I had the ultimate humiliating sissy experience while going through puberty, and I think it made me a sissy for life.

I've been writing down the story.. not done yet - but here is chapter:

When I was 14 I met this girl from school; she was the beautiful daughter of a wealthy farmer nearby. We were both sexually very shy. I had been jacking off to porn magazines for a couple of years, but was inexperienced with girls. I also had a secret that I never told anyone - I liked to insert objects in my ass sometimes and had been doing it since I was maybe 13. I didn't think I was gay because I liked girls, but I really liked the naughty feeling it gave me when I played with my own ass, and would occasionally fantasize about being the girl. The first time we were going to have sex, I couldn't get hard. I was so embarrassed and the whole incident was very traumatic for me, but we stayed together as girlfriend and boyfriend. Shortly after that I got a summer job working on her father's land - my job was to walk around planting trees in the forest. Most days I was working together with an older man that was a full time employee on the farm. He was mid-50's and had worked on the farm for many years.

This guy - let's call him Billy - was a widower and I picked up already the first day that he was perving over both the daughters on the farm, both my girlfriend and her older sister. He kept asking me if we were "doing it". I was shy and didn't want to to say, but he managed to pry more info out of me as the first week passed. We had lots of time to talk and Billy soon got more and more crude in his questions. He kept hinting that my girlfriend needed a "real man" and not a skinny teenager like me. His comments humiliated me because i had been limp in bed with her just days before, but didn't want to tell him. On every break he would ask more questions, like what panties she wore or if she had a hairy or shaved pussy. I could tell that he was enjoying watching me squirm when I got embarrassed by his questions. He asked me if I had a small dick and he bragged about how big his was. One day he asked - "so does she take it in the ass?" and after I said no, he kept talking about how normal it should be, because it feels so good. I laughed and tried to joke the subject matter away because I was ashamed of my own anal experiments. Then suddenly he asked me if I had ever put anything up my own ass. I was horrified with myself answering yes. I couldn't believe I had said it and I regretted it but he was already asking more questions and laughing at me. "what did you use?" I was terribly embarrassed but he was prying more and more information out of me and I told him that I had used a pen, a carrot, a perfume bottle etc. I regretted telling him because now he was starting to make more fun of me, saying that i had skinny arms like a girl, that I wasn't a real man like he was, and towards the end of the second week he asked me to bring me a pair of my girlfriend's dirty panties for him. I was horrified at this, and said I wouldn't do it. He said he would tell my girlfriend that I like to stick a carrot up my ass. In retrospect I realize he would probably never dare to tell her that, but I agreed to do it. After I agreed, he said that he wanted panties from both the sisters and the mom too - one clean pair and one dirty pair from all three. So that weekend when visiting my gf, I went through the laundry basket and got what he had asked for. I couldn't get to the mother's bedroom to get the clean pair, but managed to get the rest of what he has asked for,

After parking the car at the end of the dirt road the following monday , he asks if I have the panties. I feel bad about it, but also strangely turned on and scared by the situation. We are in the middle of the forest miles from people and Billy is acting very tense. Billy takes the panties out of the plastic bag and holds them up. "What do you think will happen if I told my boss you stole his wife and daughter's dirty underwear?" I protest and say that he told me to do it and that I wouldn't have done it otherwise. He says he wants proof that I will never tell. "You will wear xxxx's panties and pose for a picture" What?! I can't believe what I was hearing, but I'm becoming aware that he could actually blackmail me, in fact he is already blackmailing me. He is so big and powerful and so much older than me and from that point I kind of give up and do as I'm told. He holds up one of the dirty panties, I think it was belonging to the older sister, and moves the crotch right up to my nose - and asks me to describe the smell. At this point I feel terribly humiliated and ashamed, but it was about to become a lot worse. He makes me tell him where the different smells are coming from, and to use the names of the sisters and their mother - like "it's from xxxx's pussy" or "it's from the asshole of xxxxxx". Then he tells me to get out of the car and get undressed. My penis is limp and I feel small and embarrassed. Billy hands me a pair of the clean panties - they are white - and tells me to put them on. I feel ridiculous wearing panties and Billy adds to my humiliation by asking what I was thinking about when I played with my ass like I had admitted to doing. I get so embarrassed and so shy that I almost start crying but Billy just laughs at me tells me to turn around, drop my panties and spread my cheeks. To my horror he comes closer as I'm standing bent over with spread buttocks , and looks closely as my asshole. At this point I do start crying. Billy tells me to be a good girl and spread wider. I feel what feels like a vaseline-covered finger between my cheeks and suddenly i feel a fingertip being pushed through my sphincter. He makes me tell him that I will be a "good girl" for him. "uh..I'll be a good ...girl". At this point I don't dare look and suddenly I feel the big, warm head of his cock on my asshole. He starts pushing against it with slow but steady force, stretching my asshole slowly to accommodate his cock. As I relax a little bit, he suddenly plunges his shaft in all the way, keeps pushing his cock deeper so his big balls touch mine.

/r/Sissies Thread