Mistress Katja asked me at our last session to write a fantasy about a session with her and a transexual. I want to emphasize that this is a fantasy and nothing in this essay actually happened.
THIS IS A FANTASY
The facility that Mistress Katja uses for sessions with me is an old Quonset hut in a heavy industrial area. From the outside it looks awful-- rusty, old paint, and a tatty piece of paper hanging near the door "Ring bell for entry". One peculiarity is that the door opens outwards, and after I ring the bell, there’s often a wait, and then the door seems to simply open by itself. The reason for this rather creepy beginning is that Mistress is waiting inside, and doesn’t necessarily want to be seen from the street. Inside, it’s a different world, dim red lighting shows a fantasy land of bondage equipment, ropes hanging from the walls, several racks and chairs. There’s an old fashioned iron bed which looks like a relic from a catholic boarding school. A men’s urinal not connected to any plumbing but with a plastic pipe going down to about floor level. On my right as I walk in is the iron rack that Mistress prefers to whip me on, and I glance at it with a tinge of apprehension.
Mistress is waiting for me inside, wearing a long, heavy black satin robe, which gapes open to show its bright red lining and her red and black corset. Her hair is up, her beautiful and severe face is made up, her legs in hose ending in black high heels. So far, this is a normal beginning to a session with Mistress K. Our sessions have assumed a ritual flavor. First we stop and talk for a few minutes about my mental health, the state of my chastity device, and my general level of frustration. Then I take off my clothes and she ties me to the rack, and uses a variety of floggers and whips on me until I scream and cry. This period is followed by dress-up time, and then tease and denial time. But the point I’m making is that these sessions have always been just me and Mistress Katja. She has made references to my becoming a complete sissy and learning to suck cock, but I’ve come to think that they are only fantasies.
On this day, when I enter the dungeon, I see another woman, sitting on the couch in the rear. As Mistress greets me, I hear the other woman say – "So this is the sissy?" and I can tell from her voice that she is a transvestite or transsexual, although I can’t see her very well in the gloom.
Katja introduces me to Tiffany, who I can see better as she gets off the couch. She is short, with olive skin, and looks somewhat ethnic. She is wearing a black bustier with long thigh high boots. She is shorter than Mistress Katja, but taller than me in her heels. After I say hello, she says "Are you really ready for me sissy?" My mouth is dry and I simply mumble something.
Mistress Katja is all business, however. There is no chat, it’s a simple "get undressed.". Tiffany watches while I undress, and I have a moment of embarrassment as I pull down my panties, that are bright pink today. In a couple of minutes I’m in wrist and ankle cuffs and stretched out on the rack. Mistress Katja and Tiffany have a conversation about how much pain I can take. Katja points out how my erection is pressing against the steel of my chastity device and Tiffany giggles.
After my whipping had progressed to the point where I was squirming to get away from the lash, Tiffany asked Mistress Katja if she could try it. In a moment, Mistress Katja was on my left, and Tiffany on my right, and the blows fell first from one side and then the other. As I tried to pull my butt away from one blow, it ran into another blow from the other side. In only a few moments I was sobbing. I’m always humiliated when I start crying, but I think that Mistress Katja enjoys it.
But this time, I felt Tiffany’s arms hug me from behind. She whispered in my ear ‘Does it hurt little baby?". Her hands came around and pinched my nipples. I could feel her breasts on my back. Then her hand caressed my ass, and I felt one of her fingers search up between my ass cheeks and touch my rectum. I came back from all the pain and realized that today I might really become a sissy.
I was let down, and Mistress Katja had me dress in stockings, panties, heels and a little baby doll top. Usually Mistress Katja does my make up, but this time Tiffany took charge. I’m not a make up expert but I had the feeling that I had a lot more make-up than normal this time.
ALTERNATIVE ENDING ONE
When I was made up, Tiffany said, come over here, sissy. And I wobble over to where she was sitting on a high stool. "On your knees, you know what's next." and I knelt down in front of her.
