Chapter 1
Discovering My High Heel Fetish
I was 18 when I discovered my love of women wearing high heels. I'd seen beautiful women all over the place but it was women wearing high heels that really turned me on. Not just any heels did it for me, it was the taller heels, aka Fuck Me heels. Anything under 5 inches just didn't have enough sex appeal to me.
I remember one such time I was out with my family at a fairly fancy restaurant. We were under dressed compared to the majority but dressed up enough to be able to eat there. I was playing a game on my phone while my Mom and sister were chatting away about some nonsense and Dad had stepped away for a work call. I looked up when I heard the voice of the waiter and that's when I saw her.
Walking into the dinning area to be seated was a young woman, couldn't have been older than 25. She had on a simple dress with spaghetti straps. Her long blonde hair reached the middle of her back, and then I saw the high heels. Not just any pair of high heels but an extremely sexy pair of heels. They were a glossy black color, with a peep toe in the front, and the bottom or the sole of the shoe was a bright solid red color. She had blue painted toenails and a shiny silver anklet with a few charms dangling from it on her left ankle.
My hormones went nuts. My body felt all tingly and my cock sprang to life. The massive bulge in my pants was only slightly covered by the table cloth. When she reached her seat, it was like my internal body temperature spiked as I started to sweat some. Only then did I feel the kick from my sister as the waiter had apparently been trying to ask what I wanted to order. Embarrassed and quite flustered I quickly glanced at the menu and ordered the first thing that sounded good.
So there I was, sitting across from Mom and my sister with a raging hard on. I could feel it pulsing between my legs and didn't know what to do. Just when I thought it couldn't get any worse, the woman wearing those heels got up and walked right past me, strutting her shapely legs with those heels clicking all the way until she disappeared from sight. My cock ached so bad I was almost in tears. A minute later, Mom got up and went to the bathroom, leaving just my sister and myself at the table.
As soon as Mom was out of view, my sister looked at me with a weird look and asked what was going on with me. "I don't know what you're talking about." I told her. She didn't accept that answer and pushed even harder.
"You were fine when we got here but now you're all flustered and red in the face. Somethings got you all out of sorts. Tell me. I want to know." She said, sounding genuinely concerned, yet nosy.
Before I could answer her, the woman in heels walked back in. I totally forgot that my sister was looking right at me and because of that, she could easily pinpoint what I was looking at.
"Seriously bro? She's like 25. I bet she wouldn't even give you a snowball's chance in hell." With that remark she giggled then looked back at me.
"Honestly sis, I'm not even really that interested in her. For starters, her tits are too small and she's too skinny." I said as I tried to regain my composure. Confused, she looked back at the woman, no doubt examining everything about her now.
"Hmm ok, not the tits, too skinny, not much of an ass really. Wait a minute..." She says as she starts to figure out what has me all worked up. "You've got to be kidding me, her heels?"
The expression on my face and the body language I showed were the telltale signs she needed to know, she was right. Before she could say anything else, Mom and Dad returned to the table. Dinner went smoothly from then on out. We talked about random topics and I managed to keep my cock from flipping the table. Just as we were leaving, the woman with the heels got up as well. As fate would have it, I was on a collision course with her as we were both heading for the same doorway to exit the dining area.
Luckily my parents were already through the door, but my sister was right beside me. Mom, being the southern respectable woman she is, raised me to be a gentleman so when the young woman reached the doorway just after me, I took a step back and allowed her to go first. As much as that was the right thing to do, it was the worst thing for me as now I got to watch this attractive young woman wearing a pair of extremely sexy heels walk past me and my eyes followed. My sister got a front row seat to my body's betrayal and when she caught a glimpse of the bulge in my pants, I thought her eyes were going to pop out of her head.
"What are you looking at?" I asked.
"Uhm, that." She said as she nodded her head in the direction of my crotch.
Looking down, I saw the bulge in my pants. "Fuck sis, don't draw attention to it." I said, trying to adjust myself. Allison gave me a smirk, turned and walked away, but not before giving her ass a little shake just to fuck with me some more.
The drive home was relatively quiet. Normally Dad would drive but after big meals out, Mom drives because Dad always gets sleepy with a full stomach so he was doing his head nod thing where he falls asleep until his head drops. Allison was on her phone doing God knows what and me, well, I was staring out the window thinking about those heels the woman in the dress was wearing. If she was barefoot or in any other kind of shoe, I probably wouldn't have even given her a second look but damnit if those heels didn't turn me on. I just needed to make it home so I could take care of myself.
Arriving home, I was the first out of the car and first into the house. As unbelievably horny as I was, I was stripping off my clothes on the way to my bedroom. Locking the door behind me, I opened up my laptop and pulled up my favorite porno. Naked and sitting in my chair, I pumped some lotion into my hand and started jerking my cock while watching two women take turns sucking a guys cock. One girl was a teacher, the other a student. The guy was also a teacher. Both women had on high heels, but one had black stockings on as well. I wasn't surprised when I blew my load halfway through the blowjob scene. I figured now was a good time for a shower, especially since my cock and hand were quite messy.
After a nice warm shower, I was laying on my bed, naked, with the fan going full speed. The cool air blowing over my body felt so good. Thoughts of what I saw in the restaurant creeped into my head so I closed my eyes and let my mind wander. It didn't take long for me to fall into a pretty deep sleep and drift off into Lala Land. The woman in the restaurant was small chested and too skinny for my liking so with a little imagination, my perverted mind decided to replace her with someone else.
Naturally, the first thing I pictured was those heels, damn they were sexy. Then a set of legs seemed to materialize. They were a bit thicker but toned and slightly tanned. Next body part was the ass and thighs, plump booty with average size thighs, just enough. Then came the back side, not too skinny but not fat, with nice shoulders and arms. Moving to the front, a set of tits that would make some women jealous, had to be 42D sized tits easily. Finally, the head started to materialize, making this person around 5 foot 4 inches. As the hair came into view, something about the person seemed very familiar. When the face of the mystery girl turned to face me, my cock reacted in a way I never thought it would.
In this weird dream, I was now standing face to face with my sister wearing the same heels the woman in the restaurant had on. She was naked and smiling at me and my cock felt like it was going to explode. Then she spoke, but her lips didn't move. Suddenly, I began to shake and then I woke up. Before me was my sister, wearing only a loose fitting T-shirt and pale pink panties. Looking at her, I noticed she was blushing and had this silly smile on her face. "What's wrong with you?" I asked.
"Well, I knocked on your door and asked if you were awake and when you didn't answer me I assumed you were sleeping so I peeked in and that's when I heard you say my name, but you were naked and well...lets just say not all of you was asleep." She said, while trying not to giggle.
"What?" I said, still trying to wake up.
"I don't know what you were dreaming about, but you said my name in your sleep and your dick is rock hard right now." Allison explained while staring at my crotch.
Looking down at myself, I notice that my cock is quite hard and standing at attention. "Oh. Sorry, took a shower and fell asleep.
"I...uh...see that. Are you going to cover it up?" She asked, with her eyes still looking at it.
"Hmm. No, I don't think I will. If you don't like what you see, you can leave.." I said.
"Oh, well maybe I do, maybe I don't." She said. As she stood there, she started doing that lip biting thing, indicating she was definitely thinking about something.
"Well, since you're still standing there looking at it, you must like what you see." I said with a smirk.
