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Daniella, Aurianna & Lily Play Strip Jester 09/18/2009
Veteran Lily. Rookie Danielle. And complete n00b Aurianna gather to play a simple game of Jester, which again, is not so easy for them to do right now, but eventually there are two naked losers. It's those two who have to play the second game.A nice big massager is placed between them, both of them pressing their pussies against it. Initially, the rule was going to be that whoever came first lost, but the girls switched it to whoever couldn't stand it anymore and jumped away lost. That girl gets a forfeit, whil ethe winner collapses motionless and exhausted on the bed.What's the forfeit? Masturbation. Yeah, I probably could have thought that one through better, and it might not been so bad if the girls hadn't changed the rules like that, but the poor winner to rub her extremely sensitive pussy. Oh, and did I mention she had to do it in front of the window? We were up for a few stories, but people on the street could still see our window if they cared to look up.Also, there was a convention of church ladies in the hotel. Really...there was a convention of them. We'll meet some of them in a later clip, but for now, there bus was there. Did they look up? Did they see? I'm pretty sure the ultimate loser faked her orgasm at the end. Usually I don't tolerate that sort of thing, insisting that a masturbation to orgasm forfeit is a masturbation to orgasm forfeit, but in this case I let it slide.

Ashley and Kala Play Strip Four In A Row 09/18/2009
Do you remember this commercial? "I win!""Where?""Here, diagonally!""Pretty sneaky, sis." If you do, then man, you're old. But anyway..picture that commercial, except with the losing sister having to take off an article of clothing. No, wait, don't, those were two little girls, that's disgusting. Picture them grown up, in their twenties, and then the loser has to take off an article of clothing. Do that, and you'll have this clip. Lovely sisters Ashley and Kala challenge each other to Strip Four-in-a-Row, with the loser having to do ten naked jumping jacks for the camera.

Jordan comparing a dildo with a small tiny dick 08/28/2009
When my friend came over, she thought she was getting her first really big cock instead she got her first really really small penis. After she saw how small Jack was, she saw a big black dildo I use lying around and compared jack to it. You can guess how that went.She got really close to his penis she said it was because its so small its the only way she could see it. Watch the comparing and jacking the little penis fun.

A girl in shock at how tiny jacks dick is 08/28/2009
I met this chick while getting my nails done. She was really outgoing and told me it had been awhile since she had been laid. She was telling me how she craves a big hard cock. I told her I could hook her up. So she comes over and there is pathetic Jack. She is so excited she grabs him thru the towel and realizes she is getting caught short. She laughs at his small penis and this is where it gets good. She starts trying to stroke him and he is so inside its like there is nothing there. So she takes off her ear ring and compares him to her ear ring. The ear ring is bigger of course. Then she gets his little wee wee a little harder and then shows how her finger is bigger than his little penis. Then the one I didnt expect she puts Jacks penis in her mouth to show he cant gag her and then talking with his penis in her mouth it's so funny. She berates him and makes fun of him the whole time.Then eventually Jack pops his small load in her hand. We are starting the year off with a fun one. Since this is the first clip of the new year, we are taking four dollars off this clip, enjoy!!!

A dominatrix girl and a tiny cock 08/28/2009
We were at a hotel and they were having a fetish convention. I met this really cool Domme. I found out we had something in common we liked to make fun of small pathetic penises. She came over in a vinyl dress with a surprise underneath it. She teases Jack's small penis getting him hard and not allowing him to cum. She strokes it, slaps it while making fun of it all of the time. Then its surprise time, she pulls out her strap out from underneath her dress and compares it to Jacks small penis. Guess who wins?

Ebony girl making fun of a small penis 08/28/2009
I had my girlfriend, who I've known since college, come over. I told her I had a surprise for her. Her boyfriend has a large thick cock and she always tells me how a large cock fills her up. You can imagine her surprise to see Jack. The minute she took the towel off she said, "This is a prank right? I cant even fucking see it." She starts on how small it is and calls it mini cock. She thought Jacks penis was a pimple and said he has the most teeny dick she has ever seen. She couldn't even feel it in her hand it was so small. She jerked it and complained about the size of his penis while she laughed. Then she got bored and told Jack to hurry up. Then she told him she doesn't know how to get off little dicks...only big ones and then she made him stroke it himself. She kept saying how it was a little pathetic cock and told Jack sternly to jack his pathetic little cock. After saying that Jack immediately came so fast I didnt see it. She got right up into the camera and said, "You're missing it because it's sooooooo small." This was a good one

Cute brunette making fun of a small penis 08/28/2009
My friend Faith is a true southern belle, who never saw a penis as small as Jack's.Watch her laugh, try her two handed jerk technique on Jack. There is too much hand and not enough Jack. She eventually loses her patience with Jack and belittles him on how this isnt really a man's cock and if he doesnt come she is going fuck him like a girl. That got him cumming.

Cute bikini girl and a teenie tiny dick 08/28/2009
We are on vacation and I got bored. So I figured time for Jack's daily humiliation. So there was this young girl, who just turned 20 hanging out by the pool. I said you want to see something different and she said sure. She came up to our room for her surprise, Jack's small penis under a towel.She starts by chanting torture,torture, torture. She really enjoyed making fun of jack's small penis, showing how her finger was bigger. She kept going and laughing at him. Then was getting bored jerking jack's little little penis and was chanting about Jack's little penis.Then she shocked me she told Jack hold out your hand and jerk it. Jack's hand is so much bigger than his little little dick. This is a fun one.

A hot neighbor with huge tits and a tiny dick 08/28/2009
Yesterday was one of the rare times my neighbor Elle was home. She is a very hot milf and she is a big cock lover. So I told her I had a surprise for her and it was time to laugh at Jack. She was shocked his penis was so small and made fun of it the whole time she was jerking him. She has huge tits and she compares his little penis to them, of course they are nothing in comparison to jack little wee wee, it's so funny watching Jack just laying there getting humiliated by this sexy milf.

Girl with a great body humiliating a tiny dick 08/28/2009
My friend was out on spring break, I know some of guys she has dated. She loves huge cocks, the bigger, the thicker, the better. So I surprised her with little jack. She said her little finger was bigger than Jacks small penis. She laughed while stroking Jacks little penis comparing it to her thumb and if she had dated Jack the moment she saw his little penis she would of been gone LOL. After he came she couldn't wait to leave and as she left she said bye little cock. I have to remind her something that small could never be called a cock.

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