Well Endowed; A detailed sexual history of how I came to realize [M]y cock is huge.

I didn’t have the slightest clue or idea that I was well endowed until age 28. I have had a fair amount of partners, many of which dropped hints or made it abundantly clear, but thanks to porn and associated conditioning, it took me a very long time to finally recognize, understand and overcome a serious insecurity that my cock isn’t small, isn’t average, but actually is unusually large. Below is a brief account of my sexual history and all of the “hints” I received (and flew well over my head) over the years, leading to eventually overcoming this insecurity. Fair warning that this will read as a humble-brag, and to be honest, it more-or-less is exactly that. I’m writing this with clear eyes in hindsight. This is almost even therapeutic for me as at the time I was going through literally all of these experiences, I was seriously and shamefully in denial that I was large, assumed I was small and inadequate (thanks to porn’s misconceptions and a few select partners), thought every girl was just being nice & lying when complimenting me, and was constantly trying every thing possible sexually to be bigger and better to live up to the pornographic expectations from the clips I watched through my adolescence. I hope you either enjoy reading purely as a sexual experience or it helps you to overcome your own insecurity and that your cock is perfect, no matter what may you think or feel otherwise.

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Getting this out of the way early – I don’t have any need or desire to measure my cock so you’ll need to draw your own conclusions as you continue reading.

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I had an insane sexual connection with my first ever girlfriend. We lost our virginity to each other and I then railed into her every chance I got… our chemistry was combustable. She would cum at least 3 times every session, sometimes 5 or 6. Certain positions made her squirt like a fire hose, and she would aggressively gush her warm, delicious fluids against my lower torso and absolutely soak the sheets & towels on a regular basis. Like I said, I lost my virginity to her and was with her for several years so this was the norm for me. She lost her virginity to me as well, so she had no way to understand that my size was unusual, as she had no other comparisons (at the time, more on this later). Didn’t at any point feel I was special or well endowed, just assumed that this is how sex was …and it was fucking awesome, I was hooked for life. I became, and still am, obsessed with making my partner cum as much and as hard as possible. Tasting the orgasmic juices, feeling a pussy or ass tighten around my cock, watching and hearing my partners face and body light up with pleasure… I crave it constantly.

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We eventually went our separate ways and broke up. it was impossible to match that chemistry with anybody else. But little hints at my unusual size (that I did not recognize at the time) would subtly arise with other partners through the next few years. Early on, I slept with a girl who (unbeknownst to me) was cheating on her boyfriend at the time. She whimpered as I slowly pushed every inch of me into her whispered under her breath (almost to herself) “it’s so much bigger than Ben’s.” I didn’t put two and two together at the time and went about assuming I was below average or average at best. My next partner would often comment that I “broke” her pussy after we fucked. A later partner would moan, almost in pain, “so.. big… so… big” as I pounded into her. Another, an Australian woman who I met at a bar, choked on me at her apartment later that night and complimented my cock, with her delicious accent, as being “fucking gorgeous.” All of this and I’m still clueless, completely brainwashed from porn conditioning. At one point, when I was 19, I met and hooked up with a couple in their early 30s. The husband would brag that his wife could “deepthroat any cock.” I told him I had yet to have anybody swallow me whole, so they were excited to show me a new sensation of being fully engulfed by an eager throat. The first time we had sex, she swallowed his entire cock, then made an attempt at mine. She could only get about halfway down before tapping out. With great effort she made it about 3/4 the way. He was a little embarrassed that she couldn’t live up to the hype, but their shame quickly dissolved after we both mounted and absolutely pounded into her holes (I was lucky enough to get her ass) and made her cum hard, causing her MILFy asshole to grip my cock tight like a vice. Still no remote thought that my cock was special. What the fuck was wrong with me. Thanks porn.

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My first true long term girlfriend didn’t help AT ALL WHATSOEVER. This one absolutely solidified that my cock was below average at best. We had plenty of sex, but lacked in the chemistry department. I was with her for many years. She was on the pill but made me wear condoms because, “sex hurt without condoms.” At the time, I was still naively wearing regular sized condoms and assumed she needed the latex barrier to avoid some sort of an allergic reaction. I’ve now come to realize she liked me to wear condoms because the standard sized condoms more-or-less shrink-wrapped and shrunk my cock to the point where she could handle it. Our libido was mismatched and sex with her was average was best. She could only reach orgasm from manual clitoral stimulation and often needed to think about other women to climax. My cock just did not do it for her (after we broke up she has since entered a relationship with another woman). She would often compliment my my cock as being “beautiful” and “pretty” but this didn’t help me to recognize the truth, I just thought she was being nice. She never went down on me and ultimately destroyed my confidence and furthered my belief that my cock was below average. After many years we broke up and I began another phase of being single.

