The Small Penis’d Boyfriend

Jill Pond
Written by Jill Pond

The story of the small penis’d boyfriend is a tale of woe and misery…

A bunch of years ago, I dated a guy with the smallest penis in the world.  It was about the size of an adult’s thumb and might very well have been in the running for micro-penis classification.

This guy and I dated for a handful of months, but our relationship was doomed from the start. The first weeks of our fledgling romance were bliss; I was caught up in the highs of new love and unbothered by his missing manhood. I was a lonely gal and the joy of having a boyfriend outweighed the needs of a horny girl.

Lonely always trumps horny in the beginning.

As the novelty of being a couple wore off, I began to wonder just what the fuck was happening. There was no sex, the dry humping was sparse, zero hand-job action and definitely no pearl diving. All things that horny people love to do. 

Was this guy a prude? Was it me? Were my tiny breasts so off-putting that he wanted nothing to do with me? In hindsight, I’m guessing that he had some serious wangxiety swirling around in that man brain of his, but I made it all about me. 

On the bright side, it was the easiest head I ever gave – no choking, no gagging, no poking of the soft palate. Gross, I know, but as time passed with favours un-reciprocated I began to feel very… what’s the word?


To my horror, the tides turned and horny soon kicked lonely to the curb. It never dawned on me that this man-child was sexually stunted due to his tiny tripod and there was nothing to be done for it. My young 20 something-self took his lack of interest as rejection; I was ugly, gross and unwanted.

Lonely will make a girl do stupid things and I stuck with him, hoping he’d come around, but as fate would have it, there was no coming for me. Each night we spent together, my small penis’d boyfriend happily fell asleep beside my buzzing body. I’d stare at the ceiling, wondering what was wrong with me that he didn’t want to dive face-first into my crotch.

It’s not a stretch to say that the young and insecure suck at relationships. I lacked the confidence and ability to start a conversation that would have addressed both of our issues.

“Hey, sweetie? I’m fucking horny – why won’t you touch me?”

“Well, Jill, my whole life I’ve had this small wanker and as a result, I fear all sexual contact because it will just lead to intercourse, and frankly, I’m not sure this baby thumb can even penetrate.”

“Wow. So this isn’t about me? Well, I’m super good at masturbating, so I can teach you how to please me with your hands and fingers. Would that be a start?”

“Yes, I’d like that. Thank you for allowing me to be vulnerable.”

Um, whatdafuck! The likelihood of me being able to go down on my own self is higher than finding a 25-year-old capable of having this conversation.

No, my response was to break up with him and gossip about his tiny dick because I felt so rejected and angry. Not nice, but like I said, young, insecure, lonely… I was an asshole but I lacked the emotional maturity to handle it otherwise.

I haven’t seen Tiny or his tater tot in many years, but I hear about him through old high school friends. Apparently his gherkin was pickled enough to father a few children. Don’t get me wrong, my heart sort-of goes out to him and his stump, but our time together was enough to leave me with resentment and hurt. I try to have integrity in my dealings with people, but when your lover takes no interest in loving you, my first instinct is to find the dysfunction in them and bury a fucking axe in their back.

Would it be wrong to give advice to all of the penis-challenged men out there? Would I be remiss to point out that phallic friction is lovely, however women who have penis-induced orgasms are kind of like Unicorns.

We all kind of hope they are out there, but few have ever seen one. Fellas, face facts and learn to use the other tools at your disposal and you’ll be set.  A micro-peen doesn’t mean you can’t be a good lover, just like having a gigantic vagina doesn’t mean a gal can’t still please her man. 

Just own it and make do and we can all rest easy in an orgasm-induced stupor.

About the author

Jill Pond

Jill Pond

Jill is a seeker, writer and blurter of truth. She is a top-notch Vagina Evangelist, wife to a hoarder of camping gear and mother to 2 girls, 2 dogs and a cat who's been perilously close to death for several years now. From wildly comedic to tear-dripping serious, you can find her stories on her blog, Totally Inappropriate Mom, where her 'life-uncensored' philosophy, naughty humor and general inappropriateness run the show.

