ESM 39 “Duped by a Sissy” (Excerpt)

2013-02-03 00.05.31

Fiction By Miss Ivy Ohmigosh


I took a big chance that Friday night when I wore panties around Erica, but I did it for a reason. I didn’t want to go back on my decision to break up with her; I didn’t want her to convince me to go to bed with her, and I figured if I wore panties under my male clothes, then I would make sure I couldn’t be talked out of my plan for a more honest future. Erica didn’t know about my crossdressing or sissy interests, and I initially thought I would keep it that way.

I stood there in my living room while she yelled at me.

“I don’t understand, Jim, just run this by me one more time. You want to back out of our trip next week? With all the deposits and tickets and everything paid for?”

“You’re not going to lose anything,” I said quietly. “I was going to pick up the tab, remember?”

“But that’s not the whole point, Jim. We’ve been hanging out together for seven months…things have been smooth…I just want to know why you’re backing out!”

“I can’t go on vacation with you, Erica, this relationship is just not working for me. It’s not you, it’s me! I’ve just been doing some heavy introspection lately and I’ve realized I’m not ready for anything now…not even what we have, friends with benefits free to date others, friends who go on vacation with each other but have no real strings attached.”

What I didn’t tell her was that I had realized my sissy desires were so strong that it wasn’t fair that I date her anymore. I didn’t want to share my secret—or so I thought; but at least I could bask in my feeling of “integrity” by not leading her on anymore, and making her think that I was just another “vanilla” guy.

Erica crossed her arms and stood her ground. “Jim, before I leave this apartment, you are going to tell me what’s behind this sudden change of heart. I’m not leaving without a complete explanation.”

Erica was a very imposing female, and even more so when it was to her advantage. She was always gorgeously made up with a lustrous mane of hair, beautifully dressed in stunning outfits, and most often in the highest and most fashionable heels. Working as a realtor, she was high-powered and persuasive; qualities I found both attractive and intimidating at the same time.

I didn’t have problems meeting successful, driven women like Erica; I was a good looking guy, wellspoken, and a successful executive in a large digital media company. But what I suddenly realized as our argument raged was that Erica did not like anybody breaking up with her; it always had to be the other way around, even if the affair was casual. No matter that she was also dating another guy named Tony, fucking him when she wasn’t with me; she didn’t want to be the one told to take a hike.

When I didn’t say anything, Erica changed her approach. She walked over and put her hands on my arms. My heart pounded mercilessly because not for a single moment did I forget the panties under my trousers, and I was frightened that Erica was going to try to seduce me out of my resolve by rubbing my crotch and discovering that I wasn’t wearing my usual cotton boxer shorts, but tight lacy nylon panties. Well, hadn’t I worn this underwear to give myself the backbone to say no to her and refuse any possible attempt to drag me into bed? Now I realized I had taken a terrible chance. I might not succeed in keeping her out of my slacks and my secret sissy life might be out before I was ready to reveal it to anyone.

“What’s the matter with you, Jim?” she said, “you feel so tense, like you’re afraid of me touching you. What’s happened?” She suddenly sounded more worried than angry, and that was natural too—because she liked me, and up until then I had been a very predictable sort of decent, dependable boyfriend.

I inched away and sat down at my desk, near my laptop. Erica’s eyes were on me the whole time, as if she were observing me scientifically, or strategically. Well, she had to think that way to be successful selling real estate these days, and I think she now started thinking of me as yet another problem to be solved—like trying to find ways to convince a wary buyer that a particular condo was too good an investment to pass up.

I felt myself sitting in a strangely passive posture, with my knees together and my hands in my lap, like I was a young girl wearing a dress trying to prevent anybody from looking underneath it. I could feel my cock and balls squeezed tight in the narrow crotch panel of the panties. I could also feel the pre-cum…yes, heaven help me, I was aroused by my fear of exposure and yet I had taken a tremendous risk in wearing the panties.

Maybe I wanted to confess everything to Erica? Maybe I was setting myself up for it?

But Erica’s moods changed with the passing moments. She went from concern to imperiousness again. With her bright crimson-manicured fingerson her hips, she walked toward me until she was only inches away. I couldn’t quite face her, so she lifted my chin with a forefinger until I would meet her eyes.

“What is this all about, Jim? You’re not going to make a fool out of me, and screw up my well-needed vacation, without coming clean.” She stared into my eyes so fiercely it almost seemed she could be a hypnotist.

I couldn’t tell her…I couldn’t…I couldn’t!

“Come on, Jimmy,” she said tenderly, fully aware that when she spoke to me that way, calling me “Jimmy,” I was more easily manipulated. In the past, she had used that tactic to convince me to do things like try a restaurant I didn’t particularly like, or see a movie that didn’t appeal to me.

“Jimmy, I’m worried about you…what is this all about?” She bent down, held my shoulders, and looked into my face like a teacher trying to aid a promising student stunted by some heavy personal problem at home.

Should I tell her? I thought. Should I? Suddenly it occurred to me that maybe I wanted to…maybe I’d been fooling myself all along, just as I had fooled myself about being a “regular” guy. Or fooled myself that I wore the panties to keep Erica away, when maybe what I wanted to do was have some tangible proof to show her of what was going on with me…concrete nylon proof that I was a panty-craving crossdresser (or to be completely honest, a frill-hungry sissy). Maybe I wanted to demonstrate visually how these desires had overtaken my consciousness, and how it would be a miserable lie to pretend otherwise! Maybe I wanted Erica to be the first person to see what I was really like!


(Continued in Chapter 2)




This entry was posted in Fiction.