"I have a thought experiment for you, Jerkboy."
Suzette, my wife's sister, had me giving her a pedicure in my panties over at her beachside apartment. It was her night, after my wife had decided upon a weekly loan arrangement. Her mom had me on Saturday for overnights. Someone else was having my wife, probably, although she usually preferred not to make it obvious.
The gal's big feet were nasty. A season of beach volleyball in hot, dirty sand did ugly things. I ground at her callouses while I listened.
"I have a group that meets once a month. We talk about female empowerment and positive outlook. Sometimes we have guest speakers."
That familiar hollow feeling returned to my stomach. My eyes stayed fixed on her feet.
"I suppose you wouldn't be doing much speaking." The Amazon laughed at me, knowing fear and dread she was creating.
"Seriously. It would be like performance art. The group could just -- meditate on the sight of a male abusing and degrading himself. They could objectify you, like you assholes do to us. Sort of a free-the-mind exercise. Hard to feel oppressed by the patriarchy if you see men as the jerkoffs that they are."
My penis began straining against the thin pink panty fabric. If she kept talking about it my cock would pop up above the waistband.
"Don't worry. You'll get to wear a mask or something. I can see you like the idea already." Suzette extended her other long leg downward and tapped under my scrotum, causing my erection to pop out. "Yup. Hopefully the group won't be too disappointed when they see it." She surfed for a movie to watch while I started on her toenails. I winced when I heard what she had picked out.
"I got this stick that goes into the TV that lets me stream from my phone. Can you hear it OK? I'll turn it up."
What I heard was my own grunts and shouts from her video of me being whipped with my own belt by Sarah's mother. It was a deep, deep hole I had climbed down into with Suzette. Hearing my voice crack and knowing I would soon break and beg and uncontrollably cry brought back the familiar dark fringe around the edge of my consciousness. I was there in her apartment, and I was there in Mrs. Landtree's living room at the same time, being beaten. And then I was nowhere.
"Ah. Such beautiful music. There you go! Bawling for us was so perfect. That was good for Mom, I think. Maybe the group could, you know. Take turns."
I blinked and saw a tear fall onto Suzette's big toe. Sadness nor shame nor humiliation nor even exhilaration could describe the rush that spread from my genitals up to my burning hot ears. My own sobbing echoed in my head when the clip ended. Another began after a few moments.
"Yeah. This one. Where you told us about how you got started."
My hands shook. I didn't remember very well what I had told them when they were abusing my sissyhole with that dildo and making me tell them stories to avoid the hurting. Suzette paused the video.
"Hey. Tell me more about Barbara."
When I was in law school, I had clerked for a progressive legal firm with a black, woman partner. She was tall and full-bodied, in her early 40's, and incredibly good-looking to me. Office gossip was that when she was younger she was thinner and a world-class stunner.
I hypnotically recalled to Suzette what had happened with Barbara.
She was assigned to be my mentor. It was a new thing for her, having a young male be her clerk and assistant. I was quickly infatuated with her beauty, Ivy-league poise, and especially her intelligence. Being subordinate to her caused strange things to happen in my head.
Instead of the usual Man and his Girl Friday dynamic, which was going on all over the firm, I started perceiving myself as Barbara's Boy Friday. It just seemed natural to be more like the many attractive young women working as legal secretaries and receptionists. Barbara was completely professional about it, yet she did notice my eagerness to please. Occasionally I would get a raised eyebrow or a hint of a smile out of her. It made me happy.
We had been going over a legal brief together and I could barely concentrate from her intoxicating perfume. While reaching for a yellow highlighter pen, her breast just lightly brushed my shoulder. Barbara's boob was well packed away inside a brassiere, I was sure. But still. I got an erection, and she noticed. My beautiful boss was called away to a meeting and told me to re-read and highlight the brief with my ideas, there in her office. Maybe because she didn't want me walking out of there with a boner showing in my pants. I don't know. She removed a scarf she was wearing, left it on her desk and left me there. And she closed the door behind her, which was odd.
Just a little tug, I thought. The scarf smelled of her perfume. I held it to my nose and that was it. I had to. My hand undid my pants, in front of her desk, back to the door, and I started rubbing my dick. Just an indulgence. When she left for these meetings she was always gone at least an hour. It would be okay. I underestimated the situation and got a little too exuberant.
Barbara walked in on me when my pants had slipped to my knees and I was really going at it. Came back for something, I guess. She nearly slammed the office door shut to make sure no one else saw what she did. I heard her lock it behind my back.
The return of my woman boss should have made me stop and yank my pants up, and I did feel a twinge of that. But I was getting close to coming. When Barbara walked in something flipped the other direction. Having her there with me melted right into my fantasy of being with her. The sound of the door locking was followed by the feeling of Barbara standing close behind me. I started beating off wildly.
