My Sissy journey - Sex Stories

My Sissy journey

... However, in that time I had to move because of my job and my old fuckbuddy was therefore too far away.

I ordered myself women's clothes, or at least an outfit. There were ankle boots with high heels, stockings, a sexy red body, a tight wetlook dress, a figure-hugging long-sleeved top and a cloth mask where only the eyes were cut out. The mask had the reason that I still led a normal life. My face was quite masculine and I had a full beard, which of course does not fit at all to a sissy. In this outfit I often fucked myself with toys and trained walking on heels. In the process, I became more and more friends with the idea of being a pure submissive pleasure object. So I went on the search for cocks again.

Quickly I had found someone who I liked and who wanted to fuck me. I invited him to my place. When it rang, I opened the door to him. I wore only the stockings and the red body. He liked my outfit and we quickly went into the bedroom. Contrary to my ad and the messages before the meeting, he was rather gentle and cuddly, which of course was not what I wanted. Nevertheless, I went on my knees after his pat down(as long as I get cock).

He put his quite big dick through the additional small hole in my mask directly into my mouth. After I had sucked him a bit he signaled me to lie down on the bed. There he then wanted to lick my sissy clit, which I no longer consider a penis for a while. However, I told him that I didn't want that. After he continued on his cuddling ...

... course, I told him that he should finally fuck me.

No sooner said than done and I finally had his nearly 7 inches cock inside me. What he lacked in dominance he fortunately made up for with stamina. He fucked me not particularly hard but for about an hour in all possible positions. In the end he came on my body and left.

Days later, I went back to the search, somewhat disappointed. Quickly a 33-year-old man came forward, to whom I first wrote that he was too young for me. Nevertheless, he wrote me something about himself and sent a picture. He described himself as athletic, active and dominant, so far so good. But what really aroused my interest was the picture. He was very muscular and his cock was huge, at least 8 inches. He also wrote that he could introduce me to a gentlemen's round, in which there are exclusively mature gentlemen. I replied with great interest. He then told me that he liked me very much and that he would like to test me before introducing me to the others.

When it came to the meeting I was a little nervous because of the size of his penis. I had never had anything so big in my tight boypussy. Not even my dildos were that long and thick. We met at night in a secluded forest parking lot.

When I stood in front of him, he grabbed me by the shoulder and forced me to my knees. I was immediately in ecstasy. The size of his cock overwhelmed me a bit. I only got a little more than half in my mouth before I started to gag. Still, he continued to push my ...