Aunt’s Stockings & Mom’s Pantyhose

Summary: A lucky guy gets his Mom and Aunt as Christmas presents.

Aunt’s Stockings & Mom’s Pantyhose

0. Prologue

A lot of crazy things all occurred over a few weeks that shifted my unhealthy sexual preoccupation with my Mother and Aunt from fantasy to reality.

1. The first revelation…Oedipus Complex

The first happened in early November.

I was in my freshman college psychology class when all my unhealthy obsessions, well at least the biggest one, suddenly made sense. My professor discussed Sigmund Freud’s Oedipus complex which he believed was a universal psychological phenomenon that all boys fantasize about having sex with their mothers.

There was utter silence and I wondered instantly if it was because they were all thinking the same thing I was. ‘Thank God’. Although I had a steady and very hot girlfriend, who liked giving head and fucked me regularly, every time I masturbated it was not to my girlfriend Kim, but rather to my mother Annabelle that I thought about.

My professor continued to discuss how the Oedipus complex was a theory that deep inside every boy is the desire to sexually possess their mother. These inappropriate thoughts are held deep inside the boys’ subconscious and never released, therefore never being dealt with emotionally. In extreme cases, the son wants to murder their father and replace him as the man of the house.

I was floored. I had fantasized about having sex with my mother since puberty and always felt guilty afterwards. I mean when I was horny my fantasies always included my mother being my sexual submissive and obeying my every order, the way I assumed she did my father in the bedroom.

My fantasies were often different, but they always included my Mom in pantyhose or stockings, obeying my every sexual whim. Sometimes I imagined forcing her to suck my cock and shooting my cum down her throat; other times I imagine being woken up by Mom’s beautiful lips; other times I fantasized taking her in the back of the car while Aunt Cassie, Mom’s younger sister, drove in the front seat oblivious to Mom riding her son’s cock. Other times I created crazy tales full of risk like eating Mom’s pussy under her desk at school while she graded papers while students were in her class unaware of what was occurring under her desk. However, mostly I just fantasized having Mom suck and fuck me. Yet, as soon as I would cum, an overwhelming guilt hit me as I couldn’t believe I would fantasize committing incest and treating my mother so inappropriately and with such disrespect.

Yet, my biggest sexual kink, besides the fact that I wanted to fuck my Mom, was I was obsessed with stocking-clad feet, particularly toes in nylon. This kink too is my Mom’s fault. Being a teacher, every since I can remember she always dressed in pantyhose and even after work she would stay in her skirt or dress and pantyhose, walking around the house in her nylon-clad feet.

Besides the kinky dominant persona fantasies that dominated my every thought, I had other more sensual fantasies including: giving Mom a full body massage while she wore her pantyhose, eating her cunt through her sheer pantyhose (when she was of course sans panties) and getting a foot job from her delicious stocking-clad feet.

Over the next couple weeks I couldn’t help but literally drool over Mom; I couldn’t resist staring at her nylon-clad feet; I couldn’t stop wondering if her cunt was shaved, trimmed or hairy; I couldn’t stop imagining making her my submissive plaything…after all, it wasn’t my fault I had a complex.

2. A bit of more history

Before I get to carried away with the motivation behind my obsession with having sex with my mother, I should tell you a bit about myself and our family history which ironically will play a huge role in the crazy story I am about to tell.

My name is Christian (which is ironic considering the story I am about to tell, not to mention the shunning by our family that my mother received for having a child out of wedlock). I am about as average as they come. I am 5’9, 190 pounds, have black hair and brown eyes. I compensate for my average looks by being humorous, a great listener and quite smart. I am a nerd or geek or whatever you call students who care about their marks, I can quote Star Wars verbatim (the original three not the blasphemy that was the prequels) and I still play MindCraft.