She pulled her panties aside and pulled out her penis. "Start licking." I bent forward and touched
the tip of it with my tongue. I was very excited, I could feel the heat of my beaten ass, the exoticfeel of the clothes I was wearing. And right in front of my face was a dick.
I did the best I could with her penis. I licked up both sides, and then took in in my mouth. It was smooth, silky almost. It got harder as I ran my mouth up and down it. I took the base with my hand, and rubbed in time with my sucking. After a few minutes, Tiffany pushed me back and stood up.
Remaining on my knees, I looked and saw that Mistress Katja had put on a strap on. The strap-on was about the same size as Tiffany’s cock, but black. Tiffany led me by the hand over to the bed I had seen earlier. Mistress Katja said "on your knees." As I knelt on the bed, I saw Mistess Katja give Tiffany a long kiss. Then Mistress Katja said "which end of this do you want?" and Tiffany replied "I want a piece of that nice red ass."
They kneeled in front of and behind me. I took Mistress Katja’s strap on in my mouth and felt Tiffany’s finger go up my ass. She reached over and I felt her putting some sort of lube. It was hard to concentrate on keeping the strap-on in my mouth as Tiffany’s fingers went in and out of my ass. Then I felt her cock at my ass, and it squeezed in. It hurt and I gave a little gasp, but Mistress Katja held my head in her hands and kept my mouth on the strap on. Tiffany slowly pressed her cock in my ass. When it felt like it was pretty far in, it still hurt, and then she began to push, in and out, in and out. As she pumped me, I felt the hurt decline, and then I started to move with her. I realized that I was flying high, I was totally at the whim of of these two beautiful creatures, I was a total sex toy, and I was being fucked. I felt Mistress Katja and Tiffany lean together above me, and imagined them kissing, although I couldn’t see them. I felt the plastic strapon deep in my mouth, and my ass opening to receive Tiffany.
Mistress Katja came first, holding my head steady as she climaxed. Soon after I felt Tiffany pull my hips tight towards her and pulse into my ass. My poor penis strained against the chastity device. Mistress Katja pushed me off the bed, and Tiffany and her lay side by side, gently kissing.
"Did you like my sissy?" Mistress Katja asked.
"Oh yes, she’s sweet and fuckable." Tiffany replied.
Mistress Katja turned to me, kneeling by the bed. "Wash your face, dress and leave. We’re going to be here a few more minutes."
When I left, Tiffany and Mistress Katja were necking on the bed. My ass was dripping what I assumed was cum, but could also be Santorum (Dan Savage’s word for the mixture of cum and lube that drips from one’s ass.) I felt totally used and degraded, which was what I had hoped for.
ALTERNATIVE ENDING TWO
After my make up was complete, Mistress Katja had me take off my chastity device. She then put my cuffs back on my wrists and ankles and led me over to a chair which was bolted to the floor near the bed. She locked one arm and both legs to the chair and put a bottle of lube on the floor by the chair.
"Tiffany and I are going to let you watch us make love. You can masturbate as much as you want, but you are not allowed to come. Can you do that? Because if you come, you will be punished."
I watched as they fell into each other’s arms and back on to the bed.......
ALTERNATIVE ENDING THREE
After my make up was complete, Tiffany stood back and looked at me. She turned to Mistress Katja and said "She’ll do, I’ll take her." She went to her purse and took out what looked like two large band-aids. As she stuck them on my belly, she told me they were the beginnings of my hormone therapy.
Mistress Katja came over and handed Tiffany not only the box with the key to my chastity device but also my emergency key, which she had inspected earlier. Mistress turned to me and said "I’ve sold you to Tiffany. You won’t see me again, but you are now Tiffany’s property."
Tiffany said "I’m going to help you become a she-male like me. That’s what the hormones are for. I want you over at my place tomorrow, it needs a good cleaning."