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Well Endowed: The Good & The Bad of Having a Larger-Than-Life Dick

Women say they want a well endowed partner, but do they really mean it? Here’s what it’s really like to sleep with a big dick.

Well Endowed man

A well endowed penis can seem sexy and exciting, but those who have actually slept with a big penis may say differently.

It seems both men and women praise the thought of either having or being with someone who is well endowed. But is a big dick really all it’s cracked up to be? Here are the facts that a well endowed package isn’t always a screaming good time for either party. [Read: Do women like the penis? 22 things that make a perfect cock that girls love]

World Record For The Biggest Penis

While the Guinness Book of World Records doesn’t document penis-related records *maybe too hard to measure objectively?*, they do exist! Roberto Esquivel Cabrera made headlines in 2015 when he was reported to have an eye-watering 18.9-inch penis with a 10-inch circumference.

Yes, you read that right—nearly 19 inches! While some might think this sounds like a blessing, Cabrera himself has been very vocal about how “bigger is not always better.”

Cabrera revealed that his extreme size has caused him more problems than perks. Women were reportedly so intimidated by his length that he couldn’t maintain a long-term relationship, and the sheer size of his penis—so long it hangs down to his knees—has prevented him from working. [Read: 21 Awkward signs a girl is intimidated by you & what to do about it]

Everyday tasks, such as walking or even sitting down comfortably, became challenges. Cabrera has even applied for disability benefits, using X-rays of his impressive appendage to support his claim.

And just when you think this couldn’t get more outrageous: photos exist. Cabrera’s penis, often wrapped in bandages to avoid injury, has gone viral on the internet.

There’s even a report of him being able to slap it against his face while seated. *We’ll let that mental image sink in.* If you’re curious—and very much not at work— Cosmopolitan’s story covers this bizarrely fascinating tale. Proceed at your own risk!

Speaking of well-endowed facts, did you know that ancient cultures often had very different ideas about size? For instance, in Ancient Greece, smaller penises were actually considered the ideal.

Greek statues of gods and heroes frequently depict them with modestly sized genitals, which symbolized intelligence, self-control, and civility. Larger penises, on the other hand, were often associated with animalistic or brutish behavior. Essentially, they believed that a smaller package meant a bigger brain! [Read: 32 wild & kinky things to do with your boyfriend in and out the bedroom]

Factors Affecting Penis Size

Is Roberto Esquivel Cabrera just exceptionally blessed *or cursed, depending on how you see it,* or are there specific factors that determine why someone is well endowed? While extreme cases like Roberto’s are rare, there are several contributing factors that influence penis size. Let’s break it down:

1. Genetics

Genetics plays the most significant role in determining penis size. Much like height, eye color, or facial structure, penile size is largely inherited from your family’s gene pool.

If your father or grandfather were particularly well endowed, there’s a higher chance you might inherit those traits. However, it’s not always a direct line—genetic expression can vary, so having a well-endowed relative doesn’t guarantee the same for you. Simply put, size is mostly a biological lottery controlled by your DNA.

2. Hormones and Development

Testosterone levels during puberty are another major factor influencing penis size. During adolescence, the surge in testosterone helps drive genital growth and overall physical development. [Read: 340 signs of high testosterone, what it means, causes & ways to increase it]

If testosterone levels are lower than average due to medical conditions or hormonal imbalances, it could result in smaller penile size or underdeveloped growth.

On the other hand, unusually high levels of testosterone may lead to someone being exceptionally well endowed. However, once puberty ends, any further hormonal changes have little to no impact on penis size.

3. Ethnicity and Geography

Scientific studies have shown that average penis sizes can vary by ethnicity and geographic location, but it’s important to approach these findings carefully to avoid harmful stereotypes.

Research suggests that men from some regions, like parts of Africa and South America, tend to have higher averages, while other regions, such as East Asia, tend to report slightly smaller averages.

That said, these are only statistical averages, and there is plenty of overlap between individuals worldwide. Being well endowed isn’t exclusive to one group or region, and genetics still play the dominant role.

4. Myths vs. Facts

There are plenty of myths about what influences penis size, and it’s time to set the record straight. For instance, there is no scientific evidence that shoe size, hand size, or even height correlates with how well endowed someone is. [Read: Grower vs shower: How it’s different & ways to tell which penis is better]

Similarly, claims about foods or exercises “increasing” penis size are baseless. Your natural size is determined by factors like genetics and hormones, not by external characteristics or unproven remedies.