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Feeling low, I met a wonderfully tiny (5’ 1’’) woman who became a regular FWB. The first time she unzipped my pants, she audibly gasped and her eyes lit up when my cock escaped from my underwear. She wrapped her hands around my cock and for the first time in my life, there was a solid inch of space between her fingers and thumb, they could not wrap around it entirely. This was the first time I had seen this outside of porn — she could could not stop squealing with delight about my “giant cock.” She would constantly and regularly comment on my hugeness, how it was stretching her out and filling her up. She was the best at literally sucking the cum from my cock and I was obsessed with her oral abilities — always demanding that she could only cum on my cock if she was a good girl and sucked me dry after. I would bury myself inside of her and she would grind her cervix / a spot on the head of my cock, bringing her to multiple, powerful, starry eyed daze inducing orgasms, which she would always dutifully follow with a soul draining cock suck. This was the first time I really got the hint — feeling her cervix/aspot grind against the head of my cock and seeing her tiny hands and their inability to wrap entirely around me, making my cock look just like the big cocks from porn. Perspective is a powerful thing. Still, for some insanely conditioned reason, this wasn’t enough.

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I had a string of other partners during this period of single-dom. One commented proudly that, “I always pick the guys with the prettiest and biggest cocks” after unzipping my pants. Others would regularly get fucked into oblivion and tell me that I was giving them the most powerful orgasms of their lives. Some would bleed (a bit) from sex and be perfectly fine with it, citing it as a welcome trade off for cumming so hard, over and over. Many of my partners would become clingy, (I’ve always been more independent and more of a loner, aside from my few serious relationships) playfully citing being “addicted” to my cock as the reason for their open clingyness. I traveled home for a wedding and ended up in the bed of my first girlfriend for a mutually agreed-upon one night stand, to relive our earlier chemistry. She came often and hard, as she always would, and straight up told me “Your cock is huge and I wish I had realized that when we were together years ago, nobody since has lived up to you.” Still – just thought everybody was being nice and lying. My head was fucked.

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I met an older, promiscuous woman and we struck up an ongoing sexual relationship. This is where I started to really get the hint and my warped sense of self and self image started (but didn’t fully) to snap into reality. She had many partners and often told me that my cock was the “biggest and most aesthetically gorgeous cock” she’d ever had the pleasure of fucking and sucking. She regularly and often used adjectives like, “huge,” “gorgeous,” “beautiful,” “thick,” and “perfect” to describe me and was obsessed with having me inside of her in any and all ways. I typically shoot big, long distance loads (trained up to this thanks to my insecurities) and her mouth watered at the thought, sight, and feeling of being absolutely coated with my cum. She would call upon me regularly, often multiple times a week. She would order my uber, dinner and drinks would always be waiting. She would give me a full body massage, suck my cock, and we would fuck for hours. She was insanely orgasmic and would cum and gush countless times per session. I had never had anal sex prior to this and she generously let me fuck her ass (she held that hole on reserve for special partners and said she “could not pass up having a model cock pound her asshole”) and pound away I did, being sure to ram every inch in and out relentlessly (honestly, feeling the unique and unusually beautiful sensation of my cock sliding into and out of an ass for the first time nearly brought me to tears). She described our anal sessions as bringing her to a “near constant orgasmic state,” telling me that my cock railing into her ass with such power caused juices to constantly flow out of her pussy like a gentle stream and her body and brain to feel like one giant everlasting fireworks show.

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She was quite an exhibitionist and brought me to a sex-themed party. At the beginning of the party, a couple began to have sex in a bedroom with the door open, wordlessly inviting others in to watch. Rumor spread throughout the party that the man was well endowed and all of the women rushed to see, eyes-wide, and gasping about his size. I stayed far away out of embarrassment and shame, knowing I would feel inadequate next to him. She of course went and watched while I stayed back, shy-ly nursing my drink. She came back and confidently reported it was big but nothing compared to mine — and that she was truly the luckiest one at the party. Despite this direct comment and all prior evidence to the contrary, I still thought she was just being nice and polite.

