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The next morning, Anna arrived at work more bubbly and cheerful than I had seen her before. She was wearing her usual outfit but I briefly noticed something different. I immediately noticed she pulled her skirt up just enough to reveal her stocking tops as she walked and the heels she was wearing made her calves and legs look more sculpted. Gone were the pantyhose, replaced with sheer white nylon stockings. Also gone were her flats, replaced with gorgeous 2″ black leather heels. I picked a bad day to wear nothing under my coveralls. Or, maybe, it was a good day…
During our morning meeting, Anna expertly dangled a heel in front of me and even turned so that her dangling heel was brushing my leg. I started to feel my cock respond. Suddenly, she let her heel slip off and it tumbled down my calf, across my shoes and onto the floor. That’s when I got the first look of her beautiful foot. Through the white nylon, I could see her toenails painted a deep crimson red. I remembered her mother’s toenails were also painted that color, back in the day. As she wiggled and spread her toes in front of me, my cock started to swell.
Thankfully, the meeting soon ended but Anna and I stayed behind. There was no way I could have stood up without the whole management team seeing my excited cock. Anna started to fish around with her foot to retrieve her shoe and, as she brushed my leg repeatedly, my cock sprang right out of my coveralls. Anna giggled and said “Ooops, did I cause that Mike?.” I just smiled and did my best to calm my cock down. I told Anna I would meet her on the shop floor shortly, her prompt to give me time to regain my composure.
Eventually, I made my way out to the shop floor, purposely grabbed a dead flashlight and hopped inside the same boat as yesterday. I was very glad I had a whole section, separate from the rest of the facility, to do my work. As I did the previous day, I crawled under the dash of this boat and called for Anna to bring me a fresh flashlight. I heard her climb the ladder and board the boat, drop off her work shoes and, like yesterday, I scooched out a bit and Anna stood over me.
This time I was treated with a perfect view of her white nylon stockings, her creamy inner thighs and her bald, slightly gaped pussy. Her pussy was as beautiful as her mother’s. I thanked her and pretended to get back to work. Anna would have none of that. She slipped one of her nylon covered feet in through flap opening in the front of my coveralls and put it right on my cock. She rubbed her warm and slightly damp foot up and down my cock until it started to rise.
Anna expertly guided my rising bursa escort bayan cock out into the open with her foot. I wasn’t sure exactly what she was up to but I wasn’t about to stop her. As she rubbed the head of my cock with her toes, gripping and kneading it, my cock got full raging hard. I thought of my wife, my marriage, my job but all I wanted in this moment was Anna.
Anna then squatted down and guided my cock inside her sopping pussy. Once my cock head was fully in, she just lowered her body down on me. Her gorgeous pussy swallowed my entire eleven inches of thick cock in one squat. She pushed a little harder down and that’s when I felt it; her cervix opened slightly and squeezed the head of my cock. It was just like fucking her mother, Kelly, again. I knew I would only last seconds before my orgasm boiled over. Sensing my imminent release, Anna quickly pulled off my cock and said “I’ll be at your hotel tonight Mikey.”
Anna stepped back, slipped her work shoes back on and got off the boat. Just as I thought I was about explode from being brought that close to the edge, Anna called in to me and said “I can’t leave you that way and I’m sure you’ll like these” as she gently tossed her heels into the boat. I grabbed her heels, put one on the floor and slid my cock into it. I started fucking Anna’s heel while I buried my face in the other one. In no time, I felt like I was going to cum right in her shoe and, summoning all of my willpower, I pulled out and relaxed until my urge to cum subsided.
When I finally made my way off the boat, I handed Anna her heels, one damp with a copious amount of my pre-cum and the other slick from my saliva. I thanked her and told her I enjoyed fucking them but I didn’t cum in them. I told her I wanted to save my best for her. I did almost blow my load when I saw her quickly take off her work shoes and slip her heels on. She commented on how they felt warm and nice as she stretched her legs out.
The rest of the day was torture. Anna dangled and dipped in and out of her heels as her skirt kept rising up to reveal her stocking tops and thighs. She did nothing overt but her actions were driving me wild. She was a master of teasing and I came to the conclusion she’d been working on me all along. What I took to be increasing carelessness was a planned process. She definitely knew what she was doing and quickly figured out what I like.
The rest of the day consisted of Anna teasing me with her gorgeous feet and allowing me glimpses up her skirt. At the end of the day, we said our goodbyes and Anna gave me a hug and kissed me hard bursa escort sitesi on the lips. Then, she reached into my coveralls and grabbed my cock as she looked me in the eyes and asked for the hotel information.
