The Most Disappointing Dicks I've Ever Encountered

It's About Way More Than Just Size...

Having sex with a new partner is a risky game. As a straight woman, my two major concerns are: how big is his dick, and am I going to get out of this alive, i.e., is he going to rape and/or murder me. Those matters aside, there are a variety of other, smaller concerns regarding things like pubic hair maintenance, sexual chemistry and rhythm, erectile function and the sometimes awkward aftermath (especially if any of my concerns were legitimate).

There's no surefire way of knowing how unfounded or well deserved any of my concerns are until it's already too late, and as such I have been woefully disappointed on many occasions. 


To be fair, all sex-having humans, straight female or otherwise, face similar risks when engaging with unfamiliar genitals. Safety, smell, size and hair concerns are universal for sure, though tolerance for our physical differences seems to vary greatly among us. For instance, I am an unapologetic size queen with little patience for a tiny cock, yet I have many friends who would argue all night long about how little this detail matters if you "love the person" or "get creative" — we shall remain forever at odds on this topic because their logic is bullshit. Anyway! Speaking of dicks...

In my meager history of encounters with the male sex, there are several which stand out as being the MOST disappointing. Here are some snapshots:

**NOTE: The numbers below are references to the order of appearance in my list of sexual partners which is not in consecutive order, but order of recollection. The order of appearance here is meaningless.**

#51: Handsome, younger, cut body to beat the band and anxiety that made his dick extremely unpredictable. He earns a spot on this list because he also could and would cum at the slightest squeeze or movement of my vagina. Nearly every instance of intercourse involved him inserting himself from behind while we were both standing, after which I would have to remain perfectly still as he acclimated to the sensation. Even after dating long term and monogamously, he preferred to use condoms to lessen his sensitivity. So much fun for me.

#23: Slightly older, fit, good-looking, very gainfully employed, German with a noticeable accent that was intoxicating. This guy had a penchant for BDSM through roleplaying, rule setting and physical acts that didn't involve any toys or equipment; the German accent really amped up the sexiness in this department. Despite the incredible chemistry and exciting line crossing, he was poorly endowed. Our affair was longer than usual in such a circumstance because we waited more than a month to have intercourse; my sexy German lover was well aware of his shortcoming and wanted to delay my inevitable disappointment for as long as possible. I was able to tolerate sex with him for about two weeks before I gave up.

#39: Even older, ex-con, ruggedly beautiful, cruel streak. I fell in love with this one unfortunately, the physical and intellectual chemistry too strong to resist. But alas, though his dick "looked good in the hand", as he described it to me before we slept together and I confided my concerns about size, it was unreliable. Right when I'd be about to cum, bam! Erection loss. There were times later, post-couple, when we engaged in a satisfying fuck buddy arrangement, but that ended after a few months because he had started drinking again and the aforementioned issues were only made worse by the inevitable liquor dick. My disappointment with this dick is possibly the greatest of all because everything else was SO FUCKING GOOD that the deflation was extra devastating in comparison. Even now, I'd risk it just for the good parts.


No #(a): Ok this one I didn't even see but I felt if through his jeans when we were making out on a waterbed and I decided to end it there. This guy was the same age, rail thin and one of my best friends. Prior to our make out session we briefly discussed how strange it was we had never hooked up. Well it will remain never; that shit was the hardest, skinniest, asparagus spear-like dick I've ever encountered and I am relieved to have avoided seeing it in the flesh.

No #(b): Another unseen penis, that of an adorable, same-age friend with fascinating hobbies, a great personality and an intoxicating darkness. Unfortunately his dick felt like a slim hot dog (again, another make out groin graze) and I immediately made up some excuse why I needed to go to bed and why he had to leave my apartment. Dodged another bullet there.

#54: Another anxious guy, adorable and pale. This one was small for sure but not unworkable. What was unworkable was the lack of effective erection, complete absence of rhythm and apparent lack of distinction for when his flaccid penis was smashing up against my pubic bone versus when it was actually inside me. Also, the first notable case of shaving having an incredibly ill effect on the visuals; the lack of hair only highlighted the small size of both his shaft and testicles and the result was uninspiring and depressing. The mental gymnastics required to go forth and work with what was in front of me were nothing short heroic. 

#47: This guy should be on another list of the biggest, most wonderful looking cocks but instead he's on this list. Yes his dick was HUGE and yes it got pleasingly erect, but goddamnit this guy couldn't ejaculate for anything. While fucking him was very satisfying, it always hit a point where I was dried up and irritated, impatiently doing all I could to both survive the experience and get him to finish. In all the times we hooked up I think he came once and it was after hours of fucking. Despite his massive member, I just can't imagine committing to the time and frustration that would be required to physically engage with him ever again; it is the saddest waste of a good dick I can imagine.


So there you go. This small selection of disappointing encounters is by no means an exhaustive list but it does capture the extreme lows. The remarkable nature of these letdowns is almost enough for me to forget all of the other more minor frustrations in between... almost. 

But it hasn't been all downhill. There have also been many amazing and mind-blowing encounters, memories that will keep the spank bank well stocked and effective for years to come, but I'll save those for another time.

For all the other size queens out there, I leave you with this personally tested wisdom offered to me by a gay friend: observe a man's walk to determine endowment — those with short strides or who shuffle sheepishly are likely in possession of a small and poorly functioning penis. Also, a man with a big dick will never say anything about having a tiny dick; if a man ever mentions being small, do yourself a favor and believe him.

Want more? Sign up for our weekly email

MORE sexy sex stuff…