Fiction by Miss Ivy Omigosh

Chapter 1

Μy name is Brian. Or it was Brian…I guess I’ll be called Brianna soon, and probably for all time!
Anyway, let’s start at the beginning. When I lost my job a few years ago at the height of the so-called Great Recession, I quickly got mired in hours of wasteful resume-emailing. When job interviews, much less offers, didn’t come through, I spent more and more time surfing the Web and looking at my favorite kind of porn: shemale pictures and videos. All I thought about was how amazing t-girls look, how feminine, how alluring—and how much I wanted to suck their cocks and get fucked by them. I began to neglect my job search and just sat around surfing and stroking. It was an unfulfilled fantasy, being with shemales, and with all the time I had on my hands, it began to take over my mind.
But it wasn’t until I met Gwen that I started to think I wanted to be a t-girl myself…or at least a sissy.

It happened like this. One night I decided to take a shower, shave, get dressed, and go out to a bar just to get out of the house and away from all the porn and masturbating. I decided I’d spend a little time in the “normal” life I’d had before my transgender fantasies had gotten such a grip on me. When I had a job, I used to date “genetic” girls (GGs), or go to strip clubs and get lap dances, just plain ole vanilla straight stuff. But the isolation I’d fallen into since losing my job had shifted me so thoroughly away from the person I used to be that I felt as lost in my fantasies as I felt excited and enticed by them.

In the back of my mind, though, I was thinking maybe I’d get myself a little drunk at a straight bar first, and finally work up the nerve to pick up a t-girl at one of the shemale bars on the edge of town. Because really, I was only fooling myself, thinking that I’d meet some GG in a cocktail lounge and take her home and fuck her! You see, I was never much of a cocksman to begin with. My tiny organ had assured that. My corporate office job had been doubly important because it gave me the only sense of mastery and even masculinity I had. Without it, I shifted into my daydream world of men turning into women—no, not women, exactly, I’m not being totally truthful here; but men turning into sissies who only wanted to dress up and flounce around like silly, helpless, small-cocked creatures.
I was overwhelmed by all these perverted thoughts and had to get away from them for a while. So I forced myself into my old “normal” mode and walked around for a while until I found a bar that looked lively and promising. Maybe, I thought, I’ll find a girl who’ll put up with my small penis and make me forget what I really want.
I never imagined I’d meet a woman like Gwen there.

She enveloped my meat in her hand and stroked it while kissing me masterfully, pressing me back against the bed as her tongue penetrated my mouth and her fingers pulled on my meager inches slowly but with strength and purpose.

She ran her scarlet-manicured fingers over the tip of my nub, then grasped the little shaft and began stroking

I’m a middle-aged guy, although thanks to good genes I look younger than I actually am. Gwen was like that too—I think she was in her forties, but could easily pass for ten years younger. So we were about the same age, but there was an air of sophistication about her that made me “feel” much younger than she. She sat down at the bar and, after I got her attention with a few remarks about the retro jukebox, I offered to buy her a drink.

She was dressed chic more in the way of a woman from the 1960s than now, in a jacket, blouse, pencil skirt, and medium-heeled pumps. She carried herself with class and in her eyes there was a kind of amusement at everything going on around her. I was excited by her presence. We moved to a booth in the back and the conversation immediately got more intimate.
“What’s bothering you, Brian? You have this dejected air.”
“I thought I was being rather jolly,” I said.
“That’s how I picked up the dejection. You were forcing the jolliness.”
It was as if she were pressing a button that needed pressing. It turned out she worked in some kind of corporate psychological think tank, and was well aware of how people send out cues. Something about her—maybe the dark waves of her hair, or her blue eyes looking directly into me, or the way she lightly fingered her simple pearl necklace—made me want to confide in her. I didn’t tell her the big stuff—the kinky stuff—the fantasies about sucking off t-girls or daydreams about being made into a girl or sissy myself; but I got into my worries about looking for work, and feeling inadequate and isolated because of it. Although it seemed as if she were inviting me to indulge in self-pity, it didn’t seem like a bad thing to do around her.
When I was done with my litany of woes, however, I didn’t feel the relief I had been hoping for. I was angry at myself for probably blowing a chance with Gwen on the more normal level, of having a few laughs, of maybe going back to her place or mine and having a little fun.
I felt more mixed up than ever.
Gwen put her hand on mine. “That’s okay, Brian, I know you needed to let it all out, and I’m honored you let it out for me.”
“No, it was for me, I’m sorry for myself and I’m probably boring the hell out of you.”
“I disagree, darling.” I felt a tingle when she used the word “darling.” I liked it because it suddenly felt as if she were assuming some kind of power over me with that single word and her tender attitude. “You let it out for me too, Brian, because you wanted to let me know that you trust me and want to be with me.”
“Be with you…?”
“You’re hurting, and it would make me feel good to help you feel better.”
I almost laughed out loud at the irony of it, but I checked myself and merely nodded. In the end it looked as if my “pity party” approach had worked! Maybe I was going to get laid after all! And with her warm personality, Gwen probably wouldn’t laugh at my penis as so many women had done in the past. She would probably make the best of it.

Read the rest of the story in Enslaved Sissies & Maids 36

Enslaved 36

Enslaved 36