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Some men would think a cock that is 8″ long and 2″ thick when soft and almost 11″ long and 3″ thick when hard is a blessing. Now, in my early 50s, I can say it’s probably given me an equal amount of embarrassment. I’m currently on a work assignment that is testing the limits of my ability to resist reliving the old days. I’ve been working with a 26 year old sweetheart named Anna for the last two months and my struggle to stay faithful to my wife has been grueling working alongside her.
I would have initially described Anna as carefree, maybe even oblivious, until the last couple of weeks. From our daily interactions, I gather that Anna doesn’t attract a lot of attention from the boys her age. I guess that’s because she’s a redhead, 5’10” tall and a bit larger girl, maybe 30 lbs overweight with large breasts. Her height might have been a detractor but, being 6’2″, I never minded taller women.
Personally, I would say she’s attractive but hides it under a bit of a frumpy appearance. Anna’s usual outfits consist of baggy sweaters and shirts, elastic band waist gathered skirts and tights along with cute flats. Nothing I would describe as flattering but I’m not a young man without imagination. I could clearly see there was a sexy woman hiding underneath dull covering.
Her large breasts and wider hips made her waist look small. You’ll have to excuse me, my mind was just wandering. It took a revelation from the past to finally understand what drew me to Anna. My wife, Karen, is petite at only 5’3″ and 115lbs, nothing at all like Anna.
Anna reminded me of someone from my past and that is the crossroads of where I believe Anna and I finally connected. I need to go back to my teen years when I was struggling with being embarrassed about my large cock. The fashion trends of the 80s made staying modest with my cock nearly impossible and I was pretty withdrawn because of that. I couldn’t wear the loose “dolphin style” shorts for fear my cock would hang out past the hem, so I wore the almost knee length shorts. Then I discovered there was almost nothing I could wear to hide my prominent bulge or the snake running down the inside of my thigh.
By the age of 18, I had a healthy masturbation schedule back then and, having two sisters with cute friends didn’t help. I have a younger (Katie) and an older sister (Susan) and I am only a year apart from either. One of my favorite activities then occurred when my older sister had sleepovers. I knew I’d have no chance with any bursa escort bayan of her friends and I would have given anything to be able to jerk off while smelling and tasting their panties. This is how my foot and shoe fetish began.
Even though I desperately wanted my sister’s friend’s panties, the only articles of clothing available to me were a variety of heels and flats at the door. I don’t know what possessed me but, one Saturday morning I was up before everyone else in the house and found myself standing over a pile of shoes. I picked on well worn flat up, size 7, and smelled it deeply. I was hooked. My cock went to full hard….a glorious 11″ poking right out of my boxer shorts.
In that moment, I grabbed the mate to the flat I was now devouring and slipped it over the head of my aching cock. My cock head barely fit into the toe area, without ramming it hard, stretching the shoe. The feeling of insole against my sensitive cock and the heel cup grinding against the thick vein on the bottom of my cock started an orgasm boiling inside me. I quickly pulled it off my cock before I dropped an enormous load into it. I set the shoes down, went to the laundry room and grabbed a pair of my sister’s dirty ankle socks and a pair of dirty panties and returned to my room. That enormous load ended up in one of the cute white socks.
I was always using my sister’s or mother’s dirty socks, pantyhose or panties to jerk off with but something different happened today. As I jerked off into one of the ankle socks, I starting sniffing the dirty panties and the other sock. I even tasted the crusted pussy juice from the crotch of the panties and turned the sock inside out to get a taste of the sweat; not sure or caring who they belonged to in that moment of passion. I had never done that before and it turned out that I felt deeply ashamed that these were my mom’s panties and Katie’s ankle socks. Despite my shame, I dropped the biggest load of my entire life into my sister’s dirty sock. I returned the panties and socks to the laundry and went about my day.
Saturday was a struggle for me with Susan’s three friends hanging out in the house, watching TV, playing games, etc. in their short shorts and belly shirts. I found any excuse I could to be in the room with them, watching them and hoping for a glimpse of a boob or pussy. Susan’s friends, Mary and Lori-Jane, seemed to be more guarded, sensing that their friend’s little brother was perving on bursa escort sitesi them. Kelly, however, didn’t seem to care at all. i caught several glimpses of her pussy and the underside of her boobs. I was wearing a pair of loose shorts and a t-shirt and, it wasn’t until I was trapped in the living room that I realized I had made a mistake. Upon the insistence of Kelly, telling my sister she thought I was cute, I was allowed to hang out with them to watch a movie. As it turned, out it was not a mistake at all.