5. Truth About Penile Enhancement Products

Despite what late-night infomercials or online ads claim, there’s no miracle product that can make you more well endowed. Pills, creams, and non-surgical devices lack scientific backing and often deliver disappointing *or non-existent* results.

Surgical procedures, like penile implants or ligament cutting, exist but are typically reserved for medical conditions and come with significant risks. The truth is, penis size cannot be significantly changed after puberty, so most enhancement products are little more than a marketing gimmick.

The Upside of Being Well Endowed

Let’s face it—many men dream of having a larger penis, and society has done little to discourage the idea that being well endowed is a ticket to confidence, desirability, and better performance. In fact, studies suggest that around 45% of men feel dissatisfied with their penis size, with some even developing anxiety about it. [Read: Sexual anxiety: 25 secrets to not feel nervous about having sex & enjoy it]

But for those who fall on the “larger” end of the spectrum, there are undeniable upsides that many consider an advantage. Here’s why being well endowed can be seen as a good thing:

1. Increased Confidence

For some men, being well-gifted provides a significant confidence boost. Societal perceptions often associate a larger size with masculinity, sexual prowess, and desirability. Feeling that they meet or exceed these expectations can enhance self-esteem in intimate relationships and even in non-sexual contexts.

While it’s not the case for everyone, some men genuinely enjoy the mental and emotional advantage of knowing they stand out in this department.

2. Partners MAY Find It Desirable

Sexual attraction is subjective, but there’s no denying that some partners value larger penis sizes. For individuals who prefer the feeling or visual appeal of a partner with a big dick, size can enhance sexual chemistry and intimacy. [Read: Sexual chemistry: What it is, how it feels, 52 signs & ways to increase it]

This preference isn’t universal—what one person finds exciting, another may find intimidating—but for those who appreciate it, being larger can be a bonus. This can sometimes make intimacy more exciting and fulfilling for both partners, provided that communication and mutual comfort are prioritized.

3. Enhanced Visual Appeal

There’s no denying that larger penises often attract attention. Whether in a locker room, during intimate encounters, or even in photos, being well endowed can be visually striking.

Some men find that this attention is flattering and boosts their ego. Additionally, the novelty factor of being unusually large can make intimate moments feel more memorable or adventurous for both partners.

4. Potential for Greater Sexual Confidence

Being confident in bed often translates to better performance, and for some men, having a large penis can contribute to that confidence. [Read: Sexy ways to be incredibly good in bed & leave anyone wanting more]

Feeling that they’ve got a “natural advantage” can make them more willing to explore different positions, be creative, or take the lead during intimacy. When combined with a focus on their partner’s needs and desires, this confidence can elevate the overall sexual experience.

5. A Source of Pride or Uniqueness

In some cases, being exceptionally well endowed can feel like a unique trait or even a fun talking point. Just as someone might take pride in an unusual skill or feature, men who are larger than average often find themselves feeling special or different in a way that makes them stand out.

This sense of individuality, when paired with a healthy mindset, can make being well endowed feel like an asset rather than a burden.

6. Social Perception of Masculinity

Cultural norms often equate larger penis sizes with virility and masculinity, which can sometimes lead to positive social perceptions of well endowed men. [Read: 29 secrets to be way more masculine & manly without being an a-hole to others]

Whether in casual locker room conversations or jokes among friends, those who fit the stereotype of being “larger” may find themselves getting lighthearted attention or admiration. While this can be superficial and context-dependent, it’s undeniably a confidence booster for many men.

Reasons Why Having a Big Penis Isn’t All It’s Cracked Up To Be

But having a large penis definitely isn’t as glamorous as you think it is. Same goes for sleeping with a well endowed guy.

1. Women Won’t Sleep With you

For smaller men, the thought of having a big dick means getting all the girls you could ever dream of. After all, bigger is better, right? While many women say they’d love to experience a well endowed partner, the reality is a shocking, if not scary, experience. [Read: Penis facts: 30 shocking & weird trivia to make you a dick expert in no time!]

“I was once about to hook up with a guy who was so small I thought I was cupping a testicle when I reached into his pants. We did not end up hooking up, and I left very disappointed. The very next guy I hooked up with was so big, like 10 inches, that I thought I was holding a steel pipe when I reached into his pants! We did not hook up either. It was terrifying.” – Cassidy, 25.

