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 mustache. He introduced himself, came in, followed me into my room and immediately began to undress. He touched me all over my body and took off my pants. Then he stood behind me, rubbed against me and kissed my neck. Afterwards he sat down naked on the edge of my bed. I immediately knew what to do and got down on my knees. His cock was not particularly large and slightly hairy, but quite nice and especially already hard.
I started to blow him, whereupon he placed his hand on my head to guide me. I quickly noticed how the first drops of precum ran into my mouth and down my throat. The taste turned me on even more. After a few minutes I stopped, climbed on the bed and presented him on all fours my tight, virgin asshole. He meanwhile put on a condom and positioned himself behind me. I suddenly felt how his tongue and his beard tickled my rear entrance. This was followed by a bit of lube and his cock. I felt a short pain at his penetration, but it immediately turned into pleasure and ecstasy. He took no account of my virginity and took me pretty hard from behind, which pleased me very much. So this went on for a few minutes and he became faster and faster until his cock pulsated in me and he came.
After that he pulled off the condom, I licked his cock clean and he disappeared again.
I remained lying on my bed, overwhelmed by the pleasure I had just felt, and also made my cock squirt. I had finally done it and it was a great feeling, but that should not be the end.
I met more often with the same man. The meetings were pretty similar, sometimes at his place sometimes at mine.
Before the next meeting (I no longer know how many it was) I wrote him a message in which I asked him to proceed a little differently this time. I was now mainly watching gay porn and it was getting more and more perverted. BDSM, sissy training, brainwash, gangbangs, …
Accordingly, my request to him this time was to use me like a will-less bitch and to be more dominant.
The meeting took place at his place. After I was in his bedroom and had only underpants on, he forced me to my knees and immediately pushed his cock into my mouth. I was a little surprised, but I loved being treated like that. After fucking my throat for a few minutes, making me gag repeatedly, he threw me on the bed. He ordered me to get on all fours like a good slut. He then fucked me very hard. I enjoyed every single firm thrust and was close to a hands-free orgasm the whole time (which unfortunately didn’t happen). The only thing that would have made the situation even better would have been a second cock in my mouth. When he was about to cum he pulled out and removed the condom. He threw me on my back, climbed over me and came deep in my throat and all over my face. I have never been so happy.
Confirmed in my fantasies, it went on for a while, even with other men. But I wanted even more. I wanted to become a will-less sex object and the term Sissy burned itself into my thoughts. 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 head down. When he was done with my throat, he pulled me by the arm to a table that belonged to the parking lot and threw me on my back.
He pushed my panties aside, spit on my greedy hole and slowly pushed his huge dick into me with its full length. I had never felt anything so fucking good. Overwhelmed by my horniness, my brain virtually shut down. He owned me completely. When he got a little faster and harder, choking me a little, I had my first hands-free orgasm. Completely unimpressed, he continued while my moans grew louder and louder. I noticed how he was getting closer to his climax. Just before he pulled out his cock he stripped off the condom and came all over my body. The load was huge. I immediately set about licking him clean, a little sad that it was already over after about 15 minutes.
My disappointment quickly turned when I saw him take a new condom out of his pocket and slip it on. He brought me rudely back to my feet and bent me forward over the table. Before my brain reacted he was already fucking me again. This time even harder as he held my hands on my back to get momentum. Only a few seconds later I came again. After another 20 minutes of pounding he was close to orgasm again, this time cuming on my ass and the back of my dress. And again I set about licking his dick clean.
He forced me to suck his cock again until he blasted another load all over my mask. Never before had I seen someone cum three times in a row and especially not with such a amount of cum. When I was about to leave he held me tight and ordered me to walk a big round through the nearby town and offer my services to everyone I meet. So off I went with loads of sperm on the mask, the wetlook dress, the stockings and very wobbly on my legs. Fortunately (or unfortunately) I met but no one.
Back at the parking lot, he pressed $5 into my hand and told me I wasn’t worth more and disappeared. I liked that a lot for some reason and went home satisfied. The next day I got a message with: Test passed. Seconds later he introduced himself as Mike and told me he will message me again.
During all that time, I led a double life, so to speak. I lived normally as a man, went to work, even had a girlfriend. My girlfriend worked in shifts, so I often had time for meetings.
In the days after the meeting with Mike, to my amazement, even a dominatrix had contacted me, who wanted to have me as her property. Desperate and submissive as I was I agreed after some chatting. She wanted to prostitute me and keep the money. This excited me very much and I liked to be humiliated.
I also gave my new mistress the contact to Mike to discuss the meeting with the gentlemen round, because I was incapacitated for the time in which I was active as a sissy. A few days later I got a message from my mistress with a time and place. It was the parking lot where Mike had fucked me and at midnight I should be there again. In the meantime I had also bought a penis cage that I wanted to wear to the meeting.
Finally, the appointment had come. I prepared myself extra thoroughly and was very excited and full of anticipation. I put on my slutty outfit, locked the penis cage and drove to the parking lot. There my mistress and Mike were already waiting. He handed her money (I didn’t care about the amount), whereupon she wished us a good time and left. Mike then led me to the far corner of the parking lot. Where 7 men, all over the age of 50, were already waiting for us naked. In the middle was a blanket on which I should kneel down. The men lined up in a circle around me and then it started.
Everyone who was just after it pushed his cock down my throat. At the same time, I jerked one cock each with my hands. The others watched me and also jerked their dicks. After everyone had a turn, I was ordered to get down on all fours.
One of the men positioned himself behind me. I quickly noticed that he had no condom on. I told him to please put one on. But there was no reaction and he pushed his cock bareback into me. My negative thoughts were gone in just a moment and I gave myself fully to their cocks. The first man took me doggy relatively slow but quite hard.
Meanwhile, another knelt in front of me and pressed my mouth on his penis. And again I felt unbridled pleasure. After a few minutes I noticed how my first candidate came and squirted his whole load deep into my hole. This feeling was extremely good, yet I would have liked my first creampie from Mike’s giant dick.
So it went on. Again and again a new cock with the sperm as a lubricant penetrated me and filled me even more. The one or other load also came into my mouth. Regularly I also got spanked which excited me further. My asshole was slowly loose and yet it went on and on. After about three hours, the men slowly let go of me. With sharpie they wrote hooker, sissy, bitch and other humiliating things on my ass, my legs and my belly. Afterwards, they took photos of me lying on the floor smeared with cum and sharpie.
When they were all gone, I slowly got up and walked very bumpily to my car. I was extremely exhausted, but also extremely satisfied. Back in my apartment, my mistress wrote to me that I had done well. On the question of how they know that, I got only a link. The link led to a porn site. Apparently the men had secretly filmed the whole gangbang and uploaded it there.
On the one hand I was shocked on the other hand I liked it somehow to be seen by even more men. Nevertheless, I was glad to always wear a mask.
After this expirience I finally felt like a real sissy slut if only part-time.