She said she couldn’t find a hat that looked good on her. I didn’t believe her. I took it as a challenge. It was a matter of confidence. Hats are about a vibe or a feel or an attitude to project. One has to sell a hat. But, yes, they also have to fit. They need to fit the woman’s face and hair. The style of the hat needs to fit the style of the woman.
I took the challenge seriously. Because I knew there would be a payoff. The payoff would be decadent. The payoff would be hot. The payoff would be everything I could imagine it to be.
I had a month before the Derby party. It was enough time.
I started by ordering three different hats that could serve as a good base for a Derby hat. I had a plan. And after six trips to Michaels and two visits to the florists, I had the supplies I needed. I crafted with care. Imaging how she would look. I took my time, concentrating on the delicate details. Focusing a gentle touch with a stitch here and drop of hot glue there. There were feathers and bows, lace and ribbons, pins, string and wire.
One was tan with creamy white and pastel yellows. It would go with a yellow sundress.
One was black and would go with the white and black polka dot dress.
One was purple, my favorite color. The color of sex.
On Saturday afternoon around noon, our date started. Before showering, I laid out the options for her. I was her dedicated fashion coordinator. I shopped for her. I shopped with her. I was also her valet. Her towel boy. Her foot stool. Her massage therapist and cook. I did every thing because she was my everything. And she deserved it. And I loved taking care of her.
On the bed, I had placed the three dresses, along with the heels that would go with each. I couldn’t decide if I should put the hats out with the dresses or let her choose the dress, which would then dictate the hat.
I decided that it was all about the hats today and they needed to be in the decision making process. She knocked on the door and asked if she was allowed to come in yet. I opened the door for her and took her by the hand and walked her to her options.
She had just got done working out. She looked strong and sweaty. Much different than she would look in about an hour.
She was suspicious of the hats.
We will have to get cleaned up and then try them on, she said. Draw my bath.
I laid down the yellow sundress I was holding and went to the bathroom and turned on the water. I poured same bath salts in the tub, along with a generous amount of bubbles. I placed a hand towel on the side of the tub and hung her clean white towel on the hook.
She walked in. Undress me, she said.
I pulled her shirt over her shoulders and head. Then her athletic bra. I knelt down and slid off her socks. Then pulled at the waistband of her shorts and lowered them. She stepped out of them, putting a hand on the top my head for balance. Her waist right in front of my face. She directed my head to her pubis mound.
I breathed her in. Her scent was strong, a combination of sweat and sex.
“Test the water,” she said.
I put a hand in the bubbles and adjusted the flow accordingly. I tested again and told her it was ready for her. With her hand on head and me kneeling at her side, she stepped into the bath tub. Her legs and ass looked amazing. They disappeared beneath the froth of lavender scented bubbles.
I had forgotten the washcloth. I hurried to the linen closet and got one.
“Did you forget your responsibilities, my pet?”
“I’m sorry, mistress,” I replied. “I won’t let it happen again.”
“Strip,” she said. “You also know you are supposed to be naked.”
Without being told I ran to the kitchen and brought back a glass of white wine. Unoaked chardonnay from Chapelet. I handed it to her.
She took the glass and lifted one leg out of the water and set it on the edge of the tub for my attention. I wet the washcloth and cleaned her elegant leg. I washed every inch of her body. I washed her hair, slowly and softly. Rinsed it with clean warm water.
She liked to rinse in the shower. She also liked to tease me there.
It was her turn to use the soap and washcloth on me. Not for me, but for her. Preparing me. She scrubbed me aggressively. Then she took the bar of soap in her hands and rubbed up a handful of suds.
“Turn off your water,” she said.
I stood before her and with her soapy left hand she stroked my cock. It quickly came to attention and grew in her hand as she slid it up and down. She was forceful, like she was in a hurry to make me come, but I knew that wasn’t her plan. She got it nice and rigid and squeezed the head and the end of each stroke. Then she cradled my balls and raked her nails across my taut scrotum. She ran her hand up and down some more and when I tilted my head up and closed my eyes, that’s when she took her soapy right hand and put it on my ass.
My eyes opened quickly and I looked at her and sawyer mischievous grin. She soaped my glutes and explored the length of my crevice,makign me squirm in delight. She worked her fingers around my hole, teasing me with her fingers and eyes at the same time. I shuddered in pleasure and she quickly stopped stroking my cock.
“You know you’re not allowed to come.”
