High Heel Fetish

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.

"Oh for fucks sake, it's a beautiful cock, but how big is it? I mean, I'm just curious, you know, asking for a friend." She asked with a slight giggle.

"Last time I measured, about 8 inches, nothing to get excited about. And sis, you don't have any friends that are interested in me so no need to play games." I responded as I watched her eyes widen a bit more.

"Really? You're not fucking with me are you? Eight inches, that's like, almost a pornstar level cock. You're not doing porn are you?" She gave me a weird look when she asked that question.

"Porn? Am I doing porn? Come on sis, if I can barely talk to your girlfriends, how do you think I could manage doing porn." I asked while laughing

"Hey, I was just wondering. No need to get all defensive. But seriously, you've got a pretty good looking cock bro. I mean I wouldn't mind seeing that thing in action sometime." She said suddenly, then turned and walked out of my room.

Shocked at what my sister had just admitted to me, I didn't know whether to be grossed out or turned on. Seeing how it was already after 10 pm, I decided to sleep on it and see what the next day would bring.

*****NEXT DAY*****

Waking up to the awfully loud lawnmower going past my window was not the way I wanted to wake up, but nevertheless, I was now awake. I laid in bed for a few minutes longer, thinking about my dream and what happened. Was it all just a dream or did that 2nd part really happen? Shaking it off I got up and dressed myself for the day. With a quick check of the weather, it was going to be a tshirt and shorts kinda day. I then made my way down the hall and as I was passing Allison's room, I noticed her door was open so naturally I peeked inside. Her bed was made and the room cleaned up, not too surprising, so to the kitchen I went.

Talk about a way to kick off a Sunday morning, as I walked into the kitchen I caught a glimpse of my Mom bent over pulling something from the oven. I had never really stopped and admired my mother but this morning, I took the time to stand back and really take in her looks. For a 47 year old woman with 2 kids, she looked damn good in that white floral sundress and pink thong. As I stood there, I could feel my cock start to stiffen up and all sorts of naughty thoughts flooded my brain.

"Goodmorning Mom." I said as I walked over to the counter next to her. Her perfume filled my nostrils, further causing my dick to stiffen.

"Good Morning sweetheart. Did you sleep well?" Mom said as she placed the biscuits on the stove.

"Slept like a baby." I responded. From the side view I had of her, her tits looked plentiful, but not quite as big as Allison's. I wonder if Mom was jealous that her daughter ended up with bigger tits.

"Awh good, I like it when my kids sleep good." She said. Just then, Allison walked into the kitchen wearing her normal attire, t-shirt and short shorts.

"Mornin' fam." She said in a rather giddy way. She was unusually chipper this morning.

"Hi honey. Did you sleep like a baby too?" Mom asked

"Oh yeah, I feel amazing. Hey Mom, me and Michelle are going to the mall this afternoon, shoe shopping I think." Allison said as she looked right at me and smiled. I nearly choked on my orange juice when she said that.

I didn't know what she was getting at or planning but the swelling body part in my pants may have had an idea. The rest of the morning went by quietly as Dad had finished cutting the grass and Allison stayed in her room doing whatever 20 year old women do. After breakfast dishes were cleaned up and the kitchen was back to normal, Mom had nothing else to do so she ended up joining Allison and Michelle on their trip to the mall. I on the other hand, took advantage of the fact the family TV, a 65 inch 4K Samsung, was not being used and dragged my Xbox One X out of my room and hooked it up. Within a few minutes, I was connected and playing Call of Duty Warzone with a few buddies online.

*********************

"So girls, what store are we hitting first?" Mom asked as the 3 women entered the mall.

Michelle spoke up first. "Well I don't know about you ladies but this gal needs some new lingerie. Chris loves it when I surprise him with new sexy stuff." She said.

"I'm just looking for some new shoes. What about you Mom?" Allison asked

"Hmm, lingerie sounds good but new shoes do too..." Mom pondered her decision while they walked further into the mall.

"Here's the shoe store, Michelle, I'll call you once I've checked out and we can meet back up." Allison said to Michelle.

"Ok, shoes it is then." Mom said. As Michelle headed off further into the mall, Allison and Mom entered the shoe store. "So what kind of shoes are you looking for dear?"

"High heels." Allison said with a smirk. As she wandered up and down the aisles, Mom couldn't help but ask questions.

"What's the occasion? You've never really been the type of girl to rock a pair of heels. Is there someone you're trying to impress?" Mom asked as she examined a set of 4 inch heels.

"Something like that. I found out he's got a thing for women in heels and I figured why not. So I'm looking for something that'll get his attention." She admitted

"I see. Well then let's find something that screams sex appeal." Mom said as she moved on to the next aisle.