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She once brought a younger friend of hers (this girl was closer to my age) over to show off my cock. She was quite proud of having me as her plaything and wanted to watch someone else’s body, pussy, and face react to my size. The pair sat on the bed like puppies awaiting a treat as I unbuckled my belt, unzipped my pants, and pulled out my cock. Their eyes widened and the friend immediately grabbed me and swallowed as much as she could, pulling off for air, and after catching her breath, stating with a smile that I my cock indeed was, “deliciously long, unusually thick, and aesthetically gorgeous.” They took turns sucking me in tandem and the friend was eager to feel me inside of her, letting me know that “cocks that are long AND thick like yours done come around very often.” I bent her over the bed, spread her ass open for me, and slowly, very slowly slid myself inch by inch inside of her as she winced and whimpered. This next part surprised me and helped to open my eyes to reality. As a man, I never realized this, but I’m sure women reading can relate. During the first several minutes as I was fucking her slowly, my older partner rubbed her back the entire time, comforting her, telling her “I know it hurts right now, but once he stretches you out and you get used to him, you’ll have the best orgasm of your life, I promise.” About 10 minutes later, it came true, and she came hard. Watching my older partners eyes and face light up as she verbally encouraged her friend to explode on my cock like a cheerleader encouraged me to slam harder and harder through her lengthy orgasm and when she was finally spent, I instructed the pair to get on their knees and I promptly coated their giggling and smiling faces with rope after rope after rope of my cum. They licked each other clean as I was cleaning up and for the first time, I thought that maybe my self image regarding my perceived small cock was really off and very wrong.

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Shortly later, I met the love of my life. I broke everything off with previous partners and was head over heels. We hugged after our first date and she smiled, looked at my crotch, and caught me off guard by saying “you’re big, aren’t you? I could feel you.” I didnt know how to respond, and half jokingly apologized and told her I had a small cock. She laughed it off and we planned a second date. After our second date we hooked up and she marveled at my size, just like the others. Telling me how big I am, how thick I am, how my cock was the hardest and prettiest she’d ever seen. She is wonderfully small, her fingers can’t wrap around me and when she strokes me with two hands there’s plenty left over for her mouth. I wore a condom when we had sex for the first time and the condom broke. I wore a condom when we had sex for the second time and the condom broke. She finally asked what type of condoms I was using and I showed her the blue, regular trojans, and she laughed, telling me I was an idiot and that the condom kept breaking because they were too small. She convinced me to buy Magnums and truthfully the process of buying Magnum condoms couldn’t have been more mortifying. I felt like the biggest liar, fake, and jackass (I’ve heard too many stories from women about guys showing them magnum condoms as a brag, only to later and comically find out upon seeing their dicks that the magnums weren’t necessary at all) bringing them to the counter at CVS. After our date she asked if I got the magnums, and I told her the story about my embarrassment, which led to me telling her everything about my small size and sexual insecurities. She gently laughed throughout and told me that she wasn’t lying, that my cock was the biggest shed ever been with, and the prettiest she’d ever seen (“your cock is thick, pretty, reliable, and strong, like a Disney prince”) and she reiterated again that she wasn’t lying to be nice. She said she would prove it — she took out the magnum condom and rolled it on my cock. The whole time I expected it to be insanely loose on me, or not roll all the way down. I was shocked at the actual result. It fit better than any other condom I’d ever worn, and unrolled right at the base. Sex in this condom felt better in every way and I immediately understood how the plain blue condoms literally and uncomfortably shrink wrapped my cock down, making it smaller and easier to take for my ex. Flash forward through vulnerable conversations about insecurities, an insane amount of sex (and more magnum condoms), and one instance where she convinced me to allow her to photograph my cock and show it off to her gay friends who enviously confirmed the hype, I’ve finally come to terms with the fact that my cock is special, and impressive, and quite large, and I could not be happier.

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Hope this was an enjoyable read on multiple levels — both purely sexual (you’re welcome) and as a relatable (no matter what your size) ‘your cock is awesome,’ despite whatever you may think NO THANKS TO PORN” story for any men who have struggled with or struggle with this insecurity about size or performance in any way. Looking back at my sex life and writing these memories down without this insecurity clouding my vision really opens my eyes to how blind I was, how real and unhealthy this conditioning can be, and how lucky I truly am. Even though this is a throwaway account, all are welcome to DM with any comments, questions, or stories that relate — especially if you are struggling with this insecurity, or are just a fan of big cocks.

Source: reddit.com/r/gonewildstories/comments/b35qgm/well_endowed_a_detailed_sexual_history_of_how_i