used for work and started to slather me with makeup after makeup after what felt like an eternity she grabbed hair extensions and applied them "thankfully you are a proffesional makeup artist" i said in the hope of looking like a good woman.
Then after a few minutes she stepped back and threw the clothes on my lap "put these on Cara" she said teasing me,
And as i got up i felt the hair feeling unnatural to me so i slicked it back over my ears.

Then i started to get dressed, i started with a matching blue bra and panties when i slid the panties over my slick legs i felt humiliated especially after seeing tge bulge my penis made in the panties "how am i supposed to look like a hot chick like this?" I said to my girlfriend who slid her hands into my panties and grabbed my penis, at first i felt aroused but then she pulled it back seperating my testicles "this doesn't feel well" i said almost with an higher pitched voice "you'ill get used to it" my girlfriend said "now get dressed Cara"

After that she left the bathroom as i dressed myself into the shirt skirt and fishnets, once i was done i grabbed the heels she left behind for me and strapped them on my feet. I then walked towards the door wobbling on my ankles, once i entered the living room my presence was announced by the clicking sound of the heels "oh my god" she gasped as i turned the corner whilst holding up her phone, but before i could do or say anything she snapped a picture of me and when she showed the oicture to me i couldn't believe how good i looked "that looks like Cara Delevingne" i said in disbelieve "you get to enjoy yourself like this for 30 days now baby" my girlfriend said