I'd find high class escort agency and ask for a sexy blonde woman, mid 20's who loved high heels and wouldn't mind spending a day shopping for some and then for some kinky fun afterwards.
We would go to expensive boutiques and buy several pairs. Strappy high heel sandals, a perfect black leather pumps to go with that little black dress, and then maybe something more risque. Maybe fire engine red fuck me pumps, or something that is an exotic color.
On the last pair I'd whisper in her ear in the store what do you think would look best with your pussy wrapped around it? These shoes are costing me a fortune and your going to have to earn them tonight.
At the hotel I'd make her dance for me, stripping down to just her garterbelts, stockings and high heels. I'd watch her lean back on the bed and finger herself as I pull out the sandals. I would instruct her to fuck herself with the sandals, sliding the long thin heel in and out of cunt. Slowly watching her amuse herself I get naked and onto the bed, taking the sandal out of her hands I would slowly fuck her with it. Teasing and taunting I'd ask her if she ever had something so expensive in her cunt before. I would push it all the way in and grind it against her pussy. Just as she is about to cum I would stop, and make her get off the bed.
I would tell her how she has been teasing me all day with her fuck me pumps and now it was my turn. Taking the elegant black pumps out of the boxes I would put one shoe between the cushions of the sofa so the toe aimed up. She would bend over at the waist and lick and suck on it like a cock while she spread her pussy open for me to watch. My camera would come out and take pictures of her lovely body. Stepping behind her I would take the other heel and gently slide it into her body, fucking her with it. Then I would rub the toe up and down her slit to let her get a feel for the size. Pushing the slender heel into her pussy again I would leave it in her and step back, watching it dangle from her pussy telling her how slutty she looked with the heel dangling out.
Turning her around, I would lay her onto the sofa with her legs open wide. Using a bottle of lube I would make sure she was nice and slick, and I would apply a good amount on the sandal too letting her know she would fuck this first since it was smaller than the pumps. Turning the shoe sideways I'd rocking the toe up and down against her slit, pushing firmly as she cries out softly. I would take my time, and slowly work it in after long time til it is at least half way in and her pussy lips are wrapping tightly around it. Grabbing the heel I would rotate it around her pussy stretching her out til the heel juts upward like a handle. Gabbing it I would fuck her with it til she came. Pulling the slick sandal out I would push it back in, this time I would put the other pair in as well laying them flat so the heels point in my opposite directions. Leaning back I would enjoy the work I did, taking pictures and letting her know how sexy she was wearing two pairs of heels at once.
Leaning forward and whispering in her ear to sooth her, telling her how it the hardest part was done. Her reward would be the thousands of dollars worth of shoes in the room how each pair would be hers if she wore them for me tonight. Place the camera inches from her pussy I'd tell her to pull the sandals apart for the camera so i could get the perfect shot. She pull them apart but it hurt, I'd ask for more til I saw her tender pink hole spread open wide enough. It would be a heavenly sight with high heels jutting out of her pussy, her pink tunnel parted with the the intials D&G clearly stamped onto the leather of the shoes, Dolce and Gabbana.
After getting the shot I would take her red "fuck me pumps" out of the box and work it against her til it slipped it, firmly nestled into her pussy with the heel aimed towards the ceiling. I would make her beg me to fuck her with her fuck me pumps and I would do it hard til she screamed as she came.
With heel shoved into her pussy I would slip my cock into her asshole and fuck her hard. Just before I cum I would pull out and stick my cock into her shoe stuffed pussy and cum deep inside her. As she laid there spent with a few more photos I would allow her to pull her shoe out of her cunt and get dressed.
As I sit on the bed watching her move around the room collecting the shoes that were discard about the floor, amused at the funny way she walked now. She slip her sexy short black dress back on without her lace black thong, her pussy was much too sensitive to have it rub against her now.
As she comes for the thick fat envelop filled with 100's I would say "Stop, we're not done yet." Bending her over the desk I would pull her dress about her waist, and strip her heels and stockings off her long sexy legs. Then I would take her heels and slip them back onto her feet as she spread her pussy open for me again.
I would tease her by saying I couldn't let a lady like her walk out of the hotel not properly dressed, without underwear it would be scandalous. I would push the black thong deep into her pussy. Then I would take each stocking and push it into her wet cum filled pussy so that just a little poke out between the lips. Leaning back I would admire the fine feminine form in front of me, bent over in heels with her pussy stuffed
"Besides I wouldn't want you staining the hotels carpet with cum as you left. Let me walk you to the limo."
I would walk behind her in the halls, admiring the way her hips swayed as she tried her best to pretend everything was normal. I would smile to myself because I would be the only one to know why her legs are bare. Watching her navigate the lobby I would hope that maybe I get a tiny glimpse of some stocking peak down from below the hem of that short short dress she was wearing but would be disappointed. Helping her into the limo I would slip her another envelop with a huge tip and complimenting her on her performance.
Inside the limo would be a hidden camera to watch her pull her stockings out of her pussy on the ride back.
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