“My last year of college my boyfriend and I broke up, and I was ready for some mindless sex. I had heard from a girlfriend that a guy we knew was particularly blessed in his nether regions. Naturally, I wanted to conquer.

We started fooling around and I was literally tongue-tied when he whopped it out! I am very, very petite. Suddenly I had visions of him on top of me, seeing his member slithering visibly under my stomach skin like the chest-bursters in Alien! We did not sleep together, and he was very understanding about it.” – Miyako, 29.

“My first boyfriend was about nine inches and let me tell you, that’s way too big, girl. We could barely ever have intercourse because he was so thick around, it felt like he was skinning my vagina from the inside out.

I would usually try and give him a blowjob but could only get the tip in. I’m sure this was unsatisfactory for everyone involved. My next boyfriend was only about five inches, and I was so relieved.” – Lauren, 27.

2. If They Do, They May Cheat On You

That’s right, women are more likely to cheat on men with large penises says this study. That is life’s cruel irony. The study suggests that for every inch longer a penis was, the likelihood of the wife cheating went up by one and a half.

The study’s findings indicate that of the 545 wives polled, 6.2% were cheating on their husbands. When not citing domestic violence or other legitimate reasons for cheating, many women cited that their husbands were unskilled in the sack.

The study also showed that women associated larger penises with sexual dissatisfaction. The research then showed these hubbies were so well endowed that their wives took to smaller men to satisfy them, pain-free. [Read: Who cheats more? Men, women & their specific needs to cheat]

3. Or They Will Stereotype You

“Women seem to be under the impression that just because I have a larger penis that I’m a douchebag player. I’m not a cheater, and I don’t play games with girls.” –Mark, 33, 9”

“Girls talk. Man, I mean they talk a lot. Everyone at the bar I frequent knows my size because of a waitress I hooked up with there. Not going to lie, the attention is nice. But at the same time, not to sound like a baby, but I feel like the girls are only interested in me for my dick. That’s not always a great feeling.” –Anton, 28, 11”

“I’m not even really that big, but women still think I’m out sleeping with a hundred girls a week. Definitely far from true. Also, they stare at my junk a lot. I now know how girls with large chests feel. My eyes are up here!” –Tanner, 39, 8.5”

4. You Can’t Hide Your Erection, Not Even At The Airport

Falcon was actually pulled aside and frisked at an airport in San Francisco due to a large bulge in his pants. Turns out the only weapon he was concealing was his massive 9-inch flaccid penis.

A 1999 HBO documentary listed Falcon as having the largest penis on record at that time at a whopping 13.5-inches erect. [Read: How to make a guy hard: 25 casual & subtle moves no man can resist!]

5. Clothes Are Suddenly a Problem

When it comes to shopping for clothes most men are quick to chuck a few items into the cart and call it a day. Men who are well endowed tell you choosing a wardrobe isn’t so cut and dry.

Shorts are a nightmare, workout clothes leave little to the imagination, and jeans are restrictive against the extra leg in there. A big penis shows up no matter what you wear.

While this may seem like a goldmine wardrobe for getting laid at a club, it’s not so exciting when you arrive at grandma’s dinner with your giant dick visible.

 6. Difficulty with Oral Sex

Men with larger-than-average penises often find that oral sex isn’t as simple as it might be for others. Partners may struggle to take them fully, and the process can become awkward or uncomfortable.

While communication and adjustments can help, this is another area where size can complicate intimacy rather than enhance it. [Read: 49 blowjob techniques, positions & tips to give good head & make him gasp!]

7. Awkward Situations in Public Settings

Whether it’s sitting on a bike, crossing your legs, or being in a crowded public space, having a large penis can lead to frequent moments of discomfort or awkwardness.

Situations like accidentally sitting on your own penis or feeling constricted in tight spaces are rarely something others would think about—but they’re very real problems for well endowed men.

8. Frequent Chafing or Irritation

The sheer size of a larger penis can cause friction against clothing or skin, especially in hot or humid weather. This often results in chafing, irritation, or even rashes, particularly if underwear doesn’t provide enough support. Managing these issues can be an annoying and ongoing task.

