As requested Mistress is having me write a story about a guy tricked into becoming a sissy while wearing panties as a gag and my pink butt plug...here goes...
My hands are tied behind me in the chair and I am blindfolded and gagged with my own cum stained panties. I can feel the butt plug filling me and the soft breeze of the fan blowing over my stockinged legs. My cock, locked in chastity, strains at its unfamiliar surroundings and I let out a small whimper.
I guess this is what I deserved.
It all started with a simple online romance. Nothing big, no weirdness. I just wanted a companion, maybe try out a couple dates and see where it led from there. She was beautiful, smart, attractive, had a nice job, and was quite friendly with me. Maybe she was almost too easy of a catch. I thought I had things made. We went out to dinner a few times, had a couple fun evenings, but nothing especially out of the ordinary. She was hesitant about getting more physical with me but I just figured she had gotten out of a bad relationship and wanted some space and time. Little did I know.
Things started to change a little when she asked me to shape my eyebrows. It seemed like an out of the blue request, but who was I to deny her. She said she just wanted them cleaned up a little, that it was a pet peeve, she didn't like hair, and liked a neat looking guy. So I went along with it, even when her friend at the salon seemed to get a little carried away with the arch. She laughed and said it framed my eyes well. I got a long kiss for that one, and forgot my worries right away.
My facial hair was next to go, I did that without her asking. I figured she didn't like bushy brows, so why should she like a beard? I was right, she responded favorably. An amorous session of feeling on her couch seemed to be my reward for good behavior. While kissing me she suggested that I should simply take care of the rest of my "beastly" traits as she called them.
So like a fool, I complied. Down the drain went my leg hair. Smooth and (so I thought) sexy for her, I returned and once again was greeted with praise and some amorous advances. We had a wonderful meal and a bottle of wine and then I began to feel a little dizzy. When I woke up I was here. Plug in my butt, dressed in women's clothing, made up like a slut, and tied to a chair. She sat in front of me on her couch, relaxed and sipping a wine glass. I made a sound in my panty gag, but she just smiled and ignored my plea to remove it.
"Well, well. I am sure you are a little confused. No matter. Yes, I did drug you to get you into this position, but it was for your own good. I didn't want to have to work any harder than I had to and I figured I would at least let you have the dignity of a choice. I know your fantasies. I checked through your online history when we were over at your house the other day. You want to be a sissy, and I can help you. I've already quickly molded you into the perfect girl, smooth and service oriented. You are so eager to please me, so willing to obey my commands. I want you to be my new sissy maid and you will start tonight. I have the key to your chastity belt and have invited a party of my friends over for cocktails. You will be serving us all...if you choose. Of course that choice is up to you. I took the liberty of dressing you in your own sissy things, I hope I picked a good outfit, I think you look great in it and I am sure you will do a fine job...but that is up to you. I will leave for an hour. The key to the chastity belt is on the table. Your ties are loose, simply slip out and leave. You'll have to trot home in your sissy things, but you are free to go...
However, you may also simply stay in waiting. If you do, you will be my sissy slave. You will do as I ask, you will never be a man again...not that you ever were...and you will please me in every way I demand. It is all up to you."
With that she stood up and set the key on the table.
I sat there, thinking for a moment.
Could I turn down this woman?
Could I deny my feelings?
She tricked me so completely into thinking I was simply a nice guy she would want to date.
And now to be her slave?
The clock ticked.
I didn't move.
The footsteps came up the staircase. I blushed in fear and eagerness. I was to be her sissy.
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