My Mom, Annabelle, had me when she was sixteen, (yep I’m a bastard and an oops) and we since then have been shunned by her super religious family. The only family she still talks to is her younger sister, Cassie; who has been shunned as well for staying in contact with Mom. Mom was shunned because she wanted to keep me; and being from a puritanical home, this wasn’t exactly a decision that left her with many options. At 35, Mom is still a complete knock out; 34DD breasts (I checked her bra size), a slim waist that flares just perfectly into a set of wide hips and a tight heart-shaped ass. She’s got green eyes and the prettiest smile I’ve ever seen. Her ravenous look is completed by natural red hair that flows just past her shoulders. I wasn’t the only one jerking off to my Mom, my friends called her a MILF as far back as I can remember. As already mentioned, she also enhances her beauty with a keen sense of fashion: blouses that showcase her large breasts without looking inappropriate; skirts long enough to be school appropriate but short enough to distract every guy or lesbian in her class; at work, always three inch heels that added to her sexy allure; lastly, she always wore pantyhose, in a variety of colors (mocha, tan, black, blue, red and even white), that always perfectly complimented her outfit.

Aunt Cassie, although four years younger, is a spitting image of Mom, the same green eyes, the same large breasts, same great body, although she has black as night hair. Although Mom was my number one stroke fantasy, Aunt Cassie was a close second. She too almost always wore pantyhose even under her jeans which I thought was super hot.

The two were so similar that they even took the same career route, both becoming teachers. Mommy, finishing high school by getting her GED when she was twenty-one finally got her teacher degree when she was twenty-six. Mom teaches high school English and is a great teacher. Aunt Cassie teaches kindergarten.

As I grew up, my Mom and aunt would always tell me how much I looked like my father. And it’s true; I’ve seen a few photos of him and even met him when I was 14. He bailed on my Mom when she found out she was pregnant (he’d just graduated from high school). I don’t mind though, he’s an asshole and my Mom deserves better.

At my graduation, my fantasies changed to incest threesomes when I got a double hug-their tits squishing against me. After that, my late night stroke sessions often included Mom and my aunt pleasuring me and each other. It never occurred to me that one day these fantasies could possibly become a reality.

3. The second revelation…Dad’s fetish photos

I was in the garage getting rid of boxes of crap Mom had kept for years when I found the photos. They were in a box of old high school memories including: yearbooks, track ribbons, cheerleader pompoms, pantyhose (dark coloured) and a cheerleader’s outfit that I imagined Mom could still pull off today. My naughty mind instantly went to her in such an outfit seducing me.

Also, at the bottom of the box was a small envelope with a few photos of a few different girls, all in pantyhose, all without shoes, all looking fucking hot.

My cock already stiff from the cheerleading outfit, these pictures, none of them overly naughty yet the nylon legs were sexy as hell.

I flipped through the pictures in awe of the extensive collection.

Were these Dad’s photos?

Mom’s?

It would be weird for Mom to have a collection of pictures that were of women in pantyhose. She had never given any remote hints that she was into women, although in all fairness she had given very little evidence that she was into men either…having not dated one guy that I could remember.

Yet, it would be weird for this collection of photos to be in a collection of Mom’s high school things as well.

In the end it didn’t matter whose they were, they were super hot and had me ridiculously horny. I picked my favorites and was about to sit down and jerk off when I saw one of Mom when she was in her early twenties. Ironically, she looked almost exactly the same then as she does now. Same adorable smile, same exotic eyes and the same perfect legs.

I pulled out my cock, stared at the picture of Mom as an eighteen year old teenager and began stroking. I imagined her as a cheerleader, I imagined her in the eighties with her big hair, I imagined her on her knees crawling over to me and taking my cock in her mouth. I imagined her giving me a foot job in her silky nylon feet while telling me how much she wanted me to cum all over them.

With such naughty thoughts it didn’t take me long to get really going and I shot my load all over the photo of my mother, giving her the long fantasized facial although not quite the way I had envisioned.

I stared at the photo of my Mom, covered in my white goo, and wondered if there was any way to make such a fantasy a reality. At the time it was just a silly adolescent fantasy, yet a domino of revelations, coincidences and long held secrets would soon change the odds of making that fantasy a reality.

4. The third revelation…Mom knows my fetish

Mom and I were at Hooters (yep Mom took me to Hooters) for supper (they do have amazing wings jsut for the record) it was then that I learned Mom knew one of my secrets.