When she ran her hand through my hair that was too much. I spurted and heaved and humped my hips in the chair for her. I either said "Barbara I love you" in my head or out of my mouth. As the dream of my orgasm subsided it was replaced with shame and embarrassment. Barbara could have been cruel or angry right then and things might have gone another way.
"I have to go back," she was all she said, quietly. Barbara walked around me and took a file folder from her credenza while I hung my head and stared at the cummy mess I had made. "Go clean yourself up before I unlock the door," she told me and then watched as I hobbled with my pants around my ankles into her private restroom.
"Yeah, yeah. There's a lot more to this," Suzette said as she adjusted herself to more comfortably offer her other foot for me to work on. "Get to the good parts." I fought through the embarrassment to tell more of my story.
Barbara gave me the lecture about sexual activity in the workplace, of course. I thought my internship was over but she said we would have to give an explanation, which complicated things. So instead, she had me draft a waiver agreement stating I wasn't being sexually harassed, in order to protect her and the firm. I basically signed my life over to her saying I agreed to do anything she wanted me to, I wasn't coerced, and I did it because I loved her.
My lawyer boss chuckled at the "love" part and made me change it to infatuation. She also added a clause indemnifying every other woman in the firm, just in case of a defamation problem, she said. I got a stern lecture about ever exposing myself or getting caught masturbating in front of anyone else, for they might claim I was sexually harassing them.
Before we signed and acknowledged, Barbara called in her favorite legal secretary, Carly, to notarize our signatures. The notary got a look at the single-page waiver when she signed her section of the document. My heart was thumping, let me tell you, from the idea that Barbara was agreeing to a sexual relationship with me -- and that Carly was going to know about it. Barb told her it was highly confidential and Carly nodded. The blonde shot me a sly look before she left the office.
"Well," my boss said as she sat back in her leather chair. "Let's see what we have to work with. Go lock the door, stand in front of my desk and drop your pants."
Just like that. Signed, sealed and delivered unto my woman superior. Waves of embarrassment rocked me as Barbara contemplated upon my naked penis and balls. She told me to play with it and get hard. I balked.
"Why not? You did it in front of me before."
It was an accident before. Being told to masturbate just standing there in Barbara's office was a reach, so to speak. When she said, mockingly, "Don't you love me?" I gave in and grabbed my penis. There was an electric jolt of humiliation at first, quickly followed by a rush of exhilaration. It only took a minute and I was achingly hard.
"Okay, stop and let me see it." It felt proud to present my erection to Barbara. She made the half-smile I had seen before, when she was trying to be patient with my law clerk stupidity. "That's not enough dick for me," said my Barbara, no differently than when I had been told to rewrite a legal brief. My heart sank. Then something weird happened. The humiliation aroused me so much, so surprisingly, that I spontaneously ejaculated, without even touching myself.
Barbara seemed amused. I felt horrified and ashamed. My penis stayed hard when I washed in her restroom. I took off my pants to avoid splashing water on them. While I was standing there using a hand towel to dry off, Barbara opened the door. I looked up and saw Carly with her hand over her mouth. She stared as I rubbed the towel on my genitals for what seemed like an hour, then finally told Barbara, "I thought you two were pranking me with that agreement."
I knew Carly was recently divorced. She was only a few years older than me, but a lot wiser about the practice of law and how to help Barbara. I thought she was attractive, in the horny librarian sort of way, yet she was just another flower in the field of attractive women who worked at the firm.
Barbara had me remove the rest of my clothes and kneel before the two of them leaning on the front of her desk. "I caught him masturbating to one of my scarves, here in this office, and I don't think it was an accident," she told Carly. "Just now, he did his little squirt and all I did was tell him to get it hard."
"Wow. Can you make him, you know, rub it some more?" My face was burning hot with embarrassment. This had gone way beyond anything I had imagined would happen.
"He should ask you if he can masturbate." Barbara looked into my eyes and said, "Would you like to? Ask her."
The rational part of my brain couldn't handle her question. Some thought bubbled up in the bowl of soup that was my mind and told me I wanted to beat off, because I liked the humiliation. I heard myself asking Carly, "Please, may I masturbate for you?"
The women's laughter made me afraid someone would come to office to see what was so funny. Then I realized I didn't care. Barbara was there. If she wanted me to disgrace myself in front of Carly, or whoever might knock on that locked door, it made me happy.
"This is incredible. You go right ahead with that," Carly told me. I hung my head in shame and started jerking my dick. "You know, I had a little crush on you. I thought maybe we could go out sometime. But this -- this is hilarious."
"Look up at her," Barbara said. "Isn't she lovely? Why don't you ask her out on a date?" I willed myself to face them despite the hollow pit in my stomach.
