I did some pretty crazy and bad things after high school. I worked in a four story building that had realtors and escrow officers and upstairs was a plastic surgeon. When I was in high school I was turned on by not porn, but real pics of before and after shots of women who had breast surgery and work to their thighs and butts. I made friends with the woman who was at the front desk, stole her keys for an hour and duplicated them. I would break in every week and get into the drawer with the memory chip that had the pics they would take of their patients, and copy it to my camera, and use it for my spank bank.
After time I got to thinking how I was privately humiliating the women I got to see. Most of the pics didn't show their faces, but I didn't care. A lot did, even full frontal pics, head to toe nude. I thought how humiliating it had to be for them to have to pose for them. I did this for 2 years straight until I moved away and got another job. I obsessed about the pics. They were pretty complete. Even if a woman went for their "flank" area or something else, it seemed they had to be topless. I laughed to myself over how they became this doctor, and maybe other people who worked with him, private centerfold show. And it would last forever.
Eventually the excitement and fantasies i built up over their humiliation got as exciting as seeing them nude. I dwelled on the humiliation in my mind, and wondered what it would be like to be sexually humiliated. That went on for 2 years and 2 girlfriends and 3 fuck buddies and I never shared that with them.
I've been with this girl since the summer, and in October we were talking after sex and she asked me what my darkest fantasy was. So I gave in to telling her the truth, and she laughed and said I couldn't take "real" humiliation. I told her I could. It almost came out as a dare. I said yes, but that it had to stay "with in her bedroom only, and no cameras." She said okay,
Two nights later she told me she was going to humiliate me and that was I still up for it? She said she would really do a number on me, and that I would be totally humiliated by it. I still said yes, but she had got me worried.
Two nights later we had a great date and she was a wild rabbit in bed, and we fucked like crazy. I didn't get how it could be humiliating, and thought she was going to put it off.
After the sex she told me it was time to really test how much humiliation I could stand, and told me I had to be tied up in my boxers to a heater pipe in her bedroom. I said yes, and she told me to wrap a towel around my waste also. I admit I thought I probably looked stupid. Tied with my hands behind my back and in a towel, looking at the bed. I thought she was going to humiliate me by masturbating in front of me, with me not being able to do anything about it.
"Ready for your humiliation?" I replied yes, and kind of laughed. She made a text on her cell, and a few seconds later there was a knock on her bedroom door. She opened it and in walked a guy. "This is my boyfriend from a year ago. I hope you enjoy your first humiliation." Before I could think of the word "first", the two of them began to kiss and then undress each other, and then perform 69. I was way beyond shocked. Occasionally the guy looked at me and smiled, and while giving him oral, she would say great things about how big his dick was. When they moved on to full sex, she shouted in ways as he entered her that she never did for me, and as he pounded her she was full on screaming. She shouted out about how much of a man he was, and came like a banshee.
I had a lot of thoughts about all of this, including how exciting it was to see my girl get worked by this guy. But it was humiliating, hearing her voice and screams.
Afterward, she told Jim (his name) to sit down for a moment. Then she said to me, "Well, it's obvious who the real man is here." I was deeply shamed, and she continued: "Since it's not you (she was looking at me), I don't think you need a man's underwear." She dropped my towel and pulled down and off my boxers, and I was standing there with a shrimp of a penis next to this guy who had the sheets over what I had already leanred was a pretty large penis.
"Now, let's put you in something more appropriate." And she took out a pair of pink panties from her dresser and dressed me in them, and there was nothing I could do about it. She wrapped the towel around me, and put on her robe, and made another text. In came her closest friend, Cathy, and she said she could hear from the other room that I had gone through with it. Deborah (my girl) said Jim had split her like a log, and that I got a front row seat. Deb just looked at me and laughed and pitied me.
Deb said it was time for my final humiliation, and that she was saving the best for last. She dropped my towel, and it was obviuis that Cathy wasn't let in on my being redressed in panties. She looked at me and wouldn't stop laughing. "Is there anything in there?" Cathy looked down at my crotch. "Oh, I'll show you." I tried to take a moment to prepare, but Deb just pulled the panties down, and said, "Let's leave them at your ankles."
Cathy stood there laughing at the size of my penis, pointing, and showing off her pinky to mean I was small. "That is the smallest penis I've ever seen!"
Deb said, "No kidding." Jim laughed, and I stood there humiliated.
The others left and Deb untied me.
I didn't have the guts to call Deb for 3 days. When I finally did, I told her that it took me a while to get over it, and that I probably wasn't over it. I also said that it somehow turned me on. Not her having sex with her old boyfriend, but my humiliation.
The next time we got together she didn't tell me, but Cathy was there when I got there. Together we talked about it, and Cathy also said she really enjoyed it, and both of them told me how I reacted to all of it. Cathy also said that, yeah, I was really small. Also, she did get turned on knowing what I looked like naked.
We can't do this again, and I really don't want her fucking other guys over and over, but I have to accept that what happened to me was very enjoyable. Being laughed at while it happened was a terrible humiliation, but since it happened, all of my fantasies revolve around my being laughed at by Deb and Cathy. Cathy's called me shrip-dick a few times, and Deb refers to my penis as a dicklet, or baby penis. I also enjoyed being stripped of her panties as icing on the cake, and that's also got me excited. She says she'll play like this again with me, but I don't know what to do about it. I've wanted to fuck Cathy since I met her, and never getting to see her naked while she knows everything about my body is a turn on.