I was checking out a hot brunette waitress, her mocha pantyhose legs seeming to literally shimmer as she moved (Hooter girl pantyhose really are the hottest color in the universe. They are shiny and sexy…and I imagined, though I had never touched them silky) when Mom joked, “You are just like your father.”

“So I have been told,” I sighed, hating getting compared to him.

“No, no, no, not in looks, although you definitely are sexy like him, but you have the same strange fetish,” Mom said.

I couldn’t get past the reality that Mom had called me sexy, even as I adjusted my stiff cock under the table. “What are you talking about?” I asked, as I glanced again at the waitress’s shiny legs…literally unable to resist the magnetic pull of the nylon.

“You are a legs man,” she said.

I shrugged thinking the same words I said, “Who isn’t?”

“99 percent of the male population,” she laughed. “At least that is my experience.”

“Really?” I asked, thinking there was nothing hotter than a woman in nylon.

“Are you really that obtuse,” Mom joked. “Do you have any idea how many men stare at these?” She questioned pointing to her own huge breasts as well as waving her hands around the restaurant.

“Oh,” I said, realizing she was talking about breasts, particularly her breasts which had me looking directly at them inside her sweater, to just see the canyon that hinted at so much more.

“We are at a restaurant called Hooters,” Mom said. “Is there a restaurant called ‘Legs’?”

“There should be,” I said. “Actually it’s a great entrepreneurial idea.”

“Or one called Pantyhose,” Mom smiled.

“W-w-what?” I stammered.

“Oh honey, you don’t remotely conceal your nylon fetish,” Mom laughed.

“I don’t?” I asked, overwhelmed by Mom’s sudden frankness.

“Your father had the exact same fetish,” Mom explained. “He particularly had a fetish for toes in nylons.” To make the point, she slipped out of her heels and wiggled her nylon-clad red toes.

“I-I-I don’t,” I lied, the stammering betraying my lie.

“It’s okay, honey,” Mom said, sadly slipping her feet back into her heels. “Everyone has a few quirky kinks.”

Before I even had time to think what I was saying, I blurted out, dying to know, “What’s yours?”

Just then the waitress arrived with our wings and Mom expertly shifted our conversation to more conservative normal topics like college.

My cock never shrunk, my head replaying the strange conversation over and over and over again throughout the meal even as I continued to have a normal conversation with Mom.

That night, while Mom was in the shower (she always has her showers in the evening), I snuck into her room, grabbed a pair of Mom’s pantyhose and hurried to my room. I had never done this before, but after our surreal conversation I wondered what it would feel like to masturbate in pantyhose. Originally, I planned to just put the pantyhose on my hand and jerk myself off, yet before I knew it I was putting them on. Although way more difficult than one would think to get on, I eventually got the pantyhose up my legs (remembering from watching online porn that I needed to scrunch the pantyhose over the toes and slowly slide it up my leg). Once on, my stiff cock was framed in the nylon, I began rubbing my legs, ass and cock. I couldn’t resist touching myself, thinking if I was a woman I wouldn’t be able to resist caressing myself in public.

Wearing pantyhose seemed kind of gay, yet the feeling was so amazing I didn’t really care. I stared at my feet in the pantyhose and was thankful when I wasn’t turned on by that.

I lay on my bed, closed my eyes and rubbed my cock slowly as I imagined Mom in a Hooters outfit, minus the hideous slouch socks they wear, flirting with me. It didn’t take long to get my balls boiling and I came in the pantyhose in less than two minutes. Hearing a noise, I looked up to my door which I realized was open a crack. I gasped, mortified at the thought that Mom could have seen me. I quickly tugged the pantyhose off me and peeked out the door. The hallway was empty and the bathroom door was open which meant Mom walked past my room. I closed my door, got dressed and fretted that Mom saw me in her pantyhose.

I waited a few minutes until I heard the television on downstairs before I quickly returned to her room and put her pantyhose back, not thinking of the incriminating white stain I would leave on them once my cum dried. I went back downstairs acting casual and Mom showed no signs of acting different or peculiar, which she probably would if she had seen me in my compromising cross dressing situation. A huge worry off my shoulders I made myself a snack and watched Person of Interest with her like we always did on Tuesdays.

