Hapless

Mine was probably this one day with this girl I'd had a crush on for more than a year. She was extremely attractive, and really bold and ambitious. I'll say this much about our plans, she'd had an idea involving weed, a tent and a steaming rock to create a weed sauna. It sounded great to me so I went along with it. When it came time though, she began to strip to her underwear and said I should too or else my clothes would be soaked from the steam. I was nervous because I didn't want her to see my small penis, but went along with it thinking that I'd at least be in my underwear.
But when I was taking off my pants I saw that the flap on my boxers flung open and my penis was in plain view, it being so small that it could be seen in it's entirety through the little flap. I quickly stood upright and looked over at her and I saw her grinning and covering her mouth. Then she began to giggle and she said, "You're so small!" and then began to laugh. I was so humiliated, but turned on at the same time.

From that point on she would make little comments about my tiny penis whenever she had the chance, and she didn't care if other people were around. About a year later she and I were hanging out at a bar and she made some comment about me being small and I called her out saying she'd never seen my penis, but then she recounted this entire story, saying she'd seen my penis through the flap. I asked her what she'd thought of it and she began to giggle and made the small sign at me.

That was probably the most humiliating moment, because on top of the girl I'd been crushing on seeing me naked, I'm sure she told all her friends and my friends because that's the kind of girl she is.

smallcocked

Lol I have had a somewhat similar moment. I was in love with a girl who was really hot and tall lik 5'11 at least (I am 5'8 and have a thing for women taller than me) . I seduced her into having sex, when she saw my "penis", sh laughed like no tomorrow lolx, that got me really turned on and i got hard. More laughter. When she saw that it wasnt getting any bigger, she used her pinky finger to compare it with my erect member. Seeing, she was tall, needless to say her fingers were frakishly big and long also, it was no surprise her pinky was longer than my erect "dick". I was tomato red with humiliation. Can never forget that day. She however, allowed me to get inside her just for the heck of it, it was her first ever small cock. Eventually, I came too fast and she couldnt feel a thing anyways, so she said I better eat her out or im telling everyone how pathetic you are. obviously that left with me no choice. but every time she sees me she makes that pinky finger gesture and flashes a devillish grin lol..I get turnd on by it now, though. LOL

noblet

my most embarasing time was when my wife told a girl that i worked with of my submisive situation and the size of my tiny penis. the girl is a pretty 25 year old indian called meena .i am constantly locked into a penis cage and my wife and meena both keep a key on chains around their necks .now and then the question is asked "whats the key to" i fear one day they will expose my secret.

ian32

Once I was talking to this really hot girl, like she had most amazing ass I've ever seen, even in porn, and I finally convinced her to date me and one night she told me that she'd give me a handjob if I wanted. When we were about to do it, when she saw my dick she grinned and said "it's a little smaller then I expected..." I didn't say anything back, I acted like I didn't hear her, so then she starts stroking my dick, and about 10 seconds into it she sees precum and laughs and says "Aww! It's like your little penis is crying!" then while she was saying that she only had two fingers around my dick and she was rubbing ridge on the head of it and then I cummed 2 little drops and she just laughed more.
It was really embarrassing, but it made me really horny when I thought back to it after she left.

EEKK

I had an ex in high school who was completely into humiliation (her favorite thing was to try to get me to cum in my pants between classes, it worked once or twice and i had to pretend i spilled a drink). One time, we were hanging out at her place with one of her girlfriends. While talking to her friend, she snuck up behind me and yanked my shorts and boxers all the way down to my ankles. Both girls got a great laugh from my tiny dick, her friend even took a cell phone pic and threatened to show her friends!

On another occasion, she invited the same friend to go out to eat with us. They spent the first twenty minutes recanting and laughing at my pantsing. I excused myself to the restroom and when i came back, both girls were quiet yet giggling to each other. My ex motioned for me to take the inside seat at the booth. Almost as soon as i sat down i felt a foot caress my inner thigh. My dick became instantly hard. When the waitress appeared the foot disappeared, when the waitress left, the foot came back. Our friend leaned down in her seat and i felt her toes squeez and massage my dick head. Both girls giggled and my ex leaned over and whispered, 'Your going to cum before our food gets here, or Shauna will show our waitress how tiny your little pin dick is.' I looked up and our friend was holding her phone open with my pantsing picture on display and giggling even harder. That was all it took and i emptied my balls all in my jeans. Both girls were completely amused by this, my ex poured some water in my lap and told the waitress i had an accident. Best night ever!

EEKK

The same aformentoned ex-girlfriend also embarrassed the hell out of me at school one time. We were eating lunch with some friends at an outside table when the conversation found it's way to a friend of ours former boyfriend and how small his penis was (three inches if I remember correctly), when mid way through the discussion I felt Katrinas (my ex) hand start heavily petting the crotch of my jeans. She got a near perfect tent going and literally started jerking me through my pants! I swear I thought I would choke on my food if she kept going. There was a break in the conversation and she turned her head to give me a devilish look and all of a sudden, I knew what was coming. Her hand left my groin and I felt a moment of relief which quickly turned to horror when I felt my pants being unzipped. I had no time to protest before her hand pulled my dick through my fly and start slowly stroking me with three fingers. The conversation continued for a little while longer before she started motioning to my lap with her head. Are friends peeked under the table and immediatley started laughing and making the "small penis sign" with there thumbs and index fingers. I felt like i could have died. The lunch bell rang and Katrina and are friends got up and walked away still laughing leaving me at the table penis still out. I tucked it back into my pants and went to class trying desperatley to hide my tiny buldge!

smallbutcute

have my sisters pull my swimming trunks down after swimming in a cold swimming pool, my older sister held my hands above my head while my other sister pull my shorts down showing my shrunken small penis, it was pretty much just a bump, my sisters laugh so hard and remind me all the time how small i am and they have told there friends about my size

dammit

Last week I went to a strip club, the chick was practically slamming her ass hard on my pelvis, but to no avail. There was no bulge to be felt inside my pants. After vigorously grinding away at me for a few minutes, she finally stopped and gave me a little smile in a mocking way.

threeinches4u

my girlfriend told everyone at work I had a 3 inch penis when we broke up

littlep

I've never posed for drawing classes, but i've had an ex girlfriend who was in to photography. I still don't know how she did it, but she actually talked me into posing naked for her. I was feeling very uncomfortable and my penis was shriveled during the whole shoot. Of course the pictures were terrible. Me, red-faced, with a tiny penis, looking like I was forced to pose nude, which somehow was the case. My girlfriend found all this very amusing and she even showed the pics to her mother and younger sister. Her mother found, who was also an artistic type, found it very 'authentic', but her sister practically peed her pants laughing.