The movie was boring and the girls decided to play Monopoly instead. I went to excuse myself when Kelly intervened and invited me to stay. The other girls sighed and voiced their disapproval. My sister just said “as long as you behave yourself”. I thanked Kelly and we all sat around the coffee table and set up the game. As a young man, I found Mary and Lori-Jane to be total babes, petite and tight bodies. To be brutally honest, I didn’t give Kelly a second look until that day. Kelly’s a redhead, about 5’11” tall and a bit larger girl, maybe 20 lbs overweight with large breasts. I also noticed she had big feet, probably size 10, but her long, slender toes with nails painted a deep crimson drew my attention. My sister and Lori Jane sat on the couch while Mary and Kelly sat at either end of the table, leaving the middle, opposite the couch for me to sit.
As we began playing, I couldn’t help myself stealing glances of Kelly’s long legs and beautiful feet. I think she knew this and was putting on a little show, while trying to not to let the others know. I also had a good view of Mary’s cute little feet with ankle socks on. My cock was starting to respond and there was nothing I could do to stop it. I felt my hardening cock breach the hem of my shorts down my right leg…in plain view for Kelly were she to shifted slightly towards me.
When it was Kelly’s turn again, she pushed up to reach her player piece on the board and that’s when I knew she had seen my cock hanging out. She gasped slightly and the other girls asked what’s wrong. Kelly quickly replied that she didn’t like the roll she just made, then diverted her eyes right to my straining cock and then smiled at me. She had definitely seen my large cock pulsing for her. A few moments later, I felt her bare foot against my leg. I was sitting Indian style, so I unfolded my left leg and spread it towards Kelly, hoping, no desperately wanting, her to reach out for my cock with her bare foot. I had calculated that correctly as I soon felt Kelly’s beautiful toes touch my aching monster. She held her foot there as my cock throbbed its approval.
Lori Jane then announced a bathroom break but the girls objected, citing concerns that I’d cheat while they were away. Kelly volunteered to hang back and keep an eye on me. As the girls began to get up, Kelly withdrew her foot from my throbbing cock and slid a throw pillow my way just in time to hide my massive boner. Once we both heard the girls upstairs, Kelly looked me right in the eyes and said something I will never forget, “Mikey, your sister said you had a big cock but I had no idea it was the size of a baseball bat”. This was my moment of truth and I mustered up the courage to ask her if she liked it. Kelly just moaned, slid over beside me and grabbed my cock. She smiled when she told me that she couldn’t even get her hand around it. Suddenly, we heard one of the girls racing down the stairs and she quickly released my cock and slid back over to her spot. During the next couple of hours we played, Kelly took every chance she could to touch my cock with her feet or her hands. I wanted to slide all 11″ of my cock into Kelly so badly but it would be a few months before that opportunity presented itself.
That night, as I lay in bed thinking about Kelly touching my cock, I needed to release an orgasm badly. This was a whole weekend sleepover, so I waited until the giggling stopped in my sister’s room before I found myself standing over the pile of shoes. Instead of going for Lori Jane flats or Mary’s heels in size 7, I picked up Kelly’s size 10 flats. My cock was hard as a rock as I took Kelly’s shoes back to my room. After I had thoroughly smelled and licked her shoes, I spent the entire night fucking Kelly’s flats and, being size 10, they accommodated my giant cock almost perfectly. If I pushed in real hard, I could stretch her shoe enough to allow my balls to sit in the heel cup. I managed to drop two loads in each of her shoes and, in my teen brain, it made sense to me to not clean up after myself, reasoning that Kelly would like this. I returned Kelly’s shoes to the mat around 6:30am, hoping the girls would sleep in late.
The girls did sleep in until noon and, right before Kelly was leaving, I checked her shoes and noticed they were still fairly damp with my cum. Kelly was the first to leave and I made of point of saying goodbye to her as she slipped her flats onto her bare feet. She had to have known they were damp but she just smiled at me and whispered “you’ve been naughty” as she grabbed my cock through my shorts.
As I entered my senior year, I discovered that having a large cock could work to my advantage….
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