SUBUrbandDad
Experienced
- Joined
- Jul 23, 2023
- Posts
- 9
My name is Thomas, I'm 21 and work as an apprentice carpenter.
We met online, one night while I was exploring my submissive fantasies. I'd always thought that they would never be more than that. Fantasies.
You, a Dominatrix, answered a post I had made in a forum for submissives and we started chatting. In order to get your interest, I had to perform some tasks for you. It started out fairly innocent. Show my cock, no face. Then masturbate for you. Buy a pair of panties and wear those while masturbating. This stretched over the next few days, and your requests get increasingly demanding. But I loved the attention and you allowed me to cum for you. Then after two weeks, you told me you had a final request for me to prove my worth to you. To show you that I was really yours. After which you would meet me in real life. You asked me to purchase a femboy starter package from a webshop, which consisted of a pink lace bra and panties, a dildo and a butt plug. You wanted me to wear the underwear and then while on cam with you, lie in my bed and fuck my ass with the dildo.
I was really nervous, as I had never tried anal before, but you told me what a big turn on it was to have someone take their own anal virginity in front of you and the thought of pleasing you made me agree to do it.
Still being nervous about exposing myself, I placed the camera so that my face was not visible. I put on the underwear. It felt really soft and smooth. Then I got on the bed on all fours with my ass facing the camera and started playing with myself. I pulled the panties down between my thighs, exposing my asshole. Using lube I slowly inserted a finger. The excitement and the taboo of it all alone, had my cock erect between my legs, even before I started touching myself, but inserting the finger, made my cock spasm slightly. It was such an odd sensation. Not the normal feeling of pleasure, and yet I was so sensitive there.
You told me what a good boy I was and asking me to go ahead an insert the dildo. You did not want my asshole stretched too much before the insertion. I applied lube and did as you asked. I had to do it very slowly, because of the pain when my asshole was stretched. It was just a normal size dildo, but the pain from my stretched asshole was very intense and I wimpered while pushing it in. Once inside, the pain subsided somewhat and I showed my ass to the camera with the shaft sticking out.
You praised me once again for being a good boy, and now wanted me to lie on my back and jerk myself with one hand while fucking my ass with the dildo with the other. I needed to learn to associate being fucked in the ass with pleasure and cumming. I turned around and did as you asked and by the end of it all I was moaning loudly while fucking myself and ended up spraying my cum all over my own chest.
This is where you asked me to use my fingers to scoop it up and lick my own cum off my fingers. You had asked me to taste my own cum before, but I had never had the courage to do so. This time, I was so worked up with excitement that I just did it without thinking, when you told me to.
The session ended with you telling me what a good boy I had been and that I had given you exactly what you needed.
It wasn't until after you hung up, I noticed that in my excitement, I had shifted position so my face had been clearly visible when I was lying on my back, fucking myself, cumming all over myself and then licking it up. Oh well, I would probably have to show you my face at some point anyway, and I had no reason not to trust you, right? So far you had been very good to me and helpful in my journey of self-exploration.
Of course, I did not know yet that you owned the webshop where you had requested me to buy the femboy package from, meaning that now you not only had my name and address, but credit card information as well.
We met online, one night while I was exploring my submissive fantasies. I'd always thought that they would never be more than that. Fantasies.
You, a Dominatrix, answered a post I had made in a forum for submissives and we started chatting. In order to get your interest, I had to perform some tasks for you. It started out fairly innocent. Show my cock, no face. Then masturbate for you. Buy a pair of panties and wear those while masturbating. This stretched over the next few days, and your requests get increasingly demanding. But I loved the attention and you allowed me to cum for you. Then after two weeks, you told me you had a final request for me to prove my worth to you. To show you that I was really yours. After which you would meet me in real life. You asked me to purchase a femboy starter package from a webshop, which consisted of a pink lace bra and panties, a dildo and a butt plug. You wanted me to wear the underwear and then while on cam with you, lie in my bed and fuck my ass with the dildo.
I was really nervous, as I had never tried anal before, but you told me what a big turn on it was to have someone take their own anal virginity in front of you and the thought of pleasing you made me agree to do it.
Still being nervous about exposing myself, I placed the camera so that my face was not visible. I put on the underwear. It felt really soft and smooth. Then I got on the bed on all fours with my ass facing the camera and started playing with myself. I pulled the panties down between my thighs, exposing my asshole. Using lube I slowly inserted a finger. The excitement and the taboo of it all alone, had my cock erect between my legs, even before I started touching myself, but inserting the finger, made my cock spasm slightly. It was such an odd sensation. Not the normal feeling of pleasure, and yet I was so sensitive there.
You told me what a good boy I was and asking me to go ahead an insert the dildo. You did not want my asshole stretched too much before the insertion. I applied lube and did as you asked. I had to do it very slowly, because of the pain when my asshole was stretched. It was just a normal size dildo, but the pain from my stretched asshole was very intense and I wimpered while pushing it in. Once inside, the pain subsided somewhat and I showed my ass to the camera with the shaft sticking out.
You praised me once again for being a good boy, and now wanted me to lie on my back and jerk myself with one hand while fucking my ass with the dildo with the other. I needed to learn to associate being fucked in the ass with pleasure and cumming. I turned around and did as you asked and by the end of it all I was moaning loudly while fucking myself and ended up spraying my cum all over my own chest.
This is where you asked me to use my fingers to scoop it up and lick my own cum off my fingers. You had asked me to taste my own cum before, but I had never had the courage to do so. This time, I was so worked up with excitement that I just did it without thinking, when you told me to.
The session ended with you telling me what a good boy I had been and that I had given you exactly what you needed.
It wasn't until after you hung up, I noticed that in my excitement, I had shifted position so my face had been clearly visible when I was lying on my back, fucking myself, cumming all over myself and then licking it up. Oh well, I would probably have to show you my face at some point anyway, and I had no reason not to trust you, right? So far you had been very good to me and helpful in my journey of self-exploration.
Of course, I did not know yet that you owned the webshop where you had requested me to buy the femboy package from, meaning that now you not only had my name and address, but credit card information as well.