"What about you Mom? Do you own any heels? Allison asked while she tried on a pair of red heels.

"One pair. The pair I wore for your father on the first night of our honeymoon. I loved them. I felt sexy as ever in them. But, your father apparently didn't care as much about them because before we really got into it, he took them off. After that, I never bought another pair. No sense in paying money for something that doesn't get your man all worked up." Mom explained as she too tried on a pair.

"Well, how about buying a pair just because. You never know when a good set of Fuck Me heels will come in handy." Allison said with a wink.

"You're absolutely correct love. Alright, I'll buy some. I may need some help though." Mom said with a smile.

"I think I know just the kind of heels that you'll like." Allison said with a devilish grin.

**********************

About an hour later, Dad's phone rang and a few minutes later, he's heading out the door with his briefcase and suit jacket. Dad was some sort of accountant for a couple different companies so it was normal for him to be called away at a moments notice. I shrugged my shoulders and got back to gaming. With my headset on and volume up, I was oblivious to anything around me. It was nice to be able to play without anyone bugging me.

I had no idea how long Mom and Allison had been home when I glanced out the window and saw Mom's car in the driveway. Taking my headset off, I could hear movement and voices down the hallway. Curious, I got up and went to see what was going on. I heard Mom and Allison laughing from Mom's room so I knocked on the door.

"Hey Mom." I said.

"Oh hey baby, come on in." Mom replied. I opened the door and went on in.

"What are y'all up too?" I asked. Looking around, I noticed some shoe boxes on the bed.

"We were just talking about a guy who Allison is interested in. So much so that she went out and bought some high heels to get his attention. She even managed to convince me to buy a pair seeing how I hadn't bought any since I married your father." Mom said. I stole a glance at Allison and she had this evil but sexy as fuck grin on her face.

"Oh yeah? Cool." I responded with, pretending to not be that interested.

"I have an idea!" Mom said with excitement. "Why don't we let your brother, since he is a guy after all, give us his opinion." She explained.

"Oh I don't know. His tastes might be different." Allison argued.

"Only one way to find out." Mom said as she slipped off her flats and opened up her box, Allison soon followed Mom's lead and began to open hers.

I couldn't believe what was happening. Not only was my sexy older sister about to show off her new high heels for me, but my incredibly hot MILF of a mom was about to join in the fun. My cock was already starting to swell when Mom pulled out her new shoes.

"So whatcha think sweetie? Did your old Mom do alright?" Mom asked as she held up her heels. They were totally those slutty Fuck Me kind of heels and I loved it.

"Oh for sure Mom. Those look great. I'm sure you'll love wearing them." I said. Allison showed off her next.

"What about mine bro? I saw these and thought they were absolutely perfect. I mean look at them. How could he not be interested in me when he sees me with these on." Allison said, teasing me even more with her sexy smile.

"I'd say there's no way he wouldn't love what he sees. Why don't you both put them on so I can see them on you." I asked nervously.

"Why not." Mom responded. She reached down and slipped off her flats revealing her nicely manicured toes. Stepping into the glossy black 5 inch platform heels, her red painted toes made great contrast with the peeptoe in the front. My cock pulsed so hard I almost reached down and grabbed myself. I had no idea how I was going to keep the bulge in my pants hidden.

"Damn Mom! Allison exclaimed. "You look hot! You'll make cocks hard everywhere you go wearing those."

Mom blushed. "Oh thanks honey." Then she looked at me. "Well, how about now?" She asked.

"Uh...yup. Definitely...." I said.

"My turn." Allison interjected before I could say anything else, which got Mom's attention off of me.

I looked over at Allison and my jaw hit the floor. I didn't really notice when she was holding them but once they were on her feet, it hit me. They were the same heels the girl in the restaurant had on, black with red bottoms. I shuddered with pleasure.

"Are you okay sweetheart?" Mom asked.

"Oh yeah just hard..err..I mean fine." I said

"Hard?" She said with a confused look. Then she glanced down at my crotch. "Holy fuck baby! Sweetie...I mean damn." Mom said.

"Pretty big huh Mom?" Allison asked as she stood next to Mom looking at the bulge in my pants.

"I'd say massive. That must be uncomfortable honey. Here, let mommy help." She said as she dropped to her knees and unzipped my pants. Reaching in, she wrapped her hand around my cock while it was still covered by my boxers. "Wow baby, you are definitely bigger than your father, that's for sure."

Fishing my cock out of my boxers, she pulled it out and her eyes went wide. Watching porn, I've seen much larger dicks but Mom's reaction to seeing my cock definitely made me full of pride and confidence.

"Damn little brother, I mean you're very much not little down there. Looks even bigger than the first time I saw it." Allison admitted.

"First time? Explain yourself young lady!" Mom responded swiftly.