When I was 17 years old, I was experimenting sexually. I was a handsome guy of 65 kg and 1.82 so very slim. I had a very feminine figure, female hips and ass and very intrigued to be sissy for an older man for once. Not only that, but I had done some chatting on gay chat rooms and had some sex dates but never as a sissy and decided to go for it fully.
So, I had come into contact with a man ‘Richard’ through a chat room. Pictured is the delicious sissy Nicolette.
He was 63 years old, and we really had a click. Richard could help me take the step as a sissy and feel like a woman. He lived in Antwerp and had all the women’s clothes I dreamed of trying on.
We had an appointment, wow, so exciting! I was a little scared, but I couldn’t go back, since I had promised to meet him, and he had to take time off… The guilt was too much to call off and so I got ready by shaving my body completely bald, rinsing my ass and putting on my most feminine clothes, this was limited, I had mega tight pants and a thong.
You could see the thong through it a bit, and on the way to Richard’s I was already trying to practice a little by stepping feminine. The feeling of the thong in those exciting shorts made me horny. Once I arrived, I gathered all my courage and rang the doorbell. Richard opened the door and looked at me from head to toe. He looked older than in the pictures. ‘Looking good, come on in’ he said.
Once inside, he told me I could get ready upstairs in the room on the left and to come down when I was ready. Full of excitement, I walked upstairs, he squeezed my ass and went back into his living room as if it was the most normal thing in the world. I didn’t believe my eyes when I opened the door upstairs! A room full of women’s clothes, lingerie, wigs, high heels, boots, Panties, false breasts, butt plugs, collars, makeup, …. WOW!
Like a kid in a candy store, I got a wide smile on my face and felt the tension change to a very horny mood. I started to pick out some things and also wanted to be completely woman with a whore look. I took the highest black heels, red stay-up net stockings, a black corset and thong and tight in these also the false breasts. A blonde wig with ponytails,a pink choker/necklace with slut written on it and a leather skirt. There was a make-up table, so I started to make up. A little mascara and red lipstick.
The result was really hot. I’m a sissy
The result was really hot. I wanted to look perfect and was a little scared to see him again, so I was taking my time. Time apparently flew by because suddenly I heard him at the bottom of the stairs, and he said’ are you almost done? I have to go out later! ‘ I hesitated a bit but said’ yes, I’m coming down’ in a hesitant voice.
Carefully, I went down the stairs with the high heels and opened the screeching door of his living room. He was sitting in a dark corner with his cigar, staring at me. I felt like a whore. He ordered me to come to him and turn around. He inspected me completely with an approving look.
He put on his cigar and opened the zipper of my skirt and let it slide down my legs slowly. Now he began to inspect my buttocks and pulled them apart a bit to see if I was well shaved and flushed. Good riddance! He patted my buttocks well once until they looked red. He stood up and whispered in my ear,’I’m going to turn you into a real sissy whore, that collar looks fantastic on you’.
He put a blindfold on me
Then he walked into another room and came back with some more stuff…. I didn’t see what it was, but was very curious. He put a blindfold on me and ordered me to lean over the seat while he pushed me forward with his big hand on my neck.
My thong was pulled down, and he pushed a cold metal butt plug into my ass. I moaned softly, but let him do it. Then he pulled me upright, turned me around and clicked something around my pecker which was very tight. He pulled my thong back on, patted my ass again and turned me back around and clicked a chain to my collar. So we’re done, he said. The blindfold came off, and I saw that he had put a pink penis cage on me and a chain on my collar. Both were secured with clasps.
I turned all red because this was not what was agreed! ‘You mustn’t blush, sissy. You know very well that you are a slut otherwise you wouldn’t have dressed so whorishly’ he said with a grin on his face. ‘From now on you’re my property and you won’t be needing that dick anymore.
I was shocked so hard by this upheaval, but I found it so horny. He ordered me to get on my hands and knees and guided me to another room like a dog by pulling the chain a bit. It was a kind of laundry room with no windows, with a blanket on the floor and a bowl of water.
He ordered me to get down on my knees with my hands behind my back and took a gag ring out of his pocket and tied it to my head so that my mouth was open. I could no longer close my mouth or say anything. Then he took his pole out of his pants and thrust it deep into my throat. I couldn’t breathe anymore and had to gag but couldn’t close my mouth.
He pulled hard on the chain
He pulled hard on the chain, so I couldn’t pull out and tears were running down my cheeks, this was so hard. He started fucking my mouth and the slime ran down the corners of my mouth. My make-up was also running all over the place, He was obviously only thinking of his pleasure and started fucking my mouth harder and harder.
I couldn’t breathe anymore and pushed my hands against his legs to catch my breath again. He said ‘so-so, that throat of yours needs some training’ He grabbed my chin and spit in my face and mouth and gave me a pat on the cheek. He went back out of the room and came back with hand and ankle cuffs. Not only that, but he clicked my hands and ankles and also put the key back away.
Now I’m going to teach you not to pull back
Now I’m going to teach you not to pull back, sissy. Still completely dripping, he stuck his pole back in my mouth and thrust hard against my throat and kept pushing until the mucus was coming out of my nose. I couldn’t take anymore, but he didn’t much care. I closed my eyes for a moment but he gave me a smack in the face and said “this is what you want, look in my eyes, whore!” . He squirted all over my face and mouth with a loud moan….
Not bad for your first time, but I that resisting still needs to be worked away. I couldn’t even answer because that thing was still in my mouth and my arms and ankles tied up and had to pant to catch my breath. He pulled a bit on his metal leash and secured it to a ring in the wall. Zoo, I have to leave for a while, you’ll be fine here for a while, see you later!
He locked the door and left me like this. The cum was still dripping from my chin, and the ring gag kept the saliva dripping from my mouth. I lay down on the blanket and tried to drink from the cup. From this intense experience, I was so thirsty. I began to realize what a dark sex game I was playing.