Mini Virgins Epic Fail
This clip is similar to: "Prom Night Small Penis Humiliation". It's your first time. You get to make out with a hot girl. You get to go down on her. It's time to put your penis in, and you do it! Yah porn star! But she keeps telling you that's it's okay to put it in...she can't feel it. Ooooh, SO humiliating. Yup, it's IN. She finally gets a look at your inadequate equipment and decides maybe it's best if you just jerk off while looking at her pussy...but then, as if it could get any worse, you prematurely ejaculate. She tries to be kind but that almost makes it worse. It's the most humiliating experience of your life. You're a complete sexual failure.
Length: 9 minutes
New Virgin Cuckold
Custom vid for Ryan, his name is mentioned throughout You're soon turning 34 & still a virgin. You've always wanted to be with an older, more experienced woman but you were too under-endowed, a quick cummer & a chronic masturbator. Now you figure the closest you're going to get to sex is to be my cuckold. You've never seen sex up close though so I decide to work you into it slowly. I just tease you & get you to help put my lovers condom on. Then I blindfold you & let you listen to us having sex. When I take the condom off you're told to help me remove the condom full of his cum. The whole thing is pretty humiliating for you...but you like it. Then I tell you that if you want to continue to be my cuckold you're going to have to graduate from condom placer to cock fluffer.
Length: 10 minutes
Virgin Cuckolding Humiliation
Custom vid, no name mentioned: "My idea would be that the video starts out in a 'dream' where I am finally losing my virginity to you. You're letting me make love to you, who I've always lusted after and it's so amazing! But, it's not too long before you are waking me up back to reality and I'm face to face with you and caught red handed, day-dreaming and stroking with your silky panties around my virgin cock! You were about to go out on a date with a real man and you'd left me for just a few minutes, to get ready and I'm stroking furiously away. This will certainly not do ;) You force me to stroke for you whilst you humiliate me that you need to go out on dates to get satisfaction. So please may you add lots of cruel teasing that you are sooo good at and stroking your little finger in front of me? You make me cream your panties and force them into my mouth, before finally leaving me, spent and waiting to hear of your cuckolding stories when you come back from your date...."
Length: 13 minutes
Virgin Humiliation JOI
Custom vid (no name mentioned): What would be more humiliating than having your hot **** talk to you about sex? How about her figuring out that you're a virgin and giving you a hard time about it? It gets worse: she feels sorry for you and also wants to check that your equipment is working so she instructs you to masturbate in front of her! Whoa!
Length: 13 minutes