5. The forth revelation…They want to fuck me

On Friday, three days later, I came home late to see Mom and my aunt drinking having just got back themselves from some teacher Christmas party, both past tipsy.

Aunt Cassie really looked ridiculously hot in a one piece black dress that had a zipper down the middle. Leaning against the kitchen counter, wine in hand, her legs in tan nylons, my cock stiffened in my pants and I already knew what my stroke fantasy would be tonight.

I chatted with them a few minutes, quite drunk myself, trying to not stare too much at Aunt Cassie’s legs, before heading up to bed. After getting ready to crash, my mouth was super dry so I headed back downstairs partly to quench my thirst and partly to get another look at Aunt Cassie and Mom.

I was about to enter the kitchen when I heard Mom say, “I gave him hints on Tuesday.”

I froze. Was she talking about me? What hints was she referring to?

I listened intently out of view.

“You can’t be subtle with men. You have to literally tell them,” Aunt Cassie said, laughing.

“I am not sure I am able to tell my son that I want to fuck him,” Mom responded.

My mouth dropped open as I heard the words I had fantasized about my whole life and yet never in a million, trillion, years thought I would ever hear…for real.

“And be his submissive slut,” Aunt Cassie added.

“Well that goes without saying,” Mom playfully quipped back.

“So now what?” Aunt Cassie asked.

“Well I know our conversation at Hooters turned him on as he stammered like a horny fool and then I caught him masturbating while wearing my pantyhose,” Mom continued, confirming my earlier worry.

“Mmmmmm,” Aunt Cassie moaned, instantly making my already stiff cock flinch as I imagined seeing her face make such a sexy noise. “Does he know you saw him?”

“No, I don’t think so,” Mom answered.

“You should have just walked in his room, crawled into his bed, straddled his cock and rode him like a cowboy,” Aunt Cassie said, as I pulled out my cock that was in desperate need of release.

“God, I wish I would have,” Mom said, before adding, “I fucking need to get laid soon or my cunt will shrivel up and die.”

“Go seduce him now,” Aunt Cassie suggested, my eyes going big.

“I can’t, I need him to make the first move. I couldn’t handle it if he rejected me and thought his mother was some sick dirty slut,” Mom said, sounding insecure like my last girlfriend.

“Based on his constant drool over you, I don’t think he will reject you,” Aunt Cassie correctly predicted.

“Even so,” Mom said. After a lengthy pause she added, “I did get to kinda taste his cum.”

“Fuck off,” Aunt Cassie gasped.

“The pantyhose he jerked off in were back in my drawer I noticed at bedtime and well….”

“You sucked his cum out of your pantyhose, why you dirty little slut,” Aunt Cassie said, finishing Mom’s sentence.

“Isn’t that twisted,” Mom said, her tone both mortified and somehow playfully naughty.

“Twisted, yes; fucking hot, for sure,” Aunt Cassie said.

“I’ve got to stop this,” Mom said.

“What? Fantasizing about fucking your sexy son?”

“Yes, it’s unhealthy.”

“So is fast food, but you still eat it again and again,” Aunt Cassie said.

“Not sure going to Kentucky Fried Chicken too much and obsessing about my son making me his dirty whore is the same thing.”

“Well you are finger lickin’ good and you love choking on a bone,” Aunt Cassie crudely joked.

“You are so fucked up,” Mom said, even as she laughed.

“Two bottles of wine will do that,” Aunt Cassie said.

“Maybe when I sober up these uncontrollable sexual urges will go away,” Mom said.

“Unlikely, we have been having this discussion since his eighteenth birthday,” Aunt Cassie revealed.

“Well, I did think waking him up with a blow job would have been a great birthday present,” Mom replied.

“Do you know what you are giving him for Christmas?” Aunt Cassie asked.

“No idea,” Mom replied.

“Well maybe you give yourself to him for Christmas,” Aunt Cassie suggested.

“You are scandalous,” Mom playfully laughed.

“So is this,” Aunt Cassie replied sultrily, snapping her fingers.

“Not here, what if Christian comes down,” Mom protested.

See Part 2 here!