My Sissy journey - Sex Stories

My Sissy journey

Since I still lived with my parents, it was not possible for me to order an appropriate toy. So I used what was there: fruits/vegetables, everyday objects with the right shape, ...

I found more and more pleasure in this and became more and more excited, the more often I introduced myself some anal. But at some point, this sensation was no longer enough. I got a craving for real cocks and watched more and more gay porn. But even that wasn't enough at some point, I needed the real thing. Every now and then I felt bad for these thoughts, but they became stronger and stronger.

One night I decided to put an ad on the internet looking for men who wanted to fuck me. I was specifically looking for mature men, as these turned me on in particular. The amount of messages was overwhelming and made me even hornier. I quickly found a suitable applicant and wrote a little with him. I masturbated several times on the chat and the thought of finally being taken by a man. But when it should be so far I pinched out of fear and discarded the thought of a meeting for the time being again.

A year later, I moved into a shared apartment with two friends. Finally I could order what I wanted. So I ordered an anal douche, lube, a dildo and a set of three anal plugs. After a lot of pleasure with the new toys, the desire for a real cock came up again and I put a similar ad online again. This time, too, many men wrote to me. When my roommates were out of the house, I arranged a meeting at my ...

... place.

The man was in his mid-30s, actually a bit young for my taste, and reasonably good-looking (although I didn't really care). Before he got to my place, my heart was racing. I had never been so excited. When he was finally there he talked to me briefly, but I didn't listen at all because I was already fully focused on what was to follow. Finally he pulled down his pants and took out what I had been waiting for so long. I immediately got down on my knees and started stroking and licking it before taking it all the way into my mouth and sucking on it. I had no experience yet, but in my opinion I was doing a good job (at least I would have liked it a lot myself). However, his cock did not get hard. After a few minutes he broke off and left again and I was left disappointed.

Still completely horny and excited, I then fucked myself with my dildo and went to sleep. Dissatisfied, I resumed my search for cocks.

Quickly a man came forward who was promising. He was already 56yo which pleased me very much and apparently I pleased him as well. At the next opportunity I invited him to my place. On the day of the meeting I was horny all day and again extremely excited. I wondered what he would look like, how big his cock was and what he would do to me. So I prepared myself, cleaned my asshole and inserted an anal plug. Shortly before he came I took it out again and opened the apartment door for him, dressed only in shorts. He was a little smaller than me had gray hair and a gray ...