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KaseyLegs 58M
0 posts
5/19/2022 6:54 am
The fantasy gone sideways


About a year after I ended things with Mike and Bob, telling them I was done with the whole thing forever, I started flirting with the idea of meeting someone new. Those men I did meet just didn't work out. Either they were creepy, or they were too nice. They would defer to me when I tried to back out of going down on them. What I needed was someone like Mike who would glare at me and tell me to shut up and get on my knees.

The two things that excited me most, sexually and otherwise, was the threat of exposure, which was why I was so<b> obsessed </font></b>with wearing short shorts when I went places, and humiliation. Specifically, humiliation related to how I dressed in "girl clothes" and humiliation.

Mike talked down to me like I was a or a pet. That turned me on. The "nice guys" who talked to me like a friend, or someone who was genuinely concerned about me, turned me off. Mike would get me to the point where I couldn't handle it anymore. It became so intense that it would eventually lead me to stop.

Mike said, "You love sucking cock, but you hate being a cocksucker." It was like an enigma. If I had been interested in more from men, a relationship on some level, I probably would have come out. I wasn't dating men or pursuing romance. I was arranging to meet men, dress up in a skirt and heels for them, let them have their way with me.

One time, Mike came over and I was really anxious. An old friend was in town and there was a chance they would visit. That left me uneasy about having Mike at my place and I was reluctant to get into anything with him.

And then he said the magic words, "Stop being ridiculous. You're a natural born cocksucker. Get on your knees."

In 2005, after a dozen or so meetings that just weren't right, I ran into an ex-girlfriend who was in town. We arranged to have lunch, then ended up having dinner together the next day. We got back together, deciding we should give it another try as we'd been young when we originally were together.

Erica asked about my legs and why I shaved them. My usual excuses sounded lame in the context. I decided to tell her that I occasionally crossdressed.

Her first question was, "Have you ever been with a guy while dressed like that?"

Pretending I was confused by the question, trying to act like the whole idea was lost on me, I told her, "Men have seen me dressed, why?"

She went on to say that ever since she saw my outfits, she'd been imagining and fantasizing about watching me go down on a man. we kept coming back to it. She was big on the idea and trying to find just the right guy.

When she found a potential candidate a couple weeks later, she told me she wanted us all to talk first, see if it felt comfortable. The more she talked about it, the more I fidgeted.

The truth was bothering me. And I kept thinking that if I did this, there was no way that either Erica or the man would believe that I'd never done it before.

So, I blitzed her with the truth. Admitted that I'd "experimented" with men during the summer of 2000.

Erica stared at me, cold-faced, as I told the story. When I was done, she shook her head and said, "I'm going to have to think about this and whether I want to be in this relationship with you."

I asked her what difference it made, since she wanted to see me go down on a man anyway.

With a sigh, she told me that the fantasy was related to putting me in an uncomfortable position and seeing what happened. Now, she said, I would be looking forward to it rather than feeling anxious about its arrival.

The next day, she broke up with me after talking with her friends and soliciting advice, which meant they knew. And it wouldn't take long for something like that to make the gossip halls.

People I was friendly with began giving me the cold shoulder. It was humiliating, and not the kind that I found sexually explosive. All I could think of was people who knew me finding out about my extracurricular activities and where that would lead.

As soon as I could find a place, I moved out. After the move was complete, I never heard from Erica again.

I felt incredibly stupid. I'd misunderstood the nature of Erica's fantasy. I'd conflated it with my own. And I'd begun imagining having my cake and eating it to, as I believed that Erica would be open to me occasionally hooking up with men.

I would never have a real girlfriend again. I would date, pursue women, but I'd try to keep them from wanting to get involved with me rather than trying to seduce them. It wasn't that I didn't want a girlfriend, I did, but when I tried to imagine a scenario where my girlfriend found out about my secret life, I saw Erica's face, the surprise and disgust, as I told her about the summer of 2000.

I would move to another town a month later. After running into one of Erica's friends at the supermarket, and having her ask me, "Erica told me you were with two guys at the same time a couple of times? Is that really true?"

I couldn't bear it. I'd kept this side of me a secret, at first because I didn't think anyone would understand, and then because of how I became when I was with a dominant man, losing my self-esteem and getting into a mindset of doing whatever I could to please "my man." I tried to hide it, but if I went on seeing men regularly for an extended period of time, it would start leaking into my regular life.

I worked a job where I had to be on the phone a lot, getting answers or information out of people. Towards the end of the summer of 2000, I'd become timid at work, soft-spoken, and would go out of my way to avoid offending someone.

At first, that part of me only emerged during the actual "session." But then it seemed to take over my entire personality. People were noticing. Asking if I was feeling okay.

Two things happen after a long period of time hooking up with a man or men. I gradually become more and more submissive, eager to please, and start deferring to every other guy in the room for help or answers.

Because of Erica talking to her friends, claiming they'd keep my secret, and then how word started to leak out, I distanced myself from my friends. Nothing horrified me as much as having a male friend I had known for many years asking me if the story was true.

And then what was I going to tell him? Yeah, I like being on my knees in front of other men?

I moved to a town almost an hour away and started keeping a low profile. And I was on an island, sailing alone.

And as the months went by, it wasn't just my longing to dress for men, to show off my legs in public. It was also loneliness and boredom. And that was a heck of a good "in" for someone who wanted to bring out the submissive side of me.


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