How to Have Sex With a Well Endowed Man

If you’re with a guy who’s packing in the pants, there’s no reason for all that girth to go to waste. If you’re determined to make the most of your sex life, we suggest the following tips:

1. Communication is Key

When it comes to dating or having sex with a well-endowed man, open and honest communication is essential. Let your partner know how you’re feeling, especially if size creates any concerns or discomfort. [Read: Why does sex hurt? Quick signs something’s not right]

If penetration feels intimidating, express this early and kindly. Most well-endowed men are aware of the challenges that their size can bring and are usually willing to work with you to make intimacy enjoyable and stress-free.

2. Relax

It isn’t a monster, so stop treating it like one. The more you freak out the more anxious your body will be when the big moment arrives.

3. Foreplay

If you thought you needed foreplay for an average-sized penis, you’re going to need about 10 times more for the gigantor you’re now up against! [Read: Sexual foreplay: 26 lusty secrets to do it well & make them hot & horny]

Go slow and allow time for the vaginal walls to stretch out. Like, lots of time. It may be beneficial to have an orgasm via hand stimulation or oral sex before penetration to ensure you are wet and ready.

4. Take Your Time

Rushing into things—especially during sex—can lead to discomfort or even pain if your partner is well endowed. Foreplay becomes even more important in these situations.

Allowing yourself to fully relax and be aroused helps the body adjust, making penetration easier and more comfortable. Using slower movements at first can also make the experience smoother and reduce tension for both partners.

5. Lube

Lubrication is an absolute must when sleeping with a well endowed man. Lube will allow for more clitoral friction and decrease the odds of tearing or pain during sex. [Read: The best lubricants for sex: 15 winners from the kitchen cupboard]

6. Tell Him When It Hurts

This isn’t anal. Pain is not an expected side dish with vaginal intercourse. Don’t try and be the “cool girl” if you’re in pain. Again, open communication is essential for either of you to have a good time during any form of big dick sex.

7. Don’t Expect to Take It All

Conquering Mount Everest is definitely a brag-worthy feat, but arriving at the base makes you realize the pain you’re about to endure just to make the summit. This is how you should feel about conquering every inch of your partner’s manhood.

It would be foolish on both of your parts to expect to use the entire length inside your vagina. Only let him insert as much as you can take and have him do careful thrusts from there.

8. Understand That He Might Have His Own Insecurities

While society often glorifies having a big dick, men with larger penises may have insecurities of their own. Your partner might worry about hurting you, being objectified, or meeting expectations based on stereotypes. [Read: Insecurity in a relationship: 34 signs & secrets to feel secure and love better]

Being supportive and reassuring can go a long way in helping him feel more comfortable and confident in the relationship.

9. Avoid Stereotyping Your Partner

It’s important to approach your relationship with your well-endowed partner as you would with anyone else—by focusing on who they are as a person.

Avoid making assumptions about their sexual prowess or personality based on their size. Remember that a man’s value isn’t defined by how well endowed he is, and he likely doesn’t want to be reduced to just one physical trait. Treat him with respect, and avoid making objectifying comments or jokes.

10. Choose The Proper Position

Choosing the best sex positions for a well endowed penis allows both of you to enjoy yourselves. For example, avoid doggy as well as any position where your legs are up in the air, as this allows him the deepest penetration. [Read: Why are men obsessed with penis size? 21 awful truths about penis shame]

Here are some of the best positions for a well endowed partner:

Spooning or standing

Any position where he only has access to shallow thrusting is going to be your new best friend.

Girl on top, reverse cowgirl, side saddle

Girl on top positions are great since you’ll be given control over what angle, depth, and pace you handle his XXL member.

One final tip? Pre-sex stretching is highly recommended.

[Read: The 13 types of penises women love… or laugh at!]

Blessing or Curse?

It’s easy to assume that having a large package is all fun and games. Society glorifies the idea of being well endowed, making it seem like the ultimate advantage in relationships and sex. While there are perks, it comes with a laundry list of challenges that aren’t exactly sexy.

[Read: 34 passionate signs he is making love to you & not just having sex]

So, is it a blessing or a curse? Well, it’s both, depending on how you approach it. Being with a well endowed man isn’t always the joyride you think it’s going to be. Remember to stretch first, breathe deep, lube up, and give it your best shot. And if it doesn’t work out, at least you can say you’ve seen the biggest dick of your life.

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Natasha_Ivanovic
Natasha Ivanovic
Natasha Ivanovic is an intimacy, dating, and relationship writer, and the creator and author of her short stories on TheLonelySerb. She completed her first degr...
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