Leave a Comment

CommentLuv badge


    • Nice! Thank you Stephanie! I always wonder if somehow, my parents will come across one of my more risqué posts like this and I cringe, turn red and feel shame all at once, but then I laugh and say who the fuck cares- I’m glad people can laugh at it!! I just hope the tater tot never sees this…
      Jill Pond recently posted…Fat Roll FridayMy Profile

  • So, I must be a unicorn because I can’t orgasm from an Australian kiss but give me a good ride and if I can, I’ll scream your name haha. It sucks because my last boyfriend, not necessarily small, smallest I’ve ever been with, he couldn’t finish. Always hard. And he didn’t hurt or anything from not releasing his goods. Weird. And because of his lackluster length, I couldn’t get any from behind. Anyway, my point is, all dudes have penis issues. And that’s sad, because they’re awesome hahaha.

    • Ahhh, the penis. Such a strange organ to behold. Well, Ms. Unicorn, I’m happy for you and your clam, but sad that you’re ex-man’s tater tot can’t finish the deed. Good luck to you in the quest for a man sans wangxiety!
      Jill Pond recently posted…Fat Roll FridayMy Profile

    • OMG!
      My last boyfriend was average, couldn’t climax, and even though he gave good head, I couldn’t come from it. I’m also a Unicorn… And to not get it from behind was excruciating… 2 excruciating years… Lawdy

  • Been there with the small endowment. Been there with the selfish…but this unicorns thing. I had no idea it was so rare. Multiples, easily, from the penis. I think I need to do some research here.

    • Yea, it’s a fact. The percentage of women who “see jesus” during intercourse is quite small. There are also a ton of gals out there who have never “seen jesus” at all before. Sad. You, my friend, lucked out when god was handing out clitorises. Or, you have a magical g spot. Congrats, bitch. Kidding. Kidding. Lucky Bitch. Oh my god, I’m sorry. I just can’t control myself. Jealous.
      Jill Pond recently posted…Fat Roll FridayMy Profile

  • Wangxiety… love it. Your post may have saved me from a major melt down today. Please keep em coming! It may have just postponed it but only time will tell. Hopefully there will be “no film at 11”. LoL

  • im glad iv never had a gf.. women seem to be cruel and horrible communicators, instead of working out issues with their significant others they’d rather run to their gf’s and talk shit about him behind his back, making it difficult for him to land any other woman if from a small town… but in a big city who cares right? not like you have to see your ex in passing very often in a big city, so sure, keep up the smack talking behind their backs.. that’s going to make everyones lives a lot better!!

    • I agree. I think Jill Pond handled the situation very cruelly. Making fun of the size of a man’s penis is the most obnoxious, insensitive, shallow behavior that a woman can ever do to a man. There is no excuse for it. None. The size of a man’s penis is something he was born with and cannot control nor change. To judge a man that way and verbally attack him because of it makes Jill Pond a disgrace of a woman. There are many insecure men who are afraid to date and have sex because they are insecure about the size of their penis. For those men, the Jill Pond’s of the world are their worst nightmare. Even now, in the comment section, she is still obnoxiously and with total immaturity calling him names and laughing at him. How pathetic! There are good, caring women out there who would never treat, talk about, or hurt a man like that. Unfortunately, many men with small penises are afraid to try and find them for fear that they may encounter a horrible person like Jill Pond. The worst thing a woman can ever do to a man is to judge him by the size of his penis. No man deserves that. Love and romance should be the priority and not the size of body parts. If I could I would tell off all the Jill Pond’s of the world for cruelly hurting men like that (on the the shallow, superficial reason of the size of a body part that no man has a choice). Jill Pond and other women who have her attitude and behavior should be ashamed of themselves.

    • I agree, women are the cruelest of creatures. And Jill is just an asshole. She was an asshole when she was younger, and she’s still a superficial asshole. Wouldn’t be surprised if she had Narcissistic personality disorder…

      … because it’s all about you.

  • Small towns are a great place to spread rumors among local women. Personally I model for the local art group on campus. So let the women know my junk.

  • What about if it was cold that day? 😂😂😂😂 Great article. I found it by searching for “small hand holding penis.” I was trying to make a meme on my Instagram. Anyway, nice job!

  • Thanking you for the ending but curious as to how many women you did tell about his teeny weeny. Let’s just say I am curious because there will be no unicorns in my life and I live in a small town.

  • what guys like us with small an understanding women..which according to this article are non exsistent…they are selfish with their needs..what about being part of a team and work with him.. and remember not all guys like huge boobs on a GIRL…sometimes grat thinsg com in small packages..if you guy is small and seems scared of intimate contact..grabd his balls pull down his on.. it will take the pressure off him and mostly likey he will be chasing you round the room by weeks more selfish…be helpful..