Yes, mistress, I understand.
She smacked my cock just to make sure I had no illusions of accidentally coming before she allowed it.
“You’re going to come later,” she said. “Would you like to know when and where?”
“You’re going to come in the bathroom at the Derby party.”
“You are,” she said. “And do you know when you will come?”
I shook my head no, hardly believing the first part.
“Right as the horses cross the finish line.”
My eyes widened. My thoughts raced. Oh my goodness.
She picked the purple hat and the purple tie that I bought to match. I was wearing a blue sport coat. We wore matching gray panties with purple polka dots.
The party was swanky. Rich people who spared no expense in the details or the bourbon. Alpha males full of themselves and women dressed to impress. None of them looked as good as the one in the purple hat.
We sampled drinks. We discussed which dresses we liked and who might be an ideal third partner in the bedroom, although that was just to get me excited.
We tasted bourbon and we placed bets on the horses we liked.
We snuck off to the upstairs and wandered through the master bedroom and out onto a deck that overlooked a lake. She dug into her purse and pulled out a joint and a lighter. She post the joint between her lips and handed me the lighter. I set my bourbon down and cupped my hand around the flame and lit it for her. She breathed in deeply as the tip glowed red. She pulled the joint aside and put her other hand behind my head and pulled me toward her. I opened my mouth and our lips touched and our eyes met as she exhaled her smoke down my throat. She repeated this twice more before stabbing out the joint and flicking it over the railing.
She put the lighter away and pulled out a small blue pill.
“Take this now,” she said.
She placed the sildenafil in my open palm and I washed it back with the bourbon.
“It’s thirty minutes ’til post time,” she said. “I need you ready to ride.”
We went back downstairs and I fetched her another drink. We sat at a table and she placed her hand on my thigh and started caressing me.
I could feel the combination of anticipation, the touch, and the pill start to make my cock come to life. Then she grazed it with her hand, almost as if to check on it. She smiled. A smile that said, good boy.
The horses were in the paddock and the jockeys were introduced.
She excused herself to go to the bathroom. When she came back, she leaned in to kiss me on the cheek and whisper in my ear.
“When they sing My Old Kentucky Home, you are to go to the upstairs bathroom, smell these and start stroking your cock.”
I looked down and she had stuffed her panties in the inside pocket of my sport coat.
I nodded. She smiled. And we returned to small talk among friends as her hand went back to my thigh.
As the race drew near and people gathered in front of the TVs and made exclamations about their feelings on who would win, I slipped upstairs hoping nobody noticed my semi erect cock jutting sideways in my pants.
I went to the bathroom and locked the door. I slipped off my jacket and hung it on the back hook. I undid my belt and untucked my shirt. My pants slid to the floor. I stroked my cock through the panties, letting it lengthen and push against the silky gray and purple panties.
I pulled it out and stroked it more vigorously. I held her panties to my my face and breathed in her scent. They were still spotted with her wetness. I thought about my mistress and her legs. And her ass. And her eyes. And her smile.
The anticipation was killing me.
There were three knocks at the door.
I let her in and closed the door behind her, locking it.
She smiled and quickly put her mouth on my hard cock, getting it wet.
She stood up and put her back to me and leaned over the vanity. She pulled her dress, exposing her bare ass. She looked at me in the mirror.
There was some commotion and noises from the party below. The race had started.
“Fuck me, lover,”she said.
I plowed my rigid cock into her wet pussy. I held her by the hips and looked into her eye in the mirror. With just a couple of strokes, I had worked myself all the way in and was picking up pace.
The shouting from the race fans continued.
My pace quickened. My hips smacked against her ass. Faster and louder. She closed her eyes and moaned.
“Yes,” she said. “Harder. Faster.”
I kept pumping, leaning into her, rising to my toes to give her everything I had.
“Oh yes,” she said. “Give it to me.”
The crowd below crescendoed as the Derby came to its climax.
I gripped her hips hard and gave one last deep stroke before shaking and rocking in an orgasm that thundered through my entire body.
I gave her two or three more strokes to give her every last drop and shudder.
She stood up and turned around and took my cock in her mouth, cleaning off the combination of my load and her juice.
“Mmmm,” she said. “Good ride.”
She pulled her panties back on and walked back down to the party.
When I came down, she was smiling and holding a handful of cash.
“We won,” she said. “The jockey with gray and purple silks won by a nose.”
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