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skip to main skip to sidebar Sissy Humiliation. Thursday, August 7, Nashville. Get ready, bitch I had met a lady online named Anna. She was a little older than me and lived in a Nashville, which is about five hours from where I live. She was part of a group that did a little swinging, and while she had encountered other sissies online, she'd never really met any in person, and she was a little intrigued by it.
We talked on the phone a couple times, and I told her some of the things I did.
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She thought it was pretty funny and she wanted to meet me so I made plans to visit. Once I checked into a hotel and got acquainted with Anna for awhile, I checked into local adult entertainment in the phone book.
I've utilized the services of escort girls to come to my room and engage in some sissy humiliation sessions with me before, and we thought it might be fun if I had one come over to do a session with Anna present to just watch. I called one of the services and told them I was a crossdresser looking for some light domination.
A woman named Kathy called me back and I told her I had a female friend who just wanted to watch while she dominated me. We agreed on a price, and she headed over. I showed Anna some of my sissy outfits and modeled some of them while she giggled at me and called me a "sissy cunt" in her sweet southern voice.
I was dressed in my bra, pantyhose and high heels when Kathy knocked on the door.
I covered myself and let her in. Kathy was very pretty and very nice and professional. We worked out some financial issues, I explained exactly what it was I wanted, and she called in to the service to check in. Kathy was wearing a skirt with pantyhose and no panties as I requested. I was behind her peeking up her skirt, and Anna was sitting in the corner, giggling, calling me a naughty boy.
About that time, Kathy hung up the phone and turned around, catching me. Get up! What are you doing in these clothes? She was quite serious. I was like a little boy caught being naughty.
to see what they felt like? You wanted to feel what it was like to be a girl? Is that it? You want to be a girl? She quickly grabbed me hard by the wrist. C'mere" She marched me over to the bed, sat down, quickly yanked my pantyhose down, and pulled me over her lap.
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Then she started smacking my bottom She quietly and sternly commanded, "Put your hand down. She would alternate from cheek to cheek. Anna later told me she couldn't believe how red my bottom had become. I'd never been spanked this hard.
Change of clothes "Now get up! I took off my heels, pantyhose, and bra. I was rubbing my bottom with both hands. She again grabbed me by the wrist and marched me across the room. Let's make you into a fuckin' girl and you can really see what it feels like. Kathy told me to shut up while she put a black padded bra and thong panty on me.
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Next came a black, boned waist cincher with garter. Then she had me sit on the edge of the bed while she put black stockings on my legs. The whole time she was telling me what a hot girl I'd make and how I evidently like wearing girls clothes or I wouldn't have such a hardon.
I tried to deny it, whimpering like a pussy boy.
Finally she put my 5" stiletto patent leather pumps on me and had me stand. I stood and covered my bra with crossed arms like a woman would if she had been suddenly discovered undressed.
This infuriated Kathy, "Put your hands down! You wanna be a girl. Let's see you be a fuckin' girl. Walk around for us, bitch.
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Kathy looked over at Anna. Do you think he likes being a girl? Round two Again, Kathy grabbed me by the wrist like a child and pulled me across the room, sat down and put me back across her lap.
I was already smarting from the first assault on my red ass, and I didn't think I could tolerate much more. Before she even started, I was trying to cover my bottom.
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She repeatedly ordered me to put my hands down as she started over and over. It only made it worse. Kathy spanked and spanked harder than the first time.
It hurt like hell. I looked over helplessly at Anna, "Please help me.
Make her stop! I won't! Kathy answered, "You want me to spank you again? Anna just started laughing, "I don't believe this!
You are a fuckin' sissy cocksucker!
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She had me lick the balls and lick up and down the shaft. I was stroking myself as I did. And now, your sissy ass With that, Kathy took the butt plug laying on the bed and started squirting it with KY jelly and told me to turn over on the bed.
I'm really sorry. I won't do it anymore! Anna jumped in, "He wishes he was a real woman so he could take a real dick inside him. Kathy again told me calmly to turn over as she held the greased up plug in her hand.
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