  • My wife is cuckolding me. I really do not mind, since I love her and want her to be sexually fulfilled. This is just one area where I cannot help her (mine is just short of 4″). Why risk that she might start cheating. She has a fbuddy that she sees once a week and everyone is happy

  • Notting like the presence of lads, to shut down femal honesty. Women like to say men are obssessed with penis size, but the fact is most men only care about their own. Smaller average are obssessed with what they can do about it, while those above are addicted to being complimented on it and both because its women that love cock and as soon we show up they shut off.

  • im glad I only interact with women when they’re working a cash register.. my life sucks sure, but at least i haven’t experienced such hate from a woman before, much easier to remove myself from society let them fuck whoever they want until they find someone to be married to for 7yrs.. and then whatever, maybe when a woman is in her 60’s she just likes to have company in her life, maybe then, if im still alive

  • I know is old but I think its important to point out how his insecurity caused a growing one in her. Men try so hard to understand women just for our egos. Because we objectify them we create this image that women do the same.

    If a woman likes a big dick o well, mine is right under 6.5 and a Lil over 5 for girth….that’s not big at all but I’ve made a woman squirt and I know my way around. Women just want to feel wanted its us who want to be adored this article opened my eyes, ha ks for your honesty and that’s coming from a a man. Its a shame to see men on here getting upset when, again, there was a point where his insecurity reflected off you. I liked this, bout to ram me a mf like idk how because now I see it is men who praise size more than woman….thank god I made it to 6 tho

  • This was SO well written I enjoyed every minute of it lol. In fact, I laughed out loud at some bits. Us men are stupid. Or, at least we are at that age. We make EVERYTHING about our manhoods. And if it’s not related, chances are we’ll relate it.

    The sad thing is that it’s men that destroy it for men. As a guy that’s just below average in Weiner size, I had to spend my youth watching other boys in the cloakrooms get their police truncheons out and slap each other with them. To be quite frank it gave me an insecurity that would have never been there.

    It wasn’t at least until I aged 26 or 27 that I realised I can use my whole body to please a woman, and that my willy size wasn’t bad at all 🙂

  • Our dicks are *our* dicks. They should not define us any more than our elbows. Don’t like ’em? F off. Our manhood is not measured by the size of our wankers, just as the depth of a woman isn’t proportionately diametrical to the depths and widths of their love holes. Men are not a procreation utility.
    While we’re at it, stop the ludicrous association of small penises with big cars, gun fanatics, bullying, need for power, and general assholism. By that logic, the big dicks drive Priuses, wear lipstick, and listen to Justin Beiber while sipping wine coolers.

  • Wow… what an insecure, mean and selfish woman. I…. unfortunately am under sized and in a loving and fulfilled relationship. We can’t help what size we are but can fully and completely make up for our short comings.

  • It is obvious you are American and a complete bitch. You lambaste this guy who through no fault of his own has a small penis and the insecurities that come with it, mainly magnified by cunts like you. and yet you think by delivering a couple of lines of ‘sympathy’ at the end of your trail of garbage justifies your inhuman morality. Using your tiny tits to try and equalize the dilemma just doesn’t cut it. You wouldn’t talk about a Little Person like this. there again, maybe you would.

    • my ex partner of 20 years used to humiliate me about the size of my penis erect its 5 inches she never had a problem with it i have fathered 4 kids with my small penis the last 6 years of the relationship she was a nightmare asked me one night if she could measure it to see how really small it was then we were out one night and she met up with some of her female friends and she started telling them how small it was asking me to show them she even tried to take sneaky pictures of it so she could show people there is plenty more humiliating things she said but a left her three years later she txed and wanted sex like a mad man i went back too hers said she missed me was with her a couple of months we were llying in bed she said she was with some guy with a huge cock much bigger than yours said it was at least 10 inches long and that she could put two hand on it but couldent put her fingers together as it was thick but said she couldent cum with a big penis but came every time with me lol whats that all about

    • My GF loves my small penis because it does not hurt her when she is a little dry. Also she enjoys the massive load I put into her in a short time.

  • A man is BORN with whatever size penis he has. It’s stupidity and quite ignorant to make fun of any man for the size of it. Also, for you ladies who just have to have your vaggie stretched or filled up…. Did you know that women have DIFFERENT size vaginas? Oh? Well, yes you do. Which men could and should mimick and tease you about this and show you how fukcing cruel this is. Big floppy vaginas will need big ass penises….. So, now……