I gave her the information and asked if she’d join me for dinner at the hotel restaurant. Anna gave me a slightly sultry “it’s a date, see you at 6:00” as she let go of my cock, turned and walked away. Now, she had her skirt pulled so high that I could see the bottom of her ass cheeks. She was an amazing and complex girl coming out of her frumpy shell and I felt a strange sense of pride that I might be helping her. And that she reminded me of her mother and, despite knowing I used to fuck her mom, still wanted to be with an older, married man.
When Anna arrived at the restaurant, I barely recognized her as the girl I worked with every day. She had a dark blue, form fitting dress with the same white nylons and heels she wore to work. Her red hair was teased up and she was the spitting image of her mother. I’m glad I decided to put on some nicer clothes because what I originally had in mind would have been an insult to this beautiful girl. We picked a corner booth that afforded us the most privacy.
As soon as we sat down, our hands were all over each other. Anna grabbed the bulge in my pants while I caressed her nylon covered legs and made my way up to her stocking tops to feel them and caress her bare thigh. Anna spread her legs and I had two fingers in her soaked pussy before we even ordered drinks. Our waitress, Cheryl, was cute and around Anna’s age. She had to have noticed what was going on but she played it cool and took our order. When Anna was ordering her drink, I put another finger in her pussy, causing her to gasp slightly. She returned the favor by squeezing my cock when I ordered mine.
As we had our drinks, Anna told me to take my pants down. As I started to tell her I wasn’t sure it was a good idea, she cut me off and said “Do as I say, Mikey” There was a long tablecloth draped over the table, so no one would see my pants around my ankles. I did as I was told. Anna slid away from me in the booth and I heard her heels hit the floor. Next thing I know, Anna’s warm nylon feet were on my raging cock. My cock was trapped under the table, so Anna could do whatever she wanted to it with her feet. She stroked it up and down until Cheryl came back to take our food order. Just as Cheryl was taking our order, Anna moved my cock around so the head of it popped up to table level. ‘Oh my God’, I thought. The waitress is going to see my cock and Anna must have wanted that to happen.
Anna and I could tell by the look on Cheryl’s face when she saw the big purple head of my cock. Just as Cheryl started to look away, Anna pushed my cock away from the table towards my belly. This would have given Cheryl a view of my cock head and a few inches of shaft. Cheryl looked for a few seconds and then smiled at me. She finished taking our order and headed off.
Anna said “This feels wonderful but it’s killing my legs. I’ve got something else for you.” Anna picked up her heels and set them on the seat between us and then shifted back over closer to me. She took one of her heels and carefully jammed it onto my erect cock and tucked my balls into the heel cup and said “Leave that on, no matter what.” I was so excited, I couldn’t object.
“When Cheryl comes back with food, I want you to lean back so she can see my heel on your cock.” I didn’t know what Anna was up to but I was so hard and horny, I was ready to fuck her right on the table in front of the whole room. While we chatted and waited for our food and my cock throbbed inside Anna’s size 10 heel, I got an idea of my own. I picked up her other heel, pushed up her skirt and pushed the toe of her heel into her pussy. She moaned and said “deeper.” I pushed her heel in until I felt it pop in past the wide part of the vamp and she said “perfect.”
When I saw Cheryl coming, I leaned back and let my throbbing cock hold Anna’s shoe out in plain view. When I looked over at Anna, she had her one leg up on the bench, her skirt fully hitched up and the heel hanging rudely out of her pussy. Anna was going to show Cheryl what she was up to as well. When Cheryl reached the table, she almost dropped our food. She tried to be as professional as possible but her eyes betrayed her. She was looking at the heel on my cock and then the heel in Anna’s pussy. She must have enjoyed what she saw because she stood there until we thanked her.
I kept Anna’s heel on my cock and she kept the other in her pussy for the entire meal. Cheryl’s level of service was almost overbearing as she kept returning to the table to ask if we were OK. When we finished, Anna took her heel off my cock and pulled the other out of her pussy and slipped them back on her feet. She told me to lean right back and show Cheryl my whole, thick cock when she came back with the bill. Cheryl stared at my enormous cock as she waited for me to get my credit card out. She left to process the payment and Anna leaned over and began stroking my cock. When Cheryl came back, Anna just kept stroking my cock like she was putting on a show.
I left a modest tip and Cheryl left our table, thanking us and telling us to ask for her any time we were dining here. Anna and I straightened up and she left an extra $40 cash tip on the table for Cheryl. Something was going on and I needed to know what it was.
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