*Custom clip, No names used

You are wearing any top and pants you like, whatever you think looks good and sexy on you, plus ankle boots and some cute socks.

It is time for you to humiliate me again. This time you will describe what a date looks like for me. A loser date.

Alpha guys date hot girls to have fun and to have sex. Not me. I want it so badly, but this is not how my dates turn out.

Today you will describe my dating, and I will masturbate when I watch you. I have not deserved to see you in underwear. I will listen to you and jerk off looking at your socks. This is all I get. And no cumming before you give permission.

You take off your ankle boots.

I connect with a girl on a dating app. My looks are ok, I have a decent job. When we chat, she is more hesitant. I am insecure, eager to please. But after several requests, she agrees to a date. What does she have to lose? It will be a nice dinner, maybe it will be fun?

We meet up. I give her flowers. We go to a restaurant. I might look ok, but I don’t have the confident posture. She is not able to see that I have a small dick, but she can feel it.

I am awkward. Nervous. Excited. Is she wearing a dress? A skirt? Heels? Pantyhose? Lipstick?

When we talk, I keep wondering what she is wearing underneath. Silky panties? A thong? A lace bra?

I will never know. I try to tell myself, maybe this time will be different. Maybe she will want a second date. Maybe she will come home with me. Maybe we will eventually have sex.

No. I know how this will end. You are laughing.

I am a loser. I have a small dick. I know I am sexually inept. If I got in bed with her, I would not be able to get an erection. She can feel it. She is already planning to end the date.

I am jerking my little dick looking at your socks. Is it starting to get hard? Does it turn me on to be reminded that I am a loser and sexual reject? You laugh.

She does not want desert. No coffee. She needs to go. She needs to get up early in the morning.

Yeah, right...

I pay. Of course. On the way out, I ask if she wants to meet again. She says no. She does not feel that way. But we can be friends. You laugh, so much!

I lean forward, to kiss her on the cheek, but she turns away, and leaves.

Another date is over. And it ends the same way it always does. I go home. Alone. Disappointed. Frustrated. Horny. My little penis is throbbing. Untouched and unwanted. But...I have my hand (you show with your hand).

You humiliate me, show me how to jerk off, tell me how pathetic I am and how stupid I look. This is what I can get. Masturbate my small dick and look at your socks. You make me say I am a loser, I will always be rejected, and make me thank you for letting me see your socks and jerk off. You guide me to a pathetic orgasm and laugh.

Losers' Date-Psychological Loser MindFuck (720p)