Sissytime

Sissytime

I have been crossdressing since I was young. The feeling of women's clothes, the way I look in the mirror, it makes me feel sexy, it makes me feel complete. With the advent of the internet, I fell further down this path. Reading and listening to stories about crossdressing, and later sissification, expanded my practice. I also benefitted from the ease with which I could procure lingerie from Amazon. As time went on, I began to masturbate with more than my cock. I discovered my ass. It has been an amazing experience. I get the most pleasure from wearing a tiny chastity cage and chasing the elusive sissygasm. I have trained my boipussy well, and can occasionally cum from anal only, while my clitty is locked away. I feel so sexy when I do this. When I masturbate by fucking my boipussy, the sensations are amazing. I have taken my anal training very seriously, and I can take very large dildos. While this is very satisfying, I also enjoy dressing up for my wife. She has been very supportive, although she is not as into my sissy side as I am. When I am home alone, I can fuck my boipussy for hours. I can't get enough, and thanks to chastity, I force myself to keep trying!

I recently searched for a place to do my thing in a video chat with other sissies. I came across a topic on reddit about where to go for free video chat discussion. One sissy posted about her experiences when she chats on Flingster. She explained that she likes to help guys come- as many as ten on one occasion, in fact. I have never thought about this before. I was mainly interested in finding a mutual session with another sissy. I decided to give it a try. Once I locked my clitty away in my micro cage, I put on a crotchless body suit and thigh-high stockings. My silicone fake titties are an A-cup, and they have pencil eraser nipples. When I am wearing them, they look like they are really mine. Once in a while I will wear D-cup titties, when I feel really slutty, but for day to day sissy me, I prefer the A-cup.

Once I was dressed, I laid out the lube and three dildos, large, extra large, and a giant brown one. It takes me a while to work up to it, but once my boipussy is ready, she can take all 14 inches of the brown monster! I arranged myself in front of a mirror so I could get a full view of myself. I logged on to the chat, and I added the hashtag sissy. I figured I would find other guys to play with. Wrong. I was bombarded with men of all shapes and sizes stroking their cocks. Some showed their faces, some just their cocks, but they were all stroking. I remembered the reddit post, and to my own surprise, I immediately flipped into sissy cumslut mode. I decided to try to help a random guy come. I told him to talk dirty to me, and how I wanted his cum, and wanted him of fuck my asspussy.

As I pumped the first dildo in and out, and said I wanted him to fill my asspussy, he came right away. It was a lot easier than I would have ever imagined. The next. Guy asked me to turn around so he could see the dildo pumping in and out. I obliged. I asked him to make me his slut. He was much more aggressive, and he told me how he was going to pound my ass. He praised me and said he liked my chastity cage, and liked my sexy outfit. I was ready to take th biggest dildo, and whenI showed him he said he was going to fuck me hard and deep, and demanded that I take the whole thing. I called him daddy and said "Daddy, it's too big, I can't take it all".

He told me exactly what to do, and it was as if his hand was controlling the cock in my asspussy. I loved being controlled. My cock is dripping right now as I write this thinking about it. As I pumped the cock in and out, he told me he could hear the balls slapping against my ass. I fucked myself harder and harder, and I could feel the balls slapping against my own balls. In my sexiest girly voice I told daddy I was going to cum ( I was not, but I squealed and moaned in a high pitched voice, telling him how good hick cock looked and felt). He was also ready to cum, and as I pounded my asspussy for him, he came in ropes, calling me hie fucking sissy slut. He disconnected immediately afterward.

The next guy immediately popped up on the screen, and the show started over again. Some guys swipe immediately, but surprisingly, some linger. A young guy popped up, and I could see by the look on his face that he was shocked to see a sissy, in chastity no less! I spoke softly to him, in my girliest voice. I told him it was okay, and I was going to help him cum. I told him I was going to suck his cock, and I would take it all down my throat, so it would be covered in my saliva, and then he could slide his big cock it into my asspussy. I moved the camera so he had a closeup of the dildo I was ramming in and out of my asspussy, and I told him to fuck me harder, I was really pounding the cock into my ass, and I could see by the way he was stroking around the tip of his cock he was ready to cum. He began stroking his sensitive glans, and he began to cum.

I told him to cum in my asspussy, and begged him to fuck me harder, and that if he didn't stop, I was going to cum too. I told with him to fuck me harder, and was drilling the entire length of the dildo al the way into my boipussy. It felt amazing as I gripped the shaft with my inner gurlpussy muscles. When he started to cum, he shot two or three short spurts at first, and I could feel the verge of my own orgasm. I told him I was cumming, and he unloaded a torrent of cum. I pleaded him to cum in my asspussy. This pushed me over the edge, and I started to cum as well. It was amazing. I told him I wanted to swallow his cum, and even though I never do this, I wiped up my own um and sucked it off my fingers like a greedy little slut. I was drunk with lust. I thanked him for his cum and for making me his little slut. He thanked me, and disappeared from my screen. I swiped to the next.

I played for at least an hour, and got three more guys to cum for me that afternoon, but I did not cum again (I am a sissy, so don't always get to cum. I don't have to. I enjoy the feelings I get from playing with my boipussy so much, I don't need to. I enjoyed being dressed up, in chastity and having my boipussy filled. And now I have also discovered that I like to be a subservient little bitch).

So that was my first experience online. I went from sissy seeking sissy to depraved cumslut helping random guys jack off, begging them to fuck me and degrade me, and I loved it. I have gone there again several times, and every time I make men cum with my little sissy show. It is so much fun. I love it when they tell me that to do, and also when I find a young guy who I just horny and looking to jerk off, and gets more than he bargained for. I hope to also hook up with other sissies I can play with and help cum, but I'm starting to think it will not be as much fun and being controlled by a daddy.